JP2020164639A - Friction and/or wear reducing agent - Google Patents

Abstract

To provide a nano material that has excellent dispersibility in oily solvent, and can contribute to friction and wear reduction.SOLUTION: A friction and/or wear reducing agent contains flaky carbon with a thickness of 1-100 nm, and an organic compound having a hydrophilic group and a hydrophobic group with high carbon affinity, wherein, relative to the flaky carbon 1 pts.mass, the organic compound having the hydrophilic group and the hydrophobic group with high carbon affinity is 0.1-5 pts.mass.SELECTED DRAWING: None

Description

The present invention relates to friction and / or wear reducing agents.

An oil-based solvent such as oil or grease, which requires lubricity, is usually added with a lubricious material such as graphite for the purpose of further reducing friction and wear of the target substance (for example,). See Patent Document 1).

As described above, graphite is known to have lubricity, but due to its large size, even if it is added to an oil-based solvent, it may be trapped by an oil filter and may not work sufficiently. The oil filter is a metal case containing fine-grained filter paper made of special fibers, and is used to remove fine foreign matter.

On the other hand, the graphene sheet is a two-dimensional single-walled sheet in which carbon atoms are arranged in a honeycomb lattice, and is also a constituent unit of graphite, fullerenes, carbon nanotubes, and the like. The flaky carbon in which the graphene sheet is laminated to a thickness of about 100 nm or less (in the present invention, the concept including the graphene sheet) has various unique physical properties, and is therefore used for various materials. It is attracting attention as a new material.

Special Table No. 8-506563

However, if a nanocarbon material is used so as not to be supplemented by the oil filter, the dispersibility in an oil-based solvent is poor, and the nanocarbon materials may aggregate with each other, resulting in insufficient effectiveness.

Therefore, an object of the present invention is to provide a nanomaterial having excellent dispersibility in an oily solvent and capable of contributing to friction and wear reduction.

As a result of diligent research to achieve the above object, the present inventors have determined a predetermined amount of flaky carbon having a thickness of 1 to 100 nm and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon. It has been found that by containing it, a nanomaterial having excellent dispersibility in an oily solvent and capable of contributing to friction and wear reduction can be obtained. The present inventors have further studied based on the findings and have completed the present invention. That is, the present invention includes the following configurations.

Item 1. It contains flaky carbon having a thickness of 1 to 100 nm and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, and has an affinity for the hydrophilic group and carbon with respect to 1 part by mass of the flaky carbon. A friction and / or wear reducing agent containing 0.1 to 5 parts by mass of an organic compound having a highly reactive hydrophobic group.

Item 2. The hydrophilic group is a general formula (1) to (4):

[In the formula, -OH represents an alcoholic hydroxyl group or a phenolic hydroxyl group. R represents a divalent organic group. X ¹ represents a hydrogen atom, alkali metal, NH ₄ or organic ammonium. X ² represents a hydrogen atom, alkali metal, NH ₄ , organic ammonium or alkyl group. The oxygen atom of the general formula (2) is an ether bond. ]
Item 2. The friction and / or wear reducing agent according to Item 1, which is at least one represented by.

Item 3. Item 2. The friction and / or wear reducing agent according to Item 1 or 2, wherein the hydrophilic group is an alcoholic hydroxyl group and / or a polyoxyethylene group.

Item 4. Item 1 to any one of Items 1 to 3, wherein the hydrophobic group is at least one selected from the group consisting of an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, and a polyoxyalkylene group having 3 or more carbon atoms. The friction and / or wear reducing agent described.

Item 5. Item 2. The friction and / or wear reducing agent according to any one of Items 1 to 4, wherein the hydrophobic group is an aryl group having two or more aromatic rings.

Item 6. Item 2. The friction and / or wear reducing agent according to any one of Items 1 to 5, wherein the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon has an HLB value of 1 to 18.

Item 7. The friction and / or wear reducing agent according to any one of Items 1 to 6, further comprising an oil-based additive.

Item 8. Item 2. The friction and / or wear reducing agent according to Item 7, which contains 0.25 to 10 parts by mass of the oil-based additive with respect to 1 part by mass of the flaky carbon.

Item 9. Item 2. The method for producing a friction and / or wear reducing agent according to any one of Items 1 to 8.
(1) The flaky carbon, an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, and a solvent are contained, and the hydrophilic group and carbon are contained with respect to 1 part by mass of the flaky carbon. A production method comprising a step of removing a solvent from a flaky carbon dispersion containing 0.1 to 5 parts by mass of an organic compound having a hydrophobic group having a high affinity.

Item 10. Item 9. The production method according to Item 9, wherein the oil-based additive is contained in the flaky carbon dispersion.

Item 11. Item 9. The production method according to Item 9 or 10, wherein the step of removing the solvent is a step of concentrating the flaky carbon dispersion.

Item 12. Item 8. The production method according to any one of Items 9 to 11, wherein the solvent is water.

Item 13. A friction and / or wear reducing dispersion liquid in which the friction and / or wear reducing agent according to any one of Items 1 to 8 is dispersed in an oily solvent.

According to the present invention, it is possible to obtain a nanomaterial having excellent dispersibility in an oily solvent and capable of contributing to reduction of friction and wear.

When the content of the organic compound having a hydrophobic group having a high affinity with a hydrophilic group and carbon is small (when the surface of the flaky carbon is coated with an organic compound having a hydrophobic group having a high affinity with a hydrophilic group and carbon) The composition of the friction and / or wear reducing agent of the present invention is shown. The present invention of the present invention when the content of an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon is large (when flaky carbon is dispersed in an organic compound having a hydrophobic group having a high affinity with carbon). The composition of the friction and / or wear reducing agent is shown. It is a drawing which shows the outline of the friction wear test (shell walk test) of an Example. It is a drawing which shows the outline of the SRV: vibration friction wear test of an Example.

As used herein, "contains" is a concept that includes any of "comprise," "consist essentially of," and "consist of." Further, in the present specification, when the numerical range is indicated by "A to B", it means A or more and B or less.

Hereinafter, embodiments of the present invention will be described, but various modifications of the embodiments and details are possible without departing from the spirit and scope of the claims.

1. 1. Friction and / or Wear Reducer The friction and / or wear reducer of the present invention contains flaky carbon having a thickness of 1 to 100 nm and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon. , 0.1 to 5 parts by mass of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon is contained with respect to 1 part by mass of the flaky carbon.

(1-1) Flake carbon As the flake carbon, the thinner one is preferable because it is easier to reduce friction and wear and is less likely to be captured by the oil filter. However, considering the dispersibility in the oil solvent, the thickness thereof is 1 to 100 nm. , Preferably 1 to 20 nm. Similarly, the content ratio of flaky carbon having a thickness of 1 to 10 nm is preferably 80% or more, more preferably 90% or more, assuming that the total number of flaky carbons is 100%. That is, although flaky carbon having a large thickness may be contained, the thickness of a large number of flaky carbons is preferably 10 nm or less. The thickness of the flaky carbon is measured by observation with a transmission electron microscope (TEM).

Thinned carbon is preferable because it is easier to reduce friction and wear and is less likely to be captured by the oil filter. However, considering the dispersibility in the oily solvent, 300 layers or less (that is, 1 to 300 layers) of graphene are laminated. Flaky carbon having a layered structure is preferable, and flaky carbon having a layered structure in which 1 to 60 layers of graphene are laminated is more preferable. Similarly, the content ratio of flaky carbon having 1 to 30 layers is preferably 80% or more, more preferably 90% or more, assuming that the total number of flaky carbons is 100%. That is, although flaky carbon having a large thickness may be contained, the thickness of a large number of flaky carbons is preferably 30 layers or less. The lamination of flaky carbon is calculated from the thickness measured by observation with a transmission electron microscope (TEM).

Since flaky carbon usually has a planar shape having many convex and concave angles, it is difficult to unconditionally specify a size other than the thickness. In the present specification, the distance between the most distant convex angles in one flaky carbon is defined as the size of the flaky carbon.

The size of such flaky carbon is preferably 20 nm or more, more preferably 50 nm to 100 μm, and even more preferably 100 nm to 30 μm. By using flaky carbon of such a size, it is easy to reduce friction and wear while being excellent in dispersibility in an oil-based solvent, and it is difficult to be caught by an oil filter. The size of flaky carbon is measured by observing with a microscope (laser microscope, etc.).

In the friction and / or abrasion reducing agent of the present invention, the content of flaky carbon is not particularly limited, but it is easy to reduce friction and abrasion while being superior in dispersibility in an oily solvent, and it is difficult to be captured by an oil filter. Therefore, the total amount of the friction and / or wear reducing agent of the present invention is 100% by mass, preferably 5 to 80% by mass, and more preferably 10 to 70% by mass.

(1-2) Organic compound having a hydrophilic group and a hydrophobic group having a high affinity with carbon In the present invention, the graphene structure is maintained by using an organic compound having a hydrophilic group and a hydrophobic group having a high affinity with carbon. The flaky carbon in the friction and / or wear reducing agent of the present invention can be maintained in a uniformly dispersed state without agglomeration of the flaky carbon. An organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon can also function as a dispersant for uniformly dispersing flaky carbon.

The organic compound having such a hydrophilic group and a hydrophobic group having a high affinity for carbon is not particularly limited, and various organic compounds (particularly water-soluble compounds) that can function as a dispersant for flaky carbon are used. Can be used.

Among them, the hydrophobic group contained in the organic compound having a hydrophilic group and a hydrophobic group having a high affinity with carbon is not particularly limited, but is an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, and a poly having 3 or more carbon atoms. An oxyalkylene group or the like is preferable. An organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon can contain one or more such hydrophobic groups. When a plurality of hydrophobic groups are used, the same hydrophobic group may be used, a plurality of the same hydrophobic group may be used, or a plurality of different hydrophobic groups may be used.

