IP Library Granted Patent US 8,481,059
Granted Patent B2
US 8,481,059 · App. 12/491,088 · Granted Jul 9, 2013

Hydrogel compositions

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Quick Facts
Patent No.
US 8,481,059
App. No.
12/491,088
Granted
Jul 9, 2013
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 (23)

1. A hydrogel composition comprised of a single discontinuous hydrophobic phase and a discontinuous hydrophilic phase, wherein the discontinuous hydrophobic phase comprises (I) polyisobutylene, (II) a plasticizer, (iii) a tackifying resin, and (iv) an optional antioxidant, and the/discontinuous hydrophilic phase consists of one or more hydrophilic polymers.

2. The hydrogel composition of claim 1 , wherein the hydrophilic phase consists of a crosslinked hydrophilic polymer, and particles of the crosslinked hydrophilic polymer are dispersed in the hydrophobic phase.

3. The hydrogel composition of claim 2 , wherein the crosslinked hydrophilic polymer is a crosslinked cellulosic polymer.

4. The hydrogel composition of claim 3 , wherein the crosslinked cellulosic polymer is crosslinked sodium carboxymethylcellulose.

5. The hydrogel composition of claim 3 , wherein the crosslinked cellulosic polymer is selected from crosslinked sodium carboxymethylcellulose (CMC), crosslinked hydroxyethyl cellulose (HEC), and crosslinked partial free acid CMC.

6. The hydrogel composition of claim 1 , wherein the plasticizer is a low molecular weight plasticizer selected from the group consisting of dialkyl phthalates, dicycycloalkyl phthalates, diaryl phthalates, mixed alkyl-aryl phthalates, alkyl phosphates, aryl phosphates, alkyl citrates, citrate esters, alkyl adipates, dialkyl tartrates, dialkyl sebacates, dialkyl succinates, alkyl glycolates, alkyl glycerolates, glycol esters, glycerol esters, styrene-based copolymers, and mixtures thereof.

7. The hydrogel composition of claim 6 , wherein the low molecular weight plasticizer is selected from the group consisting of dimethyl phthalate, diethyl phthalate, dipropyl phthalate, di(2-ethylhexyl)phthalate, di-isopropyl phthalate, diamyl phthalate, dicapryl phthalate, tributyl phosphate, trioctyl phosphate, tricresyl phosphate, triphenyl phosphate, trimethyl citrate, triethyl citrate, tributyl citrate, acetyl triethyl citrate, trihexyl citrate, dioctyl adipate, diethyl adipate, di(2-methylethyl)adipate, dihexyl adipate, diethyl tartrate, dibutyl tartrate, diethyl sebacate, dipropyl sebacate, dinanyl sebacate, diethyl succinate, dibutyl succinate, glycerol diacetate, glycerol triacetate, glycerol monolactate diacetate, methyl phthalyl ethyl glycolate, butyl phthalyl butyl glycolate, ethylene glycol diacetate, ethylene glycol dibutyrate, triethylene glycol diacetate, triethylene glycol dibutyrate, triethylene glycol dipropionate, and mixtures thereof.

8. The hydrogel composition of claim 7 , wherein the low molecular weight plasticizer is dioctyl adipate.

9. The hydrogel composition of claim 1 , wherein the optional antioxidant is present In an amount of up to about 2% by weight.

10. The hydrogel composition of claim 9 , wherein the antioxidant is a sterically hindered phenol.

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

12. The hydrogel composition of claim 1 , further including at least one additive selected from the group consisting of fillers, preservatives, pH regulators, softeners, thickeners, pigments, dyes, refractive particles, stabilizers, toughening agents and detackifiers.

13. A method of forming a hydrogel, the method comprising:

mixing the components of a discontinuous hydrophobic phase comprising polyisobutylene, a plasticizing elastomer, a tackifying resin, and an optional antioxidant, with the components of a discontinuous hydropcophilic phase consisting of one or more hydrophilic polymers, to thereby form a hydrogel composition comprising a single discontinuous hydrophobic phase and a discontinuous hydrophilic phase.

14. The method of claim 13 , wherein the mixing is carried out at a temperature from about 90° C. to about 140° C.

15. The method of claim 14 , further comprising melt processing the components of the hydrophobic and hydrophilic phases through an extruder.

16. A melt-extruded hydrogel composition of claim 1 .

17. The hydrogel composition of claim 1 comprising about 5 weight percent to 15 weight percent polyisobutylene, based upon the composition in dry form.

18. The hydrogel composition of claim 1 , comprising from about 5 weight percent to about 15 weight percent tackifying resin, based upon the composition in dry form.

19. The hydrogel composition of claim 1 , wherein the weight ratio of tackifying resin to hydrophobic polymer ranges from 40:60 to 60:40.

20. The hydrogel composition of claim 2 , comprising about 25 weight percent to 65 weight percent crosslinked hydrophilic polymer, based upon the composition in dry form.

21. The hydrogel composition of claim 1 , comprising from about 25 weight percent to 40 weight percent plasticizer after drying.

22. The hydrogel composition of claim 1 , comprising from about 5 weight percent to 15 weight percent polyisobutylene, from about 25 weight percent to 65 weight percent hydrophilic polymer, from about 25 weight percent to 40 weight percent plasticizer, and from about 5 weight percent to about 15 weight percent tackifying resin, based upon the composition in dry form.

Assignments (14)
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER PREVIOUSLY RECORDED AT REEL: 61852 FRAME: 207. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 30, 2025
From: CORIUM, INC.
To: CORIUM PHARMA SOLUTIONS, INC.
Reel/Frame 071915/0691 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2022
From: CORIUM, INC.
To: CORIUM PHARMA SOLUTIONS, INC.
Reel/Frame 062760/0731 →
RELEASE OF SECURITY INTEREST Recorded Oct 19, 2022
From: HERCULES CAPITAL, INC., AS AGENT
To: CORIUM, INC.
Reel/Frame 061713/0557 →
RELEASE OF SECURITY INTEREST Recorded Oct 17, 2022
From: HERCULES CAPITAL, INC.
To: CORIUM, INC.
Reel/Frame 061687/0281 →
SECURITY INTEREST Recorded Oct 17, 2022
From: CORIUM PHARMA SOLUTIONS, INC.
To: SILICON VALLEY BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 061689/0581 →
CHANGE OF NAME Recorded Oct 14, 2022
From: CORIUM, INC.
To: CORIUM PHARMA SOLUTIONS, INC.
Reel/Frame 061852/0207 →
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 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 →