JPS63135424A - Production of copolyamide - Google Patents

Abstract

PURPOSE:To obtain a high-polymerization degree copolyamide suitable for a permselective membrane, by reacting a mixture of a diphenyl sulfone diamine and piperazine with an aromatic dicarboxylic acid halide in the presence of a specified compound. CONSTITUTION:The purpose copolyamide is obtained by polymerizing a diamine component comprising diamines of formulas I and II at a molar ratio of 95/5-35/65 with an aromatic dicarboxylic acid halide of formula III in an organic solvent and piridine and/or an N,N-dialkylaniline. In the formulas, R<1> and R<2> are each H or a 1-12C hydrocarbon group, R<3> and R<4> are each an active hydrogen-free monovalent organic group, n1 and n2 are each 0 or 1-3, R<5>, R<6>, R<7>, R<8>, R<9>, R<10> and R<11> are each H or a 1-12C hydrocarbon group, X is a halogen, and R is a 2-12C organic group. Examples of said acid halides which are particularly desirable include isophthaloyl dichloride and terephthaloyl dichloride.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a method for producing a novel copolyamide, and more particularly to a method for producing a copolyamide suitable for a selectively permeable membrane.

(Prior Art) A solution of one or more existing substances dissolved in a common solvent is pumped through a selectively permeable membrane at a pressure higher than the osmotic pressure of the solution, or by applying a low pressure on the permeate side to the solution. There are dialysis and pervaporation separation methods that selectively permeate and separate the components inside, and reverse osmosis that selectively passes water from an aqueous solution of inorganic salts but does not allow inorganic salts to pass through.

These methods use permselective membranes and reverse osmosis membranes. (Hereinafter, both will be collectively referred to as a selectively permeable membrane.) Such a selectively permeable membrane is generally made of a persistent polymer substance. Its form is a homogeneous film with a dense and homogeneous structure, a composite film made by coating this on a suitable support, or an I film with a thickness of 0.1 to 0.3 microns or less.
Il,! ? ! ! There are membranes with an asymmetric structure consisting of a surface polymer layer and a porous substructure made of the same material and serving as a support for this thin layer. This is commonly called an asymmetric membrane.

This asymmetric membrane has high water permeability and desalination performance.

It relies on the dense thin surface polymer layer mentioned above.

Please note that cellulose acetate has not been used industrially as a material for conventional 2 selectively permeable membranes. However, for this membrane, aromatic polyamide is known as a new separation membrane material to replace cellulose (Japanese Patent Publication No. 53-45540).

This results in hydrolysis! Although the biodegradability and thermal deterioration properties have been improved, it has the drawback of very weak chlorine resistance. That is, there is a problem in that it is very sensitive to chlorine (oxidizing chlorine) used as a water disinfectant, that is, it lacks chlorine resistance.

In addition, metaphenylene diamine from Film 2 Fufu Co., Ltd.
A willow obtained by crosslinking rose phenylene diamine with an aromatic polyacid halide such as trimesic acid clophyte has been proposed (Japanese Patent Application Laid-Open No. 147106/1983). It is disclosed that this membrane not only has extremely good reverse osmosis membrane performance but also has chlorine resistance.

On the other hand, an excellent chlorine-resistant reverse osmosis anisotropic membrane (Japanese Unexamined Patent Application Publication No. 109271/1983) is made of a copolyamide obtained by reacting a bibeodine diamine with an aromatic cyclonic acid.
@Reference) is known.

(Problems to be Solved by the Invention) The reverse osmosis membrane disclosed in the above-mentioned Japanese Patent Application Laid-Open No. 147106/1987 has chlorine resistance, but its chlorine resistance is only short-term and long-term. It is 1'l that it cannot be used for a long time.
J.

Also, the polyamide using the above-mentioned pivefudin.

