Preparing Esters From Alkylene Oxides Patents (Class 560/209)
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Patent number: 10840491Abstract: A method for producing a cellulose nanofiber-containing polyolefin microporous stretched film according to the invention includes: a first step of obtaining a cellulose powder dispersion mixture by uniformly dispersing a cellulose which has a powder particle shape and whose hydroxyl groups have been subjected to a lipophilizing treatment using a dibasic acid anhydride, in a plasticizer; a second step of melt-kneading the cellulose powder dispersion mixture and a polyolefin to obtain a polyolefin resin composition; a third step of extrusion-molding the polyolefin resin composition to obtain an extrudate; a fourth step of stretching the extrudate with a film stretcher to obtain a film; a fifth step of extracting out the plasticizer from the film; and a sixth step of thermally fixing the film from which the plasticizer has been extracted out for inhibiting contraction, while stretching the film at a temperature not higher than a melting point of the polyolefin, in which a twin-screw kneading extruder is used onlType: GrantFiled: June 4, 2014Date of Patent: November 17, 2020Assignee: THE JAPAN STEEL WORKS, LTD.Inventors: Satoru Nakamura, Yoshiyuki Kushizaki, Ryou Ishiguro, Mariko Yoshioka
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Patent number: 10023522Abstract: The hydroxyalkyl acrylate according to the present invention is characterized in that a content amount of an ester generated from acrylic acid dimer and an alkylene oxide is not more than 0.10 mass %. The method for producing a hydroxyalkyl acrylate according to the present invention is characterized in comprising the step of reacting acrylic acid with an alkylene oxide in the presence of a catalyst, wherein a content amount of acrylic acid dimer in the raw material acrylic acid is not more than 3.00 mass %.Type: GrantFiled: September 20, 2013Date of Patent: July 17, 2018Assignee: NIPPON SHOKUBAI CO., LTD.Inventors: Masataka Nakamura, Tokumasa Ishida, Hiroyuki Takaki, Hiroshi Jinno
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Patent number: 9623631Abstract: A radiation-curable laminating adhesive is provided which contains a) at least one urethane (meth)acrylate oligomer and b) at least one additional (meth)acrylate-functionalized component selected from the group consisting of carboxylic acid-functionalized ester-containing (meth)acrylate monomers and polybutadiene poly(meth)acrylates. The adhesive may also contain other components such as (meth)acrylic polyol (meth)acrylates. Flexible packaging laminates may be obtained by using the aforedescribed adhesive to adhere thin polymeric and/or metallic films together, the adhesive being exposed to an amount of radiation effective to cure the adhesive.Type: GrantFiled: June 22, 2005Date of Patent: April 18, 2017Assignee: Henkel IP & Holding GmbHInventors: Alexander P. Mgaya, Balasubramaniam Ramalingam
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Patent number: 9259664Abstract: Process for purifying unsaturated compounds, and a plant for performing the process. Unsaturated compound obtained by the process.Type: GrantFiled: November 6, 2012Date of Patent: February 16, 2016Assignee: EVONIK ROEHM GmbHInventors: Benedikt Laux, Christian Maul, Volker Schleep, Ingo Sander
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Patent number: 8716516Abstract: The present invention relates to a process for preparing polyalkylene glycol di(meth)acrylates by reacting polyalkylene glycol with (meth)acrylic anhydride, wherein the reaction mixture contains at most 0.5% by weight of metal compounds and/or amines, the reaction is carried out in the presence of polymerization inhibitors and the reaction temperature is at least 60° C.Type: GrantFiled: May 5, 2009Date of Patent: May 6, 2014Assignee: Evonik Röhm GmbHInventors: Thorben Schuetz, Joachim Knebel, Mario Gomez Andreu
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Patent number: 8697899Abstract: There is provided a method for producing iron methacrylate being inexpensive, and being high in activity and selectivity and good in solubility to a reaction liquid when being used in production of a hydroxyalkyl methacrylate as a catalyst. The method for producing iron methacrylate for production of a hydroxyalkyl methacrylate according to the present invention includes subjecting a mixture of a metallic iron having an oxygen atom content by XRF analysis of the surface thereof of 6% by mass or lower, and methacrylic acid to a heat treatment at 95° C. or higher and lower than 110° C. for 100 to 600 min. The method for producing a hydroxyalkyl methacrylate according to the present invention includes reacting an alkylene oxide with methacrylic acid to produce the hydroxyalkyl methacrylate, wherein iron methacrylate produced by the method according to the present invention is used as a catalyst.Type: GrantFiled: December 26, 2011Date of Patent: April 15, 2014Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Naoshi Murata, Kuniyoshi Ogura, Takeshi Matsuo, Akira Yoshioka
