KR102515280B1 - Polyphenylene sulfide composite material and manufacturing method thereof - Google Patents

Abstract

The present invention relates to a polyphenylene sulfide composite material and a manufacturing method thereof, and more particularly, the composite material includes polyphenylene sulfide and a carbon material, wherein the carbon material is reduced from graphene oxide through elemental sulfur, in It is characterized by improved thermal stability, thermal conductivity, electrical conductivity and flame retardancy through in situ polymerization.

Description

Polyphenylene sulfide composite and manufacturing method thereof

The present invention relates to a polyphenylene sulfide composite material and a manufacturing method thereof, and more particularly, the composite material includes polyphenylene sulfide and a carbon material, wherein the carbon material is reduced from graphene oxide through elemental sulfur, in It is characterized by improved thermal stability, thermal conductivity, electrical conductivity and flame retardancy through in situ polymerization.

Polyphenylene sulfide (PPS) is an engineering plastic having a structure in which aromatic rings and sulfur atoms alternate in a main chain. Polyphenylene sulfide is used in the automotive field and electric and electronic fields due to its excellent properties of high heat resistance, chemical resistance and flame retardancy. However, despite these advantages, polyphenylene sulfide is brittle due to its high crystallinity, making it difficult to use it alone.

In order to overcome this, research on combining polyphenylene sulfide and fillers is being conducted. However, materials used as fillers, for example, general carbon materials such as carbon nanotubes and graphene, have low dispersibility in a polyphenylene sulfide matrix, making it difficult to improve physical properties. Therefore, it is required to manufacture a composite material through a filler having high dispersibility in a polyphenylene sulfide matrix.

Korean Patent Publication No. 10-2020-0112748

The present invention provides a polyphenylene sulfide composite material using a sulfur-doped carbon material as a filler and a manufacturing method thereof.

The object of the present invention is not limited to the object mentioned above. The objects of the present invention will become more apparent from the following description, and will be realized by means and combinations thereof set forth in the claims.

A composite material according to an embodiment of the present invention includes a matrix including polyphenylene sulfide; and a filler dispersed in the matrix, wherein the filler includes a sulfur-doped carbon material.

The carbon material may include at least one selected from the group consisting of graphene oxide, reduced graphene oxide, carbon nanotubes, carbon fibers, and combinations thereof.

The filler may include 0.5% to 5% by weight of sulfur.

The composite material may include the filler in an amount of 0.1% to 50% by weight.

A method for manufacturing a composite material according to an embodiment of the present invention includes preparing a filler including a carbon material doped with sulfur; and preparing a matrix including polyphenylene sulfide and a filler dispersed therein by in-situ synthesis by adding sodium sulfide, dichlorobenzene, and the filler to a solvent.

Preparing the filler may include preparing a mixture containing carbon material and sulfur; heat-treating the mixture to convert sulfur into molten sulfur and reacting the mixture; and removing sulfur from the reaction product.

The molar ratio of the sodium sulfide to dichlorobenzene may be 0.95 to 1:1.02.

The manufacturing method may be to adjust the molar ratio of the sodium sulfide and dichlorobenzene according to the amount of sulfur included in the filler and the content of the filler included in the composite material.

The manufacturing method may be to lower the molar ratio of sodium sulfide when the content of the filler included in the composite material is 10% by weight or more and the content of sulfur included in the filler is 2% by weight or more.

When the content of the filler included in the composite material is 10% to 50% by weight, the yield of the polyphenylene sulfide may be 55% or more.

Thermal conductivity of the composite material may be 0.3 W/mK or more.

Electrical conductivity of the composite material may be 1 X 10 ^-8 S/cm or more.

Heat release capacity per unit mass of the composite material may be 180 W/g or less.

According to the present invention, a composite material with improved thermal stability, thermal conductivity, electrical conductivity, and flame retardancy can be obtained.

According to the present invention, a composite material in which a filler is uniformly dispersed in a matrix containing polyphenylene sulfide can be obtained.

According to the present invention, it is possible to obtain a composite material in which the filler content is high and the filler is evenly dispersed in the matrix.

The effects of the present invention are not limited to the effects mentioned above. It should be understood that the effects of the present invention include all effects that can be inferred from the following description.

1 is a thermogravimetric analysis (TGA) graph of composite materials according to Comparative Example 1 and Examples 1 to 4.
2 is a thermogravimetric analysis (TGA) graph of composites according to Examples 5 to 8;
3 is a temperature-heat release rate graph of composite materials according to Comparative Example 1 and Examples 1 to 5.

