Polyarylene sulfide resin and manufacturing method therefor, poly(arylene sulfonium salt) and manufacturing method therefor, and sulfoxide

Patent metadata

Field	Value
Publication number	US-9657142-B2
Application number	US-201414915974-A
Country	US
Kind code	B2
Filing date	Sep 2, 2014
Priority date	Sep 3, 2013
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

The present invention relates to a method for manufacturing a polyarylene sulfide resin comprising: reacting a sulfoxide represented by the following formula (1) with a particular aromatic compound to obtain a poly(arylenesulfonium salt) having a particular constitutional unit; and dealkylating or dearylating the poly(arylenesulfonium salt) to obtain a polyarylene sulfide resin having a particular constitutional unit,

wherein R 1 represents an alkyl group having 1 to 10 carbon atoms, etc.; Ar 1 and Ar 2 each independently represent an arylene group optionally having a substituent; and Z represents a direct bond, etc.

First claim

The invention claimed is:

1. A method for manufacturing a polyarylene sulfide resin comprising:
reacting a sulfoxide represented by the following formula (1) with an aromatic compound represented by the following formula (2) to obtain a poly(arylenesulfonium salt) having a constitutional unit represented by the following formula (10); and
dealkylating or dearylating the poly(arylenesulfonium salt) to obtain a polyarylene sulfide resin having a constitutional unit represented by the following formula (20):

wherein in formula (1), (2), (10) or (20),
R 1 represents an alkyl group having 1 to 10 carbon atoms or an aryl group optionally having an alkyl group having 1 to 10 carbon atoms;
R 2a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, —Ar 4 , —S—Ar 4 , —O—Ar 4 , —CO—Ar 4 , —SO 2 —Ar 4 or —C(CF 3 ) 2 —Ar 4 ;
R 2b represents a direct bond, —Ar 6 —, —S—Ar 6 —, —O—Ar 6 —, —CO—Ar 6 —, —SO 2 —Ar 6 — or —C(CF 3 ) 2 —Ar 6 —;
Ar 1 , Ar 2 , Ar 3b and Ar 6 each independently represent an arylene group optionally having a substituent;
Ar 3a and Ar 4 each independently represent an aryl group optionally having a substituent;
Z represents a direct bond, —S—, —O—, —CO—, —SO 2 — or —C(CF 3 ) 2 —; and
X − represents an anion.

2. A method for manufacturing a poly(arylenesulfonium salt) comprising:
reacting a sulfoxide represented by the following formula (1) with an aromatic compound represented by the following formula (2) to obtain a poly(arylenesulfonium salt) having a constitutional unit represented by the following formula (10):

wherein in formula (1), (2) or (10),
R 1 represents an alkyl group having 1 to 10 carbon atoms or an aryl group optionally having an alkyl group having 1 to 10 carbon atoms;
R 2a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, —Ar 4 , —S—Ar 4 , —O—Ar 4 , —CO—Ar 4 , —SO 2 —Ar 4 or —C(CF 3 ) 2 —Ar 4 ;
R 2b represents a direct bond, —Ar 6 —, —S—Ar 6 —, —O—Ar 6 —, —CO—Ar 6 —, —SO 2 —Ar 6 — or —C(CF 3 ) 2 —Ar 6 —;
Ar 1 , Ar 2 , Ar 3b and Ar 6 each independently represent an arylene group optionally having a substituent;
Ar 3a and Ar 4 each independently represent an aryl group optionally having a substituent;
Z represents a direct bond, —S—, —O—, —CO—, —SO 2 — or —C(CF 3 ) 2 —; and
X − represents an anion.

Assignees

• Dainippon Ink & Chemicals
• Nat Univ Corp Iwate Univ

Inventors

• Watanabe Hajime
• Furusawa Takashi
• Ogawa Satoshi
• Takata Toshikazu

Classifications

• C07C323/65

  containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton · CPC title

• C08G75/0286

  Chemical after-treatment · CPC title

• C08G75/12

  Polythioether-ethers (C08G75/0245 takes precedence) · CPC title

• C07C321/30

  Sulfides having the sulfur atom of at least one thio group bound to two carbon atoms of six-membered aromatic rings · CPC title

• C07C317/22 Primary

  with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title