Ihara Chemical Industry Co., Ltd.

Mitsubishi Chemical Industries Limited

Takao Harada

Chihiro Yazawa

Wataro Koike

Hideaki Ohashi

Nobuhide Wada

Masaaki Ohtani

Yoshijiro Oyaizu

Tatsuhiko Kobayashi

Kazuko Nanjo

A polyurethane elastomer and a metal are strongly adhered by using (1) a composition containing a polyepoxy compound and a polyamine compound and (2) a composition containing an isocyanate compound having a concentration of isocyanate group of 15-50% by weight. An adhered composite article thus obtained has excellent water resistance and heat resistance.

Process for adhering polyurethane elastomer to metal

A process for the preparation of 1,3-propanediol bis(p-aminobenzoate) is described, comprising reacting a p-aminobenzoic acid alkali metal salt with dihalogenated propane in an aprotic polar solvent. In accordance with this process, diesterification proceeds under mild conditions without causing any undesirable side reactions and, therefore the desired 1,3-propanediol bis(p-aminobenzoate) can be obtained in high purity and high yield.

Process for the preparation of 1,3-propanediol bis(p-aminobenzoate)

Bis(aminophenylthioalkyl)terephthalate having the formula ##STR1## wherein R represents a C.sub.1 -C.sub.3 alkyl group. The compounds are useful as hardeners for a polyurethane elastomer.

Bis(aminophenylthioalkyl)terephthalate and hardener for polyurethane

4-Alkoxy-3,5-diamino-.alpha.,.alpha.,.alpha.-trifluoromethylbenzene having the formula ##STR1## wherein R represents an alkyl group.

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Shizuoka, Japan

Takao Harada