The above objects, other objects, features and advantages of the present invention will be easily understood through the following preferred embodiments in conjunction with the accompanying drawings. However, the present invention is not limited to the embodiments described herein and may be embodied in other forms. Rather, the embodiments introduced herein are provided so that the disclosed content will be thorough and complete and the spirit of the present invention will be sufficiently conveyed to those skilled in the art.

Like reference numbers have been used for like elements throughout the description of each figure. In the accompanying drawings, the dimensions of the structures are shown enlarged than actual for clarity of the present invention. Terms such as first and second may be used to describe various components, but the components should not be limited by the terms. These terms are only used for the purpose of distinguishing one component from another. For example, a first element may be termed a second element, and similarly, a second element may be termed a first element, without departing from the scope of the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise.

In this specification, terms such as "include" or "have" are intended to designate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, but one or more other features It should be understood that it does not preclude the possibility of the presence or addition of numbers, steps, operations, components, parts, or combinations thereof. In addition, when a part such as a layer, film, region, plate, etc. is said to be "on" another part, this includes not only the case where it is "directly on" the other part, but also the case where there is another part in the middle. Conversely, when a part such as a layer, film, region, plate, etc. is said to be "under" another part, this includes not only the case where it is "directly under" the other part, but also the case where there is another part in between.

Unless otherwise specified, all numbers, values and/or expressions expressing quantities of components, reaction conditions, polymer compositions and formulations used herein refer to the number of factors that such numbers arise, among other things, to obtain such values. Since these are approximations that reflect the various uncertainties of the measurement, they should be understood to be qualified by the term "about" in all cases. Also, when numerical ranges are disclosed herein, such ranges are contiguous and include all values from the minimum value of such range to the maximum value inclusive, unless otherwise indicated. Furthermore, where such ranges refer to integers, all integers from the minimum value to the maximum value inclusive are included unless otherwise indicated.

A composite material according to the present invention includes a matrix including polyphenylene sulfide; and a filler dispersed in the matrix. The present invention relates to a composite material having improved physical properties such as thermal stability, thermal conductivity, electrical conductivity, and flame retardancy by adding a filler to a matrix containing polyphenylene sulfide.

The matrix is a kind of substrate forming the shape of the composite material. In order to add a filler to the matrix, if the matrix and the filler are simply mixed by a method such as melt compounding, a composite material containing a high content of the filler cannot be obtained. This is because the dispersibility of the filler in the matrix is poor. The present invention proposes a method capable of adding a high content of a filler to a matrix comprising polyphenylene sulfide.

First, the filler may include a carbon material doped with sulfur.

The carbon material may include at least one selected from the group consisting of graphene oxide, reduced graphene oxide, carbon nanotubes, carbon fibers, and combinations thereof, and may include graphene oxide or reduced graphene oxide in terms of thermal conductivity and electrical conductivity. Graphene oxide may be preferred. Therefore, the filler may preferably include sulfur-doped reduced graphene oxide.

However, since graphene is easily self-aggregated due to van der Waals force between each layer, it is difficult to disperse in the matrix. Accordingly, the present invention seeks to solve this problem in various ways, one of which is to dope the carbon material with sulfur. Here, 'doping' means that the sulfur is physically and/or chemically bonded to the carbon element of the carbon material. The sulfur-doped carbon material has an affinity for the sulfur atom of polyphenylene sulfide, so that it can be more evenly dispersed in the matrix.

On the other hand, the manufacturing method of the composite material according to the present invention comprises the steps of preparing a filler containing a sulfur-doped carbon material; and adding sodium sulfide, dichlorobenzene, and the filler to a solvent and performing in-situ synthesis to prepare a matrix including polyphenylene sulfide and a filler dispersed therein. The present invention is characterized by in-situ synthesis of the polyphenylene sulfide precursor and the filler in order to uniformly disperse the filler in a matrix containing polyphenylene sulfide.

Preparing the filler may include preparing a mixture including the carbon material and sulfur; heat-treating the mixture to convert sulfur into molten sulfur and reacting the mixture; and removing sulfur from the reaction product.

The mixture including the carbon material and sulfur may be heat treated at 100 °C to 300 °C, or 120 °C to 250 °C, or 150 °C to 180 °C, or 180 °C. The heat treatment time varies depending on the temperature, but may be, for example, 30 minutes to 6 hours or 3 hours to 4 hours.

