Water-soluble pressure sensitive adhesives

• US 8,968,772 B2
• Filed: 01/30/2013
• Issued: 03/03/2015
• Est. Priority Date: 04/28/2009
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Kantner, Steven S.
• Primary Examiner(s): Palenik, Jeffrey T
• Application Number:
  US13/753,958
• Publication Number:
  US 20130143991A1
• Time in Patent Office: 762 Days
• Field of Search: None
• US Class Current: 424/448
• CPC Class Codes: A61F 13/023 wound covering film layers without a fluid retention layer
• CPC Class Codes: A61F 2013/00642 soluble, e.g. in water
• CPC Class Codes: A61F 2013/00646 Medication patches, e.g. transcutaneous
• CPC Class Codes: A61F 2013/00659 polymeric base
• CPC Class Codes: A61F 2013/00868 thin film
• CPC Class Codes: A61L 15/585 Mixtures of macromolecular compounds
• CPC Class Codes: C08F 220/34 Esters containing nitrogen , e.g. N,N-dimethylaminoethyl (meth)acrylate
• CPC Class Codes: C08L 39/06 Homopolymers or copolymers of N-vinyl-pyrrolidones
• CPC Class Codes: C09J 133/14 of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C09J 139/06 Homopolymers or copolymers of N-vinyl-pyrrolidones
• CPC Class Codes: C09J 177/00 Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain based on polyhydrazides C09J179/06; based on polyamide-imides C09J179/08; Adhesives based on derivatives of such polymers

Abstract

A water-soluble pressure sensitive adhesive comprises a homogeneous blend comprising (a) a polymer selected from the group consisting of N-vinyl caprolactam homopolymers, N-vinyl pyrrolidone copolymers, and mixtures thereof and (b) a non-volatile plasticizer comprising a monohydric or polyhydric alcohol having hydrophilic-lipophilic balance of about 2 to about 10. The N-vinyl pyrrolidone copolymers comprise about 60% or less by weight N-vinyl pyrrolidone.

Claims

1. An adhesive comprising a homogeneous blend comprising:

(a) a polymer selected from the group consisting of N-vinyl caprolactam homopolymers, N-vinyl pyrrolidone copolymers, and mixtures thereof, the N-vinylpyrrolidone copolymers comprising about 60% or less by weight N-vinyl pyrrolidone; and

(b) a non-volatile plasticizer comprising a monohydric alcohol having hydrophilic-lipophilic balance of about 4 to about 9;

wherein the plasticizer comprises from about 33% to about 80% by weight of the adhesive such that the adhesive is pressure sensitive, water-soluble, and increases in weight less than about 15% after two days at 75% relative humidity and 40°

C.

2. The pressure sensitive adhesive of claim 1 wherein the polymer comprises from about 35% to about 75% by weight of the pressure sensitive adhesive.

3. The pressure sensitive adhesive of claim 1 wherein the polymer is an N-vinyl caprolactam homopolymers.

4. The pressure sensitive adhesive of claim 1 wherein the polymer is an N-vinyl pyrrolidone copolymer.

5. The pressure sensitive adhesive of claim 4, wherein the polymer is selected from the group consisting of N-vinyl caprolactam/N-vinyl pyrrolidone copolymers and vinyl acetate/N-vinyl pyrrolidone copolymers, the vinyl acetate/N-vinyl pyrrolidone copolymers comprising from about 20% to about 60% by weight N-vinyl pyrrolidone.

6. The pressure sensitive adhesive of claim 5, wherein the polymer is a copolymer of N-vinyl pyrrolidone and vinyl acetate comprising from about 30% to about 50% by weight N-vinyl pyrrolidone.

7. The pressure sensitive adhesive of claim 1 wherein the N-vinylpyrrolidone copolymers comprise about 30% or less by weight N-vinyl pyrrolidone.

8. The pressure sensitive adhesive of claim 1 wherein the polymer further comprises a comonomer in an amount up to about 10% by weight, the comonomer having no carboxylic acid functionality or tetraalkyl ammonium functionality.

9. The pressure sensitive adhesive of claim 1 wherein the plasticizer has a vapor pressure below about 0.1 mm Hg at 20°

C.

10. The pressure sensitive adhesive of claim 1 wherein the plasticizer is selected from the group consisting of polyether glycols having a carbon to oxygen mole ratio greater than about 2.5:

1, polyester polyols, C5-C10 alkyl diols, C4-C10 carboxylate monoesters of propylene glycol, C4-C10 carboxylate mono- and diesters of glycerin, C4-C10 alkyl monoethers of propylene glycol, C4-C10 alkyl mono- and diethers of glycerin, C4-C10 alkyl esters of lactic acid, C2-C4 triesters of citric acid, and mixtures thereof.

15. A device for skin contacting applications comprising a flexible backing and the pressure sensitive adhesive of claim 1 on at least a portion of the skin facing side of the flexible backing.

16. The device of claim 15 wherein the backing is water-soluble.

11. An adhesive comprising a homogeneous blend comprising:

(a) a polymer selected from the group consisting of N-vinyl caprolactam homopolymers, N-vinyl pyrrolidone copolymers, and mixtures thereof, the N-vinylpyrrolidone copolymers comprising about 60% or less by weight N-vinyl pyrrolidone; and

(b) a non-volatile plasticizer comprising a monohydric alcohol having hydrophilic-lipophilic balance of about 4 to about 9;

selected from the group consisting of C4-C10 monoesters and ethers of propylene glycol, C4-C10 diesters and ethers of glycerin, C4-C10 alkyl esters of lactic acid, C2-C4 triesters of citric acid, and mixtures thereof, wherein the plasticizer comprises from about 10% to about 80% by weight of the adhesive, such that the adhesive is pressure sensitive, water-soluble, and increases in weight less than about 15% after two days at 75% relative humidity and 40°

C.

12. The pressure sensitive adhesive of claim 11, wherein the polymer comprises from about 35% to about 75% by weight of the pressure sensitive adhesive.

13. The pressure sensitive adhesive of claim 11, wherein the polymer is an N-vinyl pyrrolidone copolymer.

14. The pressure sensitive adhesive of claim 11, wherein the pressure sensitive adhesive increases in weight less than about 10% after two days at 75% relative humidity and 40°

C.

17. A device for skin contacting applications comprising a flexible backing and the pressure sensitive adhesive of claim 11 on at least a portion of the skin facing side of the flexible backing, wherein the backing is water-soluble.

18. A method for removing a pressure sensitive adhesive from skin, the method comprising:

providing a device comprising a flexible backing and the pressure sensitive adhesive disposed on a least a portion of one side of the flexible backing, wherein the pressure sensitive adhesive comprises a homogeneous blend including (a) a polymer selected from the group consisting of N-vinyl caprolactam homopolymers, N-vinyl pyrrolidone copolymers, and mixtures thereof, the N-vinylpyrrolidone copolymers comprising about 60% or less by weight N-vinyl pyrrolidone; and

(b) a non-volatile plasticizer comprising a monohydric alcohol having hydrophilic-lipophilic balance of about 4 to about 9, wherein the plasticizer comprises from about 10% to about 80% by weight of the adhesive and the adhesive is pressure sensitive and water-soluble, and wherein the pressure sensitive adhesive increases in weight less than about 15% after two days at 75% relative humidity and 40°

C.;

dissolving the pressure sensitive adhesive in water;

and removing the backing.

19. The method of claim 18, wherein the backing is water soluble, and wherein removing the backing comprises dissolving the backing in water.