JPS61136519A - Production of polyarylate - Google Patents

Abstract

PURPOSE:To produce a polyarylate economically in good operability, by reacting an aromatic diol, an aromatic dicarboxylic acid and an aliphatic carboxylic acid anhydride as starting materials in a specified kneading condition by using a screw kneader. CONSTITUTION:At least either of the aromatic diols of formula I (wherein R1 and R2 may be the same or different and are each H, 1-20C alkyl, 6-20C aryl or a halogen, n1 and n2 are each 1-4, R3 is 2-8C alkylene, 6-8C arylene or the like, and n3 is 0 or 1) and/or formula II (wherein R4-R6 may be the same or different and are each H, 1-8C lower alkyl, or a halogen, n4 and n5 are each 1-4, and n6 is 1-3), at least one aromatic dicarboxylic acid (prefer ably, isophthalic acid) and at least 1-8C aliphatic carboxylic acid anhydride (preferably, acetic anhydride) are melt-polymerized by kneading in a screw kneader in a condition of formula III [wherein P is the net power requirement of an impeller (kg) of a screw kneader, and V is the weight (kg) of polymer] to form a polyarylate of an average degree of polymerization >=40.

Description

Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a method for producing a polyarylate having excellent heat resistance, and more specifically to a method for producing a polyarylate having excellent heat resistance. The present invention relates to a method for economically and efficiently producing polyarylate with excellent properties.

(Prior Art) Fully aromatic polyarylates have been known as heat-resistant polymers. For example, 4-hydroxybenzoic acid homopolymer or copolymer (Sumitomo Chemical's product name Econol), or 2,2-bis(4-hi)"roxyphenyl)-propane (hisphenol A: hereinafter abbreviated as BA). A polymer (for example, Unitika's product name U polymer) consisting of terephthalic acid (hereinafter abbreviated as TPA) and isophthalic acid (hereinafter abbreviated as IPA) was proposed in the past, and is now commercially available.

In particular, for the latter polyarylate, many manufacturing methods have been described in the literature, and these can be essentially divided into three methods. Namely, (1) an acid halide method in which an aromatic diol as an alkali metal salt and an aromatic dicarboxylic acid civalide are brought into liquid-liquid contact as a solution, and the reaction occurs in the solution or at the interface between the two phases; (2) the aromatic halide method; (3) A method in which an aromatic diol component is made into a diester derivative and then reacted with an aromatic dicarboxylic acid, and (3) an aromatic diol and a diaryl ester of an aromatic dicarboxylic acid are reacted.

(Problems to be resolved by the invention) However, in the method (1), an expensive solvent is inevitably used in the summer, which is not only uneconomical but also
There are disadvantages such as the need for further separation and purification steps.

On the other hand, when the above method <21, +3) is adopted, the melt viscosity rapidly increases as the degree of polymerization of the polyarylate increases, so first a prepolymer is produced and then a prepolymer is produced.

A method was adopted in which the prepolymer was pulverized into a fine powder and then subjected to homopolymerization [for example, for the method (2), US Pat. No. 3,684.766, US Pat. .148 Specification, etc.]. This method has the disadvantage that it is necessary to bring the prepolymer into contact with a crystallizing agent to crystallize the polymer, making the process complicated. Also, the prepolymer may have been solid-state polymerized by heating it below its melting point.

In some cases, the polyarylate prepolymer sticks 9
This method has the disadvantage that not only the workability is extremely deteriorated, but also the reaction rate is significantly reduced, making it impossible to obtain polyarylate with a high degree of polymerization at a practical rate.

Japanese Unexamined Patent Publication No. 57-2331 makes the following proposal in order to omit this crystallization step.

That is, a production method is disclosed in which a solvent such as diphenyl ether is co-present in the first step of JLJ production of a prepolymer, but in such a method, the crystallization step can be omitted.

There is a risk that the good physical properties inherent in the polymer may be impaired.

Despite the excellent properties of polyarylates obtained from aromatic diols and aromatic dicarboxylic acids, the method for producing polyarylates economically and with good operability has not been fully developed industrially. It could not be said that it had been done.

(Means for Solving the Problems 1 Structure of the Invention) The main object of the present invention is to provide a heat-resistant polyarylate particularly suitable for plasma spray coatings and molded products used at high temperatures. Excellent resistance and creep resistance,
The present invention provides a method for producing heat-resistant polyarylate having good high-temperature abrasion resistance and heat resistance economically and with good operability.

