Patents Assigned to Ihara Chemical Industry Co., Ltd.
  • Patent number: 4327204
    Abstract: 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: Grant
    Filed: March 18, 1980
    Date of Patent: April 27, 1982
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshijiro Oyaizu, Wataro Koike, Chihiro Yazawa
  • Patent number: 4307034
    Abstract: 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: Grant
    Filed: September 13, 1979
    Date of Patent: December 22, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshiki Nakayama, Taro Izawa, Yasushi Higuchi, Yutaka Ohishi, Chihiro Yazawa
  • Patent number: 4289916
    Abstract: 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: Grant
    Filed: May 23, 1980
    Date of Patent: September 15, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshiki Nakayama, Chihiro Yazawa, Koji Yamanashi
  • Patent number: 4280958
    Abstract: 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: Grant
    Filed: October 3, 1979
    Date of Patent: July 28, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshiki Nakayama, Yasushi Higuchi, Chihiro Yazawa
  • Patent number: 4267317
    Abstract: 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: Grant
    Filed: October 12, 1979
    Date of Patent: May 12, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Wataro Koike, Tadashi Sasuga, Chihiro Yazawa
  • Patent number: 4254262
    Abstract: 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: Grant
    Filed: October 12, 1979
    Date of Patent: March 3, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Wataro Koike, Tadashi Sasuga, Chihiro Yazawa
  • Patent number: 4250156
    Abstract: 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: Grant
    Filed: March 19, 1980
    Date of Patent: February 10, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuo Takahashi, Masamichi Shimizu, Kazushige Hirao, Sadayoshi Matsui
  • Patent number: 4246392
    Abstract: 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: Grant
    Filed: October 11, 1978
    Date of Patent: January 20, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Wataro Koike, Masami Takayama, Hideaki Ohashi, Chihiro Yazawa
  • Patent number: 4224300
    Abstract: 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: Grant
    Filed: August 22, 1979
    Date of Patent: September 23, 1980
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuo Takahashi, Masanobu Uchiyama, Takaaki Futami, Yoji Imamiya
  • Patent number: 4211723
    Abstract: 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: Grant
    Filed: June 20, 1978
    Date of Patent: July 8, 1980
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Wataro Koike, Takahiro Kimoto, Sadayoshi Matsui
  • Patent number: 4195037
    Abstract: 4-Alkoxy-3,5-diamino-.alpha.,.alpha.,.alpha.-trifluoromethylbenzene having the formula ##STR1## wherein R represents an alkyl group.
    Type: Grant
    Filed: October 4, 1978
    Date of Patent: March 25, 1980
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Takao Harada, Nobuhide Wada, Hideaki Ohashi, Wataro Koike, Chihiro Yazawa
  • Patent number: 4164956
    Abstract: 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: Grant
    Filed: February 22, 1977
    Date of Patent: August 21, 1979
    Assignee: Ihara Chemical Industry Co. Ltd.
    Inventors: Akio Takahashi, Hirokichi Saito
  • Patent number: 4159271
    Abstract: 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: Grant
    Filed: January 18, 1978
    Date of Patent: June 26, 1979
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Hironobu Sano, deceased, Sataro Okamura, deceased, by Eijiro Okamura, legal representative, Yoshiki Nakayama, Kazunari Hirao
  • Patent number: 4140695
    Abstract: 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: Grant
    Filed: December 15, 1977
    Date of Patent: February 20, 1979
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Seiji Takeuchi, Sadayoshi Matsui
  • Patent number: 4124640
    Abstract: 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: Grant
    Filed: October 28, 1976
    Date of Patent: November 7, 1978
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Akira Shinohara, Kazuhito Akiyama, Akira Miki, Sadayoshi Matsui
  • Patent number: 4111879
    Abstract: 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: Grant
    Filed: October 28, 1976
    Date of Patent: September 5, 1978
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Kogoro Mori, Taro Izawa, Yoshifumi Mizuno, Sadayoshi Matsui
  • Patent number: 4106115
    Abstract: 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: Grant
    Filed: February 22, 1977
    Date of Patent: August 8, 1978
    Assignee: Ihara Chemical Industry Co. Ltd.
    Inventors: Akio Takahashi, Hirokichi Saito
  • Patent number: 4087442
    Abstract: 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: Grant
    Filed: October 28, 1976
    Date of Patent: May 2, 1978
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshiki Nakayama, Hironobu Sano, Sataro Okamura, Kazunari Hirao
  • Patent number: 4084061
    Abstract: 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: Grant
    Filed: July 26, 1976
    Date of Patent: April 11, 1978
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Teiichi Kanazawa, Masamichi Shimizu, Susumu Shimoyama
  • Patent number: 4078045
    Abstract: 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: Grant
    Filed: October 28, 1976
    Date of Patent: March 7, 1978
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshiki Nakayama, Hironobu Sano, Sataro Okamura, Kazunari Hirao