JPH01240525A - Aromatic polyamide and resin composition thereof - Google Patents

Abstract

PURPOSE:To obtain the subject novel polymer, having a specific structure, intrinsic viscosity within a specific range and high thermal decomposition temperature, soluble in organic solvents and useful as a resin component of compositions for resin varnishes excellent in molding processability. CONSTITUTION:The objective polymer having recurring units expressed by formula I [Ar is formula II or III (R is halogen or 1-5C alkyl which may be substituted by the halogen; X is single bond, -O-, etc.; Y is -O-, -S-, etc.), etc.] and 0.3-5dl/g intrinsic viscosity. The above-mentioned polymer is obtained by reacting an aromatic diamine expressed by the formula H2N-Ar-NH2 (e.g., 2-chloro-7-phenylenediamine) with 4,4'-sulfonyldibenzoic acid (dichloride) in an aprotic polar organic solvent and/or phenolic solvent, normally at -20-+200 deg.C for 5min-50hr.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel aromatic polyamide and a resin composition containing the polyamide as an essential component.

[Prior art and its problems] Although wholly aromatic polyamide has excellent heat resistance and mechanical properties, it is difficult to mold. This is generally 300
This is because it does not melt easily because it has a glass transition point of 'C or higher, and it also has poor solubility in solvents.

Therefore, in order to use polyamide as a material,
It has been desired to maintain good heat resistance and improve moldability.

On the other hand, thermosetting varnishes such as epoxy resins and polyimide resins have traditionally been used as varnishes that require both heat resistance and solvent resistance. Must be heated and cured. For this reason, it cannot be applied to fields where the substrate cannot be heated to high temperatures, such as insulating protective films for electronic component circuits, alignment films for liquid crystal display elements based on plastic films, etc., and its uses have naturally been limited.

The present inventors have discovered that an aromatic polyamide with a specific structure, which has not been described in any literature, maintains a high thermal decomposition temperature and
We have discovered that the varnish that is soluble in organic solvents can fully satisfy the intended purpose, and that the varnish containing the polyamide as a resin component can be molded at low temperatures and in a short time. Based on this, the present invention has been completed.

That is, an object of the present invention is to provide a new and useful aromatic polyamide and a polyamide resin composition containing the polyamide as an essential resin component and useful as a resin varnish or the like having excellent moldability.

[Means for Solving the Problems] The polyamide according to the present invention has a repeating unit represented by the following general formula (I>), and has an intrinsic viscosity of 0.3 to 5.
．． It is characterized by being about 0 dl/q.

Represents a divalent group selected from -5-1-SO-1-3O2-1-CO-1. Y represents 10-1-S-1-SO- or -802-. R represents a halogen atom or an alkyl group having 1 to 5 carbon atoms which may be substituted with a halogen atom, and each may be the same or different. ] The above aromatic polyamide is produced by reacting 4,4°-sulfonyl dibenzoic acid or its dichloride with one or more aromatic diamines represented by general formula (II) in an organic solvent. Manufactured.

HN-Ar-NH2(II> [In the formula, Ar is the same as in the case of Ikkatsukuri.] The dicarboxylic acid component according to the present invention contains 4,4°-sulfonyl dibenzoic acid or its dichloride as an essential component. However, if necessary, one or more selected from 3,4°-sulfonyl dibenzoic acid, terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, naphthalene dicarboxylic acid, or their dichlorites can be used in combination.However,
In this case, 4,4 in the carboxylic acid component.

The proportion of -sulfonyl dibenzoic acid or its dichloride is suitably about 20 mol% or more, preferably 50 mol% or more. If it is less than about 20 mol %, undesirable situations will occur, such as the polyamide to be jq becomes difficult to dissolve in organic solvents, resulting in poor processability, and the thermal decomposition temperature and glass transition point are lowered, resulting in decreased heat resistance.

As the aromatic diamine represented by general formula (II),
Various compounds of the following types (A> to (D>) can be exemplified.

