TWI588129B - Aromatic dispersant composition and use - Google Patents

Description

Aromatic dispersant composition and application

The present invention relates to a polymer, and a composition comprising a particulate solid, an aqueous medium, and a polymer chain having at least one fused aromatic fluorene imine pendant. The invention further provides a composition for aqueous abrasives, dispersions, coatings, and inks.

Many formulations, such as inks, paints, and abrasives, require an effective dispersant to evenly disperse the particulate solid in an aqueous or polar organic medium. Regarding ink, ink manufacturers want to manufacture high-resolution and quality printed products. The printing method poses a great challenge to the suitability of a wide range of base substrates, resins and pigments that have never been seen before. The pigment dispersion should be compatible with the different formulations used to ensure good adhesion and resistance to the final coating. Poor pigment dispersion or stabilization can cause cohesion or settling in polar organic liquid media or aqueous liquid media such as inks or coatings, reducing gloss and aesthetics.

U.S. Patent No. 7,265,197 discloses the dispersion of a pigment in an ink composition by a dispersant having the formula: Wherein R _{1 is} each selected from the group consisting of H and CH ₃ , and n is an integer from 4 to 400.

International Publication No. WO 2008/028954 discloses a quinone imine dispersant compound containing a terminal acidic group in both polar and non-polar organic media, wherein the dispersant compound is represented by the following structure: Wherein T is -(CH ₂ ) ₃ - or -CH ₂ CH(CH ₃ )-; R' is H or C _1-50 - optionally substituted hydrocarbyl, or C _1-50 - optionally substituted hydrocarbyl; Y Is C _2-4 -alkyleneoxy; x is 2 to 90; and q is 1 or 2, provided that in the formula (1a), when q is 1, T is -(CH ₂ ) ₃ -, And when q is 2, T is -(CH ₂ ) ₃ - or -CH ₂ CH(CH ₃ )-.

U.S. Patent No. 5,688,312 discloses an ink composition comprising a colorant, and the imine or quinone imine, and having a viscosity of from about 1 centipoise to 10 centipoise at a temperature of from about 125 to 180 °C. The quinone imine or quinone imine can be prepared by reacting phthalic anhydride with a mono or diamine. The monoamine can be, for example, dodecylamine or stearylamine. The diamine can be 1,12-dodecanediamine.

International Patent Application No. WO 2007/139980 discloses a At least one reaction product of a dianhydride and at least two reactants different from each other, the reactants each containing a primary or secondary amine group, a hydroxyl group or a thiol functional group, and at least one of the reactants is polymerizable. The reaction product can be used in compositions such as inks and coatings.

U.S. Patent No. 6,440,207 discloses a method of preparing a dispersible dry organic pigment for an aqueous system by (a) grinding a mixture comprising: (1) one or more organic pigments, (2) relative to the organic pigment Is at least about 1 weight percent of one or more aromatic polyalkylene oxide dispersants, (3) from 0 to about 10 weight percent of the abrasive liquid relative to the organic pigment, wherein the organic pigment is substantially insoluble, (4) a grinding additive other than the dispersing agent (2) of from 0 to about 50% by weight of the organic pigment, and (5) one or more surface treatment additives of from 0 to about 20% by weight relative to the organic pigment; (b) optionally adding one or more liquids to the ground pigment (6) wherein the total solids content is not reduced to less than about 10%, the organic pigment is substantially insoluble, and (7) One or more polyvalent metal salts and/or one or more quaternary ammonium salts; and (c) isolating the ground organic pigment. The aromatic polyalkylene oxide dispersant can be reacted by reacting 250 g of deionized water, 19.8 g (0.100 mol) of 1,8-naphthalic anhydride, and 105 g (0.105 mol) in an autoclave. Jeffamine ^TM XTJ-506 (83 wt% of ethylene oxide, 17 wt% of propylene) is prepared. The autoclave was sealed, heated to 150 ° C with stirring, and maintained at 150 ° C for 5 hours. After the reaction was cooled, the resulting brown liquid was discharged into a beaker, and then 15 g of decolorized charcoal was added. After stirring overnight, the suspension was filtered and the filter pad was washed with water to yield approximately 500 g of amber filtrate with a solid content of 23.63%. The dry pigment can be used in aqueous paint systems.

It is an object of the present invention to provide a composition which at least improves color strength and other coloring properties, increases particulate solid loading, forms an improved dispersion, improves brightness, produces a composition having reduced viscosity, and maintains stable dispersion. , reducing the particle size and reducing the particle size distribution (generally falling to an average of 150 nm or below, such as in the range of 70 to 135 nm), reducing haze, improving gloss, improving color strength, and increasing jetting (especially when the composition When the object is black). The composition of the present invention is stable under both ambient temperature storage and high temperature storage conditions.

Electron-based groups are well known to those skilled in the art of organic synthesis. Examples of electron withdrawing groups include, but are not limited to, halogen (e.g., -Cl, -Br or -F), nitrile, carbonyl, nitro, sulfonyl, sulfonate, hydroxy, or amine.

The electron withdrawing group can be an activating group or a passivating group.

The activating group may include a hydroxyl group, an amine group or a halogen. In general, the activating group can include a halogen such as -Cl.

The passivating group may include a nitrile, a carbonyl group, a carboxyl group, a nitro group, an amine sulfonyl group, or a sulfonic acid group. In general, the passivating group can include a nitro group, a carboxyl group, or a sulfonic acid group.

In general, the electron withdrawing group can be a passivating group.

In a specific embodiment, the present invention provides a polymer comprising a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is represented by formula (1): Wherein each variable may be anywhere, respectively, Q is R ₁ may be bonded to the ring may be substituted on the substituent group, and R ₁ respectively, by at least one electron withdrawing group (e.g., -CN, -NO _2, -SO ₂ NR ' ₂ , -C(O)R', -SO ₃ M, -C(O)OM, halo (e.g., -Cl or -Br), -NH ₂ , or -OR'). In general, R ₁ may be -Cl, -SO ₃ M or -NO ₂ ; a may be 1 or 2, or 1; M may be H, a metal cation, -NR' ₄ ⁺ , or a mixture thereof; R' The alkyl group may be optionally substituted with -H, or generally 1 to 20, or 1 to 10 carbon atoms, and the substituent may be a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; R ₂ It may be a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ hydrocarbon group, or a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ hydrocarbon carbonyl group (when R _{2 is} contained When more than 2 carbon atoms, the extended or extended hydrocarbon carbonyl group may be linear or branched), or a mixture thereof; R ₃ may be H or C _1-50 (or C _1-20 ) - optionally substituted hydrocarbyl group, Bonding a terminal oxygen atom to form a terminal ether group or a terminal ester group, and may or may not contain a polymerizable group such as a vinyl group, or a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a carbonyl group-containing hydrocarbon group which bonds to an oxygen atom of a polymer chain to form a terminal ester group or a terminal urethane group, and which may or may not contain a polymerizable group such as a vinyl group, and the substituent may be a halogen a base, an ether group, an ester group, or a mixture thereof; Pol can be a homopolymer of ethylene oxide a chain of copolymers of ethylene oxide or ethylene oxide, wherein the ethylene oxide comprises from 40% by weight to 99.99% by weight of the copolymer chain; u may be from 1 to 3, from 1 to 2, or 1; v may be 1 To 2; w may be 1 to 3, 1 to 2, or 1; when W = oxygen, sulfur or > NG, v = 1; G may be 1 to 200, 1 to 100, or 1 to 30 a hydrocarbon group of a carbon atom; v=2 when W=>NG; and Q may be a fused aromatic ring containing 4n+2 π electrons, wherein n=2 or more, generally 2 to 5, 2 to 4, 2 To 3, or 2, and the Q system is bonded to the quinone imine group in a manner to form a 5 or 6 membered quinone ring (generally a 6 membered ring).

In a specific embodiment, Pol may be an alkylene glycol having at least one member containing 3 or more carbon atoms (generally 3 to 24, 3 to 8, 3 to 4, or A copolymer of a group of three carbon atoms, typically propylene oxide, epoxy ethyl benzene, lactone, hydroxy-C _{2-20 -alkylene} carboxylic acid, and mixtures thereof. Pol based on a copolymer of ethylene oxide with a lactone, a hydroxy-C _{2-20 -alkylene} carboxylic acid, or a mixture thereof may be defined as a copolymer of poly(ethylene oxide) and poly(ester). Or a copolymer of poly(ether) and poly(ester).

Examples of alkylene glycols having 3 or more carbon atoms include propylene glycol, butylene glycol, or a mixture thereof (generally propylene glycol).

Examples of the hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acid include ricinoleic acid, 12-hydroxystearic acid, 6-hydroxycaproic acid, 5-hydroxyvaleric acid, 12-hydroxydodecanoic acid, 5- Hydroxydodecanoic acid, 5-hydroxydecanoic acid, 4-hydroxydecanoic acid, 10-hydroxyundecanoic acid, lactic acid, glycolic acid, or a mixture thereof.

Examples of lactones include β-propiolactone, γ-butyrolactone, optionally an alkyl-substituted ε-caprolactone, and optionally an alkyl-substituted δ-valerolactone. The alkyl substituent in ε-caprolactone and δ-valerolactone may be a C _1-6 -alkyl group or a C _1-4 -alkyl group, and may be linear or branched. Examples of suitable lactones are ε-caprolactone and its 7-methyl-, 2-methyl-, 3-methyl-, 5-methyl-, 6-methyl-, 4-methyl-, 5-tert-butyl-, 4,4,6-trimethyl-, and 4,6,6-trimethyl-homolog.

In a specific embodiment, a method of obtaining a polymer of the present invention (generally represented by formula (1)) comprises forming an amine-terminated polymer with a fusion of an aromatic diacid or anhydride, or another acid to form a derivative (eg, The ester, diamine, diacid dichloride is reacted to form a fused aromatic quinone having a polymer chain. The reaction to form the quinone imine can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, for example at least 100 ° C, or 150 ° C to 200 ° C.

In a specific embodiment, the polymer of the present invention (generally represented by formula (1)) can be obtained by the following method: Step (1): (i) amino acid, (ii) amino alcohol, ( Iii) an amino mercaptan, or (iv) a diamine or polyamine, which is fused with an aromatic diacid or anhydride, or other acid forming derivative (eg, diester, diamine, diacid dichloride), Minute An acid functionalized fusion aromatic quinone imine, a hydroxy functionalized fusion aromatic quinone imine, a thiol functionalized fusion aromatic quinone imine, or an amine functionalized fusion aromatic quinone imine is formed. The first step of the reaction can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, for example at least 100 ° C, or 150 ° C to 200 ° C; step (2): functionalizing the acid to aroma a quinone imine, a hydroxy functionalized fusion aromatic quinone imine, a thiol functionalized fusion aromatic quinone imine, or an amine functionalized fusion aromatic quinone imine formed by polymer chain or polymerized to form the polymer chain a monomer reaction, wherein the polymer chain is a homopolymer chain of ethylene oxide or a copolymer chain of ethylene oxide, and wherein the ethylene oxide comprises 40% by weight to 99.99 by weight of the copolymer chain percentage.

If the polymer chain has been previously formed before the reaction of the step (2), the product of the step (1) can be used as a polymerization terminator.

If the polymer chain is grown from one or more monomers in step (2), the product of step (1) can be used as a polymerization initiator.

When the product of the step (1) is further reacted in the alkoxylation reaction, the reaction temperature may be from 100 ° C to 200 ° C in the presence of a base catalyst such as potassium hydroxide or sodium hydroxide.

When the product of step (1) or step (2) is further reacted in the esterification reaction, the reaction temperature may be from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, optionally in the presence of an esterification catalyst.

The esterification catalyst can be any of those known in the art and includes tin(II) octoate, tetraalkyl titanate (e.g., tetrabutyl titanate), A zinc salt of an organic acid (such as zinc acetate), a zirconium salt of an aliphatic alcohol (such as zirconium isopropoxide), a toluenesulfonic acid or a strong organic acid (such as trifluoroacetic acid), or phosphoric acid.

The polymer of formula (1) can be blocked by a R ₃ group (instead of H). The R ₃ group can be derived from a carboxylic acid, an acid derivative, an alcohol, or an isocyanate. The acid, acid derivative, alcohol, and isocyanate are as described below. The reaction conditions for capping the polymer chain with an acid, an acid derivative, an alcohol, or an isocyanate to form a polymer of the present invention are those known in the art.

