Hydrogel compositions

• US 8,481,059 B2
• Filed: 06/24/2009
• Issued: 07/09/2013
• Est. Priority Date: 05/01/2001
• Status: Expired due to Term

• Current Assignee: Corium Pharma Solutions, Inc.
• Original Assignee: A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences,, Corium International, Inc.
• Inventors: Cleary, Gary W., Parandoosh, Shoreh, Feldstein, Mikhail M., Chalykh, Anatoly E., Plat, Nicolai A., Kulichikhin, Valery G.
• Primary Examiner(s): GHALI, ISIS A D
• Application Number:
  US12/491,088
• Publication Number:
  US 20090258060A1
• Time in Patent Office: 1,476 Days
• Field of Search: None
• US Class Current: 424/400
• CPC Class Codes: A61K 2800/262 Transparent; Translucent
• CPC Class Codes: A61K 2800/54 Polymers characterized by specific structures/properties
• CPC Class Codes: A61K 2800/5422 nonionic
• CPC Class Codes: A61K 2800/5424 anionic
• CPC Class Codes: A61K 8/0208 Tissues; Wipes; Patches
• CPC Class Codes: A61K 8/042 Gels
• CPC Class Codes: A61K 8/22 Peroxides; Oxygen; Ozone
• CPC Class Codes: A61K 8/73 Polysaccharides
• CPC Class Codes: A61K 8/731 Cellulose; Quaternized cellulose derivatives
• CPC Class Codes: A61K 8/8152 Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
• CPC Class Codes: A61K 8/817 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
• CPC Class Codes: A61K 8/8176 Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
• CPC Class Codes: A61K 8/86 Polyethers
• CPC Class Codes: A61L 15/24 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof A61L15/225 takes precedence
• CPC Class Codes: A61L 15/26 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof A61L15/225 takes precedence
• CPC Class Codes: A61L 15/28 Polysaccharides or their derivatives A61L15/225 takes precedence
• CPC Class Codes: A61L 15/44 Medicaments
• CPC Class Codes: A61L 15/58 Adhesives
• CPC Class Codes: A61L 15/60 Liquid-swellable gel-forming materials, e.g. super-absorbents
• CPC Class Codes: A61L 26/0052 Mixtures of macromolecular compounds
• CPC Class Codes: A61Q 11/00 : Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
• CPC Class Codes: B05D 5/00 : Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
• CPC Class Codes: C08L 53/00 : Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers

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

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.

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.

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.