Pyrrolidonoethyl (meth)acrylate containing pressure sensitive adhesive compositions

• US 6,902,740 B2
• Filed: 07/09/2001
• Issued: 06/07/2005
• Est. Priority Date: 07/09/2001
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Duan, Daniel C., Schaberg, Mark S., Pournoor, Kaveh
• Primary Examiner(s): Page, Thurman K.
• Assistant Examiner(s): GHALI, ISIS A D
• Application Number:
  US09/901,219
• Publication Number:
  US 20030113365A1
• Time in Patent Office: 1,429 Days
• Field of Search: 424/448, 424/449, 424/443
• US Class Current: 424/448
• CPC Class Codes: A61K 9/7053 obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
• CPC Class Codes: A61K 9/7061 Polyacrylates
• CPC Class Codes: C09J 133/062 Copolymers with monomers not covered by C09J133/06
• CPC Class Codes: C09J 2301/302 the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C

Abstract

The present invention relates to a pressure sensitive adhesive composition comprising a copolymer comprising pyrrolidonoethyl acrylate or pyrrolidonoethyl methacrylate. This composition may be used as part of a transdermal drug delivery device.

Claims

1. A pressure sensitive adhesive composition comprising a copolymer comprising

(a) at least one A monomer selected from the group consisting of an alkyl acrylate containing 4 to 12 carbon atoms in the alkyl group and an alkyl methacrylate containing 4 to 12 carbon atoms in the alkyl group;

and

(b) pyrrolidonoethyl acrylate.

2. The composition of claim 1 wherein the A monomer is selected from the group consisting of isooctyl acrylate, 2-ethylhexyl acrylate, butyl acrylate, and cyclohexyl acrylate.

3. The composition of claim 1 wherein the A monomer is isooctyl acrylate.

4. The composition of claim 1 further comprising a B monomer that is copolymerizable with the A and pyrrolidoethyl acrylate.

5. The composition of claim 4 wherein the B monomer comprises a functional group selected from the group consisting of carboxylic acid, carboxylic acid ester, sulfonamide, urea, carbamate, carboxamide, hydroxy, amine, oxy, oxo, and cyano.

6. The composition of claim 1 wherein the copolymer further comprises a macromonomer.

7. The composition of claim 6 wherein the macromonomer is a functionally terminated polymethylmethacrylate.

8. The composition of claim 6 further comprising a drug in an amount such that the composition delivers a therapeutically effective amount for the indication being treated.

9. The composition of claim 8 wherein the copolymer contains from about 1% to about 6% of macromonomer by weight.

10. The composition of claim 9 wherein the copolymer contains from about 10% to about 45% of pyrrolidonoethyl acrylate by weight.

11. The composition of claim 10 wherein the copolymer further comprises vinyl acetate.

12. The composition of claim 10 further comprising a softener wherein the concentration of softener is from about 10% to about 40% based on the total weight of the composition.

13. The composition of claim 1 further comprising a drug in an amount such that the composition delivers a therapeutically effective amount for the indication being treated.

14. The composition of claim 1 further comprising a softener.

15. The composition of claim 14 wherein the softener is selected from the group consisting of a C₈-C₃₆ fatty acid;

a C₈-C₃₆ fatty alcohol;

a lower alkyl ester of a C₈-C₃₆ fatty acid;

a di(lower) alkyl ester of a C₆-C₈ diacid;

a monoglyceride of a C₈-C₃₆ fatty acid;

tetraglycol;

tetraethylene glycol;

a C₆-C₃₆ alkyl pyrrolidone carboxylate;

a polyethylene glycol;

propylene glycol;

2-(2-ethoxyethoxy)ethanol;

diethylene glycol monomethyl ether;

N,N-dimethyldodecylamine N-oxide; and

combinations of any two or more of the foregoing.

16. The composition of claim 14 wherein the concentration of softener is from about 10% to about 40% based on the total weight of the composition.

17. The composition of claim 1 further comprising an anti-microbial agent.

18. The composition of claim 17 wherein the anti-microbial agent is selected from the group consisting of chlorhexidine, a chlorhexidine salt, and mixtures thereof.

19. The composition of claim 17 wherein the anti-microbial agent is selected from the group consisting of iodine, iodine complexes with sodium or potassium iodine, and mixtures thereof.

20. The composition of claim 17 wherein the copolymer contains from about 5% to about 15% of pyrrolidonoethyl acrylate by weight.

21. The composition of claim 20 wherein the anti-microbial agent is selected from the group consisting of chlorhexidine, a chlorhexidine salt, and mixtures thereof.

22. The composition of claim 20 wherein the anti-microbial agent is selected from the group consisting of iodine, iodine complexes with sodium or potassium iodide, and mixtures thereof.

23. A transdermal delivery device comprising a backing and a composition according to claim 8, the composition being coated on at least a portion of a surface of the backing.

24. A transdermal drug delivery device comprising a backing and a composition according to claim 12, the composition being coated on at least a portion of a surface of the backing.

25. A transdermal drug delivery device comprising a backing and a composition according to claim 13, the composition being coated on at least a portion of a surface of the backing.

27. A pressure sensitive tape comprising a backing and a composition according to claim 1, the composition being coated on at least a portion of a surface of the backing.

29. The composition of claim 1 wherein the A monomer contains from about 40% to about 95% by weight.

26. A method for transdermal delivery of a drug comprising the steps of

(A) a step of providing a composition comprising

(i) a copolymer comprising

(a) at least one A monomer selected from the group consisting of an alkyl acrylate containing 4 to 12 carbon atoms in the alkyl group and an alkyl methacrylate containing 4 to 12 carbon atoms in the alkyl group;

and

(b) pyrrolidonoethyl acrylate; and

(ii) a drug in an amount such that the composition delivers a therapeutically effective amount for the indication being treated; and

(B) a step of applying the composition to an external part of the human body for a period sufficient to achieve the desired therapeutic result.

28. A pressure sensitive adhesive copolymer comprising

(a) at least one A monomer selected from the group consisting of an alkyl acrylate containing 4 to 12 carbon atoms in the alkyl group and an alkyl methacrylate containing 4 to 12 carbon atoms in the alkyl group;

and

(b) pyrrolidonoethyl acrylate.