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Patent number: 8507625Abstract: Provided is a Michael addition product prepared from a multifunctional acryl monomer having multiple hydroxyl groups allowing introduction of acryl functional groups, as a Michael acceptor, and a Michael donor. The Michael addition product is a novel multifunctional compound having an oligomer and a photoinitiator moiety in the molecule. Since it can be cured under a standard UV curing condition without having to add a photoinitiator, it is reduced to air pollution or health problem. Therefore the superior physical properties were obtained by cured coatings without surface tackiness. In addition, its hydroxyl groups allow, through isocyanate bonding or introduction of acryl groups, 3-dimensional crosslinking and molecular and compositional design for improving expandability, friction, and reactivity and hydrophilicity for self-adhesion, hardness of cured film, or the like. Consequently, a very useful, multifunctional or water-dispersible coating composition may be prepared.Type: GrantFiled: September 7, 2010Date of Patent: August 13, 2013Assignee: Korea Research Institute of Chemical TechnologyInventors: Young Chul Kim, Byung Hoon Lee
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Publication number: 20130172591Abstract: There is provided a method for producing iron methacrylate being inexpensive, and being high in activity and selectivity and good in solubility to a reaction liquid when being used in production of a hydroxyalkyl methacrylate as a catalyst. The method for producing iron methacrylate for production of a hydroxyalkyl methacrylate according to the present invention includes subjecting a mixture of a metallic iron having an oxygen atom content by XRF analysis of the surface thereof of 6% by mass or lower, and methacrylic acid to a heat treatment at 95° C. or higher and lower than 110° C. for 100 to 600 min. The method for producing a hydroxyalkyl methacrylate according to the present invention includes reacting an alkylene oxide with methacrylic acid to produce the hydroxyalkyl methacrylate, wherein iron methacrylate produced by the method according to the present invention is used as a catalyst.Type: ApplicationFiled: December 26, 2011Publication date: July 4, 2013Applicant: MITSUBISHI RAYON CO., LTD.Inventors: Naoshi Murata, Kuniyoshi Ogura, Takeshi Matsuo, Akira Yoshioka
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Patent number: 8461374Abstract: Disclosed is a method for producing a hydroxyalkyl (meth)acrylate having high production efficiency and placing little burden on a production system. The method for producing a hydroxyalkyl (meth)acrylate comprises a reaction step of reacting (meth)acrylic acid with an alkylene oxide in a reactor while stirring a liquid containing (meth)acrylic acid and the alkylene oxide with a stirrer to obtain a reaction liquid containing a hydroxyalkyl (meth)acrylate, and thereafter a deaeration step of reducing a pressure in the reactor while stirring the reaction liquid with the stirrer to vaporize and remove an unreacted alkylene oxide in the reaction liquid, a number of stirring revolutions of the stirrer in the deaeration step being reduced to 30 to 85% of a number of stirring revolutions of the stirrer in the reaction step.Type: GrantFiled: August 28, 2009Date of Patent: June 11, 2013Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Masanori Tokuda, Michiyuki Kouno, Junichi Morioka
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Patent number: 8394982Abstract: A process for purifying an unsaturated compound, where purification is performed in a plant with evaporators.Type: GrantFiled: August 29, 2008Date of Patent: March 12, 2013Assignee: Evonik Röhm GmbHInventors: Benedikt Laux, Christian Maul, Volker Schleep, Ingo Sander
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Patent number: 8203018Abstract: Processes for producing a hydroxyalkyl(meth)acrylate which comprise reacting (meth)acrylic acid with an alkylene oxide in the presence of a catalyst. A first process is characterized in that the amount of the acid ingredient is kept, on calculation, at 0.010 or more in terms of molar ratio to the catalyst present in the liquid reaction mixture and that the liquid reaction mixture from which the hydroxyalkyl(meth)acrylate has been distilled off is used in the subsequent reaction. A second process is characterized in that a dialkylene glycol mono(meth)acylate is supplied to the reaction system to cause the dialkyleneglycol mono(meth)acylate to coexist in the liquid reaction mixture.Type: GrantFiled: August 5, 2005Date of Patent: June 19, 2012Assignee: Nippon Shokubai Co., Ltd.Inventors: Tokumasa Ishida, Hiroyuki Takaki, Masahiro Uemura
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Publication number: 20110213175Abstract: This invention relates to processes for preparing fluoroalcohol-substituted (meth)acrylate esters. This invention also relates to block copolymers incorporating repeat units derived from fluoroalcohol-substituted (meth)acrylate esters, and photoresists derived therefrom.Type: ApplicationFiled: May 11, 2011Publication date: September 1, 2011Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventor: WILLIAM BROWN FARNHAM
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Publication number: 20110124906Abstract: Disclosed is a method for producing a hydroxyalkyl (meth)acrylate having high production efficiency and placing little burden on a production system. The method for producing a hydroxyalkyl (meth)acrylate comprises a reaction step of reacting (meth)acrylic acid with an alkylene oxide in a reactor while stirring a liquid containing (meth)acrylic acid and the alkylene oxide with a stirrer to obtain a reaction liquid containing a hydroxyalkyl (meth)acrylate, and thereafter a deaeration step of reducing a pressure in the reactor while stirring the reaction liquid with the stirrer to vaporize and remove an unreacted alkylene oxide in the reaction liquid, a number of stirring revolutions of the stirrer in the deaeration step being reduced to 30 to 85% of a number of stirring revolutions of the stirrer in the reaction step.Type: ApplicationFiled: August 28, 2009Publication date: May 26, 2011Applicant: MITSUBISHI RAYON CO., LTD.Inventors: Masanori Tokuda, Michiyuki Kouno, Junichi Morioka
