JPH0551615B2 - - Google Patents

Description

[Detailed description of the invention]

(Industrial Application Field) The present invention relates to an aromatic copolyamide made from N,N'-bis(4-aminophenyl)isophthalamide. Furthermore, a method for producing the aromatic copolyamide, which comprises condensing terephthalic acid chloride to a mixture of paraphenylenediamine and N,N'-bis(4-aminophenyl)isophthalamide as an aromatic diamine compound, and further from this polymer solution. The present invention relates to manufactured high strength and high modulus heat resistant fibers and films. (Prior technology) Aromatic polyamides have extremely high melting temperatures and glass transition temperatures (in fact, thermal decomposition often occurs from the melting point), and have excellent physicochemical properties such as excellent thermal stability and chemical resistance. It has properties. Fibers made from such aromatic polyamides can be used to make heat-resistant fibers by taking advantage of their excellent thermal stability or rubber reinforcements such as tire cords by taking advantage of their excellent mechanical properties such as high tensile strength and elastic modulus. It is used as materials, composite materials, etc. In particular, ultra-high performance aromatic polyamide fibers that have high strength, high elastic modulus, and high heat resistance are manufactured through liquid crystal spinning.When the spinning stock solution forms a solution liquid crystal, it is processed into a liquid crystal spinning process called a gas-gap wet spinning method. Ultra-high performance fibers can be produced through spinning, and a typical example of this is poly(paraphenylene terephthalamide) fiber, which is generally known as Dupont's Kevlar. There is. However, aromatic polyamides and copolyamides, such as poly(paraphenylene terephthalamide), in which the molecular chains extend linearly from both ends of the aromatic ring in a direction parallel to the molecular chains, have ultra-high strength and high elastic modulus. Despite possessing such properties, poly(paraphenylene terephthalamide) is difficult to manufacture due to extremely low solubility in solvents.In fact, poly(paraphenylene terephthalamide) dissolves only in extremely limited solvents; is limited to a mixed solution of hexamethylphosphorylamide and N-methylpyrrolidone to which a strong inorganic acid such as concentrated sulfuric acid or an inorganic salt such as lithium chloride is added. Only strong inorganic acids can be used. When such polyamides are industrialized, many problems arise, such as corrosion of equipment due to the use of strong acids, dangers in handling, and difficulties in waste liquid treatment, and complicated operations are required to dissolve the polymer in a solvent. It has certain drawbacks. In addition, sulfuric acid rapidly separates from between the molecular chains in the coagulation solution during coagulation, inducing "fibril" formation, which is a disadvantage of linear strongly linear polyamides. Fiber fibrillation and cracking within the fiber is a fatal drawback of aromatic polyamide fibers, which have a variety of uses as reinforcing materials. It lacks chemical resistance and is a drawback in its role as a reinforcing material for rubber, cement, etc., which is a factor that hinders the expansion of its uses. To increase the solubility of rigid polyamides and copolyamides with straight molecular chains extending straight at both ends of the aromatic ring, "meta" linkages such that the molecular chains can be bent at both ends of the aromatic ring are used. Methods of introducing a unit or a rotatable bond between aromatic rings are already widely known. For example, when metaphenylene units are introduced between the amide bonds of a highly linear copolyamide, the solubility of the copolyamide can be increased. However, as the proportion of metaphenylene units in the molecular chain increases, the mechanical properties, particularly the elastic modulus, of fibers made from such copolyamides are significantly reduced. Efforts