JP2583665B2 - Polyamide resin and its resin composition - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a novel heat-meltable aromatic polyamide having high heat resistance.

Further, the present invention relates to a novel polyamide resin composition having excellent dimensional stability and mechanical properties and excellent workability.

[Conventional technology]

Conventionally, aromatic polyamides obtained by reacting an aromatic diamine or aromatic diisocyanate with an aromatic dicarboxylic acid or a derivative thereof have a variety of excellent physical properties and good heat resistance. Is expected to be widely used in the field where is required.

However, although there have been many aromatic polyamides which have been developed so far, they have excellent mechanical properties and heat resistance, but all have a drawback that they are poor in moldability and high in water absorption.

For example, formula (III) An aromatic polyamide having a basic skeleton represented by the following formula (DuPont product: Kevlar) has excellent properties such as flame retardancy, heat resistance, high tension and high elastic modulus. However, this aromatic polyamide does not have a clear glass transition temperature, its thermal decomposition temperature is around 430 ° C, and its processing temperature and thermal decomposition temperature are close to each other, making it difficult to use as a molding material There were drawbacks. Therefore, it is only used in the field of fibers by wet spinning or pulp. Further, the water absorption is as high as 4.5%, and it is apparent that the use of such a material as a base material for electric / electronic parts adversely affects dimensional stability, insulation properties, solder heat resistance and the like.

[Problems to be solved by the present invention]

An object of the present invention is to provide an aromatic polyamide having excellent processability and low water absorption and a composition thereof, in addition to the excellent heat resistance inherent to the aromatic polyamide.

Another object of the present invention is to provide a novel resin composition which improves the mechanical strength and dimensional stability of the polyamide and further has excellent processability.

[Means for solving the problem]

The present inventors have conducted intensive studies to achieve the above-mentioned object, and as a result, have found a novel aromatic polyamide having desired performance and a resin composition thereof, and have completed the present invention.

That is, the present invention provides: (1) Formula (I) (Wherein X is a condensed polycyclic aromatic group or Or one or more groups selected from the group consisting of Wherein Y is a direct bond, -O-, -S-, -SO
_{2 -, - CO -, -} CH 2 -, R represents an alkyl group, an alkoxy group, or a halogen group having 1 to 4 carbon atoms, a phenyl group, a represents 0, 1 or 2, and b represents 0 or an integer of 1 to 4. Also, n is 1 to
Represents an integer of 1000. (2) a thermostable polyamide having a repeating unit represented by the formula (1) as a basic skeleton and having a polymer terminal sealed with a monovalent amine or a monovalent carboxylic acid or a carboxylic acid derivative. Formula (I) (Wherein X is a condensed polycyclic aromatic group or Or one or more groups selected from the group consisting of Wherein Y is a direct bond, -O-, -S-, -SO
_{2 -, - CO -, -} CH 2 -, R represents an alkyl group, an alkoxy group, or a halogen group having 1 to 4 carbon atoms, a phenyl group, a represents 0, 1 or 2, and b represents 0 or an integer of 1 to 4. Also, n is 1 to
Represents an integer of 1000. The polyamide resin composition comprises 100 parts by weight of the polyamide represented by the formula (1) and 5 to 100 parts by weight of the fibrous reinforcing material.

The aromatic polyamide of the present invention has a diamine component represented by the formula (II): Using a diamine represented by the formula, that is, 4,4'-bis (3-aminophenoxy) -3,3 ', 5,5'-tetramethylbiphenyl, and polymerizing this with an aromatic dicarboxylic acid or a derivative thereof. can get. Further, the polyamide resin composition of the present invention can be obtained by adding a fibrous reinforcing material to the polyamide of the present invention. That is, the polyamide of the present invention and its resin composition are characterized by using 4,4'-bis (3-aminophenoxy) -3,3 ', 5,5'-tetramethylbiphenyl as a diamine component, and originally, A thermoplastic aromatic polyamide having excellent processability in addition to the heat resistance of the aromatic polyamide, and a resin composition thereof.

Since the aromatic polyamide and its resin composition are thermoplastic in addition to excellent heat resistance, they can be extrusion-molded and injection-molded. Furthermore, it can be expected to be used for multipurpose applications as a raw material for high-strength, high heat-resistant fibers by a melt spinning method, and is extremely useful.

The polyamide of the present invention is a polyamide using the above-mentioned diamine as a raw material, but other diamines may be mixed and used as long as good physical properties of the polyamide are not impaired.

Examples of the diamine that can be used by mixing include, for example, o-
Phenylenediamine, m-phenylenediamine, p-phenylenediamine, m-aminobenzylamine, p-aminobenzylamine, 2-chloro-1,2-phenylenediamine, 4-chloro-1,2-phenylenediamine, 2,3 −
Diaminotoluene, 2,4-diaminotoluene, 2,5-diaminotoluene, 2,6-diaminotoluene, 3,4-diaminotoluene, 2-methoxy-1,4-phenylenediamine,
4-methoxy-1,2-phenylenediamine, 4-methoxy-1,3-phenylenediamine, benzidine, 3,3'-dichlorobenzidine, 3,3'-dimethylbenzidine, 3,3 '
-Dimethoxybenzidine, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4 '
-Diaminodiphenyl ether, 3,3'-diaminodiphenyl sulfide, 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 3,3'-
Diaminodiphenylsulfoxide, 3,4'-diaminodiphenylsulfoxide, 4,4'-diaminodiphenylsulfoxide, 3,3'-diaminodiphenylsulfone,
4'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfone, 3,3'-diaminobenzophenone,
3,4'-diaminobenzophenone, 4,4'-diaminobenzophenone, 3,3'-diaminodiphenylmethane, 3,4 '
-Diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, bis [4- (3-aminophenoxy) phenyl] methane, bis [4- (4-aminophenoxy) phenyl] methane, 1,1-bis [4- (3 -Aminophenoxy) phenyl] ethane, 1,1-bis [4- (4-aminophenoxy) phenyl] ethane, 1,2-bis [4-
(3-aminophenoxy) phenyl] ethane, 1,2-bis [4- (4-aminophenoxy) phenyl] ethane,
2,2-bis [4- (3-aminophenoxy) phenyl]
Propane, 2,2-bis [4- (4-aminophenoxy)
Phenyl] propane, 2,2-bis [4- (3-aminophenoxy) phenyl] butane, 2,2-bis [4- (4-
Aminophenoxy) phenyl] butane, 2,2-bis [4
-(3-aminophenoxy) phenyl] -1,1,1,3,3,3
-Hexafluoropropane, 2,2-bis [4- (4-aminophenoxy) phenyl] -1,1,1,3,3,3-hexafluoropropane, 1,3-bis (3-aminophenoxy)
Benzene, 1,3-bis (4-aminophenoxy) benzene, 1,4-bis (3-aminophenoxy) benzene, 1,4
-Bis (4-aminophenoxy) benzene, 4,4'-bis (3-aminophenoxy) biphenyl, 4,4'-bis (4-aminophenoxy) biphenyl, bis [4- (3
-Aminophenoxy) phenyl] ketone, bis [4-
(4-aminophenoxy) phenyl] ketone, bis [4
-(3-Aminophenoxy) phenyl] sulfide, bis [4- (4-aminophenoxy) phenyl] sulfide, bis [4- (3-aminophenoxy) phenyl] sulfoxide, bis [4- (4-aminophenoxy) phenyl ] Sulfoxide, bis [4- (3-aminophenoxy) phenyl] sulfone, bis [4- (4-aminophenoxy) phenyl] sulfone, bis [4- (3-aminophenoxy) phenyl] ether, bis [4- ( 4-aminophenoxy) phenyl] ether, 1,4-bis [4
-(3-aminophenoxy) benzoyl] benzene, 1,
3-bis [4- (3-aminophenoxy) benzoyl]
Benzene, 4,4'-bis [3- (4-aminophenoxy) benzoyl] diphenyl ether, 4,4'-bis [3- (3-aminophenoxy) benzoyl] diphenyl ether, 4,4'-bis [4- ( 4-amino-α, α
-Dimethylbenzyl) phenoxy] benzophenone, 4,
4'-bis [4- (4-amino-α, α-dimethylbenzyl) phenoxy] diphenylsulfone, bis [4-
{4- (4-aminophenoxy) phenoxy} phenyl] ketone, bis [4- {4- (4-aminophenoxy) phenoxy} phenyl] sulfone 1,4-bis [4-
(4-aminophenoxy) -α, α-dimethylbenzyl] benzene, 1,3-bis [4- (4-aminophenoxy) -α, α-dimethylbenzyl] benzene, and the like. Two or more kinds are used in combination.

The method for producing the aromatic polyamide of the present invention is not particularly limited, and a conventionally known method can be employed.

For example, the method according to claims 2 to 4. The aromatic diamine used in this method is 4,4'-bis (3-aminophenoxy) -3,3 ', 5,5'-tetramethylbiphenyl.

The aromatic dicarboxylic acids used in the method of claim 2 are aromatic dicarboxylic acid dihalides. For example, phthalic dichloride, phthalic dibromide, methyl phthalic dichloride, methyl phthalic dibromide, ethyl phthalic dichloride, ethyl phthalic dibromide, methoxy phthalic dichloride, methoxy phthalic dibromide, ethoxy phthalic dichloride, ethoxy phthalic acid Dibromides, chlorophthalic dichlorides, chlorophthalic dibromides, bromophthalic dichlorides, bromophthalic dibromides,
Isophthalic acid dichloride, isophthalic acid dibromide,
Methyl isophthalic dichloride, methyl isophthalic dibromide, ethyl isophthalic dichloride, ethyl isophthalic dibromide, methoxy isophthalic dichloride, methoxy isophthalic dibromide, ethoxy isophthalic dichloride, ethoxy isophthalic dibromide, chloroisophthal Acid dichlorides, chloroisophthalic acid dibromide, bromoisophthalic acid dichloride, bromoisophthalic acid dibromide, terephthalic acid dichloride, terephthalic acid dibromide, methyl terephthalic acid dichloride, methyl terephthalic acid dibromide, ethyl terephthalic acid dichloride, ethyl terephthalate Acid dibromide, methoxyterephthalic acid dichloride, methoxyterephthalic acid dibromide, ethoxyterephthalic acid dichloride Ethoxyterephthalic acid dibromide, chloroterephthalic acid dichloride, chloroterephthalic acid dibromide, bromoterephthalic acid dichloride, bromoterephthalic acid dibromide, 4,4'-biphenyldicarboxylic acid dichloride, 4,4'-biphenyldicarboxylic acid dibromide , 4,4'-diphenyl ether dicarboxylic acid dichloride, 4,4'-biphenyl ether dicarboxylic acid dibromide, 4,4'-benzophenone dicarboxylic acid dichloride, 4,4'-benzophenone dicarboxylic acid dibromide, 4,4'-diphenyl sulfide dicarboxylic acid Acid dichloride, 4,4'-diphenyl sulfide dicarboxylic acid dibromide, 4,4'-diphenyl sulfone dicarboxylic acid dichloride, 4,4'-diphenyl sulfone dicarboxylic acid dibromide, 4,4'-diphenyl methane dicarboxylic acid dichloride 4,4'-diphenylmethanedicarboxylic acid dibromide, 2,2-bis (4-chloroformylphenyl) propane, 2,2-bis (4-bromoformylphenyl) propane, 2,2-bis (4-chloroformyl) Phenyl) -1,1,1,3,3,3-hexafluoropropane, 2,2-bis (4-bromoformylphenyl) -1,1,1,3,3,3-hexafluoropropane, 4-naphthalenedicarboxylic dichloride, 1,4-naphthalenedicarboxylic dibromide, 2,3-naphthalenedicarboxylic dichloride, 2,3-naphthalenedicarboxylic dibromide, 2,6-naphthalenedicarboxylic dichloride, 2,6-naphthalenedicarboxylic acid Dibromide and the like. These aromatic dicarboxylic dihalides are used alone or in combination of two or more.

In the method according to the third aspect, an aromatic dicarboxylic acid is used. For example, phthalic acid, methylphthalic acid, ethylphthalic acid, methoxyphthalic acid, ethoxyphthalic acid, chlorophthalic acid, bromophthalic acid, isophthalic acid, methylisophthalic acid, ethylisophthalic acid, methoxyisophthalic acid, ethoxyisophthalic acid, chloroisophthalic acid, bromoisophthalic acid Acids, terephthalic acid, methyl terephthalic acid, ethyl terephthalic acid, methoxy terephthalic acid, ethoxy terephthalic acid, chloroterephthalic acid, bromoterephthalic acid, 2,2'-biphenyldicarboxylic acid, 4,4'-biphenyldicarboxylic acid, 4,4 '-Diphenyl ether dicarboxylic acid, 4,4'-
Diphenyl sulfide dicarboxylic acid, 4,4'-benzophenone dicarboxylic acid, 4,4'-diphenyl sulfone dicarboxylic acid, 4,4'-diphenyl methane dicarboxylic acid, 2,2
-Bis (4-carboxyphenyl) propane, 2,2-bis (4-carboxyphenyl) -1,1,1,3,3,3-hexafluoropropane, 1,4-naphthalenedicarboxylic acid, 2,3
-Naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid and the like. These aromatic dicarboxylic acids are used alone or in combination of two or more.