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Patent number: 7884229Abstract: A method for making a polyether monomer having at least one unsaturated site per molecule and having a desired number of alkoxyl repeating units includes the steps of reacting an active hydrogen-containing monomer having at least one unsaturated site per molecule with an alkyl oxide in the presence of an alkoxylation catalyst and a polymerization inhibitor at a temperature from about 30° C. to less than 45° C. to produce a polyether monomer. In one embodiment, from about 5 to about 1000 parts by weight of a phenothiazine polymerization inhibitor per one million parts by weight of the active hydrogen-containing monomer phenothiazine compound is used as the polymerization inhibitor.Type: GrantFiled: May 4, 2004Date of Patent: February 8, 2011Assignee: Rhodia Inc.Inventors: Amit K. Sharma, Claude K. Martin, Aziz Boukhelifa, Ning Chen
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Patent number: 7682702Abstract: A process for producing water-absorbing polymeric particles comprises the steps of i) drying a hydrogel to produce a dried hydrogel, ii) separating incompletely dried polymeric particles from the dried hydrogel, and iii) drying the separated-off incompletely dried polymeric particles, wherein the separated incompletely dried polymeric particles are comminuted before said drying iii).Type: GrantFiled: November 10, 2006Date of Patent: March 23, 2010Assignee: BASF SEInventor: Meinhard Nitschke
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Patent number: 7361780Abstract: The present invention provides an apparatus for producing hydroxyalkyl(meth)acrylate and method for producing hydroxyalkyl(meth)acrylate, which can maintain high sealing performance even if the maintenance frequency of the blowdown valve is reduced. The apparatus for producing hydroxyalkyl(meth)acrylate of the present invention has a reaction vessel for synthesizing hydroxyalkyl(meth)acrylate, which has a blowdown valve placed in the reaction vessel, and the blowdown valve is opened when discharging contents of the reaction vessel and is a ball valve. The method of producing hydroxyalkyl(meth)acrylate of the present invention involves producing hydroxyalkyl(meth)acrylate using the aforementioned apparatus for producing hydroxyalkyl(meth)acrylate.Type: GrantFiled: January 30, 2004Date of Patent: April 22, 2008Assignees: Mitsubishi Rayon Co., Ltd., Osaka Organic Chemical Ind., Ltd.Inventors: Yoshihiko Satou, Katsunari Shigemune, Junichi Doi, Yasuhiro Kabu, Nobuo Ooya
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Patent number: 7279517Abstract: The present invention relates to a process for the alkoxylation of organic compounds comprising the reaction of at least one organic compound with at least one alkoxylating agent in the presence of a catalyst system, wherein a polyether alcohol is obtained. The catalyst system comprises a metallo organic framework mate-rial comprising pores and at least one metal ion and at least one at least bidentate organic compound, which is coordinately bounded to said metal ion. Furthermore it relates to polyurethanes or polyurethane foams, which are obtainable by using a prepared polyether alcohol as a starting material.Type: GrantFiled: October 18, 2002Date of Patent: October 9, 2007Assignees: BASF Aktiengesellschaft, University of MichiganInventors: Ulrich Mueller, Michael Stoesser, Raimund Ruppel, Eva Baum, Edward Bohres, Marcus Sigl, Lisa Lobree, Omar M. Yaghi, Mohamed Eddaoudi
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Patent number: 7241915Abstract: The present invention provides a process for inhibition of polymerization of a (meth)acrylate ester, which has an extremely higher effect of inhibition of polymerization than in cases where conventional polymerization inhibitors are used. In the process for inhibition of polymerization of a (meth)acrylate ester; an N-oxyl compound and at least one member selected from the group consisting of manganese salt compounds, copper salt compounds, 2,2,6,6-tetramethylpiperidine compounds, and nitroso compounds are used together as polymerization inhibitors, and further an acid is used.Type: GrantFiled: February 11, 2003Date of Patent: July 10, 2007Assignee: Nippon Shokubai Co., Ltd.Inventors: Tokumasa Ishida, Yasuhiro Shingai
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Patent number: 7214817Abstract: The present invention provides: a high-quality hydroxyalkyl (meth)acrylate of which the alkylene glycol di(meth)acrylate content and the acid component content are both low; and its novel production process. The hydroxyalkyl (meth)acrylate, which has a content, in terms of an alkylene glycol di(meth)acrylate as an impurity, of not more than 0.1 weight % and an acid component content of not more than 0.1 weight %, is obtained by a process comprising the step of carrying out a batch reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate; with the process making an adjustment as to charging of both raw materials in such a manner that, for, of a time as needed for supplying both raw materials, a supplying time of not less than 40% of a total supplying time when the raw materials as supplied have a temperature of not lower than 40° C.Type: GrantFiled: May 13, 2003Date of Patent: May 8, 2007Assignee: Nippon Shokubai Co., Ltd.Inventors: Tokumasa Ishida, Hiroyuki Takaki, Masahiro Uemura
