IP Library Granted Patent US 10,590,315
Granted Patent B2
US 10,590,315 · App. 15/242,855 · Granted Mar 17, 2020

Emulsion adhesive for washable film

Inventors: Alfredo Mueller (Zurich, CH); Jos Van Noort (Leiden, NL); Graham Yeadon (Marbach, CH)
Assignee: Avery Dennison Corporation
C09J133/08B32B7/12B32B27/06B32B38/10B32B43/006C09J7/29B32B2519/00C09J2201/122C09J2201/162C09J2201/606C09J2201/622C09J2203/334C09J2433/00Y10T156/1111Y10T156/1142Y10T156/1153Y10T428/24942Y10T428/2891
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Quick Facts
Patent No.
US 10,590,315
App. No.
15/242,855
Granted
Mar 17, 2020
Kind
B2
Abstract

This invention relates to removable pressure sensitive adhesive compositions and constructions that contain an emulsion acrylic pressure sensitive adhesive copolymer of a plurality of acrylic monomers and at least one polymerizable acid. The invention further relates to labels, particularly removable polymeric labels for use on reusable containers.

Claims (43)

1. A composition comprising;

a copolymer of copolymerizable monomers comprising

(a) at least one alkyl acrylate having from about 4 to about 12 carbon atoms in the alkyl group;

(b) at least one acid monomer;

(c) at least one hard monomer, wherein a homopolymer of the hard monomer is not inherently tacky at ambient temperatures and has a Tg greater than −25° C.;

(d) optionally, at least one multifunctional crosslinking monomer; and

(e) a neutralizer, the neutralizer comprising at least one of 2-[bis-(2-hydroxyethyl)-amino]-2-hydroxymethyl propane-1,3-diol, 2-amino-2-(hydroxymethyl)-1,3-propanediol, N-methyl-D-glucamine, N,N,N′,N′-tetrakis-(2-hydroxyethyl)-ethylenediamine, and N,N,N′,N′-tetrakis-(2-hydroxypropyl)-ethylenediamine.

2. The composition of claim 1 wherein the composition is coated on a facestock comprising (a) a first polymeric layer having a first coefficient of thermal expansion; and (b) a second polymeric layer having a second coefficient of thermal expansion underlying the first polymeric layer, wherein the first coefficient of thermal expansion is less than the second coefficient of thermal expansion.

3. A wash-off label comprising:

a first polymeric layer having a first coefficient of thermal expansion;

a second polymeric layer having a second coefficient of linear thermal expansion underlying the first polymeric layer, wherein the first coefficient of linear thermal expansion is less than the second coefficient of linear thermal expansion; and

an adhesive layer underlying the second polymeric layer, the adhesive layer comprising an emulsion based pressure sensitive adhesive composition comprising an acrylic pressure sensitive adhesive copolymer of copolymerizable monomers comprising at least one ethylenically unsaturated carboxylic acid and a neutralizer, the neutralizer comprising at least one of 2-[bis-(2-hydroxyethyl)-amino]-2-hydroxymethyl propane-1,3-diol, 2-amino-2-(hydroxymethyl)-1,3-propanediol, N-methyl-D-glucamine, N,N,N′,N′-tetrakis-(2-hydroxyethyl)-ethylenediamine, and N,N,N′,N′-tetrakis-(2-hydroxypropyl)-ethylenediamine; and

wherein the label is reversibly curled toward the first polymeric layer at a temperature at or above 50° C. and the adhesive is washed off upon exposure to an aqueous caustic solution at a temperature of at least 50° C.

4. The label of claim 3 wherein the label is bondable to a cylindrically curved surface of an article and the main expansion direction of the label extends in the circumferential direction of the article.

5. The label of claim 3 wherein the first polymeric layer and the second polymeric layer are coextruded.

6. The label of claim 3 wherein the first polymeric layer and the second polymeric layer are bonded to each other by a lamination adhesive.

7. The label of claim 3 further comprising a metal layer.

8. The label of claim 7 wherein the metal layer overlies the first polymeric layer.

9. The label of claim 3 further comprising a print layer.

10. The label of claim 9 wherein the print layer overlies the first polymeric layer.

11. The label of claim 3 wherein the pressure sensitive adhesive copolymer comprises a copolymer of (a) about 75% to about 90% by weight of at least one alkyl acrylates having from about 4 to about 12 carbon atoms in the alkyl group; (b) about 0.25% to about 5% by weight of at least one acid monomer; (c) about 10% to about 20% by weight of at least one hard monomer, (d) 0 to about 1% by weight of at least one multifunctional crosslinking monomer, wherein the weight is based on the total weight of the monomers.

