Cyanoacrylate compositions containing anti-microbial agent

• US 20050042266A1
• Filed: 08/21/2003
• Published: 02/24/2005
• Est. Priority Date: 08/21/2003
• Status: Abandoned Application

• Current Assignee: Ethicon Incorporated (Johnson & Johnson)
• Original Assignee: Closure Medical Corporation (Johnson & Johnson)
• Inventors: Narang, Upvan
• Application Number:
  US10/644,874
• Publication Number:
  US 20050042266A1
• Time in Patent Office: Days
• US Class Current: 424/448
• CPC Class Codes: A61L 2300/202 with halogen atoms, e.g. triclosan, povidone-iodine
• CPC Class Codes: A61L 2300/404 Biocides, antimicrobial agents, antiseptic agents
• CPC Class Codes: A61L 24/0015 Medicaments; Biocides
• CPC Class Codes: A61L 24/06 obtained by reactions only involving carbon-to-carbon unsaturated bonds A61L24/043, A61L24/046 take precedence
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: C08K 3/015 Biocides macromolecular substances as carriers for biocide material A01N25/10
• CPC Class Codes: C08K 5/136 Phenols containing halogens
• CPC Class Codes: C08L 2666/04 Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
• CPC Class Codes: C08L 33/06 of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
• CPC Class Codes: C08L 33/068 containing glycidyl groups
• CPC Class Codes: C08L 35/04 Homopolymers or copolymers of nitriles C08L35/06, C08L35/08 take precedence

Abstract

A monomeric adhesive composition includes a polymerizable monomer, such as a 1,1-disubstituted monomer such as a cyanoacrylate, and an antimicrobial agent, wherein the antimicrobial agent is a phenolic active compound. Examples of suitable phenolic active compounds include halogenated phenol compounds such as chlorinated phenol compounds (such as triclosan) and brominated phenol compounds.

Claims

1. A monomeric adhesive composition comprising:

a polymerizable monomer, and

an antimicrobial agent,

wherein said antimicrobial agent is a phenolic active compound.

2. The composition of claim 1, wherein said antimicrobial agent is a halogenated phenol compound.

3. The composition of claim 1, wherein said antimicrobial agent is selected from the group consisting of chlorinated phenol compounds and brominated phenol compounds.

4. The composition of claim 1, wherein said antimicrobial agent is a chlorinated phenol compound selected from the group consisting of parachlorometaxylenol, triclosan, p-chlorophenol, 2-chlorophenol, 3-chlorophenol, 4-chlorophenol, 2,4-dichlorophenol, 2,4,6-trichlorophenol, 2,3,4,6-tetrachlorophenol, pentachlorophenol, 4-chlororesorcinol, 4,6-dichlororesorcinol, 2,4,6-trichlororesorcinol, alkylchlorophenols, cyclohexyl p-chlorophenol, o-benzyl p-chlorophenol, o-benxyl-m-methyl p-chlorophenol, o-benzyl-m,m-dimethyl p-chlorophenol, o-phenylethyl p-chlorophenol, o-phenylethyl-m-methyl p-chlorophenol, dichloro-m-xylenol, chlorocresol, o-benzyl-p-chlorophenol, 3,4,6-trichlorphenol, 4-chloro-2-phenylphenol, 6-chloro-2-phenylphenol, o-benzyl-p-chlorophenol, 2,4-dichloro-3,5-diethylphenol, and mixtures thereof.

5. The composition of claim 1, wherein said antimicrobial agent is triclosan.

6. The composition of claim 1, wherein said antimicrobial agent is a brominated phenol compound selected from the group consisting of p-bromophenol, methyl p-bromophenol, ethyl p-bromophenol, n-propyl p-bromophenol, n-butyl p-bromophenol, n-amyl p-bromophenol, sec-amyl p-bromophenol, n-hexyl p-bromophenol, cyclohexyl p-bromophenol, o-bromophenol, tert-amyl o-bromophenol, n-hexyl o-bromophenol, n-propyl-m,m-dimethyl o-bromophenol, 2,2′

-methylene bis(4-chloro-6-bromophenol), and mixtures thereof.