In order to achieve this objective, the present inventors have conducted extensive research into the production method of heat-resistant polyarylate using a screw-type mixed kneader using as raw materials, aromatic diol, aromatic dicarboxylic acid, and aliphatic carboxylic anhydride. The present invention was achieved based on the discovery that an extremely excellent manufacturing method is to react under specific crosstalk conditions.

The present invention has a secondary configuration. That is, the following general formula (
Using at least one aromatic diol represented by 1) and/or (II), at least one aromatic dicarboxylic acid, and an aliphatic carboxylic acid having 1 to 8 carbon atoms as raw materials, 1 is prepared using a screw-type mixed kneader. A method for producing polyarylate, which is characterized in that melt polymerization is carried out while kneading under the conditions shown by formula (1) to produce a polyarylate having an average degree of polymerization of 40 or more, where '# is preferably represented by the following general formula (I). The aromatic diol represented by or (it) is a compound represented by the following formula GV), (V) or (VD), and the aromatic dicarboxylic acid is IPA, and the aliphatic carboxylic anhydride is acetic anhydride. The gist of this paper is a method for producing polyarylate.

(In the formula, R1 and R2 represent the same or different groups selected from a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, and a polygonal atom, fil, 712 are 1 to 4 respectively
It is. R3 is an alkylev group having 1 to 8 carbon atoms, an alkylidene group having 1 to 8 carbon atoms, or an arylene group having 1 to 8 carbon atoms.

Cycloalkylene group having up to 9 carbon atoms, cycloalkylidene group having up to 9 carbon atoms, o, s, so.

represents a group selected from SO2 and CO; an3 is O or 1; ) (R6)n6 (wherein, R4, R5, R6 are hydrogen atoms, carbon atoms 1 to 8
represents a group of the same or different kind selected from a lower alkyl group having 1 to 3 ions, and a) rogen atom, n4゜n5 are each an integer of 1 to 4, and fi6 is an integer of 1 to 3. ) p/V≧2(1) (where P is the required stirring power of the screw-type mixed kneader (
□□□ and ■ indicate the polymer weight ft (1(q)).

) H3 It is necessary that the average degree of polymerization (Pn) of the heat-resistant polyarylate produced by the present invention is 40 or more, preferably 40 to 300. Particularly preferably 50 to 200. Optimally it is 65-150. When Pn is less than 40, various physical, mechanical, and chemical property values including the heat resistance described above are poor. On the other hand, if Pn is greater than 300, the melt viscosity increases, fluidity is impaired, melt polymerization becomes difficult, and the molding temperature becomes high, which is not preferable.

In the method for producing the heat-resistant polyarylate of the present invention, as a first step, aromatic diol, aromatic dicarboxylic acid, and aliphatic carboxylic anhydride are charged as raw materials into a screw-type, preferably twin-screw kneader, and heated. Next, the reaction is carried out under normal pressure or slightly reduced pressure to produce a prepolymer.

At this time, the aromatic diol and aliphatic carboxylic acid anhydride may be reacted in advance and then reacted with the aromatic dicarboxylic acid, but it is preferable to allow the king to coexist and react directly, in order to shorten the process. be.

Examples of aromatic dicarboxylic acids used in the present invention include:
TPA, IPA, 4,4'-dicarboxybiphenyl,
Bis(4-carboxyphenyl)meta 7.2.2'-Bis(2-carboxyphenyl)furopane, bis(4-carboxyphenyl)sulfone.

Bis(2-carboxyphenyl) ether, naphthalic acid, etc. are mentioned, and IPA is particularly preferably used. If necessary, a mixture of the above aromatic dicarboxylic acids may be used.

On the other hand, examples of aromatic diols used in the present invention include compounds represented by the above general formula (1) or (If), specifically, the above formulas (ffl), (V), (V
) and 7:l B A, 4.4'-(dihydroxyphenyl)-sulfone (bisphenol S di or less B
It is abbreviated as S. )9.10-dihydro-9-oxa-1
0-(2,5-dihydroxyphenyl)-phosphaphenanthrene-10-oquindo (hereinafter abbreviated as HCA/HQ) is particularly preferably used, but other bis-(2
-hydroxyphenyl)-methane, bis-(4-hydroxyphenyl)-methane, bis-(4-hydroxyphenyl)-2
,6-dimethyl-3-methoxyphenyl)-methane, 1
．． 1-bis-(4-hydroxyphenyl)-ethane, 1
,1-bis-(4-hydroxy-2-chlorophenyl)
-ethane, 1,3-bis-(3-methyl-4-hy)'roxyphenyl)-furopane.