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Patent number: 7045651Abstract: The present invention provides a novel production process for a hydroxyalkyl (meth)acrylate, in which it is possible that: in a batch reaction system, the amount of the hydroxyalkyl (meth)acrylate (which is the objective product) as produced is kept nearly on the same level as conventional and further, at the same time, there is suppressed the side production of the alkylene oxide's diaddition product (dialkylene glycol mono(meth)acrylate) that lowers the purity of the product to thus give a bad influence upon its quality.Type: GrantFiled: May 12, 2003Date of Patent: May 16, 2006Assignee: Nippon Shokubai Co., Ltd.Inventors: Tokumasa Ishida, Masahiro Uemura
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Patent number: 6984751Abstract: There is disclosed a novel production process for a hydroxyalkyl (meth)acrylate in which: the diffusion of harmful substances due to disposal of catalysts can be reduced; and also the amount of the catalyst as used can be greatly saved in the entire production process. This production process comprises the step of carrying out a reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate; with the production process being characterized by further comprising the step of recovering the catalyst as has been used for the reaction.Type: GrantFiled: August 1, 2003Date of Patent: January 10, 2006Assignee: Nippon Shokubai Co., Ltd.Inventors: Hiroyuki Takaki, Tokumasa Ishida, Masahiro Uemura
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Patent number: 6958413Abstract: The invention provides a method of liquid-phase reaction using a soluble metallic catalyst in which the soluble metallic catalyst is caused to coexist with an anion-exchange resin during the reaction and the reaction is conducted under such conditions that 50% or more of the soluble metallic catalyst is adsorbed onto the anion-exchange resin. The anion-exchange resin having the soluble metallic catalyst adsorbed thereon is separated from the liquid reaction mixture to thereby recover the soluble metallic catalyst and reuse it in a liquid-phase reaction. The soluble metallic catalyst is efficiently used, recovered, and reused with great ease at low cost in various liquid-phase reactions using the soluble metallic catalyst.Type: GrantFiled: March 25, 2002Date of Patent: October 25, 2005Assignee: Nippon Shokubai Co., Ltd.Inventor: Takafumi Kubo
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Patent number: 6914155Abstract: Active hydrogen in an active-hydrogen-containing compound is activated by using a polymer gel having a three-dimensional network structure holding a solvent inside thereof and active sites inside the three-dimensional network structure and surfaces thereof. The ratio of swell of the polymer gel is preferably set to not less than 2, and it is preferable for the polymer gel to have a basic functional group derived from at least one compound selected from the group consisting of tertiary amine compounds, quaternary ammonium salts, cyclic amine compounds and sulfides. The activation of active hydrogen in the active-hydrogen-containing compound is preferably carried out under the condition that the amount of basic active sites of the polymer gel per unit volume in the active system accompanying the activation of active hydrogen is set to not less than 0.43 mmol/cc.Type: GrantFiled: July 27, 2001Date of Patent: July 5, 2005Assignee: Nippon Shokubai Co., Ltd.Inventors: Hiroshi Yamamoto, Yoshiaki Hirano
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Patent number: 6858761Abstract: The present invention provides a process and its utilization in a process comprising the step of carrying out an addition reaction of an alkylene oxide to an addition-receiving substance in the presence of a resin catalyst, thereby producing the addition reaction product, when the resin catalyst as used for the reaction is persevered so as to recycle it after it is recovered, the unreacted alkylene oxide remaining in the resin catalyst can be prevented from polymerizing and solidifying during the preservation, and the resin catalyst accordingly can be preserved stably for a long time. The resin catalyst as recovered after it is used for the reaction may be preserved under any of the following conditions: 1) at a low temperature of not higher than 40° C.Type: GrantFiled: March 18, 2002Date of Patent: February 22, 2005Assignee: Nippon Shokubai Co., Ltd.Inventors: Yukihiro Yoneda, Tokumasa Ishida, Masahiro Uemura
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Patent number: 6765116Abstract: A process to prepare an improved fluid rare earth phosphate catalyst composition useful in preparing alkylene oxide adducts of organic compounds having active hydrogen atoms is provided. The catalyst is prepared by dissolving a rare earth salt in a C9-C30 active hydrogen containing organic compound and then adding phosphoric acid to the organic compound rare earth mixture.Type: GrantFiled: August 23, 2002Date of Patent: July 20, 2004Assignee: Shell Oil CompanyInventor: Charles Lee Edwards
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Patent number: 6740193Abstract: In accordance with the present invention, there are provided gem-diesters and epoxidized derivatives thereof. When cured, thermosets comprising invention gem-diesters and epoxidized derivatives thereof have thermally and/or chemically labile gem-diester groups interspersed throughout the crosslinked network. Thus, thermosets based on invention gem-diesters and epoxidized derivatives thereof can be easily reworked thermally or chemically by treatment with dilute acidic or basic solutions. Further provided by the present invention are adhesive compositions comprising invention gem-diesters and epoxidized derivatives thereof.Type: GrantFiled: December 21, 2001Date of Patent: May 25, 2004Assignee: Henkel CorporationInventors: John G. Woods, Jianzhao Wang, Jean M. J. Fréchet
