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Method for producing acid radical-containing polyarylene sulfide resin

一种制造方法、聚芳硫醚的技术，应用在高效率的制造领域，能够解决相容性或密着性的改善效果不充分、分子量低、无法羧基导入等问题

Active Publication Date: 2009-08-05
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this technique, the reactivity of dichlorobenzoic acid itself is low and the molecular weight is low. In addition, unreacted dichlorobenzoic acid remains in the reaction product, and the improvement of the compatibility or adhesion The effect is not sufficient, and carboxyl groups cannot be introduced into arbitrary positions substantially
[0006] As mentioned above, conventionally, when attempting to introduce acid groups represented by carboxyl groups into the resin structure of PAS resins, there were problems in that the molecular weight decreased, and the reactivity of carboxyl group-containing compounds was low, so that they could not be sufficiently introduced into the PAS resin structure.
In addition, the current situation is that there are large design constraints when introducing acid groups into the polymer structure, and it is impossible to introduce acid groups at arbitrary positions in the polymer structure according to the purpose and application.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] (Dehydration process: production process of anhydrous sodium sulfide composition)

[0108] In a 1-liter autoclave connected with a pressure gauge, a thermometer, a condenser, a decanter and a zirconium-lined stirring wing, add 220.5 g (1.5 moles) of p-dichlorobenzene (hereinafter abbreviated as p-DCB), 29.7 g (0.3 mol) of NMP, 123.6 g (1.5 mol) of 68 mass % NaSH aqueous solution melted by heating, and 125.0 g (1.5 mol) of 48 mass % NaOH aqueous solution were then stirred under a nitrogen atmosphere at 2 After hours, the temperature was raised to 173° C., and after 123.5 g of water was distilled off, the kettle was sealed. At this time, the DCB distilled off by azeotropy was separated by a decanter and returned to the tank at any time. After the dehydration is completed, the interior of the kettle is in a state where the microparticle-like anhydrous sodium sulfide composition is dispersed in DCB.

[0109] (polymerization process: manufacturing process of PPS)

[0110]...

Embodiment 2

[0114] In the polymerization step, the same operation as in Example 1 was performed except that 0.91 g (0.0045 mol) of 4-chloro-3-nitrobenzoic acid was used instead of 2,4-dichlorobenzoic acid. 156 g of PPS were obtained as a white powder. The melt viscosity of this polymer was 173 Pa·s. The melt viscosity (η') of the composition of this polymer and 3-glycidoxypropyltrimethoxysilane was 805 Pa·s, and the degree of viscosity increase was 4.7 times.

Embodiment 3

[0115] Example 3 (4-dichlorobenzoic acid is introduced into a carboxyl group at the end of the molecule according to the post-addition method)

[0116] In the polymerization process, the same operation as in Example 1 was performed except that 0.86 g (0.0045 mol) of 2,4-dichlorobenzoic acid was heated up to 250° C. and then used in 1 hour. 154 g of PPS were obtained as white powder. The melt viscosity of this polymer was 176 Pa·s. The melt viscosity (η') of the composition of this polymer and 3-glycidoxypropyltrimethoxysilane was 940 Pa·s, and the degree of viscosity increase was 5.3 times. When 1-chloronaphthalene was added to this composition at 0.1% by mass at 285° C., it was completely dissolved, showing that the molecular weight was increased linearly.

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PUM

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Abstract

Disclosed is a method for producing an acid radical-containing PAS resin which enables to substantially completely react an acid radical-containing compound without lowering the molecular weight of the PAS resin. This method for producing an acid radical-containing PAS resin enables to efficiently introduce an acid radical into the PAS resin structure, and also enables to introduce an acid radical into a desired position in the PAS resin structure. Specifically disclosed is a method for producing a polyarylene sulfide resin, which comprises the step 1 and the step 2 described below as indispensable production steps. Step 1: A step wherein a hydrated alkali metal sulfide; or a hydrated alkali metal hydrosulfide and an alkali metal hydroxide; and an aliphatic cyclic compound (c1) which can be ring-opened by hydrolysis; and a non-hydrolyzable organic solvent; are reacted while being dehydrated for producing a slurry (I). Step 2: A step wherein a polyhaloaromatic compound (a); the alkali metal hydrosulfide (b); an alkali metal salt (c2) of a hydrolysis product of the compound (c1); and an aromatic compound (d) having a leaving group and an acid radical in a nucleophilic reaction; are reacted for polymerization in the slurry (I).

Description

technical field [0001] The present invention relates to a high-efficiency production method of acid group-containing high-molecular-weight polyarylene sulfide resin. Background technique [0002] Polyarylene sulfide resin (hereinafter abbreviated as "PAS resin") represented by polyphenylene sulfide resin (hereinafter abbreviated as "PPS resin") is excellent in heat resistance, chemical resistance, etc. Widely used in electrical and electronic parts, automobile parts, water heater parts, fibers, and film applications. This PAS resin usually has defects such as low molecular weight, insufficient impact strength of parts obtained by molding this PAS resin, and becoming very brittle. In addition, compatibility with other resins or compatibility with other parts when molding products Adhesion is poor. [0003] Therefore, the method for improving the impact strength of this PAS resin is known as the following technology: selectively introducing reactive functional groups such as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/02C08G75/0213
CPCC08G75/0213C08G75/0259C08G75/02C08G75/04C08G75/14
Inventor 桧森俊男山内畅彦古泽高志
Owner DIC CORP
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