It is soluble in organic solvents such as N,N-dimethy/l/acetamide and N-methylpyrrolidone, which are commonly used in film formation, and is suitable for protic solvents such as formic acid and metacreso-y, which are dangerous to handle. It just dissolves. Therefore, it is difficult to industrially manufacture selectively permeable membranes using this polyamide.

As a result of extensive research into the deterioration (chlorine resistance) of aromatic polyamides made of various aromatic diamines, we found that the #chlorine properties of aromatic polyamides largely depend on the chemical structure of the aromatic amine component used. Heading nine.

As a result of further intensive research on this point, we discovered that a copolyamide containing pibeodine diamine and diphenylsulfone diamine as amine components has excellent film-forming properties, permselectivity, and chlorine resistance, and we have already applied for a patent.

Since the amine component of the single-leaf copolyamide consists of an aliphatic diamine and an aromatic diamine that have different reactivities, it is difficult to obtain a copolyamide with a high degree of polymerization suitable for producing hollow fiber membranes.

The present inventors have conducted intensive studies on increasing the degree of polymerization of the present copolyamide and have found that the degree of polymerization of the present copolyamide depends on the type of acid scavenger used, leading to the present invention.

(Means for Solving the Problems) This invention provides that the molar ratio of piperazine and/or its derivative to diphenylsulfonic diamine is 5/95 to 65.
/35 is an improved method for producing an aromatic copolyamide obtained by reacting an aromatic cyanobyl acid chloride compound with a mixed diamine component where the molar ratio of diamine compounds (1) and (2) is 9 in ratio
515 to 35/65 and an aromatic dicarboxylic acid halide compound represented by the following general formula (3) in an organic solvent to produce a copolyamide, one reaction is performed. It has been found that when pyridine and/or N,N-cyaniline is used as a scavenger for hydrogen chloride produced in the process, a copolyamide that is easy to purify and has a high viscosity can be obtained.

(R”)nx (R4)R2 (However, R1 and R2 are hydrogen atoms or have 1 to 1 carbon atoms
12 hydrocarbon groups, R3 and R4 are hydrogen atoms, or monovalent organic groups having no active water volume, n].

R2 represents a natural number from 1 to 3. ) (Kudashi*
R6HR') R, R11, R9, RIG, R1
1, R12 is a hydrogen atom.

or a hydrocarbon group having 1 to 12 carbon atoms ('-jo)
IOC-R-COX (3) (wherein, (1) is 3,3'
-diaminodiphenylsulfone and/or c4.4'-
Diaminodiphenyls, diamine compound (2)
is piperazine and /′! Nen is t (trance) -2.5-
When producing a copolyamide in which R is a phenylene group in the aromatic cyanoboxylic acid halide compound (3), which is dimethylpiperazine, pyridine and/or N,N-sialkylaniline added as an acid scavenger are added to the polymer. It has been found that this method is very effective in increasing the viscosity of polymers and making it easier to purify them.

As the compound represented by the general formula (1), 3.3'
-diaminodiphenylsulfone, 3,3'-diamino-4,4'-dimethyldiphenylsulfone, N,N
'-dimethy/L'-313'-diaminodiphenyls
Hong, 4.4'-diaminodiphe=〃S〃phone, 3,
3〆-dimethyl-4,4'-diaminodiphenylsulfone, N,N'-dimethyl-4,4'-diaminodiphenylsulfone.

Examples include 3.3'-dinitro-4,4'-diaminodiphenylsulfone, and particularly preferred compounds are 3.
, 3'-diaminodiphenylsulfone, 4.4'-
Diaminodiphenyμλμhon.