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Patent number: 6723872Abstract: The present invention provides: a process in which, when a hydroxyalkyl ester is produced by carrying out a reaction between a carboxylic acid and an alkylene oxide in the presence of a catalyst, the contamination of the hydroxyalkyl ester with water can be inhibited to the maximum limit without washing the inside of a production apparatus together with the raw carboxylic acid or the hydroxyalkyl ester as an aimed product, or without carrying out azeotropic distillation with water and an azeotropic solvent. The process comprises a washing step and thereafter a drying step in the interval of from the stop of a production of the hydroxyalkyl ester till the restart of this production, wherein the washing step is a step of washing the inside of a production apparatus with water and/or an aqueous basic solution, and wherein the drying step is a step of drying under reduced pressure and/or hot-air-drying the inside of the production apparatus.Type: GrantFiled: January 30, 2002Date of Patent: April 20, 2004Assignee: Nippon Shokubai Co., Ltd.Inventors: Yasuhiro Shingai, Kouji Deguchi
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Patent number: 6660881Abstract: The present invention provides a process for producing a (meth)acrylic ester which enables to obtain a (meth)acrylic ester in an excellent reaction yield. The process for producing a (meth)acrylic ester uses an alcohol and an acid as raw materials and an ion-exchange resin as a catalyst, and the process is characterized by comprising a dehydration step and an esterification step, wherein the esterification reaction step follows the dehydration step in which water impregnated in the ion-exchange resin is removed by using as a dehydrating solvent at least one member selected from the group consisting of the alcohol, the acid, and the resulting ester.Type: GrantFiled: August 12, 2001Date of Patent: December 9, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Hajime Matsumoto, Tetsuya Kajihara, Yasuhiro Shingai, Masatoshi Ueoka, Yukihiro Yoneda, Masahiro Uemura, Sei Nakahara, Fumio Munechika
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Patent number: 6646083Abstract: Crosslinked polymers excellent in ion exchange capacity and catalytic activity and in resistance to thermal decomposition and widely applicable in various fields of use; a crosslinking agent which is suited for use as a raw material in the production of crosslinked polymers; a method of producing crosslinked polymers; a method of producing a spherical particle which is suited for use in the production of crosslinked polymers; a method of producing a hydroxy alkyl (meth)acrylate; and a method of producing glycols using the crosslinked polymers are provided.Type: GrantFiled: June 15, 2001Date of Patent: November 11, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Yoshiaki Hirano, Takehiko Morita, Takafumi Kubo, Hiroshi Yamamoto, Kenichi Takematsu, Yutaka Sugiyama
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Patent number: 6610879Abstract: When carrying out a liquid-phase reaction by using a heterogeneous catalyst, the separation of the heterogeneous catalyst and the reaction liquid is carried out certainly and effectively. A reaction method involves carrying out a reaction in liquid phase by using a heterogeneous catalyst particle 30 in a reactor 10, and comprises the steps of: (a) allowing a reaction liquid 40 supplied into the reactor 10 from such as a supplying inlet 12 to react in the presence of the heterogeneous catalyst particle 30, and (b) passing the resultant reaction liquid 40 containing the heterogeneous catalyst particle 30 through a line screen 20 having an opening width where the heterogeneous catalyst particle 30 is not allowed to pass substantially, and then extracting the reaction liquid 40 separated from the heterogeneous catalyst particle 30 from the reactor 10 by way of such as an extracting outlet 14.Type: GrantFiled: July 10, 2001Date of Patent: August 26, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Yukihiro Yoneda, Tetsuya Kajihara, Yasuhiro Shingai, Hajime Matsumoto, Tokumasa Ishida
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Patent number: 6603034Abstract: A process for preparing organozinc halides in solvents, includes reacting a reactive halogen compound with zinc in one or more carboxylic esters. It is also possible to prepare keto, hydroxyl and amino compounds of organozinc halides obtained in a first step from a reactive halogen compound and zinc in one or more carboxylic esters, wherein the organozinc halide obtained is reacted in a second step with an electrophilic reaction partner and the reaction product of the second step is hydrolyzed in a third step.Type: GrantFiled: December 3, 2002Date of Patent: August 5, 2003Assignee: Consortium für Elektrochemische Industrie GmbHInventors: Klas Sorger, Hermann Petersen, Jürgen Stohrer
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Patent number: 6559268Abstract: A perfluoro group-containing compound are represented by the following formula (I): —Rf— is a perfluoro group; and —A represents —OH or a group: or —CyF2y+1 or —CzF2z−1 and a perfluoro group-containing polymerizable compound represented by the following formula (II): R1—O—CH2—CH(OH)—CH2—O—Rf—B (II) In Formula (II), —Rf— is a perfluoro group; —B is —OH or —O—CH2—CH(OH)—CH2—O—R2, or —CyF2y+1 or —CzF2z−1; and R1 and R2 each is a dehydroxyl residue of a (meth)acryloyl group-containing compound or a vinyl group-containing compound. The hardened polymer from the compound has water-repellency, oil-repellency and adhering ability.Type: GrantFiled: March 17, 2000Date of Patent: May 6, 2003Assignee: Kyoeisha Chemcial Co., Ltd.Inventors: Junichi Ikeda, Hajimu Kawa