When the mixture is heat-treated from 150° C. to 180° C., for example, up to 170° C., a viscous molten phase is formed. The molten phase contains molten sulfur. A sulfur-doped carbon material may be obtained through a reaction between molten sulfur and a carbon material. The sulfur may be introduced into a specific functional group such as a ketone group, an epoxy group, a phenol group, etc. present on the carbon material. In this case, when the carbon material is graphene oxide, since the sulfur may serve as a reducing agent, reduced graphene oxide doped with sulfur may be obtained.

Obtaining a sulfur solution by adding a sulfur soluble solvent to the sulfur remaining after the reaction is completed; and removing sulfur from the sulfur solution.

The sulfur-soluble solvent refers to a solvent having solubility characteristics for sulfur, and non-limiting examples include tetrahydrofuran, methylene chloride, dimethyldisulfide, sulfolane, chloroform, toluene, xylene, acetonitrile, dichloromethane, N-methyl Pyrrolidone, ethyl acetate, dimethyl ether, trichlorethylene, polyethylene glycol, isopropyl ketone, acetonitrile, dichloroethane, dimethylacetamide, dimethylformamide, cumene, benzene, p-chlorotoluene, 1,3 -mesitylene, styrene, chlorobenzene, alphamethylstyrene, ethylbenzene, diethanolamine, ethylamine, diethylamine, methylamine, ethylenediamine, diethylenetriamine, propylamine, ethanolamine, isopropylamine, triethylene tetraamine, chloroaniline, triethylamine, triethanolamine, dimethoxyethane, dimethoxymethane, dioxane and the like.

Ultrasonic treatment is performed on the sulfur solution, and the resulting product is filtered and/or washed to remove unreacted sulfur or sulfur physically attached to the carbon material.

A composite material may be prepared by injecting the filler obtained as above into a solvent together with a precursor of polyphenylene sulfide including sodium sulfide and dichlorobenzene and synthesizing it in-situ. Unlike the present invention, when a filler is added to synthesized polyphenylene sulfide and melt compounded, it is difficult to increase the physical properties of the composite material to a desired level due to the low dispersibility of the filler.

Meanwhile, even when the filler and the precursor are synthesized in situ, the yield of polyphenylene sulfide varies greatly depending on the amount of sulfur contained in the filler and the content of the filler. The inventors of the present invention have found that the yield of polyphenylene sulfide can be increased by adjusting the molar ratio of sodium sulfide and dichlorobenzene when the content of sulfur and filler is increased. It will be described in detail below.

The filler may include 0.5% to 5% by weight of sulfur. If the sulfur content is less than 0.5% by weight, it is difficult to react by stirring the sulfur and the carbon material, and the effect of improving physical properties such as flame retardancy according to the addition of the filler may be insignificant. On the other hand, if the sulfur content exceeds 5% by weight, it may be difficult to remove sulfur remaining after preparing the filler.

The composite material may include the filler in an amount of 0.1% to 50% by weight. If the content of the filler is less than 0.1% by weight, the degree of improvement in thermal stability, thermal conductivity, electrical conductivity, and flame retardancy of the composite material may be insignificant. On the other hand, if the content of the filler exceeds 50% by weight, dispersibility of the filler in the matrix may be too low.

A molar ratio of sodium sulfide, which is a precursor of polyphenylene sulfide, to dichlorobenzene within a range of the amount of sulfur included in the filler and the content of the filler included in the composite material may be 0.95 to 1:1.02. Here, the present invention is to adjust the molar ratio of sodium sulfide in the direction of lowering within the above numerical range when the content of the filler contained in the composite is 10% by weight or more and the content of sulfur contained in the filler is 2% by weight or more characterized by

As a result, according to the present invention, the content of the filler included in the composite material is 10% to 50% by weight, or 20% to 50% by weight, or 30% to 50% by weight, or 40% to 50% by weight. Even when the yield is high, the yield of polyphenylene sulfide may be 55% or more, or 70% or more.

Hereinafter, the present invention will be described in more detail through examples. These examples are only for illustrating the present invention, and it will be apparent to those skilled in the art that the scope of the present invention is not to be construed as being limited by these examples.

manufacturing example - Hwangi doped reduced of graphene oxide manufacturing

1 g of graphene oxide and 3 g of sulfur powder were mixed well using a mortar and put into a 500 ml round bottom flask.