2-bromo-p-phenylenediamine, 2,4-diaminotoluene, 2.6-diaminotoluene, 2.5-diaminotoluene, 2.4-diaminobenzene, 4.4-diaminodiphenyl sulfide, 4.4 -Diaminobenzophenone, 4.4-diaminodiphenylsulfone, 4.4-diaminodiphenylsulfoxide, 4.4-diaminodiphenylmethane, 4.4°-diaminodiphenyldimethylmethane, 4.4
- Diaminodiphenylmethylethylmethane, 4.4-diaminodiphenyldiethylmethane, 4.4-diaminodiphenyldi(trifluoromethyl)methane, 3.3-diaminodiphenyl ether, 3.3-diaminodiphenyl sulfide, 3.3-diamino Benzophenone, 3.3°-diaminodiphenylsulfone, 3.3-diaminodiphenylsulfoxide, 3.3-diaminodiphenylmethane, 3.3-diaminodiphenyldimethylmethane, 3.3°
-diaminodiphenylmethylethylmethane, 3.3°-
Diaminodiphenyldiethylmethane, 3.3'-diaminodiphenyldi(trifluoromethyl)methane, 3.4-diaminodiphenyl ether, 3.4-diaminodiphenyl sulfide, 3.4'-diaminobenzophenone, 3.4-diaminodiphenyl Sulfone, 3.4°-diaminodiphenyl sulfoxide, 3.4-diaminodiphenylmethane, 3.4-diaminodiphenyldimethylmethane, 3.4-
Diaminodiphenylmethylethylmethane, 3.4°-diaminodiphenyldiethylmethane, 3.4°-diaminodiphenyldi(trifluoromethyl)methane, niline, 3.4′-(1)-phenylenediisopropylidene)dianiline, 3 .3'-(p-phenylene diisopropylidene) dianiline, 1.4°-bis(aminophenoxy)benzene, 1.
3-bis(p-aminophenoxy)benzene, 1.4-
Bis(aminophenoxythioether)benzene, 1.3-bis(p-aminophenoxythioether)benzene, 1.4'-bis(p-aminophenyl)benvin, 1.
3°-bis(aminophenyl)benzene, ・2.
2-bis[4-(p-aminophenoxythioether)
phenyl]propane, 2.2-bis[3-(aminophenoxythioether)phenyl]propane, 4.4°-bis(p-7minophenoxy)diphenylsulfone, 3.3′-bis(aminophenoxy)diphenylsulfone , 3.4"-bis(p-aminophenylthioether)diphenylsulfone, 4.4°-bis(p-aminophenylthioether)diphenylsulfone, 3.3"-bis(p-aminophenylthioether)diphenylsulfone, 3.4 “-bis(p-7 minophenylthioether) diphenylsulfon, 4.4°-bis(aminophenoxy) diphenyl ether, 3.3′-bis(p-aminophenoxy) diphenyl ether, 3.4°-bis (Aminophenoxy) diphenyl ether, 4.4°-bis(aminophenoxy) diphenyl sulfide, 3,3-bis(aminophenoxy) diphenyl sulfide, 3.4-bis(aminophenoxy) diphenyl sulfide, 4.4 °-Bis(p-7 minophenylthioether) diphenyl sulfide, 3.3゛-bis(p-aminophenylthioether) diphenyl sulfide, 3.4-bis(minophenylthioether) diphenyl sulfide, 4.4゛-bis (p-aminophenylthioether) diphenyl ether, 3.3°-bis(aminophenylthioether) diphenyl ether, 3.4″-bis(aminophenylthioether) diphenyl ether, 4.4″-bis(p-aminophenoxy)benzophenone , 3.3゛-bis(aminophenoxy)benzophenone, 3.4゛-bis(aminophenoxy)benzophenone, 4.4゛-bis(aminophenylthioether)benzophenone, 3.3°-bis(p- aminophenylthioether)benzophenone, 3.4゛-bis(p-aminophenylthioether)benzophenone, 4.4°-bis(p-aminophenylthioether)diphenyl, 3.3°-bis(p-aminophenylthioether)diphenyl , 3.4°-bis(aminophenylthioether)diphenyl, and meta monomers of each of the above diamines.

These diamines can be used alone or in combination of two or more. Furthermore, as long as the desired effects of the present invention can be obtained, other aromatic diamines may be used in combination.

The appropriate blending ratio of the dicarboxylic acid component to the aromatic diamine is preferably about 0.9 to 1.2 equivalents of the dicarboxylic acid component per 1 equivalent of the aromatic diamine.

Organic solvents applied as reaction media include N, N-
Dimethylformamide, N,N-diethylformamide, N,N-diethylacetamide (hereinafter abbreviated as rDMAcJ), N,N-diethylacetamide, N-methyl-2-pyrrolidone (hereinafter abbreviated as rNMPJ).
, dimethyl sulfoxide (rDMsOJ hereinafter), tetramethylurea, 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoramide, nitrobenzene, diglyme, tetrahydrofuran (rTH
It will be abbreviated as FJ. ), aprotic polar 41 solvents,
Examples include phenolic solvents such as phenol, cresol, dimethylphenol, chlorophenol, and bromophenol.

