Polyarylene sulfide, and purification method and production method therefor

Patent metadata

Field	Value
Publication number	US-12522697-B2
Application number	US-202017776113-A
Country	US
Kind code	B2
Filing date	Dec 10, 2020
Priority date	Dec 11, 2019
Publication date	Jan 13, 2026
Grant date	Jan 13, 2026

Abstract

Provided are a purification method for a polyarylene sulfide (PAS) that can efficiently reduce the amount of a carboxyalkylamino group-containing compound in the PAS by treating the carboxyalkylamino group-containing compound in the PAS under a low pressure without using a strong acid, and a production method for a PAS having a reduced amount of the carboxyalkylamino group-containing compound in the PAS. The purification method for a PAS includes: a step of obtaining a crude PAS-containing mixture by removing a solvent from a crude reaction product containing the PAS obtained by reacting a polyhalo aromatic compound with a sulfidizing agent in an organic polar solvent; a step of bringing the crude PAS mixture into contact with water and an oxygen atom-containing solvent to convert the crude PAS into porous particles; and a step of bringing the obtained porous particles into contact with carbonated water.

First claim

The invention claimed is:

1 . A purification method for a polyarylene sulfide, comprising:
a step (1) of obtaining a mixture containing a crude polyarylene sulfide by removing a solvent from a crude reaction product containing a polyarylene sulfide obtained by reacting a polyhalo aromatic compound with a sulfidizing agent in an organic polar solvent; a step (2) of purifying the mixture containing the crude polyarylene sulfide to convert the crude polyarylene sulfide into porous particles having a specific surface area in a range of 30 [m 2 /g] or more; and a step (3) of bringing the obtained polyarylene sulfide porous particles into contact with carbonated water, wherein the step (2) includes a step of performing a step (2Ss) of bringing the mixture containing the crude polyarylene sulfide into contact with an oxygen atom-containing solvent having 1 to 3 carbon atoms and a step (2Sw) of bringing the mixture containing the crude polyarylene sulfide into contact with water each for at least once, and a ratio of a compound (1) represented by the following structural formula (1) contained in the porous particles after the step (3) is in a range of 1100 [ppm] to 3000 [ppm] or less,

in the formula, Ar represents an aryl group having a halogen atom, R 1 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a cyclohexyl group, R 2 represents an alkylene group having 3 to 5 carbon atoms, and X represents a hydrogen atom or an alkali metal atom.

2 . The purification method according to claim 1 , wherein
in the step (2), the oxygen atom-containing solvent having 1 to 3 carbon atoms is an aqueous solution.

3 . The purification method according to claim 2 , wherein
the oxygen atom-containing solvent having 1 to 3 carbon atoms has a concentration in the aqueous solution in a range of 90 parts by mass or less with respect to 100 parts by mass of the aqueous solution.

4 . The purification method according to claim 1 , wherein
in the step (3), the polyarylene sulfide porous particles and the carbonated water are brought into contact with each other under a pressure smaller than 0.1 MPa.

5 . The purification method according to claim 1 , wherein
in the step (3), the polyarylene sulfide porous particles and the carbonated water are brought into contact with each other at a temperature of 60° C. or lower.

6 . A production method for a polyarylene sulfide, comprising:
a step of purifying a polyarylene sulfide by the purification method according to claim 1 .

7 . The production method for a polyarylene sulfide according to claim 6 , wherein
the purified polyarylene sulfide is porous particles having a specific surface area in a range of 10 [m 2 /g] or more.

8 . The production method for a polyarylene sulfide according to claim 6 , wherein
the purified polyarylene sulfide has a ratio of a content of a compound (1) represented by the following structural formula (1) in a range of more than 1000 [ppm] to 3000 [ppm] or less,

in the formula, Ar represents an aryl group having a halogen atom, R 1 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a cyclohexyl group, R 2 represents an alkylene group having 3 to 5 carbon atoms, and X represents a hydrogen atom or an alkali metal atom.

9 . The production method for a polyarylene sulfide according to claim 6 , wherein
the purified polyarylene sulfide has an isothermal crystal acceleration in a range of 4 minutes or longer and 9 minutes or shorter (here, a measured value when the purified polyarylene sulfide is melted at 350° C./3 min, then rapidly cooled (210° C./min) from 350° C. to 240° C., and held at a cooled temperature (240° C.) for 15 minutes using a differential scanning calorimeter).

10 . The purification method according to claim 2 , wherein
in the step (3), the polyarylene sulfide porous particles and the carbonated water are brought into contact with each other under a pressure smaller than 0.1 MPa.

11 . The purification method according to claim 3 , wherein
in the step (3), the polyarylene sulfide porous particles and the carbonated water are brought into contact with each other under a pressure smaller than 0.1 MPa.

12 . The purification method according to claim 2 , wherein
in the step (3), the polyarylene sulfide porous particles and the carbonated water are brought into contact with each other at a temperature of 60° C. or lower.

13 . The purification method according to claim 3 , wherein
in the step (3), the polyarylene sulfide porous particles and the carbonated water are brought into contact with each other at a temperature of 60° C. or lower.

14 . The purification method according to claim 4 , wherein
in the step (3), the polyarylene sulfide porous particles and the carbonated water are brought into contact with each other at a temperature of 60° C. or lower.

15 . A production method for a polyarylene sulfide, comprising:
a step of purifying a polyarylene sulfide by the purification method according to claim 2 .

16 . A production method for a polyarylene sulfide, comprising:
a step of purifying a polyarylene sulfide by the purification method according to claim 3 .

17 . A production method for a polyarylene sulfide, comprising:
a step of purifying a polyarylene sulfide by the purification method according to claim 4 .

18 . A production method for a polyarylene sulfide, comprising:
a step of purifying a polyarylene sulfide by the purification method according to claim 5 .

Assignees

• Dainippon Ink & Chemicals

Inventors

• Ibaraki Taku
• Inoue Satoshi
• Watanabe Hideki
• Furusawa Takashi

Classifications

• C08G75/0281 Primary

  Recovery or purification · CPC title

• C08G75/0259 Primary

  metal hydrogensulfides · CPC title