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Patent number: 6552218Abstract: The present invention provides a process for producing a hydroxyalkyl (meth)acrylate which enables to control sufficiently the formation of a diester at the time of a reaction and/or at the time of distillation. In the process for producing the hydroxyalkyl (meth)acrylate which comprises the step of carrying out a reaction between (meth)acrylic acid and an alkylene oxide in the existence of a catalyst, (1) the reaction between (meth)acrylic acid and the alkylene oxide, or (2) distillation of the resultant hydroxyalkyl (meth)acrylate is performed in the coexistence of a liquid having the relative dielectric constant of not less than 20 at 25° C.Type: GrantFiled: September 4, 2001Date of Patent: April 22, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Tetsuya Kajihara, Tokumasa Ishida, Yasuhiro Shingai
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Patent number: 6541657Abstract: The present invention provides: an unsaturated carboxylate which has both an unsaturated group and a hydroxyl group, and is applicable to a wide range of crosslinking processes, and has moderate polymerizability, and has a novel specific structure; and a production process which enables to obtain this unsaturated carboxylate without causing the rearrangement of the carbon-carbon unsaturated bond of the raw unsaturated oxirane, and gives a high production ratio of unsaturated oxirane-1-mol adduct. A reaction of a specific unsaturated carboxylic acid with a specific unsaturated oxirane is carried out using at least one catalyst selected from the group consisting of chromium compounds, manganese compounds, iron compounds, nickel compounds, zinc compounds, silver compounds, tin compounds, neodymium compounds, and lead compounds, thereby obtaining an unsaturated carboxylate of general formula (1).Type: GrantFiled: March 17, 2001Date of Patent: April 1, 2003Assignee: Nippon Shokubai Co., LtdInventors: Kazuaki Abe, Keiichiro Mizuta, Rie Inoue
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Patent number: 6541656Abstract: Economical and efficient processes for producing an &agr;, &bgr;-unsaturated carboxylic acid heterocycle-inserted ester and an &agr;,&bgr;-unsaturated carboxylic acid polyheteroalkylene ester as well as a catalyst suited for use in economically and efficiently producing an &agr;,&bgr;-unsaturated carboxylic acid ester are provided. The invention provides (1) a process for producing an &agr;,&bgr;-unsaturated carboxylic acid ester which comprises reacting an &agr;,&bgr;-unsaturated carboxylic acid ester with a heterocyclic compound, (2) a process for producing an &agr;,&bgr;-unsaturated carboxylic acid ester which comprises reacting an &agr;,&bgr;-unsaturated carboxylic acid with a heterocyclic compound in the presence of a polymerization inhibitor and a metal oxide catalyst, and (3) a catalyst for the production of an &agr;,&bgr;-unsaturated carboxylic acid ester comprising a metal oxide.Type: GrantFiled: February 8, 2001Date of Patent: April 1, 2003Assignee: Nippon Shokubai Company, Ltd.Inventors: Keiji Yurugi, Takafumi Kubo
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Patent number: 6515166Abstract: A vinyl ester produced by reacting at least one epoxide compound with at least on carboxylic anhydride, containing ethylenically unsaturated groups, the epoxide groups being substantially substituted by two vinyl ester groups.Type: GrantFiled: October 23, 2000Date of Patent: February 4, 2003Assignee: Bakelite AGInventors: Ulrich Grundke, Klaus-Peter Liebetanz, Volker Kalla
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Patent number: 6498268Abstract: A method of producing alkylene glycol esters of unbranched aliphatic dicarboxylic acids with limited homolog distribution, and the use of the esters produced as monomer structural units for producing polymers are disclosed.Type: GrantFiled: May 19, 2000Date of Patent: December 24, 2002Assignee: Cognis Deutschland GmbHInventor: Hans-Christian Raths
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Publication number: 20020156317Abstract: The invention relates to a process for the preparation of esters of (meth)acrylic acid by (trans)esterifying (meth)acrylic acid or its ester derivatives with monohydric or polyhydric alcohols in the presence of an acidic (trans)esterification catalyst, wherein said process after the formation of the esters of (meth)acrylic acid further comprises reacting remaining acid groups with one or more component(s), wherein at least one component forms with at least said catalyst an ester compound not having a &bgr;-hydroxy group or forms an amid compound. The component that reacts with the acidic (trans)esterification catalyst preferably is selected from the group consisting of an oxetane component or derivative, an ortho-ester component, an alcohol component or any mixture thereof.Type: ApplicationFiled: January 11, 2002Publication date: October 24, 2002Inventors: Franciscus J.M. Derks, Michael A.C. Van Dijck
