Patents by Inventor Tsukuru Izukawa
Tsukuru Izukawa has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 10494469Abstract: This invention relates to a preparation for a polyurethane foam and a polymer polyol preparation for a polyurethane foam, each of which exhibits high coloration and discoloration inhibition properties over a long period of time when stored, and to a composition for a polyurethane foam, which is excellent in storage stability and is preferable as a resin premix. The composition comprises (i) at least one polyol, (ii) a compound having a P?N bond, (iii) an antioxidant having a hydroxyphenyl group, (iv) at least an acid and/or its salt, (v) a catalyst for polyurethane foam production and (vi) a blowing agent.Type: GrantFiled: July 23, 2012Date of Patent: December 3, 2019Assignee: MITSUI CHEMICALS & SKC POLYURETHANES INC.Inventors: Yusuke Maruoka, Atsushi Miyata, Kazuhiko Okubo, Tsukuru Izukawa, Toru Hiraide, Shinsuke Matsumoto
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Publication number: 20140155506Abstract: The present invention relates to a preparation for a polyurethane foam and a polymer polyol preparation for a polyurethane foam, each of which exhibits high coloration and discoloration inhibition properties over a long period of time when stored, and to a composition for a polyurethane foam, which is excellent in storage stability and is preferable as a resin premix.Type: ApplicationFiled: July 23, 2012Publication date: June 5, 2014Applicant: MITSUI CHEMICALS, INC.Inventors: Yusuke Maruoka, Atsushi Miyata, Kazuhiko Okubo, Tsukuru Izukawa, Toru Hiraide, Shinsuke Matsumoto
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Patent number: 6410676Abstract: The object is to provide a method for producing a polyoxyalkylene polyol and a method for producing a derivative thereof wherein the remaining catalyst compound is efficiently removed from a crude polyoxyalkylene polyol by a simple manner, and a method for producing a polyoxyalkylene polyol wherein a crude polyoxyalkylene polyol is produced by addition polymerization of an epoxide compound to an active hydrogen compound using as a catalyst a compound having a P═N bond, then, the crude polyoxyalkylene polyol is allowed to contact with a solid acid having a specific surface area of 450 to 1200 m2/g and an average pore diameter of 40 to 100 Å to control the catalyst-remaining amount in the polyoxyalkylene polyol to 150 ppm or less, and a method for producing a derivative of the-above-described polyol are provided.Type: GrantFiled: May 30, 2000Date of Patent: June 25, 2002Assignee: Mitsui chemicals, Inc.Inventors: Satoshi Yamasaki, Yasunori Hara, Tamotsu Kunihiro, Fumio Yamazaki, Mikio Matsufuji, Ariko Nishikawa, Shinsuke Matsumoto, Tsukuru Izukawa, Masahiro Isobe, Kazuhiko Ohkubo, Kaoru Ueno
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Patent number: 6207794Abstract: The present invention is a polyoxyalkylene polyol, its manufacture method, and derivatives, wherein: it is obtained using a phosphazenium compound as a catalyst; the hydroxyl value is 2˜200 mgKOH/g; total degree of unsaturation is 0.0001˜0.07 meq./g; the head-to-tail bond selectivity of the polyoxyalkylene polyol is 95 mole %; and when the maximum height of the peak of GPC elution curve is set to be 100%, W20 is defined as the peak width at the 20% peak height, and W80 is defined as the peak width at 80% peak height, the ratio of W20/W80 is 1.5 or greater, and less than 3.Type: GrantFiled: December 17, 1998Date of Patent: March 27, 2001Assignee: Mitsui Chemical, Inc.Inventors: Satoshi Yamasaki, Yasunori Hara, Satoshi Tamura, Fumio Yamazaki, Hitoshi Watanabe, Mikio Matsufuji, Shinsuke Matsumoto, Ariko Nishikawa, Tsukuru Izukawa, Masaaki Aoki, Tadahito Nobori, Usaji Takaki
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Patent number: 6156864Abstract: Propylene oxide is added to an active hydrogen compound in the presence of an alkali metal hydroxide catalyst in an amount of from 0.05 to 0.5 mole per mole of the active hydrogen compound at a reaction temperature of from 60 to 98.degree. C. at a reaction pressure less than or equal to 4 kg/cm.sup.2 to prepare a polyoxyalkylene polyol which has a hydroxyl value of from 10 to 35 mg KOH/g, a monool content less than or equal to 15 mol %, a Head-to-Tail bond selectivity greater than or equal to 96 percent, and low viscosity. A polymer polyol is prepared by polymerizing an ethylenically unsaturated monomer in the polyoxyalkylene polyol. A flexible polyurethane foam is prepared by reacting the polyoxyalkylene polyol or the polymer polyol with an organic polyisocyanate compound in the presence of a foaming agent, a catalyst, a surfactant, a crosslinking agent and other additives.Type: GrantFiled: October 30, 1997Date of Patent: December 5, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Kazuhiko Ohkubo, Tomoki Tsutsui, Yoshitsugu Sakaki, Tamotsu Kunihiro, Ariko Nishikawa, Tsukuru Izukawa