Thereafter, the temperature of the oil bath is set to 180° C. and magnetic stirring is performed. It was confirmed that stirring began as sulfur began to melt at around 120 ° C. The temperature of the reaction mixture was heated to 170° C. to obtain molten sulfur, and the reaction mixture containing the same was stirred for 4 hours, and then the reaction was terminated.

After cooling the reaction product to room temperature, ultrasonication was performed using toluene to remove remaining sulfur. It was then filtered to obtain a toluene solution in which solid and sulfur were dissolved. The solid was washed with acetone and then dried in a vacuum oven at 180° C. for 24 hours to prepare sulfur-doped reduced graphene oxide (hereinafter referred to as S-rGO).

Example 1

Prior to polymerization, water contained in sodium sulfide pentahydrate (Na ₂ S·5H ₂ O) was removed through dehydration. N-methylpyrrolidone solvent and sodium sulfide pentahydrate (Na ₂ S·5H ₂ O) were added to the reactor, stirred under a nitrogen stream, and reacted at a temperature of 120° C. until a theoretical amount of water was extracted.

Sodium sulfide (Na ₂ S) obtained through the dehydration reaction was stirred for 4 hours under a pressure of 40 bar and a temperature of 260 ° C. in an N-methylpyrrolidone solvent together with dichlorobenzene and S-rGO of the above preparation, and at the same time ( in-situ) reacted. At this time, the molar ratio of sodium sulfide and dichlorobenzene was 1:1.02. The S-rGO content was added to be 0.1% by weight based on the theoretical yield of the final polyphenylene sulfide.

The prepared composite was purified through hot distilled water and methanol. Finally, in order to remove internal moisture, the composite was prepared in a powder form by sufficiently drying the mixture in a vacuum oven at 100° C. for 12 hours or more.

Example 2 to 8

A composite material was prepared in the same manner as in Example 1, except that the content of S-rGO was adjusted as shown in Table 1.

Example 9

A composite material was prepared in the same manner as in Example 1, except that the content of S-rGO having a sulfur content of 5.5% by weight was adjusted to be 1% by weight and added.

Example 10

The content of S-rGO having a sulfur content of 2.2% by weight was adjusted to be 10% by weight, and the molar ratio of sodium sulfide and dichlorobenzene was adjusted to 0.99: 1.02. Other than that, a composite material was prepared in the same manner as in Example 1.

Example 11

The content of S-rGO having a sulfur content of 2.2% by weight was adjusted to be 50% by weight, and the molar ratio of sodium sulfide and dichlorobenzene was adjusted to 0.95: 1.02. Other than that, a composite material was prepared in the same manner as in Example 1.

comparative example One

A polyphenylene sulfide composite was prepared in the same manner as in Example 1, except that S-rGO was not added.

Comparative Example 2 to 5

A composite material was prepared in the same manner as in Example 1, except that the content of S-rGO having a sulfur content of 5.5% by weight was adjusted as shown in Table 1.

Comparative Example 6

A composite material was prepared in the same manner as in Example 1, except that the content of S-rGO having a sulfur content of 2.2% by weight was adjusted to 10% by weight and added.

Comparative Example 7

The content of S-rGO having a sulfur content of 2.2% by weight was adjusted to 50% by weight, and the molar ratio of sodium sulfide and dichlorobenzene was adjusted to 0.97: 1.02. Other than that, a composite material was prepared in the same manner as in Example 1.

division Filler Dosage
(weight%) Sulfur content of filler
(weight%) [Na ₂ S] : [DCB]
(mol) transference number (%) Example 1 0.1 1.2 1:1.02 74.6 Example 2 0.5 1.2 1:1.02 71.9 Example 3 One 1.2 1:1.02 77.9 Example 4 5 1.2 1:1.02 67.6 Example 5 10 1.2 1:1.02 74.9 Example 6 20 1.2 1:1.02 72.5 Example 7 30 1.2 1:1.02 72.9 Example 8 50 1.2 1:1.02 72.3 Example 9 One 5.5 1:1.02 72.4 Example 10 10 2.2 0.99 : 1.02 70.8 Example 11 50 2.2 0.95 : 1.02 58.0 Comparative Example 1 0 - 1:1.02 66.4 Comparative Example 2 5 5.5 1:1.02 60.0 Comparative Example 3 10 5.5 1:1.02 41.0 Comparative Example 4 20 5.5 1:1.02 29.3 Comparative Example 5 30 5.5 1:1.02 14.0 Comparative Example 6 10 2.2 1:1.02 57.2 Comparative Example 7 50 2.2 0.97 : 1.02 51.8

