Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1975-11-18
1977-03-22
Brust, Joseph P.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260465D, C07C12146, C07C12166
Patent
active
040137031
ABSTRACT:
Difunctional monomers of the formula, ##STR1## where R is an organic linking group derived from a diol or a dihalide of the formula X-R-X, where X is either chlorine, bromine, iodine, or hydroxy, are prepared by reacting a conjugated diene, exemplified by anthracene, with an ester of 2-cyanoacrylic acid to form the Diels-Alder adduct of the ester. The ester adduct is hydrolyzed to ultimately obtain either the Diels-Alder adduct of either 2-cyanoacrylic acid--alkali metal salt or 2-cyanoacryloyl halide. These later intermediates are respectively reacted with either the dihalide or the diol to afford the bis-Diels-Alder adduct of the R substituted bis (2-cyanoacrylate) monomer. The protective diene group may then be removed, for example, by reaction with excess maleic anhydride and the resulting difunctional monomer isolated.
The difunctional monomers thus prepared can be utilized as crosslinking agents in blends comprising one or more of these difunctional monomers and at least one monofunctional monomer, exemplified by an ester of 2-cyanoacrylic acid. Alternately, one or more difunctional monomers can be homopolymerized or copolymerized to a highly crosslinked polymer. The copolymerized compositions of the monomer blends are particularly useful as adhesives, especially in dental applications for coating or sealing enamel surfaces of teeth to allay decay, or for the bonding of brackets to teeth in orthodontics the bond being substantially more resistant to moisture than where the monofunctional monomer is used alone.
REFERENCES:
patent: 3423432 (1969-01-01), Weiss et al.
patent: 3463804 (1969-08-01), Ray et al.
patent: 3853945 (1974-12-01), Weiss et al.
Brust Joseph P.
Johnson & Johnson
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