The alkyl group may be a chain alkyl group or a branched chain alkyl group, but a chain alkyl group is preferable from the viewpoint of affinity with carbon. The number of carbon atoms of the alkyl group is preferably 6 or more, more preferably 8 to 28, and even more preferably 10 to 22 from the viewpoint of affinity with carbon. Examples of such an alkyl group include a hexyl group, an octyl group, a decyl group, an undecyl group, a dodecyl group (or lauryl group), a tridecyl group, a tetradecyl group (or myristyl group), a pentadecyl group, a hexadecyl group (or a cetyl group), and the like. Examples thereof include an octadecyl group and an icosyl group.

This alkyl group may or may not have a substituent. Examples of such a substituent include a cycloalkyl group, an aryl group, an aralkyl group and the like. Examples of the cycloalkyl group and the aryl group will be described later.

As the aralkyl group as the substituent of the alkyl group, an aralkyl group having 7 to 14 carbon atoms having an aryl group and an alkyl group having 1 to 6 carbon atoms, which will be described later, is preferable, and specifically, a benzyl group, a phenethyl group and the like are used. preferable.

The substituent is not limited to the above, and may have a group derived from a fluorene structure (fluorenyl group or the like). In particular, when water solubility is important, a phenyl group or the like is preferable as a substituent, and when compatibility with flaky carbon is important, a naphthyl group, a fluorenyl group or the like is preferable as a substituent.

The alkenyl group preferably has 4 or more carbon atoms, more preferably 6 to 100 carbon atoms, and even more preferably 8 to 30 carbon atoms from the viewpoint of affinity with carbon and water solubility. Examples of such an alkenyl group include an oleyl group and a linoleyl group.

This alkenyl group may or may not have a substituent. Examples of such a substituent include an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group and the like. Examples of the aralkyl group include those described above, and examples of the cycloalkyl group and the aryl group include those described below.

As the alkyl group as the substituent of the alkenyl group, an alkyl group having 1 to 6 carbon atoms is preferable, and specifically, a methyl group, an ethyl group, a propyl group, a butyl group, a tert-butyl group and the like are preferable.

The substituent is not limited to the above, and may have a group derived from a fluorene structure (fluorenyl group or the like). In particular, when water solubility is important, a phenyl group or the like is preferable as a substituent, and when compatibility with flaky carbon is important, a naphthyl group, a fluorenyl group or the like is preferable as a substituent.

As the cycloalkyl group, a cycloalkyl group having 5 to 10 carbon atoms (preferably 5 to 8, particularly 5 to 6) is preferable, and specifically, a cyclopentyl group, a cyclohexyl group and the like are preferable.

This cycloalkyl group may or may not have a substituent. Examples of such a substituent include an alkyl group, an aryl group, an aralkyl group and the like.

As the alkyl group as the substituent of the cycloalkyl group, an alkyl group having 1 to 6 carbon atoms is preferable, and specifically, a methyl group, an ethyl group, a propyl group, a butyl group, a tert-butyl group and the like are preferable.

Examples of the aryl group and the aralkyl group as the substituent of the cycloalkyl group include those exemplified above.

The substituent is not limited to the above, and may have a group derived from a fluorene structure (fluorenyl group or the like). In particular, when water solubility is important, a phenyl group or the like is preferable as a substituent, and when compatibility with flaky carbon is important, a naphthyl group, a fluorenyl group or the like is preferable as a substituent.

As the aryl group, an aryl group having 6 to 22 carbon atoms (particularly 6 to 18) is preferable, and any monocyclic aryl group, condensed ring aryl group or polycyclic aryl group can be adopted, for example, a phenyl group, a naphthyl group, etc. Examples thereof include anthrasenyl group, tetrasenyl group, phenanthrenyl group, biphenyl group, terphenyl group, fluorenyl group, acenaphthenyl group, acenaphthylenyl group, pyrenyl group, chrysenyl group, triphenylenyl group and the like. From the viewpoint of affinity with carbon, an aryl group having two or more aromatic rings (condensed aryl group and polycyclic aryl group) is preferable.

This aryl group may or may not have a substituent. Examples of such a substituent include an alkyl group, a cycloalkyl group, an aralkyl group and the like.

As the alkyl group as the substituent of the aryl group, an alkyl group having 1 to 6 carbon atoms is preferable, and specifically, a methyl group, an ethyl group, a propyl group, a butyl group, a tert-butyl group and the like are preferable.

Examples of the cycloalkyl group and the aralkyl group as the substituent of the aryl group include those exemplified above.

The substituent is not limited to the above, and may have a group derived from a fluorene structure (fluorenyl group or the like).

The polyoxyethylene group is usually hydrophilic, but the polyoxyalkylene group having 3 or more carbon atoms, such as a polyoxypropylene group and a polyoxybutylene group, becomes more hydrophobic as the degree of polymerization increases and functions as a hydrophobic group. In particular, a polyoxypropylene group having a degree of polymerization of 4 or more and a polyoxybutylene group having a degree of polymerization of 3 or more are preferable. For example, when polyoxyethylene-polyoxypropylene or polyoxyethylene-polyoxybutylene is used as an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, the polyoxypropylene group and the polyoxybutylene group are also used. Can function as a hydrophobic group.

This polyoxyalkylene group having 3 or more carbon atoms may or may not have a substituent. Examples of such a substituent include an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group and the like.

As the alkyl group as a substituent of the polyoxyalkylene group having 3 or more carbon atoms, an alkyl group having 1 to 6 carbon atoms is preferable, and specifically, a methyl group, an ethyl group, a propyl group, a butyl group and a tert-butyl group. Groups and the like are preferred.

Examples of the cycloalkyl group, the aralkyl group and the aryl group as the substituent of the polyoxyalkylene group having 3 or more carbon atoms include those exemplified above.

The substituent is not limited to the above, and may have a group derived from a fluorene structure (fluorenyl group or the like). In particular, when water solubility is important, a phenyl group or the like is preferable as a substituent, and when compatibility with flaky carbon is important, a naphthyl group, a fluorenyl group or the like is preferable as a substituent.

As such a hydrophobic group, an aryl group and a polyoxyalkylene group having 3 or more carbon atoms are preferable from the viewpoints that they are more excellent in dispersibility in an oily solvent, easily reduce friction and wear, and are less likely to be captured by an oil filter. Aryl groups are more preferred, and aryl groups having two or more aromatic rings (condensed aryl groups and polycyclic aryl groups) are even more preferred. Specifically, a naphthyl group, an anthrasenyl group, a tetrasenyl group, a phenanthrenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, an acenaphthenyl group, an acenaphthylenyl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, and a polyoxypropylene having a degree of polymerization of 4 or more. A group, a polyoxybutylene group having a degree of polymerization of 3 or more, and the like are preferable.

Further, as the hydrophilic group of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, the solubility of the organic compound having a hydrophobic group having a high affinity for the hydrophilic group and carbon in water can be increased. The organic compound having a hydrophobic group having a high affinity with the hydrophilic group and the carbon is water-soluble, the dispersibility of flaky carbon, the dispersibility in an oily solvent, the reduction of friction and wear, and the oil. From the viewpoint of complementability to the filter, general formulas (1) to (4):

[In the formula, -OH represents an alcoholic hydroxyl group or a phenolic hydroxyl group. R represents a divalent organic group. X ¹ represents a hydrogen atom, alkali metal, NH ₄ or organic ammonium. X ² represents a hydrogen atom, alkali metal, NH ₄ , organic ammonium or alkyl group. The oxygen atom of the general formula (2) is an ether bond. ]
The hydrophilic group represented by is preferable. The organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon can contain one or more such hydrophilic groups. When a plurality of hydrophilic groups are used, the same hydrophilic group may be used more than once, a plurality of types of hydrophilic groups represented by the same general formula may be used, or hydrophilicity represented by different general formulas may be used. A plurality of types of groups may be used.

In the general formula (1), -OH may be either an alcoholic hydroxyl group or a phenolic hydroxyl group. However, from the viewpoints of water solubility of organic compounds having hydrophobic groups having high affinity with hydrophilic groups and carbon, dispersibility of flaky carbon, dispersibility in oily solvents, reduction of friction and wear, and compensability to oil filters. , Alcoholic hydroxyl group is preferable. When -OH is a phenolic hydroxyl group, water solubility of an organic compound having a hydrophilic group and a hydrophobic group having a high affinity with carbon, dispersibility of flaky carbon, dispersibility in an oily solvent, reduction of friction and wear, From the viewpoint of complementability to the oil filter, it is preferable to substitute with a hydrophilic group represented by any of the general formulas (2) to (4).

In the general formula (2), the divalent organic group represented by R is not particularly limited, and a divalent hydrocarbon group is preferable. Examples of the divalent hydrocarbon group include an aliphatic hydrocarbon group (alkylene group (or alkylidene group), cycloalkylene group, alkylene (or alkylidene) -cycloalkylene group, bi or tricycloalkylene group, etc.), aromatic hydrocarbon. Examples thereof include a group (arylene group, alkylene (or alkylidene) -arylene group, etc.).

In the general formula (2), as the alkylene group (or alkylidene group) represented by the group R, an alkylene group is preferable, a C _1-8 alkylene group is more preferable, a C _1-4 alkylene group is further preferable, and a C _{2- A 4-} alkylene group is particularly preferable, and a C _2-3 alkylene group is most preferable. Specifically, methylene group, ethylene group, ethylidene group, trimethylene group, propylene group, propyridene group, tetramethylene group, ethylethylene group, butane-2-idene group, 1,2-dimethylethylene group, pentamethylene group, Examples thereof include a pentane-2,3-diyl group.

In the general formula (2), as the cycloalkylene group represented by the group R, a C _5-10 cycloalkylene group is preferable, and a C _5-8 cycloalkylene group is more preferable. Specifically, a cyclopentylene group, a cyclohexylene group, a methylcyclohexanelen group, a cycloheptylene group and the like can be exemplified.

In the general formula (2), as the alkylene (or alkylidene) -cycloalkylene group represented by the group R, an alkylene-cycloalkylene group is preferable, a C _1-6 alkylene-C _5-10 cycloalkylene group is more preferable, and C _{A 1-4} alkylene-C _5-8 cycloalkylene group is more preferred. Specifically, methylene-cyclohexylene group, ethylene-cyclohexylene group, ethylene-methylcyclohexylene group, ethylidene-cyclohexylene group and the like can be exemplified.

In the general formula (2), a norbornane-diyl group or the like can be specifically exemplified as the bi or tricycloalkylene group represented by the group R.

In the general formula (2), the C _6-10 arylene group is preferable as the arylene group represented by the group R. Specifically, a phenylene group, a naphthalene diyl group and the like can be exemplified.

In the general formula (2), as the alkylene (or alkylidene) -arylene group represented by the group R, an alkylene-arylene group is preferable, a C _1-6 alkylene-C _6-20 arylene group is more preferable, and C _1-4. An alkylene-C _6-10 arylene group is more preferable, and a C _1-2 alkylene-phenylene group is particularly preferable. Specifically, a methylene-phenylene group, an ethylene-phenylene group, an ethylene-methylphenylene group, an ethylidene phenylene group and the like can be exemplified.

Of these, a divalent aliphatic hydrocarbon group, particularly an alkylene group (for example, a C _1-4 alkylene group such as a methylene group or an ethylene group) is preferable.

The alkylene (or alkylidene) -cycloalkylene group and the alkylene (alkylidene) -arylene group are -Ra-Rb- (in the formula, Ra is an alkylene bonded to a separate oxygen atom in the general formula (2). A group or an alkylidene group, Rb indicates a cycloalkylene group or an arylene group).

The hydrophilic group represented by the general formula (2) is not particularly limited, and for example, -OC ₂ H ₄ O-, -OC ₃ H ₆ O-, -OCH ₂ O- and the like can be used. .. Those having 1 to 30 of these, more preferably 1 to 10 can also be preferably used, and for example, a polyoxymethylene group, a polyoxyethylene group, a polyoxypropylene group and the like can be used. In particular, when the hydrophilic group represented by the general formula (2) has a structure in which three or more are polymerized, the more carbons in R (for example, three or more carbon atoms), the lower the hydrophilicity and the more hydrophobic, so the degree of polymerization is high. -OC ₂ H ₄ O- and -OCH ₂ O-, which can maintain hydrophilicity even when increased, are preferable.

When having such a hydrophilic group represented by the general formula (2), particularly a polyoxyalkylene group, and further a polyoxyethylene group, dispersibility in an oily solvent, friction and wear reduction, and catchability to an oil filter Especially excellent in.

In the general formula (3), the alkali metal represented by X ¹ is not particularly limited, and examples thereof include sodium, potassium, lithium and the like.

In the general formula (3), quaternary ammonium is preferable as the organic ammonium represented by X ¹ , and tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium and the like can be preferably used.

The hydrophilic group represented by the general formula (3) is not particularly limited, but is, for example, −SO ₃ ⁻ H ⁺ , −SO ₃ ⁻ Na ⁺ , −SO ₃ ⁻ K ⁺ , −SO ₃ ⁻ Li. ⁺ , -SO ₃ ^- NH ₄ ⁺ , -SO ₃ ^- N (CH ₃ ) ₄ ⁺ , -SO ₃ ^- N (C ₂ H ₅ ) ₄ ⁺ , -SO ₃ ^- N (C ₃ H ₇ ) ₄ ⁺ , −SO ₃ ⁻ N (C ₄ H ₉ ) ₄ ^{+ and the} like can be mentioned.

In the general formula (4), examples of the alkali metal and organic ammonium represented by X ² include those exemplified above.

In the general formula (4), the alkyl group represented by X ² may be a chain alkyl group or a branched chain alkyl group, but the water solubility of an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon. A chain alkyl group is preferable from the viewpoints of dispersibility of flaky carbon, dispersibility in an oily solvent, reduction of friction and wear, and catchability for an oil filter. In addition, the number of carbon atoms of the alkyl group is such that the organic compound having a hydrophilic group and a hydrophobic group having a high affinity with carbon is water-soluble, the dispersibility of flaky carbon, the dispersibility in an oil solvent, the reduction of friction and wear, and the oil filter. From the viewpoint of complementability and the like, 1-2 is preferable.

The hydrophilic group represented by the general formula (4) is not particularly limited, but is, for example, -COOH, -COONa, -COOK, -COOLi, -COONH ₄ , -COON (CH ₃ ) ₄ , -COON. (C ₂ H ₅ ) ₄ , -COON (C ₃ H ₇ ) ₄ ⁺ , -COON (C ₄ H ₉ ) ₄ ^{+ and the} like can be mentioned.

Among these hydrophilic groups, the water solubility of organic compounds having a hydrophilic group and a hydrophobic group having a high affinity for carbon, stability regardless of pH, dispersibility of flaky carbon, dispersibility in an oily solvent, friction and abrasion From the viewpoint of reduction, complementability to the oil filter, etc., the hydrophilic group represented by the general formula (1) or (2) is preferable.

However, when the water-soluble compound has a plurality of the same hydrophilic groups represented by the general formula (2), that is, has a polymerized structure, the hydrophilicity of the water-soluble compound increases as the degree of polymerization increases when the number of carbon atoms is 2 or less, but the number of carbon atoms is 3. In the above cases, the hydrophobicity may increase as the degree of polymerization increases.

Further, in the present invention, when a nonionic material (nonionic surfactant or the like) is used as the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, the HLB value thereof is the hydrophilic group and the HLB value. From the viewpoints of water solubility of organic compounds having a hydrophobic group having a high affinity for carbon, dispersibility of flaky carbon, dispersibility in an oily solvent, reduction of friction and wear, and catchability to an oil filter, 1 to 18 are selected. Preferably, 5 to 12 are more preferable. The HLB value is preferably high from the viewpoint of the production efficiency of flaky carbon in water, and the HLB value is preferably low from the viewpoint of dispersion in an oily solvent. When the hydrophobic groups are the same (when the affinity with flaky carbon is about the same), the lower the HLB value is, the more preferable.

The organic compound having a hydrophilic group satisfying the above conditions and a hydrophobic group having a high affinity with carbon is not particularly limited, but an aromatic water-soluble compound may be used, or a non-aromatic water-soluble compound may be used. May be used, but aromatic water-soluble compounds are preferred. Examples of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon include polyoxyethylene lauryl ether, polyoxyethylene decyl ether, polyoxypropylene decyl ether, polyoxyethylene lauryl ether, and polyoxyethylene naphthyl ether. Polyoxypropylene lauryl ether, polyoxypropylene naphthyl ether, polyoxyethylene myristyl ether, polyoxypropylene myristyl ether, polyoxyethylene cetyl ether, polyoxypropylene cetyl ether, polyoxyethylene octylphenyl ether, polyoxypropylene octylphenyl ether, Polyoxyethylene undecylphenyl ether, polyoxypropylene undecylphenyl ether, polyoxyethylene tridecylphenyl ether, polyoxypropylene tridecylphenyl ether, polyoxyethylene pentadecylphenyl ether, polyoxypropylene pentadecylphenyl ether, polyoxy Ethylene polyoxypropylene glycol, polyoxypropylene polyglyceryl ether, sodium colate, potassium colate, sodium dodecylsulfonate, potassium dodecylsulfonate, sodium dilauroyl glutamate lysine, potassium dilauroyl glutamate lysine, decaglycerin laurate ester, n- Examples include decyl alcohol.

Examples of the organic compound having such a hydrophilic group and a hydrophobic group having a high affinity for carbon include Emargen 103, Emargen 104P, Emargen 105, Emargen 106, Emargen 108, Emargen 109P, Emargen 120, Emargen 123P, and Emargen 130K. Emargen 147, Emargen 150, Emargen 210P, Emargen 220 (above, polyoxyethylene alkyl ethers manufactured by Kao Co., Ltd.), Triton X-100, Triton X-114, Triton X-305, Triton X-405 (above, Dow) Polyoxyethylene octylphenyl ethers manufactured by Chemical Co., Ltd.), Neugen EN, Neugen EN-10 (above, polyoxyethylene naphthyl ether manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) and the like can be used.

The content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity with carbon in the friction and / or wear reducing agent of the present invention is not particularly limited, but is the dispersibility of flaky carbon and the dispersibility in an oily solvent. From the viewpoint of friction and wear reduction, complementability to the oil filter, etc., the total amount of the friction and / or wear reducing agent of the present invention is preferably 10 to 85% by mass, more preferably 15 to 50% by mass. preferable. Further, the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon in the friction and / or wear reducing agent of the present invention is 0.1 to 5 mass by mass with respect to 1 part by mass of flaky carbon. Parts, preferably 0.25 to 1 parts by mass. If the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon is less than 0.1 parts by mass, agglomerates of flaky carbon will settle and cannot be dispersed in an oily solvent. On the other hand, if the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon exceeds 5 parts by mass, the handleability is poor. When the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon is small, the friction and / or wear reducing agent of the present invention has an affinity for the hydrophilic group and carbon on the surface of the flaky carbon. It has a structure in which an organic compound having a highly hydrophobic group is coated (Fig. 1). On the other hand, when the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity with carbon is large, the friction and / or wear reducing agent of the present invention is an organic compound having a hydrophobic group having a high affinity with carbon. It has a structure in which flaky carbon is dispersed (Fig. 2). In either case, an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon is interposed around the flaky carbon to suppress the aggregation of the flaky carbon, and the dispersibility of the flaky carbon and the oily solvent. It is possible to obtain a material having excellent dispersibility, reduction of friction and wear, and catchability to an oil filter.