Examples of the compound represented by the general formula (2) include piperazine,
2-ethylpiperazine, t()-2,5-dimethylpiperazine, cis-2,5-dimethylpiperazine,
2,6-dimethylpiperazine, 2,3゜5-trimethylpiperazine, 2,2.3,3,5,5,6.6
-Octamethylpiperazine% 2.2,5.5-tetofumethy-piperazine, 2,2,3,5,5.6-hexamethylpiperazine, 2-ethylpiperazine, 2,5-diethylpiperazine, 2,315-triethyl Piperazine, 2゜2.3,5,5.6-hexaethylpiperazine, 2,3,5.6-tetraethylpibefudine,
2-propypibewodine, 2,6-dipropylpiperazine, 2,3.5-)ripropypibe, radin,
2,3,5.6-tetofu n-propiμpiperazine,
2-butylpiperazine, 2,5-di-n-butybibefudin, 2,5-di-text-butyμpiperazine,
2,3.5-) Lee n-butyμpiperazine, 2-pentylpiperazine, 2-deciμpibefudine, 2,5-divinyμpiperazine.

2.5-sp pheniμpivezine, 2-phenylbivefudin, 2,3,5.6-tetraphenylpivezine.

2-naphthylpiperazine % 2,5-dinaphthylpibefudine, 2-tolylpiperazine, 2,5-ditripiperazine, 2,3,5,6-tetophthrylbibefudine, and the like. Particularly preferred diamine compounds (2) are piperazine and t-2+5-dimethylubiperazine.

As the acid halide compound (3) in the present invention, phthalate/L' acid, isophthalic acid, terephthalic acid, 4.4'-
Diphenyl dicarboxylic acid, 1,2-naphthalene dicarboxylic acid, 1,3-naphthalene dicarboxylic acid, 1,4-
Naphthalene dicarboxylic acid, 1,5-naphthalene dicarboxylic acid, 1,6-naphthalene dicarboxylic acid, 1,7-naphthalene dicarboxylic acid, 1,8-naphthalene dicarboxylic acid, 2.3-naphthalene dicarboxylic acid, 2. Examples include aromatic dicarboxylic acid halide compounds such as 6-naphthalene dicarboxylic acid and 2,7-naphthalene dicarboxylic acid. Among these, isophthalic acid dichloride and terephthalic acid dichloride are particularly preferred.

The above-mentioned aromatic acid hafide compounds can be mixed and used in any proportion.

The copolymerization ratio of the compound represented by general formula (1) and the diamine compound represented by general formula (2) is 9515 to 3 in molar ratio.
It is 5/65.

Diamine compound (2 mol. more than 65 mol.

High viscosity copolyamides are difficult to obtain. The preferred amount of diamine compound (2) is in the range of 10 to 60 mo/I/%.

Particularly preferred is a range of 10 to 40 mo/l/%.

The copolyamide of the present invention can be synthesized by the following solution polymerization method.

Although various organic solvents can be used as the solvent used in the solution polymerization method, amide type K is preferably used.

Preferred solvents include N-methy/l/-2-pyrrolidone, hexamethylphosphoramide)', NIN'-dimethylacetamide-N+N'-s'methyμformamide, and mixtures thereof. 9. Methylene chloride is added to the amide solvent.

Chloroform = L2-dichloroethane, 1,1
．． It is also possible to mix chlorine-based solvents such as 2-trichloroethane, 1,1,2,2-tetofucloethane, and chlorobenzene.

The above-mentioned solvents used in the polymerization must be sufficiently dehydrated in advance by distillation or by a dehydrating agent such as Mohiko Kyu-Shigu. The water content of the solvent used in the polymerization reaction of the present invention is 5
00 ppm or less, preferably 3001) pm or less, particularly preferably 150 ppm or less.

Also, pyridine and/or N as an acid scavenger.

N-sialkylaniline is used. As the N,N-sialkylaniline compound, N,N-dimethylaniline,
N,N-diethylaniline is particularly preferred from the viewpoint of increasing the viscosity of the polymer and facilitating purification.

The water content of the acid scavenger used in the polymerization reaction of the present invention is 500
ppm or less, preferably 300 ppm or less, particularly preferably i 50 ppm or less. Incidentally, it is preferable that the acid scavenger used be purified in advance by distillation.

