Adhesives comprising poly(isobutylene) copolymers comprising pendent free-radically polymerizable quaternary ammonium substituent

Patent metadata

Field	Value
Publication number	US-9562180-B2
Application number	US-201314354998-A
Country	US
Kind code	B2
Filing date	Jan 30, 2013
Priority date	Mar 29, 2012
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

Adhesive compositions comprising a copolymer of isobutylene repeat units and alkene repeat units are described. At least a portion of the alkene repeat units are bonded to a pendent nitrogen atom of a quaternary ammonium salt comprising a free-radically polymerizable substituent. The adhesive optionally comprises other components such as tackifier, unfunctionalized polyisobutylene polymer, plasticizer, and combinations thereof.

First claim

What is claimed is:

1. An adhesive composition comprising a copolymer of isobutylene repeat units and alkene repeat units derived from isoprene, butadiene, or a combination thereof;
wherein at least a portion of the alkene repeat units are bonded to a pendent nitrogen atom of a quaternary ammonium salt comprising a free-radically polymerizable substituent, wherein the copolymer is of the formula

wherein a is at least 20, the sum of b and c is at least one, and Z is a quaternary ammonium salt group comprising a free-radically polymerizable substituent, and optionally a tackifier.

2. The adhesive composition of claim 1 comprising greater than 0% by weight but less than 20% by weight of alkene repeat units bonded to the nitrogen atom of the quaternary amine salt group.

3. The adhesive composition of claim 1 , wherein the quaternary ammonium salt group, Z, is of the formula:
— + (NR 2 R 3 R 4 )(X 2 ) − or

where R 2 comprises a free-radically polymerizable group, and each of R 3 and R 4 are independently a C 1 -C 18 alkyl; and
X 2 is halogen.

4. The adhesive composition of claim 1 wherein the free-radically polymerizable group or R 2 is a (meth)acrylate or (meth)acrylamide group.

5. The adhesive composition of claim 1 wherein the copolymer has a molecular weight (Mw) of 50,000 to 5,000,000.

6. The adhesive composition of claim 5 wherein the copolymer has a molecular weight (Mw) no greater than 1,000,000 g/mole.

7. The adhesive composition of claim 1 further comprising a photocrosslinking agent.

8. The adhesive composition of claim 7 wherein the photocrosslinking agent is selected from aldehydes, ketones, quinones, thioxanthones and chromophore-substituted vinyl halomethyl-s-triazines photocrosslinking agents.

9. The adhesive composition of claim 1 further comprising 5 to 50 wt.-% of tackifier.

10. The adhesive composition of claim 1 further comprising 5 to 50 wt.-% of an unfunctionalized polyisobutylene polymer.

11. The adhesive composition of claim 10 wherein the unfunctionalized polyisobutylene polymer has a molecular weight no greater than 100,000 g/mole.

12. The adhesive composition of claim 1 further comprising a plasticizer.

13. The adhesive composition of claim 1 wherein the adhesive is a hot-melt adhesive.

14. A crosslinked adhesive composition of claim 1 .

15. An adhesive article comprising the adhesive of claim 14 on a backing.

16. An adhesive article comprising the adhesive of claim 1 on a backing.

17. The adhesive of claim 1 wherein b is at least one.

18. The adhesive of claim 17 wherein c is zero.

Assignees

• 3M Innovative Properties Co

Inventors

• Lee Hae-Seung
• Chatterjee Joon
• Gaddam Babu N

Classifications

• C08F8/32 Primary

  by reaction with amines · CPC title

• C09J2451/00

  Presence of graft polymer · CPC title

• Y10T428/2887

  including nitrogen containing polymer [e.g., polyacrylonitrile, polymethacrylonitrile, etc.] · CPC title

• C08K5/3492

  Triazines · CPC title

• Y10T428/2809

  including irradiated or wave energy treated component · CPC title