The process can be carried out in any inert atmosphere of the periodic table, but is typically nitrogen. The process can be carried out in the melt, with or without solvent. The solvent can be a non-polar solvent such as an aromatic or aliphatic compound, a polar organic solvent or water. Such solvents are known in the art.

In a specific embodiment, the present invention provides a composition comprising a particulate solid, an aqueous medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is as defined above Expressed by the formula (1). The composition can be abrasive, paint or ink.

In a specific embodiment, the present invention provides a composition comprising a particulate solid, a polar organic medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is as defined above The formula (1) is expressed. The composition can be abrasive, paint or ink.

In a specific embodiment, the present invention provides a composition comprising a particulate solid, an aqueous medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is as defined above Formula (1) represents and further contains a binder. In a specific implementation In one example, the binder can be a polyepoxide, a polyurethane, a polyamine, a poly(meth)acrylate, a polyester, a cellulose, or an alkyd.

In a specific embodiment, the present invention provides a composition comprising a particulate solid, a polar organic medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is as defined above Formula (1) represents and further contains a binder. In a particular embodiment, the binder can be cellulose (such as nitrocellulose), polyurethane, poly(meth)acrylate, polyester, or polyamine.

The invention also provides a composition comprising a particulate solid (typically a pigment or filler), an aqueous medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is as defined above The formula (1) is expressed. The composition can be abrasive, paint or ink.

The present invention also provides a composition comprising a particulate solid (typically a pigment or a filler), a polar organic medium, and a polymer chain having at least one fused aromatic fluorene imine pendant, wherein the polymer is The defined formula (1) is represented. The composition can be abrasive, paint or ink.

The particulate solids in the compositions of the invention disclosed herein may be pigments or fillers. In a particular embodiment, the pigment can be an organic pigment.

In a specific embodiment, the present invention provides a paint or ink comprising a particulate solid, an aqueous medium, a film forming resin, and a polymer of the present invention as disclosed herein.

In a specific embodiment, the present invention provides a paint or ink comprising a particulate solid, a polar organic medium, a film forming resin, And the polymers of the invention disclosed herein.

The ink can be inkjet ink, flexographic ink, lithographic ink, or gravure ink. The ink can be a radiation curable ink.

In a specific embodiment, the compositions disclosed herein further comprise a binder.

In a specific embodiment, the present invention provides a polymer chain comprising at least one fused aromatic quinone imine pendant (wherein the polymer is represented by formula (1) as defined above), an organic pigment, and The composition of the adhesive. The binder may be selected from the group consisting of cellulose, polyacrylic acid, polyester, polyether, polyurethane, alkyd, and polyamidamine. The composition can be used for printing method inks such as flexographic printing, or inkjet inks such as radiation hardenability, non-impacting, and control of droplets.

In the compositions disclosed herein, the amount of the polymer of the present invention may range from 0.1 weight percent to 79.6 weight percent, from 0.5 weight percent to 30 weight percent, or from 1 weight percent to 25 weight percent of the composition.

In a specific embodiment, the invention provides a polymer having at least one fused aromatic quinone imine pendant (wherein the polymer can be represented by formula (1) as defined above) in the compositions disclosed herein Used as a dispersant.

In a specific embodiment, the present invention provides a polymer having at least one fused aromatic quinone imine pendant (wherein the polymer is represented by formula (1) as defined above) as a dispersant in the ink composition Use. The ink composition can at least reduce particle size or reduce particle size distribution (generally reduced to an average of 150 nm or less), reducing haze, improving gloss, increasing jetting (especially when the composition is black), and being stable under ambient temperature storage and high temperature storage conditions.

Without being bound by theory, it is believed that the fusion aromatic quinone imine pendant can serve as a anchor between the polymer of the present invention and a particulate solid such as a pigment.

The present invention provides the compositions and uses disclosed above.

The polymer chain (Pol) may have a number average molecular weight of 100 to 10,000, 100 to 5,000, 300 to 3,000, or 400 to 2,500.

The number average molecular weight can be determined by GPC analysis on previously prepared polymer chains. The number average molecular weight of the polymer prepared in situ (ie, the polymer chain other than the quinone imine group) can be calculated by measuring the degree of polymerization (DP), the DP system and the monomer [M] and the initiator [I] (initiating The agent is proportional to the ratio of the intermediate derived from the fused aromatic anhydride and is calculated by the formula DP = [M] / [I]. It is possible to determine the degree of polymerization using an analysis using nuclear magnetic resonance (NMR), thus calculating the number average molecular weight of the polymer group or the polymer segment of the molecule.

Examples of the hydrocarbon group defined by R ² may include a methylene group, an exoethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a decyl group, a decyl group, a decyl group, or Branching isomers. In a particular embodiment, the hydrocarbyl group defined by R ² can be (-CH ₂ -) ₃ , -CH ₂ CH(CH ₃ )- or -CH ₂ CH ₂ -.

R ₂ may be derived from an amino alcohol, an amino thiol, an amino carboxylic acid, or an amine having 1 to 3, 1 to 2, or 1 -NH ₂ groups. The amine group may or may not contain an additional alkyl group.

Examples of the diamine include 1,2-diaminoethane, propane-1,3-diamine, butane-1,4-diamine, pentane-1,5-diamine, hex-1,6-diamine , 癸-1,12-diamine, or a mixture thereof.

Examples of polyamines include N-(2-aminoethyl)-1,3-propanediamine, 3,3'-imidopropylamine, spermidine, hydrazine (hexamethylene)triamine, three Ethylenetriamine, N,N'-indole (3-aminopropyl)-1,3-ethylenediamine, N,N'-indole (2-aminoethyl)-1,3-propanediamine , spermine, ginseng (2-aminoethyl)amine, tetraethyleneamine, triethylenetetramine, diethylenetriamine, or a mixture thereof.

The amino alcohol can be a C _2-20 -amino alcohol and may or may not contain more than one hydroxyl group and may or may not contain more than one amine group. The amino alcohol may be ethanolamine, 3-amino-1-propanol, 4-aminobutanol, 2-aminobutanol, 2-amino-2-methyl-1-propanol, 5-amine Base-1-pentanol, 5-amino-2-pentanol, 2-amino-3-methyl-1-butanol, 6-amino-1-hexanol, 2-amino-1-hexanol Alcohol, silk alcohol, 4-aminocyclohexanol, 2-(2-aminoethoxy)ethanol, 3-amino-1,2-propanediol, 2-amino-2-ethyl-1, 3-propanediol, cis (hydroxymethyl) aminomethane, cis (hydroxypropyl) aminomethane, 1,3-diamino-2-hydroxypropane, or a mixture thereof.

The amino mercaptan may be a C _2-20 -amino mercaptan and may or may not contain more than one thiol group and may or may not contain more than one amine group. The amino mercaptan may be 2-aminoethanethiol, 3-aminopropan-1-thiol, 4-aminobutan-1-thiol, 5-aminopentan-1-thiol, 6- Aminohexan-1-thiol, or a mixture thereof.

The term "hydrocarbon carbonyl" as used herein is a hydrocarbon group containing a carbonyl group. In general, the hydrocarbon carbonyl group may include -(CH ₂ ) ₅ -C(O)-, -(CH ₂ ) ₄ -C(O)-, -(CH ₂ ) ₃ -C(O)-, or - (CH ₂ ) ₂ -C(O)-.

The aminocarboxylic acid (or amino acid) can be an amine-C _{2-20 -alkylene} (alkenyl) carboxylic acid and may or may not contain more than one carboxylic acid group and may or may not contain more than one amine group. The aminocarboxylic acid may or may not contain other hetero atom-containing groups such as a hydroxyl group or a thiol group. The alkylene group may be linear or branched. The alkane (alkenyl) group of the aminocarboxylic acid contains no more than 12 carbon atoms. Specific examples include 11-aminoundecanoic acid, 12-aminododecanoic acid, 6-aminohexanoic acid, 4-aminobutyric acid, aspartic acid, glutamic acid, lysine, aspartate Acid, glutamic acid, threonine, serine, cysteine, beta-alanine, glycine, and sarcosine. It can use a mixture of aminocarboxylic acids.

The extended or extended hydrocarbon carbonyl group used herein may be linear or branched, and saturated or unsaturated.

Those skilled in the art can fully understand the technical characteristics of 4n+2 π electrons defined in Q by Hückel's law. In general, n can be equal to 2 (ie, the number of π electrons is 10) or 3 (ie, the number of π electrons is 14). In a specific embodiment, n can be equal to two.

Q can be based on naphthalene, anthracene, phenanthrene, or mixtures thereof. In a specific embodiment, Q can be based on naphthalene.

When the Q system is based on naphthalene, the polymer chain of the formula (1) may have a naphthoquinone imine group such as 1,2-naphthoquinone imido, 2,3-naphthylimine, 1,8-naphthoquinone. Imino groups, or mixtures thereof.

When the Q system is based on hydrazine, the polymer chain of the formula (1) may have a 1,2-indenylene group, a 2,3-indolylene group, a 1,9-fluorenylene group, or a mixture thereof. .

When the Q system is based on phenanthrene, the polymer chain of the formula (1) may have a 2,3-phenanthrene group, an 8,9-phenanthrene group, or a mixture thereof.

In general, the Q system is based on 1,8-naphthalic anhydride, 1,2-naphthalic anhydride, or a mixture thereof.

Q may be based on naphthalic anhydride such as 4-nitro-1,8-naphthalenedicarboxylic acid quinone imine or 3-nitro-1,8-naphthalenedicarboxylic acid quinone imine (when one R ₁ =NO ₂ ) , 4-chloro-1,8-naphthalene dicarboxylate imine (when R ₁ = Cl), 4-thioindol-1,8-naphthalene dicarboxylate imine or 3-thioindol-1, 8-naphthalene dicarboxylate (when one R ₁ =SO ₃ H), or a mixture thereof.

R ₁ may be an electron withdrawing group (such as a -NO ₂ group or a halogen group, generally -Cl), or a mixture thereof. When R ₁ is an electron withdrawing group, R ₁ may be a meta or para substitution with respect to the quinone imine group, or a mixture thereof. In a particular embodiment, R ₁ can be meta-substituted with respect to the quinone imine group. During the preparation of the polymer chain of the present invention, the fused aromatic quinone may be substituted at position 3- and/or 4- of Q (generally octadecyl 1,8-naphthalate).

R' may be an alkyl group having a linear or branched alkyl group or an optionally substituted alkyl group.

The alkyl group defined by R' includes methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, 2-ethylhexyl, decyl, decyl, undecyl, dodecyl, and ten. Tris, tetradecyl, fifteen, hexadecyl, heptyl, octadecyl, decyl, decyl, or mixtures thereof. In a particular embodiment, R' can be derived from an alkanol.

R ₃ may be H or C _1-50 (or C _1-20 ) - optionally substituted hydrocarbyl, which bonds to the terminal oxygen atom of the polymer chain to form a terminal ether group or terminal ester group, with or without a polymeric group, such as a vinyl group, or a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group) that bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal amine group The acid ester group may or may not contain a polymerizable group such as a vinyl group, and the substituent may be a halogen group, an ether group, an ester group, or a mixture thereof.

R ₃ may contain a group such as a (meth) acrylate, a styryl group, a vinyl ether, or an allyl ether, and a mixture thereof. Examples of R ₃ may be derived from (meth)acrylic acid and its esters, hydroxyalkyl (meth)acrylates and polyether derivatives thereof, such as hydroxyethyl acrylate or polyethylene glycol monoacrylate, (meth)acrylic acid isocyanate For example, ethyl isocyanate methacrylate.

R ₃ may be derived from an alcohol, a carboxylic acid, an acid derivative (such as an acid halide), an isocyanate, or a mixture thereof.

The term "alkylene" as used herein is intended to include alkyl and alkenyl groups.

