Adhesives comprising crosslinker with (meth)acrylate group and olefin group and methods

Patent metadata

Field	Value
Publication number	US-9475967-B2
Application number	US-201414767732-A
Country	US
Kind code	B2
Filing date	Apr 11, 2014
Priority date	Apr 15, 2013
Publication date	Oct 25, 2016
Grant date	Oct 25, 2016

Abstract

A pressure sensitive adhesive composition is described comprising at least 50 wt-% of polymerized units derived from alkyl meth(acrylate) monomer(s); and 0.2 to 15 wt-% of at least one cross-linking monomers comprising a (meth)acrylate group and a C 6 -C 20 olefin group, the olefin group being optionally substituted. In another embodiment, an adhesive composition is described comprising a syrup comprising i) a free-radically polymerizable solvent monomer; and ii) a solute (meth)acrylic polymer comprising polymerized units derived from one or more alkyl (meth)acrylate monomers; wherein the syrup comprises at least one crosslinking monomer or the (meth)acrylic solute polymer comprises polymerized units derived from at least one crosslinking monomer, the crosslinking monomer comprising a (meth)acrylate group and a C 6 -C 20 olefin group, the olefin group being optionally substituted. In yet other embodiments, methods of preparing adhesive compositions are described.

First claim

What is claimed is:

1. A pressure sensitive adhesive composition comprising:
at least 50 wt-% of polymerized units derived from alkyl (meth)acrylate monomer(s) having a glass transition temperature no greater than 0° C.; and
0.2 to 15 wt-% of at least one crosslinking monomer comprising a (meth)acrylate group and a C 6 -C 20 olefin group, the olefin group being straight-chained or branched and optionally substituted; wherein the crosslinked composition is a pressure sensitive adhesive.

2. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive comprises at least 70 wt-% of polymerized units derived from one or more alkyl (meth)acrylate monomer(s).

3. The pressure sensitive adhesive composition of claim 1 wherein the crosslinking monomer has the formula:

R1 is H or CH 3 ,
L is an optional linking group; and
R2 is an optionally substituted C 6 -C 20 olefin group.

4. The pressure sensitive adhesive composition of claim 3 wherein L comprises one or more alkylene oxide groups.

5. The pressure sensitive adhesive composition of claim 3 wherein the crosslinking monomer is selected from the group consisting of citronellyl (meth)acrylate, geraniol (meth)acrylate, farnesol (meth)acrylate, and undecenyl (meth)acrylate.

6. The pressure sensitive adhesive composition of claim 1 wherein the crosslinking monomers comprises an olefin group comprising 6 to 10 carbon atoms.

7. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive comprises a bio-based content of at least 25% of the total carbon content.

8. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive comprises polymerized units derived from 2-octyl (meth)acrylate.

9. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive further comprises filler.

10. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive composition further comprises polymerized units derived from at least one monomer selected from acid-functional monomers, non-acid functional polar monomers, vinyl monomers, and combinations thereof.

11. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive further comprises a multifunctional (meth)acrylate crosslinker, a triazine crosslinker, or a combination thereof.

12. The pressure sensitive adhesive composition of claim 1 wherein the crosslinked pressure sensitive adhesive exhibits a storage modulus of less than 3×10 6 dynes/cm 2 at 25° C. and a frequency of 1 Hz.

13. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive composition is cleanly removable from paper, or reusable, or has a shear to orange peel dry wall with a 250 g weight of at least 500 minutes, or a combination thereof.

14. A pressure sensitive adhesive article comprising the pressure sensitive adhesive composition of claim 1 disposed on a release liner.

15. A pressure sensitive adhesive article comprising the pressure sensitive adhesive composition of claim 1 on a backing.

16. An adhesive composition comprising a syrup comprising
i) a free-radically polymerizable solvent monomer; and
ii) a solute (meth)acrylic polymer comprising at least 50 wt-% of polymerized units derived from one or more alkyl (meth)acrylate monomers having a glass transition temperature no greater than 0° C.,

wherein the syrup comprises at least one crosslinking monomer or the (meth)acrylic solute polymer comprises polymerized units derived from at least one crosslinking monomer, the crosslinking monomer comprising a (meth)acrylate group and a C 6 -C 20 olefin group, the olefin group being straight-chained, branched, or cyclic and optionally substituted; wherein the crosslinked adhesive composition is a pressure sensitive adhesive.

17. The adhesive composition of claim 16 wherein the adhesive is a pressure sensitive adhesive.

18. A method of preparing an adhesive composition comprising:
a) providing a syrup according to claim 16 ; and
b) applying the syrup to a substrate; and
c) irradiating the applied syrup thereby crosslinking the adhesive composition.

19. A method of preparing an adhesive composition comprising:
a) polymerizing in an organic solvent
i) at least 50 wt-% of one or more alkyl meth(acrylate) monomer(s) having a glass transition temperature no greater than 0° C., and
ii) a crosslinking monomer, the crosslinking monomer comprising a (meth)acrylate group and a C 6 -C 20 olefin group, the olefin group being optionally substituted; and

b) applying the solution of polymerized monomers to a substrate; and
c) curing the solution thereby crosslinking the adhesive composition wherein the crosslinked adhesive composition is a pressure sensitive adhesive.

20. The pressure sensitive adhesive composition of claim 1 wherein the C 6 -C 20 olefin group of the crosslinking monomer is an alkenyl group selected from 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl; 1,1-dimethyl-2-butenyl; 1,1-dimethyl-3-butenyl; 1,2-dimethyl-1-butenyl; 1,2-dimethyl-2-butenyl; 1,2-dimethyl-3-butenyl; 1,3-dimethyl-1-butenyl; 1,3-dimethyl-2-butenyl; 1,3-dimethyl-3-butenyl; 2,2-dimethyl-3-butenyl; 2,3-dimethyl-1-butenyl; 2,3-dimethyl-2-butenyl; 2,3-dimethyl-3-butenyl; 3,3-dimethyl-1-butenyl; 3,3-dimethyl-2-butenyl; 1,1,2-trimethyl-2-propenyl; cyclohexenyl, dicyclopentenyl, and isomers of heptenyl, octenyl, and nonenyl.

21. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive composition further comprises a tackifier.

22. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive composition comprises 0 to 1.0 wt-% of polymerized units derived from acid-functional monomers.

Assignees

• 3M Innovative Properties Co

Inventors

• Lipscomb Corinne E
• Fansler Duane D
• Lewandowski Kevin M
• Janoski Jonathan E
• Seth Jayshree
• Weikel Arlin L
• Vanderzanden John W

Classifications

• C08L2312/06

  by radiation · CPC title

• B05D3/067

  Curing or cross-linking the coating · CPC title

• C09J2433/00

  Presence of (meth)acrylic polymer · CPC title

• C08K7/28

  Glass · CPC title

• C09J133/08 Primary

  Homopolymers or copolymers of acrylic acid esters · CPC title