Further, in the method of claim 4, for example, dimethyl phthalate, diethyl phthalate, dipropyl phthalate, diisopropyl phthalate, dibutyl phthalate, diisobutyl phthalate, dimethyl isophthalate, diethyl isophthalate,
Dipropyl isophthalate, diisopropyl isophthalate, dibutyl isophthalate, diisobutyl isophthalate, dimethyl terephthalate, diethyl terephthalate, dipropyl terephthalate, diisopropyl terephthalate,
Dibutyl terephthalate, diisobutyl terephthalate, 4,
Dimethyl 4'-biphenyldicarboxylate, diethyl 4,4'-biphenyldicarboxylate, dipropyl 4,4'-biphenyldicarboxylate, diisopropyl 4,4'-biphenyldicarboxylate, dibutyl 4,4'-biphenyldicarboxylate, Diisobutyl 4'-biphenyldicarboxylate, 4,
Dimethyl 4'-diphenyletherdicarboxylate, 4,4 '
-Diethyl diphenyl ether dicarboxylate, 4,4'-
Dipropyl diphenyl ether dicarboxylate, 4,4'-
Diisopropyl diphenyl ether dicarboxylate, 4,
Dibutyl 4'-diphenyl ether dicarboxylate, 4,4 '
Diisobutyl diphenyl ether dicarboxylate, 4,
Dimethyl 4'-diphenylsulfidedicarboxylate, 4,
Diethyl 4'-diphenylsulfidedicarboxylate, 4,
4'-diphenyl sulfide dicarboxylate dipropyl,
Diisopropyl 4,4'-diphenyl sulfide dicarboxylate, dibutyl 4,4'-diphenyl sulfide dicarboxylate, diisobutyl 4,4'-diphenyl sulfide dicarboxylate, dimethyl 4,4'-benzophenone dicarboxylate, 4,4'-benzophenone dicarboxylate Diethyl acid salt, 4,
Dipropyl 4'-benzophenonedicarboxylate, 4,4'-
Diisopropyl benzophenonedicarboxylate, 4,4'-
Dibutyl benzophenone dicarboxylate, diisobutyl 4,4'-benzophenone dicarboxylate, dimethyl 4,4'-diphenylsulfone dicarboxylate, diethyl 4,4'-diphenylsulfone dicarboxylate, dipropyl 4,4'-diphenylsulfone dicarboxylate, 4, Diisopropyl 4'-diphenylsulfonedicarboxylate, dibutyl 4,4'-diphenylsulfonedicarboxylate, diisobutyl 4,4'-diphenylsulfonedicarboxylate, dimethyl 4,4'-diphenylmethanedicarboxylate, diethyl 4,4'-diphenylmethanedicarboxylate Dipropyl 4,4'-diphenylmethanedicarboxylate, diisopropyl 4,4'-diphenylmethanedicarboxylate, dibutyl 4,4'-diphenylmethanedicarboxylate, diisobutyl 4,4'-diphenylmethanedicarboxylate, 2,2-bis (4-methoxy Carbonyl phenyl) propane, 2,2-bis (4-ethoxycarbonyl phenyl) propane, 2,2-bis (4-propoxycarbonyl) propane, 2,2-bis (4
-Isopropoxycarbonylphenyl) propane, 2,2
-Bis (4-butoxycarbonylphenyl) propane,
2,2-bis (4-isobutoxycarbonylphenyl) propane, 2,2-bis (4-methoxycarbonylphenyl) -1,1,1,3,3,3-hexafluoropropane, 2,2-bis ( 4-ethoxycarbonylphenyl) -1,1,1,3,3,3
Hexafluoropropane, 2,2-bis (4-propoxycarbonylphenyl) -1,1,1,1,3,3,3-hexafluoropropane, 2,2-bis (4-isopropoxycarbonylphenyl) -1, 1,1,3,3,3-hexafluoropropane, 2,2-bis (4-butoxycarbonylphenyl)-
1,1,1,3,3,3-hexafluoropropane, 2,2-bis (4
-Isobutoxycarbonylphenyl) -1,1,1,3,3,3-
Hexafluoropropane, dimethyl 1,4-naphthalenedicarboxylate, diethyl 1,4-naphthalenedicarboxylate,
Dipropyl 1,4-naphthalenedicarboxylate, diisopropyl 1,4-naphthalenedicarboxylate, dibutyl 1,4-naphthalenedicarboxylate, diisobutyl 1,4-naphthalenedicarboxylate, dimethyl 2,3-naphthalenedicarboxylate,
Diethyl 2,3-naphthalenedicarboxylate, dipropyl 2,3-naphthalenedicarboxylate, diisopropyl 2,3-naphthalenedicarboxylate, dibutyl 2,3-naphthalenedicarboxylate, diisobutyl 2,3-naphthalenedicarboxylate,
Dimethyl 2,6-naphthalenedicarboxylate, diethyl 2,6-naphthalenedicarboxylate, dipropyl 2,6-naphthalenedicarboxylate, diisopropyl 2,6-naphthalenedicarboxylate, dibutyl 2,6-naphthalenedicarboxylate, 2,6-
Aromatic dicarboxylic acid dialkylates such as diisobutyl naphthalenedicarboxylate and / or diphenyl phthalate, di (fluorophenyl) phthalate, di (chlorophenyl) phthalate, di (bromophenyl) phthalate
, Di (methylphenyl) phthalate, di (ethylphenyl) phthalate, di (propylphenyl) phthalate
, Di (isopropylphenyl) phthalate, di (butylphenyl) phthalate, di (isobutylphenyl) phthalate, di (t-butylphenyl) phthalate, di (methoxyphenyl) phthalate, phthalate Acid di (ethoxyphenyl) s, di (nitrophenyl) phthalate, di (phenylphenyl) phthalate, diphenyl isophthalate, di (fluorophenyl) isophthalate, di (chlorophenyl) isophthalate, di (isophthalate) (Bromophenyl) s, di (methylphenyl) isophthalates,
Di (ethylphenyl) isophthalate, di (propylphenyl) isophthalate, di (isopropylphenyl) isophthalate, di (butylphenyl) isophthalate
, Di (isobutylphenyl) isophthalate, di (t-butylphenyl) isophthalate, di (methoxyphenyl) isophthalate, di (ethoxyphenyl) isophthalate, di (nitrophenyl) isophthalate, isophthalate Acid di (phenylphenyl) s, diphenyl terephthalate, di (fluorophenyl) terephthalate, di (chlorophenyl) terephthalate, di (bromophenyl) terephthalate, di (methylphenyl) terephthalate, diterephthalate (Ethylphenyl) s, di (propylphenyl) terephthalate, di (isopropylphenyl) terephthalate, di (butylphenyl) terephthalate, di (isobutylphenyl) terephthalate,
Di (tert-butylphenyl) terephthalate, di (methoxyphenyl) terephthalate, di (ethoxyphenyl) terephthalate, di (nitrophenyl) terephthalate
, Di (phenylphenyl) terephthalates, 4,4'-
Diphenyl biphenyl dicarboxylate, di (fluorophenyl) 4,4'-biphenyl dicarboxylate, di (chlorophenyl) 4,4'-biphenyl dicarboxylate, 4,4 '
-Biphenyldicarboxylic acid di (bromophenyl) s, 4,
4'-biphenyldicarboxylic acid di (methylphenyl)
, 4,4'-biphenyldicarboxylic acid di (ethylphenyl) s, 4,4'-biphenyldicarboxylic acid di (propylphenyl) s, 4,4'-biphenyldicarboxylic acid di (isopropylphenyl) s, 4,4 '-Biphenyldicarboxylic acid di (butylphenyl) s, 4,4'-biphenyldicarboxylic acid di (isobutylphenyl) s, 4,4'-biphenyldicarboxylic acid di (t-butylphenyl) s, 4,4'
-Biphenyldicarboxylic acid di (methoxyphenyl) s,
4,4'-biphenyldicarboxylic acid di (ethoxyphenyl) s, 4,4'-biphenyldicarboxylic acid di (nitrophenyl) s, 4,4'-biphenyldicarboxylic acid di (phenylphenyl) s, 4,4'- Diphenyl diphenyl ether dicarboxylate, 4,4'-diphenyl ether dicarboxylic acid di (fluorophenyl), 4,4'-diphenyl ether dicarboxylic acid di (chlorophenyl), 4,4 '
-Diphenyl ether dicarboxylic acid di (bromophenyl) s, 4,4'-diphenyl ether dicarboxylic acid di (methylphenyl) s, 4,4'-diphenyl ether dicarboxylic acid di (ethylphenyl) s, 4,4'-diphenyl ether dicarboxylic acid di (Propylphenyl) compounds, 4,
4'-diphenyl ether dicarboxylic acid di (isopropylphenyl) s, 4,4'-diphenyl ether dicarboxylic acid di (butylphenyl) s, 4,4'-diphenyl ether dicarboxylic acid di (isobutylphenyl) s, 4,4 '
-Diphenyl ether dicarboxylic acid di (t-butylphenyl), 4,4'-diphenyl ether dicarboxylic acid di (methoxyphenyl), 4,4'-diphenyl ether dicarboxylic acid di (ethoxyphenyl), 4,4'-diphenyl ether dicarboxylic acid Acid di (nitrophenyl) s,
4,4'-diphenyl ether dicarboxylic acid di (phenylphenyl) s, 4,4'-diphenyl sulfide dicarboxylic acid diphenyl, 4,4'-diphenyl sulfide dicarboxylic acid di (fluorophenyl) s, 4,4'-diphenyl sulfide dicarboxylic Acid di (chlorophenyl) s, 4,
4'-diphenyl sulfide dicarboxylic acid di (bromophenyl) s, 4,4'-diphenyl sulfide dicarboxylic acid di (methyl phenyl) s, 4,4'-diphenyl sulfide dicarboxylic acid di (ethyl phenyl) s, 4,4 ' -Diphenyl sulfide dicarboxylic acid di (propylphenyl) s, 4,4'-diphenyl sulfide dicarboxylic acid di (isopropylphenyl) s, 4,4'-diphenyl sulfide dicarboxylic acid di (butylphenyl) s, 4,4'-
Diphenyl sulfide dicarboxylic acid di (isobutylphenyl) s, 4,4'-diphenyl sulfide dicarboxylic acid di (t-butylphenyl) s, 4,4'-diphenyl sulfide dicarboxylic acid di (methoxyphenyl) s, 4,4 '
-Diphenyl sulfide dicarboxylic acid di (ethoxyphenyl), 4,4'-diphenyl sulfide dicarboxylic acid di (nitrophenyl), 4,4'-diphenyl sulfide dicarboxylic acid di (phenylphenyl), 4,4'-benzophenone Diphenyl dicarboxylate, 4,4'-benzophenone dicarboxylic acid di (fluorophenyl),
4'-benzophenone dicarboxylic acid di (chlorophenyl), 4,4'-benzophenone dicarboxylic acid di (bromophenyl), 4,4'-benzophenone dicarboxylic acid di (methylphenyl), 4,4'-benzophenone dicarboxylic acid Di (ethylphenyl) s, 4,4'-benzophenonedicarboxylic acid di (propylphenyl) s, 4,4'-
Benzophenone dicarboxylic acid di (isopropylphenyl) s, 4,4'-benzophenone dicarboxylic acid di (butylphenyl) s, 4,4'-benzophenone dicarboxylic acid di (isobutylphenyl) s, 4,4'-benzophenone dicarboxylic acid di ( t-butylphenyl), 4,4'-benzophenonedicarboxylic acid di (methoxyphenyl),
4,4'-benzophenone dicarboxylic acid di (ethoxyphenyl), 4,4'-benzophenone dicarboxylic acid di (nitrophenyl), 4,4'-benzophenone dicarboxylic acid di (phenylphenyl), 4,4'- Diphenylsulfondicarboxylic acid diphenyl, 4,4'-diphenylsulfondicarboxylic acid di (fluorophenyl) s, 4,4'-
Diphenyl sulfone dicarboxylic acid di (chlorophenyl)
, 4,4'-diphenylsulfondicarboxylic acid di (bromophenyl) s, 4,4'-diphenylsulfondicarboxylic acid di (methylphenyl) s, 4,4'-diphenylsulfondicarboxylic acid di (ethylphenyl) s, 4,4'-diphenylsulfonedicarboxylic acid di (propylphenyl)
Di (isopropylphenyl) 4,4'-diphenylsulfonedicarboxylate, di (butylphenyl) 4,4'-diphenylsulfonedicarboxylate, di (isobutylphenyl) 4,4'-diphenylsulfonedicarboxylate,
4,4'-diphenylsulfondicarboxylic acid di (t-butylphenyl), 4,4'-diphenylsulfondicarboxylic acid di (methoxyphenyl), 4,4'-diphenylsulfondicarboxylic acid di (ethoxyphenyl), 4,4 '
-Di (nitrophenyl) diphenyl sulfone dicarboxylate, di (phenylphenyl) 4,4'-diphenyl sulfone dicarboxylate, diphenyl 4,4'-diphenylmethane dicarboxylate, di (fluorophenyl) 4,4'-diphenylmethane dicarboxylate ), 4,4'-diphenylmethanedicarboxylic acid di (chlorophenyl) s, 4,4 '
-Diphenylmethanedicarboxylic acid di (bromophenyl)
, 4,4'-diphenylmethanedicarboxylic acid di (methylphenyl), 4,4'-diphenylmethanedicarboxylic acid di (ethylphenyl), 4,4'-diphenylmethanedicarboxylic acid di (propylphenyl), 4,4 '-Diphenylmethanedicarboxylic acid di (isopropylphenyl)
4,4'-diphenylmethanedicarboxylic acid di (butylphenyl) s, 4,4'-diphenylmethanedicarboxylic acid di (isobutylphenyl) s, 4,4'-diphenylmethanedicarboxylic acid di (t-butylphenyl) s, 4 , 4'-
Diphenylmethane dicarboxylic acid di (methoxyphenyl)
, 4,4'-diphenylmethanedicarboxylic acid di (ethoxyphenyl), 4,4'-diphenylmethanedicarboxylic acid di (nitrophenyl), 4,4'-diphenylmethanedicarboxylic acid di (phenylphenyl), 2,2 -Bis (4-phenoxycarbonylphenyl) propane, 2,2
-Bis {4- (fluorophenoxycarbonyl) phenyl} propanes, 2,2-bis {4- (chlorophenoxycarbonyl) phenyl} propanes, 2,2-bis {4-
(Bromophenoxycarbonyl) phenyl} propanes, 2,2-bis {4- (methylphenoxycarbonyl)
Phenyl} propanes, 2,2-bis {4- (ethylphenoxycarbonyl) phenyl} propanes, 2,2-bis {4- (propylphenoxycarbonyl) phenyl} propanes, 2,2-bis {4- ( Isopropylphenoxycarbonyl) phenyl} propanes, 2,2-bis {4-
(Butylphenoxycarbonyl) phenyl} propanes, 2,2-bis {4- (isobutylphenoxycarbonyl) phenyl} propanes, 2,2-bis {4- (t-butylphenoxycarbonyl) phenyl} propanes, 2,
2-bis {4- (methoxyphenoxycarbonyl) phenyl} propanes, 2,2-bis {4- (ethoxyphenoxycarbonyl) phenyl} propanes, 2,2-bis {4- (nitrophenoxycarbonyl) phenyl} propane , 2,2-bis {4- (phenylphenoxycarbonyl) phenyl} propane, 2,2-bis (4-phenoxycarbonylphenyl) -1,1,1,3,3,3-hexafluoropropane, 2 , 2-bis {4- (fluorophenoxycarbonyl) phenyl} -1,1,1,1,3,3,3-hexafluoropropane, 2,2-bis {4- (chlorophenoxycarbonyl) phenyl} -1, 1,1,3,3,3-hexafluoropropanes, 2,2-bis {4- (bromophenoxycarbonyl) phenyl} -1,1,1,3,3,3-hexafluoropropanes, 2-bis {4- (methylphenoxycarbonyl Phenyl {-1,1,1,3,3,3-hexafluoropropane, 2,2-bis {4- (ethylphenoxycarbonyl) phenyl} -1,1,1,3,3,3-hexafluoro Propanes, 2,2-bis {4- (propylphenoxycarbonyl) phenyl} -1,1,1,3,3,3-hexafluoropropanes, 2,2-bis {4- (isopropylphenoxycarbonyl) phenyl {-1,1,1,3,3,3-hexafluoropropanes, 2,2-bis {4- (butylphenoxycarbonyl) phenyl} -1,1,1,3,3,3-hexafluoropropane , 2,2-bis {4- (isobutylphenoxycarbonyl) phenyl} -1,1,1,3,3,3-hexafluoropropane, 2,2-bis {4- (t-butylphenoxycarbonyl) Phenyl} -1,1,1,3,3,3-hexafluoropropane, 2,2-bis {4- (methoxyphenoxycarbonyl) phenyl {-1,1,1,3,3,3-hexafluoropropanes, 2,2-bis {4- (ethoxyphenoxycarbonyl) phenyl} -1,1,1,3,3,3-hexafluoropropane , 2,2-bis {4- (nitrophenoxycarbonyl) phenyl} -1,1,1,3,3,3-hexafluoropropane, 2,2-bis {4- (phenylphenoxycarbonyl) phenyl} -1,1,1,3,3,3-hexafluoropropanes, diphenyl 1,4-naphthalenedicarboxylate,
1,4-Naphthalenedicarboxylic acid di (fluorophenyl)
, 1,4-naphthalenedicarboxylic acid di (chlorophenyl) s, 1,4-naphthalenedicarboxylic acid di (bromophenyl) s, 1,4-naphthalenedicarboxylic acid di (methylphenyl) s, 1,4-naphthalenedicarboxylic acid Di (ethylphenyl) s, 1,4-naphthalenedicarboxylic acid di (propylphenyl) s, 1,4-naphthalenedicarboxylic acid di (isopropylphenyl) s, 1,4-naphthalenedicarboxylic acid di (butylphenyl) s, 1 1,4-naphthalenedicarboxylic acid di (isobutylphenyl) s, 1,4-naphthalenedicarboxylic acid di (t-butylphenyl) s, 1,4-naphthalenedicarboxylic acid di (methoxyphenyl) s, 1,4
-Naphthalenedicarboxylic acid di (ethoxyphenyl) s,
1,4-Naphthalenedicarboxylic acid di (nitrophenyl)
, Di (phenylphenyl) 1,4-naphthalenedicarboxylates, diphenyl 2,3-naphthalenedicarboxylate, 2,3
-Naphthalenedicarboxylic acid di (fluorophenyl) s,
2,3-Naphthalenedicarboxylic acid di (chlorophenyl)
, 2,3-naphthalenedicarboxylic acid di (bromophenyl) s, 2,3-naphthalenedicarboxylic acid di (methylphenyl) s, 2,3-naphthalenedicarboxylic acid di (ethylphenyl) s, 2,3-naphthalenedicarboxylic Acid di (propylphenyl) s, 2,3-naphthalenedicarboxylic acid di (isopropylphenyl) s, 2,3-naphthalenedicarboxylic acid di (butylphenyl) s, 2,3-naphthalenedicarboxylic acid di (isobutylphenyl) s, 2,3-naphthalenedicarboxylic acid di (t-butylphenyl) s, 2,3-naphthalenedicarboxylic acid di (methoxyphenyl) s, 2,3-naphthalenedicarboxylic acid di (ethoxyphenyl) s, 2,3
-Di (nitrophenyl) naphthalenedicarboxylic acids, 2,
3-Naphthalenedicarboxylic acid di (phenylphenyl)
, Diphenyl 2,6-naphthalenedicarboxylate, di (fluorophenyl) 2,6-naphthalenedicarboxylate, 2,6
-Di (chlorophenyl) naphthalenedicarboxylic acids, 2,
6-naphthalenedicarboxylic acid di (bromophenyl) s,
2,6-Naphthalenedicarboxylic acid di (methylphenyl)
, Di (ethylphenyl) 2,6-naphthalenedicarboxylic acid, di (propylphenyl) 2,6-naphthalenedicarboxylic acid, di (isopropylphenyl) 2,6-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid Acid di (butylphenyl) s, 2,6-naphthalenedicarboxylic acid di (isobutylphenyl) s, 2,6-naphthalenedicarboxylic acid di (t-butylphenyl) s, 2,6-naphthalenedicarboxylic acid di (methoxyphenyl) , 2,6-naphthalenedicarboxylic acid di (ethoxyphenyl) s, 2,6-naphthalenedicarboxylic acid di (nitrophenyl) s, 2,6-
Aromatic dicarboxylic acid diallylates such as naphthalenedicarboxylic acid di (phenylphenyl) s are used. These aromatic dicarboxylic esters may be used alone or
Used as a mixture of more than one species.

