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).

  • Patent number: 10494469
    Abstract: 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: Grant
    Filed: July 23, 2012
    Date of Patent: December 3, 2019
    Assignee: MITSUI CHEMICALS & SKC POLYURETHANES INC.
    Inventors: Yusuke Maruoka, Atsushi Miyata, Kazuhiko Okubo, Tsukuru Izukawa, Toru Hiraide, Shinsuke Matsumoto
  • Publication number: 20140155506
    Abstract: 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: Application
    Filed: July 23, 2012
    Publication date: June 5, 2014
    Applicant: MITSUI CHEMICALS, INC.
    Inventors: Yusuke Maruoka, Atsushi Miyata, Kazuhiko Okubo, Tsukuru Izukawa, Toru Hiraide, Shinsuke Matsumoto
  • Patent number: 6410676
    Abstract: 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: Grant
    Filed: May 30, 2000
    Date of Patent: June 25, 2002
    Assignee: 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
  • Patent number: 6207794
    Abstract: 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: Grant
    Filed: December 17, 1998
    Date of Patent: March 27, 2001
    Assignee: 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
  • Patent number: 6156864
    Abstract: 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: Grant
    Filed: October 30, 1997
    Date of Patent: December 5, 2000
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Kazuhiko Ohkubo, Tomoki Tsutsui, Yoshitsugu Sakaki, Tamotsu Kunihiro, Ariko Nishikawa, Tsukuru Izukawa
  • Patent number: 6117937
    Abstract: 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: Grant
    Filed: February 24, 1998
    Date of Patent: September 12, 2000
    Assignee: Mitsui Chemicals Inc.
    Inventors: Shinsuke Matsumoto, Ariko Nishikawa, Tsukuru Izukawa, Masahiro Isobe, Kazuhiko Okubo
  • Patent number: 6063825
    Abstract: 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: Grant
    Filed: August 19, 1998
    Date of Patent: May 16, 2000
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Masahiro Isobe, Kazuhiko Ohkubo, Seijiro Sakai, Usaji Takaki, Tadahito Nobori, Tsukuru Izukawa, Satoshi Yamasaki
  • Patent number: 5916994
    Abstract: 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: Grant
    Filed: October 30, 1997
    Date of Patent: June 29, 1999
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Tsukuru Izukawa, Tamotsu Kunihiro, Ariko Nishikawa
  • Patent number: 5777175
    Abstract: 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: Grant
    Filed: April 12, 1995
    Date of Patent: July 7, 1998
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Kazuhiko Ohkubo, Tomoki Tsutsui, Yoshitsugu Sakaki, Tamotsu Kunihiro, Ariko Nishikawa, Tsukuru Izukawa, Kaoru Ueno, Seijiro Sakai, Yukichi Tanaka
  • Patent number: 5545712
    Abstract: 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: Grant
    Filed: August 23, 1995
    Date of Patent: August 13, 1996
    Assignee: Mitsu Toatsu Chemicals, Inc.
    Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
  • Patent number: 5468840
    Abstract: 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: Grant
    Filed: August 29, 1994
    Date of Patent: November 21, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
  • Patent number: 5416123
    Abstract: 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: Grant
    Filed: April 28, 1994
    Date of Patent: May 16, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Ariko Nishikawa, Tamotsu Kunihiro, Tsukuru Izukawa, Kiyotsugu Asai
  • Patent number: 5397810
    Abstract: 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: Grant
    Filed: February 19, 1993
    Date of Patent: March 14, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Masayuki Kimura, Toshio Nozawa, Masahiko Hashiba
  • Patent number: 5324774
    Abstract: 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: Grant
    Filed: October 14, 1992
    Date of Patent: June 28, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Ariko Nishikawa, Tamotsu Kunihiro, Tsukuru Izukawa, Kiyotsugu Asai
  • Patent number: 5246978
    Abstract: 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: Grant
    Filed: November 8, 1990
    Date of Patent: September 21, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Toshio Nozawa
  • Patent number: 5198475
    Abstract: 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: Grant
    Filed: October 31, 1990
    Date of Patent: March 30, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masayuki Kimura, Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Mitsugu Kita
  • Patent number: 5107068
    Abstract: 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: Grant
    Filed: April 27, 1990
    Date of Patent: April 21, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Seiji Esaki, Masayuki Kimura, Toshio Nozawa
  • Patent number: 4987198
    Abstract: 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: Grant
    Filed: October 24, 1988
    Date of Patent: January 22, 1991
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tsukuru Izukawa, Shuhei Ikado, Toshiyuki Enomoto