to increase solubility by introducing modification units into linear strongly linear polyamide molecular chains have been worldwide, and although various attempts have already been described in many literatures and patents, Many could not overcome the decline in physical properties. For example, U.S. Patent No. 4,075,922 states that the following formula [However, Y is -O-, The invention of a copolyamide into which modification units such as the following are introduced has been announced, and the copolyamide was thermally stretched at a high temperature after fiber production to overcome the deterioration in physical properties. However, the following formula used to prepare the copolyamide: Since the manufacturing cost of the 3,4'-diaminodiphenyl ether monomer is high, it is economically difficult. (Problems to be Solved by the Invention) The present invention is directed to a polymeric polymer with fluidity and stability that is economical and capable of producing fibers and films with thermal stability, high strength, and high modulus of elasticity. The object of the present invention is to provide a new diamino monomer whose solubility can be improved so that a combined solution can be produced, an aromatic copolyamide polymer produced therefrom, and a method for producing the same. Another object of the present invention is to provide fibers and films having high strength, high modulus, and high heat resistance that are basically produced directly from the polymer solution of this new aromatic copolyamide. (Means for Solving the Problems) In the present invention, N,N'-bis(4-aminophenylene)isophthalamide of the formula (1) shown below is used to combine with paraphenylene diamine, an existing para monomer. The method for producing aromatic polyamide fibers described above is carried out by mixing at a constant ratio, adjusting the ratio of para-linking units and meta-linking units, and adjusting the mutual distance of meta-linking units to maintain a high degree of polymerization. It enables the production of films and fibers. The aromatic copolyamide of the present invention is an aromatic copolyamide having an intrinsic viscosity of 1.0 to 6.0 and consisting of a structural unit represented by the following formula (1). In the above formula, x and y are the molar ratios of N,N'-bis(4-aminophenyl)isophthalamide and paraphenylenediamine to the number of moles of the entire condensed diamine monomer, and the value is x is 0.12 to 0.9, and y is 0.88 to 0.1. The copolyamide of the above formula (1) is prepared by dissolving an alkali metal salt in a tertiary amide solvent and adding a tertiary amine as an acid scavenger to the polymerization solvent. -Aminophenyl) isophthalamide and paraphenylenediamine in a molar ratio of 12:88 to 90:10, and are produced by subjecting terephthalic acid chloride to low-temperature polycondensation. This polymer solution is hot stretched to obtain aromatic copolyamide fibers or films with high strength and high modulus. The film produced by this film casting is an extremely transparent, high-strength, and highly heat-resistant film. The concentration and viscosity of a polymer solution produced by copolymerization are adjusted, and fibers produced by directly spinning the same have excellent mechanical and thermal properties. The tensile strengths of the film and fibers range from 100 to 150 Kg/mm ² and from 10 to 15 g/den, respectively. In the present invention, the following formula (2) used as a polymerization monomer, The method for producing N,N'-bis(4-aminophenyl)isophthalamide is disclosed in Korean Patent No. 11475.
The following equation (3) presented in No. This method is basically the same as the method for producing N,N'-bis(4-aminophenyl)terephthalamide.
That is, isophthalic acid halide (4) and two equivalents of paranitroaniline (5) are reacted as shown in the following reaction formula (A).
After condensation at low temperature to synthesize N,N'-bis(4-nitrophenyl)isophthalamide, this was hydrogen-reduced using Ranene nickel as a catalyst to form N,N'-bis(4-nitrophenyl)isophthalamide.
