Patents Assigned to Japan Hydrazine Co., Ltd.
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Patent number: 7122676Abstract: A process for preparing 5,5?-bi-1H-tetrazolediammonium salts (BHT.2NH3) maintaining a high yield through oxaldiimidic acid dihydrazide (OAH) from the starting materials which are cheaply available and are easy to handle. The 5,5?-bi-1H-tetrazolediammonium salts (BHT.2NH3) are prepared by dissolving the oxaldiimidic acid dihydrazide (OAH) obtained by the reaction of hydrated hydrazide with dicyan in an aqueous solution of a weakly acidic compound such as acetic acid, dropwisely adding an aqueous solution of sodium nitrite thereto to form an azide thereof and to effect the cyclization reaction by heating, adding an aqueous solution of sodium hydroxide to the reaction product to convert it into a 5,5?-bi-1H-tetrazoledisodium salt (BHT.2Na), reacting it with an aqueous solution of ammonium chloride, and recovering the formed ammonium salt as sparingly soluble crystals.Type: GrantFiled: March 22, 2001Date of Patent: October 17, 2006Assignees: Japan Hydrazine Co., Ltd., Masuda Chemical Industries Co., Ltd.Inventors: Shunji Hyoda, Masaharu Kita, Hirotoshi Sawada, Shuichi Nemugaki, Takahiro Ueta, Kohki Satoh
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Patent number: 6433181Abstract: A process for the preparation of a highly pure 5,5′-bi-1H-tetrazolediammonium salt comprising adding a small amount of ammonia water to a reaction solution containing a 5,5′-bi-1H-tetrazolediammonium salt synthesized in the presence of a copper catalyst, removing by filtration the blue insoluble components of formed copper.ammonia.5,5′-bi-1H-tetrazole complex to obtain a filtrate of the 5,5′-bi-1H-tetrazoledisodium salt and reacting the filtrate with an aqueous solution of ammonium chloride, and recovering the formed, highly pure ammonium salt as sparingly soluble crystals.Type: GrantFiled: June 4, 2001Date of Patent: August 13, 2002Assignees: Japan Hydrazine Co. Ltd., Masuda Chemical Industry Co, Ltd.Inventors: Shunji Hyoda, Masaharu Kita, Atsushi Sugino, Shuichi Nemugaki, Takahiro Ueta, Koki Sato
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Publication number: 20020058820Abstract: A process for the preparation of a highly pure 5,5′-bi-1H-tetrazolediammonium salt comprising adding a small amount of ammonia water to a reaction solution containing a 5,5′-bi-1H-tetrazolediammonium salt synthesized in the presence of a copper catalyst, removing by filtration the blue insoluble components of formed copper.ammonia.5,5′-bi-1H-tetrazole complex to obtain a filtrate of the 5,5′-bi-1H-tetrazoledisodium salt and reacting the filtrate with an aqueous solution of ammonium chloride, and recovering the formed, highly pure ammonium salt as sparingly soluble crystals.Type: ApplicationFiled: June 4, 2001Publication date: May 16, 2002Applicant: JAPAN HYDRAZINE CO., LTD.Inventors: Shunji Hyoda, Masaharu Kita, Atsushi Sugino, Shuichi Nemugaki, Takahiro Ueta, Koki Sato
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Publication number: 20010029301Abstract: A process for preparing 5,5′-bi-1H-tetrazolediammonium salts (BHT.2NH3) maintaining a high yield through oxaldiimidic acid dihydrazide (OAH) from the starting materials which are cheaply available and are easy to handle. The 5,5′-bi-1H-tetrazolediamnonium salts (BHT.2NH3) are prepared by dissolving the oxaldiimidic acid dihydrazide (OAH) obtained by the reaction of hydrated hydrazide with dicyan in an aqueous solution of a weakly acidic compound such as acetic acid, dropwisely adding an aqueous solution of sodium nitrite thereto to form an azide thereof and to effect the cyclization reaction by heating, adding an aqueous solution of sodium hydroxide to the reaction product to convert it into a 5,5′-bi-1H-tetrazoledisodium salt (BHT.2Na), reacting it with an aqueous solution of ammonium chloride, and recovering the formed ammonium salt as sparingly soluble crystals.Type: ApplicationFiled: March 22, 2001Publication date: October 11, 2001Applicant: JAPAN HYDRAZINE CO., LTD.Inventors: Shunji Hyoda, Masaharu Kita, Hirotoshi Sawada, Shuichi Nemugaki, Takahiro Ueta, Kohki Satoh
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Process for producing alicyclic hydrazine derivatives, tetra-hydropyridazine and hexahydropyridazine
Patent number: 6194577Abstract: The present invention relates to a process for producing alicyclic hydrazine derivatives, tetrahydropyridazine and hexahydropyridazine which are useful as intermediate starting materials such as medicines and agricultural chemicals. Especially, the present invention provides; a process for producing an alicyclic hydrazine derivative or its hydrohalogenic acid salt, which comprises reacting a hydrazine hydrohalogenic acid salt with a doil compound or an alicyclic ether compound in the presence of an excessive inorganic acid existing in a free form or in the form of an acid addition salt; a process for producing tetrahydropyridazine from 1-aminopyrrolidine, which comprises oxidizing 1-aminopyrrolidine with an oxidizing agent to form tetrahydropyridazine; and a process for producing hexahydropyridazine, which comprises oxidizing 1-aminopyrrolidine with an oxidizing agent, synthesizing tetrahydropyridazine, and thereafter, hydrogenating the tetrahydropyridazine in the presence of a base.Type: GrantFiled: June 21, 1999Date of Patent: February 27, 2001Assignee: Japan Hydrazine Co., Ltd.Inventors: Youichi Hasegawa, Shunji Hyoda, Hiroyuki Fujita, Hirotoshi Sawada, Yasuo Oki -
