Polymeric aminoacrylates

Patent metadata

Field	Value
Publication number	US-11161925-B2
Application number	US-201615777473-A
Country	US
Kind code	B2
Filing date	Nov 29, 2016
Priority date	Dec 2, 2015
Publication date	Nov 2, 2021
Grant date	Nov 2, 2021

Abstract

Described herein are polymeric aminoacrylates formed by the reaction of polyalkylene glycol diacrylates with bireactive amines. The polymeric aminoacrylate are comprised of moieties of poly(alkylene glycol) diacrylate and moieties of bireactive amines. Also described herein are energy curable ink and coating compositions that include the described polymeric aminoacrylates. The energy curable ink and coating compositions that include the described polymeric aminoacrylates are well-suited for use in packaging applications where low migration of uncured monomer material after cure is desired, such as in the packaging of foodstuffs, pharmaceuticals, etc.

First claim

What is claimed is:

1. A polymeric aminoacrylate comprising moieties of poly(alkylene glycol) diacrylate and moieties of bireactive amine, wherein poly(alkylene oxide) cores of the poly(alkylene glycol) diacrylate moieties have the formula: (C n H 2n O) x , where n is from 1 to 6 and x is from 2 to 50, and wherein the bireactive amine moieties are selected from primary alkyl amines, primary alkanolamines, primary alkoxyamines, primary alkylamines substituted with tertiary amine, primary alkylamines substituted with aryl, heterocyclic amines having two secondary amine groups, and combinations thereof.

2. The polymeric aminoacrylate of claim 1 , wherein the poly(alkylene glycol) diacrylate moieties are poly(ethylene glycol) diacrylate moieties.

3. The polymeric aminoacrylate of claim 1 , wherein the poly(alkylene glycol) diacrylate moieties are poly(propylene glycol) diacrylate moieties.

4. The polymeric aminoacrylate of claim 1 , wherein the poly(alkylene glycol) diacrylate moieties are copolymers of poly(ethylene glycol) diacrylate and poly(propylene glycol) diacrylate.

5. The polymeric aminoacrylate of claim 1 , further comprising one or more additional moieties selected from diacrylate moieties, triacrylate moieties, and tetraacrylate moieties.

6. The polymeric aminoacrylate of claim 1 , wherein the bireactive amine moieties are derived from primary amines, amines having two secondary amine groups, and combinations thereof.

7. The polymeric aminoacrylate of claim 3 , wherein the bireactive amine moieties are selected from ethylamine, propylamine, isopropylamine, butylamine, isobutyl amine, hexylamine, octylamine, 2-ethylhexylamine, cyclopentylamine, cyclohexylamine, benzyl amine, 2-ethoxyethylamine, 3-ethoxypropylamine, ethanolamine, propanol amine, butanolamine, 2-dimethylaminoethylamine, 2-diethylaminoethylamine, 3-dimethylaminopropylamine, 4-(2-aminoethyl)morpholine and piperazine, and combinations thereof.

8. The polymeric aminoacrylate of claim 1 , wherein the bireactive amine moieties derive from ethanolamine or piperazine.

9. The polymeric aminoacrylate of claim 1 , wherein poly(alkylene oxide) cores of the poly(alkylene glycol) diacrylate moieties have the formula: (C n H 2n O) x , where n is 1 to 6 and x is from 4 to 25.

10. The polymeric aminoacrylate of claim 1 , wherein the acrylate functionality of the polymeric aminoacrylate is 2.

11. The polymeric aminoacrylate of claim 1 , wherein the amine value is about 10 mgKOH/g or greater.

12. The polymeric aminoacrylate of claim 1 comprising a polymer formed by a Michael addition reaction between the poly(alkylene glycol) diacrylate and the bireactive amine.

13. The polymeric aminoacrylate of claim 1 , wherein in the Michael addition reaction, the poly(alkylene glycol) diacrylate and bireactive amine are present in a molar ratio of poly(alkylene glycol) diacrylate:bireactive amine of about 1.0:0.9 to about 1.0:0.1.

14. An energy curable ink or coating composition comprising the polymeric aminoacrylate of claim 1 .

15. The energy curable ink or coating composition of claim 14 , further comprising at least one free-radical polymerizable monomer or oligomer.

16. The energy curable ink or coating composition of claim 15 , wherein the at least one free-radical polymerizable monomer or oligomer is a diacrylate.

17. The energy curable ink or coating composition of claim 14 , further comprising at least one colorant.

18. The energy curable ink or coating composition of claim 14 , further comprising at least one photoinitiator.

19. The energy curable ink or coating composition of claim 14 , wherein the ink or coating composition contains about 100 ppb or less migratable components after curing the ink or coating composition.

20. The energy curable ink or coating composition of claim 14 , wherein the ink or coating composition contains about 50 ppb or less migratable components after curing the ink or coating composition.

21. The energy curable ink or coating composition of claim 14 , wherein the ink or coating composition contains about 10 ppb or less migratable components after curing the ink or coating composition.

22. The polymeric aminoacrylate of claim 1 , wherein the bireactive amine moieties are selected from primary alkanolamines and primary alkoxyamines.

23. The polymeric aminoacrylate of claim 1 , wherein the bireactive amine moieties derive from ethanolamine.

Assignees

• Sun Chemical Corp

Inventors

• Illsley Derek Ronald
• Herlihy Shaun Lawrence
• Mayers Sean Philip Francis

Classifications

• C09D11/30

  Inkjet printing inks · CPC title

• C09D11/107

  from unsaturated acids or derivatives thereof · CPC title

• C09D11/101 Primary

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title

• C09D135/02

  Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence) · CPC title

• C08F222/1063 Primary

  of alcohol terminated polyethers · CPC title