IP Library Granted Patent US 10,968,369
Granted Patent B2
US 10,968,369 · App. 16/045,904 · Granted Apr 6, 2021

Crosslinkable polymer composition

Inventors: Shelly Peyton (Amherst, MA); John Klier (Leverett, MA); Yen Tran (Amherst, MA); Todd Emrick (South Deerfield, MA)
Assignee: THE UNIVERSITY OF MASSACHUSETTS
C09J7/385C08F220/20C08F220/28C08F220/34C08F220/38C08F220/281C08F220/286C08F220/382C08F2800/10C08F2810/20C08F2810/50C09J2301/414C09J2433/00
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Quick Facts
Patent No.
US 10,968,369
App. No.
16/045,904
Granted
Apr 6, 2021
Kind
B2
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.

Claims (49)

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.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 5, 2020
From: PEYTON, SHELLY; KLIER, JOHN; TRAN, YEN; EMRICK, TODD
To: THE UNIVERSITY OF MASSACHUSETTS
Reel/Frame 054283/0221 →
CONFIRMATORY LICENSE Recorded Aug 31, 2018
From: UNIVERSITY OF MASSACHUSETTS, AMHERST
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 047013/0046 →
CONFIRMATORY LICENSE Recorded Aug 6, 2018
From: UNIVERSITY OF MASSACHUSETTS, AMHERST
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 046723/0965 →
Continuity (2)
Provisional Application 62537130 · Jul 26, 2017
Related Publication 20190031925A1 · Jan 31, 2019