CA2380916A1 - Sterilized cyanoacrylate solutions containing thickeners - Google Patents

Sterilized cyanoacrylate solutions containing thickeners Download PDF

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Publication number
CA2380916A1
CA2380916A1 CA002380916A CA2380916A CA2380916A1 CA 2380916 A1 CA2380916 A1 CA 2380916A1 CA 002380916 A CA002380916 A CA 002380916A CA 2380916 A CA2380916 A CA 2380916A CA 2380916 A1 CA2380916 A1 CA 2380916A1
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CA
Canada
Prior art keywords
composition
thickening agent
poly
monomer
container
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002380916A
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French (fr)
Other versions
CA2380916C (en
Inventor
Timothy Hickey
Ubonwan A. Stewart
Jerry Jonn
John S. Bobo
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Ethicon Inc
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Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2380916A1 publication Critical patent/CA2380916A1/en
Application granted granted Critical
Publication of CA2380916C publication Critical patent/CA2380916C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
    • A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
    • A61L2/08—Radiation
    • A61L2/081—Gamma radiation
    • 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
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
    • A61L2/08—Radiation
    • A61L2/087—Particle radiation, e.g. electron-beam, alpha or beta radiation
    • 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
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
    • A61L2/08—Radiation
    • A61L2/12—Microwaves
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like

Abstract

A method of making a sterile adhesive composition includes placing a mixture of a polymerizable adhesive monomer and a thickening agent in a container, sealing the container, and sterilizing the mixture and the container. The method provides superior viscosity for the monomer composition. The sterile adhesive composition is particularly useful as a medical adhesive and can comprise 1,1-disubstituted ethylene monomers, such as .alpha.-cyanoacrylates .

Claims (52)

1. A method of making a sterile adhesive composition comprising:

(a) placing a mixture comprising a polymerizable 1,1-disubstituted ethylene monomer and a in a container, wherein said thickening agent is soluble in said monomer at room temperature, (b) sealing said container, and (c) sterilizing the mixture in the container, without heat.
2. A method of making a sterile adhesive composition comprising:
(a) placing a mixture comprising a polymerizable 1,1-disubstituted ethylene monomer acid a thickening agent that is not poly(lactic acid) in a container, wherein said thickening agent is soluble in said monomer at room temperature, (b) sealing said container, and (c) sterilizing the mixture in the container.
3. The method of claim 1 or 2, wherein said monomer is at least one member selected from the group consisting of n-butyl cyanoacrylate, 2-octyl cyanoacrylate, and ethyl cyanoacrylate.
4. The method of claim 1 or 2, wherein said thickening agent is selected from the group consisting of poly(2-ethylhexyl methacrylate), poly(2-ethylhexyl acrylate), cellulose acetate butyrate and lactic acid-caprolactone copolymer.
5. The method of claim 4, wherein said thickening agent is poly(2-ethylhexyl methaerylate).
6. The method of claim 4, wherein said thickening agent is poly(2-ethylhexyl acrylate).
7. The method of claim 4, wherein said thickening agent is cellulose acetate butyrate.
8. The method of claim 4, wherein said thickening agent is lactic acid-caprolactone copolymer
9. The method of claim 1 or 2, wherein said thickening agent is biodegradable.
10. The method of claim 1 or 2, wherein said thickening agent is a lactic acid-caprolactone copolymer.
11. The method of claim 1 or 2, wherein said thickening agent comprises from about 0.5-25.0% by weight of the composition.
12. The method of claim 1 or 2, wherein said thickening agent comprises from about 1.0-10.0% by weight of the composition.
13. The method of claim 1 or 2, wherein said thickening agent comprises from about 1.0-5.0% by weight of the composition.
14. The method of claim 1 or 2, wherein said thickening agent has a molecular weight of at least 100,000.
15. The method of claim 1 or 2, wherein said thickening agent has a molecular weight of at least 500,000.
16. the method of claim 1 or 2, wherein said thickening agent has a molecular weight of at least 1,000,000.
17. The method of claim 1, wherein said sterilizing is performed by gamma irradiation, electron beam irradiation, or microwave irradiation.
18. The method of claim 2, wherein said sterilizing is performed by dry heat, gamma irradiation, electron beam irradiation, or microwave irradiation.
19. The method of claim.2, wherein said sterilizing is performed by dry heat.
20. The method of claim 1 or 2, wherein said sterilizing is performed by gamma irradiation.
21. The method of claim 1 or 2, wherein said sterilizing is performed by electron beam irradiation.
22. The method of claim 1 or 2, wherein said composition has a viscosity of about 20-500 centipoise.
23. The method of claim 1 or 2, wherein said composition has a viscosity of about 30-400 centipoise.
24. The method of claim 1 or 2, wherein said mixture further comprises acidic stabilizing agents.
25. The method of claim 1 or 2, wherein said mixture further comprises a plurality of stabilizing agents.
26. The method of claim 1 or 2, wherein said mixture further comprises plasticizing agents.
27. The method of claim 1 or 2, wherein said container is made from at least one material selected from the group consisting of glass, plastic, and metal.
28. The method of claim 1 or 2, wherein said container is made from plastic.
29. The method of claim 1 or 2, wherein said container is made from glass.
30. The method of claim 1 or 2, wherein viscosity of the mixture after sterilization is greater than the viscosity of the mixture before sterilization.
31. The method of claim 1 or 2, wherein viscosity of the mixture after sterilization is less than 100% greater than the viscosity before sterilization.
32. The method of claim 1 or 2, wherein said monomer is an .alpha.-cyanoacrylate.
33. The method of claim 1 or 2, wherein said monomer is an .alpha.-cyanoacrylate of the formula wherein R2 is hydrogen and R3 is a group having the formula wherein R7 is wherein n is 1-14 and R8 is an organic moiety.
34. The method of claim 1 or 2, wherein said thickening agent comprises poly(caprolactone+DL-lactide+glycolide).
35. The method of claim 1 or 2, wherein said thickening agent is poly(vinyl acetate).
36. The method of claim 1 or 2, wherein said thickening agent is poly(vinyl acetate) and said monomer is 2-octyl cyanoacrylate.
37. An adhesive composition, comprising 2-octyl cyanoacrylate and at least one thickener selected from the group consisting of poly(vinyl acetate), poly(2-ethylhexyl methacrylate), and lactic acid-caprolactone copolymer.
38. The composition of claim 37, wherein said paly(vinyl acetate) comprises about 0.5-25.0% by weight of the composition.
39. The composition of claim 37, wherein said poly(vinyl acetate) comprises about 1.0-10.0% by weight of the composition.
40. The composition of claim 37, wherein said poly(vinyl acetate) comprises about 1.0-5.0% by weight of the composition
41. The composition of claim 37, further comprising a plasticizer, a colorant, a radical stabilizer, and an anionic stabilizer.
42. The composition of claim 41, wherein the thickener is poly(2-ethylhexyl methacrylate).

