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

Patent metadata

Field	Value
Publication number	US-2016017187-A1
Application number	US-201414767732-A
Country	US
Kind code	A1
Filing date	Apr 11, 2014
Priority date	Apr 15, 2013
Publication date	Jan 21, 2016
Grant date	—

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 crosslinking 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

1 . A pressure sensitive adhesive composition 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 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.

2 . The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive comprises at least 55, 60, 65, or 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, undecenyl(meth)acrylate, and oleyl(meth)acrylate.

6 . The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive composition comprises at least 50, 55, 60, 65, or 70 wt-% of polymerized units of alkyl(meth)acrylates comprising 6 to 20 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 - 11 . (canceled)

12 . 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.

13 . 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.

14 . The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive exhibits a 180° degree peel adhesion to stainless steel of at least 15 N/dm after curing.

15 - 16 . (canceled)

17 . 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.

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

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

20 . An adhesive composition 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 straight-chained, branched, or cyclic and optionally substituted.

21 . The adhesive composition of claim 20 wherein the adhesive is a pressure sensitive adhesive.

22 - 24 . (canceled)

25 . A method of preparing an adhesive composition comprising:
a) providing a syrup according to claim 20 ; and b) applying the syrup to a substrate; and c) irradiating the applied syrup thereby crosslinking the adhesive composition.

26 . (canceled)

27 . A method of preparing an adhesive composition comprising:
a) polymerizing in an organic solvent
i) one or more alkyl meth(acrylate) monomer(s), 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.

28 - 31 . (canceled)

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

• C08K3/36

  Silica · CPC title

• B05D3/067

  Curing or cross-linking the coating · CPC title

• B05D1/42

  by non-rotary members · CPC title

• C08K7/28

  Glass · CPC title

• C09J133/08 Primary

  Homopolymers or copolymers of acrylic acid esters · CPC title