IP Library Granted Patent US 10,294,397
Granted Patent B2
US 10,294,397 · App. 12/704,942 · Granted May 21, 2019

Adhesive compounds

Inventors: Nagarajan Srivatsan (Pasadena, CA); Prakash Mallya (Pasadena, CA); Daniel L. Holguin (Pasadena, CA); Dominique Wouters (Pasadena, CA); Eric L. Bartholomew (Pasadena, CA); Liza P. Lofton (Pasadena, CA)
Assignee: Avery Dennison Corporation
C09J123/02B32B5/18B32B27/065B32B27/18B32B27/306B32B27/308B32B27/32B32B27/34B32B27/40C08K5/0091C09J151/06B32B2266/025B32B2266/0221B32B2266/0242B32B2266/0278B32B2307/50B32B2307/712B32B2405/00B32B2605/00C08L23/18C08L91/00C08L2666/04C08L2666/24Y10T428/249983
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Quick Facts
Patent No.
US 10,294,397
App. No.
12/704,942
Granted
May 21, 2019
Kind
B2
Abstract

The invention relates to multiphase compositions of matter comprising at least an acrylic phase and a hydrocarbon phase, and more specifically to pressure sensitive adhesive compositions of matter of an acrylic-hydrocarbon polymer and an additional hydrocarbon component which has a molecular weight of at least 1,000 and may include one or both of an oligomeric hydrocarbon and a polymeric hydrocarbon.

Claims (47)

1. A pressure-sensitive adhesive composition comprising:

a hybrid acrylic-rubber graft copolymer formed by reacting an acrylic monomer system comprising at least one alkyl acrylate ester containing from about 2 to about 20 carbon atoms in the alkyl group in the presence of a macromer selected from ethylene-butylene macromers, ethylene-propylene macromers, ethylene-butylene-propylene macromers, isobutylene macromers, and mixtures thereof, the graft copolymer including a continuous acrylic phase and a discontinuous hydrocarbon phase;

an additional hydrocarbon compound having a molecular weight of at least 1,000 and compatible with the macromer, the additional hydrocarbon compound is an oligomeric hydrocarbon or polymeric hydrocarbon or a combination of both,

wherein the macromer is present in an amount of from 5% to about 50% by weight of the acrylic monomer system and the macromer,

wherein the additional hydrocarbon comprises from about 5% to about 75% of the total weight of the pressure-sensitive adhesive composition, and

wherein the additional hydrocarbon compound comprises a material selected from the group consisting of hydrogenated liquid polyisoprene, methacrylic functionalized liquid isoprene rubber, maleic anhydride functionalized polypropylenes, carboxyl-terminated polybutadiene, epoxidized hydroxyl terminated polybutadiene resin, hydroxy terminated polybutadiene resin, hydroxyl terminated 1,3-butadiene homopolymer, vinyl functional polybutadiene, and combinations thereof.

2. The pressure-sensitive adhesive of claim 1 , further comprising a cross-linking agent.

3. The pressure-sensitive adhesive of claim 1 , wherein both of the macromer component of the graft copolymer and the hydrocarbon compound are hydrogenated.

4. The pressure-sensitive adhesive of claim 1 , wherein either one or both of the graft copolymer and the hydrocarbon compound are crystalline.

5. The pressure-sensitive adhesive of claim 1 , wherein either one or both of the graft copolymer and the hydrocarbon compound contain reactive sites.

6. The pressure-sensitive adhesive of claim 5 , wherein the reactive sites are selected from carboxylic acid, hydroxyl, anhydride, aldehyde, ketone, acetate, amine, amide, aziridine, epoxide, mercapto, acrylate, methacrylate, vinyl, and mixtures thereof.

7. The pressure-sensitive adhesive of claim 1 , wherein the hydrocarbon compound is made of monomers selected from ethylene, propylene, butadiene, isoprene, isobutylene, hexene, octene, and mixtures thereof.

8. A product comprising:

a layer of foam having two surfaces; and

a pressure-sensitive adhesive composition according to claim 1 ,

wherein the pressure-sensitive adhesive is applied to one or both surfaces of the layer of foam.

9. The product of claim 8 , wherein the foam is made of a material selected from polyolefins, copolymers of polyolefins with other monomers, copolymer of polyolefins with acrylics, copolymer of polyolefins with vinyl acetates, polyurethane, and acrylics.

10. The product of claim 8 , further comprising a barrier layer disposed between the layer of foam and the pressure-sensitive adhesive composition.

11. The product of claim 10 , wherein the barrier layer includes a material selected from polyurethane, poly(ethylene-co-acrylic acid), poly(ethylene-co-acrylic acid) metal salts, poly(ethylene-co-methacrylic acid), poly(ethylene-co-methacrylic acid) metal salts, poly(ethylene-co-methyl acrylate), poly(ethylene-co-vinyl acetate), poly(ethylene-co-vinyl acetate-co-carbon monoxide), poly(vinyl alcohol-co-ethylene), and poly(ethylene-co-acrylic acid).

12. The product of claim 10 , wherein:

the pressure-sensitive adhesive further includes a cross-linking agent; and

the barrier layer has solubility parameters that are higher than corresponding solubility parameters for the tackifier compound and the cross-linking agent.

13. The pressure-sensitive adhesive of claim 1 , wherein the pressure-sensitive adhesive is further cured by radiation selected from ultraviolet radiation and electron beam radiation or by incorporation of a cross-linking agent.

