Two-phase, water-absorbent bioadhesive composition

• US 20030130427A1
• Filed: 05/01/2002
• Published: 07/10/2003
• Est. Priority Date: 05/01/2001
• Status: Active Grant

• Current Assignee: A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences,, Corium, Inc.
• Original Assignee: Corium International, Inc.
• Inventors: Cleary, Gary W., Feldstein, Mikhail M., Bairamov, Danir F., Kulichikhin, Valery G.
• Granted Patent: US 6,803,420 B2
• Time in Patent Office: Days
• US Class Current: 525/192
• CPC Class Codes: A61K 9/7053 obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
• CPC Class Codes: A61L 15/44 Medicaments
• CPC Class Codes: A61L 15/46 Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
• CPC Class Codes: A61L 15/585 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 15/60 Liquid-swellable gel-forming materials, e.g. super-absorbents
• CPC Class Codes: C08L 23/22 Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefins
• CPC Class Codes: C08L 2312/00 Crosslinking
• CPC Class Codes: C08L 2666/20 Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 71/00 Compositions of polyethers obtained by reactions forming an ether link in the main chain of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 77/00 Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain of polyhydrazides C08L79/06; of polyamideimides or polyamide acids C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C09J 123/22 Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefines

Abstract

An adhesive composition is provided that contains both a hydrophobic phase and a hydrophilic phase, wherein the hydrophobic phase is composed of a crosslinked hydrophobic polymer composition and the hydrophilic phase is a water-absorbent blend of a hydrophilic polymer and a complementary oligomer capable of crosslinking the hydrophilic polymer through hydrogen bonding, ionic bonding, and/or covalent bonding. The composition is useful as a bioadhesive, for affixing drug delivery systems, wound dressings, bandages, cushions, or the like to a body surface such as skin or mucosal tissue.

Claims

1. A bioadhesive composition comprising a hydrophobic phase and a hydrophilic phase, wherein the hydrophobic phase comprises a crosslinked hydrophobic polymer composition and the hydrophilic phase comprises a mixture of a hydrophilic polymer and a complementary oligomer capable of crosslinking the hydrophilic polymer through hydrogen bonding, ionically bonding, or covalently

2. The composition of claim 1, wherein the crosslinked hydrophobic polymer composition is a crosslinked butyl rubber.

3. The composition of claim 2, wherein the crosslinked hydrophobic polymer composition is butyl rubber crosslinked with polyisobutylene.

4. The composition of claim 1, wherein the hydrophilic polymer and the complementary oligomer are covalently crosslinked.

5. The composition of claim 1, wherein the hydrophilic polymer is selected from the group consisting of poly(N-vinyl lactams), poly(N-vinyl amides), poly(N-alkylacrylamides), polyacrylic acid, polymethacrylic acid, polyvinyl alcohol, polyvinylamine, and copolymers and blends thereof.

6. The composition of claim 5, wherein the hydrophilic polymer is selected from the group consisting of poly(N-vinyl lactams), poly(N-vinyl amides), poly(N-alkylacrylamides), and copolymers and blends thereof.

7. The composition of claim 6, wherein the hydrophilic polymer is a poly(N-vinyl lactam).

8. The composition of claim 7, wherein the hydrophilic polymer is a poly(N-vinyl lactam) homopolymer.

9. The composition of claim 8, wherein the poly(N-vinyl lactam) is selected from the group consisting of polyvinyl pyrrolidone, polyvinyl caprolactam, and blends thereof.

10. The composition of claim 9, wherein the poly(N-vinyl lactam) is polyvinyl pyrrolidone.

11. The composition of claim 9, wherein the poly(N-vinyl lactam) is polyvinyl caprolactam.

12. The composition of claim 1, wherein the hydrophilic polymer has a number average molecular weight in the range of approximately 20,000 to 2,000,000.

13. The composition of claim 12, wherein the hydrophilic polymer has a number average molecular weight in the range of approximately 200,000 to 1,000,000.

14. The composition of claim 1, wherein the complementary oligomer has a molecular weight in the range of about 45 to 800.

15. The composition of claim 14, wherein the complementary oligomer has a molecular weight in the range of about 45 to 600.

16. The composition of claim 15, wherein the complementary oligomer has a molecular weight in the range of about 300 to 600.

17. The composition of claim 1, wherein the complementary oligomer is selected from the group consisting of polyalcohols, monomeric and oligomeric alkylene glycols, polyalkylene glycols, carboxyl-teminated polyalkylene glycols, amino-terminated polyalkylene glycols, ether alcohols, alkane diols and carbonic diacids.

18. The composition of claim 17, wherein the complementary oligomer is selected from the group consisting of polyalkylene glycols and carboxyl-terminated polyalkylene glycols.

19. The hydrogel composition of claim 18, wherein the complementary oligomer is selected from the group consisting of polyethylene glycol and carboxyl-terminated polyethylene glycol.

20. The composition of claim 19, wherein the complementary oligomer is polyethylene glycol.

21. The composition of claim 20, wherein the complementary oligomer is polyethylene glycol 400.

22. The composition of claim 1, further including an active agent.

23. A method for preparing a two-phase, water-absorbent bioadhesive composition comprising:

(a) preparing a crosslinkable hydrophobic composition comprised of a hydrophobic polymer and at least one agent effective to crosslink the polymer; and

(b) preparing a hydrophilic composition comprised of a hydrophilic polymer and a complementary oligomer capable of crosslinking the hydrophilic polymer through hydrogen bonding, ionic bonding, and/or covalent bonding;

(c) admixing the crosslinkable hydrophobic composition with the hydrophilic composition; and

(d) crosslinking the hydrophobic polymer in the admixture.

24. The method of claim 23, wherein the complementary oligomer is effective to crosslink the hydrophilic polymer in the presence of a curing agent.

25. The method of claim 24, wherein (d) further includes crosslinking the hydrophilic polymer.

26. The method of claim 25, wherein (d) is carried out at a temperature effective to thermally crosslink both the hydrophobic polymer and the hydrophilic polymer.

27. The method of claim 26, wherein the hydrophobic polymer is butyl rubber and the at least one agent comprises polyisobutylene.

28. The method of claim 27, wherein the at least one agent additionally comprises an organic peroxide.

29. The method of claim 26, wherein the curing agent is pentaerythritol monohydroxypentaacrylate.