IP Library Granted Patent US 8,728,445
Granted Patent B2
US 8,728,445 · App. 10/137,664 · Granted May 20, 2014

Hydrogel Compositions

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Quick Facts
Patent No.
US 8,728,445
App. No.
10/137,664
Granted
May 20, 2014
Kind
B2
Abstract

Hydrogel compositions are provided (a) that have a continuous hydrophobic phase and a discontinuous hydrophilic phase, (b) that have a discontinuous hydrophilic phase and a continuous hydrophilic phase, or (c) that are entirely composed of a continuous hydrophilic phase. The hydrophobic phase, if present, is composed of a hydrophobic polymer, particularly a hydrophobic pressure-sensitive adhesive (PSA), a plasticizing elastomer, a tackifying resin, and an optional antioxidant. The discontinuous hydrophilic phase, if present, is composed of a crosslinked hydrophilic polymer, particularly a crosslinked cellulosic polymer such as crosslinked sodium carboxymethylcellulose. For those hydrogel compositions containing a continuous hydrophilic phase, the components of the phase include a cellulose ester composition or an acrylate polymer or copolymer, and a blend of a hydrophilic polymer and a complementary oligomer capable of hydrogen bonding thereto. Films prepared from hydrogel compositions containing or entirely composed of the aforementioned continuous hydrophilic phase can be made translucent, and may be prepared using either melt extrusion or solution casting. A preferred use of the hydrogel compositions is in wound dressings, although numerous other uses are possible as well.

Claims (33)

1. A hydrogel composition entirely comprised of a single continuous hydrophilic phase, the composition comprising:

(a) a water-swellable acrylate copolymer comprising subunits selected from the group consisting of acrylic acid, methacrylic acid, methyl acrylate, ethyl acrylate, methyl methacrylate, and ethyl methacrylate; and

(b) a poly(N-vinyl lactam) in admixture with a complementary oligomer capable of hydrogen bonding thereto,

wherein the water-swellable acrylate copolymer represents 2 wt. % solids to 15 wt. % solids of the composition and has a ratio of free carboxyl groups to ester groups in a range of about 1:1 to 1:2.

2. The hydrogel composition of claim 1 , wherein the water-swellable acrylate copolymer is a methacrylic acid and methyl methacrylate copolymer.

3. The hydrogel composition of claim 1 , characterized by a water uptake of 400% to 1500% upon immersion in water.

4. The hydrogel composition of claim 1 , further comprising an active agent.

5. The hydrogel composition of claim 1 , wherein the composition is not covalently crosslinked.

6. The hydrogel composition of claim 4 , wherein the active agent is hydrogen peroxide.

7. The hydrogel composition of claim 1 , wherein the complementary oligomer represents 25 wt. % to 75 wt. % of the admixture.

8. The hydrogel composition of claim 1 , wherein the water-swellable acrylate copolymer represents between 4.91 wt. % solids and about 15 wt. % solids of the composition.

9. The hydrogel composition of claim 1 , wherein the water-swellable acrylate copolymer is a methacrylic acid-ethyl acrylate copolymer.

10. The hydrogel composition of claim 1 , wherein the poly(N-vinyl lactam) comprises monomer subunits selected from the group consisting of N-vinyl-2-pyrrolidone, N-vinyl-2-valerolactam, and N-vinyl-2-caprolactam.

11. The hydrogel composition of claim 10 , where the poly(N-vinyl lactam) is a non-crosslinked homopolymer.

12. The hydrogel composition of claim 10 , where the poly(N-vinyl lactam) is a non-crosslinked copolymer.

13. The hydrogel composition of claim 10 , wherein the poly(N-vinyl lactam) comprises monomers of N-vinyl-2-pyrrolidone.

14. The hydrogel composition of claim 13 , wherein the poly(N-vinyl lactam) is poly(vinylpyrrolidone).

15. The hydrogel composition of claim 10 , wherein the molecular weight of the poly(N-vinyl lactam) ranges from about 100,000 to about 1,500,000.

16. The hydrogel composition of claim 1 , wherein the complementary oligomer is selected from the group consisting of polyalcohols, oligoalkylene glycols, ether alcohols, and alkane-diols.