The alcohol may be a C _1-20 alkane (alkenyl) alcohol, which may be linear or branched. Specific examples of the alcohol are methanol, ethanol, n-propanol, isopropanol, n-butanol, 1-methylpropanol, 2-methylpropanol, tert-butanol, n-pentanol, 1-methylbutyl Alcohol, 2-methylbutanol, 3-methylbutanol, 2,2-dimethylpropanol, n-hexanol, 1-methylpentanol, 2-methylpentanol, 3-methylpentanol, 4-methylpentanol, 1,1-dimethylbutanol, 2,2-dimethylbutanol, 3,3-dimethylbutanol, 1,2-dimethylbutanol, n-heptanol , 1-methylhexanol, 2-methylhexanol, 3-methylhexanol, 4-methylhexanol, 1,2-dimethylpentanol, 1,3-dimethylpentanol, 1 , 1-dimethylpentanol, 1,1,2,2-tetramethylpropanol, benzyl alcohol, n-octanol, 2-ethylhexanol, n-nonanol, 1-methyl octanol, 2- Methyl octanol, n-decyl alcohol, n-undecyl alcohol, 1-methyl decyl alcohol, 2-methyl decyl alcohol, n-dodecyl alcohol, 2,4-diethyl octanol, and the so-called Guerbet (Guerbet) alcohol, such as the trade name Isofol (e.g., Condea GmbH), or a mixture thereof. Designated examples of Guerbet alcohols are Isofol 12, 14T, 16, 18T, 18E, 20, 24, 28, 32, 32T, and 36.

The carboxylic acid may be a C _1-20 alkane (alkenyl) carboxylic acid group which may be linear or branched. Specific examples of the carboxylic acid are acetic acid, methoxyacetic acid, propionic acid, isobutyric acid, 2-methylbutyric acid, isovaleric acid, valeric acid, isohexanoic acid, caproic acid, heptanoic acid, octanoic acid, 2-ethyl Caproic acid, citric acid, dodecanoic acid, tetradecanoic acid, palmitic acid, octadecanoic acid, icosonic acid, or a mixture thereof.

The isocyanate may be an aromatic or C _2-20 alkylene (is) isocyanate which may be linear or branched. Specific examples thereof are 1-isocyanatoethane, 1-isocyanatopropane, 1-isocyanatobutane, 2-isocyanatobutane, 1-isocyanatopentane, 1- Isocyanate hexane, 1-isocyanatoheptane, 3-(isocyanatomethyl)heptane, 2-isocyanatoheptane, 2-isocyanato-2,4,4 -trimethylpentane, 1-isocyanatooctane, 2-isocyanatooctane, 1-isocyanatodecane, 2-isocyanatodecane, 1-isocyanatoyl Dioxane, 1-isocyanatotetradecane, 1-isocyanatoundecane, 1-isocyanatooctadecane, 1-isocyanatopentadecane, 1-isocyanatoyl Hexane, isocyanatocycloheptane, isocyanatocyclooctane, (isocyanatomethyl)cyclohexane, isocyanatocyclododecane, isocyanatocyclopentane, isocyanide Acid cyclohexane, 1-ethyl-4-(2-isocyanatoethyl)benzene, 1-isocyanato-4-methylbenzene, 1-tert-butyl-4-isocyanate Benzobenzene, 4-isocyanato-1,2-dimethylbenzene, 1-isocyanato-2,4-dimethylbenzene, 2-isocyanato-1,3,5-trimethyl Alkylbenzene, 1-ethyl-4-isocyanatobenzene, 1-isocyanato-4-isopropylbenzene, or a mixture thereof.

The acid halide may be a C _1-20 alkanoic acid chloride which may be linear or branched. Designated examples of the acid chloride are formazan chloride, butyl phosphonium chloride, 3,3-dimethylbutylphosphonium chloride, 3-methylbutylphosphonium chloride, 2-methylbutylphosphonium chloride, pentamidine chloride, helium chloride, Chlorhexidine, 2-ethylbutylphosphonium chloride, hydrazine chloride, 2-ethylhexyl chloride, octyl chloride, 2-methylamyl chloride, 3,5,5-trimethylhexyl chloride, hydrazine Chlorine, or a mixture thereof.

In a particular embodiment, R ₃ can comprise a polymerizable group, such as a vinyl group. R ₃ may contain a group such as a (meth) acrylate, a styryl group, a vinyl ether, or an allyl ether, and a mixture thereof. Examples of R ₃ may be derived from (meth)acrylic acid and its esters, hydroxyalkyl (meth)acrylates and polyether derivatives thereof, such as hydroxyethyl acrylate or polyethylene glycol monoacrylate, (meth)acrylic acid isocyanate For example, isocyanatoethyl methacrylate or an isocyanatostyryl derivative such as 4-isopropenyl-α,α-dimethylbenzyl isocyanate, or a mixture thereof.

W may be oxygen, sulfur, >NH, or >NG, wherein G represents a hydrocarbon group containing from 1 to 200, from 1 to 100, or from 1 to 30 carbon atoms. In general, W can be oxygen, sulfur or nitrogen. When W is sulfur, the structural group represented by the aromatic ring -R ₂ -W can be formed by reacting an aromatic ring anhydride with an amine thiol. When W is oxygen, the structural group represented by the aromatic ring -R ₂ -W can be formed by reacting an aromatic ring anhydride with an amino alcohol or an aminocarboxylic acid. When W is >NH (or >NG), the structural group represented by the aromatic ring -R ₂ -W can be formed by reacting an aromatic ring anhydride with a diamine or a polyamine.

It is possible to use all the mixtures, that is, the structural group represented by the aromatic ring -R ₂ -W can be obtained by using an aromatic ring anhydride as an amino alcohol, an aminocarboxylic acid, an aminothiol, a diamine, or A mixture of two, three, four, or all five of the polyamines is formed by reaction. The aromatic ring-R ₂ -W can be formed in a single vial reaction in the presence of all of the reactants. Alternatively, a blend of aromatic ring-R ₂ -W groups can be formed by mixing individual previously prepared quinazones.

The cation M can be a mono-, di- or trivalent metal. The metal cation can be, for example, an alkali metal, an alkaline earth metal or a transition metal. The metal cation can include lithium, sodium, potassium, calcium, magnesium, barium, zinc, or mixtures thereof.

The polymer chain Pol can be a homopolymer. The polymer chain Pol can be a copolymer. When Pol is a copolymer, the polymer chain can have a random or block structure. The polymer chain can have a random structure. The polymer chain can have a block architecture.

In a specific embodiment, the polymer chain (Pol) is based on poly(ether). The poly(ether) may be based on a polyethylene oxide homopolymer, or a polyethylene oxide with a polyalkylene glycol (typically a poly C ₃ -C ₄ -alkylene glycol) or a polyalkylene A mixture of alcohols (typically poly C ₈ -diols such as polyepoxyethylbenzene). In a specific embodiment, the poly(ether) polymer chain can be incorporated into the quinone imine structure represented by formula (2): Wherein each variable may be anywhere, respectively, Q is R ₁ may be bonded to the ring may be substituted on the substituent group, and R ₁ respectively, by at least one electron withdrawing group (e.g., -CN, -NO _2, -SO ₂ NR ' ₂ , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR') means, in general, R ₁ may be -Cl, -SO ₃ M or -NO ₂ ; a may be 1 or 2, or 1; W may be oxygen; M may be H, a metal cation, -NR' ₄ ⁺ , or a mixture thereof; R' The alkyl group may be optionally substituted with -H, or generally 1 to 20, or 1 to 10 carbon atoms, and the substituent may be a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; R ₂ It may be a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ hydrocarbon group, or a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ hydrocarbon carbonyl group (when R _{2 is} contained When more than 2 carbon atoms, the extended or extended hydrocarbon carbonyl group may be linear or branched), or a mixture thereof; R ₃ may be H or C _1-50 (or C _1-20 ) - optionally substituted hydrocarbyl group, the terminal oxygen atom bonded to the polymer chains to form a terminal or a terminal ether group, an ester group, and may or may not contain the polymerizable group, such as vinyl, or C _1-50 (or C _1-20) - carbonylation (ie, a hydrocarbon group containing a carbonyl group) which bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group such as a vinyl group, and the substituent may be Is a halogen group, an ether group, an ester group, or a mixture thereof; R ₄ may be H when Pol is a homopolymer, and R ₄ may be H when Pol is a copolymer (sufficient to provide 40 weight percent to 99.99 weight) a percentage of the oxirane group), and a mixture of at least one of a methyl group, an ethyl group and a phenyl group; u may be 1 to 3, 1 to 2, or 1; w may be 1 to 3, 1 to 2 Or 1; the condition is that when R ₂ is a hydrocarbyl group, u is 1 and w is 1; and m may be 1 to 110, 1 to 90, or 2 to 90.

In the formula (2), the integer m is such that the polymer chain may have a number average molecular weight of 100 to 10,000, 100 to 5,000, 300 to 3,000, or 400 to 2,500.

The quinone imine of formula (2) can be prepared by two different methods. The polymer chain of formula (2) may refer to a polyether.

The polyether may have from 0 to 60 weight percent, from 0 to 50 weight percent, from 0 to 30 weight percent, from 0 to 20 weight percent, from 0 to 15 weight percent, having three or more carbon atoms (typically 3 or 4 Or an alkylene oxide of 3 carbon atoms. The polyether can contain 40 to 100% by weight, 50 to 100% by weight, 70 to 100% by weight, 80 to 100% by weight, or 85 to 100% by weight of ethylene oxide.

The polyether can be, for example, a copolymer of ethylene oxide and propylene oxide. The polyether can be derived from: 0 to 60 weight percent propylene oxide, 40 to 100 weight percent ethylene oxide, 0 to 50 weight percent propylene oxide, and 50 to 100 weight percent ethylene oxide. 0 to 30 weight percent of propylene oxide, 70 to 100 weight percent of ethylene oxide, 0 to 20 weight percent of propylene oxide, 80 to 100 weight percent of ethylene oxide, or 0 to 15 weight A percentage of propylene oxide, and 85 to 100 weight percent of ethylene oxide.

For example, the polyether may contain 8 weight percent propylene oxide and 92 weight percent ethylene oxide, 14 weight percent propylene oxide and 86 weight percent ethylene oxide, or 29 weight percent propylene oxide and 71 Weight percent of ethylene oxide.

In a particular embodiment, the polymer chain can be (i) a polyethylene oxide homopolymer, or (ii) a poly(ether) of a copolymer of ethylene oxide and propylene oxide.

The first method comprises reacting a polyetheramine (typically a polyalkylene oxide monoalkyl ether monoamine) with an aromatic diacid or anhydride to form a product of formula (2).

The polyetheramine can form an alcohol-terminated polymer chain by reacting the monool initiator with only ethylene oxide or a mixture of ethylene oxide and propylene oxide, and then converting the alcohol-terminated polymer chain to an amine And prepared. The polyether amine may be a commercially available Surfonamine ^® Huntsman Corporation amine. Examples of amines Surfonamine ^® designated as L-100 (ethylene oxide propylene oxide mixing ratio 3/19), L-207 (a mixing ratio of propylene oxide to ethylene oxide of 10/32), L-200 (The ratio of propylene oxide to ethylene oxide is 3/41) and L-300 (the ratio of propylene oxide to ethylene oxide is 8/58). The numbers in parentheses are approximately repeating units of propylene oxide and ethylene oxide, respectively. The polyetheramine can be obtained by alkoxylation of an amine alcohol as described in U.S. Patent No. 5,879,445 (especially in column 2, line 50 to column 7, line 50).

The second method comprises reacting an amino acid with a fused aromatic diacid or anhydride to form an acid functional quinone imine; and monodisplacing the acid functionalized quinone imine with a polyalkylene glycol C _1-20 The (alkenyl) ether is esterified.

The polyalkylene glycol monosubstituted C _1-20 alkane (alkenyl) ether may be a homopolymer containing ethylene glycol, or a random or block copolymer, which will generally contain propylene glycol, butylene glycol and At least one of the ethyl benzenediols is copolymerized with ethylene glycol.

The polyalkylene glycol monosubstituted C _1-20 alkane (alkenyl) ether may be methoxy polyethylene glycol, ethoxy polyethylene glycol, propoxy polyethylene glycol, butoxy polyethylene A diol, a polyethylene glycol monoacrylate, an alkoxy group (polyethylene glycol-co-polypropylene glycol), or a mixture thereof.