Referring to Table 1, according to Examples 1 to 11 and Comparative Examples 1 to 7, the content of the filler included in the composite material, the content of sulfur included in the filler, and the ratio of the precursor ([Na ₂ S]:[DCB]) It can be seen that the polymerization yield of polyphenylene sulfide changes greatly according to the In particular, referring to Example 5 and Comparative Example 6, it can be seen that the yield decreases from about 75% to about 57% when the content of sulfur contained in the filler is increased from 1.2% by weight to 2.2% by weight.

On the other hand, referring to Example 5, Comparative Example 6, and Example 10, even if the sulfur content included in the filler is increased to 2.2% by weight, when the mole number of sodium sulfide in the mole ratio of the precursor is lowered within the range of 0.95 to 1 It can be seen that the yield is again greatly improved.

In addition, referring to Table 1, it can be seen that in the case of manufacturing a composite material according to the present invention, the yield can be raised to 55% or more even when the content of the filler included in the composite material is as high as 10% to 50% by weight. there is.

Evaluation example 1 : of composite thermogravimetry

The thermogravimetric analysis behavior of the composite materials according to Examples 1 to 8 and Comparative Example 1 was analyzed. 1 shows the results of Comparative Example 1 and Examples 1 to 4. 2 shows the results of Examples 5 to 8. In addition, the thermal decomposition temperature and residual amount of each composite material are shown in Table 2.

Thermogravimetric analysis is a method of analyzing the weight loss caused by temperature by heating a sample at a constant temperature increase rate. The thermal decomposition temperature is a temperature at which the weight of S-rGO is reduced by 5% due to heat by raising the temperature to 900 ° C at a heating rate of 10 ° C per minute in a nitrogen (N ₂ ) atmosphere. Residual amount (Char yield) is the remaining amount after thermal decomposition after 900 ℃.

As shown in FIGS. 1, 2 and Table 2, as the amount of filler increased from Comparative Example 1 to Example 1 to Example 8 as a result of thermogravimetric analysis, the thermal decomposition temperature decreased due to the influence of S-rGO. It can be seen that the remaining amount (Char yield) increases.

Evaluation example 2 : Analysis of electrical conductivity of composites

Electrical conductivity of the composite materials according to Examples 1 to 8 and Comparative Example 1 was measured. The results are shown in Table 2.

식으로 전기전도도로 계산하였다. 여기서 t는 시편의 두께, R_s는 면저항, ρ_s는 비저항, σ_s는 전기전도도이다. 비교예1은 저항이 높아 전기전도도의 측정이 불가하였다. 한편, S-rGO의 함량이 높아짐에 따라, 정확히는 복합재의 S-rGO 함량이 10중량% 내지 50중량%일 때, 상기 복합재의 전기전도도는 1.5 S/m 이상, 가장 높게는 371 S/m까지 측정되었다. 다만, 전기전도도는 필러의 투입량 등에 따라 변화하는 것으로서, 본 발명에 따른 복합재의 전기전도도가 위 수치 범위에 한정되는 것은 아니고, 1 X 10^-8 S/cm 이상, 또는 1 X 10^-6 S/cm 이상, 또는 1 X 10^-4 S/cm 이상 등일 수 있다.For the measurement of electrical conductivity, specimens were prepared using hot-press equipment, and the sheet resistance value was measured through the 4-probe method and converted to electrical conductivity. the measured sheet resistance value

The electrical conductivity was calculated using the formula. where t is the thickness of the specimen, R _s is the sheet resistance, ρ _s is the resistivity, and σ _s is the electrical conductivity. Comparative Example 1 had high resistance, so it was impossible to measure electrical conductivity. On the other hand, as the content of S-rGO increases, precisely when the S-rGO content of the composite material is 10% to 50% by weight, the electrical conductivity of the composite material is 1.5 S/m or more, and up to 371 S/m at the highest. has been measured However, the electrical conductivity changes depending on the input amount of the filler, etc., and the electrical conductivity of the composite material according to the present invention is not limited to the above numerical range, and is 1 X 10 ^-8 S / cm or more, or 1 X 10 ^-6 S / cm or more, or 1 X 10 ^-4 S/cm or more, and the like.