2.2-bis-(3-improbyl-4-hydroxyphenyl)-propane, 4.4'-(dihydroxyphenyl)ether, 2.2'-bis-(4-hydroxyphenyl)-pentane, 3.3 '-Bis-(4-ζ droxyphenyl)-pentane, 2.2'-bis-(4-hydroxyphenyl)-hebutane, 4.4'-(dihydroxyphenyl)-sulfide, 4.4'-( dihydroxy 7
Ale)-sulfoxide, 4,4'-(dihydroxybenzophenone), hydroquino 7, etc. can also be used.

The aliphatic carboxylic acid/acid used in the present invention is:

It is an aliphatic carboxylic acid anhydride having 1 to 8 carbon atoms.

For example, acetic anhydride, chloroacetic anhydride, dichloroacetic anhydride, trichloroacetic anhydride, bromoacetic anhydride.

Glutaric anhydride, maleic anhydride, cono-phosphoric anhydride.

β-bromopropionic anhydride, propionic anhydride.

Examples include butyric anhydride, inbutyric anhydride, propyl acetic anhydride and the like, with acetic anhydride being particularly preferred. If the number of carbon atoms exceeds 8, the boiling point of the aliphatic carboxylic anhydride becomes too high and the reaction rate in the subsequent polycondensation step decreases, which is not preferable.

flCA/HQ used in the present invention is produced by reacting 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide represented by the following formula (1) with benzoquinone in a suitable solvent such as ethylcelonorb. It can be manufactured by

In the present invention, when producing a polyarylate prepolymer, the molar ratio of aromatic diol, aromatic dicarboxylic acid, and aliphatic carboxylic anhydride at the time of charging is preferably 1.
: 0.8 : 1 to 1 : 1.2 : 10° Particularly preferably 1 : 0.9 to 2 to 1.1 : 4
, optimally 1:1:2.

Further, in the present invention, an esterification reaction, a transesterification reaction, and a polycondensation reaction are involved. A catalyst is usually used to promote each of these reactions, and it is preferable to use, for example, one or more compounds selected from various metal compounds or organic sulfonic acid compounds. 7:l)
Examples of such metal compounds include anti-sulfur, titanium, germanium, and tin.

Zinc, aluminum, magnesium, calcium.

Compounds such as manganese and cobalt are used.

On the other hand, examples of organic sulfonic acid compounds include sulfosalicylic acid and 0-sulfobenzoic anhydride (hereinafter abbreviated as O3B).

), among which dimethyltin malate (hereinafter abbreviated as C8) is particularly preferably used. The amount of the catalyst added is as follows.

Preferably 0 per mole of structural unit of polyarylate
．． I
．． 5 x 10 to 50 x 10 moles, optimally 1 x
10 to 10 X 10 moles are used.

In the second step of producing the heat-resistant polyarylate in the present invention, the prepolymer obtained in the first step is usually melt-polymerized under high vacuum or in an inert atmosphere such as nitrogen. When is 4? Unless the reaction is carried out under certain crosstalk conditions, it is not possible to produce high quality polyarylate economically and with good operability in a short period of time as described above. That is, stirring and kneading at a level lower than the mixing conditions shown by the above formula (Ill) is not economical because it usually takes several tens of hours or more to raise the average degree of polymerization of polyarylate to 40 or more.

Next, the method of the present invention will be explained in more detail step by step.

In the first stage of polyarylate production, the temperature is usually below the boiling point of the aliphatic anhydride carboxylic acid under normal pressure,
Preferably at 100-160°C for 1-8 hours, particularly preferably at 120-160°C for 2-6 hours, most preferably at 140°C.
React at ~160°C for 2-5 hours.

Then, usually under reduced pressure (10 to 500 torr) =
Finally, the reaction is preferably carried out at 150-300°C for 1-8 hours, particularly preferably at 200-280°C for 2-6 hours, most preferably at 260-280°C for 2-5 hours. When reacted in this manner, a polyarylate prepolymer having an average degree of polymerization of about 20 is obtained in the first step of polyarylate production. In this case, even if the polyarylate prepolymer becomes granular and precipitates as a solid during the reaction, there is no particular problem as long as the reaction is operated under the crosstalk conditions of the present invention.