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Patent number: 6465682Abstract: In a production process for a hydroxyalkyl ester, comprising the step of carrying out a reaction between a carboxylic acid and an alkylene in the presence of a catalyst, the present invention is to provide: a production process which can stop the reaction economically and sufficiently safely. In a production process which comprises the step of carrying out the reaction between a carboxylic acid and an alkylene in a reactor 1 in the presence of a catalyst so as to produce a hydroxyalkyl ester, the reaction is stopped by introducing a reaction terminating liquid 21 into the reactor 1, wherein the reaction terminating liquid comprises water in a ratio of not less than 50 weight %, and has a low temperature of −5 to 45° C.Type: GrantFiled: September 17, 2001Date of Patent: October 15, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Yukihiro Yoneda, Tokumasa Ishida, Hajime Matsumoto, Hidekazu Mizohara
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Patent number: 6458988Abstract: A production process for a hydroxyalkyl(meth)acrylate, which comprises the steps of carrying out a reaction between (meth)acrylic acid and an alkylene oxide and stripping the unreacted residue of the alkylene oxide from the resultant reaction liquid, wherein: (1) the stripping step is performed by use of an inert gas, and the concentration of oxygen in the inert gas is adjusted in the range of 0.Type: GrantFiled: September 16, 2000Date of Patent: October 1, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Hajime Matsumoto, Tokumasa Ishida, Yasuhiro Shingai, Masatoshi Ueoka, Yukihiro Yoneda
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Patent number: 6452040Abstract: The present invention provides a production process for a hydroxyalkyl (meth)acrylate which process enables to maintain the oxygen concentration of a gas phase portion of a reactor within a specific low concentration range in any stage of before adding raw materials, during the reaction, and after the reaction. The production process comprises the step of carrying out a reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate, wherein an inert gas and/or a mixed gas of oxygen and an inert gas with a beforehand adjusted oxygen concentration of 0.1 to 14 vol % is used to maintain the oxygen concentration of a gas phase portion of a reactor in the range of 0.1 to 14 vol % (1) before adding the alkylene oxide or (2) during the above reaction or (3) between the completion of the above reaction and the charge for the next reaction.Type: GrantFiled: February 8, 2001Date of Patent: September 17, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Yasuhiro Shingai, Sei Nakahara, Yukihiro Yoneda, Masakazu Asami, Masatoshi Ueoka
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Publication number: 20020111510Abstract: The present invention provides: a process in which, when a hydroxyalkyl ester is produced by carrying out a reaction between a carboxylic acid and an alkylene oxide in the presence of a catalyst, the contamination of the hydroxyalkyl ester with water can be inhibited to the maximum limit without washing the inside of a production apparatus together with the raw carboxylic acid or the hydroxyalkyl ester as an aimed product, or without carrying out azeotropic distillation with water and an azeotropic solvent. The process comprises a washing step and thereafter a drying step in the interval of from the stop of a production of the hydroxyalkyl ester till the restart of this production, wherein the washing step is a step of washing the inside of a production apparatus with water and/or an aqueous basic solution, and wherein the drying step is a step of drying under reduced pressure and/or hot-air-drying the inside of the production apparatus.Type: ApplicationFiled: January 30, 2002Publication date: August 15, 2002Inventors: Yasuhiro Shingai, Kouji Deguchi
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Publication number: 20020091283Abstract: The present invention provides a novel production process for a hydroxyalkyl (meth)acrylate in which, when the hydroxyalkyl (meth)acrylate is produced by carrying out a reaction between (meth)acrylic acid and an alkylene oxide, the unreacted (meth)acrylic acid can be effectively recovered and thereafter recycled as a raw reaction material. The production process for a hydroxyalkyl (meth)acrylate comprises the step of carrying out a reaction between (meth)acrylic acid and an alkylene oxide in order to produce the hydroxyalkyl (meth)acrylate, and further comprises the steps of: recovering the unreacted (meth)acrylic acid by distillation of the resultant reaction liquid; and thereafter recycling the recovered unreacted (meth)acrylic acid as a raw material for the reaction.Type: ApplicationFiled: December 6, 2001Publication date: July 11, 2002Inventors: Hajime Matsumoto, Tetsuya Kajihara, Yukihiro Yoneda
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Patent number: 6414182Abstract: The present invention provide a production process for a hydroxyalkyl ester which comprises the step of carrying out a reaction between a carboxylic acid and an alkylene oxide in the presence of a catalyst, wherein the production process sufficiently enhances the conversion or selectivity in the reaction. The production process is characterized in that the reaction is carried out in a reaction liquid under conditions where a relationship a<b is kept throughout the reaction wherein “a” is a molar concentration (mol %) of the carboxylic acid in the reaction liquid and wherein “b” is a molar concentration (mol %) of the alkylene oxide in the reaction liquid.Type: GrantFiled: July 22, 2000Date of Patent: July 2, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Yasuhiro Shingai, Tokumasa Ishida, Fumio Shibusawa, Tetsuya Kajihara, Yukihiro Yoneda, Hajime Matsumoto, Masatoshi Ueoka