In a specific embodiment, the polymer chain (Pol) is based on poly(ether). The poly(ether) can be based on a polyalkylene glycol (typically a poly C ₂ -C ₄ -alkylene glycol). In a particular embodiment, the poly(ether) polymer chain can be incorporated into the quinone imine structure represented by formula (3a): Wherein each variable may be anywhere, respectively, Q is R ₁ may be bonded to the ring may be substituted on the substituent group, and R ₁ respectively, by at least one electron withdrawing group (e.g., -CN, -NO _2, -SO ₂ NR ' ₂ , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR') means, in general, R ₁ may be -Cl, -SO ₃ M or -NO ₂ ; a may be 1 or 2, or 1; W may be sulfur, >NH, >NG, oxygen, or a mixture thereof (generally oxygen or >NG); M may be H, a metal cation, -NR' ₄ ⁺ , or a mixture thereof; R' may be -H, or an optionally substituted alkyl group generally having 1 to 20, or 1 to 10 carbon atoms, and The substituent may be a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; R ₂ may be a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ alkyl group, or a C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ extend a hydrocarbon carbonyl (when R ₂ contains more than 2 carbon atoms, the extended or extended hydrocarbon carbonyl may be linear or branched), or a mixture thereof; G may be contained 1-200, 1-100, or a hydrocarbon group having 1 to 30 carbon atoms; R ₃ may be H or C _1-50 (or C _1-20) - optionally substituted hydrocarbon group, which is bonded to the polymer chain The terminal oxygen atom to form an ether terminal group or a terminal ester group, and may or may not contain the polymerizable group, such as vinyl, or C _1-50 (or C _1-20) - hydrocarbon carbonyl group (i.e. the carbonyl-containing hydrocarbon group), It bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group, such as a vinyl group, and the substituent may be a halogen group, an ether group, an ester. a base, or a mixture thereof; R ₄ may be H when Pol is a homopolymer, and R ₄ may be H when Pol is a copolymer (sufficient to provide 40 to 99.99 weight percent of an oxirane group) And a mixture of at least one of a methyl group, an ethyl group and a phenyl group; u may be 1 to 3, 1 to 2, or 1; w may be 1 to 3, 1 to 2, or 1; and m may be 1 to 110, 1 to 90, or 2 to 90.

The polymers of the present invention can have a plurality of polymer chain-type attachment W groups. In a specific embodiment, the polymer chain (Pol) is based on poly(ether). The poly(ether) can be based on a polyalkylene glycol (typically a poly C ₂ -C ₄ -alkylene glycol). In a specific embodiment, the poly(ether) polymer chain can be incorporated into the quinone imine structure represented by formula (3b): Wherein W is N (formed when R ₂ of formula (1) is derived from a diamine or polyamine); R ₂ is a C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ alkyl; Is 2; and all other variables therein are as defined above.

In the formulae (3a) and (3b), the integer m is such that the polymer chain may have a number average molecular weight of from 100 to 10,000, from 100 to 5,000, from 300 to 3,000, or from 400 to 2,500.

The quinone imines of the formulae (3a) and (3b) can be prepared by different methods. The polymer chains of the formulae (3a) and (3b) may be referred to as polyethers.

The method of preparing the formula (3a) may comprise reacting an amino alcohol with a fused aromatic diacid or anhydride to form a hydroxy-functionalized fused aromatic quinone imine, and then functionalizing the hydroxy-functionalized aromatic quinone imine with at least one ring Ethylene oxide (such as ethylene oxide, or a mixture of ethylene oxide and propylene oxide, butylene oxide, epoxy ethylbenzene, or mixtures thereof), or carbonate (such as ethyl carbonate or carbonic acid) The propyl ester) reacts to form a polymer of the formula (3a) of the present invention wherein R ₃ is -H. The first step of the reaction (formation of the quinone imine) can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, for example at least 100 ° C or 150 ° C to 200 ° C, or at least 100 ° C or 150 ° C. Up to 250 ° C. The second step of the reaction to react the quinone imine with at least one ethylene oxide to form the product of formula (3a) is carried out in the presence of a base catalyst at a sufficiently elevated temperature known to those skilled in the art, for example at least 100 ° C, or 150 ° C to 200 ° C. In general, a temperature in the range of 150 ° C to 250 ° C can be used when carbonate is used.

The method for preparing the formula (3a) may further comprise reacting the amino mercaptan with a fusion aromatic diacid or anhydride to form a thiol-functionalized fusion aromatic quinone imine, and then functionalizing the thiol. An aromatic quinone imine with at least one ethylene oxide (such as only ethylene oxide, or combined with propylene oxide, butylene oxide, epoxy ethylbenzene, or a mixture thereof), or a carbonate (such as carbonic acid The ester or propyl carbonate is reacted to form a polymer of the formula (3a) of the present invention wherein R ₃ is -H.

The method for preparing the formula (3a) may further comprise reacting the amino acid with a fusion aromatic diacid or an anhydride to form an acid functionalized fusion aromatic quinone imine, and then functionalizing the aromatic ruthenium complex with the acid. The imine is at least one ethylene oxide (such as only ethylene oxide, or combined with propylene oxide, butylene oxide, epoxy ethylbenzene, or a mixture thereof), or a carbonate (such as ethyl or carbonic acid carbonate) The propyl ester is reacted to form a polymer of the formula (3a) of the present invention wherein R ₃ is -H.

The method for preparing the formulas (3a) and (3b) may also comprise reacting the diamine with a fusion aromatic diacid or anhydride to form an amine functionalized fusion aromatic quinone imine, and then the amine functional group. Blending aromatic quinone imine with at least one ethylene oxide (such as ethylene oxide only, or propylene oxide, butylene oxide, epoxy ethylbenzene, or mixtures thereof), or carbonate (such as carbonic acid) The ethyl ester or propyl carbonate is reacted to form a polymer of the formula (3a) of the present invention wherein R ₃ is -H.

In the above process, a hydroxy functionalized fusion aromatic quinone imine, a thiol functionalized fusion aromatic quinone imine, an acid functionalized fusion aromatic quinone imine, or an amine functionalized fusion aromatic quinone imine is epoxy The ethane reaction can be carried out at a temperature of from 100 ° C to 200 ° C in the presence of a base such as potassium hydroxide or sodium hydroxide.

In a specific embodiment, the poly(ether) polymer chain of the quinone imine structure represented by the formulas (3a) and (3b) wherein R ₃ is -H may be C _1-50 (or C _{1- 20} )-Hydrocarbon carbonyl (i.e., a hydrocarbon group containing a carbonyl group) is blocked. R ₃ may be derived from a carboxylic acid, an acid derivative such as an acid halide, an isocyanate, or a mixture thereof. a reaction condition in which a polymer chain is blocked to form a polymer of the formulae (3a) and (3b), wherein R ₃ may be a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group), It is a reaction known in the art.

In the formulae (2) and (3), the aqueous medium dispersant is formed when the polyether contains at least 60% by weight to 100% by weight of ethylene oxide.

In the formulae (2) and (3), a polar organic medium dispersant is formed when the polyether contains 40% by weight to 60% by weight of ethylene oxide.

In general, for aqueous medium dispersants, formulas (2) and (3) and polymers contain from 60% by weight to 100% by weight, from 70% by weight to 100% by weight, from 80% by weight to 100% by weight. Percent, or 100 weight percent ethylene oxide; and 0 weight percent to 40 weight percent, 0 weight percent to 30 weight percent, 0 weight percent to 20 weight percent, or 0 weight percent propylene oxide.

In a specific embodiment, the polymer chain (Pol) is based on a poly(ether)-co-poly(ester). The poly(ether)-co-poly(ester) can be based on a polyalkylene glycol (generally poly C ₂ -C ₄ -alkylene glycol) with a lactone, a hydroxy-C _{2-20 -alkylene} (alkene) a carboxylic acid, or a mixture thereof. In a specific embodiment, the poly(ether)-co-poly(ester) polymer chain can be incorporated into the quinone imine structure represented by formula (4a): Wherein each of the variables may each R ₁ may be used as Q in the ring may be substituted at any position on the bonded substituent, and R ₁ respectively, by at least one electron withdrawing group (e.g. _{-NO 2, -SO 2 NR '2} , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR') means that, in general, R ₁ can be -Cl, -SO ₃ M or -NO ₂ ; a may be 1 or 2, or 1; W may be sulfur, >NH, >NG, oxygen, or a mixture thereof (generally oxygen or >NG); M may be H, a metal cation, -NR' ₄ ⁺ , or a mixture thereof; R' may be -H, or an optionally substituted alkyl group generally having 1 to 20 or 1 to 10 carbon atoms, and the substituent It may be a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; R ₂ may be a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ alkyl group, or a C ₁ to C ₂₀ , C ₁ To C ₁₂ , or C ₁ to C _{6 to} extend a hydrocarbon carbonyl (when R ₂ contains more than 2 carbon atoms, the extended or extended hydrocarbon carbonyl may be linear or branched), or a mixture thereof; G may be from 1 to 200 , 1 to 100, or a hydrocarbon group having 1 to 30 carbon atoms; R ₃ may be H or C _1-50 (or C _1-20) - hydrocarbon carbonyl group (i.e. the carbonyl containing hydrocarbon group), which is bonded polymeric The oxygen atom of the chain forms a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group such as a vinyl group, and the substituent may be a halogen group, an ether group, an ester group, or a mixture thereof R ₄ may be H when Pol is a homopolymer, and R ₄ may be H (sufficient to provide an amount of 40 to 98.9% by weight of oxirane) when Pol is a copolymer, and a mixture of at least one of an ethyl group and a phenyl group; R ₅ may be a C _1-19 -hydrocarbyl group; u may be 1 to 3, 1 to 2, or 1; w may be 1 to 3, 1 to 2 Or 1; q may be 1 to 90; and m may be 1 to 90, with the condition that m is equal to or greater than q.

The polymers of the present invention can have a plurality of polymer chain-type attachment W groups. In a specific embodiment, the polymer chain (Pol) is based on a poly(ether)-co-poly(ester). The poly(ether)-co-poly(ester) can be based on a polyalkylene glycol (generally poly C ₂ -C ₄ -alkylene glycol) with a lactone, a hydroxy-C _{2-20 -alkylene} (alkene) a carboxylic acid, or a mixture thereof. In a particular embodiment, the poly(ether)-co-poly(ester) polymer chain can be incorporated into the quinone imine structure represented by formula (4b): Wherein W is N (formed when the R ₂ system of formula (1) is derived from a diamine or a polyamine); R ₂ may be a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ alkyl group ( When R ₂ contains more than 2 carbon atoms, the extended hydrocarbon group may be linear or branched), or a mixture thereof; v is 2; and all other variables therein are as defined above.

The polymer chain of formula (4a) or (4b) may have a number of 200 to 10,000, 300 to 5,000, 500 to 3,000, or 600 to 2,500. The average molecular weight. The polymer chain of formula (4a) or (4b) typically has a number average molecular weight of from 1000 to 2500.

The quinone imine of formula (4a) or (4b) can be prepared by various methods. The polymer chain of formula (4a) or (4b) may refer to a poly(ether)-co-poly(ester).

The process for preparing the formula (4a) comprises reacting a quinone imine of the formula (3a) wherein R ₃ is -H with a lactone, a hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acid, or a mixture thereof. The process can be carried out at a reaction temperature of from 50 ° C to 250 ° C or from 150 ° C to 200 ° C, optionally in the presence of an esterification catalyst.

The process for preparing the formula (4b) comprises reacting a quinone imine of the formula (3b) wherein R ₃ is -H with a lactone, a hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acid, or a mixture thereof. The process can be carried out at a reaction temperature of from 50 ° C to 250 ° C or from 150 ° C to 200 ° C, optionally in the presence of an esterification catalyst.

In a specific embodiment, the quinone imine represented by the formula (4a) or (4b) wherein R ₃ is a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group having a carbonyl group) may be borrowed. It is prepared by reacting a quinone imine of the formula (6a) or (6b) wherein R ₃ is -H, respectively, with a carboxylic acid, an acid derivative such as an acid halide, an isocyanate, or a mixture thereof. The reaction conditions for capping the polymer chain with an acid, acid derivative or isocyanate to form the polymer of the present invention are those known in the art.

Alternatively, the quinone imine of the formula (4a) or (4b) wherein R ₃ may be a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (i.e., a hydrocarbon group containing a carbonyl group) may be wherein R ₃ is - The ruthenium of formula (3a) or (3b) of H is prepared by reacting one or more acid-functional polyesters, respectively, at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, as appropriate. Implemented in the presence of catalyst. The acid functionalized polyester may be obtained from one or more hydroxy-C _{2-20 -alkylenecarboxylic} acids, lactones, or mixtures thereof, with C _1-50 (or C _1-20 )- as appropriate Polymerization of a hydrocarbon carbonyl, and is conveniently carried out at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, as appropriate in the presence of a catalyst, as disclosed in U.S. Patent No. 4,861,380.