Next, in the second step of polyarylate production, the obtained polyarylate prepolymer is gradually melted in a bath-molten state.
Using an appropriate schedule, e.g., gradually increasing the temperature at a rate of 20° C./hour, the mixture is heated to a temperature higher than the melting point of the polyarylate produced under the cross-wire conditions of the above formula (1), and melt polymerized for about 4 to 15 hours. By that.

A polyarylate having Pn of 40 or more can be produced.

(Example) Hereinafter, the present invention will be explained in more detail with reference to Examples.

The average degree of polymerization of the polymers in the 9 examples was determined by gel permeability chromatography (HLC801 manufactured by Toyo Soda Co., Ltd.).
Type A) and 2. hexafluoroinglopanol.
39 using chloroform containing 5 mo 1% as a solvent.
It was determined by dividing the number average molecular weight measured at a temperature of °C by the molecular weight of the repeating unit. In addition, the glass transition temperature and melting point were measured using a differential calorimeter (DSC manufactured by PerkinElmer).
-2 type) at a heating rate of 20°C/min. On the other hand, two polyarylates according to the present invention were identified by infrared absorption spectrum, NMR spectrum, glass transition temperature and elemental analysis.

Example 1 Screw-type twin-screw kneader (TKVI manufactured by Toshin Co., Ltd.)
-5 type vacuum kneader) A reaction device was charged with BA and acetic anhydride in a molar ratio of 1:2 and IPA in an equimolar amount with BA.
1X10 mol was added, and 2
The reaction was allowed to take place while mixing for a period of time. This reaction product was further heated at 250°C under normal pressure for 2 hours, and further at 100 torr.
The reaction was carried out at 270°C for 2.5 hours. This reaction product had an average degree of polymerization of 21.

This reactant was further heated under a reduced pressure of 0.1 torr starting at 270°C, and the temperature was raised sequentially to carry out the reaction, and finally the temperature reached 33°C.
The temperature was raised to 5° C. and melt polycondensation was carried out for a total of 8 hours. At this time, the value of P/V was 2.54V/9.

The obtained polyarylate had an average degree of polymerization of 84. Melting point 32
It was a crystalline polymer with excellent color tone and transparency at 3°C.

In addition, this polyarylate has an infrared absorption spectrum, N
As analyzed by MR spectrum and elemental analysis, 9
The following results were obtained, and it was confirmed that the polyarylate had a repeating unit with the following structure.

That is, in the infrared absorption spectrum, the absorption based on C=O of the aromatic carboxylic acid ester is at 1775, and the absorption based on C=O is at 72.
Absorption of para-substituted aromatics was observed in 7 and 774. In addition, in the NMR spectrum, the absorption of hydrogen atoms of methyl groups based on the raw material acetate (1.5 pprn and 2.3 pprn)
ppm) was not observed. According to the results of elemental analysis,
C=77.18% (theoretical value 77.08%).

A result of H=5.02% (theoretical value 5.06%) was obtained.

Example 2 BS and acetic anhydride in a molar ratio of 1:2 and IPA in an equimolar amount to BS were charged into the screw-type twin-screw kneader reactor used in Example 1, and C8 was used as a catalyst to react with boria IJL/-.
1X10''-' mol was added to 1 mol of the structural unit of 1, and the mixture was reacted with stirring at 150°C under nitrogen atmosphere for 2 hours.
Further, the reaction was carried out at 275° C. for 2.5 hours at 100 torr. The reaction product had an average type density of 17.

This reactant was further heated under a reduced pressure of 0.1 torr starting from 275°C, and the temperature was raised sequentially to carry out the reaction, and finally 3
The temperature was raised to 20° C. and melt polycondensation was carried out for a total of 7 hours.

At this time, the value of P/V was 2.3 kw/Kg.

The obtained polyarylate has an average degree of polymerization of 46° and a melting point of 30.
It was a crystalline polymer with excellent color tone and transparency at 1°C.

In addition, this polyarylate has an infrared absorption spectrum, N
As analyzed by MR spectrum and elemental analysis, 9
The following results were obtained, and it was confirmed that the polyarylate had a repeating unit with the following structure.

That is, in the infrared absorption spectrum, the absorption based on C=0&C of aromatic carboxylic acid ester at 1781 is as follows.
Absorption of para-substituted aromatics was observed at 744 and 780. In addition, in the NMR spectrum, the absorption of hydrogen atoms of methyl groups based on the raw material acetate ester (1.5 ppm and 2.5 ppm).
3PI)m) was not observed. The result of elemental analysis is C.
= 61.65 inches (theoretical value 63.15 inches).

