Adhesive article and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-11370940-B2
Application number	US-201816615477-A
Country	US
Kind code	B2
Filing date	May 16, 2018
Priority date	May 24, 2017
Publication date	Jun 28, 2022
Grant date	Jun 28, 2022

Abstract

An adhesive article comprising first and second tacky latent adhesive layers disposed on respective first and second opposed major surfaces of a substrate. Each of the first and second tacky latent adhesive layers independently comprises at least one polymerizable component, and a redox initiator system comprising a transition metal complex that participates in a redox cycle, an oxidizing agent, and a blocked reducing agent represented by the formula ((I). Each of R1 and R2 are independently H, an alkyl, an aryl, or RPhoto5 with the proviso that at least one of R1 and R2 is RPhoto. RPhoto represents a photoremovable group. Each of R3 and R4 independently represents H, an alkyl group, or an aryl group comprising a monovalent ester, ether, urethane, or carbonate group. Methods of making and using the adhesive articles are also disclosed.

First claim

What is claimed is:

1. An adhesive article comprising:
a substrate having first and second opposed major surfaces;
first and second tacky latent adhesive layers disposed on the respective first and second opposed major surfaces of the substrate, wherein each of the first and second tacky latent adhesive layers independently comprises:
at least one polymerizable component, and
a redox initiator system comprising:
a transition metal complex that participates in a redox cycle;
an oxidizing agent; and
a blocked reducing agent represented by the formula

wherein
each of R 1 and R 2 are independently H, an alkyl, an aryl, or R Photo , with the proviso that at least one of R 1 and R 2 is R Photo ;
R Photo represents a photoremovable group;
each of R 3 and R 4 independently represents H, an alkyl group, or an aryl group comprising a monovalent ester, ether, urethane, or carbonate group.

2. The adhesive article of claim 1 , wherein the substrate comprises an acrylic core.

3. The adhesive article of claim 1 , wherein the first and second tacky adhesive layers have the same composition.

4. An adhesive article according to claim 1 , further comprising a first release liner releasably adhered to the first tacky latent adhesive layer.

5. An adhesive article according to claim 4 , wherein the second tacky latent adhesive layer is releasably adhered to the first release liner opposite the first tacky latent adhesive layer, and wherein the adhesive article comprises a roll.

6. An adhesive article according to claim 4 , further comprising a second release liner releasably adhered to the second tacky latent adhesive layer.

7. The adhesive article of claim 1 , wherein the photoremovable group R Photo is selected from phenacyl groups, 2-alkylphenacyl groups, ethylene-bridged phenacyl groups, p-hydroxyphenacyl groups, monovalent benzoin groups, o- or p-nitrobenzyl groups, o-nitro-2-phenethyloxycarbonyl groups, coumarin-4-yl-methyl groups, benzyl groups, o- or p-hydroxybenzyl groups, o- or p-hydroxynapthyl groups, 2,5-dihydroxybenzyl groups, 9-phenylthioxanthyl groups, 9-phenylxanthyl groups, anthraquinon-2-yl groups, 8-halo-7-hydroxyquinoline-2-yl-methyl groups, and monovalent O,O-di(pivaloyl) ethylene glycol groups.

8. The adhesive article of claim 1 , wherein the transition metal complex is represented by the formula:
[ML p ] n+ A − , wherein M is a transition metal that participates in a redox cycle,
L is a ligand,
A − is an anion,
n is the formal charge on the transition metal having a whole number value of 1 to 7, and

p is the number of ligands on the transition metal having a number value of 1 to 9.

9. The adhesive article of claim 8 , wherein M is selected from Cu, Fe, Ru, Cr, Mo, Pd, Ni, Pt, Mn, Rh, Re, Co, V, Au, Nb, and Ag.

10. The adhesive article of claim 1 , wherein the redox initiator system is present in the first tacky latent adhesive layer in an amount of 0.1 to 10 parts by weight, based on 100 parts by weight of the at least one polymerizable component.

11. The adhesive article of claim 1 , further comprising a secondary reducing agent selected from tertiary amines, aromatic sulfinate salts, thioureas, and combinations thereof.

12. The adhesive article of claim 1 , wherein the oxidizing agent of the redox initiator system is selected from persulfuric acid and salts thereof, peroxides, transition metals, perboric acid and salts thereof, permanganic acid and salts thereof, perphosphoric acid and salts thereof, and combinations thereof.

13. The adhesive article of claim 1 , wherein the first tacky latent adhesive layer comprises at least one polymerizable vinyl monomer and the redox initiator system.

14. The adhesive article of claim 1 , wherein the mole ratio of the oxidizing agent to blocked reducing agent is from 1:1.5 to 1.5:1.

15. The adhesive article of claim 1 , wherein, in the first tacky latent adhesive layer, the oxidizing agent and blocked reducing agent are present in an amount of 0.01 to 10 parts by weight, based on the total weight of the at least one polymerizable component.

16. The adhesive article of claim 1 , further comprising 1 to 35 parts by weight of a toughening agent per 100 parts by weight of the at least one polymerizable component.

17. The adhesive article of claim 1 , wherein the polymerizable component comprises a reactive oligomer having pendent polymerizable groups.

18. The adhesive article of claim 17 , wherein the reactive oligomer comprises, based on the total of monomer units a) to c):
a) greater than 50 parts by weight of (meth)acrylate ester monomer units;
b) 0.5 to 10 parts by weight of monomer units having at least one pendent free-radically polymerizable functional group; and
c) 0 to 20 parts by weight of other polar monomer units.

19. A method of making an adhesive article, the method comprising:
disposing first and second tacky latent adhesive layers on respective first and second opposed major surfaces of a substrate, wherein the first and second tacky latent adhesive layers independently comprise:
at least one polymerizable component, and
a redox initiator system comprising:
a transition metal complex that participates in a redox cycle;
an oxidizing agent; and
a blocked reducing agent represented by the formula

wherein
each of R 1 and R 2 are independently H, an alkyl, an aryl, or R Photo , with the proviso that at least one of R 1 and R 2 is R Photo ;
R Photo represents a photoremovable group;
each of R 3 and R 4 independently represents H, an alkyl group, or an aryl group comprising a monovalent ester, ether, urethane, or carbonate group.

20. A method of using the adhesive article of claim 1 , the method comprising:
exposing the first and second tacky latent adhesive layers to actinic electromagnetic radiation to provide exposed first and second tacky latent adhesive layers; and
contacting the exposed first and second tacky latent adhesive layer with respective first and second adherends.

Assignees

• 3M Innovative Properties Co

Inventors

• Townsend Erik M
• Ranade Shantanu R
• Moser William H
• Shafer Kathleen S
• Kropp Michael A
• Seth Jayshree
• Behling Ross E

Classifications

• C08K5/1565

  Five-membered rings · CPC title

• C09J7/40

  characterised by release liners · CPC title

• C09J7/255 Primary

  Polyesters · CPC title

• C09J2301/416

  use of irradiation · CPC title

• C08F4/40

  Redox systems · CPC title