12. The label of claim 9 wherein the print layer underlies the first polymeric layer.

13. A wash-off label comprising:

a polymeric layer comprising at least one shrinkable film wherein the film is stretched in at least one direction;

an adhesive layer underlying the polymeric layer, the adhesive layer comprising an emulsion based pressure sensitive adhesive composition comprising an acrylic pressure sensitive adhesive copolymer of copolymerizable monomers comprising at least one ethylenically unsaturated carboxylic acid, and a neutralizer, the neutralizer comprising at least one of 2-[bis-(2-hydroxyethyl)-amino]-2-hydroxymethyl propane-1,3-diol, 2-amino-2-(hydroxymethyl)-1,3-propanediol, N-methyl-D-glucamine, N,N,N′,N′-tetrakis-(2-hydroxyethyl)-ethylenediamine, and N,N,N′,N′-tetrakis-(2-hydroxypropyl)-ethylenediamine; and

wherein the polymeric layer irreversibly shrinks at a temperature at or above 50° C. and the adhesive is washed off upon exposure to an aqueous caustic solution at a temperature of at least 50° C.

14. A method of detaching a label from an article, wherein the label comprises:

a first polymeric layer having a first coefficient of linear thermal expansion;

a second polymeric layer having a second coefficient of linear thermal expansion underlying the first polymeric layer, wherein the first coefficient of linear thermal expansion is less than the second coefficient of linear thermal expansion; and

an adhesive layer underlying the second polymeric layer, the adhesive comprising an emulsion based pressure sensitive adhesive composition comprising an acrylic pressure sensitive adhesive copolymer of copolymerizable monomers comprising at least one ethylenically unsaturated carboxylic acid, and a neutralizer, the neutralizer comprising at least one of 2-[bis-(2-hydroxyethyl)-amino]-2-hydroxymethyl propane-1,3-diol, 2-amino-2-(hydroxymethyl)-1,3-propanediol, N-methyl-D-glucamine, N,N,N′,N′-tetrakis-(2-hydroxyethyl)-ethylenediamine, and N,N,N′,N′-tetrakis-(2-hydroxypropyl)-ethylenediamine;

the method comprising heating a washing liquid to form a hot washing liquid; and

gradually detaching the label from the article, wherein the step of gradually detaching the label from the article comprises the step of exposing the label to the hot washing liquid for at least a predetermined amount of time so that the label is reversibly curled toward the first polymeric layer thereby overcoming the adhesive force of the adhesive layer.

15. The method of claim 14 wherein the liquid comprises caustic soda.

16. The method of claim 14 wherein the hot washing liquid has a temperature in the range of about 50° C. to about 90° C.

17. The method of claim 14 wherein the pressure sensitive adhesive copolymer comprises a copolymer of (a) about 75% to about 90% by weight of at least one alkyl acrylates having from about 4 to about 12 carbon atoms in the alkyl group; (b) about 0.25% to about 5% by weight of at least one acid monomer; (c) about 10% to about 20% by weight of at least one hard monomer; (d) 0 to about 1% by weight of at least one multifunctional crosslinking monomer, wherein the weight is based on the total weight of the monomers.

18. The composition of claim 1 wherein the copolymer comprises a copolymer of (a) about 75% to about 90% by weight of one or more alkyl acrylates having from about 4 to about 12 carbon atoms in the alkyl group; (b) about 0.25% to about 5% by weight of one or more acid monomers; (c) about 10% to about 20% by weight of at least one hard monomer; (d) 0 to about 1% by weight of at least one multifunctional crosslinking monomers.

19. The composition of claim 1 wherein the one or more alkyl acrylates is selected from butyl acrylate, hexyl acrylate, heptyl acrylate, n-octyl acrylate, iso-octyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate, and nonyl acrylate, and mixtures of two or more thereof.

20. The composition of claim 1 wherein the one or more acid monomers is selected from acrylic acid, methacrylic acid, itaconic acid, beta-carboxyethyl-acrylate and mixtures of two or more thereof.

21. The composition of claim 1 wherein the one or more hard monomers is selected from methyl and ethyl acrylate, methyl and ethyl methacrylate, vinyl acetate, styrene and mixtures of two or more thereof.

22. The composition of claim 1 wherein the multifunctional monomer is selected from diallyl maleate, ethylene glycol dimethacrylate, tripropylene glycol diacrylate, allyl methacrylate, divinyl benzene, N,N′-methylene-bis-acrylamide, triallyl cyanurate, and mixtures of two or more thereof.

23. The composition of claim 1 further comprising an external crosslinking agent.

24. The composition of claim 1 further comprising an organic acid neutralized by the hydroxy functional amine.

25. The composition of claim 1 wherein the composition is washed off upon exposure to an aqueous caustic solution at a temperature of at least 50° C.

Assignments (3)
CHANGE OF CORPORATE ADDRESS Recorded Feb 9, 2024
From: AVERY DENNISON CORPORATION
To: AVERY DENNISON CORPORATION
Reel/Frame 066614/0887 →
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 →
Continuity (3)
Division 12447478
Provisional Application 60864028 · Nov 2, 2006
Related Publication 20160355708A1 · Dec 8, 2016