Cyanoacrylate compositions with vinyl terminated ester groups

Details Cyanoacrylate compositions with vinyl terminated ester groups Cyanoacrylate compositions with vinyl terminated ester groups

1998-02-18

2001-01-16

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C156S326000, C156S330900, C424S400000, C424S443000, C424S448000, C424S487000

Reexamination Certificate

active

06174919

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of Invention
The present invention is directed to monomer compositions useful to form industrial, consumer or medical adhesives and sealants, and methods of applying such compositions. More particularly, this invention relates to monomeric cyanoacrylate compositions having vinyl terminated ester groups that allow a biologically acceptable method of cross-linking through the vinyl group.
2. Description of Related Art
U.S. Pat. No. 5,624,669 to Leung et al., discloses hemostatic procedures for sealing punctures and incisions in blood vessels and internal organs by applying a cyanoacrylate monomer. Although the cyanoacrylate may polymerize and/or cross-link in vivo, it preferably does so without the need for external sources of physical initiation such as irradiation.
U.S. Pat. No. 4,134,929 to Stoakley et al. discloses a polymerizable monomeric allyl 2-cyanoacrylate containing portion comprising an amount of an organic peroxide free radical providing compound sufficient to cause crosslinking of a difunctional monomer diester with the allyl 2-cyanoacrylate. Stoakley discloses that crosslinking may occur by way of the allyl group.
U.S. Pat. No. 4,136,138 to Dombroski et al. discloses a polymerizable monomeric 2-cyanoacrylate containing portion comprising an amount of an organic peroxide free radical providing compound sufficient to cause crosslinking of a difunctional monomer diester with the 2-cyanoacrylate. Dombroski discloses that the allyl 2-cyanoacrylate-based adhesive compositions are especially useful as dental adhesives.
U.S. Pat. No. 3,975,422 to Buck discloses difunctional monomers where R is an organic linking group derived from a diol or a dihalide of the formula X—R—X, where X is either Cl, Br, I, or hydroxy. The difunctional monomers are employed as crosslinking agents for monofunctional esters of 2-cyanoacrylates. The monofunctional cyanoacrylate monomers may be cyanoacrylates that are terminated by an alkyl, cyclohexyl or phenyl group. Copolymerized compositions of the monomer blends (difunctional and monofunctional) are useful as adhesives in dental applications. The polymerization of these compositions is initiated by an anionic catalyst or by thermal or other means.
SUMMARY OF THE INVENTION
The present invention is directed to monomeric cyanoacrylate compositions having vinyl terminated ester groups that cross-link through the vinyl group, and biomedical uses of such compositions. Cross-linking occurs by way of the vinyl terminated ester groups. In embodiments, chemical durability, flexibility and elasticity of the resulting polymers or copolymers may be increased and degradability can be reduced. In addition, in embodiments high temperatures or ultraviolet initiators may not be needed for cross-linking.


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