The general solution polymerization method is diamine compound (
Mixture of 1) and (2) - The amide-based solvent is dissolved in the mixed solvent. The ratio of the charged seven-mer to the solvent is 10-50% (wt monomer/vol solvent, preferably 20-40%).

Furthermore, a predetermined amount of pyridine and/or N,N-sialkylaniline compound is added to the mixed system as a scavenger for hydrogen chloride generated during the reaction. The amount of pyridine added as an acid scavenger is not particularly limited, but basically it is preferably 1.0 to 3.0 times the mole of the theoretical amount of hydrogen chloride generated during the reaction, more preferably 1.0 to 3.0 times the mole. It is 2.0 times the mole.

If the amount of pyridine added as an acid scavenger is large relative to the reaction solvent used, pyridine acts as a poor solvent for the polymer, making the solution during the reaction non-uniform, resulting in high viscosity and hindering the purification process. .

The ratio of the amount of pyridine to the amount of the reaction solvent is 172 or less by volume, preferably 1/3 or less.

! Regarding the amount of added aniline compound, 1.5% of the theoretical amount of hydrogen chloride generated during one reaction.
A 0 to 1.2 times cell is preferable. If the amount added is less than 1.0, the effect as a hydrogen chloride scavenger decreases.

The resulting copolyamide also has a low viscosity.

On the other hand, if it is 1.2 or more, the polymer becomes insolubilized in the reaction solvent and one reaction system becomes non-uniform. the result.

It becomes difficult to purify the polymer. Furthermore, the viscosity of the resulting polymer also decreases with the amount added.

When the amine compound is dissolved in a mixed solvent of the above solvent and acid scavenger to form a homogeneous solution, an appropriate solution is added for the purpose of improving solubility.

It is also possible to heat the mixed solvent. The solvent for promoting solubility must be sufficiently dehydrated in advance by distillation or by using a drying agent. The heating temperature may be any temperature as long as the solvent used and the amine compound do not decompose, but the most preferred temperature is room temperature.

Next, the mixed solution is cooled with a suitable refrigerant to bring the temperature of the mixed solution to -10°C to 20°C, preferably 1°C to 10°C. As the refrigerant, water and/or ethylene glycol are generally preferred.

The method is not particularly limited.

Next, dicarboxylic acid halide is added to the cooled mixture of the diamine compound, acid scavenger, and reaction solvent under stirring, and stirring is continued for an appropriate period of time. What is the shape of the dicarboxylic acid halide when added?

Solid state (powder, flakes or pellets, etc.)
It can take any form, such as a solution dissolved in an appropriate solvent, or a molten state by heating, but is preferably in a solid state.

The rate of addition of the dicarboxylic acid halide into the mixed liquid is:
Depending on the temperature of the reaction solution at the time of addition, the temperature of one reaction system continuously increases to 70°C due to the heat of reaction (heat of polymerization), preferably 40°C.
The addition rate t of the dicarboxylic acid halide is set so as not to exceed
- Must be adjusted. The stirring speed when adding the dicarboxylic acid halide affects the degree of polymerization of the resulting polymer.
give effect.

The faster the stirring speed, the higher the degree of polymerization of the obtained polymer, which is preferable from the viewpoint of the physical properties of the polymer.

After the addition of the dicarboxylic acid halide, stirring is continued for an additional approximately 30 minutes to 1 hour while cooling as described above. The stirring speed at this time may be any speed, but it is preferably as fast as possible.

After the reaction under cooling as described above, approximately 1
The polymerization reaction is continued for 2 hours. The stirring speed at this time may be any speed, but it is preferable to use it as fast as possible in order to obtain a polymer with high viscosity.The roughness of the polymerization reaction system generally depends on the type and concentration of the acid scavenger. 1 In the present invention, nine pyridine and N, N-
1 when a sheaμkiμaniline compound is used as an acid scavenger
The reaction system is characterized in that the reaction system becomes a transparent homogeneous solution during and after polymerization.

