Ihara Chemical Industry Co., Ltd.

Chihiro Yazawa

Wataro Koike

Yoshiki Nakayama

Hideaki Ohashi

Yasushi Higuchi

Takao Harada

Yutaka Ohishi

Nobuhide Wada

Masami Takayama

Tadashi Sasuga

Hideo Ohi

Yoshijiro Oyaizu

Yukio Tokunaga

Akira Shinohara

Koji Yamanashi

Kogoro Mori

Taro Izawa

Kazushige Hirao

Kazuko Nanjo

Masahiro Matsuno

The present invention relates to an aquatic organism inhibiting composition which comprises at least one N-arylmaleimide having the formula ##STR1## wherein X.sub.1 and X.sub.2 are the same or different and respectively represent hydrogen or a halogen atom; and Y represents a halogen atom or an alkyl or a lower alkoxy group and n is 0 or an integer of 1 to 3, and at least one organo-tin compound selected from the group consisting of bis(tri-n-butyl tin)mesodibromosuccinate, triphenyl tin monochloroacetate, triphenyl tin hydroxide and bis(tri-n-butyl tin) oxide as active ingredients.

Aquatic organism inhibiting composition

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)

A catalyst of bis(8-quinolinolate) copper (II) complex having the formula ##STR1## which is used for producing a hydroxyphenyl aliphatic acid derivative having the formula ##STR2## wherein R.sub.1 represents hydrogen atom, a lower alkyl group, a lower alkoxy group, hydroxy group or a lower alkylcarbonyl group; R.sub.2 and R.sub.3 are the same or different and respectively represent hydrogen atom or a lower alkyl group; and m is 1 or 2; l is 0, 1 or 2; n is 0, 1 or 2; by reacting a halophenyl aliphatic acid derivative having the formula ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, m, l and n are defined above and R.sub.4 represents hydrogen atom or a monovalent hydrocarbon moiety; and X represents a halogen atom, with a base.

Process for producing hydroxyphenyl aliphatic acid derivatives

A process for producing tolylthiourea having high purity comprises reacting toluidine with a thiocyanate and a mineral acid in the presence of an organic solvent and water.

Process for producing tolylthiourea having high purity

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

A polyurethane elastomer is produced by mixing a hardener composition containing a polyamine, a long chain polyol having an average molecular weight of 300 to 4,000 and a catalyst with an isocyanate composition comprises a prepolymer having terminal isocyanate group and an average molecular weight of 500 to 5,000 and an organic diisocyanate monomer with or without a triisocyanate monomer and a ratio of isocyanate groups of said prepolymer to amino groups of said polyamine is in a range of 0.6:1 to 1.5:1 and a ratio of a total of isocyanate groups in said isocyanate composition to a sum of amino groups of said polyamine and hydroxyl group of said long chain polyol is in a range of 0.8:1 to 1.4:1.

Process for producing polyurethane elastomer by mixing a hardener

An inert organic solvent dispersion of alkali hydroxide is prepared by mixing an alkali hydroxide, an inert organic solvent and a stabilizer and heating and stirring at the temperature for forming the pasty alkali hydroxide and cooling the dispersion. The dispersion of alkali hydroxide is used in a reaction of an active methylene compound with an organoalkyl halide such as a reaction of a halophenylacetonitrile with an isopropyl halide to obtain .alpha.-isopropyl halophenylacetonitrile.

Inert organic solvent dispersion of alkali hydroxide and reaction using

p-Chloroalkylbenzene is selectively produced by chlorinating an alkylbenzene in the presence of a phenoxthine compound having the formula ##STR1## wherein X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are the same or different and respectively represent hydrogen atom; an electron attractive group or an electron donative group and a Lewis acid or its precursor as a catalyst. The process for producing a p-chloroalkylbenzene can be repeatedly carried out by separating the resulting a p-chloroalkylbenzene and adding a hydrogen halide to the residual mixture containing the catalyst to activate the catalyst and chlorinating a newly added alkylbenzene.

Process for producing p-chloroalkylbenzene

An indoline derivative having the formula ##STR1## is produced by a cyclization of 2-halogenophenethylamine having the formula ##STR2## wherein R.sub.1 represents a hydrogen atom or a lower alkyl, a lower alkoxyl, nitro or hydroxyl group; R.sub.2 represents a hydrogen atom or a lower alkoxyl or nitro group; and R.sub.3 represents a hydrogen atom, a lower alkyl, a substituted lower alkyl or a substituted amino group; and X represents a halogen atom in the presence of a copper type catalyst and an amine which is selected from the group consisting of (1) compounds having the formula

Process for producing indoline derivative

A phenoxyalkene derivative having the formula ##STR1## wherein R represents a hydrogen atom, ##STR2## and Y and Z are the same or different and respectively represent a hydrogen atom, trifluoromethyl group, a halogen atom, a lower alkyl group, nitro group or cyano group; R.sub.1 represents a hydrogen atom or a lower alkyl group and R.sub.2 represents carboxyl, hydroxymethyl, allyloxycarbonyl, a lower alkoxycarbonyl, a lower haloalkoxycarbonyl, a S-lower alkylthiocarbonyl, carbamoyl, a N-lower alkylcarbamoyl or a N-phenylcarbamoyl group is produced by reacting a phenol compound having the formula ##STR3## with a dihalogen compound having the formula ##STR4## wherein R, R.sub.1 and R.sub.2 are defined above and X.sub.1 represents a halogen atom and X.sub.2 and X.sub.3 are different and respectively represent a hydrogen atom or a halogen atom, by a simultaneous reaction of an etherification and an unsaturated double bond formation, in the presence of a dehydrogenhalide agent and a polar solvent or a combination of a nonpolar solvent and a quaternary ammonium salt or a quaternary phosphonium salt.

Process for producing phenoxyalkene derivative

A phenoxycarboxylic acid derivative having the formula ##STR1## wherein R represents ##STR2## and X.sub.1 represents a hydrogen atom, a halogen atom, a lower alkyl group, trifluoromethyl group, nitro group or cyano group and X.sub.2 represents a hydrogen atom, a halogen atom, a lower alkyl group, nitro group or cyano group, R' represents ##STR3## and R.sub.1 and R.sub.2 are the same and different and respectively represent hydrogen atom or a lower alkyl group, is produced by reacting a phenol compound having the formula ##STR4## with a halogen compound having

Process for producing phenoxycarboxylic acid derivative

4-Chloro-3,5-diaminophenyl acetates having the formula ##STR1## wherein R represents an alkyl group are useful as curing agent for polyurethane elastomer and intermediates for pharmaceutical and agrochemical compounds and are produced by simultaneously nitrating hydrolyzing 4-chlorobenzylcyanide and esterifying the resulting 4-chloro-3,5-dinitrophenyl acetic acid and then reducing the resulting ester.

4-Chloro-3,5-diaminophenyl acetates and curing agent

A method for the preparation of polyurethane elastomers in which polyethyleneglycol-bis(4-aminobenzoate) is used as the curing agent to be admixed with the polyurethane formulations. This curing agent imparts considerably extended pot life to the ready-prepared polyurethane composition to be cured by heating into an elastomer having improved properties.

Method for the preparation of polyurethane elastomers based on

An aminophenol ether having the formula ##STR1## is produced by reacting an alkali aminophenolate having the formula ##STR2## wherein M represents an alkali metal atom; with an organic halide having the formula

Process for producing aminophenol ether

Triphenylphosphine is produced by reacting a phenylalkali with a phosphorus trihalide in a solvent.

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Yokohama, Japan

Chihiro Yazawa