Evaluation example 3 : Analysis of thermal conductivity of composites

Thermal conductivity of the composite materials according to Examples 1 to 8 and Comparative Example 1 was measured. The results are shown in Table 2.

Specimens were prepared using hot-press equipment to measure thermal conductivity. The thermal conductivity of the prepared specimen was measured using a biaxial thermal conductivity measuring instrument (Hot disc).

From Comparative Example 1 to Examples 1 to 8, the thermal conductivity increased due to the influence of S-rGO as the amount of filler increased, and the thermal conductivity of the composite material when the amount of filler was 10% to 50% by weight was measured above 0.3 W/mK, the highest being about 0.46 W/mK. Specifically, when the input amount of the filler was 30% by weight, the thermal conductivity increased by 2.1 times compared to Comparative Example 1 due to the influence of S-rGO.

Evaluation example 4 : Analysis of flame retardancy of composites

A temperature-heat release rate graph of the composite materials according to Examples 1 to 8 and Comparative Example 1 is shown in FIG. 3, and heat release capacity per unit mass is shown in Table 2.

The flame retardancy analysis was performed using a microcalorimeter, and the temperature was raised to 800° C. at a rate of 1° C. per second to confirm the change in heat release rate (HRR) according to the temperature. As the content of the filler increased from Comparative Example 1 to Example 1 to Example 8, the heat dissipation value decreased to 180 W/g or less due to the influence of S-rGO, and when the filler content was 50% by weight, 100 W / g or less.

Filler dosage (% by weight) pyrolysis temperature
(T _d 5%, ℃) balance
(Char yield, %) Thermal Conductivity (W/mK) Electrical conductivity (S/m) HRC (W/g) Example 1 0.1 491.9 42.7 0.2427 - 170 Example 2 0.5 480.1 43.4 0.2344 - 175 Example 3 One 484.0 41.9 0.2355 - 171 Example 4 5 450.3 44.4 0.2643 - 159 Example 5 10 467.1 51.4 0.4352 1.59 157 Example 6 20 453.6 55.0 0.4657 31.2 132 Example 7 30 430.5 56.6 0.3224 229 109 Example 8 50 402.4 54.4 0.3379 371 84 Comparative Example 1 0 488.3 42.9 0.2246 - 190

The embodiments of the present invention described above should not be construed as limiting the technical spirit of the present invention. The protection scope of the present invention is limited only by the matters described in the claims, and those skilled in the art can improve and change the technical idea of the present invention in various forms. Therefore, these improvements and modifications will fall within the protection scope of the present invention as long as they are obvious to those skilled in the art.

Claims (19)

delete delete delete delete delete delete delete preparing a filler including a carbon material doped with sulfur; and
Preparing a composite material including a matrix including polyphenylene sulfide and a filler dispersed therein by adding sodium sulfide, dichlorobenzene, and the filler to a solvent and synthesizing in-situ,
The filler contains 1% to 5% by weight of sulfur,
The composite material includes the filler in an amount of 0.1% to 50% by weight,
The molar ratio of sodium sulfide and dichlorobenzene is 0.95 to 1: 1.02,
The method of manufacturing a composite material, characterized in that the molar ratio of sodium sulfide is lowered when the content of the filler included in the composite is 10% by weight or more and the content of sulfur included in the filler is 2% by weight or more. According to claim 8,
Preparing the filler may include preparing a mixture including carbon material and sulfur;
heat-treating the mixture to convert sulfur into molten sulfur and reacting the mixture; and
A method for producing a composite material comprising the steps of removing sulfur from the reaction product. According to claim 8,
The carbon material is a method for producing a composite material comprising at least one selected from the group consisting of graphene oxide, reduced graphene oxide, carbon nanotubes, carbon fibers, and combinations thereof. delete delete delete delete delete According to claim 8,
When the content of the filler contained in the composite material is 10% to 50% by weight, the yield of the polyphenylene sulfide is 55% or more. According to claim 8,
The thermal conductivity of the composite is a method for producing a composite of 0.3 W / mK or more. According to claim 8,
The electrical conductivity of the composite material is 1 X 10 ^-8 S / m or more manufacturing method of the composite material. According to claim 8,
Method for producing a composite material having a heat release capacity per unit mass of the composite material of 180 W / g or less.

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