Therefore, it is extremely convenient when solidifying and purifying the polymer by introducing the polymerization reaction solution into a poor solvent for the polymer.

Furthermore, since the reaction system is constantly homogeneous during polymerization, a polymer with a high degree of polymerization can be obtained.

On the other hand, when an acid scavenger other than the present invention 1, for example, triethyl μamine is used, the produced polymer becomes insolubilized in the reaction system, and the reaction system during and after the polymerization becomes a heterogeneous solution. For this reason 5
Reactive terminals are easily deactivated, leading to a decrease in polymer viscosity. Furthermore, the polymer was purified by the precipitation method described above.

When doing this, a good solvent for the polymer, e.g.
N,N-dimethyacetamide%N-methypyrrolidone, etc. must be added to the reaction system to dissolve the polymer and make the system homogeneous before proceeding.

As described above, the production method of the present invention is not only effective in increasing the viscosity of a polymer, but also facilitates purification of the polymer.

During polymerization, KM is added to the mixture solution in order to neutralize the hydrogen halide generated during the first polymerization before and during the first polymerization, and/or to facilitate the dissolution of the polymer in the reaction solvent. It is also possible to add substances.

Examples of such inorganic compounds are lithium chloride,
Preferred examples include Schwamm chloride, potassium chloride, lithium silate, lithium oxide, lithium hydroxide, calcium hydroxide, and calcium carbonate. Lithium chloride, calcium chloride, potassium chloride, etc. can be added before polymerization for the purpose of promoting dissolution of the polymer, but others are preferably added after polymerization for the purpose of neutralizing hydrogen halide generated. In addition, a preferable example of an organic compound having such an effect is propylene oxide. The substances can be added after polymerization II and/or after polymerization.

As other additives, a terminal capping agent can be used if necessary, and a compound having only one group that reacts with an amino group and an acid halide group is suitable as the terminal capping agent.

After soaking in the polymerization reaction, the resulting solution is mixed with methanol, which is a poor solvent for the polymer, water, etc., and the polymer is suspended as a solid. The solid polymer was then filtered and washed with water and methanol repeatedly to remove the solvent adsorbed onto the polymer.
Acid scavengers, hydrochloric acid, oligomers, etc. must be removed as much as possible. Thoroughly washed polymer at 130℃
~150'CK and vacuum drying to obtain the copolyamide of the present invention.

The amount of hydrochloric acid remaining in the polymer purified in this way is 50
It should be below 0 ppm, preferably below 200 ppm.

(Effects of the Invention) The method for producing a novel copolyamide of the present invention is characterized in that it not only yields a polymer with a high viscosity as shown in the examples below, but also is advantageous in purification because the reaction system is homogeneous. be.

(Examples) Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the Examples.

Example 1 Synthesis of poly(Inphthaloy #-4.4'-diaminodiphenylsulfone/piperazine (80/20)) copolymer Piperazine 1.72 t (0.02 mol), 4.4
'-Diamino Schiff C: / to phone 19.8 f (0
,08mol) i! Place in a 500 ml four-bottle flask equipped with a thermometer and a stirrer under a nitrogen stream. Additionally, pyridine 2 was added to this system as an acid scavenger.
8xl (0.2 mol) and 200 ml of N-methylpyrrolidone (NMP) as a reaction solvent were added.
dissolve.

isophthalic acid chloride while cooling the entire reaction system with ice.
48 f (0.10 mol) was slowly added under a nitrogen stream. The reaction system was stirred for about 60 minutes under water cooling and then for about 1 hour at room temperature. At this time, the reaction system was a red-colored homogeneous solution.

Then, the reaction solution was added to 1500 mt of methanol,
The polymer is precipitated. A series of purification steps including pulverization of the polymer using a household mixer, filtration, and washing with water was repeated several times to remove unreacted substances in the polymer and remove the solvent.