The above diamine component and aromatic dicarboxylic acid or derivative thereof are polymerized in a solvent. As the solvent used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, N, N-diethylacetamide, N, N-dimethylmethoxyacetamide, N-methyl-2-pyrrolidone, 1,3- Dimethyl-2-imidazolidinone, N-methylcaprolactam, dimethylsulfoxide, dimethylsulfone, sulfolane, tetramethylurea, hexamethylphosphoramide, pyridine, α-picoline, β-picoline, γ-picoline, 2,4-lutidine , 2,6-lutidine,
Quinoline, isoquinoline, triethylamine, tripropylamine, tributylamine, tripentylamine,
N, N-dimethylaniline, N, N-diethylaniline, dichloromethane, chloroform, carbon tetrachloride, 1,1,1-trichloroethane, 1,1,2-trichloroethane, trichloroethylene, 1,1,2,2-tetrachloroethane , Tetrachloroethylene, n-hexane, cyclohexane, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, acetonitrile, propionitrile, acetone, methyl ethyl ketone, methyl butyl ketone, methyl isobutyl ketone,
Cyclohexanone, acetophenone, isopropyl ether, tetrahydrofuran, tetrahydropyran, 1,3
-Dioxane, 1,4-dioxane, anisole, phenetole, benzyl ether, phenyl ether, 1,2-
Dimethoxyethane, bis (2-methoxyethyl) ether, 1,2-bis (2-methoxyethoxy) ethane, benzene, toluene, o-xylene, m-xylene, p-xylene, diphenyl, terphenyl, benzyl chloride, nitrobenzene , 2-nitrotoluene, 3-nitrotoluene, 4-nitrotoluene, chlorobenzene, 2-chlorotoluene, 3-chlorotoluene, 4-chlorotoluene,
o-dichlorobenzene, p-dichlorobenzene, bromobenzene, phenol, o-cresol, m-cresol, p-cresol, 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2,6-xylenol , 3,4
-Xylenol, 3,5-xylenol, o-chlorophenol, p-chlorophenol, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, t-butanol, cyclohexanol,
Benzyl alcohol, water and the like can be mentioned. These solvents may be used alone or in combination of two or more, depending on the type of the reaction raw material monomer and the polymerization technique.

When an aromatic dicarboxylic acid dihalide is used as a reaction raw material monomer, a dehydrohalogenating agent is usually used in combination. As the dehydrohalogenating agent used, trimethylamine, triethylamine, tripropylamine,
Tributylamine, tripentylamine, N, N-dimethylbenzylamine, N, N-diethylbenzylamine, N, N
-Dimethylcyclohexylamine, N, N-diethylcyclohexylamine, N, N-dimethylaniline, N, N-diethylaniline, N-methylpyrrolidine, N-ethylpyrrolidine, N-methylpiperidine, N-ethylpiperidine, N-methyl Morpholine, N-ethylmorpholine, pyridine, α-picoline, β-picoline, γ-picoline,
2,4-lutidine, 2,6-lutidine, quinoline, isoquinoline, sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, calcium carbonate, sodium hydrogen carbonate, hydrogen hydrogen carbonate Examples include potassium, calcium oxide, lithium oxide, sodium acetate, potassium acetate, ethylene oxide, propylene oxide and the like.

When an aromatic dicarboxylic acid is used as a reaction raw material monomer, a condensing agent is usually used. Examples of the condensing agent used include sulfuric anhydride, thionyl chloride, sulfite, picryl chloride, phosphorus pentoxide, phosphorus oxychloride, phosphite-pyridine condensing agent, triphenylphosphine-hexachloroethane condensing agent, and propyl phosphorus. Acid anhydride-N-methyl-2-pyrrolidone-based condensing agent;

The reaction temperature varies depending on the polymerization technique and the type of solvent,
It is usually below 300 ° C.

 The reaction pressure is not particularly limited, and the reaction can be carried out at normal pressure.