Patent number: 5977360Abstract: The present invention relates to a process for producing alicyclic hydrazine derivatives, tetrahydropyridazine and hexahydropyridazine which are useful as intermediate starting materials such as medicines and agricultural chemicals. Especially, the present invention provides;a process for producing an alicyclic hydrazine derivative or its hydrohalogenic acid salt, which comprises reacting a hydrazine hydrohalogenic acid salt with a diol compound or an alicyclic ether compound in the presence of an excessive inorganic acid existing in a free form or in the form of an acid addition salt;a process for producing tetrahydropyridazine from 1-aminopyrrolidine, which comprises oxidizing 1-aminopyrrolidine with an oxidizing agent to form tetrahydropyridazine; anda process for producing hexahydropyridazine, which comprises oxidizing 1-aminopyrrolidine with an oxidizing agent, synthesizing tetrahydropyridazine, and thereafter, hydrogenating the tetrahydropyridazine in the presence of a base.Type: GrantFiled: December 24, 1997Date of Patent: November 2, 1999Assignee: Japan Hydrazine Co., Ltd.Inventors: Youichi Hasegawa, Shunji Hyoda, Hiroyuki Fujita, Hirotoshi Sawada, Yasuo Oki
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Patent number: 5731465Abstract: An industrially and economically advantageous process for the preparation of a TBH-HX using starting materials which are cheaply available and are easy to handle, maintaining a high yield. A tertiary butyl hydrazine hydrohalogenide is prepared by reacting a hydrazine hydrohalogenide with a methyl tertiary butyl ether in the presence of an acid.Type: GrantFiled: November 7, 1996Date of Patent: March 24, 1998Assignee: Japan Hydrazine Co., Ltd.Inventors: Yoichi Hasegawa, Mineo Nakagawa, Shunji Hyoda, Hiroyuki Fujita, Takafumi Kawada
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Patent number: 5663365Abstract: A process for the preparation of pyrazolone derivatives represented by the general formula ##STR1## wherein R is a hydrogen atom, an alkyl group, an allyl group, an aryl group or an aralkyl group, and R.sub.1 and R.sub.2 are, respectively, a hydrogen atom, an alkyl group or a phenyl group which may have a substituent, comprising reacting a 2,3-dihalocarboxylic acid derivative or a 2-haloacrylic acid derivative with a hydrazine derivative. A pyrazolone or 1-substituted-3-pyrazolones useful as intermediate starting materials for the synthesis of agricultural chemicals, medicine and chemical compounds can be easily and cheaply prepared from widely used industrial starting materials.Type: GrantFiled: October 29, 1996Date of Patent: September 2, 1997Assignee: Japan Hydrazine Co., Ltd.Inventors: Yasuo Yamamoto, Naoki Shirakawa, Shinichi Takano, Yoshio Kawai
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Patent number: 5618978Abstract: A method of producing a choline having a high purity without containing by-products by using a molecule-inclusion complex of the choline as a starting material. A choline inclusion complex without containing by-products is obtained by reacting an aqueous solution of the choline containing, as by-products, those cholines to which are added ethylene oxides with host molecules such as of 1,1'-bis-.beta.-naphthol, and is further reacted with a carbon dioxide gas in order to obtain an aqueous solution of a choline carbonate and/or a choline bicarbonate of a high purity, which is then subjected to the electrolysis using a cation-exchange membrane as a diaphragm, in order to obtain an aqueous solution of the choline of a high purity without containing by-products. The choline that is obtained is a strongly basic compound having a high purity and is very useful as a photoresist-developing solution.Type: GrantFiled: March 26, 1996Date of Patent: April 8, 1997Assignee: Japan Hydrazine Co., Ltd.Inventors: Shunji Hyoda, Youichi Hasegawa, Fumio Toda
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Patent number: 5610209Abstract: A newly-blended one part system heat-resistant epoxy resin composition which exhibits excellent stability at room temperature, quickly undergoes the curing reaction, molded within short periods of time, and, after cured, exhibits excellent Tg, resistance against the water, resistance against degradation by heat, and a variety of excellent properties in combination. The heat-resistant epoxy resin composition having excellent stability at room temperature comprises an epoxy compound having two or more epoxy groups, a curing agent which comprises a naphthalenedicarboxylic dihydrazide as a main component, and a ceramic whisker as a filler.Type: GrantFiled: June 2, 1995Date of Patent: March 11, 1997Assignee: Japan Hydrazine Co., Ltd.Inventor: Shigeo Kiyono