CA2415076A1 - Preparation of hydrophilic pressure sensitive adhesives having optimized adhesive properties - Google Patents

Preparation of hydrophilic pressure sensitive adhesives having optimized adhesive properties Download PDF

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Publication number
CA2415076A1
CA2415076A1 CA002415076A CA2415076A CA2415076A1 CA 2415076 A1 CA2415076 A1 CA 2415076A1 CA 002415076 A CA002415076 A CA 002415076A CA 2415076 A CA2415076 A CA 2415076A CA 2415076 A1 CA2415076 A1 CA 2415076A1
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CA
Canada
Prior art keywords
composition
hydrophilic polymer
poly
plasticizing agent
plasticizer
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Granted
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CA002415076A
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French (fr)
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CA2415076C (en
Inventor
Mikhail M. Feldstein
Nicolai A. Plate
Anatoly E. Chalykh
Gary W. Cleary
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AV Topchiev Institute of Petrochemical Synthesis
Corium LLC
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Individual
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/58—Adhesives

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Hematology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Medicinal Preparation (AREA)
  • Materials For Medical Uses (AREA)

Abstract

A method for preparing hydrophilic pressure sensitive adhesive (PSA) compositions is provided, wherein the method enables preparation of adhesives having a particular, optimized degree of adhesion. That is, the hydrophilic PSA is comprised of a hydrophilic polymer and a complementary short-chain plasticizing agent, wherein the hydrophilic polymer and plasticizing agent are capable of hydrogen bonding or electrostatic bonding to each other and are present in a ratio that optimizes key characteristics of the adhesive composition, such as adhesive strength, cohesive strength and hydrophilicity. The adhesive is useful in a wide variety of contexts, e.g., as a biomedical adhesive for application to the skin or other body surface, and as such finds utility in the areas of drug delivery systems (e.g., topical, transdermal, transmucosal, iontophoretic), medical skin coverings and wound healing products and biomedical electrodes.

Claims (58)