The reaction time varies depending on the type of the reaction raw material monomer, the polymerization method, the type of the solvent, the type of the dehydrohalogenating agent, the type of the condensing agent and the reaction temperature, but usually, the aromatic polyamide represented by the formula (I) The reaction is allowed to react for a time sufficient to complete the formation. Usually, 10 minutes to 24 hours is sufficient.

By such a reaction, the compound of the formula (I) (Wherein X is a condensed polycyclic aromatic group or Or one or more groups selected from the group consisting of Wherein Y is a direct bond, -O-, -S-, -SO
_{2 -, - CO -, -} CH 2 -, R represents an alkyl group, an alkoxy group, or a halogen group having 1 to 4 carbon atoms, a phenyl group, a represents 0, 1 or 2, and b represents 0 or an integer of 1 to 4. Also, n is 1 to
Represents an integer of 1000. An aromatic polyamide having a repeating unit represented by the formula (1) is obtained.

That is, the aromatic polyamide of the present invention can be obtained by any method such as a known low-temperature solution polycondensation method and a direct polycondensation method as a method for synthesizing a polyamide.

In addition, the aromatic polyamide of the present invention uses 4,4′-bis (3-aminophenoxy) -3,
It is characterized by using 3 ', 5,5'-tetramethylbiphenyl and an aromatic dicarboxylic acid derivative such as aromatic dicarboxylic acid or dicarboxylic acid dihalide.

However, in order to improve the thermal stability and moldability of the aromatic polyamide, even if the end of the polymer molecule is capped with a monovalent carboxylic acid or a carboxylic acid derivative or a monovalent amine, it does not matter at all. Absent.

Such an aromatic polyamide is represented by the following formula (II):
4′-bis (3-aminophenoxy) -3,3 ′, 5,5′-tetramethylbiphenyl as a main component, an aromatic diamine and an aromatic dicarboxylic acid or an aromatic dicarboxylic acid derivative are converted to a monovalent carboxylic acid. Alternatively, it can be obtained by reacting in the presence of a carboxylic acid derivative or a monovalent amine.

That is, a part of the aromatic dicarboxylic acid or the aromatic dicarboxylic acid derivative is a monocarboxylic acid derivative such as an aromatic and / or aliphatic and / or alicyclic monocarboxylic acid or a monocarboxylic acid halide; It is produced by replacing a part with an aromatic and / or alicyclic monoamine.

The monovalent carboxylic acids used in these methods include benzoic acid, chlorobenzoic acids, bromobenzoic acids,
Methylbenzoic acid, ethylbenzoic acid, methoxybenzoic acid, ethoxybenzoic acid, nitrobenzoic acid, acetylbenzoic acid, acetoxybenzoic acid, hydroxybenzoic acid, biphenylcarboxylic acid, benzophenonecarboxylic acid, diphenylethercarboxylic acid, diphenylsulfidecarboxylic acid, diphenyl Sulfone carboxylic acids, 2,2-diphenylpropane carboxylic acids, 2,2-
Diphenyl-1,1,1,3,3,3-hexafluoropropanecarboxylic acids, naphthalenecarboxylic acids, acetic acid, chloroacetic acid, dichloroacetic acid, trichloroacetic acid, fluoroacetic acid, difluoroacetic acid, trifluoroacetic acid, nitroacetic acid, propionic acid , Butyric acid, valeric acid, caproic acid, cinnamic acid, cyclohexanecarboxylic acid and the like. These monocarboxylic acids are used alone or in combination of two or more.

Examples of the monocarboxylic acid halide include benzoyl chloride, benzoyl bromide, chlorobenzoyl chlorides, chlorobenzoyl bromide, bromobenzoyl chloride, bromobenzoyl bromide, methylbenzoyl chloride, methylbenzoyl bromide, ethylbenzoyl chloride, Ethyl benzoyl bromide, methoxy benzoyl chloride, methoxy benzoyl bromide, ethoxy benzoyl chloride, ethoxy benzoyl bromide, nitro benzoyl chloride, nitro benzoyl bromide, acetyl benzoyl chloride, acetyl benzoyl bromide, acetoxy benzoyl chloride, Acetoxybenzoyl bromides, hydroxybenzoyl chlorides, hydroxybenzoyl bromides, Phenyl carboxylic acid chlorides, biphenyl carboxylic acid bromides, benzophenone carboxylic acid chlorides, benzophenone carboxylic acid bromide, diphenyl ether carboxylic acid chlorides, diphenyl ether carboxylic acid bromide, diphenyl sulfide carboxylic acid chlorides, diphenyl sulfide carboxylic acid bromide, Diphenylsulfonecarboxylic acid chlorides, diphenylsulfonecarboxylic acid bromides, 2,2-diphenylpropanecarboxylic acid chlorides,
2,2-diphenylpropanecarboxylic acid bromides, 2,2-
Diphenyl-1,1,1,3,3,3-hexafluoropropanecarboxylic acid chlorides, 2,2-diphenyl-1,1,1,3,3,3-
Hexafluoropropanecarboxylic acid bromides, naphthalenecarboxylic acid chlorides, naphthalenecarboxylic acid bromides, acetyl chloride, acetyl bromide, chloroacetic chloride, chloroacetic bromide, dichloroacetic chloride, dichloroacetic bromide, trichloroacetic chloride, trichloroacetic bromide, Fluoroacetic acid chloride,
Fluoroacetate bromide, difluoroacetic chloride, difluoroacetic bromide, trifluoroacetic chloride, trifluoroacetic bromide, nitroacetic chloride, nitroacetic bromide, propionacetic chloride, propionacetic bromide, butyric chloride, butyric bromide, valeric chloride, valeric acid Bromide, caproic acid chloride, caproic acid bromide, cinnamic acid chloride, cinnamic acid bromide, cyclohexanecarboxylic acid chloride, cyclohexanecarboxylic acid bromide and the like. These monocarboxylic acid halides may be used alone or in combination of two or more.