In a particular embodiment, the polymer of the present invention can be represented by formula (5) (ie, the polymer can be a polyester-copolyether): Wherein each of the variables may each R ₁ may be used as Q in the ring may be substituted at any position on the bonded substituent, and R ₁ respectively, by at least one electron withdrawing group (e.g. _{-NO 2, -SO 2 NR '2} , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR') means that, in general, R ₁ can be -Cl, -SO ₃ M or -NO ₂ ; a may be 1 or 2, or 1; W may be oxygen; M may be H, a metal cation, -NR' ₄ ⁺ , or a mixture thereof; R' may be -H, or an optionally substituted alkyl group generally having 1 to 20, or 1 to 10 carbon atoms, and the substituent may be a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; R ₂ may be C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ extend a hydrocarbon carbonyl (when R ₂ contains more than 2 carbon atoms, the hydrocarbon carbonyl group may be linear or branched), or a mixture thereof; a hydrocarbon group having 1 to 200, 1 to 100, or 1 to 30 carbon atoms; R ₃ may be H or a C _1-50 (or C _1-20 )-optionally substituted hydrocarbon group, which is bonded polymerization The terminal oxygen atom of the chain forms a terminal ether group or a terminal ester group, and may or may not contain a polymerizable group such as a vinyl group, or a C _1-50 (or C _1-20 )-hydrocarbon a carbonyl group (ie, a hydrocarbon group containing a carbonyl group) which bonds to an oxygen atom of a polymer chain to form a terminal ester group or a terminal urethane group, and which may or may not contain a polymerizable group such as a vinyl group, and the substituent It may be a halogen group, an ether group, an ester group, or a mixture thereof; R ₄ may be H when Pol is a homopolymer, and R ₄ may be H when Pol is a copolymer (sufficient to provide 40 weight percent to 99.99) a mixture of at least one of a methyl group, a methyl group, and a phenyl group; R ₅ may be a C _1-19 -hydrocarbyl group; u may be 1 to 3, 1 to 2 Or 1; w may be 1 to 3, 1 to 2, or 1; q may be 1 to 90; and m may be 1 to 90, with the condition that m is equal to or greater than q.

The polymer chain of formula (5) may have a number average molecular weight of from 200 to 10,000, from 300 to 5,000, from 500 to 3,000, or from 1,000 to 2,500. The polymer chain of formula (5) generally has an average number of 1000 to 2500 Molecular weight.

The quinone imine of formula (5) can be prepared by a process comprising the steps of: (i) reacting an amino acid with a fused aromatic diacid or anhydride to form an acid functionalized fused aromatic quinone, and then the acid function The fused aromatic quinone imine is reacted with one or more hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acids, lactones, or mixtures thereof. The reaction of the acid functionalized fusion aromatic quinone with one or more hydroxy-C _{2-20 -alkylene} carboxylic acids, lactones, or mixtures thereof can range from 50 ° C to 250 ° C, or 150 ° C To a temperature of 200 ° C, optionally in the presence of an esterification catalyst; and (ii) optionally substituting the product of step (i) with a polyalkylene glycol in the presence of an esterification catalyst ) ether reaction.

Alternatively, the polymer of formula (5) can be obtained by reacting: (i) at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, optionally in the presence of an esterification catalyst, a polyalkylene glycol Monosubstituted alkylene (ene) ether, or poly(ethylene glycol-co-alkylene glycol) monosubstituted alkylene (ene) ether, with one or more hydroxy-C _{2-20 -alkylene} a carboxylic acid and/or a lactone to form a hydroxyl terminated polymer; and (ii) at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, optionally in the presence of an esterification catalyst The product of step (i) is acid-functionalized to fuse the aromatic quinone imine reaction.

Industrial Applications

The particulate solid present in the composition may be any inorganic or organic solid material that is substantially insoluble in the organic medium at the relevant temperature and/or insoluble in water, and which is desirably stabilized therein in a finely divided form. The The particulate solid may be in the form of a particulate material, fiber, platelet, or powder, often a foamed powder. In a specific embodiment, the particulate solid is a pigment.

The particulate solid (typically a pigment or filler) may have a diameter of from 10 nanometers to 10 micrometers, or from 10 nanometers to 1, 2, 3, or 5 micrometers, or 20 nanometers, as measured by light scattering measurements. Average particle size of 1, 2, 3, or 5 microns.

Examples of suitable solids are pigments, extenders, fillers, foaming agents, and flame retardants for paints and plastic materials; dyes, especially disperse dyes; optical brighteners and textile adjuvants; inks, toners Pigments; solids for oil and demulsification drilling; dust particles and solid particles in dry cleaning fluids; metals; ceramics, piezoelectric printing, refractory materials, abrasives, castings, capacitors, fuel cells, magnetic fluids, electrical conductivity Ink, magnetic recording media, water treatment, granular ceramic materials and magnetic materials for hydrocarbon soil rejuvenation; organic and inorganic nano-dispersed solids; metal for battery electrode, metal oxide and carbon; fiber for composite materials Such as wood, paper, glass, steel, carbon, and boron; and biocides, pesticides, and pharmaceuticals coated with a dispersion in an organic medium.

In a specific embodiment, the solid is an organic pigment obtained from any of the recognized classes of pigments, such as the Colour Index (1971) Third Edition and subsequent updates, and its supplements, entitled "Pigments." Examples of organic pigments are obtained from azo, diazo, trisazo, condensed azo, azo lake, naphthol pigment, anthanthrone, anthrapyrimidine, anthracene, benzo. Imidazolone, carbazole, diketopyrrolopyrrole, yellow ketone, indigo pigment, indanthrene, isodibenzanzanone, isoxanthin, isoindolinone, isoindole Porphyrin, isopurinone, metal complex pigment, cockroach, cockroach, perinone, pyranthrone, pyrazoloquinazolone, quinophthalone, quinoline yellow, sulfur Bismuth, triaryl carbocation pigments, triphendioxazine, xanthene, and indigo series, especially copper indigo and its nuclear halogenated derivatives, and acid, alkali and mordant dyes Lake. Although carbon black is strictly inorganic, its dispersing properties behave like organic pigments. In a specific embodiment, the organic pigments are indigo, especially copper indigo, monoazo, diazo, indanthrene, indole, quinophthalone, diketone Pyrrolylpyrroles, anthraquinones, and carbon blacks.

Examples of inorganic pigments include metal oxides such as titanium dioxide, rutile titanium dioxide and surface-coated titanium dioxide, titanium oxide of different colors (such as yellow and black), and oxidation of different colors (such as yellow, red, brown, and black). Iron, zinc oxide, zirconia, alumina, oxy metal compounds such as bismuth vanadate, cobalt aluminate, cobalt stannate, cobalt silicate, zinc chromate, and two or more of manganese, nickel, titanium, chromium Mixed metal oxides of ruthenium, magnesium, cobalt, iron, or aluminum, mozzarella blue, vermilion, ultramarine blue, zinc phosphate, zinc sulfide, calcium and zinc molybdate and chromate, metallic effect pigments such as aluminum flakes, Copper and copper/zinc alloys, pearlescent flakes such as lead carbonate and barium oxychloride.

Inorganic solids include extenders and fillers, such as ground and precipitated calcium carbonate, calcium sulfate, calcium oxide, calcium oxalate, calcium phosphate, calcium phosphonate, barium sulfate, barium carbonate, magnesium oxide, magnesium hydroxide, natural hydroxide Magnesium or brucite, precipitated magnesium hydroxide, magnesium carbonate, dolomite, aluminum trihydroxide, alumina or diaspore, calcium and magnesium citrate, aluminum silicate (including nano-clay), kaolin, Mongolia Soil removal (including bentonite, hectorite and saponite), ball soil (including natural, synthetic and expansive), mica, talc (including muscovite, phlogopite, lithium mica, and chlorite), chalk, synthesis and Precipitated vermiculite, fumed vermiculite, metal fiber and powder, zinc, aluminum, glass fiber, refractory fiber, carbon black (including single and multi-wall carbon nanotubes), strengthened and unreinforced carbon black, graphite, buckming Buckminsterfullerene, asphaltene, graphene, diamond, alumina, quartz, perlite, pegmatite, tannin, wood flour, wood chips (including softwood and hardwood), sawdust, powdered paper/fiber , cellulose fiber (such as kenaf, hemp, kenaf, linen, cotton, Lint, jute, ramie, rice husk or rough, raffia, cattail, coconut fiber, coir, oil palm fiber, kapok, banana leaf, caro, curaua, dragon tongue Henequen leaves, harakek leaves, manila hemp, bagasse, straw, bamboo, flour, MDF, etc., vermiculite, zeolite, hydrotalcite, fly ash from power plants, incineration Sewage sludge ash, pozzolanes, blast furnace slag, asbestos, chrysotile, anthophylite, blue asbestos, ash, magnesia, etc.; granular ceramic materials, such as alumina, zirconia, Titanium oxide, cerium oxide, cerium nitride, aluminum nitride, nitriding, cerium carbide, boron carbide, mixed tantalum nitride-aluminum, and metal titanate; granular magnetic material, such as magnetic oxide of transition metal, Often iron and chromium, such as γ-Fe ₂ O ₃ , Fe ₃ O ₄ , with cobalt-doped iron oxide, ferrous salts such as barium ferrite; and metal particles such as aluminum, iron, nickel, cobalt , copper, silver, gold, palladium, and platinum, and their alloys.

Other useful solid materials include flame retardants such as pentabromodiphenyl ether, octabromodiphenyl ether, decabromodiphenyl ether, hexabromocyclododecane, Ammonium polyphosphate, melamine, melamine cyanurate, cerium oxide and barium borate; biocide or industrial microbicide, such as Kirk-Othmer's Encyclopedia of Chemical Technology, Vol. 13, 1981, chapter title " Industrial Microbial Agents", as mentioned in Tables 2, 3, 4, 5, 6, 7, 8, and 9, and pesticides such as fungicide fufluafen, carbendazim, tetrachloro Iso-benzonitrile (chlorothalonil), and zinc-manganese (mancozeb).

In a specific embodiment, the polar liquid medium is water, but may contain up to 60 weight percent water soluble cosolvent. Examples of such cosolvents are diethylene glycol, glycerin, 2-pyrrolidone, N-methylpyrrolidone, cyclohexanol, caprolactone, caprolactam, penta-1,5-diol, 2 -(Butoxyethoxy)ethanol, diethanol sulfide, ethylene glycol, including mixtures thereof.

The abrasive or dispersion can be used to prepare aqueous paints and inks by mixing other amounts of water-compatible resin and/or water, with other ingredients conventionally incorporated into water-based paints and inks, such as preservatives, stabilizers. Agent, defoamer, water miscible cosolvent, and coalescent.

The water compatible resin can be any water soluble or water insoluble polymer used in the aqueous coatings industry. Examples of polymers which are often used as binder resins in the latex or water reducing coatings are acrylic, vinyl esters, polyurethanes, polyesters, epoxy groups, and alkyds.

The organic medium present in the composition of the present invention is a plastic material in one embodiment, and an organic liquid in another embodiment. The organic liquid can be a polar organic liquid. The term "polar" as used in relation to organic liquids refers to organic liquids that form medium to strong bonds, such as Crowley et al., Journal of Paint Technology, Vol. 38. 1966, page 269, entitled "A Three Dimensional Approach to Solubility." This organic liquid typically has a hydrogen bond number of 5 or more, as defined in the above article.

Examples of suitable polar organic liquids are amines, ethers (especially lower alkyl ethers), organic acids, esters, ketones, glycols, glycol ethers, glycol esters, alcohols, And guanamines. A number of designated examples of this medium-strong hydrogen-bonded liquid are shown in the book Ibert Mellan, entitled "Compatibility and Solubility" (published by Noyes Development Corporation in 1968), Table 2.14 on pages 39-40, and these liquids are The term polar organic liquid is used herein.

In a particular embodiment, the polar organic liquid is a dialkyl ketone, an alkyl ester of a paraffinic carboxylic acid and an alkanol, especially wherein the liquid contains up to and includes a total of 6 carbon atoms. Examples of the polar organic liquid include dialkyl and cycloalkyl ketones such as acetone, methyl ethyl ketone, diethyl ketone, diisopropyl ketone, methyl isobutyl ketone, diisobutyl ketone, Methyl isoamyl ketone, methyl n-amyl ketone, and cyclohexanone; alkyl esters such as methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, ethyl formate, methyl propionate , methoxypropyl acetate, and ethyl butyrate; glycols, glycol esters and ethers, such as ethylene glycol, 2-ethoxyethanol, 3-methoxypropyl propanol, 3- Ethoxypropyl propanol, 2-butoxyethyl acetate, 3-methoxypropyl acetate, 3-ethoxypropyl acetate, 2-ethoxyethyl acetate; alkanols, such as Methanol, ethanol, n-propanol, isopropanol, n-butanol, and isobutanol (also known as 2-methylpropanol), terpineol and dialkyl and cycloalkyl ethers, such as diethyl Ether and tetrahydrofuran. In a specific embodiment, the solvent is an alkanol, a paraffinic carboxylic acid, and a paraffinic carboxylic acid. Esters. In a particular embodiment, the invention is suitable for organic liquids that are substantially insoluble in aqueous media. Furthermore, it will be understood by those skilled in the art that small amounts of aqueous media (eg, glycols, glycol ethers, glycol esters, and alcohols) may be present in the organic liquid, provided that all of the organic liquid is substantially insoluble in the organic liquid. In aqueous media.