N'-bis(4-aminophenyl)isophthalamide (2) can be produced. The copolyamide of the present invention is produced by the following reaction formula (B) in which terephthalic acid chloride of formula (7) is reacted with a mixture of diamine monomer of formula (2) and paraphenylene diamine of formula (6) at a fixed ratio. ) can be produced according to the route. To obtain the copolyamide, N,N'-bis(4-aminophenyl)isophthalamide monomer
Without using (2), to a mixture of isophthaloyl chloride (4) and terephthaloyl chloride (7) at a certain ratio,
Even if paraphenylenediamine (6) is similarly reacted according to the following reaction formula (C), the objective can be achieved to some extent. However, as shown in reaction formula (B) of the present invention, N,
When N'-bis(4-aminophenyl)isophthalamide (2) is used as a polymerization starting material, hydrogen chloride Since the generation is small (up to 1/2), copolyamides with a high degree of polymerization can be produced. Further, by using the monomer (2) of the present invention, hydrogen chloride generated in reaction formula (B) can be easily removed, and a copolyamide with a high degree of polymerization can be produced. Therefore, the use of monomer (2), which is a polymerization intermediate, in the present invention makes it possible to easily produce a copolyamide with a high degree of polymerization having basically the same molecular structure, and By increasing the relative distance of the meta-linking rings in the polymer molecular chain, loss of crystallinity can be prevented to the maximum extent, so that deterioration of mechanical properties can be prevented while increasing solubility. The copolyamide (1) of the present invention basically comprises (1a)
It consists of a structural unit and (1b) a composition of structural units. In order to maintain both good solubility and mechanical strength, (1a) structural units should be incorporated in the copolyamide of the present invention in an amount of 12 to 90% based on the total repeating units, especially 12 to 90%. 30% effective. As mentioned above, the copolyamide (1) of the present invention comprises N,
N'-bis(4-aminophenyl)isophthalamide (2) and paraphenylenediamine (6) are mixed so that the ratio of structural units (1a) in the entire molecular chain is compatible with the purpose of the invention. It is produced by condensation polymerization with terephthalic acid chloride (7), and the polymerization method is basically the method conventionally used for polyamide polymerization, that is, interfacial polymerization, melt polymerization, solid polymerization, or solution polymerization method. However, in order to produce a copolyamide with a high degree of polymerization that is suitable for the purpose, it is preferable to carry out a solution polymerization method. To produce copolyamide by solution polymerization method, −
An organic solvent should be used in which the monomers and the resulting high molecular weight polymer can be dissolved at least partially in the temperature range of 20°C to 100°C, and an acid scavenger may be used if necessary. You can also. Metal halide salts of groups or groups of the periodic table can also be added to the polymerization solvent to increase the solubility of the polymer and the stability of the resulting polymerization solution. Amide solvents are suitable as organic solvents used in polymerization, and these solvents include N,N'-dimethylacetamide, N-methylpyrrolidone, hexamethylphosphorylamide, N-
Methylpiperidone. N,N,N',N'-tetramethylurea, N-methylcaprolactam, N,
N'-diethylacetamide, N-ethylpyrrolidone, N-acetylpyrrolidone, etc., especially N
-Methylpyrrolidone, hexamethylphosphorylamide, N,N'-dimethylacetamide or mixtures thereof are useful. To specifically describe the optimal polymerization method, N,
N'-bis(4-aminophenyl)isophthalamide in a molar ratio of 12-90%, paraphenylenediamine in a molar ratio of 88-10%,
After dissolving in the amine solvent so that the sum of the molar ratios of both diamines becomes 100%, the mixture is stirred while adding terephthalic acid chloride at a molar ratio of 100%. The reaction rate changes according to the ratio of diamine monomers, and the viscosity of the reactant increases sharply or gradually.