Also, as the monocarboxylic acid esters, benzoic acid
Methyl, ethyl benzoate, propyl benzoate, benzoic acid
Isopropyl, butyl benzoate, isobutyl benzoate,
Phenyl benzoate, fluorophenyl benzoates, benzo
Chlorophenyl balates, bromophenyl benzoates, ammonium
Methylphenyl benzoates, ethylphenyl benzoates,
Propyl benzoate, isopropyl benzoate
Phenyls, butylphenyl benzoates, isobu benzoate
Tylphenyls, t-butylphenyl benzoates, benzoate
Methoxyphenyl balates, ethoxyphenyl benzoate
, Nitrophenyl benzoates, phenyl benzoate
Nil, methyl chlorobenzoate, ethyl chlorobenzoate
, Propyl chlorobenzoate, isochlorochlorobenzoate
Propyl, butyl chlorobenzoate, chlorobenzoic acid
Isobutyls, phenyl chlorobenzoates, chlorobenzo
Fluorophenyl balates, chlorophenyl chlorobenzoate
And bromophenyl chlorobenzoates, chlorobenzo
Methylphenyls, ethylphenyl chlorobenzoate
, Propylphenyl chlorobenzoates, chlorobenzoate
Isopropyl phenyls, butyl chlorobenzoate
Nyls, isobutylphenyl chlorobenzoates, chloro
T-butylphenyl benzoates, methoxy benzoate
Cyphenyls, ethoxyphenyl chlorobenzoates,
Nitrophenyl lolobenzoate, phenylbenzoic chlorobenzoate
Ruphenyls, methyl bromobenzoates, bromobenzoate
Ethyl acid, propyl bromobenzoate, bromobenzoate
Isopropylates, butyl bromobenzoates, bromoammonium
Isobutyl benzoates, Phenyl bromobenzoates, Bro
Mo-fluorobenzoates, chloro bromobenzoate
Phenyls, bromophenyl bromobenzoates, bromo
Methylphenyl benzoates, ethyl bromobenzoate
Nyls, propylphenyl bromobenzoates, bromoammonium
Isopropylphenyl benzoates, butyl bromobenzoate
Phenyls, isobutylphenyl bromobenzoates,
T-butylphenyl lomobenzoate, bromobenzoic acid
Toxiphenyls, ethoxyphenyl bromobenzoate
, Nitrophenyl bromobenzoates, bromobenzoic acid
Phenyl phenyls, methyl benzoates, methyl
Ethyl benzoate, methyl propyl benzoate, methyl
Isopropyl benzoate, butyl methyl benzoate,
Isobutyl butyl benzoate, phenyl methyl benzoate
, Fluorophenyl methyl benzoate, methyl benzoate
Acid chlorophenyls, bromophenyl methylbenzoate
, Methyl benzoate methyl phenyls, methyl benzoate
Ethylphenyls, propylphenyl methylbenzoate
, Isopropylphenyl methyl benzoate, methyl ammonium
Butylphenyl benzoates, isobutyl methyl benzoate
Phenyls, t-butylphenyl methylbenzoate, methyl
Methoxyphenyl benzoates, methyl benzoate
Cyphenyls, nitrophenyl methylbenzoates, methyl
Phenylphenyl benzoates, methyl ethyl benzoate
, Ethyl ethyl benzoate, propyl ethyl benzoate
, Ethyl isopropyl benzoate, ethyl benzoate
Tyls, isobutyl ethyl benzoate, ethyl benzoic acid
Phenyls, fluorophenyl ethylbenzoates, ethi
Chlorophenyl benzoates, Bromoethyl benzoate
Phenyls, methylphenyl ethylbenzoate, ethyl ammonium
Ethyl phenyl benzoate, propyl ethyl benzoate
Nil, isopropylphenyl ethyl benzoate, ethi
Butyl phenyl benzoates, isobutyl ethyl benzoate
Ruphenyls, t-butylphenyl ethylbenzoate,
Methoxyphenyl ethyl benzoate, ethyl benzoate
Toxiphenyls, nitrophenyl ethylbenzoates,
Phenyl phenyl ethyl benzoate, methoxy benzoic acid
Methyls, ethyl methoxybenzoates, methoxybenzoates
Propyls, isopropyl methoxybenzoates, meth
Butyl xybenzoates, isobutyl methoxybenzoate
, Phenyl methoxybenzoates, methoxybenzoic acid
Fluorophenyls, chlorophenyl methoxybenzoate
, Bromophenyl methoxybenzoates, methoxybenzoate
Methylphenyl balates, ethyl phenyl methoxybenzoate
, Methoxyphenyl benzoate, methoxy
Isopropyl phenyl benzoate, methoxy benzoate
Tylphenyls, isobutylphenyl methoxybenzoate
, Methoxybenzoic acid t-butylphenyls, methoxy
Methoxyphenyl benzoates, ethoxy methoxybenzoate
Cyphenyls, nitrophenyl methoxybenzoates,
Phenyl phenyl benzoate, ethoxy benzoate
Methyls, ethyl ethoxybenzoates, ethoxybenzoate
Propylates, isopropyl ethoxybenzoates, ethoxy
Butyl oxybenzoates, isobutyl ethoxy benzoate
, Phenyl benzoate, ethoxybenzoate
Fluorophenyls, chlorophenyl ethoxybenzoate
, Bromophenyl ethoxybenzoates, ethoxy benzoate
Methylphenyl balates, ethylphenythoxybenzoate
, Ethoxypropyl benzoates, ethoxy
Isopropylphenyl benzoates, ethoxy benzoate
Tylphenyls, isobutylphenyl ethoxybenzoate
, Ethoxybenzoic acid t-butylphenyls, ethoxy
Methoxyphenyl benzoates, ethoxybenzoic acid ethoxy
Cyphenyls, nitrophenyl ethoxybenzoates,
Phenyl phenyl benzoates, nitrobenzoic acid
Chills, ethyl nitrobenzoates, nitrobenzoic acid pro
Pills, isopropyl nitrobenzoate, nitrobenzoate
Butyls, isobutyl nitrobenzoates, nitrobenzo
Phenyl perfuates, fluorophenyl nitrobenzoates,
Chlorophenyl nitrobenzoates, nitrobenzoic acid bro
Mophenyls, methylphenyl nitrobenzoates, nitro
Ethylphenyl benzoate, propyl nitrobenzoate
Phenyls, isopropylphenyl nitrobenzoates,
Butylphenyl nitrobenzoates, iso-nitrobenzoate
Butylphenyls, t-butylphenyl nitrobenzoate
, Methoxyphenyl nitrobenzoates, nitrobenzoate
Ethoxyphenyls, nitrophenyl nitrobenzoate
, Phenylphenyl nitrobenzoates, acetylbenzo
Methyl perfate, ethyl acetylbenzoate, acetyl ammonium
Propyl benzoate, isopropyl acetyl benzoate,
Butyl acetyl benzoate, isobutyl acetyl benzoate
, Phenyl acetylbenzoate, acetylbenzoic acid
Fluorophenyls, chlorophenyl acetylbenzoate
, Bromophenyl acetylbenzoates, acetylbenzo
Methyl phenyl fragrances, ethyl phenyl benzoate
, Acetylphenyl benzoate, acetyl
Isopropylphenyl benzoates, acetyl benzoate
Tylphenyls, isobutylphenyl acetylbenzoate
, Acetyl t-butylphenyl benzoates, acetyl
Methoxyphenyl benzoates, ethoxy acetyl benzoate
Cyphenyls, nitrophenyl acetylbenzoates,
Phenylphenyl cetylbenzoate, acetoxybenzoate
Methyls, acetoxybenzoates, acetoxy
Propyl benzoate, isopropyl acetoxybenzoate
, Acetoxybenzoic acid butyls, acetoxybenzoic acid
t-butyls, isobutyl acetoxybenzoates, ace
Phenyl toxoxybenzoate, Fluoro acetoxybenzoate
Rophenyls, chlorophenyl acetoxybenzoates,
Bromophenyl acetoxybenzoates, acetoxybenzo
Methylphenyl fragrances, ethyl acetate acetoxybenzoate
Nil, propylphenyl acetoxybenzoate, ace
Isopropyl phenyl oxybenzoate, ammonium acetoxy
Butylphenyl benzoates, isobutyrate acetoxybenzoate
Ruphenyls, t-butylphenyl acetoxybenzoate
, Methoxyphenyl acetoxybenzoates, acetoxy
Ethoxyphenyl benzoates, acetoxybenzoic acid
Trophenyls, phenylphenyl acetoxybenzoate
, Methyl hydroxybenzoates, hydroxybenzoic acid
Ethyls, propyl hydroxybenzoates, hydroxy
Isopropyl benzoate, butyl hydroxybenzoate
, Isobutyl hydroxybenzoates, hydroxybenzo
Phenyl benzoates, fluorophenyl hydroxybenzoate
, Chlorophenyl hydroxybenzoates, hydroxy
Bromophenyl benzoates, methyl hydroxybenzoate
Phenyls, ethylphenyl hydroxybenzoates, arsenic
Propylphenyl droxybenzoates, hydroxybenzo
Isopropylphenyl fragrance, Buty hydroxybenzoate
Ruphenyls, isobutylphenyl hydroxybenzoate
, T-butylphenyl hydroxybenzoates, hydro
Methoxyphenyl xylbenzoates, hydroxybenzoic acid
Ethoxyphenyls, nitrophenyl hydroxybenzoate
Phenylphenylhydroxybenzoates, bife
Methyl nylcarboxylates, ethyl biphenylcarboxylate
, Biphenylcarboxylates, biphenylcar
Isopropyl borate, butyl biphenylcarboxylate
, Biphenylcarboxylate isobutyls, biphenylca
Phenyl rubonates, fluorophenyl biphenylcarboxylate
Phenyls, chlorophenyl biphenylcarboxylates,
Bromophenyl phenylcarboxylate, biphenylcar
Methylphenyl bonates, ethyl biphenylcarboxylate
Phenyls, propylphenyl biphenylcarboxylate
, Isopropylphenyl biphenylcarboxylate,
Butylphenyl phenylcarboxylate, biphenylcar
Isobutylphenyl borate, biphenylcarboxylic acid t
-Butylphenyls, methoxyphenyl biphenylcarboxylate
Phenyls, ethoxyphenyl biphenylcarboxylates,
Biphenylcarboxylic acid nitrophenyls, biphenylca
Phenylphenyl rubonates, benzophenone carboxylic
Acid, ethyl benzophenonecarboxylate, ben
Propyl zophenone carboxylate, benzophenone cal
Isopropyl bonates, benzophenone carboxylate
Benzophenone carboxylate, benzo
Phenyl phenone carboxylate, benzophenone carbo
Fluorophenyls, benzophenonecarboxylic acid
Lolophenyls, bromophenone carboxylate bromofe
Nyls, methylphenyl benzophenonecarboxylates,
Benzophenone carboxylate ethylphenyls, benzoph
Propenyl phenone carboxylate, benzophenone
Isopropylphenyl carboxylate, benzophenone
Butylphenyl rubonates, benzophenone carboxylic acid
Isobutylphenyls, benzophenonecarboxylic acid t-
Butylphenyls, methoxy benzophenonecarboxylate
Phenyls, benzophenone carboxylic acid ethoxyphenyl
Benzophenone carboxylate
Phenylphenyl benzophenone carboxylate, diphenyi
Methyl ether carboxylate, diphenyl ether
Ethyl rubonates, diphenyl ether carboxylic acid pro
Pills, isopropyl diphenyl ether carboxylate
, Dibutyl ether carboxylates, diphenyl
Isobutyl carboxylate, diphenyl ether
Phenyl carboxylate, diphenyl ether carboxylic
Acid fluorophenyls, diphenyl ether carboxylic acid
Chlorophenyls, diphenyl ether carboxylic acid bro
Mophenyls, methyl diphenyl ether carboxylate
Phenyls, ethyl phenyl diphenyl ether carboxylate
And propylphenyl diphenyl ether carboxylate
, Diphenyl ether carboxylate isopropyl phenyl
Butylphenyl diphenyl ether carboxylate
, Isobutylphenyl diphenyl ether carboxylate
, T-butylphenyl diphenyl ether carboxylate
, Methoxyphenyl diphenyl ether carboxylate
And ethoxyphenyl diphenyl ether carboxylate
, Nitrophenyl diphenyl ether carboxylate,
Phenylphenyl diphenyl ether carboxylate, di
Methyl phenyl sulfide carboxylate, diphenyls
Ethyl sulfide carboxylate, diphenyl sulfide
Propyl rubonates, diphenyl sulfide carboxylic acid
Isopropyls, diphenyl sulfide carboxylate
, Isobutyl diphenylsulfidecarboxylates,
Phenyl diphenyl sulfide carboxylate, diphenyl
Fluorophenylfluorosulfides, diphenyl
Chlorophenyl sulfide carboxylate, diphenyl
Bromophenyl sulfides, diphenyls
Methylphenyl sulfide carboxylate, diphenyl sulf
Ethyl phenyl carboxylate, diphenyl sulf
Propyl phenyl carboxylate, diphenyl sulf
Isopropyl phenyl carboxylate, diphenyls
Butyl phenyl carboxylate, diphenyl sulf
Isobutyl phenyl carboxylate, diphenyls
T-butylphenyl sulfide carboxylate, diphenyl
Sulfocarboxylic acid methoxyphenyls, diphenyl
Ethoxyphenyl sulfides, diphenyl
Nitrophenyl sulfide carboxylate, diphenyls
Phenyl phenyl carboxylate, diphenyls
Methyl sulfonate, diphenyl sulfone carb
Ethyl acid, propyl diphenylsulfonate
, Diisopropyl sulfonate carboxylate, di
Butyl phenylsulfonate, diphenylsulfur
Isobutyl carboxylate, diphenyl sulfone carb
Phenyl bonates, diphenyl sulfone carboxylic acid full
Orophenyls, chlorodiphenylsulfonate
Phenyls, bromofe diphenylsulfonate
Nyls, methylphenyl diphenylsulfonate
, Ethylphenyl diphenylsulfonate,
Propylphenyl diphenylsulfonate
Isopropylphenyl phenylsulfonate,
Butylphenyl diphenylsulfonate
Isobutylphenylsulfonyl carboxylate, diph
T-butylphenyl phenylsulfonate, diph
Methoxyphenylsulfenylcarboxylates, diphe
Ethoxyphenylsulfonyl carboxylate, diphenyl
Nitrophenylsulfoncarboxylates, diphenyls
Phenylphenylsulfonate, 2,2-diphenyl
Methyl lupropanecarboxylate, 2,2-diphenylpro
Ethyl pancarboxylates, 2,2-diphenylpropaneca
Propyl rubonates, 2,2-diphenylpropanecarbo
Isopropylates, 2,2-diphenylpropanecarbo
Butyl acid, 2,2-diphenylpropanecarboxylic acid
Sobutyls, 2,2-diphenylpropanecarboxylic acid
Nyls, 2,2-diphenylpropanecarboxylic acid fluoro
Phenyls, 2,2-diphenylpropanecarboxylic acid
Lophenyls, 2,2-diphenylpropanecarboxylic acid
Lomophenyls, 2,2-diphenylpropanecarboxylic acid
Methylphenyls, 2,2-diphenylpropanecarboxylic
Ethylphenyls, 2,2-diphenylpropanecarbo
Propylphenyls, 2,2-diphenylpropaneca
Isopropylphenyl rubonates, 2,2-diphenylp
Butanephenyl lopancarboxylate, 2,2-diphenyl
Isobutylphenyl propanecarboxylate, 2,2-diph
T-butylphenyl phenylpropanecarboxylates, 2,2
-Methoxyphenyl diphenylpropanecarboxylates,
Ethoxyphenyl 2,2-diphenylpropanecarboxylate
, 2,2-diphenylpropanecarboxylic acid nitrophenyl
Phenyls, 2,2-diphenylpropane carboxylate
Phenyls, 2,2-diphenyl-1,1,1,3,3,3-hexafur
Methyl olopropanecarboxylate, 2,2-diphenyl-
1,1,1,3,3,3-hexafluoropropanecarboxylate
And 2,2-diphenyl-1,1,1,3,3,3-hexafluoro
Propanecarboxylic acid propyls, 2,2-diphenyl-1,
1,1,3,3,3-hexafluoropropanecarboxylic acid isop
Ropyl, 2,2-diphenyl-1,1,1,3,3,3-hexafur
Butyl olopropanecarboxylate, 2,2-diphenyl-
1,1,1,3,3,3-hexafluoropropanecarboxylic acid iso
Butyls, 2,2-diphenyl-1,1,1,3,3,3-hexafur
Oropropane carboxylic acid phenyls, 2,2-diphenyl
1,1,1,3,3,3-hexafluoropropanecarboxylic acid
Fluorophenyls, 2,2-diphenyl-1,1,1,3,3,3-he
Xafluoropropanecarboxylic acid chlorophenyls, 2,
2-diphenyl-1,1,1,3,3,3-hexafluoropropane
Bromophenyl carboxylate, 2,2-diphenyl-1,1,
1,3,3,3-Methylhexafluoropropanecarboxylate
Phenyls, 2,2-diphenyl-1,1,1,3,3,3-hexafur
Ethylphenyl olopropanecarboxylate, 2,2-diph
Enyl-1,1,1,3,3,3-hexafluoropropanecarbo
Propylphenyls, 2,2-diphenyl-1,1,1,3,
Isopropyl 3,3-hexafluoropropanecarboxylate
Phenyls, 2,2-diphenyl-1,1,1,3,3,3-hexaph
Butylphenyl fluoropropanecarboxylates, 2,2-di
Phenyl-1,1,1,3,3,3-hexafluoropropane
Isobutylphenyl bonates, 2,2-diphenyl-1,1,
1,3,3,3-hexafluoropropanecarboxylic acid t-butyl
Ruphenyls, 2,2-diphenyl-1,1,1,3,3,3-hexa
Methoxyphenyl fluoropropanecarboxylates, 2,2
-Diphenyl-1,1,1,3,3,3-hexafluoropropane
Ethoxyphenyl carboxylates, 2,2-diphenyl-1,
Nitro 1,1,3,3,3-hexafluoropropanecarboxylate
Phenyls, 2,2-diphenyl-1,1,1,3,3,3-hexaph
Phenylphenyl fluoropropanecarboxylate, naphtha
Methyl lencarboxylate, ethyl naphthalenecarboxylate
, Naphthalenecarboxylates, naphthalenecar
Isopropyl bonates, butyl naphthalenecarboxylate
, Naphthalenecarboxylate isobutyls, naphthaleneca
Phenyl rubonates, fluorophthalene carboxylate
Phenyls, chlorophenyl naphthalenecarboxylates,
Bromophenyl phthalene carboxylate, naphthalene carb
Methylphenyl bonates, ethyl naphthalenecarboxylate
Phenyls, propylphenyl naphthalenecarboxylate
, Isopropylphenyl naphthalenecarboxylate, naphthalene
Butylphenylphthalenecarboxylate, naphthalenecar
Isobutylphenyl borate, naphthalene carboxylic acid t
-Butylphenyls, methoxyphenyl naphthalenecarboxylate
Phenyls, ethoxyphenyl naphthalenecarboxylates,
Nitrophenyl naphthalene carboxylate, naphthaleneca
Phenylphenyl rubonates, methyl acetate, ethyl acetate
, Propyl acetate, isopropyl acetate, butyl acetate, vinegar
Isobutyl acid, phenyl acetate, fluorophenyl acetate
, Chlorophenyl acetate, bromophenyl acetate, vinegar
Methylphenyls, ethylacetates, acetic acid pro
Pyrphenyls, isopropylphenyl acetates, butyl acetate
Tylphenyls, isobutylphenyl acetates, t-acetic acid
Butylphenyls, methoxyphenyl acetates, acetic acetate
Xyphenyls, nitrophenyl acetates, phenyl acetate
Phenyls, methyl chloroacetate, ethyl chloroacetate,
Propyl loroacetate, isopropyl chloroacetate, chlorovinegar
Butyl acetate, isobutyl chloroacetate, phenylacetate chloroacetate
, Fluorophenyl chloroacetate, chloroacetate
Phenyls, bromophenyl chloroacetates, chloroacetic acid
Methylphenyls, ethylphenylchloroacetates,
Propyl phenylacetate, isopropyl chloroacetate
Phenyls, butylphenyl chloroacetates,
Sobutylphenyls, t-butylphenyl chloroacetate
, Methoxyphenyl chloroacetates, ethoxy chloroacetate
Cyphenyls, nitrophenyl chloroacetates, chlorovinegar
Acid phenylphenyls, methyl dichloroacetate, dichloro
Ethyl acetate, propyl dichloroacetate, isochlorodichloroacetate
Propyl, butyl dichloroacetate, isobutyl acetate
Phenyl, dichloroacetate, fluorodichloroacetate
Nil, chlorophenyl dichloroacetate, dichloroacetic acid
Bromophenyls, methylphenyl dichloroacetates, di
Ethylphenyl chloroacetate, propyl dichloroacetate
Phenyls, isopropylphenyl dichloroacetate, dic
Butylphenylloroacetates, isobutyl dichloroacetate
Phenyls, t-butylphenyl dichloroacetate, dichloro
Methoxyphenyl loacetates, ethoxyfe dichloroacetate
Nil, nitrophenyl dichloroacetate, dichloroacetic acid
Phenylphenyls, methyl trichloroacetate, trichloro
Ethyl loacetate, propyl trichloroacetate, trichlorovinegar
Isopropyl acid, butyl trichloroacetate, trichloro vinegar
Isobutyl acid, phenyl trichloroacetate, trichlorovinegar
Acid fluorophenyls, chlorophenyl trichloroacetate
, Bromophenyl trichloroacetate, trichloroacetic acid
Methylphenyls, ethylphenyl trichloroacetate,
Propyl trichloroacetate, trichloroacetic acid i
Sopropylphenyls, butylphenyl trichloroacetate
, Isobutylphenyl trichloroacetate, trichloro
T-butylphenyl acetates, methoxyphenyl trichloroacetate
Phenyls, ethoxyphenyl trichloroacetates, tric
Nitrophenyl loroacetate, Phenylphenyl trichloroacetate
Phenyls, methyl fluoroacetate, ethyl fluoroacetate,
Propyl fluoroacetate, isopropyl fluoroacetate,
Butyl fluoroacetate, isobutyl fluoroacetate, fluoro
Phenyl acetate, fluorophenyl fluoroacetates, full
Chlorophenyl oroacetate, bromophenyfluoroacetate
Toluene, methylphenyl fluoroacetate, fluoroacetic acid
Tylphenyls, propylphenyl fluoroacetates,
Isopropylphenyl fluoroacetate, Butyfluoroacetate
Phenyls, isobutylphenyl fluoroacetates,
T-butylphenyl fluoroacetate, methoxy trifluoroacetate
Cyphenyls, ethoxyphenyl fluoroacetates, full
Nitrophenyl oroacetate, Phenylfluoroacetate
Nyls, methyl difluoroacetate, ethyl difluoroacetate
Propyl difluoroacetate, isopropyl difluoroacetate
Pill, butyl difluoroacetate, isobutyl difluoroacetate
Phenyl, difluoroacetate, fluorodifluoroacetate
Phenyls, chlorophenyl difluoroacetates, difur
Bromophenyl oroacetate, methyl trifluoroacetate
Nil, ethylphenyl difluoroacetate, difluoro
Propyl acetates, isopropyl difluoroacetate
Phenyls, butylphenyl difluoroacetates, difur
Isobutylphenyl oloacetates, t-butyl difluoroacetate
Tylphenyls, methoxyphenyl difluoroacetates,
Ethoxyphenyl difluoroacetate, difluoroacetic acid
Trophenyls, phenylphenyl difluoroacetates,
Methyl trifluoroacetate, ethyl trifluoroacetate,
Propyl trifluoroacetate, isopropyl trifluoroacetate
Butyl acetate, isobutyl trifluoroacetate
Chill, phenyl trifluoroacetate, trifluoroacetate
Fluorophenyls, chlorophenyl trifluoroacetate
, Bromophenyl trifluoroacetates, trifluoroacetate
Methylphenyl acetates, ethyl phenylacetate trifluoroacetate
, Propylphenyl trifluoroacetates, trifluoro
Isopropylphenyl oroacetates, trifluoroacetate
Tylphenyls, isobutylphenyl trifluoroacetate
, Tert-butylphenyl trifluoroacetate, trifluoro
Methoxyphenyl oroacetate, ethoxy trifluoroacetate
Cyphenyls, nitrophenyl trifluoroacetates,
Phenylphenyl trifluoroacetates, methyl nitroacetate
, Ethyl nitroacetate, propyl nitroacetate, nitro vinegar
Isopropyl acid, butyl nitroacetate, isobu nitroacetate
Phenyl, phenyl nitroacetate, fluorophenyl nitroacetate
Compounds, chlorophenyl nitroacetate, bromonitroacetate
Phenyls, methylphenyl nitroacetate, nitroacetic acid
Ethylphenyls, propylphenyl nitroacetates,
Isopropylphenyl troacetates, butyl acetate
Phenyls, isobutylphenyl nitroacetate, nitro vinegar
T-butylphenyl acid, methoxyphenyl nitroacetate
, Ethoxyphenyl nitroacetates, nitro nitroacetate
Phenyls, phenylphenyl nitroacetates, propio
Methyl propionate, ethyl propionate, propionate
Isopropyl propionate, butyl propionate,
Isobutyl propionate, phenyl propionate, pro
Fluorophenyl pionates, chlorophen propionate
Nyls, bromophenyl propionates, propionic acid
Methylphenyls, ethylphenyl propionates,
Propyl ropionate, isopropropionate
Pyrphenyls, butylphenyl propionates, pro
Isobutylphenyl pionates, t-butyl propionate
Ruphenyls, methoxyphenyl propionates, pro
Ethoxyphenyl pionates, Nitrophen propionate
Nyls, phenylphenyl propionates, methyl butyrate
, Ethyl butyrate, propyl butyrate, isopropyl butyrate, butyrate
Butylate, isobutyl butyrate, phenylbutyrate, fluorbutyrate
Rophenyls, chlorophenyl butyrate, bromofe butyrate
Nyls, methylphenyl butyrate, ethylphenyl butyrate
, Propylphenyl butyrate, isopropylphenyl butyrate
Butylphenyl butyrate, isobutylphenyl butyrate
, Tert-butylphenyl butyrate, methoxyphenyl butyrate
, Ethoxyphenyl butyrate, nitrophenyl butyrate,
Phenylphenyl butyrate, methyl valerate, ethyl valerate
Propyl valerate, isopropyl valerate, butyrate butyl
, Isobutyl valerate, phenyl valerate, fluor valerate
Lophenyls, chlorophenyl valerate, bromovalerate
Phenyls, methylphenyl valerate, ethyl valerate
Phenyls, propylphenyl valerates, isoprovalerate
Pyrphenyls, butylphenyl valerates, isovalerate
Butylphenyls, t-butylphenyl valerate, valerian
Methoxyphenyls, ethoxyphenyl valerates,
Nitrophenyl valerate, phenylphenyl valerate, mosquito
Methyl pronoate, ethyl caproate, propyl caproate
Isopropyl caproate, butyl caproate, cap
Isobutyl lonate, phenyl caproate, phenyl caproate
Fluorophenyls, chlorophenyl caproate, cap
Bromophenyl lonates, methylphenyl caproate
, Ethyl phenyl caproate, propyl caproate
Phenyls, isopropylphenyl caproate, cap
Butyl phenyl lonates, isobutyl phenyl caproate
Compounds, t-butylphenyl caproate,
Toxiphenyls, ethoxyphenyl caproate,
Nitrophenyl pronoates, phenylphenocaproate
Oleic acid, methyl cinnamate, ethyl cinnamate, propyl cinnamate,
Isopropyl cinnamate, butyl cinnamate, isobutyrate cinnamate
Phenyl cinnamate, fluorophenyl cinnamate, cinnamon
Chlorophenyl acid, bromophenyl cinnamate, cinnamic acid
Methylphenyls, ethylphenylcinnamate, cinnamic acid
Propyl phenyls, isopropyl cinnamate, katsura
Butylphenyl cinnamate, isobutylphenyl cinnamate,
T-butylphenyl cinnamate, methoxyphenyl cinnamate
, Ethoxyphenyl cinnamate, nitrophenyl cinnamate
, Phenylphenyl cinnamate, cyclohexanecarbo
Methyl ester, ethyl cyclohexanecarboxylate, cyclo
Propyl hexanecarboxylate, cyclohexanecarboxy
Isopropyl acid, butyl cyclohexanecarboxylate,
Isobutyl chlorohexanecarboxylate, cyclohexaneca
Phenyl rubonate, fluoro cyclohexane carboxylate
Phenyls, chlorophenyl cyclohexanecarboxylate
, Bromophenyl cyclohexanecarboxylates, cyclone
Methylphenyl rohexanecarboxylate, cyclohexa
Ethylphenyl carboxylate, cyclohexanecarbo
Propyl phenylates, cyclohexanecarboxylic acid
Sopropylphenyls, butane cyclohexanecarboxylate
Lphenyls, isobutyl phenylcyclohexanecarboxylate
Phenyls, t-butylphenylcyclohexanecarboxylate
Methoxyphenyl cyclohexanecarboxylates,
Ethoxyphenyl cyclohexanecarboxylates, cyclo
Hexane carboxylate nitrophenyls, cyclohexane
And phenylphenyl carboxylate. these
Monocarboxylic acid esters may be used alone or as a mixture of two or more.
Used as

