Water-absorbent adhesive compositions and associated methods of manufacture and use

• US 9,127,140 B2
• Filed: 12/23/2013
• Issued: 09/08/2015
• Est. Priority Date: 05/01/2001
• Status: Expired due to Fees

• Current Assignee: Corium LLC
• Original Assignee: A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences,, Corium International, Inc.
• Inventors: Feldstein, Mikhail M., Bayramov, Danir F., Novikov, Mikhail Borisovich, Kulichikhin, Valery G., Plat, Nicolai A., Cleary, Gary W., Singh, Parminder
• Primary Examiner(s): Yoon, Tae H
• Application Number:
  US14/139,530
• Publication Number:
  US 20140322143A1
• Time in Patent Office: 624 Days
• Field of Search: 427/208, 264/177.17, 424/613, 523/118
• US Class Current: 1/1
• CPC Class Codes: A61K 2800/262 Transparent; Translucent
• CPC Class Codes: A61K 2800/54 Polymers characterized by specific structures/properties
• CPC Class Codes: A61K 47/32 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers , poly(meth)acrylates, or polyvinyl pyrrolidone
• CPC Class Codes: A61K 8/042 Gels
• 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 8/8176 Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
• CPC Class Codes: A61K 8/8182 Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
• CPC Class Codes: A61K 8/86 Polyethers
• CPC Class Codes: A61L 15/42 Use of materials characterised by their function or physical properties liquid bandages A61L26/00
• CPC Class Codes: A61L 15/585 Mixtures of macromolecular compounds
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• 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 5/10 to obtain an adhesive surface
• CPC Class Codes: C08K 5/06 Ethers; Acetals; Ketals; Ortho-esters
• CPC Class Codes: C08K 5/11 of acyclic polycarboxylic acids
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 33/04 Homopolymers or copolymers of esters C08L43/04 takes precedence
• CPC Class Codes: C08L 39/06 Homopolymers or copolymers of N-vinyl-pyrrolidones
• CPC Class Codes: C08L 71/02 Polyalkylene oxides
• CPC Class Codes: C09J 133/14 of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen

Abstract

An adhesive composition is provided that is water-insoluble yet water-absorbent, i.e., capable of absorbing up to 15 wt. % water or more. The composition in composed of a film-forming hydrophilic polymer with at least one linear segment having a plurality of recurring polar groups along the polymer backbone, a complementary multifunctional polymer with a plurality of recurring functional groups that non-covalently bind to the polar groups on the film-forming polymer, and plasticizer. A method for manufacturing the adhesive composition is provided as well.

Claims

1. A method for preparing a water-insoluble, water-absorbent adhesive composition effective to adhere to moist surfaces, the method comprising:

(a) combining, under conditions effective to form a substantially homogeneous admixture;

a film-forming, hydrophilic polymer (FFHP) containing a plurality of recurring polar groups, wherein the FFHP is a poly(N-vinyl lactam) or an acrylate polymer or copolymer comprising recurring amino groups,

a complementary multifunctional polymer (CMP) containing a plurality of recurring carboxyl proton-donating functional groups, wherein the CMP is an acrylate polymer or copolymer having a molecular weight lower than the molecular weight of the FFHP, and wherein functional groups contained in the CMP are capable of non-covalently binding to recurring polar groups in the FFHP; and

a relatively low molecular weight plasticizer capable of plasticizing the FFHP, the plasticizer selected from the group consisting of polyethylene glycols and polyalchols having a molecular weight in a range from about 45 to about 600 daltons, and mixtures thereof;

the improvement comprising;

(b) choosing a weight fraction amount of the FFHP that is greater than the weight fraction amount of the CMP,

(c) adding to the admixture, or to the FFHP or CMP prior to the combining step, an ionizing agent in an amount effective to ionize up to about 30% of the ionogenic groups in the admixture, or in the FFHP and/or CMP respectively,

(d) blending the resulting admixture, and

(e) extruding;

wherein the resulting extruded adhesive composition displays an adhesion that is enhanced over the adhesion for the same composition absent the ionizing agent.

2. The method of claim 1, wherein the resulting extruded adhesive composition is generally substantially non-tacky prior to contact with water, and becomes tacky upon contact with a moist surface.

3. The method of claim 1, further comprising combining at least one optional additive with the FFHP, the CMP, and the plasticizer during formation of the admixture.

4. The method of claim 3, wherein the at least one optional additive is selected from the group consisting of fillers, pH regulating agents, tackifiers, detackifying agents, electrolytes, antimicrobial agents, antioxidants, preservatives, colorants, flavorants, and combinations thereof.

5. The method of claim 1, further comprising combining a pharmacologically or a cosmeceutically active agent with the FFHP, the CMP, and the plasticizer during formation of the admixture.

6. The method of claim 5, wherein the pharmacologically or cosmeceutically active agent is a tooth whitening agent.

7. The method of claim 1, further comprising the addition of water or solvent in the combining step.

8. The method of claim 1, wherein the extruding step comprises extruding the admixture directly onto a backing member.

9. The method of claim 1, wherein the extruded adhesive composition from step (e) is pressed against a backing member.

10. The method of claim 8, further comprising adding a release liner to the admixture that has been extruded onto the backing member.

11. The method of claim 1, where the ionizing agent is an acid or a base.

12. The method of claim 9, wherein the base is inorganic.

13. The method of claim 12, wherein the base is selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, and ammonium carbonate.

14. The method of claim 1, wherein the poly(N-vinyl lactam) is selected from poly(vinyl pyrrolidone), poly(vinyl-2-valerolactam) and poly(N-vinyl-2-caprolactam).

15. The method of claim 1, wherein the poly(N-vinyl lactam) is poly(N-vinyl-2-pyrrolidone).

16. The method of claim 1, wherein the relatively low molecular weight plasticizer is a polyethylene glycol.

17. The method of claim 1, wherein the polyethylene glycol has a molecular weight in a range of about 300-600 daltons.

18. The method of claim 1, wherein the relatively low molecular weight plasticizer is a polyethylene glycol and the FFHP is poly(N-vinyl-2-pyrrolidone).

19. The method of claim 1, wherein the molecular weight of the FFHP is in the range of approximately 100,000 to 2,000,000 Da.

20. The method of claim 1, wherein weight fraction amount of the FFHP in the water-insoluble, water-absorbent adhesive composition ranges from 20 to 95 weight percent.

21. The method of claim 1, wherein the ionizing agent is added in an amount effective to ionize from about 5% to 10% of the ionogenic groups in the admixture, or in the FFHP and/or CMP respectively.

22. The method of claim 1, wherein the ionizing agent is added in an amount effective to ionize from about 5% to 10% of the ionogenic groups present in the film-forming polymer.