7. The composition of claim 1, wherein said antimicrobial agent is soluble in said monomer at room temperature and substantially all of said monomer remains stable for at least five minutes after forming the composition.

8. The composition of claim 1, wherein said antimicrobial agent is compatible with sterilization processing of said composition.

9. The composition of claim 1, wherein said composition remains stable for at least one hour after forming the composition.

10. The composition of claim 1, wherein said composition remains stable for at least twenty-four hours after forming the composition.

11. The composition of claim 1, wherein said composition remains stable for at least eighteen months after forming the composition.

12. The composition of claim 1, wherein said anti-microbial agent does not substantially affect the polymerization rate of the monomer.

13. The composition of claim 1, wherein said monomer is a 1,1-disubstituted ethylene monomer.

14. The composition of claim 1, wherein said monomer is a cyanoacrylate.

15. The composition of claim 1, wherein said composition is sterile.

29. A polymer film formed by polymerizing the monomer in the composition of claim 1.

16. A method of making a monomeric adhesive composition, comprising mixing an antimicrobial agent with a polymerizable monomer, wherein said antimicrobial agent is a phenolic active compound.

17. The method of claim 16, wherein said antimicrobial agent is a halogenated phenol compound.

18. The method of claim 16, wherein said antimicrobial agent is selected from the group consisting of chlorinated phenol compounds and brominated phenol compounds.

19. The method of claim 16, wherein said antimicrobial agent is a chlorinated phenol compound selected from the group consisting of parachlorometaxylenol, triclosan, p-chlorophenol, 2-chlorophenol, 3-chlorophenol, 4-chlorophenol, 2,4-dichlorophenol, 2,4,6-trichlorophenol, 2,3,4,6-tetrachlorophenol, pentachlorophenol, 4-chlororesorcinol, 4,6-dichlororesorcinol, 2,4,6-trichlororesorcinol, alkylchlorophenols, cyclohexyl p-chlorophenol, o-benzyl p-chlorophenol, o-benxyl-m-methyl p-chlorophenol, o-benzyl-m,m-dimethyl p-chlorophenol, o-phenylethyl p-chlorophenol, o-phenylethyl-m-methyl p-chlorophenol, dichloro-m-xylenol, chlorocresol, o-benzyl-p-chlorophenol, 3,4,6-trichlorphenol, 4-chloro-2-phenylphenol, 6-chloro-2-phenylphenol, o-benzyl-p-chlorophenol, 2,4-dichloro-3,5-diethylphenol, and mixtures thereof.

20. The method of claim 16, wherein said antimicrobial agent is triclosan.

21. The method of claim 16, wherein said antimicrobial agent is soluble in said monomer at room temperature and substantially all of said monomer remains stable for at least five minutes after forming the composition.

22. The method of claim 16, wherein said antimicrobial agent is compatible with sterilization processing of said composition.

23. The method of claim 16, wherein said monomer is a 1,1-disubstituted ethylene monomer.

24. The method of claim 16, wherein said monomer is a cyanoacrylate.

25. The method of claim 16, wherein said composition is sterile.

26. A method of making a sterile, antimicrobial adhesive composition comprising:

placing a mixture of a polymerizable monomer and an antimicrobial agent in a container, wherein said antimicrobial agent is a phenolic active compound,

sealing said container, and

sterilizing the mixture in the container,

wherein said mixture remains stable for at least five minutes after forming the mixture.

27. The method of claim 26, wherein said sterilizing is performed by dry heat, moist heat, gamma irradiation, electron beam irradiation, microwave irradiation, or retort canning.

28. A method of applying a monomeric adhesive composition, comprising:

applying a monomeric adhesive composition comprising a polymerizable monomer and an antimicrobial agent, wherein said antimicrobial agent is a phenolic active compound and, to a tissue surface; and

allowing the monomeric adhesive composition to polymerize on said tissue surface.