The amount of the monocarboxylic acids used is 0.001 to 1.0 mole per mole of aromatic diamine. If the amount is less than 0.001 mol, the viscosity increases during high-temperature molding, which causes a reduction in moldability. On the other hand, if it exceeds 1.0 mol, the mechanical properties deteriorate. A preferred amount is 0.01 to 0.5 mol.

When a monovalent amine is used, for example, aniline, o-toluidine, m-toluidine, p-toluidine, 2,3-xylidine, 2,4-xylidine, 2,5-xylidine, 2,6- Xylidine, 3,4-xylidine, 3,5-xylidine, o-chloroaniline, m-chloroaniline, p
-Chloroaniline, o-bromoaniline, m-bromoaniline, p-bromoaniline, o-nitroaniline, m
-Nitroaniline, p-nitroaniline, o-anisidine, m-anisidine, p-anisidine, o-phenetidine, m-phenetidine, p-phenetidine, o-aminophenol, m-aminophenol, p-aminophenol, o- Aminobenzaldehyde, m-aminobenzaldehyde, p-aminobenzaldehyde, o-aminobenzonitrile, m-aminobenzonitrile, p-aminobenzonitrile, 2-aminobiphenyl, 3-aminobiphenyl, 4-aminobiphenyl, 2-aminophenyl Phenyl ether, 3-aminophenyl phenyl ether, 4-aminophenyl phenyl ether, 2-aminobenzophenone, 3-aminobenzophenone, 4-aminobenzophenone, 2-aminophenylphenyl sulfide, 3-amino Phenyl sulfide, 4
Aminophenylphenyl sulfide, 2-aminophenylphenylsulfone, 3-aminophenylphenylsulfone, 4-aminophenylphenylsulfone, α-naphthylamine, β-naphthylamine, 1-amino-2-naphthol, 2-amino-1-naphthol, 4-amino-
1-naphthol, 5-amino-1-naphthol, 5-amino-2-naphthol, 7-amino-2-naphthol,
8-amino-1-naphthol, 8-amino-2-naphthol, 1-aminoanthracene, 2-aminoanthracene, 9-aminoanthracene, methylamine, dimethylamine, ethylamine, diethylamine, propylamine, dipropylamine, isopropylamine , Diisopropylamine, butylamine, dibutylamine, isobutylamine, diisobutylamine, pentylamine, dipentylamine, benzylamine, cyclopropylamine, cyclobutylamine, cyclopentylamine, cyclohexylamine and the like. These monoamines are used alone or in combination of two or more.