1. A method of preparing an adhesive composition having an optimized degree of adhesion, comprising:
(a) preparing a plurality of compositions each comprised of a hydrophilic polymer having a glass transition temperature Tg pol admixed with a plasticizer miscible therewith and having a glass transition temperature Tg pl and capable of covalently or noncovalently crosslinking the hydrophilic polymer, wherein the weight fraction of the hydrophilic polymer in each composition is w pol, and the weight fraction of the plasticizer in each composition is w pl;
(b) calculating predicted glass temperatures Tg predicted for each composition using the Fox equation (1) (1) and plotting Tg predicted versus w pl for each composition;
(c) determining the glass transition temperature Tg actual for each composition, and plotting Tg actual versus w pl for each composition;
(d) identifying the region of the plots of (b) and (c) wherein Tg actual is less than Tg predicted; such that there is a negative deviation from Tg predicted;
(e) within the region identified in (d), identifying the optimum weight fraction of plasticizer w pl optimum at which the negative deviation from Tg predicted is at a maximum; and (f) admixing a monomeric precursor to the hydrophilic polymer and the plasticizer under polymerizing conditions to provide an adhesive composition having an optimized degree of adhesion, wherein the weight fraction of plasticizer in the composition is w pl optimum, and the weight fraction of the hydrophilic polymer in the composition is 1-w pl optimum
2. A method of preparing an adhesive composition having an optimized degree of adhesion, comprising:
(a) preparing a plurality of compositions each comprised of a hydrophilic polymer having a glass transition temperature Tg pol admixed with a plasticizer miscible therewith and having a glass transition temperature Tg pl and capable of covalently or noncovalently crosslinking the hydrophilic polymer, wherein the weight fraction of the hydrophilic polymer in each composition is w pol, and the weight fraction of the plasticizer in each composition is w pl, such that w pol is equal to 1-w pl;
(b) calculating predicted glass temperatures Tg predicted for each composition using the Fox equation (1) (1) and plotting Tg predicted versus w pl for each composition;
(c) determining the glass transition temperature Tg actual for each composition, and plotting Tg actual versus w pl for each composition;
(d) identifying the region of the plots of (b) and (c) wherein Tg actual has a predetermined deviation from Tg predicted; and (e) admixing a monomeric precursor to the hydrophilic polymer and the plasticizer under polymerizing conditions to provide an adhesive composition having a desired degree of adhesion, wherein the weight percent of plasticizer in the composition corresponds to a value within the region identified in section (d).
3. The method of claim 1 or claim 2, wherein the plasticizer is capable of covalently crosslinking the hydrophilic polymer.
4. The method of claim 3, wherein the plasticizer is capable of noncovalently crosslinking the hydrophilic polymer.
5. The method of claim 4, wherein the plasticizer is capable of crosslinking the hydrophilic polymer by hydrogen bonding thereto.
6. The method of claim 1 or claim 2, wherein the difference between Tg pol and Tg pl is at least about 50°C, such that Tg actual for each composition is determined solely by Tg pl.
7. The method of claim 1 or claim 2, 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.
8. The method of claim 7, 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.
9. The method of claim 8, wherein the hydrophilic polymer is a poly(N-vinyl lactam).
10. The method of claim 9, wherein the hydrophilic polymer is a poly(N-vinyl lactam) homopolymer.
11. The method of claim 10, wherein the poly(N-vinyl lactam) is selected from the group consisting of polyvinyl pyrrolidone, polyvinyl caprolactam, and blends thereof.
12. The method of claim11, wherein the poly(N-vinyl lactam) is polyvinyl pyrrolidone.
13. The method of claim 11, wherein the poly(N-vinyl lactam) is polyvinyl caprolactam.
14. The method of claim 1 or claim 2, wherein the hydrophilic polymer has a weight average molecular weight in the range of approximately 100,000 to 2,000,000.
15. The method of claim 14, wherein the hydrophilic polymer has a weight average molecular weight in the range of approximately 500,000 to 1,500,000.
16. The method of claim 1 or claim 2, wherein Tg pl is in the range of approximately -100° to -30°C.
17. The method of claim 1 or claim 2, wherein the melting temperature of the plasticizer is lower than about 50°C.
18. The method of claim 1 or claim 2, wherein the plasticizing agent has a molecular weight in the range of about 45 to 800.
19 The method of claim 18, wherein the plasticizing agent has a molecular weight in the range of about 45 to 600.
20. The method of claim 19, wherein the plasticizing agent has a molecular weight in the range of about 300 to 600.
21. The method of claim 1 or claim 2, wherein the plasticizing agent is selected from the group consisting of of polyalcohols, monomeric and oligomeric alkylene glycols, polyalkylene glycols, carboxyl-teminated polyalkylene glycols, amino-terminated polyalkylene glycols, ether alcohols, alkane diols and carbonic diacids.
22. The method of claim 21, wherein the plasticizing agent is selected from the group consisting of polyalkylene glycols and carboxyl-terminated polyalkylene glycols.
23. The method of claim 22, wherein the plasticizing agent is selected from the group consisting of polyethylene glycol and carboxyl-terminated polyethylene glycol.
24. The method of claim 23, wherein the plasticizing agent is polyethylene glycol.
25. The method of claim 1 or claim 2, wherein the adhesive composition further includes a photoinitator, and, following step (e), the adhesive composition is crosslinked using radiation.
26. The method of claim 1 or claim 2, wherein step (e) further includes admixing the hydrophilic polymer and the plasticizing agent with at least one chemical crosslinking agent that covalently crosslinks the adhesive composition.
27. The method of claim 26, wherein the at least one chemical crosslinking agent is selected from the group consisting of dipentaerythritol pentaacrylate, ethylene glycol dimethacrylate, and triethylene glycol dimethacrylate.