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Patent number: 6413698Abstract: A photohardenable resin composition comprising (A) a urethanated acrylic compound represented by formula (I): (A)a—C—(R)4−a wherein R is H or alkyl; a is 3 or 4; and A represents a group of formula (II): wherein D represents —CH2CH2O—, —CH2CH(CH3)O—, —CH2CH2COO— or —(CH2)6COO—; E represents —CH2CH2O—, —CH2CH(CH3)O—, —COCH2CH2O— or —CO(CH2)6O—; G represents a diol or triol residual group; J represents a divalent or trivalent and substituted or unsubstituted hydrocarbon group; L represents —(CH2CH2O)h— (h: integer of 1 to 4), —(CH2CH(CH3)O)j— (j: integer of 1 to 4), or —(CH2CH2O)k—(CH2CH(CH3)O)m— (k, m: integer of 1 to 3 (k+m=2, 3 or 4); b, c, and d are each 0 or 1 (b+c+d=1, 2 or 3); e is 0, 1 or 2; f is 0 or 1 (e+f=1 or 2); and g is 1 or 2, and (B) a radical polymerizable compound at a (A) : (B) rType: GrantFiled: January 6, 2000Date of Patent: July 2, 2002Assignees: Teijin Seiki Co., Ltd., Takemoto Yushi Kabushiki Kaisha, Shin-Nakamura Chemical Co., Ltd.Inventors: Yorikazu Tamura, Tsuneo Hagiwara, Makoto Ohtake, Minoru Shinoda, Toshiharu Suzuki, Tatsuhiko Ozaki, Yasushi Ishihama, Takayuki Nakamura
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Publication number: 20020082443Abstract: The present invention provides: a production process for a hydroxyalkyl (meth)acrylate, which can raise productivity together with avoiding danger of explosion, and further can suppress side-formation of impurities such as a diester or a monoester wherein the impurities have a bad influence on product quality. When the time from the start of adding an alkylene oxide (AO) till the end of supplying the entirety of the AO is defined as T (hour), the amount of more than 50% of the entirety of the AO is supplied before T/2 (hour) has passed since the start of adding the AO.Type: ApplicationFiled: December 19, 2001Publication date: June 27, 2002Inventors: Masahiro Uemura, Tokumasa Ishida, Yukihiro Yoneda, Tetsuya Kajihara, Yasuhiro Shingai, Tadayoshi Kawashima
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Patent number: 6384267Abstract: In a process for producing hydroxyalkyl (meth)acrylates by the reaction of (meth)acrylic acid with an alkylene oxide, a thermally and chemically stable anion exchange resin is used as a catalyst, which resin contains a repeating unit represented by the following formula (1) as a component: wherein A is a straight chain alkylene group having 3 to 8 carbon atoms, each of R1, R2, and R3 is a hydrocarbon group or an alkanol group having 1 to 4 carbon atoms, which may be substituted with a hydroxyl group, X− is a counter ion coordinated with an ammonium group, where the substituent A with the ammonium group may be substituted at any position of a benzene ring, and the benzene ring may be substituted with an alkyl group or a halogen atom. The process can economically efficiently produce hydroxyalkyl (meth)acrylates without disadvantages such as deterioration in properties of a distillation residue.Type: GrantFiled: February 14, 2000Date of Patent: May 7, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Yasuhiro Shingai, Masatoshi Ueoka, Junya Watanabe, Hirohisa Kubota
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Patent number: 6380424Abstract: The present invention provides: a purification process for hydroxyalkyl (meth)acrylate that suppresses forming by-products such as a diester and a dimer of acrylic acid in the distillation process, and can ensure a purity of hydroxyalkyl (meth)acrylate, and can operate stably without causing troubles such as polymerization. In a purification process for hydroxyalkyl (meth)acrylate which is obtained by reacting (meth)acrylic acid and alkylene oxide in the presence of a catalyst, and removing unreacted alkylene oxide and/or (meth)acrylic acid in a reaction solution after the reaction, a distillation apparatus having a portion of a vacant column and a thin-film evaporation apparatus are used at the same time.Type: GrantFiled: September 16, 2000Date of Patent: April 30, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Yukihiro Yoneda, Fumio Shibusawa, Yasuhiro Shingai, Masatoshi Ueoka
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Patent number: 6372923Abstract: The present invention provides a process for preparing an alcohol derivative, where the alcohol derivative is an ester, acetal, ketal, ether glycoside, or alkyl glycoside, by reacting an alcohol with a carbonyl compound, alcohol, olefin, epoxy compound or saccharide, where C2-4 vicinal alkylene oxides are excluded, in the presence of (A) an aluminum alkoxide and (B) sulfuric acid or phosphoric acid.Type: GrantFiled: May 31, 2000Date of Patent: April 16, 2002Assignee: Kao CorporationInventors: Mitsuru Uno, Munehisa Okutsu, Tomohito Kitsuki
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Publication number: 20020042538Abstract: In a production process for a hydroxyalkyl ester, comprising the step of carrying out a reaction between a carboxylic acid and an alkylene in the presence of a catalyst, the present invention is to provide: a production process which can stop the reaction economically and sufficiently safely. In a production process which comprises the step of carrying out the reaction between a carboxylic acid and an alkylene in a reactor 1 in the presence of a catalyst so as to produce a hydroxyalkyl ester, the reaction is stopped by introducing a reaction terminating liquid 21 into the reactor 1, wherein the reaction terminating liquid comprises water in a ratio of not less than 50 weight %, and has a low temperature of −5 to 45° C.Type: ApplicationFiled: September 17, 2001Publication date: April 11, 2002Applicant: Nippon Shokubai Co., Ltd.Inventors: Yukihiro Yoneda, Tokumasa Ishida, Hajime Matsumoto, Hidekazu Mizohara