(1-3) Oil-based additive The friction and / or wear reducing agent of the present invention may contain an oil component (oil-based additive) as an additive. Thereby, the friction and / or abrasion reducing agent of the present invention can be further made into a material having excellent dispersibility in an oily solvent and further excellent friction and abrasion reducing performance.

The oil-based additive is not particularly limited, and known or commercially available products can be used. Specifically, poly-α-olefin synthetic oil, ester synthetic oil, partially synthetic oil, and mineral oil. , Vegetable oil and the like. These oil-based additives can be used alone or in combination of two or more.

The content of the oil-based additive in the friction and / or wear reducing agent of the present invention is not particularly limited, but the dispersibility of flaky carbon, the dispersibility in the oily solvent, the friction and wear reduction, and the catchability for the oil filter. From the above viewpoints, the total amount of the friction and / or wear reducing agent of the present invention is 100% by mass, preferably 10 to 90% by mass, and more preferably 15 to 85% by mass. Further, the content of the oil-based additive in the friction and / or wear reducing agent of the present invention is not particularly limited, but the dispersibility of flaky carbon, the dispersibility in an oil-based solvent, the friction and wear reduction, and the coating on the oil filter. From the viewpoint of complementarity and the like, 0.2 to 10 parts by mass is preferable, and 0.4 to 8 parts by mass is more preferable with respect to 1 part by mass of flaky carbon.

(1-4) Other components In the friction and / or wear reducing agent of the present invention, other components are included in addition to flaky carbon and organic compounds having a hydrophilic group and a hydrophobic group having a high affinity for carbon. May be good. Examples of such other components include carbon fibers (particularly carbon nanofibers having a fiber diameter of 500 nm or less), activated carbon, carbon black (acetylene black, oil furnace black, etc .; particularly high conductivity and large specific surface area). Black), glassy carbon, carbon microcoil, fullerene, biomass-based carbon materials (bagas, sorghum, wood chips, shavings, bamboo, bark, rice straw, paddy husks, coffee husks, tea husks, tea husks, rice bran, pulp waste, etc. Raw materials; carbon fibers manufactured from lignin, etc.), cellulose nanofibers, boron nitride, molybdenum compounds (molybdenum disulfide, organic molybdenum, etc.), tungsten disulfide, fluororesins (polytetrafluoroethylene (PTFE), tetrafluoro) Ethylene / perfluoroalkyl vinyl ether copolymer (PFA), etc.), melamine cyanurate, phthalocyanine, lead oxide, calcium fluoride, layered minerals (mica, talc, etc.), etc. are used as long as the effects of the present invention are not impaired. You can also do it.

However, from the viewpoints of dispersibility of flaky carbon, dispersibility in an oily solvent, reduction of friction and wear, and ability to be captured by an oil filter, the content of other components is preferably small, and the friction and friction of the present invention and / Or the total amount of the wear reducing agent is 100% by mass, preferably 0.01 to 10% by mass, and more preferably 0.02 to 5% by mass.

The shape of the friction and / or wear reducing agent of the present invention is not particularly limited, and examples thereof include a coating film, a sheet, and a lump.

As described above, such a friction and / or abrasion reducing agent of the present invention is a material having excellent dispersibility in an oily solvent, friction and abrasion reduction, etc., and is difficult to be captured by an oil filter because it is a nanomaterial. ..

Such friction and / or wear reducing agents of the present invention include vehicle lubricants, marine lubricants, industrial lubricants, solid lubricants, greases, work oils, and lubricant sprays that also serve as rust and corrosion inhibitors. Thermoplastic resin additives (various injection molded products, extrusion molded products, sheet molded products, blow molded products, compression molded products), rubber additives (tires, shoe soles, athletic supplies, floor tiles, belts, hoses, impact resistant containers) , Anti-vibration rubber, rolls, wire coatings, paints, sealants, packings, gaskets, window and door frames, weather strips, antistatic sheets, diaphragms, coking materials, handrails, thermoplastic elastomer additives), etc. be able to.

2. Method for Producing Friction and / or Wear Reducer The friction and / or wear reducer of the present invention is, for example,
(1) The flaky carbon, an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, and a solvent are contained, and the hydrophilic group and carbon are contained with respect to 1 part by mass of the flaky carbon. It can be produced by a step of removing a solvent from a flaky carbon dispersion containing 0.1 to 5 parts by mass of an organic compound having a hydrophobic group having a high affinity.

(2-1) Flaky carbon dispersion In the flaky carbon dispersion, the above description can be adopted for the flaky carbon and the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon. Further, the flaky carbon dispersion may contain the above-mentioned oil-based additive and other components, if necessary.

This flaky carbon dispersion may be formed as a dispersion liquid or as a coating film on a substrate. At this time, as the solvent used for producing the flaky carbon dispersion (flaky carbon dispersion liquid or flaky carbon coating film), the dispersibility of flaky carbon, the obtained friction and / or wear reducing agent It is preferable to use water as the main solvent from the viewpoints of reducing friction and wear, and being able to catch up with the oil filter.

The content of water in the solvent used is not particularly limited, but is a solvent from the viewpoints of dispersibility of flaky carbon, friction and / or wear reduction of the obtained friction and / or wear reducing agent, and catchability to the oil filter. With the total amount of 100% by mass, 70% by mass or more (70 to 100% by mass) is preferable, and 75 to 100% by mass is more preferable.

In the present invention, only water may be used as the solvent, and an organic solvent may not necessarily be used, but an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon can be added to water. In order to further improve the solubility, alcohols such as methanol, ethanol, 2-propanol and tert-butyl alcohol; glycols such as ethylene glycol; glycerin; and organic solvents such as 2-methoxyethanol may be used.

The content of the organic solvent in the solvent used is the solubility of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity with carbon, the friction and / or friction and wear reduction of the obtained friction and / or wear reducing agent, and the supplement to the oil filter. From the viewpoint of properties and the like, the total amount of the solvent is 100% by mass, and it is preferably 30% by mass or less (0 to 30% by mass), more preferably 5 to 25% by mass.

In the above-mentioned flaky carbon dispersion, the content of flaky carbon is not particularly limited, but from the viewpoint of easy composition of the friction and / or wear reducing agent of the present invention, the total amount of flaky carbon dispersion is set to 100% by mass. , 20% by mass or less, more preferably 0.0001 to 15% by mass, still more preferably 0.001 to 10% by mass. Similarly, the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon is not particularly limited, but from the viewpoint of facilitating the composition of the friction and / or wear reducing agent of the present invention, flaky carbon. Assuming that the total amount of the dispersion is 100% by mass, 0.00001 to 99.9% by mass is preferable, 0.0001 to 50% by mass is more preferable, and 0.001 to 30% by mass is further preferable. Similarly, the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon in the flaky carbon dispersion is flaky from the viewpoint that the composition of the friction and / or wear reducing agent of the present invention can be easily obtained. 0.1 to 5 parts by mass is preferable, and 0.25 to 1 part by mass is more preferable with respect to 1 part by mass of carbon. Similarly, when an oil-based additive is used, the content of the oil-based additive is not particularly limited, but from the viewpoint of facilitating the composition of the friction and / or wear reducing agent of the present invention, the flaky carbon dispersion With the total amount as 100% by mass, 0.00001 to 50% by mass is preferable, 0.0001 to 30% by mass is more preferable, and 0.001 to 20% by mass is further preferable. Similarly, when an oil-based additive is used, the content of the oil-based additive in the flaky carbon dispersion is 1 mass of flaky carbon from the viewpoint that the composition of the friction and / or wear reducing agent of the present invention can be easily obtained. 0.2 to 10 parts by mass is preferable, and 0.4 to 8 parts by mass is more preferable with respect to the part. Further, the content of the solvent is not particularly limited, but from the viewpoint of facilitating the composition of the friction and / or wear reducing agent of the present invention, the total amount of the flaky carbon dispersion is 100% by mass, and 40 to 99.9998% by mass. Is preferable, 63 to 99.998% by mass is more preferable, and 85 to 99.98% by mass is further preferable.

(2-2) Method for producing flaky carbon dispersion In the present invention, the method for producing the flaky carbon dispersion is not particularly limited, and has high affinity for flaky carbon, hydrophilic groups and carbon with respect to the solvent. An organic compound having a hydrophobic group can also be added. Specifically, flaky carbon can be added to a dispersion of an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, or a dispersion of flaky carbon having an affinity for a hydrophilic group and carbon. It is also possible to add an organic compound having a high hydrophobic group. Further, flaky carbon and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon can be simultaneously added to the solvent.

However, the dispersibility of flaky carbon is further improved to make it difficult to aggregate, and the resulting friction and / or wear reducing agent of the present invention has dispersibility in an oil solvent, friction and wear reduction, complementability to an oil filter, etc. From the viewpoint of, a carbonaceous material having a layered structure and an organic having a hydrophilic group and a hydrophobic group having a high affinity for carbon between the rotating rotating disk and the disk installed substantially parallel to the rotating disk. A composition containing the compound is placed, and shearing is applied to the carbonaceous material in the composition while adjusting the shortest distance between the rotating disk and the disk to be 200 μm or less, and then, if necessary. It is preferable to add an oil-based additive accordingly (grinding method).

