Polyphenylene sulfide block copolymer and manufacturing method therefor

Patent metadata

Field	Value
Publication number	US-9840596-B2
Application number	US-201515129873-A
Country	US
Kind code	B2
Filing date	Mar 24, 2015
Priority date	Mar 31, 2014
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

A polyphenylene sulfide block copolymer contains polyphenylene sulfide units and polyorganosiloxane units and has a glass-transition temperature in the range of 80° C. or lower and a weight-average molecular weight in the range of 35,000 to 100,000. The polyphenylene sulfide block copolymer has high flexibility as well as high heat resistance and heat aging resistance.

First claim

The invention claimed is:

1. A polyphenylene sulfide block copolymer comprising:
50 to 99% by weight of polyphenylene sulfide units (A); and
50 to 1% by weight of polyorganosiloxane units (B),
provided that the total amount of (A) and (B) is 100% by weight, the polyphenylene sulfide block copolymer having a glass-transition temperature of 80° C. or lower and a weight-average molecular weight of 35,000 to 100,000.

2. The polyphenylene sulfide block copolymer according to claim 1 , wherein the polyorganosiloxane units (B) are polydimethylsiloxane units.

3. The polyphenylene sulfide block copolymer according to claim 1 , wherein the polyorganosiloxane units (B) are contained in an amount of 10 to 40% by weight.

4. The polyphenylene sulfide block copolymer according to claim 1 , wherein the polyphenylene sulfide block copolymer has a weight-average molecular weight of 45,000 to 80,000.

5. A method of producing the polyphenylene sulfide block copolymer according to claim 1 , comprising:
heating a polyphenylene sulfide (A) having a functional group content of 100 μmol/g or more and a polyorganosiloxane (B) having functional groups,
the polyphenylene sulfide (A) being represented by general formula (I):

wherein Z is a reactive functional group selected from a carboxyl group, an amino group, a hydroxyl group, an acid anhydride group, an isocyanate group, an epoxy group, a silanol group, an alkoxysilane group, and derivatives thereof, and m is an integer of 10 or greater.

6. The method according to claim 5 , wherein heating the polyphenylene sulfide (A) and the polyorganosiloxane (B) is carried out in an organic polar solvent.

7. The method according to claim 5 , wherein the polyorganosiloxane (B) having functional groups has, at its ends, reactive functional groups selected from an epoxy group, a carboxyl group, an amino group, a hydroxyl group, an acid anhydride group, an isocyanate group, a silanol group, an alkoxysilane group, and derivatives thereof.

8. The method according to claim 5 , wherein the polyphenylene sulfide (A) having a functional group content of 100 μmol/g or more is a polyphenylene sulfide obtained by heating a mixture comprising at least (i) a sulfidizing agent, (ii) a dihalogenated aromatic compound, (iii) an organic polar solvent, and (iv) a monohalogenated compound having a reactive functional group W, the amount of the monohalogenated compound being 0.01 to 25 mol % per mole of the dihalogenated aromatic compound (ii), the monohalogenated compound being represented by general formula (II):

wherein V represents a halogen.

9. The method according to claim 8 , wherein the reactive functional group of the monohalogenated compound (iv) having a reactive functional group W is a functional group selected from a carboxyl group, an amino group, a hydroxyl group, an acid anhydride group, an isocyanate group, an epoxy group, a silanol group, an alkoxysilane group, and derivatives thereof.

10. The method according to claim 5 , wherein the polyphenylene sulfide (A) is a polyphenylene sulfide obtained by heating a cyclic polyphenylene sulfide (a) in the presence of a sulfide compound having reactive functional groups, the amount of the sulfide compound being 0.01 mol % to 25 mol % per mole of phenylene sulfide structural units, the sulfide compound being represented by general formula (III):

wherein at least one of X and Y is a functional group selected from a carboxyl group, an amino group, a hydroxyl group, an acid anhydride group, an isocyanate group, an epoxy group, a silanol group, an alkoxysilane group, and derivatives thereof, and p represents an integer of 0 to 20, provided that p may be a single integer or a combination of different integers.

11. The method according to claim 10 , wherein the cyclic polyphenylene sulfide (a) is a monomer or a mixture comprising 50% by weight or more of a cyclic polyphenylene sulfide represented by general formula (IV) wherein i is from 4 to 50:

12. The method according to claim 10 , wherein the polyphenylene sulfide (A) is a polyphenylene sulfide obtained by heating a mixture comprising the cyclic polyphenylene sulfide (a) and the sulfide compound having reactive functional groups in the absence of a solvent.

13. The method according to claim 10 , wherein the reactive functional groups of the sulfide compound having reactive functional groups are functional groups selected from an amino group, a carboxyl group, and a hydroxyl group.

14. A molded article comprising the polyphenylene sulfide block copolymer according to claim 1 .

Assignees

• Toray Industries
• Toray Industries

Inventors

• Yamanaka Yuji
• Isago Hiroyuki
• Saito Kei
• Matsumoto Hideki

Classifications

• C08G77/42

  Block-or graft-polymers containing polysiloxane sequences (polymerising aliphatic unsaturated monomers on to a polysiloxane C08F283/12) · CPC title

• C08G65/02

  from cyclic ethers by opening of the heterocyclic ring · CPC title

• C08G81/00 Primary

  Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers (involving only carbon-to-carbon unsaturated bond reactions C08F299/00 {; polyester-amides C08G69/44; polyester-imides C08G73/16; polyamides-imides C08G73/14; block- or graft polymers containing polysiloxane sequences C08G77/42}) · CPC title

• C08G77/06

  Preparatory processes · CPC title

• C08G75/025

  Preparatory processes · CPC title