41. The composition of claim 41, wherein the thickener is lactic acid-caprolactone copolymer.

42. The composition of claim 41, wherein the plasticizer is acetyl tributyl citrate.
43. The composition of claim 41, wherein the colorant is 1-hydroxy-4-[4-methylphenylamino]-9,10 anthracenedione.
44. The composition of claim 41, wherein the radical stabilizer is at least one of hydroquinone and p-methoxyphenol.
45. The composition of claim 41, wherein the anionic stabilizer is at least one of acetic acid, sulfuric acid and sulfur dioxide.
46. Use of a composition comprising a polymerizable 1,1-disubstituted ethylene monomer and at least one thickening agent selected from the group consisting of poly(vinyl acetate), poly(2-ethylhexyl methacrylate), poly(2-ethylhexyl acrylate), and lactic acid-caprolactone copolymer, in a medical treatment, the medical treatment comprising applying the composition to tissue.

26a
47. The use of claim 46, wherein said monomer is at least one member selected from the group consisting of n-butyl cyanoacrylate, 2-octyl cyanoacrylate, and ethyl cyanoacrylate.
48. The use of claim 46, wherein said monomer is 2-octyl cyanoacrylate.
49. The use of claim 46, wherein said tissue is skin.
50. The use of claim 46, wherein said tissue is burned, lacerated, irritated, abraded or incised.
51. The use of claim 46, wherein said composition is applied to apposed surgically incised or traumatically lacerated tissue.
52. The use of claim 46, wherein said composition is applied to cover or dress a wound.
CA2380916A 1999-08-12 2000-08-11 Sterilized cyanoacrylate solutions containing thickeners Expired - Lifetime CA2380916C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/374,207 US6310166B1 (en) 1999-08-12 1999-08-12 Sterilized cyanoacrylate solutions containing thickeners
US09/374,207 1999-08-12
PCT/US2000/022159 WO2001012243A1 (en) 1999-08-12 2000-08-11 Sterilized cyanoacrylate solutions containing thickeners

Publications (2)

Publication Number Publication Date
CA2380916A1 true CA2380916A1 (en) 2001-02-22
CA2380916C CA2380916C (en) 2012-03-13

Family

ID=23475789

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2380916A Expired - Lifetime CA2380916C (en) 1999-08-12 2000-08-11 Sterilized cyanoacrylate solutions containing thickeners

Country Status (11)

Country Link
US (3) US6310166B1 (en)
EP (1) EP1206291B1 (en)
JP (1) JP2003507494A (en)
CN (1) CN1378463A (en)
AT (1) ATE306288T1 (en)
AU (1) AU6637800A (en)
BR (1) BR0013267A (en)
CA (1) CA2380916C (en)
DE (1) DE60023153T2 (en)
MX (1) MXPA02001507A (en)
WO (1) WO2001012243A1 (en)

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