Copolymer of diallylamines and sulfur dioxide, and method for producing same

Patent metadata

Field	Value
Publication number	US-10442895-B2
Application number	US-201615740099-A
Country	US
Kind code	B2
Filing date	Oct 7, 2016
Priority date	Oct 15, 2015
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

Abstract

Provided are a copolymer of diallylamines and sulfur dioxide having a high molecular weight and a low content amount of impurities such as halogens, and a production method with which it is possible to produce such a copolymer relatively simply and at low cost. This problem is solved by: a copolymer having a weight-average molecular weight of 150,000 or higher obtained by GPC measurement and a degree of polymerization of 1000 or higher, the copolymer being obtained by copolymerizing sulfur dioxide and a sulfonate or alkyl sulfate salt of diallylamines having a specific structure; and a method for producing a copolymer, the method having a step for copolymerizing sulfur dioxide and a sulfonate or alkyl sulfate salt of diallylamines having a specific structure in ethylene glycol or in propylene glycol monomethyl ether.

First claim

The invention claimed is:

1. A copolymer having a weight average molecular weight of 235,743 or more and a degree of polymerization of 1,000 or more determined by GPC measurement, and obtained by copolymerizing a sulfonic acid salt or alkylsulfate salt of a diallylamine represented by Structural Formula 1, wherein R 1 and R 2 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms and X-is a sulfonic acid ion having 1 to 3 carbon atoms or an alkylsulfate ion having 1 to 3 carbon atoms, and sulfur dioxide represented by Structural Formula 2

2. The copolymer according to claim 1 , wherein the proportion of the constitutional units derived from the sulfonic acid salt or alkylsulfate salt of a diallylamine and the constitutional units derived from sulfur dioxide to all of the constitutional units of the copolymer is 90 mol % or more.

3. The copolymer according to claim 1 , wherein the ratio of the number of the constitutional units derived from the sulfonic acid salt or alkylsulfate salt of a diallylamine to the number of the constitutional units derived from the sulfur dioxide is from 07:1 to 1.3:1.

4. The copolymer according to claim 1 , obtained by copolymerizing the sulfonic acid salt or alkylsulfate salt of a diallylamine with the sulfur dioxide in ethylene glycol or propylene glycol monomethyl ether.

5. The copolymer according to claim 4 , obtained in the form of a solution or a dispersion by performing polymerization in ethylene glycol or propylene glycol monomethyl ether.

6. The copolymer according to claim 1 , obtained by copolymerizing the sulfonic acid salt or alkylsulfate salt of a diallylamine and the sulfur dioxide using a radical initiator that substantially does not start a redox reaction with sulfur dioxide at temperatures of from 0° C. to 100° C.

7. The copolymer according to claim 6 , wherein the radical initiator is an aliphatic azo compound.

8. A copolymer having a weight average molecular weight of 235,743 or more and a degree of polymerization of 1,000 or more determined by GPC measurement, and being a reaction product of a sulfonic acid salt or alkylsulfate salt of a diallylamine represented by Structural Formula 1, wherein R 1 and R 2 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms and X-is a sulfonic acid ion having 1 to 3 carbon atoms or an alkylsulfate ion having 1 to 3 carbon atoms, and sulfur dioxide represented by Structural Formula 2

9. The copolymer according to claim 8 , wherein the proportion of theconstitutional units derived from the sulfonic acid salt or alkylsulfate salt of a diallylamine and the constitutional units derived from the sulfur dioxide to all of the constitutional units of the copolymer is 90 mol % or more.

10. The copolymer according to claim 8 , wherein the ratio of the number of the constitutional units derived from the sulfonic acid salt or alkylsulfate salt of a diallylamine to the number of the constitutional units derived from the sulfur dioxide is from 0,7:1 to 1.3:1.

11. A paint, a stain, or an electrophotographic toner comprising the copolymer according to claim 1 .

12. A paint, a stain, or an electrophotographic toner comprising the copolymer according to claim 8 .

Assignees

• Nitto Boseki Co Ltd

Inventors

• Yamada Nobuyuki
• Bunya Masaru

Classifications

• C08F36/20

  unconjugated · CPC title

• C08K5/23

  Azo-compounds · CPC title

• C08G75/22 Primary

  Copolymers of sulfur dioxide with unsaturated aliphatic compounds · CPC title

• C09D181/06

  Polysulfones; Polyethersulfones · CPC title

• C09D11/106

  containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title