Patents by Inventor Li-Biao Han
Li-Biao Han 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: 10316046Abstract: An object of the invention is to provide a method for efficiently producing an acyloxysilane which is useful as a functional chemical, an acyloxysilane obtained thereby, and the use thereof. The present invention provides: a method for producing an acyloxysilane, including a reaction step of reacting an alkoxysilane with a carboxylic anhydride in the presence of a catalyst, wherein the alkoxysilane is a specified alkoxysilane represented by General Formula (I), the carboxylic anhydride is a specified carboxylic acid represented by General Formula (IIA) or (IIB), the catalyst is an acid catalyst, and an acyloxysilane obtained in the reaction step is a specified acyloxysilane represented by General Formula (IIIA) or (IIIB); and the use of the acyloxysilane as a surface treatment agent or the like.Type: GrantFiled: March 9, 2016Date of Patent: June 11, 2019Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGYInventors: Hiroshi Yamashita, