Absorbable cyanoacrylate compositions
An adhesive composition is provided including one or more polymerizable cyanoacrylate monomers and boron trifluoride as a stabilizer or complexing agent. The adhesive composition may also include or be used with a decomplexing agent, particularly one or more quaternary ammonium fluoride salts or one or more quaternary ammonium ether salts. A polymerization initiator or accelerator may also be used. The viscosity of the adhesive composition may be controlled by addition of a thickening agent which may be a polymer or copolymer catalyzed by a boron trifluoride complex or compound. Methods for the application of the adhesive compositions to living tissue are also provided.
1 . An adhesive composition comprising:
one or more polymerizable cyanoacrylate monomers,
a complexing agent for the one or more polymerizable cyanoacrylate monomers comprising boron trifluoride, and
a decomplexing agent comprising at least one quaternary ammonium fluoride salt, at least one quaternary ammonium ether salt, or mixtures thereof.
2 . The adhesive composition of claim 1 wherein the quaternary ammonium fluoride salt comprises a compound according to formula A:
wherein R 10 , R 11 , R 12 and R 13 are each, independently, a substituted or unsubstituted straight, branched or cyclic alkyl group; a substituted or unsubstituted aromatic ring; or a substituted or unsubstituted aralkyl group, wherein the alkyl group, the aromatic ring or the aralkyl group optionally may include a heteroatom S or O.
3 . The adhesive composition of claim 1 wherein the quaternary ammonium ether salt comprises a compound according to formula B:
where R is a straight or branched alkyl group of from about 2 to about 20 carbon atoms, x and y represent the number of repeating units and independently are integers of from 1 to about 10, and X′ is chloride, bromide, iodide, fluoride, sulfate, hydrogen sulfate, sulfite, hydrogen sulfite, bisulfate, bisulfite, or hydroxide.
4 . The adhesive composition of claim 1 further comprising a polymerization initiator comprising a quaternary ammonium chloride salt.
5 . The adhesive composition of claim 1 wherein the one or more polymerizable cyanoacrylate monomers are 2-octyl cyanoacrylate and butyl lactoyl cyanoacrylate.
6 . The adhesive composition of claim 1 further comprising a thickening agent comprising an absorbable polyester catalyzed by a boron trifluoride catalyst.
7 . An adhesive composition comprising:
a first monomer species comprising an alkyl ester cyanoacrylate having the formula
wherein R 1′ and R 2′ are, independently, H, a straight, branched or cyclic alkyl, or are combined together in a cyclic alkyl group, R 3′ is a straight, branched or cyclic alkyl group, and m is 1-8;
a second monomer species different from the first monomer species;
a complexing agent for at least the first monomer species comprising boron trifluoride;
a decomplexing agent comprising at least one quaternary ammonium fluoride salt, at least one quaternary ammonium ether salt, or mixtures thereof; and
a polymerization initiator comprising at least one quaternary ammonium chloride salt.
8 . The adhesive composition of claim 7 wherein the second monomer species is an alkyl α-cyanoacrylate.
9 . The adhesive composition of claim 8 wherein the alkyl α-cyanoacrylate is octyl 2-cyanoacrylate.
10 . The adhesive composition of claim 7 further comprising a thickening agent comprising an absorbable polyester catalyzed by a boron trifluoride catalyst.
11 . The adhesive composition of claim 7 wherein the quaternary ammonium fluoride salt comprises a compound according to formula A:
wherein R 10 , R 11 , R 12 and R 13 are each, independently, a substituted or unsubstituted straight, branched or cyclic alkyl group; a substituted or unsubstituted aromatic ring; or a substituted or unsubstituted aralkyl group, wherein the alkyl group, the aromatic ring or the aralkyl group optionally may include a heteroatom S or O.
12 . The adhesive composition of claim 7 wherein the quaternary ammonium ether salt comprises a compound according to formula B:
where R is a straight or branched alkyl group of from about 2 to about 20 carbon atoms, x and y represent the number of repeating units and independently are integers of from 1 to about 10, and X′ is chloride, bromide, iodide, fluoride, sulfate, hydrogen sulfate, sulfite, hydrogen sulfite, bisulfate, bisulfite, or hydroxide.
13 . The adhesive composition of claim 7 further comprising a plasticizer.
14 . An adhesive composition comprising:
one or more polymerizable cyanoacrylate monomers,
at least one anionic stabilizer,
at least one free radical stabilizer, and
at least one thickening agent comprising an absorbable polyester catalyzed by a boron trifluoride catalyst.
15 . A method of treating living tissue, comprising:
applying to living tissue a biocompatible adhesive composition comprising one or more polymerizable cyanoacrylate monomers and a complexing agent for the one or more polymerizable cyanoacrylate monomers comprising boron trifluoride, wherein the biocompatible adhesive composition is applied in conjunction with a decomplexing agent comprising at least one quaternary ammonium fluoride salt, at least one quaternary ammonium ether salt, or mixtures thereof.
16 . The method of claim 15 wherein the biocompatible adhesive composition further comprises a polymerization initiator comprising a quaternary ammonium chloride salt.
17 . The method of claim 15 wherein the living tissue is internal living tissue.
18 . The method of claim 15 wherein the one or more polymerizable cyanoacrylate monomers are 2-octyl cyanoacrylate and butyl lactoyl cyanoacrylate.
19 . The method of claim 15 wherein the biocompatible adhesive composition is sterilized by dry heat sterilization prior to being applied to living tissue.
20 . The method of claim 15 wherein the biocompatible adhesive composition further comprises a thickening agent comprising an absorbable polyester catalyzed by a boron trifluoride catalyst.