Further, the flaky carbon dispersion is subjected to a pressure treatment of 30 MPa or more on a composition containing a carbonaceous material having a layered structure and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon. After that, it can also be preferably produced by adding an oil-based additive if necessary (high-pressure dispersion method).

The high-pressure dispersion method is preferable from the viewpoints of flaky carbon, the resulting dispersibility as a friction and / or wear reducing agent of the present invention, and the ability to be captured by an oil filter, and the friction and / or friction of the wear reducing agent. From the viewpoint of reducing wear and the like, the grinding method is preferable.

Conventionally, when flaky carbon is produced by a wet method, an aqueous dispersion containing an oxide of flaky carbon and an aqueous solvent has been subjected to a reduction treatment, but it is difficult to maintain the graphene structure by this method. At the same time, it was difficult to obtain a flaky carbon aqueous dispersion because the obtained flaky carbon aggregated violently. There was also a problem from the viewpoint of safety. On the other hand, in the present invention, by using an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, the flaky carbon maintaining the graphene structure is uniformly dispersed without agglomeration (flaky carbon). The flaky carbon can be obtained from the dispersion), the obtained flaky carbon is not easily destroyed, the flaky carbon can be obtained in a short time, and the lumps that have failed to be peeled off are hard to remain. At this time, the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon can also function as a dispersant for uniformly dispersing flaky carbon.

Further, according to the shearing method, the direction in which the force is applied is parallel to the plane direction of the carbonaceous material having a layered structure, and the processing is performed in a narrow space. In comparison, there is less breakage, peeling efficiency is good, processing can be performed in a short time (small number of passes), and thick lumps that have failed to peel are less likely to remain.

Carbonaceous material having a layered structure The carbonaceous material having a layered structure is not particularly limited, and examples thereof include natural graphite, artificial graphite, expanded graphite, earthy graphite, and graphite oxide. As the graphite oxide, for example, graphite oxidized by one or more kinds of oxidizing agents such as sulfuric acid, nitric acid, potassium permanganate, and hydrogen peroxide can be used. For example, when graphite oxide is obtained by the Hammers method, the graphite is immersed in concentrated sulfuric acid, potassium permanganate is added to oxidize the graphite, and then the reaction product is quenched with dilute sulfuric acid and / or hydrogen peroxide. After that, by washing with distilled water or the like, oxygen atoms are bonded to carbon atoms, and oxygen atoms are introduced between the layers to obtain graphite oxide.

Among them, in the case of obtaining highly pure flaky carbon containing no heteroatoms such as oxygen, it is preferable to use graphite as a raw material, and natural graphite and expanded graphite are more preferable. When expanded graphite is used, it is preferable to use expanded graphite with less oxidation of the graphene structure. When expanded graphite is used, it may be used after being heat-treated at about 300 to 1000 ° C. for about 10 seconds to 5 hours. This makes it possible to obtain expanded graphite that has been appropriately expanded.

Further, when importance is attached to ease of production, graphite oxide may be used. By using graphite oxide, solvent molecules are easily inserted between the layers, it is easy to exfoliate only in the layer direction, and the thinning efficiency and dispersibility are improved, so that the treatment time can be shortened. is there. However, when graphite oxide is used, a reduction treatment is required later, and from the viewpoint of maintaining the graphene structure, conductivity and strength, other materials (natural graphite, artificial graphite, expanded graphite, earthy graphite) Is preferable.

On the other hand, it is also possible to use earth-like graphite in order to further improve the dispersibility. However, from the viewpoint of crystallinity, purity and structure maintenance, other materials (natural graphite, artificial graphite, expanded graphite, graphite oxide) are preferable.

Further, when the crystallinity, strength, structure maintenance and the like of the obtained flaky carbon are emphasized, artificial graphite can also be used.

In the present invention, the content of the carbonaceous material having a layered structure in the composition containing the carbonic material having a layered structure and the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon is not particularly limited. The total amount of the composition used for producing the flaky carbon dispersion is 100% by mass, preferably 20% by mass or less, more preferably 0.0001 to 15% by mass, further preferably 0.001 to 10% by mass. preferable. As for the content of the carbonaceous material having a layered structure, the thinner the material, the more likely it is that flaking (delamination) occurs, so that flaky carbon can be obtained more efficiently, and the number of treatments tends to be reduced. There is a tendency that it is easy to perform shearing treatment while maintaining the viscosity appropriately. On the other hand, the higher the content of the carbonaceous material having a layered structure, the more excellent the productivity. Therefore, from the viewpoint of balancing the efficiency of flaking, viscosity, productivity, etc., it is preferable to appropriately set the content of the carbonaceous material having a layered structure. When a carbonaceous material dispersion is used, it is preferable that the content of the carbonaceous material having a layered structure in the flaky carbon dispersion is within the above range.

Organic compound having a hydrophobic group having a high affinity with a hydrophilic group and carbon As the organic compound having a hydrophobic group having a high affinity with a hydrophilic group and carbon, the above-mentioned ones can be adopted.

In the present invention, the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon in the composition used for producing the flaky carbon dispersion is not particularly limited, but the flaky carbon dispersion is not particularly limited. The total amount of the composition used for producing the above is 100% by mass, preferably 0.00001 to 99.9% by mass, more preferably 0.0001 to 50% by mass, still more preferably 0.001 to 30% by mass. .. On the other hand, in the present invention, the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon in the composition used for producing the flaky carbon dispersion is a carbonaceous material 1 having a layered structure. 0.1 to 5 parts by mass is preferable, and 0.25 to 1 part by mass is more preferable with respect to parts by mass. The content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon is such that the thinner the content of the carbonaceous material having a relatively layered structure, the larger the content of the friction and / or wear reducing agent. It is easy to reduce friction and wear, and it is easy to process at low cost. On the other hand, the higher the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, the more likely it is that flaking (delamination) occurs, so flaky carbon tends to be obtained more efficiently. As the viscosity increases, the flaking efficiency may decrease. Therefore, from the viewpoint of the balance between the dispersibility of the flaky carbon, the dispersibility of the obtained friction and / or wear reducing agent in the oil solvent, the friction and wear reduction, and the catchability of the oil filter, the hydrophilic groups and carbon are used. It is preferable to appropriately set the content of the organic compound having a hydrophobic group having a high affinity. When a carbonaceous material dispersion is used in this production method, the content of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon in the carbonaceous material dispersion is within the above range. Is preferable.

Solvent In the above-mentioned method for producing a flaky carbon dispersion, as described above, a composition containing a carbonaceous material having a layered structure and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon is used. , It is preferable to perform a specific treatment, but the sharding efficiency of the carbonaceous material having a layered structure, the dispersibility of the obtained friction and / or wear reducing agent in the oily solvent, the friction and wear reduction, and the supplement to the oil filter. From the viewpoint of properties and the like, it is preferable to perform a specific treatment on a carbonaceous material dispersion containing a carbonaceous material having a layered structure and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon. ..

The carbonaceous material dispersion may be formed as a dispersion liquid or as a coating film on a substrate.

At this time, the above-mentioned solvent can be adopted as the solvent used for producing the carbonaceous material dispersion (carbonaceous material dispersion liquid or carbonaceous material coating film).

In the present invention, when a specific treatment is carried out using a carbonaceous material dispersion using a solvent, the total amount of the solvent in the carbonaceous material dispersion is not particularly limited, but the carbonic material having a layered structure is fragmented. From the viewpoint of efficiency, solubility of an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, etc., the total amount of the carbonaceous material dispersion is 100% by mass, preferably 40 to 99.9998% by mass, and 63 to 99%. .998% by mass is more preferable, and 85 to 99.98% by mass is further preferable.

In the present invention, when a specific treatment is carried out using a carbonaceous material dispersion using a solvent, the carbonaceous material dispersion has a layered structure on an organic compound dispersion having a hydrophilic group and a hydrophobic group having a high affinity for carbon. A carbonaceous material having a layered structure may be charged, or an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon may be charged into the carbonaceous material dispersion having a layered structure. Further, a carbonaceous material having a layered structure and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon may be simultaneously added to the solvent.

Other Ingredients In the present invention, the composition containing a carbonaceous material having a layered structure and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon (for example, a carbonaceous material dispersion) may be used. Ingredients may be included. Thereby, these other components can be contained in the finally obtained friction and / or wear reducing agent of the present invention. As such other components, those described above can be adopted and may be used as long as the effects of the present invention are not impaired. However, from the viewpoints of the dispersibility of flaky carbon, the dispersibility of the obtained friction and / or wear reducing agent of the present invention in an oily solvent, the reduction of friction and wear, and the catchability of the oil filter, other components may be used. The content is preferably small, and the total amount of the carbonaceous material dispersion is 100% by mass, preferably 0.00001 to 5% by mass, and more preferably 0.0001 to 2% by mass.

Shearing (grinding method)
In the present invention, when the grinding method is adopted, as described above, a carbonaceous material having a layered structure, a hydrophilic group and carbon are provided between the rotating rotating disk and the disk installed substantially parallel to the rotating disk. A composition containing an organic compound having a hydrophobic group having a high affinity with the above is installed, and the carbonaceous material in the composition is adjusted so that the shortest distance between the rotating disk and the disk is 200 μm or less. On the other hand, it is preferable to perform a process of applying shear. When a carbonaceous material dispersion is used, the carbonaceous material dispersion is installed between the rotating rotating disk and the disk installed substantially parallel to the rotating disk, and the rotating disk and the above-mentioned rotating disk are installed. It is preferable to perform a treatment of applying shear to the carbonaceous material in the carbonaceous material dispersion while adjusting the shortest distance from the board to 200 μm or less.