However, in reality, the polymerization reaction is completed within 24 hours. The amide solvent acts on the one hand as an acid scavenger for hydrogen chloride. The reaction temperature is suitably -20°C to 100°C, and particularly useful is -5°C to 50°C. The concentration of monomers added in the solution polymerization reaction determines the concentration of the polymer solution produced and the degree of polymerization of the polymer, and the degree of polymerization that is optimal for the production of products such as fibers and films. The input monomer concentration, which determines the viscosity of the polymer solution, varies slightly depending on the ratio of both diamine monomers, the choice of solvent, and the reaction temperature. Generally, the monomer concentration during solution polymerization is suitably between 4 and 20% by weight, particularly between 6 and 15% by weight. It is further useful to add the above-mentioned solubility enhancer before, during or after the reaction during the polymerization operation, and lithium chloride, calcium chloride, etc. are particularly useful, and are added in an amount of 1 to 5% by weight. Furthermore, it is effective to add the above-mentioned acid scavenger or neutralizing agent before, during or after the reaction, and pyridine, picoline, quinoline, etc. are useful, and they are added in an amount of 1 to 50% by weight. A copolyamide polymer solution produced by such a solution polymerization method is directly used as a stock solution for producing a molded article (for example, a spinning stock solution). on the other hand,
It is also possible to add an excess amount of water to this polymer solution, collect the polymer precipitate by crushing it with a mixer, wash it with water, dry it, redissolve it in an appropriate solvent, and use it as a spinning stock solution. However, the key point of the present invention is a method for directly molding a polymer solution obtained by solution polymerization. The aromatic copolyamide produced by the production method of the present invention has excellent solubility, and fibers, films, etc. produced therefrom exhibit excellent mechanical properties. To evaluate the degree of polymerization of the copolyamide polymers produced according to the present invention, the dried polymer was 97%
Dissolve it in sulfuric acid to a concentration (c) of 0.5 g/dl, measure the relative viscosity (ηrel) at 30°C, and convert it to the intrinsic viscosity using the following formula: ηinh=1n(ηrel)/C for evaluation. The degree of polymerization suitable for the purposes of the present invention is one in which the produced polymer has an intrinsic viscosity of 1.0 to 6.0, particularly 2.0.
Polymers with an intrinsic viscosity of ~5.0 are effective for producing polymer solutions at appropriate temperatures, and fibers, films, etc. produced therefrom retain excellent mechanical properties and heat resistance. Utilizing the polymer solution directly as a spinning stock solution,
Fibers are produced by spinning using methods such as dry spinning, wet spinning, and septum wet spinning. In particular, U.S. Pat.
Dyrwet spinning, such as that described in US Pat. No. 3,671,542, is useful. More specifically, the spinning stock solution is maintained at a temperature of 15 to 90°C, particularly room temperature to 70°C, and passed through a spinning nozzle (e.g.
It is injected through a spinneret diameter: 0.1 mm, number of spinnerets: 12). The injected solution is pulled while passing through an air gap (for example, 1 to 2 cm) between the spinning nozzle and the coagulating liquid, and is instantly coagulated into the coagulating liquid, after which the produced fiber is wound. take. This gas-gap wet spinning method is different from the normal wet spinning method in that an air gap is provided between the spinning nozzle and the coagulating liquid, and the spinning solution is injected from this air gap through the spinning nozzle. The fiber is pulled due to the difference between the injection speed and winding speed. The properties of the produced fibers are N,N'-bis(4
-aminophenyl)isophthalamide in molar ratio
For fibers loaded with 12-88%, the strength is 10-15
The g/den and elastic modulus are excellent, ranging from 100 to 400 g/den. At other mixing ratios, the strength and elastic modulus ranges from 4 to 13 g/den and 70 g/den, respectively.
~210g/den. Copolyamide fibers and casted films produced by the above-mentioned production method can be stretched at high magnification, and as a result of stretching, fibers, films, etc., having excellent mechanical properties and heat resistance are produced.
The stretching ratio useful for producing the high-performance fibers, films, etc. of the present invention is from 1:1.3 to before cutting,
In particular, it exhibits excellent mechanical and thermal properties in the drawing ratio range of 1:4 to 1:9. Stretching is carried out on a hot plate or a clyindrical heating rod within a temperature range from above the glass transition temperature to a temperature range at which thermal embrittlement does not occur rapidly. The hot stretching is suitably carried out at a temperature of 250 to 500°C, particularly effectively carried out at a temperature of 300 to 450°C. The copolyamides, fibers, films, etc. produced by the production method of the present invention are extremely stable thermally, and according to differential thermal analysis and gravimetric thermal analysis,
Decomposition occurs rapidly above 450℃, and it is useful up to 400℃ for short-term use and 250℃ for long-term use. (Effect of the invention) A copolyamide with a high degree of polymerization can be produced by the production method of the present invention, and the produced copolyamide has fluidity and stability, and fibers, films, etc. produced therefrom can be produced. Because it has excellent mechanical properties such as high strength and high modulus and thermal stability, it is used as an industrial material for tire cords, other reinforcing materials such as rubber and resin, heat-resistant insulation materials, heat-resistant transparent films, etc. It has many uses. (Examples) Hereinafter, the present invention will be explained in more detail with reference to the following examples. However, it should be understood that these examples are merely illustrative of the present invention, and the scope of the present invention is not limited to these implementations. Example 1 N,N′-bis(4-aminophenyl)isophthalamide and paraphenylenediamine,
Production of polymers reacted with terephthalic acid chloride by mixing in a ratio of 12.5:87.5. 240 ml (2.58 mol) in a volume 1 taped rectangular flask equipped with a stirrer, thermometer and nitrogen inlet.