The results were obtained: H=3.32% (theoretical value 3.18%) and S=8.19% (theoretical value 8.43%).

Example 3 The f(CA/HQ) represented by the above formula (■) was prepared by reacting the phosphinic acid represented by the above formula ~Φ with p-benzoquinone at a temperature of 90°C in an ethylseronorp solvent. The obtained HCA/) (Q and acetic anhydride were charged in a molar ratio of 1=2 to the screw-type twin-screw kneader reactor used, and O3B was used as a catalyst per mole of the structural unit of polyarylate.

3 × 10 mol was added and reacted under nitrogen atmosphere at normal pressure 1500 for 2 hours with mixing, HCA/! (Diacetate of Q was synthesized.

This reaction product and IPA were further reacted at 270°C under normal pressure for 2 hours, and then vcroot, rr, and 270°C.
The reaction was carried out for 2.5 hours. This reactant has an average degree of polymerization of 1
)Met.

This reactant was further heated to 270C under a reduced pressure of 1 torr, and the temperature was raised sequentially to carry out the reaction, and finally to 35
The temperature was raised to 0° C., and melt polycondensation was carried out for 3 times in total for 12 hours.

At this time, the value of P/V was 3.1 kw/Kq.

The obtained polyarylate had an average degree of polymerization of 69. It was an amorphous polymer with a glass transition temperature of 219°C and excellent color tone and transparency.

In addition, this polyarylate has an infrared absorption spectrum, N
As analyzed by MR spectrum and elemental analysis, 1
The following results were obtained, and it was confirmed that the polyarylate had a repeating unit having the following structure.

That is, according to the infrared absorption spectrum, it is 1783'
K The absorption based on C=0 of aromatic carboxylic acid ester is at 735, and the absorption of para-substituted aromatic at 781 is at 8.
Absorption of asymmetric trisubstituted aromatics was observed at 91. Also,
In the Nλ4R spectrum, the absorption of the hydrogen atom of the methyl group based on the raw material acetate VC (1.5 ppm and 2.3 ppm)
pm) was not observed. According to the results of elemental analysis, C=6
9.01% (theoretical value 68.70%), H = 3.26 coefficient (
Theoretical value 3.33φ), P=6.55% (Theoretical value 6.82
The following results were obtained.

(Effects of the Invention) According to the present invention, (1) Since no solvent is used, there is no need to separate or generate prepolymers or polymers.

(2) Since expensive solvents are not used, polyarylates can be produced economically. (3) Since the polyarylate prepolymer is processed in a molten state throughout, the processing is simple and the processability is recommended. (4) Since it is a melt polymerization method, a polyarylate having the required degree of polymerization can be produced at a lower cost and in a shorter time than a solid phase polymerization method. Such.

Polyarylate having excellent physical properties as a heat-resistant polymer can be obtained economically and with good operability. In addition, the polyarylate obtained by the present invention is particularly useful in applications requiring heat resistance, such as films, fibers, and materials for molded products.

Patent applicant: Nippon Ester Co., Ltd., agent: Yu Kodama, 3 Procedural amendments (self-imposed, V. 1985, lb. 1, indication of the case, patent application No. 1982-257195, 2, name of the invention: Process for producing polyarylates 3) , Relationship with the case of the person making the amendment Patent applicant Address 4-1 Hinakita-cho, Okazaki City, Aichi Prefecture Name Shigeru Nakai, Representative Director of Nippon Ester Co., Ltd. 4, “Scope of Claims” and “Invention” in the agent specification Detailed explanation of
+a 6. Contents of amendment (1) Corrections are made as shown in the attached appendix to the scope of claims in Book i.

(2) r 3,684.766J on page 6, line 1 of the specification
Correct it as "3°684.761j J.

(3) Turn “2” in the second line from the bottom of page 9 of the same book to r 0. I.J.
I am corrected.

(4) Insert "net" next to "kneading kneader" in the first line from the bottom of page 9 of the same book.

(5) r (■), (rV) in the 3rd line of page 12 of the same book,
Correct (V)' J as r (IV), (V), (l J.

(6) r 2.5J on page 18, line 14 of the same book as r O,
Correct it to 6J.

(7) r 2i3j on page 20, line 7 of the same book as r 0.4
Correct it with J.

(8) r 3.1j on page 22, line 5 of the same book as r 1.2
Correct it with J.