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Patent number: 6117937Abstract: A polymer dispersed polyol having a vinyl polymer dispersed in polyol, the vinyl polymer comprising containing 5 to 80 wt % of acrylamide compound (A) represented by the formula (1):CH.sub.2 .dbd.CR.sup.1 CONR.sup.2 R.sup.3 (1)wherein R.sup.1, R.sup.2 and R.sup.3 are a hydrogen atom or hydrocarbon group having 1 to 10 carbon atoms, 0 to 70 wt % of one or more monomer (B) selected from acrylonitrile and methacrylonitrile, and 0 to 95 wt % of a vinyl monomer (C) which can copolymerize with (A) and (B), and 95 to 20 wt % of the total amount of (B) and (C); and when (C) is 0 wt %, (A) is the polymer of a vinyl monomer mixture containing an acrylamide derivative represented by the formula (2):CH.sub.2 .dbd.CR.sup.4 CONR.sup.5 R.sup.6 (2)wherein R.sup.4, R.sup.5 and R.sup.Type: GrantFiled: February 24, 1998Date of Patent: September 12, 2000Assignee: Mitsui Chemicals Inc.Inventors: Shinsuke Matsumoto, Ariko Nishikawa, Tsukuru Izukawa, Masahiro Isobe, Kazuhiko Okubo
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Patent number: 6063825Abstract: A flexible polyurethane foam prepared by reacting polyisocyanate with polyol and/or polymer polyol containing dispersed polymer microparticles obtained by polymerizing an unsaturated compound, water, catalyst, surfactant and, when needed, crosslinking agent and other auxiliary agents, wherein a portion or the whole of the polyol and/or the polymer polyol is prepared in the presence of a compound having a nitrogen-phosphorus double bond as a catalyst, have excellent wet compression set, fatigue by constant-load pounding and dynamic durability.Type: GrantFiled: August 19, 1998Date of Patent: May 16, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Masahiro Isobe, Kazuhiko Ohkubo, Seijiro Sakai, Usaji Takaki, Tadahito Nobori, Tsukuru Izukawa, Satoshi Yamasaki
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Patent number: 5916994Abstract: Propylene oxide is added to an active hydrogen compound in the presence of an alkali metal hydroxide catalyst in an amount of from 0.05 to 0.5 mole per mole of the active hydrogen compound at a reaction temperature of from 60 to 98.degree. C. at a reaction pressure less than or equal to 4 kg/cm.sup.2 to prepare a polyoxyalkylene polyol which has a hydroxyl value of from 10 to 35 mg KOH/g, a monool content less than or equal to 15 mol %, a Head-to-Tail bond selectivity greater than or equal to 96 percent, and low viscosity. A polymer polyol is prepared by polymerizing an ethylenically unsaturated monomer in the polyoxyalkylene polyol. A flexible polyurethane foam is prepared by reacting the polyoxyalkylene polyol or the polymer polyol with an organic polyisocyanate compound in the presence of a foaming agent, a catalyst, a surfactant, a crosslinking agent and other additives.Type: GrantFiled: October 30, 1997Date of Patent: June 29, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Tsukuru Izukawa, Tamotsu Kunihiro, Ariko Nishikawa
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Patent number: 5777175Abstract: Propylene oxide is added to an active hydrogen compound in the presence of an alkali metal hydroxide catalyst in an amount of from 0.05 to 0.5 mole per mole of the active hydrogen compound at a reaction temperature of from 60.degree. to 98.degree. C. at a reaction pressure less than or equal to 4 kg/cm.sup.2 to prepare a polyoxyalkylene polyol which has a hydroxyl value of from 10 to 35 mg KOH/g, a monool content less than or equal to 15 mol %, a Head-to-Tail bond selectivity greater than or equal to 96 percent, and low viscosity. A polymer polyol is prepared by polymerizing an ethylenically unsaturated monomer in the polyoxyalkylene polyol. A flexible polyurethane foam is prepared by reacting the polyoxyalkylene polyol or the polymer polyol with an organic polyisocyanate compound in the presence of a foaming agent, a catalyst, a surfactant, a crosslinking agent and other additives.Type: GrantFiled: April 12, 1995Date of Patent: July 7, 1998Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Kazuhiko Ohkubo, Tomoki Tsutsui, Yoshitsugu Sakaki, Tamotsu Kunihiro, Ariko Nishikawa, Tsukuru Izukawa, Kaoru Ueno, Seijiro Sakai, Yukichi Tanaka
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Patent number: 5545712Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered, alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.Type: GrantFiled: August 23, 1995Date of Patent: August 13, 1996Assignee: Mitsu Toatsu Chemicals, Inc.Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
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Patent number: 5468840Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered. alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.Type: GrantFiled: August 29, 1994Date of Patent: November 21, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
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Patent number: 5416123Abstract: High concentration-low viscosity polymer-polyols are prepared by polymerizing mixtures of acrylonitrile and styrene in polyols, which are free of any polymerizable carbon-carbon double bond, in the presence of alkyl-substituted tertiary amines. Without use, as a dispersion stabilizer, of organic compounds which have a polymerizable carbon-carbon double bond and terminal hydroxyl groups, there can be obtained polymer-polyols which have a concentration of the polymer of 33-60 wt % and a glass transition temperature of the polymer of 90.degree.-120.degree. C.Type: GrantFiled: April 28, 1994Date of Patent: May 16, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ariko Nishikawa, Tamotsu Kunihiro, Tsukuru Izukawa, Kiyotsugu Asai