of N,N'-dimethylacetamide, 7.2 g (0.17
mol) of lithium chloride, 2.595 g (0.0075 mol)
N,N'-bis(4-aminophenyl)isophthalamide and 5.67 g (0.00525 mol) of paraphenylenediamine were added and stirred to obtain a solution.
Maintain the temperature of this solution at 30°C and add 15.2 ml
After adding (0.19 mol) of pyridine, 12.26 g
(0.06 mol) of terephthalic acid chloride was added,
Stir vigorously. After 10 minutes of addition, the viscosity gradually increased. This mixed solution was continuously stirred for 3 hours and then left at room temperature for 1 day. The produced polymer solution was extremely stable and no separation of states occurred even after 30 days. This can be directly film casted to produce a film, or it can be spun to produce fibers. In order to obtain a solid polymer powder, an excess amount of water was added to the produced polymer solution, and the mixture was pulverized in a mixer to precipitate the polymer in a powder state. The recovered polymer was washed several times with water to completely remove the solvent, and then dried in a vacuum dryer at 80° C. for 6 hours or more. The obtained polymer was a soft yellow powder, and its intrinsic viscosity was 3.93. Example 2 N,N'-bis(4-aminophenyl)isophthalamide and paraphenylenediamine
Production of polymers mixed in a ratio of 12.5:87.5 and reacted with terephthalic acid chloride. In this example, N-methylpyrrolidone was used as the polymer solvent. In a 1 capacity faucet rectangular flask equipped with a stirrer, thermometer and nitrogen inlet,
9.6 g of N-methylpyrrolidone in 240 ml (2.49 moles)
(0.23 mol) of lithium chloride and 2.595 g (0.0075
mole) of N,N'-bis(4-aminophenyl)
Isophthalamide and 5.67 g (0.0525 mol) of paraphenylenediamine were added and stirred to obtain a solution. Maintain the temperature of this solution at 25°C and
After adding 13.7 ml of pyridine, 12.26 g (0.06 mol) of terephthalic acid chloride was added all at once and stirred vigorously. After 10 minutes of addition, the viscosity gradually increased. This mixed solution was continuously stirred for 3 hours and then left at room temperature for 1 day. This polymer solution was also extremely stable. This can be used directly to produce fibers, films, etc. In order to obtain a solid polymer powder, an excess amount of water was added to the produced polymer solution, and the mixture was pulverized in a mixer to precipitate the polymer in a powder state. The recovered polymer was washed several times with water to completely remove the solvent, and then dried in a vacuum dryer at 80° C. for 6 hours. The obtained polymer was a soft yellow powder, and its intrinsic viscosity was 3.44. Example 3 N,N'-bis(4-aminophenyl)isophthalamide and paraphenylenediamine,
Production of polymers reacted with terephthalic acid chloride by mixing in a ratio of 12.5:87.5. In this example, calcium chloride was used as the alkali metal salt. In a 1 capacity faucet rectangular flask equipped with a stirrer, thermometer and nitrogen inlet,
240 ml (2.58 mol) N,N'-dimethylacetamide, 6.2 g (0.06 mol) calcium chloride, 2.59
g (0.0075 mol) of N,N'-bis(4-aminophenyl)isophthalamide and 5.67 g (0.00525
mol) of paraphenylenediamine was added and stirred to obtain a solution. The temperature of this solution was maintained at 30° C., and 10.4 ml (0.13 mol) of pyridine was added thereto, and then 12.26 g (0.06 mol) of terephthalic acid chloride was added all at once and stirred vigorously. The viscosity gradually increased 10 minutes after addition, but remained unchanged after 1 hour. After stirring this polymer solution for 3 hours, it was left to stand at room temperature for 1 day.