The graphene structure may not be maintained depending on the conditions because the carbonaceous material having a layered structure is atomized by the shearing treatment, but the carbonaceous material having a layered structure is efficiently sliced. It is possible to reduce the processing time. The rotating disk and the disk when performing such a shearing process are installed substantially in parallel, but they do not have to be strictly parallel. Specifically, the angle formed by the axis perpendicular to the rotating disk and the axis perpendicular to the disk is preferably 10 ° or less, and more preferably 5 ° or less. It is most preferable that the axis perpendicular to the rotating disk and the axis perpendicular to the disk are strictly parallel. The shortest distance between the two surfaces when performing such a shearing treatment is not particularly limited as long as the carbonaceous material having a layered structure can be sufficiently thinned, but is preferably 200 μm or less. ~ 50 μm is more preferable, and 2 to 30 μm is even more preferable. Although the rotating disk and the disk are installed substantially in parallel, the distance between the rotating disk and the disk may differ depending on the location. In this case, the shortest distance between the rotary disc and the disc means the distance of the shortest portion of the distance between the rotary disc and the disc. Further, it is not always necessary to leave the rotary disk and the disk apart in advance, a material to be processed may be sandwiched between the rotary disk and the disk, and the rotary disk and the disk may be brought into contact with each other. By sandwiching the carbonaceous material having a layered structure, the space between the rotating disk and the disk may be widened. Such a shearing process may be performed by using a stone mill, a vibrating mixer, a spin coater, a grinder, or the like, as long as there is a mechanism for rotating a disk-shaped object.

The sizes of the rotating disk and the disk that can be used at this time are not particularly limited, and are preferably 5 to 500 mm, more preferably 10 to 200 mm. The number of rotations of the turntable during the shearing treatment is not particularly limited, and is preferably in the range where the carbonaceous material having a layered structure can be sufficiently thinned, for example, 1000 to 10000 ppm. , 2000-5000 ppm is more preferable.

By performing such a shearing treatment, the plate and the carbonic material having a layered structure, and the carbonic material having a layered structure and the carbonic material having a layered structure are brought into contact with each other to form a layered material with respect to the carbonic material having a layered structure. Shear can be applied in the direction parallel to the graphene layer of the carbonaceous material having a structure.

By reducing the shortest distance between the rotating disk and the rotating disk in the shearing process and increasing the rotational speed of the rotating disk, the conditions can be strengthened, and a thin piece of carbonaceous material having a layered structure can be obtained. The conversion can be performed more efficiently, and the processing time can be further reduced. This shearing operation can be performed once or more, preferably three or more times.

The temperature at which the shearing treatment is performed is not particularly limited, and may be a temperature at which the carbonaceous material having a layered structure can be sufficiently thinned, and is 0 ° C. or higher, further 0 to 100 ° C., particularly 20 to 95 ° C. obtain. The temperature at which the shearing treatment is performed is preferably a condition in which the solubility of the organic compound having a hydrophilic group and a hydrophobic group having a high affinity with carbon is high, and when the higher the temperature, the higher the solubility, the higher the temperature is, and the cloud point is formed. When a water-soluble compound is used, it is preferable to keep the temperature below the cloud point.

Before performing the above shearing treatment, a stirrer, an ultrasonic disperser, or the like is used in order to bring the carbonaceous material having a layered structure into good contact with the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon. The organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon may be blended on the surface of the carbonaceous material having a layered structure by stirring in advance before preparing the composition.

In the present invention, when graphite oxide is used as the carbonaceous material having a layered structure, it exists as an oxide of flaky carbon in the dispersion subjected to the shearing treatment. Therefore, when graphite oxide is used as the carbonaceous material having a layered structure, it is preferable to perform a reduction treatment as a post-treatment. As the reduction treatment, various methods such as chemical reduction and electrochemical reduction can be adopted, but chemical reduction is preferable. Of these, chemical reduction with a reducing agent such as hydrazine or sodium borohydride is preferable. The amount of the reducing agent is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, and even more preferably 0.5 to 3 parts by mass with respect to 1 part by mass of the oxide of flaky carbon. Further, if heating is performed at the time of reduction, the reduction becomes easier. The heating temperature is preferably 40 to 200 ° C, more preferably 50 to 150 ° C, and even more preferably 60 to 120 ° C. The reduction time is preferably 10 minutes to 64 hours, more preferably 30 minutes to 48 hours, still more preferably 1 to 24 hours. However, it is preferable that the graphene structure is not excessively destroyed.

According to the above-mentioned production method, the flaky carbon can be obtained as the above-mentioned flaky carbon dispersion. Since this production method contains an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, even in a flaky carbon dispersion, the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon can be contained. include. Since this organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon can be adsorbed on the surface of flaky carbon and isolated and dispersed the flaky carbon in a solvent at a high concentration, the flaky carbon is dispersed. It also functions as a dispersant in the body. Further, as the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, a commercially available product can be used, which is superior to the conventional product in terms of both cost and dispersibility. Furthermore, the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon exhibits sufficient dispersibility in an oily solvent, friction and wear reduction performance, etc. by remaining on the surface of flaky carbon, and is an oil. It can be less likely to be captured by the filter.

Further, in the conventional method of performing the oxidation treatment and the reduction treatment, the plastic substrate is hydrolyzed during the reduction treatment, and the flaky carbon aggregates when the reduction treatment is performed, so that it cannot exist as a dispersion. Therefore, it was impossible to form a flaky carbon dispersion on a plastic substrate, but in the present invention, a specific organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon is contained. By performing the treatment, it is also possible to form a flaky carbon dispersion on the substrate without the plastic substrate such as polyethylene terephthalate (PET) being hydrolyzed.

When the friction and / or wear reducing agent of the present invention contains an oil-based additive, it is preferable to mix it with the oil-based additive so as to have the above-mentioned composition after the above-mentioned shearing treatment.

Pressurization treatment (high pressure dispersion method)
In the present invention, when the high-pressure dispersion method is adopted, as described above, 30 MPa is applied to a composition containing a carbonaceous material having a layered structure and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon. It is preferable to perform the above pressurization treatment.

The graphene structure may not be maintained depending on the conditions because the carbonaceous material having a layered structure is atomized by the pressure treatment, but the carbonaceous material having a layered structure can be efficiently sliced. This can be done and the processing time can be reduced. The pressure level at the time of performing such a pressure treatment is not particularly limited as long as it can sufficiently thin the carbonaceous material having a layered structure, but is preferably 30 MPa or more, preferably 50 to 400 MPa. Is more preferable, and 100 to 300 MPa is further preferable. Such pressurization treatment can be performed using a high-pressure disperser, a supercritical water preparation device, or the like. The high-pressure disperser can disperse by applying mechanical pressure, and in the supercritical water preparation device, the pressure of the system can be increased by heating water.

By such pressurization, for example,
(I) Colliding two or more of the carbonaceous material dispersions with each other.
(Ii) Collision of the carbonaceous material dispersion with a metal or ceramic material (material having high hardness such as silicon carbide or alumina).
(Iii) The carbonaceous material dispersion can be passed through a space having a cross-sectional area of 1 cm ² or less.

According to the above (i) and (ii), the pressurizing condition can be strengthened, the carbonaceous material having a layered structure can be sliced more efficiently, and the processing time can be further reduced. be able to. Further, according to the above (iii), it is possible to more appropriately thin the carbonaceous material having a layered structure while maintaining the graphene structure more appropriately. This pressurizing operation can be performed once or more, preferably 10 times or more.

The pressurizing temperature is not particularly limited and may be a temperature at which the carbonaceous material having a layered structure can be sufficiently thinned. In the cases of (i) and (ii) above, 0 to 100 ° C., particularly 20 It can be ~ 95 ° C. Further, in the case of (iii) above, 0 to 100 ° C. is preferable when mechanically applying pressure, 373 to 700 ° C. is preferable when pressure is generated by the supercritical state of water, and 380 to 450 ° C. is more preferable. preferable.

When the pressure treatment is performed, it is preferable to perform an ultrasonic dispersion treatment as a preliminary treatment (pretreatment) to atomize the carbonaceous material having a layered structure. This can have an effect of preventing clogging and the like.

The output when the ultrasonic dispersion treatment is applied is not particularly limited, but it is stronger than the usual ultrasonic dispersion treatment (about 40 to 50 W) from the viewpoint of thinning the carbonaceous material having a layered structure. Is preferable. Specifically, the output of the ultrasonic dispersion treatment is preferably 100 W or more, more preferably 300 to 20000 W, and even more preferably 400 to 18000 W.

The ultrasonic dispersion temperature is not particularly limited, and may be a temperature at which the carbonaceous material having a layered structure can be sufficiently thinned, and may be 0 to 80 ° C., particularly 10 to 70 ° C. The ultrasonic dispersion time is not particularly limited, and may be a time during which the carbonaceous material having a layered structure can be sufficiently thinned, and may be 1 to 600 minutes, particularly 3 to 120 minutes.

Further, as the pretreatment or the posttreatment of these treatments, a dispersion treatment by another dispersion device such as ordinary mechanical stirring, a dispersion treatment by an emulsifying device, and a dispersion treatment by a bead mill may be used in combination.

In the present invention, when graphite oxide is used as the carbonaceous material having a layered structure, it exists as an oxide of flaky carbon in the dispersion subjected to the pressure treatment. Therefore, when graphite oxide is used as the carbonaceous material having a layered structure, it is preferable to perform a reduction treatment as a post-treatment. As the reduction treatment, various methods such as chemical reduction and electrochemical reduction can be adopted, but chemical reduction is preferable. Of these, chemical reduction with a reducing agent such as hydrazine or sodium borohydride is preferable. The amount of the reducing agent is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, and even more preferably 0.5 to 3 parts by mass with respect to 1 part by mass of the oxide of flaky carbon. Further, if heating is performed at the time of reduction, the reduction becomes easier. The heating temperature is preferably 40 to 200 ° C, more preferably 50 to 150 ° C, and even more preferably 60 to 120 ° C. The reduction time is preferably 10 minutes to 64 hours, more preferably 30 minutes to 48 hours, still more preferably 1 to 24 hours. However, it is preferable that the graphene structure is not excessively destroyed.