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Patent number: 5397810Abstract: The present invention relates to a novel polyol obtained by using a specified polyhydric alcohol, polyoxyalkylene polyol, aliphatic amine and/or alkamlamine as a raw material and adding an organic polycarboxylic acid or its anhydride and an alkylene oxide; a polyurethane resin prepared from said novel polyol and an organic polyisocyanate; a rigid polyurethane foam prepared by using a hydrochlorofluorocarbon or hydrofluorocarbon foaming agent which has very low public hazards; and a composite utilizing thereof.The production of rigid polyurethane foam by using the polyol of the invention can be carried out in good operation efficiency and low public hazards. Additionally, properties of the foam thus obtained is equivalent to those of rigid polyurethane foams obtained by using conventional chlorofluorocarbons. Consequently, the rigid polyurethane foam of the invention is very useful for insulation materials and structural insulation materials.Type: GrantFiled: February 19, 1993Date of Patent: March 14, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Masayuki Kimura, Toshio Nozawa, Masahiko Hashiba
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Patent number: 5324774Abstract: High concentration-low viscosity polymer-polyols are prepared by polymerizing mixtures of acrylonitrile and styrene in polyols, which are free of any polymerizable carbon-carbon double bond, in the presence of alkyl-substituted tertiary mines. Without use, as a dispersion stabilizer, of organic compounds which have a polymerizable carbon-carbon double bond and terminal hydroxyl groups, there can be obtained polymer-polyols which have a concentration of the polymer of 33-60 wt % and a glass transition temperature of the polymer of 90.degree.-120.degree. C.Type: GrantFiled: October 14, 1992Date of Patent: June 28, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ariko Nishikawa, Tamotsu Kunihiro, Tsukuru Izukawa, Kiyotsugu Asai
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Patent number: 5246978Abstract: The present invention relates to a polyol, polyurethane resin, rigid polyurethane foam, preparation process thereof and a preparation process of a rigid polyurethane foam composite. The polyol comprises an epoxy resin based polyol, which may be combined with a phenol resin based polyol component and/or an aromatic amine based polyol component. The polyurethane resin, foam and composite using the polyol as a raw material has resistance to dissolution in a hydrochlorofluorocarbon and a hydrofluorocarbon which are foaming agents having very low public environmental hazards and can be used as a thermal insulation material or a thermal insulation structure for refrigerators, freezers, insulation panels, ships and vehicles.Type: GrantFiled: November 8, 1990Date of Patent: September 21, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Toshio Nozawa
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Patent number: 5198475Abstract: A polyurethane resin, rigid polyurethane foam and composite thereof prepared by using a polyol comprising a phenol resin base polyol mixed with an aminophenol base polyol or a polyphenylpolyxylylenepolyamine base polyol or a polymethylenepolyphenylpolyamine base polyol.Type: GrantFiled: October 31, 1990Date of Patent: March 30, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masayuki Kimura, Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Mitsugu Kita
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Patent number: 5107068Abstract: The present invention relates to a novel polyurethane resin, a foam prepared from the resin, a preparation process of the foam, and preparation process of a rigid polyurethane foam composite having a face material. The primary object of the present invention is to provide a rigid polyurethane foam and a rigid polyurethane foam composite fitted with a face material which are prepared by using a hydrochlorofluorocarbon foaming agent having very low public hazards such as ozone layer destruction and green house phenomenon of the earth.The above object can be achieved by using a combination of a polyether polyol initiated from a phenol resin with an alkanolamine or an aliphatic polyhydroxy compound in the production of rigid polyurethane foams.Foams thus obtained have equivalent properties to those of foams obtained by using chlorofluorocarbons (CFC) which are conventional foaming agents.Type: GrantFiled: April 27, 1990Date of Patent: April 21, 1992Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Seiji Esaki, Masayuki Kimura, Toshio Nozawa
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Patent number: 4987198Abstract: There is provided thermosetting resin compositions suitable for injection molding compounds having an apparent curing rate of 0.7 and 0.008 cm/sec respectively at 170.degree. C. and 110.degree. C. by a disk cure tester and an apparent activation energy of at least 26 Kcal/mol, by the addition of fluidity modifiers selected from ether compounds having methylene ether type structure, ester compounds having methylene groups connected with carbonyl ether groups and alcohol compounds having methylene groups connected with hydroxyl groups, to phenolic resin, hexamethylenetetramine, fillers and additives.Type: GrantFiled: October 24, 1988Date of Patent: January 22, 1991Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tsukuru Izukawa, Shuhei Ikado, Toshiyuki Enomoto