IP Library Granted Patent US 8,828,181
Granted Patent B2
US 8,828,181 · App. 12/771,078 · Granted Sep 9, 2014

Temperature switchable adhesives comprising a crystallizable oil

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Quick Facts
Patent No.
US 8,828,181
App. No.
12/771,078
Granted
Sep 9, 2014
Kind
B2
Abstract

Temperature switchable adhesives formed by combining a pressure sensitive adhesive, which does not exhibit temperature switchable properties, with a crystallizable oil are described. These temperature switchable adhesives exhibit a sharp reduction in peel strength when the temperature is raised above the switching temperature. The adhesive properties of these adhesives may be readily tuned by adjusting the ratio of the elastomer, tackifier, and the crystallizable oil, and by choosing different crystallizable oils. The temperature switchable adhesives have use in medical, consumer, and industrial applications.

Claims (28)

1. A temperature switchable adhesive composition comprising:

a) at least one pressure sensitive adhesive, which does not exhibit temperature switchable properties, having a rubbery plateau between a first temperature T1 and a second temperature T2, said pressure sensitive adhesive comprising at least one elastomer selected from the group consisting of thermoplastic rubbers, natural rubbers, butyl rubbers, polyisobutylene polymers, vinyl ether polymers, ethylene/acrylic copolymers, silicone-based rubbers, and acrylics; and

b) at least one crystallizable oil having a crystalline melting point between T1 and T2 in an amount of at least about 20% by weight of the composition;

wherein the elastomer is an ABA block copolymer, wherein

a) A is a thermoplastic polystyrene end-block; and

b) B is a rubber mid-block selected from the group consisting of polyisoprene, polybutadiene, and poly(ethylene/butylene);

wherein the elastomer has a thermoplastic polystyrene end-block content of about 14% to about 30% by weight of the block copolymer; and wherein if the elastomer is selected from the group consisting of thermoplastic rubbers, natural rubbers, butyl rubbers, polyisobutylene polymers, vinyl ether polymers, ethylene/acrylic copolymers, and silicone-based rubbers, the pressure sensitive adhesive further comprises at least one tackifier.

2. The temperature switchable adhesive composition according to claim 1 , wherein the composition comprises a ratio of elastomer plus tackifier to crystallizable oil of about 0.66:1 to about 5.0:1 by weight.

3. The temperature switchable adhesive composition according to claim 1 , wherein the ABA block copolymer is a styrene-isoprene-styrene triblock copolymer having a styrene content of about 14% to about 22% by weight.

4. The temperature switchable adhesive composition according to claim 1 wherein the tackifier is selected from the group consisting of poly-β-pinene, abietic acid, abietic acid esters, hydrogenated abietic acid, hydrogenated abietic acid esters, poly-a-pinene, neoabietic acid, palustric acid, dihydroabietic acid, dehydroabietic acid, pimaric acid, isopimaric acid, styrene, methyl styrene, indene, methyl indene, oligomers of diclyopentadienes, and oligomers of butadienes.

5. The temperature switchable adhesive composition according to claim 4 wherein the tackifier is poly-β-pinene or abietic acid.

6. The temperature switchable adhesive composition according to claim 1 wherein the crystallizable oil is present in an amount of at least about 25% by weight of the composition.

7. The temperature switchable adhesive composition according to claim 1 wherein the crystallizable oil is selected from the group consisting of: hexadecane, 1-hexadecanol, 1-tetradecane, 1-tetradecanol, octadecane, and octadecanol.

8. The temperature switchable adhesive composition according to claim 1 wherein the elastomer is an acrylic and the pressure sensitive adhesive is self-tackifying.

9. A temperature switchable adhesive assembly comprising:

a) a backing; and

b) a coating comprising the temperature switchable adhesive composition of claim 1 .

10. The temperature switchable adhesive assembly according to claim 9 , wherein the backing is selected from the group consisting of: tapes, films of synthetic polymers, films of natural polymers, sheets of synthetic polymers, sheets of natural polymers, woven fabrics, nonwoven fabrics, and paper products.

11. The temperature switchable adhesive assembly according to claim 9 , wherein the assembly has a form selected from the group consisting of adhesive tapes, adhesive bandages, immobilization devices, wound dressings, transdermal delivery devices, EKG electrodes, masking tapes, stencils, envelopes, labels, stamps, wall paper, and floor tiles.

12. A method for imparting temperature switchable properties to a pressure sensitive adhesive, said method comprising the steps of:

a) providing at least one pressure sensitive adhesive, which does not exhibit temperature switchable properties, having a rubbery plateau between a first temperature T1 and a second temperature T2, said pressure sensitive adhesive comprising at least one elastomer selected from the group consisting of thermoplastic rubbers, natural rubbers, butyl rubbers, polyisobutylene polymers, vinyl ether polymers, ethylene/acrylic copolymers, silicone-based rubbers, and acrylics; and

b) mixing the at least one pressure sensitive adhesive with at least one crystallizable oil having a crystalline melting point between T1 and T2, wherein the crystallizable oil is in an amount of at least about 20% by weight;

wherein the elastomer is an ABA block copolymer, wherein

a) A is a thermoplastic polystyrene end-block; and

b) B is a rubber mid-block selected from the group consisting of polyisoprene, polybutadiene, and poly(ethylene/butylene);

wherein the elastomer has a thermoplastic polystyrene end-block content of about 14% to about 30% by weight of the block copolymer; and wherein if the elastomer is selected from the group consisting of thermoplastic rubbers, natural rubbers, butyl rubbers, polyisobutylene polymers, vinyl ether polymers, ethylene/acrylic copolymers, and silicone-based rubbers, the pressure sensitive adhesive further comprises at least one tackifier.

13. The method according to claim 12 wherein the pressure sensitive adhesive comprises a ratio of elastomer plus tackifier to crystallizable oil of about 0.66:1 to about 5.0:1 by weight.

14. The method according to claim 12 wherein the crystallizable oil is selected from the group consisting of hexadecane, 1-hexadecanol, 1-tetradecane, 1-tetradecanol, octadecane, and octadecanol.

Assignments (5)
CORRECTIVE ASSIGNMENT TO CORRECT THE DESIGNATION OF ASSIGNEE AS A DELAWARE CORPORATION TO A DELAWARE LIMITED LIABILITY COMPANY PREVIOUSLY RECORDED ON REEL 049880 FRAME 0001. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 28, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT US HOLDING, LLC
Reel/Frame 051502/0610 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT US HOLDING, LLC
Reel/Frame 049880/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 30, 2013
From: ACTAMAX SURGICAL MATERIALS LLC
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 029718/0579 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2011
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: ACTAMAX SURGICAL MATERIALS, LLC
Reel/Frame 026056/0539 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 9, 2010
From: BURCH, ROBERT RAY
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 024506/0896 →