Crosslinkable polymer composition

Patent metadata

Field	Value
Publication number	US-10968369-B2
Application number	US-201816045904-A
Country	US
Kind code	B2
Filing date	Jul 26, 2018
Priority date	Jul 26, 2017
Publication date	Apr 6, 2021
Grant date	Apr 6, 2021

Abstract

A crosslinkable polymer composition includes repeating units of formula (I)

and repeating units derived from a monomer having an ethylenically unsaturated group and a crosslinkable functional group, wherein the crosslinkable functional group is capable of forming a covalent linkage with a crosslinkable functional group of an adjacent repeating unit. R′ and R 2 are as defined herein. The crosslinkable polymer composition can be particularly useful, for example, for pressure sensitive adhesive or coating compositions. A method of making the polymer composition and a pressure sensitive adhesive and a coating are also described.

First claim

The invention claimed is:

1. A crosslinkable polymer composition comprising
a first polymer comprising repeating units of formula (I)

and
repeating units derived from a monomer comprising an ethylenically unsaturated group and a crosslinkable functional group, wherein the crosslinkable functional group is capable of forming a covalent linkage with a second crosslinkable functional group of an adjacent repeating unit, a crosslinker, or both, when pressure is applied to the crosslinkable polymer composition, a time sufficient to cure the crosslinkable polymer composition has passed, or both;
wherein the repeating units derived from a monomer comprising an ethylenically unsaturated group and a crosslinkable function group are of formula (II)

wherein in formula (I),
R 1 is independently at each occurrence hydrogen or methyl; and
R 2 is independently at each occurrence a C 4-12 alkyl group or a group of the formula

wherein R 5 is hydrogen or methyl and n is an integer from 1 to 230, and
wherein in formula (II),
R 3 is independently at each occurrence hydrogen or methyl;
R 4 is a C 1-14 alkylene group or a group of the formula

wherein p is an integar from 1 to 230; and
L 1 is a C 1-12 alkylene group.

2. The crosslinkable polymer composition of claim 1 , wherein
R 1 is hydrogen and R 3 is methyl;
R 2 is a group of the formula

wherein R 5 is hydrogen and n is an integer from 1 to 10; and
R 4 is a group of the formula

wherein p is 1.

3. The crosslinkable polymer composition of claim 1 wherein L 1 is a butylene group.

4. The crosslinkable polymer composition of claim 1 , comprising
60 to 99 mole percent repeating units according to formula (I); and
1 to 40 mole percent repeating units derived from a monomer comprising an ethylenically unsaturated group and a crosslinkable functional group;
wherein mole percent of each component is based on the total moles of repeating units according to formula (I) repeating units derived from a monomer comprising an ethylenically unsaturated group and a crosslinkable functional group.

5. The crosslinkable polymer composition of claim 1 , further comprising repeating units derived from a multifunctional crosslinker comprising at least two polymerizable groups of formula (V)

wherein R 6 is hydrogen or methyl.

6. The crosslinkable polymer composition of claim 5 , wherein the multifunctional crosslinker comprises a difunctional poly(ethylene glycol) crosslinker of formula (V)

wherein R 8 is hydrogen or methyl and m is an integer from 1 to 230.

7. The crosslinkable polymer composition of claim 5 , wherein repeating units derived from the multifunctional crosslinker are present in an amount of less than 1 weight percent, based on the total weight of the crosslinkable polymer composition.

8. The crosslinkable polymer composition of claim 1 , further comprising repeating units derived from an ethylenically unsaturated monomer in an amount effective to increase the glass transition temperature of the crosslinkable polymer composition.

9. A method for the manufacture of a crosslinkable polymer composition according to claim 1 , the method comprising:
copolymerizing a first monomer of formula (VII) and a second monomer of formula (VIII)

wherein
R 1 and R 3 are independently at each occurrence hydrogen or methyl;
R 2 is a C 4-12 alkyl group or a group of the formula

wherein R 5 is hydrogen or methyl and n is an integer from 1 to 230;
R 4 is a C 1-14 alkylene group or a group of the formula

wherein p is an integer from 1 to 230; and
L 1 is a C 1-12 alkylene group to provide a disulfide-containing polymer; and

reducing the disulfide-containing polymer to provide the crosslinkable polymer composition.

10. The method of claim 9 , wherein reducing the disulfide-containing polymer comprises contacting the disulfide-containing polymer with a reducing agent.

11. A pressure sensitive adhesive or a coating comprising a crosslinked polymer composition derived from the crosslinkable polymer composition of claim 1 .

12. The pressure sensitive adhesive or coating of claim 11 , wherein the crosslinked polymer composition is derived from a crosslinkable polymer composition comprising repeating units according to formula (I) and (II), and the crosslinked polymer composition comprises a plurality of disulfide crosslinks formed between repeating units of formula (II).

13. The pressure sensitive adhesive or coating of claim 11 , wherein the crosslinked polymer composition is derived from a crosslinkable polymer composition comprising repeating units according to formula (I) and (II), and the crosslinked polymer composition is crosslinked by reaction with a compound comprising at least two alkenyl groups capable of reacting with the crosslinkable polymer composition to form thioether bonds.

14. A method of making a pressure sensitive adhesive or a coating, the method comprising:
contacting a substrate with the crosslinkable polymer composition of claim 1 ; and
curing the crosslinkable polymer composition to provide the pressure sensitive adhesive or the coating;
wherein curing the crosslinkable polymer composition comprises applying pressure to the pressure sensitive adhesive, waiting for a time sufficient to cure the crosslinkable polymer composition, or both.

Assignees

• Univ Massachusetts

Inventors

• Peyton Shelly
• Klier John
• Tran Yen
• Emrick Todd

Classifications

• C08F220/20 Primary

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C08F220/286

  and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate · CPC title

• C08F220/34

  Esters containing nitrogen {, e.g. N,N-dimethylaminoethyl (meth)acrylate} · CPC title

• C08F220/382

  and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate · CPC title

• C08F2810/20

  leading to a crosslinking, either explicitly or inherently · CPC title