The amount of monoamine used is from 0.001 to 1.0 mole per mole of aromatic dicarboxylic acids. If the amount is less than 0.001 mol, the viscosity increases during high-temperature molding, which causes a reduction in moldability. On the other hand, if it exceeds 1.0 mol, the mechanical properties deteriorate. A preferred amount is 0.01 to 0.5 mol.

The aromatic polyamide and its resin composition of the present invention can be subjected to melt molding. In this case, other thermoplastic resins can be blended in an appropriate amount according to the purpose within a range that does not impair the purpose of the present invention. As thermoplastic resins that can be blended, polyethylene, polypropylene, polycarbonate, polyarylate, polyamide, polyimide, polysulfone, polyethersulfone, polyetherketone, polyetheretherketone, polyphenylenesulfide, polyamideimide, polyetherimide, modified And polyphenylene oxide. It is also possible to mix a thermosetting resin or a filler to such an extent that the object of the invention is not impaired.
Examples of the thermosetting resin include a phenol resin and an epoxy resin. Fillers include abrasion-resistant materials such as graphite, carborundum, silica powder, molybdenum disulfide, and fluororesin, glass fibers, carbon fibers, boron fibers, silicon carbide fibers, carbon whiskers, asbestos, metal fibers, and ceramic fibers. Reinforcement materials such as antimony trioxide, magnesium carbonate, calcium carbonate, etc., electrical property improving materials such as clay and mica, asbestos, silica, graphite and other tracking resistance improving materials, barium sulfate, silica, Acid resistance improving materials such as calcium metasilicate, thermal conductivity improving materials such as iron powder, zinc powder, aluminum powder, and copper powder, other glass beads, talc,
Diatomaceous earth, alumina, shirasubarun, hydrated alumina, metal oxides, coloring agents and the like.

Various materials are used as the fibrous reinforcing material used in the present invention, for example, glass fiber, carbon fiber, potassium titanate fiber, aromatic polyamide fiber, silicon carbide fiber,
Alumina fiber, boron fiber, ceramic fiber and the like can be mentioned, and glass fiber, carbon fiber, potassium titanate fiber and aromatic polyamide fiber are particularly preferably used.

The glass fibers used in the present invention are those obtained by quenching molten glass while stretching it by various methods to form a thin fiber having a predetermined diameter.Strands in which single fibers are bundled with a sizing agent, uniform strands Roving, etc., which are arranged in a bundle. For the glass fiber, a silane coupling agent such as aminosilane and epoxysilane, chromic chloride, and other surface treatment agents suitable for the purpose can be used in order to have an affinity with the base resin of the present invention. The length of the glass fiber in the present invention greatly affects the physical properties of the obtained molded article and the workability during the production of the molded article. In general, as the glass fiber length increases, the physical properties of the molded article improve, but conversely, the workability during the production of the molded article deteriorates. For this reason, the length of the glass fiber in the present invention is 0.1 to 6 mm, preferably 0.
Those having a size in the range of 3 to 4 mm are preferable because the physical properties and workability of the molded product are balanced.

The carbon fiber used in the present invention is a high elasticity and high strength fiber obtained by carbonizing polyacrylonitrile, petroleum pitch or the like as a main raw material. In the present invention, both polyacrylonitrile and petroleum pitch can be used. Carbon fibers having an appropriate diameter and an appropriate aspect ratio (length / diameter ratio) are used depending on the reinforcing effect and the mixing property. The diameter of the carbon fiber is usually 5 to 20 μm, particularly 8 to 15 μm.
m is preferable. The aspect ratio is 1-60
0, and particularly preferably about 100 to 350, depending on the reinforcing effect and the mixing property. If the aspect ratio is small, there is no reinforcing effect, and if the aspect ratio is large, the mixing property is poor, and a good molded product cannot be obtained. In addition, those obtained by treating the surface of the carbon fiber with various treatment agents, for example, an epoxy resin, a polyamide resin, a polycarbonate resin, a polyacetal resin, and the like, and those using a known surface treatment agent depending on the purpose are also used.

The potassium titanate fiber used in the present invention is a kind of high-strength fiber (whisker) and has a chemical composition of K ₂
A _{O · 6TiO 2, K 2 O} · 6TiO 2 · 1 / 2H 2 O needle-like crystals having a basic, representative melting point is 1,300-1,350 ° C.. Average fiber length is 5
~ 50μm, average fiber diameter of 0.05 ~ 1.0μm is applied, average fiber length is 20 ~ 30μm, average fiber diameter is 0.1 ~
0.3 μm is preferred. The potassium titanate fiber can be used without any usual treatment, but in order to have an affinity with the base resin of the present invention, a silane coupling agent such as aminosilane or epoxysilane, chromic chloride, or other surface treatment depending on the purpose. Agents can be used.

The aromatic polyamide fibers used in the present invention are relatively newly developed heat-resistant organic fibers, and are expected to be developed in various fields by utilizing many unique characteristics. For example, typical examples include those having the following structural formulas, and at least one of them or 2
Mixtures of more than one species are used.

In addition, there are aromatic polyamide fibers having various skeletons due to ortho-, meta-, and para-positional structural isomers. Among them, those having a para-para-position bond of (1) having a high softening point and a high melting point in the present invention as heat-resistant organic fibers. Most preferred.

In the case of 5 parts by weight or less of the glass fiber and the carbon fiber, the reinforcing effect peculiar to the glass fiber or the carbon fiber characteristic of the present invention cannot be obtained. Conversely, if it is used in an amount of 100 parts by weight or more, the fluidity during molding of the composition becomes poor, and it becomes difficult to obtain a satisfactory molded product. If the content of the potassium titanate fiber is 5 parts by weight or less, the improvement in mechanical properties at high temperatures, which is a feature of the present invention, is insufficient. Conversely, if the amount is too large, dispersion in melt mixing becomes insufficient, and further, the fluidity becomes low, and molding under ordinary conditions becomes difficult, which is not preferable. The preferred amount is 10 to 100 parts by weight. When the amount of the aromatic polyamide fiber is 5 parts by weight or less, a composition excellent in moldability and mechanical strength, which is a feature of the present invention, cannot be obtained. If it is used in an amount of 100 parts by weight or more, the fluidity of the composition at the time of molding deteriorates, and it becomes difficult to obtain a satisfactory molded product. The preferred amount is 10 to 50 parts by weight.

The resin composition using the polyamide of the present invention can be produced by a generally known method, but the following method is particularly preferable.

(1) The polyamide powder and the fibrous reinforcing material are preliminarily mixed using a mortar, Henschel mixer, drum blender, tumbler blender, ball mill, ribbon blender, and the like, and then kneaded with a generally known melting and mixing base, a hot roll, or the like. Pellet or powder.

(2) Polyamide powder is dissolved or suspended in an organic solvent in advance, a fibrous reinforcing material is immersed in the solution or suspension, and then the solvent is removed in a hot air oven, and then pelletized or powdered. To In this case, as a solvent, for example, N, N-dimethylformamide, N, N-dimethylacetamide, N, N-diethylacetamide, N, N-dimethylmethoxyacetamide, N-methyl-2-pyrrolidone, 1,
3-dimethyl-2-imidazolidinone, N-methylcaprolactam, 1,2-dimethoxyethane, bis (2-methoxyethyl) ether, 1,2-bis (2-methoxyethoxy) ethane, bis [2- (2 -Methoxyethoxy) ethyl] ether, tetrahydrofuran, 1,3-dioxane, 1,4-dioxane, pyridine, picoline, dimethylsulfoxide, dimethylsulfone, tetramethylurea,
Hexamethylphosphoramide and the like are used. These organic solvents may be used alone or in combination of two or more.

The polyamide resin composition of the present invention is molded by a known molding method such as an injection molding method, an extrusion molding method, a compression molding method, a rotational molding method, and put into practical use.

〔Example〕

Hereinafter, the production examples of the aromatic polyamide of the present invention and the physical properties and performance of the obtained aromatic polyamide will be described in detail with reference to Examples and Comparative Examples.

 In the examples, various physical properties were measured by the following methods.

Logarithmic viscosity: Measured at 35 ° C. after dissolving 0.50 g of polyamide powder in 100 ml of concentrated sulfuric acid.

Glass transition temperature (Tg): DSC (Shimadzu DT-40 series, DSC-4
1M).

5% weight loss temperature: Measured by DTA-TG (Shimadzu DT-40 series, DTA-40M) in air.

Melt viscosity: Measured with a load of 100 kg using Shimadzu Koka Flow Tester CFT500A.

Reference Example 1A In a vessel equipped with a stirrer and a nitrogen inlet tube, under a nitrogen atmosphere, 4,4′-bis (3-aminophenoxy) -3,3 ′,
After charging and dissolving 29.72 g (0.070 mol) of 5,5'-tetramethylbiphenyl and 350 g of N-methyl-2-pyrrolidone, 17.0 g (0.168 mol) of triethylamine was added.
Cooled to ° C. Thereafter, the stirring was increased and 14.21 g (0.70 mol) of terephthalic acid chloride was charged, and stirring was continued at room temperature for 3 hours. The viscous polymer solution thus obtained was discharged into vigorously stirred methanol to precipitate a white powder. The white powder was filtered off, washed with methanol,
Drying under reduced pressure at 12 ° C. for 12 hours gave 38.04 g (98.0% yield) of polyamide powder.

The logarithmic viscosity of this polyamide powder was 0.91 dl / g, the glass transition temperature was 287.7 ° C., and the 5% weight loss temperature was 504.4 ° C.

The results of elemental analysis of the obtained polyamide powder are as follows. CH N O calculated value (%) 77.96 5.45 5.05 11.54 Observed value (%) 78.11 5.33 4.96 11.60 Further , FIG. 1 shows an infrared absorption spectrum of the obtained polyamide powder. This spectrum diagram, in the vicinity of 1660 cm ^-1 and near 1530 cm ^-1 which is the characteristic absorption band of amide, significant absorption was observed.

Further, the obtained polyamide powder was dissolved in N-methyl-2-pyrrolidone, and then cast on a glass plate.
C. for 1 hour and 250.degree. C. for 2 hours to obtain a colorless and transparent polyamide film. The tensile strength of this polyamide film was 1100 kg / cm ² , and the tensile elongation was 21%. Both measurement methods are based on ASTM D-822.

The water absorption of this film was 0.68%. The measurement method is based on ASTM D-750-63.

Reference Example 2A 37.93 g (yield 97.7%) of a polyamide powder having an logarithmic viscosity of 1.01 dl / g was obtained in the same manner as in Reference Example 1A, except that terephthalic acid chloride in Reference Example 1A was replaced with isophthalic acid chloride.

The glass transition temperature of this polyamide powder is 270.5 ° C, 5
The% weight loss temperature was 502.7 ° C. The results of elemental analysis of the obtained polyamide powder are as follows. CH N O calculated value (%) 77.96 5.45 5.05 11.54 Observed value (%) 78.15 5.44 4.90 11.51 FIG. 2 shows an infrared absorption spectrum of the obtained polyamide powder. This spectrum diagram, in the vicinity of 1660 cm ^-1 and near 1520 cm ^-1 which is the characteristic absorption band of amide, significant absorption was observed.

Further, using the obtained polyamide powder, a colorless and transparent polyamide film was obtained in the same manner as in Reference Example 1A. The tensile strength of this polyamide film was 1210 kg / cm ² , the tensile elongation was 23%, and the water absorption was 0.70%.

Reference Example 3A 14.21 g (0.07 g) of terephthalic acid chloride in Reference Example 1A
0 mol) was replaced with 7.11 g (0.035 mol) of terephthalic acid chloride and 7.11 g (0.035 mol) of isophthalic acid chloride, and 37.85 g (yield) of a polyamide powder having an logarithmic viscosity of 0.98 dl / g 97.5%).

The glass transition temperature of this polyamide powder is 276.9 ° C, 5
The% weight loss temperature was 500.8 ° C.

A colorless and transparent polyamide film was obtained in the same manner as in Reference Example 1A using the obtained polyamide powder. The tensile strength of this polyamide film is 1120 kg / cm ² , and the tensile elongation is
The water absorption was 21% and the water absorption was 0.70%.

Reference Example 4A In a vessel equipped with a stirrer and a nitrogen inlet tube, under a nitrogen atmosphere, 8.31 g (0.05 mol) of terephthalic acid, lithium chloride 1
0.0 g, 30.0 g of calcium chloride, 100 g of pyridine, 31.0 g (0.10 mol) of triphenyl phosphite, and 400 g of N-methyl-2-pyrrolidone were charged and dissolved, and then heated to 120 ° C. There, 4,4'-bis (3-aminophenoxy)-
21,3 g (0.05 mol) of 3,3 ', 5,5'-tetramethylbiphenyl was charged and stirred at 120 ° C for 2 hours. The viscous polymer solution thus obtained was discharged into vigorously stirred methanol to precipitate a white powder. This white powder was separated by filtration, washed with methanol, and dried under reduced pressure at 180 ° C. for 12 hours to obtain 27.18 g (yield 98.0%) of a polyamide powder.

