ISSN:
0360-6376
Keywords:
Physics
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
An unequivocal and general synthesis of bis(2-cyanoacrylate) monomers from Diels-Alder adducts of the alkyl 2-cyanoacrylates has been developed. Saponification of the anthracene adduct of either isobutyl or ethyl 2-cyanoacrylate to the anthracene/2-cyanoacrylic acid adduct, conversion of the latter to the alkali salt or acid chloride derivatives, followed by respective esterification reactions with an organic dihalide or glycol gave the bis-anthracene adduct precursors to the bis(2-cyanoacrylate) monomers. Heating the bis-adducts with excess maleic anhydride in refluxing xylene effected retrograde diene scission to the bis(2-cyanoacrylate) monomers in up to 80% overall yields. Comonomer blends of the difunctional bis(2-cyanoacrylates) with the alkyl 2-cyanoacrylates gave crosslinked polymeric adhesive compositions exhibiting higher bond strengths under both dry and wet conditions than the noncrosslinked cyanoacrylate adhesives. Potential applications of interest are as pit and fissure sealants in dentistry and for the direct bonding of orthodontic attachments.
Additional Material:
10 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/pol.1978.170161007
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