This polymer solution was extremely stable. This was used directly to produce fibers, films, etc. In order to obtain a solid polymer powder, an excess amount of water was added to the produced polymer solution, and the mixture was pulverized in a mixer to precipitate the polymer in a powder state. The recovered polymer was washed several times with water to completely remove the solvent, and then dried in a vacuum dryer at 80° C. for 6 hours or more. The obtained polymer was a soft yellow powder, and its intrinsic viscosity was 3.60. Example 4 N,N′-bis(4-aminophenyl)isophthalamide and paraphenylenediamine,
Production of polymers mixed in a ratio of 12.5:87.5 and reacted with terephthalic acid chloride. In this example, a 1:2 (by volume) mixture of hexamethylphosphorylamide and N-methylpyrrolidone was used as the polymer solvent. A taped rectangular flask equipped with a stirrer, thermometer and nitrogen inlet was
86 ml (0.46 mol) hexamethylphosphorylamide and 160 ml (0.17 mol) N-methylpyrrolidone,
6.9 g (0.14 mole) lithium chloride, 2.595 g
(0.0075 mol) of N,N'-bis(4-aminophenyl)isophthalamide and 5.67 g (0.0525 mol) of paraphenylenediamine were added and stirred to obtain a solution. The temperature of this solution was maintained at 20° C., and 22.8 ml (0.28 mol) of pyridine was added thereto, followed by 12.26 g (0.06 mol) of terephthalic acid chloride at once and stirred vigorously. After addition, 10
After minutes, the viscosity gradually increased, but after 1 hour, the viscosity did not increase. This polymer solution was continuously stirred for 3 hours and then left at room temperature for 1 hour. This polymer solution was extremely stable. This can be used directly to produce fibers, films, etc. In order to obtain a solid polymer powder, an excess amount of water was added to the produced polymer solution, and the mixture was pulverized in a mixer to precipitate the polymer in a powder state. The recovered polymer was washed several times with water to completely remove the solvent, and then dried in a vacuum dryer at 80° C. for 6 hours or more. The obtained polymer was a soft yellow powder, and its intrinsic viscosity was 3.08. Example 5 Preparation of copolyamide fibers of N,N'-bis(4-aminophenyl)isophthalamide (12.5)/paraphenylenediamine (87.5)/terephthalic acid chloride (100). 10 g of the polymer solution (IV = 3.93) prepared by the method of Example 1 was placed in a 500 ml one-necked rectangular flask, and then distilled under reduced pressure until the concentration of the polymer solution was 18%.
The solvent was removed so that The polymer solution (spinning stock solution) whose concentration had been adjusted was transferred into a spinning machine and the pressure was reduced for 30 minutes to remove air. After maintaining the temperature at 30°C, it was passed through a 400 mesh filter.
The passed spinning solution has a spinneret diameter of 0.1 mm and a spinneret number of 12.
The linear velocity of the injection liquid through the spinning nozzle at the mouth was set at 15 m/
After injecting the spinning solution as min.
The fibers were coagulated in a coagulating liquid, formed into fibers, and wound around a winding roller at a winding speed of 60 m/min. The manufactured fibers were soaked in water for at least one day to remove residual solvents and alkali metal salts, and then dried.
The dried fibers were hot drawn within 10 seconds at a drawing ratio of 1:6 on a hot plate with a surface temperature of 300°C. The manufactured fiber has a density of 3.3 den, a strength of 13.2 g/den, and an elongation of 7.