28. The method of claim 27, wherein the weight ratio of the chemical crosslinking agent to the hydrophilic polymer is below 5 %.
29. The method of claim 1, wherein, following admixture of the monomeric precursor to the hydrophilic polymer and the plasticizer under polymerizing conditions, the resulting adhesive composition is crosslinked using heat.
30. The method of any one of claims 25-29, wherein the crosslinking density of the crosslinked adhesive composition provides a swell ratio in the range of approximately 20 to approximately 60.
31. A hydrophilic pressure sensitive adhesive composition comprising (a) a hydrophilic polymer having a glass transition temperature Tg pol, and (b) a complementary hydroxyl-terminated or carboxyl-terminated short-chain plasticizing agent having a glass transition temperature Tg pl and capable of hydrogen bonding or electrostatic bonding to the hydrophilic polymer, wherein the weight ratio of hydrophilic polymer to complementary short-chain plasticizing agent is selected so to provide a predetermined deviation in (a) the actual glass transition temperature Tg actual of the composition from (b) the predicted glass transition temperature Tg predicted calculated for the composition using the Fox equation.
32. The composition of claim 31, wherein the predetermined deviation is the maximum negative deviation.
33. The composition of claim 31 or claim 32, wherein the adhesive composition is substantially nonaqueous.
34. The composition of claim 31, wherein the difference between Tg pol and Tg pl is at least about 50°C, such that Tg actual for each composition is determined solely by Tg pl.
35. The composition of claim 31, 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.
36. The composition of claim 35, 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.
37. The composition of claim 36, wherein the hydrophilic polymer is a poly(N-vinyl lactam).
38. The composition of claim 37, wherein the hydrophilic polymer is a poly(N-vinyl lactam) homopolymer.
39. The composition of claim 38, wherein the poly(N-vinyl lactam) is selected from the group consisting of polyvinyl pyrrolidone, polyvinyl caprolactam, and blends thereof.
40. The composition of claim 39, wherein the poly(N-vinyl lactam) is polyvinyl pyrrolidone.
41. The composition of claim 39, wherein the poly(N-vinyl lactam) is polyvinyl caprolactone.
42. The composition of claim 31, wherein the hydrophilic polymer has a weight average molecular weight in the range of approximately 100,000 to 2,000,000.
43. The composition of claim 42, wherein the hydrophilic polymer has a weight average molecular weight in the range of approximately 500,000 to 1,500,000.
44. The composition of claim 31, wherein Tg pl is in the range of approximately -100° to -30°C.
45. The composition of claim 31, wherein the melting temperature of the plasticizer is lower than about 50°C.
46. The composition of claim 31, wherein the plasticizing agent has a molecular weight in the range of about 45 to 800.
47. The composition of claim 46, wherein the plasticizing agent has a molecular weight in the range of about 45 to 600.
48. The composition of claim 47, wherein the plasticizing agent has a molecular weight in the range of about 300 to 600.
49. The composition of claim 31, wherein the plasticizing agent is selected from the group consisting of of polyalcohols, monomeric and oligomeric alkylene glycols, polyalkylene glycols, carboxyl-teminated polyalkylene glycols, amino-terminated polyalkylene glycols, ether alcohols, alkane diols and carbonic diacids.
50. The composition of claim 49, wherein the plasticizing agent is selected from the group consisting of polyalkylene glycols and carboxyl-terminated polyalkylene glycols.
51. The composition of claim 50, wherein the plasticizing agent is selected from the group consisting of polyethylene glycol and carboxyl-terminated polyethylene glycol.
52. The composition of claim 51, wherein the plasticizing agent is polyethylene glycol.
53. The composition of claim 31, wherein the composition is covalently crosslinked.
54. The composition of claim 53, wherein the crosslinking density of the crosslinked adhesive composition provides a swell ratio in the range of approximately 20 to approximately 60.
55. A substantially nonaqueous hydrophilic pressure sensitive adhesive composition comprising (a) a hydrophilic polymer and (b) a complementary hydroxyl-terminated or carboxyl-terminated short-chain plasticizing agent capable of hydrogen bonding or electrostatic bonding to the hydrophilic polymer, wherein the hydrophilic polymer and the plasticizing agent are crosslinked to a predetermined extent, and further wherein the extent of crosslinking and the ratio of the hydrophilic polymer to the plasticizing agent are selected to optimize the hydrophilicity, adhesive strength and cohesive strength of the composition.
56. A therapeutic system for the topical or transdermal administration of a pharmacologically active agent, comprising:
(A) a drug reservoir comprised of the adhesive composition of any one of claims 31-50; and (B) a backing layer laminated to the drug reservoir that serves as the outer surface of the device during use.
57. The system of claim 56, wherein the backing layer is non-occlusive.
58. The system of claim 59, wherein the backing layer is occlusive.
CA2415076A 2000-07-07 2001-07-06 Preparation of hydrophilic pressure sensitive adhesives having optimized adhesive properties Expired - Lifetime CA2415076C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US21638600P 2000-07-07 2000-07-07
US60/216,386 2000-07-07
US84753201A 2001-05-01 2001-05-01
US09/847,532 2001-05-01
PCT/US2001/021417 WO2002004570A2 (en) 2000-07-07 2001-07-06 Preparation of hydrophilic pressure sensitive adhesives having optimized adhesive properties

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CA2415076A1 true CA2415076A1 (en) 2002-01-17
CA2415076C CA2415076C (en) 2010-04-13

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US (1) US6576712B2 (en)
EP (1) EP1299494B1 (en)
JP (1) JP4323797B2 (en)
CN (1) CN1182219C (en)
AT (1) ATE478932T1 (en)
AU (2) AU7323001A (en)
CA (1) CA2415076C (en)
DE (1) DE60142900D1 (en)
WO (1) WO2002004570A2 (en)

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