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

Patent metadata

Field	Value
Publication number	US-2016200874-A1
Application number	US-201414915974-A
Country	US
Kind code	A1
Filing date	Sep 2, 2014
Priority date	Sep 3, 2013
Publication date	Jul 14, 2016
Grant date	—

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

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 polyarylene sulfide resin having a constitutional unit represented by the following formula (20):
S—Ar 1 —Z—Ar 2 —S—Ar 3b —R 2b   (20)
wherein 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 , A 2 , Ar 3b and Ar 6 each independently represent an arylene group optionally having a substituent; Z represents a direct bond, —S—, —O—, —CO—, —SO 2 — or —C(CF 3 ) 2 —; wherein Z is a direct bond, —CO—, —SO 2 — or —C(CF 3 ) 2 — when Ar 1 , Ar 2 and Ar 3b are each a 1,4-phenylene group and R 2b is a direct bond; and Z is —S—, —O—, —CO—, —SO 2 — or —C(CF 3 ) 2 — when Ar 1 , Ar 2 and Ar 3b are each a 1,4-phenylene group, R 2b is —Ar 6 — and Ar 6 is a 1,4-phenylene group.

3 . 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.

4 . A poly(arylenesulfonium salt) having a constitutional unit represented by the following formula (10):

wherein
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 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;
Z represents a direct bond, —S—, —O—, —CO—, —SO 2 — or —C(CF 3 ) 2 —; and
X − represents an anion, wherein
Z is a direct bond, —CO—, —SO 2 — or —C(CF 3 ) 2 — when Ar 1 , Ar 2 and Ar 3b are each a 1,4-phenylene group and R 2b is a direct bond; and
Z is —S—, —O—, —CO—, —SO 2 — or —C(CF 3 ) 2 — when Ar 1 , Ar 2 and Ar 3b are each a 1,4-phenylene group, R 2b is —Ar 6 — and Ar 6 is a 1,4-phenylene group.

5 . A sulfoxide represented by the following formula (5):

wherein
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;
Ar 1 and Ar 2 each independently represent an arylene group optionally having a substituent; and
represents a direct bond, —S—, —O—, —CO—, —SO 2 — or —C(CF 3 ) 2 —, wherein
R 1 is an alkyl group having 2 to 10 carbon atoms or an aryl group optionally having an alkyl group having 2 to 10 carbon atoms when Z is —S—.

Assignees

• Dainippon Ink & Chemicals
• Nat University Corp Iwate University

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

• C08G75/0272 Primary

  using other sulfur sources · CPC title

• C08G75/12

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

• C08G75/14 Primary

  Polysulfides · CPC title

• C08G75/0286

  Chemical after-treatment · CPC title