Further, other solvents can also be used in combination within the range in which the predetermined purpose is achieved. Examples of solvents that can be used in combination include glycol carbonate, ethylene glycol dimethyl ether, methyl cellosolve, dichloromethane, 1,2-dichloroethane, 1,1-dichlorobutane, trichloroethane, chlorobenzene, and dig[]rubenzene.

Furthermore, coexisting an acid acceptor such as pyridine or trimethylamine in the above organic solvent, or using a two-phase system with an alkaline aqueous solution in a solvent system that is immiscible with water, is effective in improving polymerization reactivity. It is true.

The temperature in the reaction is about -20 to 200'C, and the reaction time is about 5 minutes to 50 hours.

Alternatively, 4,4-sulfonyl dibenzoic acid and an aromatic diamine represented by the general formula (II) are heated at 20 to 200° in the above-mentioned solvent in combination with an aromatic phosphite and a pyridine derivative. The desired aromatic polyamide can also be produced by reacting with C for several minutes to several days.

Aromatic phosphites that can be applied to this method include triphenyl phosphite, diphenyl phosphite, and phosphorus.
Examples include tri-o-tolyl phosphoric acid, tri-m-tolyl phosphorous acid, tri-m-tolyl phosphorous acid, and the like. Further, examples of pyridine derivatives include pyridine and alkyl-substituted derivatives thereof.

The aromatic polyamide according to the present invention has a sufficiently large intrinsic viscosity [ηi] while maintaining high solubility in organic solvents.
nh ] (Polymer concentration: 0.5 g/100 d, Solvent: NMP, Measurement temperature: 30°C) (i.e., a sufficiently large molecular weight), and can usually present about 0.3 to 5.0 dl/y. . Furthermore, when the processability of polyamide is taken into consideration, it is preferable to set the intrinsic viscosity to about 0.4 to 2.0 dl/lj.

Such a polyamide is soluble in a single solvent or a mixture of two or more of the various organic solvents used as the reaction solvent, and its solubility is determined by selecting the type of aromatic diamine or dicarboxylic acid to be used. It can be adjusted as appropriate.

However, the polyamide is not soluble in common organic solvents such as gasoline, kerosene, benzene, toluene, aliphatic alcohols, acetone, methyl ethyl carbon, and various esters, and has excellent solvent resistance.

One of the objects of the present invention is to provide a polyamide resin composition obtained by dissolving a polyamide having a specific structure in a suitable organic solvent as described above.

Suitable organic solvents in the present invention include various solvents commonly used as reaction solvents for the polyamide.

The concentration of polyamide in the resin composition can be appropriately selected depending on its use, but is usually 1 to 40% by weight.
% by weight is used. If it is less than 1% by weight, it is unfavorable for economics, and if it exceeds 40% by weight, the composition may gel or its viscosity becomes too high, which reduces workability during molding, which is not preferable.

Another object of the present invention is to provide the above-mentioned polyamide resin composition, which has improved adhesion to a base material without impairing the heat resistance or mechanical properties of the polyamide by incorporating a silane coupling agent. be one of the.

It is presumed that the silane coupling agent in the composition migrates to the surface of the base material, modifies the surface, and improves the compatibility between the base material and the polyamide.

Applicable silane coupling agents include γ-glycidoxypropyltrimethoxysilane, γ-(2-aminoethyl)aminopropyltrimethoxysilane, γ-(2-aminoethyl)aminopropylmethyldimethoxysilane, γ- Methacryloxypropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, methylmethoxysilanemethyltriethoxysilane, vinyltriacetoxysilane, N-p-<N--vinylbenzylaminoethyl)-γ-
Aminopropyltrimethoxysilane, γ-chloropropyltrimethoxysilane, hexamethyldisilazane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, γ-anilino Propyltrimethoxysilane, vinyltrimethoxysilane, γ-chloropropylmethyldimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, methyltrichlorosilane, dimethyldichlorosilane, trimethylchlorosilane, γ-aminopropylethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane Examples include chlorosilane, vinyltri(β-methoxyethoxy)silane, and the like.