%, and the elastic modulus was 275 g/den. Example 6 Preparation of a polymer in which N,N'-bis(4-aminophenyl)isophthalamide and paraphenylenediamine were mixed in different ratios and reacted with terephthalic acid chloride. Same as Example 1, 240 ml as polymer solvent
(2.58 mol) of N,N'-dimethylacetamide,
Using 7.2 g (0.17 mol) of lithium chloride as the alkali metal salt and 15.2 ml (0.19 mol) of pyridine as the acid scavenger, N,N'-bis(4-aminophenyl)isophthalamide and paraphenylenediamine were combined. , mixed in various ratios so that the sum of the moles of both diamines is 0.66 moles, and 12.26 g
(0.06 mol) of terephthalic acid chloride was reacted. Table 1 shows copolyamides produced by varying the ratio of diamine monomers.

【table】

[Table] Example 7 Production of copolyamide fiber In the same manner as in Example 5, N,N'-bis(4-
Fibers were produced from copolyamides having a ratio of 20/80 to 90/10 of aminophenyl)isophthalamide and paraphenylenediamine. The manufacturing conditions are as shown in Table 2 below.

【table】

Claims (1)

[Scope of Claims] 1. An aromatic copolyamide having an intrinsic viscosity of 1.0 to 6.0 and comprising a structural unit represented by the following formula (1). In the above formula, x and y are the molar ratios of N,N'-bis(4-aminophenyl)isophthalamide and paraphenylenediamine to the number of moles of the entire condensed diamine monomer, and the value is x is 0.12 to 0.9, and y is 0.88 to 0.1. 2 Intrinsic viscosity is 2.0 to 5.0, x is 0.12 to 0.7,
The aromatic copolyamide according to claim 1, wherein y is from 0.88 to 0.3. 3 In a polymerization solvent in which an alkali metal salt is dissolved in a tertiary amide solvent and a tertiary amine is added as an acid scavenger, N,N'-bis(4-aminophenyl)isophthalamide and paraphenylene diamide are dissolved. and amine, the mixing ratio of which is 12:88 in molar ratio.
Claim 1, characterized in that terephthalic acid chloride is subjected to low-temperature polycondensation to a mixture having a ratio of 90:10 to 90:10.
A method for producing the aromatic copolyamide described. 4. The manufacturing method according to claim 3, wherein the mixing ratio of 4N,N'-bis(4-aminophenyl)isophthalamide and paraphenylenediamine is 12:88 to 70:30 in molar ratio. 5 The tertiary amide solvent is N,N'-dimethylacetamide, N-methylpyrrolidone, hexamethylphosphorylamide; N,N',N'-tetramethylurea;N,N'-diethylacetamide,
The method according to claim 3 or 4, wherein the method is one or a mixture of two or more selected from N-ethylpyrrolidone, N-methylcaprolactam and N-acetylpyrrolidone. 6. The manufacturing method according to any one of claims 3 to 5, wherein the alkali metal salt is lithium chloride or calcium chloride. 7. The manufacturing method according to any one of claims 3 to 6, wherein the amount of the alkali metal salt used is 1 to 5% by weight. 8. The manufacturing method according to any one of claims 3 to 7, wherein the tertiary amine is pyridine, picoline, or quinoline. 9. The manufacturing method according to any one of claims 3 to 8, wherein the amount of tertiary amine used is 1 to 50% by weight. 10. An aromatic copolyamide fiber or film having high strength and high elastic modulus obtained by hot stretching the aromatic copolyamide polymer solution according to claim 1. 11 The stretching temperature is 250 to 500℃, and the stretching ratio is
The fiber or film according to claim 10, obtained at 1.3 to 9 times. 12 The stretching temperature is 300 to 450℃, and the stretching ratio is
The fiber or film according to claim 10 or 11, obtained at a ratio of 1.3 to 9 times.