Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1974-10-04
1976-08-17
Brust, Joseph Paul
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260 42, 260 4218, 260 465UA, 260 47UA, 260 797, 2604482N, 260464, 260465D, 526298, C07C12000
Patent
active
039754227
ABSTRACT:
Difunctional monomers of the formula, ##EQU1## 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 latter 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: 3142698 (1964-07-01), Halpern et al.
patent: 3463804 (1969-08-01), Ray et al.
patent: 3616269 (1971-10-01), Aelony et al.
patent: 3655721 (1972-04-01), Arni et al.
patent: 3853945 (1974-12-01), Weiss et al.
Brust Joseph Paul
Johnson & Johnson
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