Polyarylene sulfide production method and polyarylene sulfide

Patent metadata

Field	Value
Publication number	US-10647818-B2
Application number	US-201515529354-A
Country	US
Kind code	B2
Filing date	Dec 18, 2015
Priority date	Jan 9, 2015
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

A method of producing a polyarylene sulfide (PAS) includes a preparation step of preparing a charged mixture containing an organic amide solvent, a sulfur source, water, and a dihalo aromatic compound; a first-stage polymerization step of performing a polymerization reaction on the charged mixture at a temperature of from 170 to 280° C. to produce a prepolymer having a conversion ratio of the dihalo aromatic compound of 50% or greater; and a second-stage polymerization step of continuing the polymerization reaction in a phase-separated state at a temperature of from 245 to 290° C. in a reaction system containing the prepolymer, and includes adding a polyfunctional compound to the reaction system in the phase-separated state. A PAS having a melt viscosity (310° C., shear rate: 1216 sec −1 ) of from 0.1 to 8000 Pa·s is produced by the method.

First claim

The invention claimed is:

1. A method of producing a polyarylene sulfide comprising:
(1) a preparation step of preparing a charged mixture containing an organic amide solvent, a sulfur source, water, an alkali metal hydroxide, and a dihalo aromatic compound;
(2) a first-stage polymerization step of performing a polymerization reaction on the charged mixture at a temperature of from 170 to 280° C. to produce a prepolymer having a conversion ratio of the dihalo aromatic compound of 50% or greater; and
(3) a second-stage polymerization step of continuing the polymerization reaction in a phase-separated state at a temperature of from 245 to 290° C. in a reaction system containing the prepolymer,
the method including adding a polyfunctional compound to the reaction system in the phase-separated state after the temperature reaches 245 to 290° C., and after a phase separation agent is added to the reaction system in the second-stage polymerization.

2. The method of producing a polyarylene sulfide according to claim 1 , wherein the sulfur source contains one or both of an alkali metal sulfide and an alkali metal hydrosulfide.

3. The method of producing a polyarylene sulfide according to claim 1 , further comprising a dehydration step of heating a mixture containing an organic amide solvent, a sulfur source, and an alkali metal hydroxide to discharge at least a part of distillate containing water from a system containing the mixture to the outside of the system before the preparation step.

4. The method of producing a polyarylene sulfide according to claim 1 , wherein, in the preparation step, the charged mixture containing the dihalo aromatic compound in an amount of from 0.95 to 1.2 mol per mole of the sulfur source is prepared.

5. The method of producing a polyarylene sulfide according to claim 1 , wherein, in the preparation step, the charged mixture containing water in an amount of from 0.5 to 2 mol per mole of the sulfur source is prepared.

6. The method of producing a polyarylene sulfide according to claim 1 , wherein, in the preparation step, the charged mixture containing the alkali metal hydroxide in an amount of from 0.95 to 1.09 mol per mole of the sulfur source is prepared.

7. The method of producing a polyarylene sulfide according to claim 1 , wherein the polyfunctional compound is added in an amount of from 0.01 to 2 mol per 100 mol of the sulfur source.

8. The method of producing a polyarylene sulfide according to claim 1 , wherein the polyfunctional compound has at least one functional group selected from the group consisting of a halogen group, a thiol group, a carboxyl group, and derivatives thereof.

9. The method of producing a polyarylene sulfide according to claim 1 , wherein the polyfunctional compound is at least one selected from the group consisting of a polyhaloaromatic compound, an aromatic thiol compound, an aromatic carboxylic acid, and derivatives thereof.

10. The method of producing a polyarylene sulfide according to claim 1 , wherein a phase separation agent is at least one selected from the group consisting of an organic carboxylic acid metal salt, an organic sulfonic acid metal salt, an alkali metal halide, an alkaline earth metal halide, an alkaline earth metal salt of aromatic carboxylic acid, a phosphoric acid alkali metal salt, an alcohol, a paraffin hydrocarbon, and water.

11. The method of producing a polyarylene sulfide according to claim 1 , wherein a proportion of a byproduct in an ultra fine powder form having a size of 100 mesh-on is 85% or greater and a proportion of a byproduct in an ultra fine powder form having a size of 400 mesh-pass is 7% or less.

12. The method of producing a polyarylene sulfide according to claim 1 further comprising:
(4) a recovery step of recovering the polyarylene sulfide by sieving a reaction solution through a 100-mesh screen after the second stage polymerization step, the polyarylene sulfide in a dry state having a melt viscosity of 0.1 to 33 Pa·s measured at a temperature of 310° C. and a shear rate of 1,216 sec −1 .

Assignees

• Kureha Corp

Inventors

• Konno Akihiro
• Takaki Ken-Ichi
• Yoshida Yui
• Sato Hiroyuki

Classifications

• C08G75/0263 Primary

  using elemental sulfur · CPC title

• C08G75/02

  Polythioethers · CPC title

• C08G75/0259

  metal hydrogensulfides · CPC title

• C08G75/0254

  using metal sulfides · CPC title

• C08G75/025

  Preparatory processes · CPC title