17. The hydrogel composition of claim 1 , wherein the complementary oligomer has a molecular weight ranging from about 45 to 600.

18. The hydrogel composition of claim 17 , wherein the complementary oligomer is a polyethylene glycol.

19. The hydrogel composition of claim 18 , wherein the polyethylene glycol has a molecular weight ranging from 300 to 600.

20. The hydrogel composition of claim 19 , wherein the polyethylene glycol is polyethylene glycol 400.

21. The hydrogel composition of claim 1 , capable of being reversibly dried.

22. The hydrogel composition of claim 4 , comprised within a monolithic delivery system.

23. The hydrogel composition of claim 1 , formed by melt extrusion.

24. The hydrogel composition of claim 1 cast upon a backing layer.

25. The hydrogel composition of claim 6 , comprising:

(a) 2 to 15 dry weight percent of a methacrylic acid-ethyl acrylate or a methacrylic acid-methyl methacrylate copolymer; and

(b) an admixture of poly(vinylpyrrolidone) and polyethylene glycol 400, wherein the polyethylene glycol 400 represents from 30 weight percent to 60 weight percent of the admixture.

26. The hydrogel composition of claim 25 comprised within a monolithic delivery system.

27. The hydrogel composition of claim 1 , wherein the water-swellable acrylate copolymer has a ratio of free carboxyl groups to ester groups of about 1:1.

28. The hydrogel composition of claim 1 , wherein the water-swellable acrylate copolymer has a ratio of free carboxyl groups to ester groups of about 1:2.

Assignments (14)
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jan 19, 2024
From: CORIUM, LLC
To: COLUMBUS INVESTMENT HOLDINGS SA
Reel/Frame 066355/0628 →
CHANGE OF NAME Recorded Oct 25, 2022
From: CORIUM, INC.
To: CORIUM, LLC
Reel/Frame 061852/0142 →
SECURITY INTEREST Recorded Sep 24, 2021
From: CORIUM, INC.
To: HERCULES CAPITAL, INC., AS AGENT
Reel/Frame 057597/0907 →
CHANGE OF NAME Recorded Apr 9, 2019
From: CORIUM INTERNATIONAL, INC.
To: CORIUM, INC.
Reel/Frame 048841/0324 →
RELEASE OF SECURITY INTEREST Recorded Mar 6, 2018
From: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "A" L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "B" (CAYMAN) L.P.; CAPITAL ROYALTY PARTNERS II (CAYMAN) L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 045513/0686 →
RELEASE OF SECURITY INTEREST Recorded Mar 6, 2018
From: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "A" L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "B" (CAYMAN) L.P.; CAPITAL ROYALTY PARTNERS II (CAYMAN) L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 046909/0855 →
RELEASE OF SECURITY INTEREST Recorded Nov 27, 2017
From: SILICON VALLEY BANK
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 044810/0026 →
RELEASE OF SECURITY INTEREST Recorded Nov 27, 2017
From: SILICON VALLEY BANK
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 044229/0054 →
SECURITY INTEREST Recorded Dec 4, 2014
From: CORIUM INTERNATIONAL, INC.
To: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II ? PARALLEL FUND ?A? L.P.; CAPITAL ROYALTY PARTNERS II ? PARALLEL FUND ?B? (CAYMAN) L.P.; CAPITAL ROYALTY PARTNERS II (CAYMAN) L.P.
Reel/Frame 034535/0238 →
SECURITY AGREEMENT Recorded Sep 10, 2012
From: CORIUM INTERNATIONAL, INC.
To: SILICON VALLEY BANK
Reel/Frame 028927/0365 →
SECURITY AGREEMENT Recorded Sep 4, 2012
From: CORIUM INTERNATIONAL, INC.
To: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "A" L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.
Reel/Frame 028895/0961 →
RELEASE OF SECURITY INTEREST Recorded Aug 30, 2012
From: OXFORD FINANCE LLC
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 028884/0179 →
SECURITY AGREEMENT Recorded Dec 20, 2011
From: CORIUM INTERNATIONAL, INC.
To: OXFORD FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 027422/0717 →
SECURITY AGREEMENT Recorded May 5, 2009
From: CORIUM INTERNATIONAL, INC.
To: SILICON VALLEY BANK
Reel/Frame 022634/0119 →