Finally, Polymer 1 was washed with methanol and dried at about 130 degrees under vacuum for about 48 hours.

The reduced viscosity (ηsp/C) of the copolyamide is 0.79 (
0.5 f/di NMP, 30°C).

Example 2.3 Synthesis of poly(Inphthaloyd l'v-4+4'-diaminodipheniform/bibewodin (80/20)) 81 combination In Example 1, m of pyridine was adjusted to 1.5% of the theoretical amount of hydrogen chloride generated. Everything was carried out in the same manner as in Example 1 except that the molar ratio was 35 times, u, and 1.75 times.

Both reaction systems were homogeneous solutions, and the reduced viscosities of the obtained polymers were 1.17 and 1.30, respectively, which were high polymers.

Example 4.5.6 Synthesis of poly(inphthaloy/l/-4,4'-diaminodiphenyl/piperazine(80/20l) copolymer In Example 1.2.3, one reaction solvent was NMP The reaction system was a homogeneous solution, and the reduced viscosity of the obtained polymers was 0.77, 1.19°1.3
0, indicating a high polymer.

Comparative Examples 1 and 2 In Example 1, one reaction solvent INM was used without using an acid scavenger.
The reaction system was carried out in the same manner as in Example 1 except that P' or DMAc was used. All of the reaction systems were homogeneous solutions, but the reduced viscosities of the obtained polymers were 0.37 and 0.52, respectively, indicating that they were low polymers. Met.

Comparative Examples 3, 4.5 In Examples 4 and 5.6, all examples were Example 4 except that triethylamine (TEA) was used instead of the acid scavenger Py.
．． This was done in the same manner as 5.6.

Both reaction systems were heterogeneous solutions, and the reduced viscosities of the resulting polymers were 0.64 and 0.41, respectively.

It was 0.32 and was a low polymer. Furthermore, as the amount of TEA added increased, the reduced viscosity of the produced polymer also decreased.

Example 7.8.9 Synthesis of poly(terephthaloyl-3,3'-diaminodiphenylsulfone/piperazine) copolymer In Example 1, substitution of 4,4'-diaminodiphenylsulfone, isphthalic acid chloride and pyridine To, 3.3
'-diaminodiphenylsulfone.

Using terephthalic acid chloride and diethylaniline,
The amount of piperazine relative to the total amount of diamine components is 20.30.
．． The same procedure as in Example 1 was carried out in a pan except that the amount was 50 mo1%.

All reaction solutions were homogeneous solutions, and the reduced viscosities of the obtained polymers were 0.79, 0.86, and 0.77.

Example 10.11.12.13 Synthesis of poly(terephthaloy/l/-4,4'-diaminodiphe diphon/pibefujin copolymer) In Example 7, 3,3'-diaminodiphe=〃sphonno Instead, using 4,4/-diaminodiphenylsulfone, 1. The amount of piperazine relative to the total amount of diamine components was 10
．． All the O reaction solutions were homogeneous, and the reduced viscosities of the obtained polymers were 1.18, 1.35, 1. .10
.

The viscosity was as high as 0.99.

Example 14 Poly(terephthaloy!-3,3]-diaminodiphenylene)
Synthesis example of sulfone-4,4'-diaminodiphenylsulfone/pibewodine) copolymer In Example 7, 3,3'-diaminodiphenylsulfone and 4, The following procedure was carried out in the same manner as in Example 7, except that an equal amount of 4'-diaminodiphenylsulfone was used.

The reaction solution was a homogeneous solution, and the resulting polymer had a high reduced viscosity of 1.05.

Comparative Examples 6 and 7 The same procedures as in Example 7 were carried out except that in place of the acid scavenger DEAO, no acid scavenger was used or TEAt was used.