The amount of the silane coupling agent added is usually about 0.1 to 20% by weight, preferably 1 to 10% by weight, based on the polyamide. 0. If it is less than about 1% by weight, it is difficult to obtain the desired effect, and if it exceeds about 20% by weight♀
Even if it is blended, no significant difference in effectiveness is observed, which is economically disadvantageous.

The silane coupling agent may be added directly to the polyamide resin solution, but it may also be added as a solution prepared by dissolving it in a suitable solvent, such as the above-mentioned aprotic polar organic solvent or phenolic solvent. .

The composition formed by dissolving the polyamide according to the present invention is a relatively low-viscosity solution that is fluid at room temperature, and therefore is extremely easy to handle and mold.

Furthermore, it has high stability in a solution state and can be stored at room temperature for a long period of time without causing changes in viscosity or deterioration such as precipitation of insoluble matter.

Such a polyamide resin solution can be cast or spin-coated onto the smooth surface of a base material such as a glass plate or metal plate, and then removed by heating or other methods to easily form a yellow-brown transparent solution. A polyamide film is obtained.

This film has high mechanical strength and is highly flexible, and for example, a film with a thickness of 30 μm can sufficiently withstand repeated bending tests. In addition, the thermal decomposition temperature is high,
It shows good heat resistance and good chemical resistance. Further, at temperatures above the melting temperature, it exhibits thermoplasticity and can be heat-pressed and compression-molded into films.

In particular, a polyamide resin composition containing a silane coupling agent can form a coating film in a short time at a relatively low temperature by simply volatilizing the solvent, and also
For example, it has excellent adhesion to metals such as glass, aluminum, silicon, copper, nickel, and iron, their oxides, and plastics such as polypropylene, polyethylene terephthalate, and epoxy. This is suitable for applications in fields where substrates are difficult to heat at high temperatures, such as surface protective films for semiconductors, insulating protective films for electronic component circuits, and alignment films for liquid crystal display elements using plastic as a base material.

As described above, the polyamide resin composition obtained by the present invention can be used not only for heat-resistant films but also for heat-resistant varnishes, laminates, adhesives, various electrical and electronic materials, etc. It is used for flexible wiring boards, printed wiring boards, tape carriers, surface protection films or interlayer insulation films for semiconductor integrated circuit elements, covering materials for enameled electric wires, various laminate gaskets, etc.

[Example] Hereinafter, the present invention will be described in detail with reference to Examples.

The intrinsic viscosity, solution viscosity, thermal decomposition temperature, softening point, tensile strength, elastic modulus, and solubility in organic solvents of the polyamide in each example were measured and evaluated by the following methods.

(1) Intrinsic viscosity of polyamide [77 inh] (d
7/y> Polyamide 0.57 was dissolved in 100d of NMP, and using an Ostwald viscometer, the falling time of the sample solution (t) (seconds) and the falling time of the solvent (1o) were measured at a temperature of 30°C.
(seconds) and was determined using the following formula.

ηinh = i n (t/t□) / 0.5
(2) Polyamide solution viscosity (PS) Measured using an E-type viscometer at a polyamide concentration of 20% by weight and a temperature of 25°C.

(3) Thermal decomposition temperature ('C) of polyamide (hereinafter r - r
Abbreviated as GJ. ) Differential thermal balance analyzer (HER) IAL ANALYZ
ERDT-30'', manufactured by Shimadzu Corporation, in the air.
The temperature is increased at a rate of 0'C/min, and the weight is 10% lower than the weight at the start of heating.
The temperature at which the weight decreased by % by weight was determined.

(4) Softening point ('C) of polyamide (rTMAJ
). ) Differential thermal balance analyzer (rTH[R)IAL ANALY
ZERDT-30'' (manufactured by Ajishimazu Corporation), the temperature was raised in air at a rate of 10'C/min, and the softening point was measured in needle penetration mode.

(5) Tensile strength <KFl/mA>, elastic modulus (KJ/m
)Tensile tester (rlNsTf?ON MODEL-1
122J, In5tron Japan Compa
ny Ltd, l) was used. Width 1cm.

The upper and lower 1 cm of each 8 cm long film test piece were fixed, and the measurement was carried out under the conditions of a load of 5 kg and a tensile speed of 10 #/min.

(6) Solubility in organic solvents Polyamide corresponding to 3% by weight was added to various organic solvents and evaluated on the following three levels.