When the friction and / or wear reducing agent of the present invention contains an oil-based additive, it is preferable to mix it with the oil-based additive so as to have the above-mentioned composition after the above-mentioned shearing treatment.

(2-3) Method for producing friction and / or wear reducing agent of the present invention The friction and / or wear reducing agent of the present invention can be obtained by removing a solvent from the above-mentioned flaky carbon dispersion.

In order to remove the solvent, a method of concentrating the flaky carbon dispersion can be mentioned. In addition to drying the flaky carbon dispersion, a method of spin-coating the flaky carbon dispersion on a substrate or drying after coating, usually It can be carried out by the method of recovering the friction and / or wear reducing agent of the present invention by solid-liquid separation of. As a method for performing solid-liquid separation, for example, a method used for ordinary solid-liquid separation, for example, a method of filtering using a filter paper, a glass filter, or the like; a method of filtering after centrifugation; a vacuum filter is used. The method can be exemplified. Next, the drying method is not particularly limited, and for example, a method of drying at about 50 to 200 ° C. for about 1 to 24 hours using a warm air dryer or the like can be exemplified.

3. 3. Friction and / or wear reduction dispersion liquid In the friction and / or wear reduction dispersion liquid of the present invention, the above-mentioned friction and / or wear reduction agent of the present invention is dispersed in an oil solvent.

The oily solvent is not particularly limited, and known or commercially available products can be used. Specifically, poly-α-olefin synthetic oil, ester synthetic oil, partially synthetic oil, mineral oil, etc. Examples include vegetable oil. These oil-based solvents can be used alone or in combination of two or more.

The amount of the oily solvent used can be the amount of the solvent, and can be an excess amount with respect to the friction and / or wear reducing agent of the present invention. Specifically, the friction and / or wear reducing of the present invention can be used. The concentration of the agent can be adjusted to 0.001 to 5% by mass, particularly 0.01 to 3% by mass.

The friction and / or wear reducing agent of the present invention is an oil-based nanomaterial that suppresses the aggregation of flaky carbon, has excellent dispersibility in an oil-based solvent, and can contribute to friction and wear reduction. It can be easily dispersed in a solvent. By immersing the material to be treated in the friction and / or wear reduction dispersion of the present invention thus obtained, it is possible to reduce the friction and / or wear of the material to be treated.

Specific examples of such a material to be processed include bearings, mechanical operating parts such as engines, and mechanical members such as bolts, nuts, chains, gears, and spindles that are exposed to friction and vibration. In addition, thermoplastic resins (polyethylene resin, polypropylene resin, polystyrene resin, polyvinyl chloride resin, polyvinylidene chloride resin, vinyl acetate resin, thermoplastic polyurethane resin, polyvinylidene fluoride resin, acrylonitrile-butadiene-styrene copolymer (ABS). ) Resin, acrylonitrile-styrene copolymer (AS) resin, polymethylmethacrylate resin, polyamide resin, polyacetal resin, polycarbonate resin, polyarylate resin, polyphenylene ether resin, polyethylene terephthalate resin, polybutylene terephthalate resin, cyclic polyolefin resin, polyphenylene. Sulfide resin, polyether ether ketone resin, thermoplastic polyimide resin, polyamideimide resin, etc.), rubber (diene rubber (styrene / butadiene rubber, isoprene rubber, butadiene rubber, chloroprene rubber, etc.), olefin rubber (ethylene / propylene rubber, etc.) , Ethylene / propylene / diene rubber, etc.), acrylic rubber, butyl rubber, epichlorohydrin rubber, silicone rubber (silicone rubber, etc.), thermoplastic rubber, fluororubber, etc.) to reduce friction and wear. be able to. Molding materials that can be used are tires, soles, athletic supplies, floor tiles, belts, hoses, impact-resistant containers, anti-vibration rubber, rolls, wire coatings, paints, sealants, packings, gaskets, window and door frames. , Weather strips, antistatic sheets, diaphragms, caulking materials, handrails and the like.

Hereinafter, the present invention will be specifically described with reference to Examples. However, the present invention is not limited to the examples.

Example 1: An ultrasonic disperser of 600 W by mixing 500 g of flaky carbon + polyoxyethylene naphthyl ether (manufactured by Showa Denko KK), 250 g of polyoxyethylene naphthyl ether (HLB value 18) and 10000 g of water. The dispersion treatment was carried out for 5 minutes using the above, and the dispersion treatment (colliding two or more carbonaceous material dispersions with each other) was performed 100 times at 245 MPa using a high-pressure disperser.

The obtained dispersion was spray-dried at 220 ° C. to obtain a powder having a diameter of about 50 μm (polyoxyethylene naphthyl ether / flaky carbon ratio of 0.5 by mass ratio) as a friction and / or wear reducing agent.

The obtained friction and / or wear reducing agent was added to the oil (synthetic oil for gasoline / diesel engine vehicles; Mobil 10W-20 manufactured by Mobile) so that the carbon component was 0.1% by mass, and 600 W. The ultrasonic dispersion was carried out for 10 minutes to obtain a dispersion liquid as a friction and / or wear reduction dispersion liquid.

The obtained friction and / or wear-reducing dispersion was subjected to a friction and wear test (shell walk test: ASTM D4172) as shown in FIG. 3 using a shell walk tester. Specifically, a container in which three stainless steel balls (1/2 inch in diameter) are fixed in a sample container is submerged in the obtained friction and / or wear reduction dispersion, and then one rotation is performed in the center of the fixed balls. A stainless steel ball (1/2 inch in diameter) is pressed with a load of 40 kgf and brought into contact at three points, the temperature of the friction and / or wear reduction dispersion is set to 75 ° C., and the speed is 1200 rpm for 1 hour. It was rotated. After the test, the diameter of the wear mark generated at the contact point was measured and found to be 0.33 mm.

In addition, since the supernatant was generated in the oil one month after the test, it can be seen that the friction and / or wear reducing agent was dispersed in the oil for one month.

Example 2: Friction and / or wear reducing agent obtained in Example 1 in flaky carbon + polyoxyethylene naphthyl ether oil (synthetic oil for gasoline / diesel engine vehicle; Mobil 10W-20 manufactured by Mobile). , The carbon component was added so as to be 0.05% by mass, and ultrasonic dispersion of 600 W was carried out for 10 minutes to obtain a dispersion liquid as a friction and / or wear reduction dispersion liquid.

The friction coefficient of the obtained friction and / or wear-reducing dispersion was measured by SRV: vibration friction and wear test (ASTM D6425) as shown in FIG. Specifically, a flat plate sample (disk) fixed on a test table is submerged in the obtained friction and / or wear reduction dispersion, and then a load of 400 kgf is applied to the cylinder on the flat plate sample (disk). The cylinder was reciprocated (vibrated) horizontally for 1 hour at an amplitude of 1.5 mm, a frequency of 50 Hz, and a temperature of 100 ° C. while pressing. After the test, the sliding friction coefficient μ was measured and found to be 0.14.

In addition, since the supernatant was generated in the oil one month after the test, it can be seen that the friction and / or wear reducing agent was dispersed in the oil for one month.

Example 3: Flake carbon + polyoxyethylene naphthyl ether 500 g of natural graphite (manufactured by Ito Graphite Industry Co., Ltd.), polyoxyethylene naphthyl ether (HLB value 10) 250 g and water 10000 g are mixed and stirred, and a mixed solution is obtained. Got

This mixed solution was subjected to one shearing treatment at 1500 rpm for 30 minutes using a ceramic grinder having a radius of 300 mm. The shortest distance of the ceramic grinder was about 10 μm.

The obtained dispersion was dried under reduced pressure at 90 ° C. to obtain a black flake-like solid (polyoxyethylene naphthyl ether / flaky carbon ratio 0.5 by mass ratio) as a friction and / or wear reducing agent.

The obtained friction and / or wear reducing agent was added to the oil (synthetic oil for gasoline / diesel engine vehicles; Mobil 10W-20 manufactured by Mobile) so that the carbon component was 0.1% by mass, and 600 W. The ultrasonic dispersion was carried out for 10 minutes to obtain a dispersion liquid as a friction and / or wear reduction dispersion liquid.

For the obtained friction and / or wear reduction dispersion, the static friction coefficient and the dynamic friction coefficient with respect to the stainless steel plate were measured. Specifically, a friction test was conducted in which a stainless steel plate (SUS304 plate) was submerged in the obtained friction and / or wear reduction dispersion, and a metal ball (diameter 10 mm) was reciprocated on the surface thereof. For the measurement, Tribogear TYPE14FW manufactured by Shinto Kagaku Co., Ltd. was used. As a result, the coefficient of static friction was 0.153 μs and the coefficient of dynamic friction was 0.127 μK.

Example 4: Flake carbon + polyoxyethylene naphthyl ether + 500 g of synthetic oil natural graphite (manufactured by Ito Graphite Industry Co., Ltd.), 250 g of polyoxyethylene naphthyl ether (HLB value 10) and 10000 g of water are mixed and stirred. , A mixed solution was obtained.

This mixed solution was subjected to one shearing treatment at 1500 rpm for 30 minutes using a ceramic grinder having a radius of 300 mm. The shortest distance of the ceramic grinder was about 10 μm.

To the obtained dispersion, 0.5 times the mass ratio of oil with respect to the carbon component (synthetic oil for gasoline / diesel engine vehicles; Mobil 10W-20 manufactured by Mobile) was added, and ultrasonic dispersion of 600 W was performed by 10. After a minute, the oil was dispersed in water and a black dispersion was obtained.