When no acid scavenger was used, the first reaction solution was a homogeneous solution, but the reduced viscosity of the obtained polymer was as low as 0.30. In the latter case, the reaction solution was a heterogeneous solution, and the resulting polymer had a low reduced viscosity of 0.17.

Example 15.16.17 Synthesis of poly(terephthaloy/I/-3,3'-diaminodiphenylsulfone/trans-2,5-dimethylpiperazine) copolymer In Example 7.8.9, DK was substituted for piperazine. ,)
Except that trans-2,5-dimethylpiperazine was used and the amount of trans-2,5-dimethylpiperazine was 20.30+50 mol based on the total amount of diamine components.
It was carried out in the same manner as in Example 7.8.9 in a pan.

All reaction solutions were homogeneous solutions, and the reduced viscosities of the obtained polymers were 0.73, 0.59, and 0.50.

Example 18 Synthesis of poly(terephthaloy 1v-3,3'-diaminodiphenylsulfone/trans-2,5-dimethylpiverazine copolymer) Except that dimethylaniline was used instead of the acid scavenger DEA in Example 15. All were performed in the same manner as in Example 15.

The reaction solution was a homogeneous solution, and the reduced viscosity of the nine polymers obtained was 0.53.

Example 19.20.21.22 Poly(terephthaloyv-3+3'-diaminodiphenylsulfone/trans-2,5-dimethylpiperazine)
Synthesis of Copolymer In Example 10.11.12.13, instead of piperazine! The same procedure as in Example 10.11.12.13 was carried out in a pan except that lance-2,5-dimethylpiperazine was used.

All reaction solutions were homogeneous, and the reduced viscosities of the obtained polymers were 1.04, 0.91, and 0.86.

The viscosity was as high as 0.72.

Example 23.24 Poly(terephthaloyv-333'-diaminodiphenylsulfone-4,4'-diaminodiphenylsulfone/
Synthesis of (2,5-dimethylpiperazine) copolymer In Example 15, 3,3'-diaminodiphenyi sulfone and 4,4'-diaminodiphenyi sulfone were used instead of 3,3'-diaminodiphenyi The O2 reaction solution was a homogeneous solution, and the reduced viscosity of the resulting polymer was 0.5%. The viscosity was as high as 83 and 0.70.

Comparative Example 8 In Example 15, TEA was used instead of the acid scavenger DEA.
Everything was carried out in the same manner as in Example 15, except that .

In this case, the reaction solution was a heterogeneous solution), and the resulting polymer had a low reduced viscosity of 0.25.

Claims (1)

[Scope of Claims] 1. A diamine component in which the molar ratio of the following diamine compounds (1) and (2) is 95/5 to 35/65 and an aromatic dicarbonate represented by the following general formula (3). An acid halide compound and an organic solvent and pyridine and/or N,N
- A method for producing a copolyamide, which comprises polymerizing in the presence of a dialkylaniline. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (However, R^1 and R^2 are hydrogen atoms or hydrocarbon groups having 1 to 12 carbon atoms, R^3 and R^4 are hydrogen atoms,
Or a monovalent organic group having no active hydrogen, n_1, n
_2 represents 0 or a natural number from 1 to 3. )▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) (However, R^5, R^6, R^7, R^8, R^9,
R^1^0, R^1^1, and R^1^2 represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms. ) XOC-R-COX (3) (However, X represents a halogen atom, and R represents an organic group having 2 to 15 carbon atoms which may contain a hetero atom.) 2, R^1, R^ 2, R^3, R^4, R^5, R^6
, R^7, R^8, R^9, R^1^0, R^1^1,
The method for producing a copolyamide according to claim 1, wherein R^1^2 is a hydrogen atom and R is a phenylene group. 3, R^1, R^2, R^3, R^4, R^6, R^7
, R^8, R^9, R^1^0, R^1^2 are hydrogen atoms, R^5, R^1^1 are methyl groups, and R is a phenylene group. A method for producing a copolyamide according to item 1.