Patents Assigned to Ihara Chemical Industry Co., Ltd.
-
Patent number: 4327204Abstract: 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.Type: GrantFiled: March 18, 1980Date of Patent: April 27, 1982Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yoshijiro Oyaizu, Wataro Koike, Chihiro Yazawa
-
Patent number: 4307034Abstract: 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.Type: GrantFiled: September 13, 1979Date of Patent: December 22, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yoshiki Nakayama, Taro Izawa, Yasushi Higuchi, Yutaka Ohishi, Chihiro Yazawa
-
Patent number: 4289916Abstract: 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.Type: GrantFiled: May 23, 1980Date of Patent: September 15, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yoshiki Nakayama, Chihiro Yazawa, Koji Yamanashi
-
Patent number: 4280958Abstract: 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 formulaR.sub.3-n NH.sub.nwherein R represents a C.sub.1-16 alkyl group or C.sub.1-8 alkoxy group; n is 0 to 2 and R can be the same or different in the case of n is 1 or 0; (2) compounds having the formulaH.sub.2 N(CH.sub.2).sub.n NH andH.sub.2 N(CH.sub.2).sub.n NH(CH.sub.2).sub.n NH.sub.Type: GrantFiled: October 3, 1979Date of Patent: July 28, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yoshiki Nakayama, Yasushi Higuchi, Chihiro Yazawa
-
Patent number: 4267317Abstract: 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.Type: GrantFiled: October 12, 1979Date of Patent: May 12, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Wataro Koike, Tadashi Sasuga, Chihiro Yazawa
-
Patent number: 4254262Abstract: 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 havingX--R'wherein X represents a halogen atom in the presence of a base. The reaction is carried out in the presence of a quarternary ammonium salt or a quaternary phosphonium salt in a nonpolar solvent.Type: GrantFiled: October 12, 1979Date of Patent: March 3, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Wataro Koike, Tadashi Sasuga, Chihiro Yazawa
-
Patent number: 4250156Abstract: Carbonyl sulfide is prepared with an enhanced purity by a process wherein carbon monoxide is caused to bubble through molten sulfur maintained at a temperature of from 300.degree. to 440.degree. C.; and, the resulting gaseous mixture is maintained at a reaction temperature exceeding 510.degree. C. but not higher than 650.degree. C.Type: GrantFiled: March 19, 1980Date of Patent: February 10, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Nobuo Takahashi, Masamichi Shimizu, Kazushige Hirao, Sadayoshi Matsui
-
Patent number: 4246392Abstract: 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.Type: GrantFiled: October 11, 1978Date of Patent: January 20, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Wataro Koike, Masami Takayama, Hideaki Ohashi, Chihiro Yazawa
-
Patent number: 4224300Abstract: Carbon monoxide is reacted with sulfur in the vapor phase at 250.degree.-650.degree. C. to prepare carbonyl sulfide, wherein a reactor is used, in which at least the inner surface is made of an alloy consisting essentially of, based on the weight of the alloy, 20-60% of Cr, 40-65% of Ni, 0-10% of Mo, 0-4% of Nb+Ta, and 0-3% of Fe. The reactor not only possesses good corrosion resistance to the gaseous reaction mixture, but also minimizes the reduction in the purity of carbonyl sulfide produced, which reduction occurs with the lapse of operation time.Type: GrantFiled: August 22, 1979Date of Patent: September 23, 1980Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Nobuo Takahashi, Masanobu Uchiyama, Takaaki Futami, Yoji Imamiya
-
Patent number: 4211723Abstract: Chlorosulfonylbenzoylchloride having the formula ##STR1## wherein X is hydrogen, halogen or nitro is prepared by reacting phosgene with an aromatic sulfocarboxylic acid having the formula ##STR2## or an alkali metal salt or alkaline earth metal salt thereof in the presence of dimethylformamide.Type: GrantFiled: June 20, 1978Date of Patent: July 8, 1980Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Wataro Koike, Takahiro Kimoto, Sadayoshi Matsui
-
Patent number: 4195037Abstract: 4-Alkoxy-3,5-diamino-.alpha.,.alpha.,.alpha.-trifluoromethylbenzene having the formula ##STR1## wherein R represents an alkyl group.Type: GrantFiled: October 4, 1978Date of Patent: March 25, 1980Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Takao Harada, Nobuhide Wada, Hideaki Ohashi, Wataro Koike, Chihiro Yazawa
-
Patent number: 4164956Abstract: Switching valves, e.g. for a closed-type molding apparatus for manufacturing polyurethane elastomers and the like, comprising a valve body having a plurality of openings, preferably five, serving as inlet and outlet ports, and a preferably rotatable valve sleeve which serves for switching the openings without any danger of introducing any other material into the switching valve system. Connections are made between pairs of adjacent openings, one of them being cut off from communication.Type: GrantFiled: February 22, 1977Date of Patent: August 21, 1979Assignee: Ihara Chemical Industry Co. Ltd.Inventors: Akio Takahashi, Hirokichi Saito
-