14. The pressure-sensitive adhesive of claim 1 , wherein the hydrocarbon oligomer and the hydrocarbon polymer are in one or more of an acrylic phase of the compound, a first hydrocarbon phase of the compound that contains a hydrocarbon macromonomer, and a second hydrocarbon phase of the compound that contains the hydrocarbon oligomer and the hydrocarbon polymer.

15. The pressure-sensitive adhesive of claim 14 , further comprising a silicone phase.

16. The pressure-sensitive adhesive of claim 14 , further comprising a high glass transition temperature material.

17. The pressure-sensitive adhesive of claim 16 , wherein the high glass transition temperature material is selected from polystyrene and poly methyl methacrylate.

18. The pressure-sensitive adhesive of claim 1 , further comprising a tackifier compound compatible with the hydrocarbon phase and incompatible with the acrylic phase.

19. The pressure-sensitive adhesive of claim 1 , further comprising a tackifier compound that is miscible in at least a portion of the composition.

20. The pressure-sensitive adhesive of claim 1 , wherein the acrylic monomer system is formed from about 35% to 100% total weight of the at least one alkyl acrylate ester containing from about 4 to about 8 carbon atoms in the alkyl group.

21. The pressure-sensitive adhesive of claim 20 , further comprising a tackifier compound compatible with the hydrocarbon phase and incompatible with the acrylic phase.

22. The pressure-sensitive adhesive of claim 20 , further comprising a tackifier compound that is miscible in at least a portion of the composition.

23. The pressure-sensitive adhesive of claim 20 , wherein the acrylic monomer system comprises from about 95% to about 90% by weight 2-ethyl hexyl acrylate and from about 5% to about 10% by weight acrylic acid.

24. The pressure-sensitive adhesive of claim 1 , wherein the acrylic monomer system comprises from about 95% to about 90% by weight 2-ethyl hexyl acrylate and from about 5% to about 10% by weight acrylic acid.

25. The pressure-sensitive adhesive of claim 1 , wherein the additional hydrocarbon compound is fully hydrogenated.

26. The pressure-sensitive adhesive of claim 1 , wherein the additional hydrocarbon compound is hydrogenated liquid polyisoprene or methacrylic functionalized liquid isoprene rubber.

27. The pressure-sensitive adhesive of claim 1 , wherein the additional hydrocarbon compound is maleic anhydride functionalized polypropylene.

28. The pressure-sensitive adhesive of claim 1 , wherein the additional hydrocarbon compound is carboxyl-terminated polybutadiene or epoxidized hydroxyl terminated polybutadiene resin.

29. The pressure-sensitive adhesive of claim 1 , wherein the additional hydrocarbon compound is hydroxyl terminated 1,3-butadiene homopolymer.

30. The pressure-sensitive adhesive of claim 1 , wherein the additional hydrocarbon compound is vinyl functional polybutadiene.

31. The pressure-sensitive adhesive of claim 1 , wherein the additional hydrocarbon compound is hydroxyl terminated polybutadiene resin.

32. A pressure-sensitive adhesive composition comprising:

a hybrid acrylic-rubber copolymer having an acrylic backbone and a pendant macromer formed by reacting an acrylic monomer system comprising at least one alkyl acrylate ester containing from about 2 to about 20 carbon atoms in the alkyl group in the presence of a macromer selected from ethylene-butylene macromers, ethylene-propylene macromers, ethylene-butylene-propylene macromers, isobutylene macromers, and mixtures thereof, the copolymer including a continuous acrylic phase and a discontinuous hydrocarbon phase;

an additional hydrocarbon compound having a molecular weight of at least 1,000 and compatible with the macromer, the additional hydrocarbon compound is an oligomeric hydrocarbon or polymeric hydrocarbon or a combination of both,

wherein the macromer is present in an amount of from 5% to about 50% by weight of the acrylic monomer system and the macromer,

wherein the additional hydrocarbon comprises from about 5% to about 75% of the total weight of the pressure-sensitive adhesive composition, and

wherein the additional hydrocarbon compound comprises a material selected from the group consisting of hydrogenated liquid polyisoprene, methacrylic functionalized liquid isoprene rubber, maleic anhydride functionalized polypropylenes, carboxyl-terminated polybutadiene, epoxidized hydroxyl terminated polybutadiene resin, hydroxyl terminated polybutadiene resin, hydroxyl terminated 1,3-butadiene homopolymer, vinyl functional polybutadiene, and combinations thereof.

Assignments (4)
CHANGE OF CORPORATE ADDRESS Recorded Feb 9, 2024
From: AVERY DENNISON CORPORATION
To: AVERY DENNISON CORPORATION
Reel/Frame 066544/0487 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS FROM 8080 NORTON PARKWAY, MENTOR, OHIO 44060 TO 207 GOODE AVENUE, GLENDALE, CALIFORNIA 91203 PREVIOUSLY RECORDED AT REEL: 059822 FRAME: 0817. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jul 21, 2022
From: AVERY DENNISON CORPORATION
To: AVERY DENNISON CORPORATION
Reel/Frame 060799/0698 →
CHANGE OF CORPORATE ADDRESS Recorded Apr 29, 2022
From: AVERY DENNISON CORPORATION
To: AVERY DENNISON CORPORATION
Reel/Frame 059822/0817 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2010
From: SRIVATSAN, NAGARAJAN; MALLYA, PRAKASH; HOLGUIN, DANIEL L.; WOUTERS, DOMINIQUE; BARTHOLOMEW, ERIC L.; LOFTON, LIZA P.
To: AVERY DENNISON CORPORATION
Reel/Frame 024623/0455 →
Continuity (2)
Provisional Application 61152404 · Feb 13, 2009
Related Publication 20100266837A1 · Oct 21, 2010