The obtained dispersion was dried under reduced pressure at 90 ° C. and was a flake-like solid (polyoxyethylene naphthyl ether / flaky carbon ratio 0.5 by mass ratio, oil / flaky carbon ratio 0.5 by mass ratio). Was obtained as a friction and / or wear reducing agent.

The obtained friction and / or wear reducing agent was added to the oil (synthetic oil for gasoline / diesel engine vehicles; Mobil 10W-20 manufactured by Mobile) so that the carbon component was 0.1% by mass, and 600 W. The ultrasonic dispersion was carried out for 10 minutes to obtain a dispersion liquid as a friction and / or wear reduction dispersion liquid.

Since the obtained friction and / or wear reducing dispersion did not produce a supernatant even after 1 month and remained black, the friction and / or wear reducing agent was dispersed in the oil even after 1 month. You can see that there is.

Further, with respect to the obtained friction and / or wear reduction dispersion, the static friction coefficient and the dynamic friction coefficient with respect to the stainless steel plate were measured in the same manner as in Example 3. As a result, the coefficient of static friction was 0.132 μs and the coefficient of dynamic friction was 0.121 μK.

Example 5: Flake carbon + polyoxyethylene naphthyl ether + 500 g of synthetic oil natural graphite (manufactured by Ito Graphite Industry Co., Ltd.), 250 g of polyoxyethylene naphthyl ether (HLB value 10) and 10000 g of water are mixed and 600 W. Dispersion treatment was carried out for 10 minutes using an ultrasonic disperser to obtain a mixed solution.

This mixed solution was subjected to one shearing treatment at 1500 rpm for 30 minutes using a ceramic grinder having a radius of 300 mm. The shortest distance of the ceramic grinder was about 10 μm.

To the obtained dispersion, 1.5 times the mass ratio of oil (synthetic oil for gasoline / diesel engine vehicles; Mobil 10W-20 manufactured by Mobile) was added to the carbon component, and the ultrasonic dispersion of 600 W was 10 After a minute, the oil was dispersed in water and a black dispersion was obtained.

The obtained dispersion was dried under reduced pressure at 90 ° C. and was a flake-like solid (polyoxyethylene naphthyl ether / flaky carbon ratio 0.5 by mass ratio, oil / flaky carbon ratio 1.5 by mass ratio). Was obtained as a friction and / or wear reducing agent.

The obtained friction and / or wear reducing agent was added to the oil (synthetic oil for gasoline / diesel engine vehicles; Mobil 10W-20 manufactured by Mobile) so that the carbon component was 0.1% by mass, and 600 W. The ultrasonic dispersion was carried out for 10 minutes to obtain a dispersion liquid as a friction and / or wear reduction dispersion liquid.

Since the obtained friction and / or wear reducing dispersion did not produce a supernatant even after 1 month and remained black, the friction and / or wear reducing agent was dispersed in the oil even after 1 month. You can see that there is.

Comparative Example 1: Oil only Oil (synthetic oil for gasoline / diesel engine vehicles; Mobile 10W-20 manufactured by Mobile) was not added with anything, and a friction wear test (shell four-ball test: ASTM D4172) was performed in the same manner as in Example 1. The wear mark diameter was 0.48 mm, and the amount of wear was larger than that of Example 1.

Further, when nothing was added to the oil (synthetic oil for gasoline / diesel engine vehicles; Mobil 10W-20 manufactured by Mobile), SRV: vibration friction and wear test (ASTM D6425) was performed in the same manner as in Example 2. The sliding friction coefficient μ was 0.17, and the friction coefficient was larger than that of Example 2.

Further, when nothing was added to the oil (synthetic oil for gasoline / diesel engine vehicles; Mobil 10W-20 manufactured by Mobile) and the static friction coefficient and the dynamic friction coefficient with respect to the stainless steel plate were measured in the same manner as in Example 3, the static friction coefficient was measured. Was 0.165 μs and the coefficient of dynamic friction was 0.140 μK, and the coefficient of friction was larger than that of Examples 3 and 4.

Comparative Example 2: Only 500 g of flaky carbon (manufactured by Showa Denko KK), 250 g of polyoxyethylene naphthyl ether (HLB value 18) and 10000 g of water were mixed and used for 5 minutes using a 600 W ultrasonic disperser. The dispersion treatment was added, and the dispersion treatment (colliding two or more carbonaceous material dispersions with each other) was performed 100 times at 245 MPa using a high-pressure disperser.

To the obtained dispersion, 4 times the mass ratio of ethanol was added, and the mixture was filtered. Further, 4 times the mass ratio of acetone was added, filtered, and dried under reduced pressure at 90 ° C. to obtain a flaky solid as a friction and / or wear reducing agent.

Most of the polyoxyethylene naphthyl ether was washed away by ethanol and acetone, and when analyzed by TG-DTA, the polyoxyethylene naphthyl ether / flaky carbon ratio was 0.025 by mass ratio.

The obtained friction and / or wear reducing agent is added to the oil (synthetic oil for gasoline / diesel engine vehicles; Mobil 10W-20 manufactured by Mobile) so that the carbon component is 0.1% by mass, and the mixture is stirred. However, the friction and / or wear reducing agent was not dispersed in the oil at all. Further, ultrasonic dispersion of 600 W was performed for 10 minutes, and the agglomerates settled. As a result of allowing to stand for 24 hours, the carbon component was completely precipitated.

Comparative Example 3: 500 g of flaky carbon only , natural graphite (manufactured by Ito Graphite Industry Co., Ltd.), 250 g of polyoxyethylene naphthyl ether (HLB value 10) and 10000 g of water were mixed and stirred to obtain a mixed solution.

This mixed solution was subjected to one shearing treatment at 1500 rpm for 30 minutes using a ceramic grinder having a radius of 300 mm. The shortest distance of the ceramic grinder was about 10 μm.

To the obtained dispersion, 4 times the mass ratio of ethanol was added, and the mixture was filtered. Further, 4 times the mass ratio of acetone was added, filtered, and dried under reduced pressure at 90 ° C. to obtain a flaky solid as a friction and / or wear reducing agent.

Most of the polyoxyethylene naphthyl ether was washed away by ethanol and acetone, and when analyzed by TG-DTA, the polyoxyethylene naphthyl ether / flaky carbon ratio was 0.03 by mass ratio.

The obtained friction and / or wear reducing agent is added to the oil (synthetic oil for gasoline / diesel engine vehicles; Mobil 10W-20 manufactured by Mobile) so that the carbon component is 0.1% by mass, and the mixture is stirred. However, the friction and / or wear reducing agent was not dispersed in the oil at all. Further, ultrasonic dispersion of 600 W was performed for 10 minutes, and the agglomerates settled. As a result of allowing to stand for 24 hours, the carbon component was completely precipitated.

As described above, in the present invention, friction and abrasion can be reduced by coexisting a predetermined amount of an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon with flaky carbon and dispersing the organic compound in oil. did it. Further, when an oil-based additive was added, it was possible to prepare a powder that was more easily dispersed in the oil and could maintain the dispersed state.

Claims (13)

It contains flaky carbon having a thickness of 1 to 100 nm and an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, and has an affinity for the hydrophilic group and carbon with respect to 1 part by mass of the flaky carbon. A friction and / or wear reducing agent containing 0.1 to 5 parts by mass of an organic compound having a highly reactive hydrophobic group. The hydrophilic group is a general formula (1) to (4):
[In the formula, -OH represents an alcoholic hydroxyl group or a phenolic hydroxyl group. R represents a divalent organic group. X ¹ represents a hydrogen atom, alkali metal, NH ₄ or organic ammonium. X ² represents a hydrogen atom, alkali metal, NH ₄ , organic ammonium or alkyl group. The oxygen atom of the general formula (2) is an ether bond. ]
The friction and / or wear reducing agent according to claim 1, which is at least one type represented by. The friction and / or wear reducing agent according to claim 1 or 2, wherein the hydrophilic group is an alcoholic hydroxyl group and / or a polyoxyethylene group. Any one of claims 1 to 3, wherein the hydrophobic group is at least one selected from the group consisting of an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, and a polyoxyalkylene group having 3 or more carbon atoms. Friction and / or wear reducing agent according to. The friction and / or wear reducing agent according to any one of claims 1 to 4, wherein the hydrophobic group is an aryl group having two or more aromatic rings. The friction and / or wear reducing agent according to any one of claims 1 to 5, wherein the organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon has an HLB value of 1 to 18. The friction and / or wear reducing agent according to any one of claims 1 to 6, further comprising an oil-based additive. The friction and / or wear reducing agent according to claim 7, wherein the oil-based additive is contained in an amount of 0.25 to 10 parts by mass with respect to 1 part by mass of the flaky carbon. The method for producing a friction and / or wear reducing agent according to any one of claims 1 to 8.
(1) The flaky carbon, an organic compound having a hydrophilic group and a hydrophobic group having a high affinity for carbon, and a solvent are contained, and the hydrophilic group and carbon are contained with respect to 1 part by mass of the flaky carbon. A production method comprising a step of removing a solvent from a flaky carbon dispersion containing 0.1 to 5 parts by mass of an organic compound having a hydrophobic group having a high affinity. The production method according to claim 9, wherein an oil-based additive is contained in the flaky carbon dispersion. The production method according to claim 9 or 10, wherein the step of removing the solvent is a step of concentrating the flaky carbon dispersion. The production method according to any one of claims 9 to 11, wherein the solvent is water. A friction and / or wear reducing dispersion liquid in which the friction and / or wear reducing agent according to any one of claims 1 to 8 is dispersed in an oily solvent.