The logarithmic viscosity of this polyamide powder was 1.09 dl / g, the glass transition temperature was 288.5 ° C, and the 5% weight loss temperature was 502.2 ° C.

The results of elemental analysis of the obtained polyamide powder are as follows. C H N O Calculated (%) 77.96 5.45 5.05 11.54 Found (%) 78.15 5.31 5.00 11.54 Further, the infrared absorption spectrum of the obtained polyamide powder (Figure 3) is a polyamide powder obtained in Reference Example 1A It was exactly the same. This spectrum diagram, in the vicinity of 1660 cm ^-1 and near 1530 cm ^-1 which is the characteristic absorption band of amide, significant absorption was observed.

Reference Example 5A Under a nitrogen atmosphere, a container equipped with a stirrer and a nitrogen inlet tube was charged with 19.42 g (0.10 mol) of dimethyl terephthalate,
42.46 g (0.10 mol) of 4'-bis (3-aminophenoxy) -3,3 ', 5,5'-tetramethylbiphenyl and 1000 g of diphenyl ether were charged and stirred at 250 ° C for 8 hours. The reaction thus obtained was poured into vigorously stirred methanol to give a white powder. This white powder was separated by filtration, washed with methanol, and dried under reduced pressure at 180 ° C. for 12 hours.
g (94.0% yield) of polyamide powder was obtained.

The logarithmic viscosity of this polyamide powder was 0.70 dl / g, the glass transition temperature was 283.0 ° C., and the 5% weight loss temperature was 500.1 ° C.

The results of elemental analysis of the obtained polyamide powder are as follows. C H N O Calculated (%) 77.96 5.45 5.05 11.54 Found (%) 76.81 5.50 5.11 12.58 Further, the infrared absorption spectrum of the obtained polyamide powder (Figure 4) is a polyamide powder obtained in Reference Example 1A It was exactly the same. This spectrum diagram, in the vicinity of 1660 cm ^-1 and near 1530 cm ^-1 which is the characteristic absorption band of amide, significant absorption was observed.

Example 6 A container equipped with a stirrer and a nitrogen inlet tube was charged with 4,4'-bis (3-aminophenoxy) -3,3 ', 5,
8.49 g (0.020 mol) of 5'-tetramethylbiphenyl and N
After 99.8 g of methyl-2-pyrrolidone was charged and dissolved, 4.86 g (0.048 mol) of triethylamine was added, and 5
Cooled to ° C. Thereafter, stirring was strengthened and 3.78 g (0.019 mol) of terephthalic acid chloride was charged, and stirring was continued at room temperature for 2 hours. Thereafter, 0.422 g (0.0030 mol) of benzoyl chloride was charged, and stirring was continued at room temperature for 2 hours. The resulting polymer solution was discharged into vigorously stirred methanol to precipitate a white powder. After filtering off this white powder,
Washed with methanol, dried under reduced pressure at 180 ° C for 12 hours, 10.
88 g (yield 98.1%) of polyamide powder was obtained.

The logarithmic viscosity of this polyamide powder was 0.55 dl / g.
When the melt viscosity of the obtained polyamide powder was measured,
It was 10,000 poise at 360 ° C. Further, the obtained strand was pale yellow, transparent, highly flexible, and very tough.

Further, the thermal stability of the polyamide obtained in this example was measured by changing the residence time in the cylinder of the flow tester. The measurement was performed at 360 ° C. The results are shown in FIG.
Even if the residence time in the cylinder becomes longer, the melt viscosity hardly changes, indicating that the thermal stability is good.

The thermal deformation temperature of a molded product obtained by compression molding this polyamide powder at 340 ° C. and 150 kg / cm ² for 15 minutes was 268 ° C. Measurement method is ASTM D-648, load 18.6kg
/ due to the cm ^2.

Example 7 In a container equipped with a stirrer and a nitrogen inlet tube, 4,4'-bis (3-aminophenoxy) -3,3 ', 5,
8.07 g (0.019 mol) of 5'-tetramethylbiphenyl and N
After 99.8 g of methyl-2-pyrrolidone was charged and dissolved, 4.86 g (0.048 mol) of triethylamine was added, and 5
Cooled to ° C. Thereafter, stirring was strengthened, and 4.06 g (0.020 mol) of terephthalic acid chloride was charged, and stirring was continued at room temperature for 2 hours. Thereafter, 0.279 g (0.0030 mol) of aniline was charged, and stirring was continued at room temperature for 2 hours. The resulting polymer solution was discharged into vigorously stirred methanol to precipitate a white powder. This white powder was separated by filtration, washed with methanol, and dried under reduced pressure at 180 ° C. for 12 hours to give 10.58 g (yield 9
7.4%) of a polyamide powder.

The logarithmic viscosity of this polyamide powder was 0.53 dl / g.
When the melt viscosity of the obtained polyamide powder was measured,
It was 9400 poise at 360 ° C. Further, the obtained strand was pale yellow, transparent, highly flexible, and very tough.

Comparative Example 1 Under a nitrogen atmosphere, 2.16 g (0.020 mol) of p-phenylenediamine and N-
After charging and dissolving 56.2 g of methyl-2-pyrrolidone,
4.05 g (0.040 mol) of triethylamine was added and cooled to 5 ° C. After that, increase the stirring and terephthalic acid chloride 3.
80 g (0.0187 mol) were charged all at once, and stirring was continued at room temperature for 2 hours. Thereafter, 0.548 g (0.0039 mol) of benzoyl chloride was charged, and stirring was continued at room temperature for 2 hours. The resulting polymer solution was discharged into vigorously stirred methanol to precipitate a white powder. After filtering off this white powder,
Washed with methanol, dried under vacuum at 180 ° C for 12 hours, 4.4
g (yield 97.7%) of polyamide powder was obtained.

When the glass transition temperature of this polyamide powder was measured, no clear value was shown.

The melt viscosity was measured at 370 ° C. and 400 ° C., but no melt flow occurred at any temperature.

Comparative Example 2 A polyamide powder was synthesized in exactly the same manner as in Example 6, but without using benzoyl chloride.

 The logarithmic viscosity of the polyamide powder was 0.54 dl / g.

The residence time in the flow tester cylinder was changed in the same manner as in Example 6, and the melt viscosity was measured.
As shown in the figure, the melt viscosity increased as the residence time became longer, and the heat stability was inferior to the polyamide obtained in Example 6.

Reference Examples 8A and 9A Polyamides obtained in Reference Examples 1A and 2A, respectively 100
Silane-treated glass fiber with a fiber length of 3 mm and a fiber diameter of 13 μm per part by weight (Nitto Boseki's trademark: CS-3PE-476S)
Was added in the amount shown in Table 1, mixed with a drum blender mixer (manufactured by Kawada Seisakusho), melt-kneaded at a temperature of 360 ° C with a single screw extruder having a diameter of 30 mm, and then the strand was air-cooled and cut. A pellet was obtained.

The obtained pellets were injection molded (Arburg molding machine, maximum clamping force 35 tons, injection pressure 500 kg / cm ² , cylinder temperature 360 ° C, mold temperature 150 ° C) to obtain test pieces for various measurements.
A measurement was made. Measured tensile strength (according to ASTM D-638), flexural strength and flexural modulus (ASTM D-790), Izod impact strength (notched) (ASTM D-256), heat distortion temperature (ASTM D-648), molding Table 1 shows the results of the shrinkage ratio (ASTM D-955).

Reference Examples 3B and 4B Each of the polyamides obtained in Reference Examples 1A and 2 was 100
Table 2 shows the results obtained by using the same glass fibers as those in Reference Examples 8A and 9A in parts by weight outside the scope of the present invention.

Reference Examples 10A and 11A Each of the polyamides obtained in Reference Examples 1A and 2 was 100
Carbon fiber having an average diameter of 12 μm, a length of 3 mm, and an aspect ratio of 250 (trade name of Toray Co., Ltd.) was added to the parts by weight as shown in Table 3, and the same procedure as in Reference Examples 8A and 9A was performed.
The result shown in FIG.

Reference Examples 5B and 6B 100 polyamides obtained in Reference Examples 1A and 2 respectively
To the parts by weight, the same carbon fibers as in Reference Examples 10A and 11A were added in an amount of 120 parts by weight, respectively, and Reference Examples 10A and 11
Extruded strands were attempted in the same manner as in A, but none of them could be extruded.

Reference Examples 12A and 13A Polyamides obtained in Reference Examples 1A and 2A respectively 100
To the parts by weight, potassium titanate fibers having a cross-sectional diameter of 0.2 μm and an average diameter of 20 μm (Otsuka Chemicals Co., Ltd .: Tismo D) were added in the amounts shown in Table 4, and the same procedures as in Reference Examples 8A and 9A were performed. -4 were obtained.

Reference Examples 14A and 15A Polyamides obtained in Reference Examples 1A and 2A respectively 100
To the parts by weight, an aromatic polyamide fiber having an average fiber length of 3 mm (Dupont's trademark: Kevlar) was added in an amount shown in Table 5, and the results shown in Table 5 were obtained in the same manner as in Reference Examples 8A and 9A. Obtained.

[Effects of the Invention] The present invention provides a completely novel aromatic polyamide having excellent processability or heat stability in addition to the excellent heat resistance inherent to the aromatic polyamide. Furthermore, the aromatic polyamide resin composition of the present invention has excellent dimensional stability, excellent mechanical strength and excellent workability. Therefore, electric / electronic parts, automobile parts, precision mechanical parts, Is an extremely useful material used for medical equipment parts, base materials for spacecraft, and the like, and has a very large industrial use effect.

[Brief description of the drawings]

FIG. 1 shows Reference Example 1A according to the present invention, FIG. 2 shows Reference Example 2A,
FIG. 3 shows an example of an infrared absorption spectrum of each polyamide powder obtained in Reference Example 4A, and FIG. 4 shows an example of an infrared absorption spectrum diagram of each polyamide powder obtained in Reference Example 5A. FIG. 5 shows the resin residence time in the cylinder of the flow tester at a measurement temperature of 360 ° C. and a load of 100 kg in order to compare the thermal stability of each of the polyamide powders obtained in Example 6 and Comparative Example 2. It shows the result of measuring the melt viscosity by changing.

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Claims (3)

(57) [Claims] 1. A polyamide obtained by reacting a diamine with a dicarboxylic acid or a dicarboxylic acid derivative,
The following formula (I) (Wherein X is a condensed polycyclic aromatic group or a compound represented by the formula Or one or more groups selected from the group consisting of Wherein Y is a direct bond, -O -, - S -, - SO 2 -,
-CO -, - CH ₂ -, R represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group, or a halogen group, a phenyl group, a represents 0, 1 or 2, and b represents 0.
Or, represents an integer of 1 to 4. N represents an integer of 1 to 1000. ) As a basic skeleton, the polycondensation reaction is carried out in the presence of a monovalent carboxylic acid or a carboxylic acid derivative, and the amount of the aromatic dicarboxylic acid or the aromatic dicarboxylic acid derivative is reduced to the aromatic diamine. Characterized in that it is obtained by reacting at a ratio of 0.7 to 1.0 mol per mol, and a monovalent acid or acid derivative is reacted at a ratio of 0.001 to 1.0 mol with respect to 1 mol of aromatic diamine. Polyamide with good properties. 2. A polyamide obtained by reacting a diamine with a dicarboxylic acid or a dicarboxylic acid derivative.
The following formula (I) (Wherein X is a condensed polycyclic aromatic group or a compound represented by the formula Or one or more groups selected from the group consisting of Wherein Y is a direct bond, -O -, - S -, - SO 2 -,
-CO -, - CH ₂ -, R represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group, or a halogen group, a phenyl group, a represents 0, 1 or 2, and b represents 0.
Or, represents an integer of 1 to 4. N represents an integer of 1 to 1000. ) As a basic skeleton, the polycondensation reaction is carried out in the presence of a monovalent amine, and the amount of aromatic diamine is 0.7 mole per mole of aromatic dicarboxylic acid or aromatic dicarboxylic acid derivative. The thermal stability is obtained by reacting at a ratio of 0.001 to 1.0 mol with respect to 1 mol of the aromatic dicarboxylic acid or the aromatic dicarboxylic acid derivative. Good polyamide. 3. A fiber reinforcing material selected from the group consisting of 100 parts by weight of the polyamide according to claim 1 and / or glass fiber, carbon fiber, potassium titanate fiber and aromatic polyamide fiber. And a polyamide resin composition comprising: