# US 8,785,571 B2 · Method for producing polyarylene sulfide, and polyarylene sulfide

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- Number: US 8,785,571 B2
- Document ID: US8785571B2
- Status: Granted
- Kind: B2
- Application number: 13/882,411
- Filed: 2011-10-28
- Published: 2013-08-29
- Granted: 2014-07-22
- Earliest claimed: 2010-10-29
- Assignees: Toray Industries, Inc.
- Applicants: Akinori Kanomata; Shunsuke Horiuchi; Shu Kaiho; Koji Yamauchi
- Inventors: Akinori Kanomata; Shunsuke Horiuchi; Shu Kaiho; Koji Yamauchi
- Web page: https://patentgrep.com/patent/US8785571B2

## CPC

- C08G 75/14: Polysulfides
- C08G 75/02: Polythioethers
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A reactive functional group-containing polyarylene sulfide being narrow in dispersity and little in gas generation amount is produced by heating a cyclic polyarylene sulfide composition in the presence of 0.1 mol % to 25 mol %, per mol of arylene sulfide structural units, of a sulfide compound having a reactive functional group selected from among an amino group, a carboxyl group, a hydroxyl group, an acid anhydride group, an isocyanate group, an epoxy group, a silanol group, and an alkoxysilane group.

## Claims

### Claim 1

A method of producing a polyarylene sulfide (c) comprising heating a cyclic polyarylene sulfide composition (a) in the presence of 0.1 mol % to 25 mol %, per mol of arylene sulfide structural units, of a sulfide compound (b) having a reactive functional group represented by formula (A):
wherein at least one of Y and X is a functional group selected from the group consisting of an amino group, a carboxyl group, a hydroxyl group, an acid anhydride group, an isocyanate group, an epoxy group, a silanol group, and an alkoxysilane group, and n represents an integer of 0 to 20.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the cyclic polyarylene sulfide composition (a) comprises 50% by weight or more of a cyclic polyarylene sulfide represented by formula (B), and repetition number m in the formula is 4 to 50;
wherein Ar represents an arylene group.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the heating is performed under a condition containing no solvent.

### Claim 4 (depends on 1)

The method according to claim 1, wherein at least part of the heating is performed under a reduced pressure condition.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the heating temperature is equal to or higher than the melting temperature of a reaction mixture composed of the cyclic polyarylene sulfide composition (a) and the sulfide compound (b) having a reactive functional group.

### Claim 6 (depends on 1)

The method according to claim 1, wherein an amount of the reactive functional groups introduced per mol of the arylene sulfide structural units of the resulting polyarylene sulfide (c) is 0.01 to 5 mol %.

### Claim 7 (depends on 1)

The method according to claim 1, wherein a dispersity represented by weight average molecular weight/number average molecular weight of the resulting polyarylene sulfide (c) is 2.5 or less.

### Claim 8 (depends on 1)

The method according to claim 1, wherein alkali metal content of the resulting polyarylene sulfide (c) is 500 ppm or less.

### Claim 9 (depends on 1)

The method according to claim 1, wherein the resulting polyarylene sulfide (c) has a weight loss ratio at 100 to 330° C. of 0.2% by weight or less when thermogravimetric analysis is performed from 50° C. to 340° C. at a temperature ramp-up rate of 20° C./min under a non-oxidative atmosphere of normal pressure.

### Claim 10 (depends on 1)

The method according to claim 1, wherein the reactive functional group contained in the sulfide compound (b) having a reactive functional group is a group selected the group consisting of an amino group, a carboxyl group, and a hydroxyl group.

### Claim 11 (depends on 1)

The method according to claim 1, wherein the sulfide compound (b) having a reactive functional group is one or more members selected from the group consisting of bis(4-aminophenyl) sulfide, bis(4-carboxyphenyl) sulfide, bis(4-hydroxyphenyl) sulfide, and oligomers thereof.

### Claim 12 (depends on 1)

A method of producing a polyarylene sulfide composition (c′) further comprising adding a reactive compound (d) to a polyarylene sulfide (c) obtained by the method according to claim 1.

### Claim 13 (depends on 12)

The method according to claim 12, wherein the reactive compound (d) is a silane coupling agent having a group selected from the group consisting of an epoxy group, an amino group, and an isocyanate group and an added amount thereof is 0.01 to 5 parts by weight per 100 parts by weight of the polyarylene sulfide (c).

### Claim 14 (depends on 12)

The method according to claim 12, wherein a thickening ratio of the polyarylene sulfide composition (c′) after adding the reactive compound (d) to the polyarylene sulfide (c) before adding the reactive compound (d) is 1.01 or more.