Acrylate adhesive with vinylsilane crosslinking agents

Patent metadata

Field	Value
Publication number	US-10100237-B2
Application number	US-201515326696-A
Country	US
Kind code	B2
Filing date	Aug 31, 2015
Priority date	Sep 2, 2014
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

An (meth)acrylate pressure-sensitive adhesive copolymer crosslinking by a vinyl silicon crosslinking agent is described.

First claim

What is claimed is:

1. A free-radically curable composition comprising:
a. a (meth)acrylate monomer mixture comprising at least one (meth)acrylate ester,
b. a vinyl siloxane crosslinking agent having at least two vinyl groups, and

a free radical initiator;
wherein the vinyl siloxane crosslinking agent is of the formula:

wherein Z is a vinyl group,
R 1 is a monovalent hydrocarbyl group;
a is 0 to 85
b is 2 to 30.

2. The composition of claim 1 comprising 0.1 to 10 parts by weight of the crosslinking agent relative to 100 parts by weight of the monomer mixture.

3. The composition of claim 1 wherein the monomer mixture comprises
i. 85 to 99.5 parts by weight of an (meth)acrylic acid ester;
ii. 0.5 to 15 parts by weight of an acid functional monomer;
iii. 0 to 20 parts by weight of a non-acid functional, ethylenically unsaturated polar monomer;
iv. 0 to 5 parts by weight of a vinyl monomer,
v. 0.1 to 5 parts by weight of the crosslinking agent,
vi. wherein the sum is 100 parts by weight.

4. A syrup polymer composition comprising
i) a (meth)acrylic solute copolymer component comprising polymerized units derived from one or more alkyl (meth)acrylate monomers;
ii) a free-radically polymerizable solvent monomer component;
iii) a vinyl siloxane crosslinking agent having at least two vinyl groups; and
wherein the solvent monomer comprises the crosslinking agent and/or the (meth)acrylic solute copolymer comprises polymerized units derived from at least one crosslinking agent;

wherein the vinyl siloxane crosslinking agent of the formula:

wherein Z is a vinyl group,
R 1 is a monovalent hydrocarbyl group;
a is 0 to 85
b is 2 to 30.

5. The composition of claim 4 wherein the solute copolymer comprises interpolymerized monomer units of the crosslinking agent.

6. The composition of claim 4 wherein the solvent monomer component contains the crosslinking agent.

7. The syrup polymer composition of claim 4 comprising:
a) first component solute copolymer comprising:
i. 85 to 99.5 parts by weight of an (meth)acrylic acid ester monomer units;
ii. 0.5 to 15 parts by weight of an acid functional monomer units;
iii. 0 to 20 parts by weight of a non-acid functional, ethylenically unsaturated polar monomer units;
iv. 0 to 5 parts by weight of a vinyl monomer units,
v. 0 to 5 parts by weight of a monomer units of the crosslinking agent;
wherein the sum is 100 parts by weight; and

b) a second component comprising at least one free-radically polymerizable solvent monomer and optional the crosslinking agent, and
c) 0.1 to 10 parts by weight of the crosslinking agent in the solute copolymer and/or the solvent monomer component, relative to a) plus b).

8. A method of making an (meth)acrylate adhesive copolymer comprising
a) partially polymerizing a (meth)acrylate monomer composition, said monomer mixture optionally containing a vinyl siloxane crosslinking agent having at least two vinyl groups to produce a syrup copolymer having a solute copolymer and solvent monomer,
b) adding a vinyl siloxane crosslinking agent to the syrup copolymer composition of step a) if not initially present in the monomer mixture,
c) further photopolymerizing the syrup polymer composition;

wherein the vinyl siloxane crosslinking agent is of the formula:

wherein Z is a vinyl group,
R 1 is a monovalent hydrocarbyl group;
a is 0 to 85
b is 2 to 30.

9. The method of claim 8 wherein the monomer mixture comprises:
i. 85 to 99.5 parts by weight of an (meth)acrylic acid ester monomer units;
ii. 0.5 to 15 parts by weight of an acid functional monomer units;
iii. 0 to 10 parts by weight of a non-acid functional, ethylenically unsaturated polar monomer units;
iv. 0 to 5 parts by weight of a vinyl monomer units,
v. 0 to 5 parts by weight of the crosslinking agent.

10. The method of claim 8 comprising 0.1 to 10 parts by weight of the vinyl siloxane crosslinking agent, relative to 100 parts by weight of monomer.

11. A polymerizable solution comprising:
i. 85 to 99.5 parts by weight of an (meth)acrylic acid ester;
ii. 0.5 to 15 parts by weight of an acid functional monomer;
iii. 0 to 20 parts by weight of a non-acid functional, ethylenically unsaturated polar monomer;
iv. 0 to 5 parts by weight of a vinyl monomer, wherein the sum of i to iv is 100 parts by weight
v. 0.1 to 10 parts by weight of the vinyl siloxane crosslinking agent, relative to 100 parts by weight of i to iv;
b) a solvent, and
c) an initiator;

wherein the vinyl siloxane crosslinking agent is of the formula:

wherein Z is a vinyl group,
R 1 is a monovalent hydrocarbyl group;
a is 0 to 85
b is 2 to 30.

12. A pressure-sensitive adhesive composition comprising (meth)acrylate copolymer crosslinked by a vinyl siloxane crosslinking agent having at least two vinyl groups;
wherein the copolymer is of the formula:
˜[M acrylate ] m -[M acid ] n -[M polar ] o -[M vinyl ] p [M xlink ] q ˜, where

[M acrylate ] represents polymerized acrylate ester monomer units, where subscript m corresponds to 85 to 99.5 parts s by weight thereof;
[M acid ] represents polymerized acid monomer units, where subscript n corresponds to 0.5 to 15 parts by weight thereof;
[M polar ]- represents polymerized non-acid functional polar monomer units, where subscript o corresponds to 0 to 20 parts by weight thereof;
[M vinyl ] represents polymerized other monomer units, where subscript p corresponds to 0 to 5 parts by weight thereof; wherein the sum of n, m, o and p is 100 parts by weight; and
[M xlink ] represents polymerized vinyl siloxane monomer units,
where subscript q is 0.1 to 10 parts, relative to 100 parts by weight of the sum of n, m, o and p;
wherein the vinyl siloxane crosslinking agent is of the formula:

wherein Z is a vinyl group,
R 1 is a monovalent hydrocarbyl group;
a is 0 to 85
b is 2 to 30.

Assignees

• 3M Innovative Properties Co

Inventors

• Lipscomb Corinne E
• Lewandowski Kevin M
• Thomas Carla S

Classifications

• C09J7/385

  Acrylic polymers · CPC title

• C09J2483/00

  Presence of polysiloxane · CPC title

• C09J143/04 Primary

  Homopolymers or copolymers of monomers containing silicon · CPC title

• C09J2433/00

  Presence of (meth)acrylic polymer · CPC title

• C09J151/085

  on to polysiloxanes · CPC title