Examples of organic liquids which can be used as polar organic liquids are film forming resins, such as those suitable for use in the preparation of inks, paints, and for use in various applications such as inks and paints. Examples of such resins include polyamide-based, such as Versamid ^{TM (TM)} and Wolfamid, and cellulose ethers, such as ethyl cellulose and ethyl hydroxyethyl cellulose, nitrocellulose, and cellulose acetate butyrate Ester resins, including mixtures thereof. Examples of the paint resin include short oil alkyd / melamine - formaldehyde, polyester / melamine - formaldehyde, thermosetting acrylic / melamine - formaldehyde, long oil alkyd, medium oil alkyd, short oil alkyd, polyether polyol, and Dielectric resins such as acrylic and urea/aldehyde.

The organic liquid may be a polyol, that is, an organic liquid having two or more hydroxyl groups. In a particular embodiment, the polyol comprises an alpha-omega diol or an alpha-omega diol ethoxylate.

In a specific embodiment, the organic liquid comprises at least 0.1 weight percent, or 1 weight percent or more, of a polar organic liquid, based on total organic liquid. The organic liquid further comprises water as the case may be. In a particular embodiment, the organic liquid is anhydrous (typically less than 2 weight percent water, less than 1 weight percent water, less than 0.5 weight percent water, or less than 0.1 weight percent water).

The plastic material can be a thermosetting resin. Can be used in the present invention The thermosetting resin includes a resin that undergoes a chemical reaction when heated, catalyzed, or subjected to ultraviolet light, laser light, infrared light, cationic, electron beam, or microwave radiation and becomes quite insoluble. Typical reactions for thermosetting resins include oxidation of unsaturated double bonds, reactions involving epoxy groups/amines, epoxy/carbonyl groups, epoxy groups/hydroxy groups, reaction of epoxy groups with Lewis acid or Lewis base, and polyisocyanates. /Hydroxyl group, amine resin / hydroxyl moiety, free radical reaction of polyacrylate, cationic polymerization of epoxy resin and vinyl ether, and condensation of sterol. Examples of the unsaturated resin include polyester resins produced by the reaction of one or more diacids or anhydrides with one or more diols. This resin is usually supplied as a mixture having a reactive monomer such as styrene or vinyl toluene, and is often referred to as a phthalic acid type resin and an isophthalic acid type resin. Further examples include resins in which dicyclopentadiene (DCPD) is used as a co-reactant in the polyester chain. Further examples also include the reaction product of bisphenol A diglycidyl ether with an unsaturated carboxylic acid such as methacrylic acid, which in turn is supplied as a solution in styrene, often referred to as a vinyl ester resin.

In a specific embodiment, the thermosetting composite or thermosetting plastic can be polyester, polyvinyl acetate, polyester resin in styrene, polystyrene, or a mixture thereof.

Polymers having hydroxyl functionality (often polyols) are widely used in thermoset systems to crosslink with amine based resins or polyisocyanates. The polyol includes an acrylic polyol, an alkyd polyol, a polyester polyol, a polyether polyol, and a polyurethane urethane. Typical amine based resins include melamine formaldehyde resins, benzoguanamine formaldehyde resins, urea formaldehyde resins, and acetylene urea formaldehyde resins. Polyisocyanate has 2 The above isocyanate-based resin includes a monomeric aliphatic diisocyanate, a monomeric aromatic diisocyanate, and a polymer thereof. Typical aliphatic diisocyanates include hexamethylene diisocyanate, isophorone diisocyanate, and hydrogenated diphenylmethane diisocyanate. Typical aromatic isocyanates include toluene diisocyanate and diphenylmethane diisocyanate.

If necessary, the composition of the present invention may contain other components such as a resin (which does not constitute an organic medium), a binder, a cosolvent, a crosslinking agent, a fluidizing agent, a wetting agent, an anti-settling agent, a plasticizer. , surfactant, dispersant other than the compound of the invention, humectant, antifoaming agent, anti-cracking agent, rheology regulator, thermal stabilizer, light stabilizer, UV absorber, antioxidant, leveling agent, gloss Conditioning agents, biocides, and preservatives.

If necessary, the composition containing the thermosetting plastic material may contain other components such as a dispersing agent other than the compound of the present invention, a foaming agent, a flame retardant, a process aid, a surfactant, a heat stabilizer, a UV absorber, Antioxidants, perfumes, mold release aids, antistatic agents, microbicides, biocides, coupling agents, lubricants (external and internal), air release agents, and viscosity inhibitors.

The composition typically contains from 1 to 95 weight percent of particulate solids, depending on the nature of the solid and the relative density of the solid and polar organic liquid. For example, based on the total weight of the composition, the solid is a composition of an organic material (such as an organic pigment) containing 15 to 60% by weight of solids in a specific embodiment, wherein the solid is an inorganic material (such as an inorganic pigment, The composition of the filler or extender) contains from 40 to 90 weight percent solids in one embodiment.

The composition containing an organic liquid can be prepared by any conventional method known for preparing a dispersion. Therefore, the solid, organic medium and dispersant can be mixed in any order, and then the mixture is mechanically treated to reduce the solid particles to a suitable size, for example, by high-speed mixing, ball milling, basket milling, bead milling, stone grinding, sanding, machine Grinding, two-roll or three-roll grinding, plastic grinding until a dispersion is formed. Alternatively, the solid may be treated separately or mixed with an organic medium or a dispersing agent to reduce its particle size, and then the other ingredients are added and the mixture is agitated to provide a composition. The composition can also be produced by grinding or grinding a dry solid with a dispersant, then adding a liquid medium during the pigment rinse, or mixing the solid with a dispersant in a liquid medium.

The composition containing the plastic material can be prepared by any conventional method known for preparing a thermoplastic compound. Thus, the solid, thermoplastic polymer and dispersant can be mixed in any order, and then the mixture is mechanically treated to reduce the solid particles to a suitable size, such as Banbury blending, ribbon blending, and two-screw extrusion. , two-roll grinding, compounding in a Buss co-kneader or similar equipment.

The composition of the present invention is particularly suitable for liquid dispersions. In a specific embodiment, the dispersion composition comprises: (a) 0.5 to 80 parts of the particulate solid; (b) 0.1 to 79.6 parts of the polymer of the formula (1); and (c) 19.9 to 99.4 parts. The organic liquid and/or water; wherein all of the relative parts are by weight, and the amount (a) + (b) + (c) = 100.

In a specific embodiment, component a) comprises from 0.5 to 30 parts of pigment, and the dispersion can be used as (liquid) ink, paint and mill material.

If a composition comprising a particulate solid and a dry form of a dispersant of formula (1) is desired, the organic liquid is generally volatile and can be easily removed from the particulate solid by simple means of separation such as evaporation. In a specific embodiment, the composition comprises an organic liquid.

If the dry composition consists essentially of a dispersant of formula (1) and a particulate solid, it generally contains at least 0.2%, at least 0.5%, or at least 1.0% by weight of the particulate solid (1) ) a dispersant. In a specific embodiment, the dry composition contains no more than 100, no more than 50, no more than 20, or no more than 10 weight percent of the dispersant of formula (1) by weight of the particulate solid.

As disclosed previously, the compositions of the present invention are suitable for use in the preparation of abrasives wherein the particulate solid is ground in an organic liquid in the presence of a compound of formula (1).

Accordingly, still a further aspect of the present invention provides an abrasive comprising a particulate solid, an organic liquid, and a polymer of formula (1).

Generally, the abrasive contains from 20 to 70 weight percent of particulate solids based on the total weight of the abrasive. In a specific embodiment, the particulate solid is no less than 10 or less than 20 weight percent of the abrasive. The abrasive may optionally contain a binder which is added before or after grinding.

In one embodiment, the binder is a polymeric material that bonds the composition as the organic liquid evaporates.

Adhesives are polymeric materials including natural and synthetic materials. In a specific embodiment, the binder comprises poly(meth) acrylate, poly Styrene, polyester, polyurethane, alkyd, polysaccharides (such as cellulose, nitrocellulose), and natural proteins (such as casein). The binder can be nitrocellulose. In a specific embodiment, the binder is present in the composition in an amount of more than 100%, more than 200%, more than 300%, or more than 400% by weight of the particulate solid.

The amount of binder selected for use in the abrasive can vary over a wide range of limits, but is generally not less than 10 of the continuous/liquid phase of the abrasive, and often no less than 20 weight percent. In one embodiment, the amount of binder is no greater than 50, or no greater than 40 weight percent of the continuous/liquid phase of the abrasive.

The amount of dispersant in the abrasive depends on the amount of particulate solids, but is generally from 0.5 to 5 weight percent of the abrasive.

The dispersions and abrasives produced from the compositions of the present invention are particularly suitable for use in non-aqueous and solvent-free formulations in which energy curable systems (ultraviolet light, laser light, infrared light, cationic, electron beam, microwave) are used, and The formulation contains monomers, oligomers, and the like, or a combination thereof. It is particularly suitable for use in coatings such as paints, varnishes, inks, other coating materials, and plastics. Suitable examples include low-, medium-, and high-solid paints, general industrial paints, including baking varnishes, two-component and metal-coated paints, such as coil and can coatings, powder coatings, UV-curable coatings, wood varnishes; Ink, such as flexographic, gravure, lithographic, lithography, letterpress or letterpress, screen printing, and printing inks for packaging printing, non-impact inks, such as inkjet inks, including continuous inkjet and controlled droplet inkjet (including thermal, piezoelectric and electrostatic), phase change inks and hot melt wax inks, inks for inkjet printers, and printing varnishes, such as overprint varnishes; polyols and plastisol dispersions; non-aqueous ceramics Especially the scraper Molding, gel forming, doctor blade, extrusion and spray molding, further examples are dry ceramic powders for isostatic pressing; composites such as sheet molding and agglomerated molding compounds, resin transfer molding, pultrusion, Manual lamination, spray lamination, mold molding; construction materials (such as mold resin), cosmetics, personal care (such as nail polish), sunscreen lotion, adhesive, toner (such as liquid toner), plastic Materials and electronic materials (such as display coatings for color filter systems including organic light-emitting diode (OLED) devices, liquid crystal displays and electrophoretic displays), glass coatings (including fiber coatings, reflective coatings or anti-reflective coatings) Reflective coatings), conductive and magnetic inks and coatings. It can be used for surface modification of pigments and fillers to improve the dispersion of dry powders for the above applications. Further examples of coating materials are shown in Bodo Muller, Ulrich Poth, Lackformulierung, Lehrbuch fr Ausbildung und Praxis with Lackrezeptur, Vincentz Verlag, Hanover (2003), and Strahlenhartung, Vincentz Verlag, Hanover (1996) by P. G. Garrat. Examples of printing ink formulations are shown in E. W. Flick, Printing Ink and Overprint Varnish Formulations-Recent Developments, Noyes Publications, Park Ridge NJ, (1990), and subsequent editions.

Dispersions and abrasives prepared from the compositions of the present invention can also be used in contact and non-contact (controlled droplet) aqueous printing processes such as aqueous flexographic printing, aqueous inkjet, aqueous UV inkjet.

In a particular embodiment, the compositions of the present invention further comprise one or more additional known dispersants.

The following examples provide an illustration of the invention. These examples are non It is exclusive and is not intended to limit the scope of the invention.

[Examples]

Comparative Example 1 (CE1): In accordance with U.S. Patent Publication 2005/0120911 of Example No. 1 Preparation of a dispersant, in addition to a substituted Surfonamine ^TM L207 XJT-507. 1,2,4-benzenetricarboxylic anhydride (12.97 parts) was added to a stirred polyetheramine (150 parts of Surfonamine® L207 from Huntsman). The reaction was stirred at 110 ° C for 3 hours under nitrogen and then at 150 ° C for 8 hours. IR is consistent with quinone imine formation and has an acid number of 25.6 mg KOH/g.