++: Dissolved at room temperature, +: Dissolved while waiting for heat - di-insoluble Example 1 3.4'-diaminodiphenyl ether 1.00 g (5
mmol) in 10 d of NMP and placed on dry ice.
Completely frozen on an acetone bath. Diphenylsulfone-4,4-dicarboxylic acid dichloride 1.
Add 71 g (5 mmol) and incubate at 0°C under nitrogen atmosphere for 3 hours.
The reaction was carried out with stirring for a period of time. After the reaction was completed, the polymerization solution was poured into water to obtain a polyamide. The infrared absorption spectrum of this product is shown in Figure 1, and the intrinsic viscosity, thermal decomposition temperature,
The measurement results of the softening point are listed in Table 1 along with the mechanical properties.

Furthermore, the solubility in other organic solvents is shown in Table 2.

Note that the viscosity of the NMP solution was 30 PS.

Example 2 1.00 g (5 mmol) of 3.4-diaminodiphenyl ether, 11.539 (5 mmol) of diphenylsulfone-4,4°-dicarvone, 3.10y (10 mmol) of triphenyl phosphite, 2.0 g (5 mmol) of pyridine. 5m, 0.50 g of lithium chloride, and NMPlod were reacted under a nitrogen atmosphere at 100° C. for 3 hours with stirring. After the reaction was completed, the obtained solution was poured into methanol to obtain a polyamide. The physical properties of this product are shown in Tables 1 and 2.

Note that the viscosity of the DMSO solution was 35 PS.

Example 3 1.72 g (5 mmol) of 4.4°-(p-phenylene diisopropylidene) dianiline was dissolved in 10 d of NMP and completely frozen on a dry ice-acetone bath.

1.719 (5 mmol) of diphenylsulfone-4,4°-cafrefonic acid dichloride was added to the resulting solid, and the mixture was reacted at 0° C. under a nitrogen atmosphere with stirring for 3 hours.

After the reaction was completed, the polymerization solution was poured into water to obtain a polyamide. The infrared absorption spectrum of this product is shown in FIG. 2, and the various physical properties are listed in Tables 1 and 2. Note that the viscosity of the m-cresol solution was 33 PS.

Example 4 2.16 g (5 mmol) of 4.4°-bis(aminophenoxy)diphenylsulfone and 1.53 g (5 mmol) of 'diphenylsulfone-4,4°-dicarboxylic acid were prepared according to Example 2. Polyamide was obtained by polymerization. The infrared absorption spectrum of this product is shown in FIG. 3, and the various physical properties are listed in Tables 1 and 2. Note that the viscosity of the DMAC solution was 40 PS.

Example 5 2-chloro-phenylenediamine 0.71tj (5 mmol), diphenylsulfone-4,4-dicarboxylic acid 1
1. OOg (5 mmol), trinoenylsulfite3.
10 g (10 mmol), 2.5 mf of pyridine! , 0.50 g of calcium chloride, and NM Ploml were reacted under a nitrogen atmosphere at 100° C. with stirring for 3 hours. After the reaction was completed, the obtained solution was poured into methanol to obtain a polyamide. The physical properties of this product are shown in Tables 1 and 2. Note that the viscosity of the DMF solution was 40 PS.

Examples 6 to 29 Various diamines were selected and polyamides were synthesized according to Example 1. Table 3 shows the intrinsic viscosity, thermal properties, and solubility in organic solvents of the polyamide obtained.

The infrared absorption spectrum of the polyamide obtained in Example 11 is shown in FIG. 4, and the infrared absorption spectrum of the polyamide obtained in Example 13 is shown in FIG.

Example 30 10 g of the polyamide obtained in Example 1 and 0.59 g of γ-glycidoxypropylmethoxysilane were dissolved in 90 g of NMP and cast onto a glass plate. This is done under reduced pressure.
It was heated at 80°C, then at 150°C and 200°C for 1 hour each, and used as a test piece for an adhesion test.

For the adhesion test, 100 squares of 11 ra square were placed on the coating film in accordance with JIS D-0202, and the test was carried out at 2 atm.
After being placed in a pressure cooker at 121℃ for 10 hours,
Cellophane tape was pasted and rapidly peeled off, and the number of pieces peeled off was evaluated (cellophane tape peel test). As a result,
100 (the number of squares that peeled off was 0. On the other hand, when the silane coupling agent was not coexisting, the number of squares that peeled off was 85.

Further, the above test piece was further heated at 250 to 300°C for 1 hour and the thermal decomposition temperature was measured at 465°C.

