Adhesives comprising cyclic imide addition-fragmentation and adhesion agents

Patent metadata

Field	Value
Publication number	US-12398301-B2
Application number	US-202218706151-A
Country	US
Kind code	B2
Filing date	Nov 18, 2022
Priority date	Dec 6, 2021
Publication date	Aug 26, 2025
Grant date	Aug 26, 2025

Abstract

An adhesive composition is described comprising at least one cyclic imide monomer comprising an unsaturated carbonyl. The adhesive composition is a polymerizable composition or a polymerized composition. The polymerizable adhesive composition may comprise at least one monomer, oligomer, polymer, or a combination thereof comprising ethylenically unsaturated groups and/or an epoxy resin. The cyclic imide monomer may comprise an imide group with an α, β-unsaturated carbonyl in a heterocyclic ring wherein the ring comprises at least 6 covalently bonded atoms. Also described are methods of forming an adhesive coated substrate and articles.

First claim

What is claimed is:

1. A composition comprising an adhesive composition and a cyclic imide monomer having the structure:

wherein L is a covalent bond or an organic linking group;
Y is alkyl, aryl, hydroxyl, carboxylic acid, or an ethylenically unsaturated polymerizable group; and
R 1 and R 2 are substituents; and
an epoxy resin.

2. The composition of claim 1 wherein R 1 and R 2 are substituents such that the cyclic imide monomer ring-opens during polymerization thereby forming radicals including C1 to C4 alkyl groups.

3. The composition of claim 1 wherein L is (hetero) alkylene or (hetero) arylene.

4. The composition of claim 1 wherein Y is a carboxylic acidic group or a (meth)acrylate group.

5. The composition of claim 1 wherein L comprises at least one hydroxyl group.

6. A composition comprising an adhesive composition and a cyclic imide monomer having the structure:

wherein R is an organic linking group; and
R 1 and R 2 are independently substituents; and
an epoxy resin.

7. The composition of claim 6 wherein R 1 and R 2 are substituents such that the cyclic imide monomer ring-opens during polymerization thereby forming radicals including C1 to C4 alkyl groups.

8. The composition of claim 6 wherein R is (hetero) alkylene or (hetero) arylene, optionally comprising at least one pendant ethylenically unsaturated polymerizable group.

9. The composition of claim 1 wherein the adhesive composition comprises less than 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1 wt. % of the cyclic imide monomer.

10. The composition of claim 1 wherein the cyclic imide monomer comprises a (meth)acryl group.

11. The composition of claim 1 wherein the adhesive composition is a polymerizable composition or a polymerized composition.

12. The composition of claim 11 wherein the polymerizable composition comprises at least one monomer, oligomer, polymer, or a combination thereof comprising ethylenically unsaturated groups.

13. An adhesive coated article comprising a first substrate and the polymerized composition of claim 1 and a second substrate such the polymerized composition bonds the first substrate to the second substrate.

14. A composition comprising:
polymerized units having the structure:

wherein L is a covalent bond or a linking group;
Y is alkyl, aryl, hydroxyl, carboxylic acid, or an ethylenically unsaturated group;
R 1 and R 2 are independently substituents; and

P and P′ are independently polymerized units of an ethylenically unsaturated polymerizable monomer, oligomer, polymer, or combination thereof;
and an epoxy resin;
wherein the composition is an adhesive composition.

15. The composition of claim 6 wherein the adhesive composition comprises less than 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1 wt. % of the cyclic imide monomer.

16. The composition of claim 6 wherein the cyclic imide monomer comprises a (meth)acryl group.

17. The composition of claim 6 wherein the adhesive composition is a polymerizable composition or a polymerized composition.

18. The composition of claim 17 wherein the polymerizable composition comprises at least one monomer, oligomer, polymer, or a combination thereof comprising ethylenically unsaturated groups.

19. An adhesive coated article comprising a first substrate and the polymerized composition of claim 6 and a second substrate such the polymerized composition bonds the first substrate to the second substrate.

20. An adhesive coated article comprising a first substrate and the polymerized composition of claim 14 and a second substrate such the polymerized composition bonds the first substrate to the second substrate.

Assignees

• 3M Innovative Properties Company

Inventors

• Leone Amanda K
• Anderson Jonathan J
• Joly Guy D
• Abuelyaman Ahmed S
• Kropp Michael A
• Hartmann-Thompson Claire
• Mahoney Wayne S

Classifications

• C09J163/08

  Epoxidised polymerised polyenes · CPC title

• C09J4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 · CPC title

• C09J133/12 Primary

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C09J4/00 Primary

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title