Claims (1) At least one aromatic diol represented by the following general formula (I) and/or (■), at least one aromatic dicarboxylic acid, and an aliphatic anhydride carboxylic acid having 1 to 8 carbon atoms. A method for producing polyarylate, which comprises using a raw material as a raw material and melt-polymerizing it while kneading it under the conditions shown in formula 1 (III) using a screw-type kneading kneader to produce a polyarylate having an average degree of polymerization of 40 or more.

(In the formula, R+, Rz are hydrogen atoms, 1 to 20 carbon atoms
represents the same or different group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, and a ~rogen atom, and nl and R2 are each 1 to 4 m
R2 is an alkylene group having 1 to 8 carbon atoms, an alkylidene group having 1 to 8 full carbon atoms, 1 carbon atom
An arylene group having ~8 carbon atoms, a cycloalkylene group having up to 9 carbon atoms.

Cycloalkylidene group with up to 9 carbon atoms, OlS,
Represents a group selected from So, so, and CO.

R3 is 0 or 1. ) (RJni (wherein, Ra, R5I R& is a hydrogen atom, 1 carbon atom
It represents the same or different groups selected from a lower alkyl group having ~8 atoms and a halogen atom, R4°R5 are each an integer of 1 to 4, and R6 is an integer of 1 to 3. ) P/V≧0.1 (I[[) (where P is the required power for stirring of the screw-type kneader!9
KW), and ■ indicates the weight (kg) of the polymer. ) (2) The method for producing a polyarylate according to claim 1, wherein the aromatic diol represented by formula (1) is 2,2-bis(4-hydroxyphenyl)-propane.

(3) The aromatic diol represented by formula (1) is 4.4'-
A method for producing a polyarylate according to claim 1, which is (dihydroxyphenyl)-sulfone.

(4) The aromatic diol represented by formula (■) is 9.10-
A method for producing a polyarylate according to claim 1, which is dihydro-9-oxa-10-(2,5-dihydroxyphenyl)-phosphaphenanthrene-10-oxide.

(5) The method for producing a polyarylate according to any one of claims 1 to 4, wherein the aromatic dicarboxylic acid is isophthalic acid.

(6) The method for producing a polyarylate according to any one of claims 1 to 4, wherein the aliphatic carboxylic anhydride is acetic anhydride.

Claims (1)

[Scope of Claims] (1) At least one aromatic diol represented by the following general formula (I) and/or (II), at least one aromatic dicarboxylic acid, and anhydrous aliphatic carbon having 1 to 8 carbon atoms A method for producing polyarylate, which uses acid as a raw material and melt-polymerizes it while kneading it under the conditions shown by formula (II) using a screw-type kneading kneader to produce a polyarylate having an average degree of polymerization of 40 or more. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R_1 and R_2 are hydrogen atoms, carbon atoms 1 to 20
represents the same or different groups selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, and a halogen atom, and n^1 and n^2 are each 1 to 4. R_3 is an alkylene group having 1 to 8 carbon atoms, an alkylidene group having 1 to 8 carbon atoms, and 1 to 8 carbon atoms.
represents a group selected from an arylene group having 8 carbon atoms, a cycloalkylene group having 9 carbon atoms or less, a cycloalkylidene group having 9 carbon atoms or less, O, S, SO, SO_2 and CO, where n^3 is 0 or It is 1. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (In the formula, R_4, R_5, R_6 are the same or different groups selected from hydrogen atoms, lower alkyl groups having 1 to 8 carbon atoms, and halogen atoms) represents n^4, n^5
are each an integer of 1 to 4, and n^6 is an integer of 1 to 3. ) P/V≧2(III) (In the formula, P is the required stirring power of the screw type kneader (
IV), V indicates the weight (Kg) of the polymer. )(2)
The aromatic diol represented by formula (I) is 2,2-bis(
4-Hydroxyphenyl)-propane is the method for producing the polyarylate according to claim 1. (3) The aromatic diol represented by formula (I) is 4,4'
A method for producing a polyarylate according to claim 1, which is -(dihydroxyphenyl)-sulfone. (4) The aromatic diol represented by formula (II) is 9,10-
A method for producing a polyarylate according to claim 1, which is dihydro-9-oxa-10-(2,5-dihydroxyphenyl)-phosphaphenanthrene-10-oxide. (5) The method for producing a polyarylate according to any one of claims 1 to 4, wherein the aromatic dicarboxylic acid is isophthalic acid. (6) The method for producing a polyarylate according to any one of claims 1 to 4, wherein the aliphatic carboxylic anhydride is acetic anhydride.