Example 31 A polyamide varnish was prepared by dissolving 10 g of the polyamide obtained in Example 3 and γ-mercaptopropyltrimethoxysilane in DMAc4(l). The adhesion and thermal decomposition temperature of this material were measured according to Example 30. As a result, the number of squares that peeled off was O. On the other hand, when the silane coupling agent was not present, the number of squares that peeled off was 77. Also, the thermal decomposition temperature was 461°C. .

Example 32 Polyamide 107 obtained in Example 4 and γ-(2-aminoethyl)aminopropyltrimethoxysilane 17 were dissolved in m-cresol 90s to prepare a polyamide varnish. Example 30: Adhesion and thermal decomposition temperature of this material
Measured according to. As a result, the number of peeled squares is O
Met. On the other hand, when the silane coupling agent was not present, the number of peeled squares was 89. Moreover, the thermal decomposition temperature was 486°C.

Example 33 Polyamide 53 obtained in Example 6 and γ-chloropropyltrimethoxysilane O. ] 3 was dissolved in 50 g of NMP to prepare a polyamide varnish.

The adhesion and thermal decomposition temperature of this product were measured according to Example 30. As a result, the number of squares that came off was O. On the other hand, when the silane coupling agent was not present, the number of peeled squares was 91. Also, the thermal decomposition temperature is 4
The temperature was 72°C.

Example 34 Polyamide 53 obtained in Example 9 and 0.33 gamma-glycidoxypropyltrimethoxysilane were dissolved in 1,3-dimethyl-2-imidazolidinone 409 to prepare a polyamide varnish. Adhesion and heat content of this material 11/
i' temperature was measured according to Example 30. As a result, the number of peeled squares was O. On the other hand, when the silane coupling agent is not present, the number of squares drawn is 82.
Met. Moreover, the thermal decomposition temperature was 466°C.

Examples 35-44 Examples 9, 16, 18-22, 24, 26 and 1 in 2B
A polyamide varnish was prepared by dissolving 57 of each polyamide and 0.33 of γ-glycidoxypropyltrimethoxysilane in 45 g of NMP. The adhesion and thermal decomposition temperature of this product were measured according to Example 30. The results obtained are listed in Table 4.

[Effects of the Invention] The aromatic polyamide according to the present invention has high heat resistance and is soluble in certain major solvents, so it can be molded in a solution state. Moreover, since it does not dissolve in ordinary organic solvents such as hydrocarbons, aliphatic alcohols, ketones, and esters, the obtained molded product also has excellent solvent resistance.

In addition, the aromatic polyamide resin composition obtained by dissolving the polyamide in an organic solvent does not require any special film-forming treatment, and can form a film or coating in a short time at low temperatures by simply volatilizing the solvent. It is possible.

Furthermore, the polyamide resin composition containing a silane coupling agent has excellent adhesion to various substrates.

[Brief explanation of the drawing]

FIG. 1 shows an infrared absorption spectrum of the polyamide obtained in Example 1. FIG. 2 shows the infrared absorption spectrum of the polyamide obtained in Example 3. FIG. 3 shows the infrared absorption spectrum of the polyamide obtained in Example 4. FIG. 4 shows an infrared absorption spectrum of the polyamide obtained in Example 11. FIG. 5 shows an infrared absorption spectrum of the polyamide obtained in Example 13.

Claims (1)

[Claims] 1. A polyamide having a repeating unit represented by the general formula (I) and having an intrinsic viscosity of about 0.3 to 5.0 dl/g. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, Ar is ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲
There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents. Here, X is a single bond or -O-, -S-, -
SO-, -SO_2-, -CO-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables etc. ▼ Represents a divalent group selected from. Y is -O-, -S-,
-SO- or -SO_2-. R represents a halogen atom or an alkyl group having 1 to 5 carbon atoms which may be substituted with a halogen atom, and may be the same or different. 2. A polyamide resin composition comprising at least one polyamide according to claim 1 dissolved in an organic solvent. 3. Add 0.1 silane coupling agent to polyamide
The polyamide resin composition according to claim 2, wherein the polyamide resin composition is blended in an amount of about 20% by weight. 4. One or more aromatic diamines represented by general formula (II) and 4,4'-sulfonyl dibenzoic acid or 4,4'-sulfonyl dibenzoic acid or
, 4'-sulfonyl dibenzoic acid dichloride in an aprotic polar organic solvent and/or a phenolic solvent. A method for producing a resin composition. H_2N-Ar-NH_2(II) [Wherein, Ar is the same as in general formula (I). ]