Comparative Example 2 (CE2) : 1,8-naphthalic anhydride (14.46 parts) was added to a stirred polyetheramine (150 parts of Surfonamine® L207 from Huntsman (71 weight percent ethylene oxide, with 29 weight) Percentage of propylene oxide. The reaction was stirred under nitrogen at 100 ° C for 8 hours and then at 150 ° C for 12 hours. IR was consistent with quinone imine formation and the final product had an acid number of 5.46 mg KOH / gram. A dispersant prepared as disclosed in U.S. Patent No. 6,440,207.

Example 1 : 3-Nitro-1,8-naphthalic anhydride (14.46 parts) was added to a stirred polyetheramine (150 parts of Surfonamine® L207 from Huntsman). The reaction was stirred at 90 ° C for 5 hours under nitrogen and then at 150 ° C for 6 hours. IR is consistent with quinone imine formation and the final product acid number is 1.61 mg KOH/g.

Example 2 : 3-Nitro-1,8-naphthalic anhydride (18.36 parts) was added to a stirred polyetheramine (81.64 parts of Surfonamine® L100 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then at 175 ° C for 3 hours. IR is consistent with quinone imine formation and the final product acid number is 0.82 mg KOH/g.

Example 3 : 3-Nitro-1,8-naphthalic anhydride (16.2 parts) was added to a stirred polyetheramine (133.76 parts of Surfonamine® L200 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then at 175 ° C for 3 hours. IR is consistent with quinone imine formation and the final product acid number is 0.78 mg KOH/g.

Dispersion Test 1

A dispersion containing the polymers of Examples 1 to 3, CE1 and CE2, respectively, was prepared. Each dispersion contained polymer (15 parts), water (97.05 parts), propylene glycol (7.5 parts), antifoaming agent (0.45 parts of DF1396 from eChem), and pigment red 122 (30 parts, available from Clariant). the Inkjet Magenta E02 VP2621) was charged Dispermat ^TM F1 bucket. It was then added under stirring of glass beads (190 parts), and the mixture was milled at 2000rpm in a Dispermat ^TM F1 mill for 60 minutes. The resulting abrasive is filtered to remove the glass beads. To the abrasive (120 parts), water (38 parts), propylene glycol (2 parts), and an antifoaming agent (0.12 parts of DF1396 from eChem) were added. The resulting dispersion was in the WAB ^TM mill (Willy A.Bachofen Research lab of the mill) using 0.1 mm zirconium beads and milled at 20 ℃ at 4000rpm for 1 hour at the grinding chamber. The dispersion was allowed to stand at 50 ° C for a period of 3 weeks. Then using Nanotrac ^TM particle size analyzer. The particle size (PS) measured for each dispersion is shown below. In general, a dispersion having a lower particle size after 3 weeks gave better results. The result is:

Note: D.N.M. is not ground. Therefore, the properties of the dispersion cannot be measured.

PS ¹ is the original D50 (nano)

PS ² is the original D90 (nano)

PS ³ is 1 week (50 ° C) after D50 (nano)

PS ⁴ is 1 week (50 ° C) after D90 (nano)

PS ⁵ is 3 weeks (50 ° C) after D50 (nano)

PS ⁶ is 3 weeks (50 ° C) after D90 (nano)

CE1 gels during grinding without making a fluid dispersion. CE2 produces an unstable dispersion. The dispersion containing the polymer of the present invention remains as a fluid and has the average particle size required for ink jet printing applications. The dispersion containing the polymer of the present invention remains stable over time.

Intermediate A : 3-Nitro-1,8-naphthalic anhydride (12.5 parts) was dissolved in concentrated sulfuric acid (95.5 parts) and cooled to 0 °C. A blend of concentrated sulfuric acid (23.9 parts) and concentrated nitric acid (4.4 parts) was added at 0 ° C for 45 minutes and then stirred at 21 ° C for 17 hours under nitrogen. The reaction mixture was poured onto ice and then filtered. The resulting precipitate was washed with water and recrystallized from acetic acid. The product formed was a brown solid with a nitrogen content of 7.8% and the NMR was consistent with dinitration.

Intermediate B : 1,2-Naphthalic anhydride (6.3 parts) was dissolved in concentrated sulfuric acid (46.7 parts) and cooled to 0 °C. A blend of concentrated sulfuric acid (11.96 parts) and concentrated nitric acid (2.2 parts) was added at 0 ° C for 1 hour, and then stirred at 21 ° C for 17 hours under nitrogen. The reaction mixture was poured onto ice and then filtered. The resulting precipitate was washed with water and recrystallized from acetic acid. The product formed was a yellow solid with a nitrogen content of 4.1% and the NMR was consistent with mononitration.

Intermediate C : 2,3-naphthalic anhydride (6.3 parts) was dissolved in concentrated sulfuric acid (46.7 parts) and cooled to 0 °C. A blend of concentrated sulfuric acid (11.96 parts) and HNO ₃ (2.2 parts) was added at 0 ° C for 1 hour, and then stirred at 21 ° C for 17 hours under nitrogen. The reaction mixture was poured onto ice and then filtered. The resulting precipitate was washed with water and recrystallized from acetic acid. The product formed was a yellow solid with a nitrogen content of 3.6% and the NMR was consistent with mononitration.

Intermediate D: 1,8-naphthalic anhydride (10 parts) was added concentrated sulfuric acid (30 parts of 30% free SO _3, and 30 parts of 20% free SO ₃₎ over at 0 ℃ 25 minutes. The mixture was heated at 95 ° C for 1 hour and then poured onto ice water (70 parts). The resulting precipitate was filtered and washed with glacial acetic acid (40 parts), hexane (40 parts), and hydrochloric acid (40 parts), and then dried. The resulting product was a grey solid with a sulfur content of 10.3% and the NMR was consistent with monosulfonation.

Intermediate E : 2-(2-Aminoethoxy)ethanol (30.27 parts) was added to 3-nitro-1,8-naphthalic anhydride (70.00 parts) and stirred at 180 ° C for 6 hours under nitrogen. . IR is consistent with quinone imine formation and the final product acid number is 0.57 mg KOH/g.

Example 4 : Intermediate A (3.5 parts) was added to a stirred polyetheramine (26.47 parts, Surfonamine® L207 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then at 180 ° C for 2 hours. IR is consistent with quinone imine formation and the final product acid number is 0.85 mg KOH/g.

Example 5 : 4-Chloro-1,8-naphthalic anhydride (4.85 parts) was added to a stirred polyetheramine (45.15 parts of Surfonamine® L207 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then at 180 ° C for 2 hours. IR is consistent with quinone imine formation and the final product acid number is 3.63 mg KOH/g.

Example 6 : 4-Nitro-1,8-naphthalic anhydride (2.25 parts) was added to a stirred polyetheramine (22.75 parts, obtained from Surfonamine® L207 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then at 180 ° C for 2 hours. IR is consistent with quinone imine formation and the final product acid number is 6.75 mg KOH/g.

Example 7 : 4-Bromo-1,8-naphthalic anhydride (2.27 parts) was added to a stirred polyetheramine (17.73 parts, obtained from Surfonamine® L207 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then at 180 ° C for 2 hours. IR is consistent with quinone imine formation and the final product acid number is 5.25 mg KOH/g.

Example 8 : Intermediate B (1.45 parts) was added to a stirred polyetheramine (14.68 parts, Surfonamine® L207 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then at 180 ° C for 5 hours. IR is consistent with quinone imine formation and the final product acid number is 2.49 mg KOH/g.

Example 9 : Intermediate C (1.45 parts) was added to a stirred polyetheramine (14.68 parts, obtained from Surfonamine® L207 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then at 180 ° C for 5 hours. IR is consistent with quinone imine formation and the final product acid number is 1.38 mg KOH/g.

Example 10 : Triethylamine (0.405 parts) was added to a stirred solution of Intermediate D (10.92 parts) dissolved in acetone (50 parts). The reaction was stirred at room temperature for 30 minutes and then a polyetheramine (8.50 parts from Surfonamine® L207 from Huntsman) was added. The reaction mixture was stirred at 70 ° C for 1 hour to remove acetone by distillation. The mixture was then heated at 100 ° C for 1 hour and at 175 ° C for 2 hours. IR is consistent with quinone imine formation and the final product acid number is 23.5 mg KOH/g.

Intermediate E (101.57 parts) and potassium hydroxide (3.0 parts) were stirred in a pressure vessel under nitrogen and heated to 155 °C. Ethylene oxide (314 parts) was added over 52 hours and heated at 155 ° C for another 16 hours. The resulting product was a brown liquid, which was determined by GPC (THF solvent, polystyrene standard), and had a molecular weight of Mn=700 and Mw=1342.

Dispersion Test 2

Examples 4 to 9 (0.9 parts) were dissolved in water (7.6 parts) having an antifoaming agent (0.01 part, BYK024 from Byk Chemie) to prepare a dispersion. 3 mm glass beads (17.0 parts) and Pigment Violet 19 (1.5 parts, Inkjet Magenta E5BO2 from Clariant) were added and the contents were ground for 16 hours with horizontal shake. The resulting fluid dispersion (2.5 parts) was dissolved in an ink solution (10 parts). The ink solution was prepared by 2-pyrrolidone (2.33 parts), 1,5-pentanediol (5.83 parts), glycerin (11.66 parts), and a wetting agent (0.58 parts, Tego® Wet from Evonik). 10%) was prepared by adding distilled water (74.6 parts). The particle size (PS) measured for each dispersion is shown below:

Dispersion Test 3

The dispersions were prepared by dissolving Examples 1, 2, 10, and 11 (0.9 parts) in water (7.6 parts). 3 mm glass beads (17.0 parts) and pigment black (1.5 parts, Nipex® Black from Evonik) were added and the contents were ground with a horizontal shaker. The particle size (PS) of each dispersion was measured. All dispersions achieved low particle size.

Overall, the results show that the polymer of the present invention at least increases the loading of the particulate solids, forms an improved dispersion, improves brightness, and produces a composition having reduced viscosity in an organic medium.

In the context of the present invention, the term "hydrocarbyl" or "hydrocarbon" "Base" means a group in which a carbon atom directly attaches to the remainder of the molecule and has a hydrocarbon or predominantly hydrocarbon character. This group includes the following: (1) a pure hydrocarbon group; that is, an aliphatic group (for example, an alkyl group or an alkenyl group), an alicyclic group (for example, a cycloalkyl group or a cycloalkenyl group), an aromatic group, an aliphatic group and an alicyclic group, and an aromatic group. An aromatic substituted aliphatic group and an alicyclic group, etc., and a cyclic group in which the ring is completely passed through other parts of the molecule (i.e., any two of the substituents shown may together form an alicyclic group). This base is known to those skilled in the art. Examples include methyl, ethyl, octyl, decyl, octadecyl, cyclohexyl, phenyl, and the like. (2) a substituted hydrocarbyl group; that is, a group containing a non-hydrocarbon substituent which does not change the characteristics of the main hydrocarbon. Suitable substituents will be understood by those skilled in the art. Examples include hydroxy, nitro, cyano, alkoxy, decyl and the like. (3) a hetero group; that is, although the main feature is a hydrocarbon, a chain or ring composed of carbon atoms contains a group of atoms other than carbon. Suitable heteroatoms are well known to those skilled in the art and include, for example, nitrogen, oxygen and sulfur.

As described below, the number average molecular weight of the polymer of the present invention is determined by a known method, such as GPC analysis, which uses a polystyrene standard for all polymer chains other than ethylene oxide. The number average molecular weight of the polymer chain containing ethylene oxide was determined using GPC (THF solvent, PEG standard).

Each of the above documents is incorporated herein by reference. Except in the examples or clearly indicated, it should be understood that the quantities of all specified materials, reaction conditions, molecular weights, number of carbon atoms, and the like in the description are modified by the word "about". Unless otherwise indicated, each chemical or composition indicated herein shall be interpreted as a commercial grade material which may contain isomers, by-products, derivatives, and other This material. However, the amounts of each chemical component are excluded from any solvents or diluent oils customarily present in commercial grade materials, unless otherwise indicated. It should be understood that the above-described limits, amounts, and ratios can be independently combined. Similarly, the scope and amount of each element of the invention can be used with the scope or amount of any other element.