Patent number: 4159271Abstract: Indoline derivatives having the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are defined below are produced by a cyclization of 2-halogenophenethylamine compounds having the formula ##STR2## wherein R.sub.1 represents hydrogen atom, a lower alkyl, a lower alkoxyl, nitro or hydroxyl group; R.sub.2 represents hydrogen atom; a lower alkoxyl or nitro group; R.sub.3 represents hydrogen atom or a lower alkyl group and at least one of R.sub.1, R.sub.2 and R.sub.3 is a lower alkyl, a lower alkoxyl or nitro group; and X represents a halogen atom, in the presence of a copper type catalyst and ammonia.Type: GrantFiled: January 18, 1978Date of Patent: June 26, 1979Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Hironobu Sano, deceased, Sataro Okamura, deceased, by Eijiro Okamura, legal representative, Yoshiki Nakayama, Kazunari Hirao
-
Patent number: 4140695Abstract: Copper phthalocyanines are produced by reacting a phthalic anhydride or phthalimide with a copper compound and urea in the presence of a catalyst in a polyalkyl-monochlorobenzene having at least two lower alkyl groups and having the formula ##STR1## wherein R.sub.1 and R.sub.2 respectively represent a lower alkyl group having 1 to 3 carbon atoms; R.sub.3 and R.sub.4 respectively represent hydrogen atom or a lower alkyl group having 1 to 3 carbon atoms.Type: GrantFiled: December 15, 1977Date of Patent: February 20, 1979Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Seiji Takeuchi, Sadayoshi Matsui
-
Patent number: 4124640Abstract: Alkoxyanilines are produced by reacting a hydroxyaniline having the formula ##STR1## with an alkyl halide having the formulaR -- Xwherein R represents an alkyl group and X represents a halogen atom in the presence of an alkali metal alcoholate or hydroxide in a nonprotonic organic solvent selected from the group consisting of N-dimethyl acetamide, tetramethyl urea, hexamethylphosphoric triamide, dimethyl sulfoxide and N-methylpyrrolidone or a polyalkyleneglycol alkyl ether having the formulaR'O (R"O).sub.n R'wherein R' represents an alkyl group having 1 to 4 carbon atoms and R" represents an alkylene group having 2 to 3 carbon atoms and n is an integer of 1 to 3.Type: GrantFiled: October 28, 1976Date of Patent: November 7, 1978Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Akira Shinohara, Kazuhito Akiyama, Akira Miki, Sadayoshi Matsui
-
Patent number: 4111879Abstract: A composition for inhibiting an adhesion of shellfish and algae comprises a resin, a medium and a N-arylmaleimide having the formula ##STR1## wherein X represents hydrogen or halogen atom; Y.sub.1 represents hydrogen, or halogen atom or alkyl, lower alkoxy, nitro, hydroxyl, alkoxycarbonyl, carboxyl, phenyl, phenylamino, alkenyl, thiocyano, sulfone, acetylamino, or sulfamoyl group; Y.sub.2 represents hydrogen or halogen atom or alkyl, lower alkoxy, nitro or hydroxyl group and Y.sub.3 represents hydrogen or halogen atom or dialkylamino group.The inhibiting composition is coated on a fishing net, a ship bottom or other apparatus in water.Type: GrantFiled: October 28, 1976Date of Patent: September 5, 1978Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Kogoro Mori, Taro Izawa, Yoshifumi Mizuno, Sadayoshi Matsui
-
Patent number: 4106115Abstract: This invention relates to a material mixing apparatus for use, for example, in the preparation of polyurethane elastomers, wherein a mixer chamber, a set of switching valves and pipelines are maintained to ensure a constantly flowing state for the materials, the apparatus being featured in that it allows to remove the mixed materials in any amount at any time yet preventing contamination of the work site, as a result of a preferably totally closed structure. Two exemplary embodiments are disclosed, having at least two material tanks and switching means, as well as an additional switching means which can serve for a liquid rinsing agent or for a mixture of the materials.Type: GrantFiled: February 22, 1977Date of Patent: August 8, 1978Assignee: Ihara Chemical Industry Co. Ltd.Inventors: Akio Takahashi, Hirokichi Saito
-
Patent number: 4087442Abstract: Indoline is produced by a cyclization of o-halogenophenethylamine compound having the formula ##STR1## wherein X represents a halogen atom in the presence of a copper type catalyst and ammonia.Type: GrantFiled: October 28, 1976Date of Patent: May 2, 1978Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yoshiki Nakayama, Hironobu Sano, Sataro Okamura, Kazunari Hirao
-
Patent number: 4084061Abstract: Phenylacetic acid is produced by reacting chlorotoluene with sodium to form tolylsodium, rearranging the product to benzyl sodium and then reacting the benzyl sodium with a carboxylating agent.Type: GrantFiled: July 26, 1976Date of Patent: April 11, 1978Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Teiichi Kanazawa, Masamichi Shimizu, Susumu Shimoyama
-
Patent number: 4078045Abstract: Carbonyl sulfide is produced by reacting carbon monoxide with sulfur in the presence of an alkaline earth metal compound selected from the group consisting of calcium, strontium or barium sulfides sulfates and halides.Type: GrantFiled: October 28, 1976Date of Patent: March 7, 1978Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yoshiki Nakayama, Hironobu Sano, Sataro Okamura, Kazunari Hirao