A novel neopentyl alpha-cyanoacrylate is provided. It has superior adhesive properties even at high temperatures and whitening-preventing property.

New syntheses for neopentyl bromide and neopentyl chloride are reported which make these interesting aliphatic halides readily available in contraste to the previous methods used. These syntheses also provide unequivocal examples of reactions of the neopentyl-oxygen bond proceeding without rearrangement.

I-Adamantylmethyl 2-cyanoacrylate (1) was prepared by the reaction of 2-cyanoacryloyl chloride with 1-adamantylmethanol . 1,10-Decanediol bis-2-cyanoacrylate (2) was synthesized by transesterification of methyl 2-cyanoacrylate with 1,10-decanediol. Esters1 and2 were studied by X-ray structural analysis.

A novel neopentyl alpha -cyanoacrylate is provided. It has superior adhesive properties even at high temperatures and whitening-preventing property.

A solid cyanoacrylate adhesive composition is disclosed which can be applied to a substrate in solid form and which polymerizes into an adhesive polymer upon liquefying. Preferably the solid cyanoacrylate composition liquefies at temperatures slightly above room temperature and polymerizes upon liquification. -caprolactones are used as a solidifying polymer with cyanoacrylate monomers and other additives to form the solid cyanoacrylate adhesive composition.

The invention comprises compounds of the formula <1048906><1048906><1048906><1048906><1048906><1048906><1048906>

LE PROPRIETATES IMPERMEABILISATORI DE 2-CYANOACRYLATO METHYLIC USATE COMO AGENTE ADHESIVE IN LE DENTISTERIA.—Le proprietates impermeabilisatori de adhesive 2-cyanoacrylato methylic esseva comparate con illos de varie materiales de cementation que es currentemente usate in le dentisteria. 2-cyanoacrylato methylic, cemento a phosphato de zinc, cemento a oxydo de zinc e eugenol, e cemento Grip esseva usate in cementar applicatos plastic a platte superficies de 36 extrahite dentes human.

A process for preparing methyl .alpha.-cyanoacrylate in which methyl cyanoacetate is reacted with formaldehyde to form a polymer, which is subsequently depolymerized to the monomeric product, comprises using an ester of poly(ethylene glycol) as the solvent for the polymerization and depolymerization reactions.

Prepn. of methyl alpha-cyanoacrylate comprises reacting methyl cyanoacetate with HCHO in a solvent of a poly(ethylene glycol)di-acetate, dipropionate, or dibutyrate, having a number average molecular wt. of 200-400. The formed polymer is then depolymerised to the monomeric prod. the purity of yield is 96% or better.