The term "hydrocarbyl" as used herein is used in the ordinary sense of the term and is intended to include any divalent radical formed by the removal of two hydrogen atoms from a hydrocarbon.

The term "hydrocarbon carbonyl" as used herein is intended to include any hydrocarbon group containing a carbonyl group (>C=O), such as a hydrocarbon group containing a ketone group or a thiol group.

While the invention has been described with respect to the preferred embodiments thereof, it will be understood that Therefore, it is to be understood that the invention disclosed herein is intended to cover such modifications within the scope of the appended claims.

Claims (21)

A polymer comprising a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is represented by formula (1): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond the substituent, and R _{1 is} represented by at least one electron withdrawing group; a is 1 or 2; W is oxygen, sulfur, > NH, or >NG; R ₂ is a C ₁ to C ₂₀ extended hydrocarbon group, or a C ₁ to C ₂₀ extended hydrocarbon carbonyl group, and when R ₂ contains more than 2 carbon atoms, the extended hydrocarbon group or the extended hydrocarbon carbonyl group is linear or branched; R ₃ is H or C _1-50 - a substituted or unsubstituted hydrocarbon group which bonds to a terminal oxygen atom of the polymer chain to form a terminal ether group or a terminal ester group, and may or may not contain a polymerizable group Or a C _1-50 -hydrocarbylcarbonyl group (ie, a hydrocarbyl group containing a carbonyl group) which bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group And the substituent is a halogen group, an ether group, an ester group, or a combination thereof; Pol is a homopolymer chain of ethylene oxide or a copolymer chain of ethylene oxide, wherein the ethylene oxide composition 40% by weight to 99.99% by weight of the copolymer chain, and wherein the polymer chain is selected from the group consisting of poly(ether), and a combination of poly(ether) and poly(ester); u=1 to 3; v=1 to 2; w=1 to 3; v=2 when W=>NG; v=1 when W=oxygen, sulfur or >NG; G is a hydrocarbon group having 1 to 200 carbon atoms; And Q comprises naphthalene, and the Q system is bonded to the quinone imine group in a manner to form a 5 or 6 membered quinone ring. The polymer of claim 1, wherein the polymer chain is (i) a polyethylene oxide homopolymer, or (ii) ethylene oxide and propylene oxide, butylene oxide, epoxy Poly(ether) of a copolymer of a benzene, or a combination thereof. The polymer of claim 2, wherein the poly(ether) comprises: 0 to 70 weight percent propylene oxide, and 30 to 100 weight percent ethylene oxide. The polymer according to any one of claims 1 to 3, which is obtained by the following method: Step (1): (i) amino acid, (ii) amino alcohol, (iii) amine a thiol, or (iv) a diamine, which is fused with an aromatic diacid or anhydride, or another acid to form a derivative, which respectively form an acid functionalized fusion aromatic quinone imine, a hydroxy functionalized fusion aromatic quinone Amine, thiol functionalized fusion aromatic quinone imine, or amine functionalized fusion aromatic quinone imine; step (2): functionalization of the acid to the aromatic quinone imine, the hydroxy group a functionalized fusion of an aromatic quinone imine, a thiol functionalized fusion aromatic quinone imine, or a monomeric functionalized fused aromatic quinone imine in a polymer chain or polymerized to form a monomeric reaction of the polymer chain . The polymer of claim 4, wherein the fused aromatic diacid or anhydride, or other acid forming derivative is based on naphthalene. The polymer of claim 4, wherein the fused aromatic diacid or anhydride, or other acid forming derivative is based on 1,8-naphthoquinone imine, 1,2-naphthylimine, or a combination thereof . The polymer of any one of claims 1 to 3, wherein the Q is based on naphthalic anhydride. The polymer according to any one of claims 1 to 3, wherein the polymer chain is a poly(ether) represented by the formula (2): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond a substituent, and R _{1 is} represented by at least one electron withdrawing group; a is 1 or 2; W is oxygen; R ₂ is a C ₁ to C ₂₀ hydrocarbon group, or a C ₁ to C ₂₀ hydrocarbon carbonyl group, when R ₂ contains more than 2 carbon atoms, the hydrocarbon or carbonyl hydrocarbon group is linear or branched; R ₃ is H or C _1-50 a substituted or unsubstituted hydrocarbon group which bonds to a terminal oxygen atom of the polymer chain to form a terminal ether group or a terminal ester group, and which may or may not contain a polymerizable group, or a C _{1-50 -hydrocarbon} carbonyl group (ie, a hydrocarbon group containing a carbonyl group) which bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group, and the substituent is a halogen group , an ether group, an ester group, or a combination thereof; When it is a homopolymer, R ₄ is H, and In the case of a copolymer, R ₄ is H (amount sufficient to provide 40 to 98.9% by weight of an oxirane group), and a combination of at least one of a methyl group, an ethyl group and a phenyl group; u is 1 to 3; w is 1 to 3; the condition is that when R ₂ is a hydrocarbon group, u is 1 and w is 1; and m is 1 to 110. The polymer according to any one of claims 1 to 3, wherein the polymer chain is a poly(ether) polymer chain represented by the formula (3a): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond the substituent, and R _{1 is} represented by at least one electron withdrawing group; a is 1 or 2; W is oxygen, sulfur, or >NG; R ₂ is a C ₁ to C ₂₀ hydrocarbon group, or a C ₁ to C ₂₀ hydrocarbon carbonyl group; when R ₂ contains more than 2 carbon atoms, the hydrocarbon group or the hydrocarbon carbonyl group is linear or branched; G is contained a hydrocarbon group of 1 to 200 carbon atoms; R ₃ is H or C _1-50 - a substituted or unsubstituted hydrocarbon group which bonds to a terminal oxygen atom of the polymer chain to form a terminal ether group or a terminal ester group, and May or may not contain a polymerizable group, or a C _1-50 -hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group) which bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group. And may or may not contain a polymerizable group, and the substituent is a halogen group, an ether group, an ester group, or a combination thereof; When it is a homopolymer, R ₄ is H, and In the case of a copolymer, R ₄ is H (amount sufficient to provide 40 to 98.9% by weight of an oxirane group), and a combination of at least one of a methyl group, an ethyl group and a phenyl group; u is 1 to 3; w is 1 to 3; and m is 1 to 110. The polymer according to any one of claims 1 to 3, wherein the polymer chain is a poly(ether) polymer chain represented by the formula (3b): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond a substituent, and R _{1 is} represented by at least one electron withdrawing group; a is 1 or 2; W is nitrogen; R ₂ is a C ₁ to C ₂₀ hydrocarbon group, or a C ₁ to C ₂₀ hydrocarbon carbonyl group, when R ₂ contains more than 2 carbon atoms, the hydrocarbon or carbonyl hydrocarbon group is linear or branched; R ₃ is H or C _1-50 a substituted or unsubstituted hydrocarbon carbonyl (ie a hydrocarbon group containing a carbonyl group) which bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group And the substituent is a halo group, an ether group, an ester group, or a combination thereof; When it is a homopolymer, R ₄ is H, and In the case of a copolymer, R ₄ is H (amount sufficient to provide 40 to 98.9% by weight of an oxirane group), and a combination of at least one of a methyl group, an ethyl group and a phenyl group; u is 1 to 3; w is 1 to 3; v is 2; and m is 1 to 110. The polymer according to any one of claims 1 to 3, wherein the polymer chain is a poly(ether)-co-poly(ester) polymer chain represented by the formula (4a): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond the substituent, and R _{1 is} represented by at least one electron withdrawing group; a is 1 or 2; W is oxygen, sulfur, or >NG; R ₂ is a C ₁ to C ₂₀ hydrocarbyl group, or a C ₁ to C ₂₀ hydrocarbon carbonyl group; when R ₂ contains more than 2 carbon atoms, the hydrocarbyl or hydrocarbyl carbonyl group may be linear or branched; G is a hydrocarbon group having 1 to 200 carbon atoms; R ₃ is H or C _1-50 - a substituted or unsubstituted hydrocarbon carbonyl group (i.e., a hydrocarbon group having a carbonyl group) bonded to an oxygen atom of the polymer chain a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group, and the substituent may be a halogen group, an ether group, an ester group, or a combination thereof; When it is a homopolymer, R ₄ is H, and In the case of a copolymer, R ₄ is H (amount sufficient to provide 40 to 98.9% by weight of oxirane groups), and a combination of at least one of methyl, ethyl and phenyl; R ₅ is C _{1- 19} - a hydrocarbon group; u is 1 to 3; w is 1 to 3; q is 1 to 90; and m is 1 to 90, with the condition that m is equal to or greater than q. The polymer according to any one of claims 1 to 3, wherein the polymer chain is a poly(ether)-co-poly(ester) polymer chain represented by the formula (4b): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond a substituent, and R _{1 is} represented by at least one electron withdrawing group; a is 1 or 2; W is nitrogen; R ₂ is C ₁ to C _{20 is a} hydrocarbyl group, or a C ₁ to C _{20 is a} hydrocarbon carbonyl group. When R ₂ contains more than 2 carbon atoms, the hydrocarbyl or hydrocarbyl carbonyl group may be linear or branched; R ₃ is H or C _{1- 50--} substituted by hydrocarbon or unsubstituted carbonyl group of (i.e., containing the hydrocarbon-carbonyl), which is bonded to an oxygen atom of the polymer chain to form a terminal ester group or a urethane terminal group, and may be or may not contain a polymerizable group, and the substituent may be a halogen group, an ether group, an ester group, or a combination thereof; When it is a homopolymer, R ₄ is H, and In the case of a copolymer, R ₄ is H (amount sufficient to provide 40 to 98.9% by weight of oxirane groups), and a combination of at least one of methyl, ethyl and phenyl; R ₅ is C _{1- 19} - a hydrocarbon group; u is 1 to 3; w is 1 to 3; v is 2; q is 1 to 90; and m is 1 to 90, with the condition that m is equal to or greater than q. The polymer of any one of claims 1 to 3, wherein the polymer chain is represented by formula (5): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond the substituent, and R _{1 is} represented by at least one electron withdrawing group; a is 1 or 2; W is oxygen; R ₂ is C ₁ to C ₂₀ extend to a hydrocarbon carbonyl group. When R ₂ contains more than 2 carbon atoms, the hydrocarbon carbonyl group may be linear or branched; and R ₃ is H or C _1-50 - a substituted or unsubstituted hydrocarbon group. Bonding a terminal oxygen atom of the polymer chain to form a terminal ether group or a terminal ester group, and may or may not contain a polymerizable group, or a C _1-50 -hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group), which is bonded The oxygen atom of the polymer chain forms a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group, and the substituent may be a halogen group, an ether group, an ester group, or a combination thereof. ; when When it is a homopolymer, R ₄ is H, and In the case of a copolymer, R ₄ is H (amount sufficient to provide 40 to 98.9% by weight of oxirane groups), and a combination of at least one of methyl, ethyl and phenyl; R ₅ is C _{1- 19} - a hydrocarbon group; u is 1 to 3; w is 1 to 3; q is 1 to 90; and m is 1 to 90, with the condition that m is equal to or greater than q. The polymer according to any one of claims 1 to 3, wherein the electron withdrawing group is -NO ₂ , -SO ₂ NR' ₂ , -C(O)R', -SO ₃ M, -C(O OM, -Cl, or -Br, wherein M is H, a metal cation, -NR' ₄ ⁺ , or a combination thereof, and R' is -H, or a substituted or unsubstituted one having 1 to 20 carbon atoms, respectively An alkyl group, and the substituent may be a hydroxyl group, a halogen group, or a combination thereof. The polymer of any one of claims 1 to 3, wherein the electron withdrawing group is -Cl, -NO ₂ or -SO ₃ M, wherein M is H, a metal cation, -NR' ₄ ⁺ , or In combination, R' is -H, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and the substituent may be a hydroxyl group, a halogen group, or a combination thereof. A composition comprising a particulate solid, an aqueous medium, and a polymer chain having at least one fused aromatic fluorene imine pendant, wherein the polymer is according to any one of claims 1 to 15. Polymer representation. The composition of claim 16 wherein the composition is abrasive, paint or ink. The composition of claim 16 or 17, wherein the particulate solid is a pigment or a filler. The composition of claim 16 or 17, further comprising a binder. The composition of claim 16 or 17, wherein the amount of the polymer is in the range of from 0.1% by weight to 79.6% by weight of the composition. The use of a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer of any one of claims 1 to 15 is as claimed in any one of claims 16 to 20. a dispersant in the composition.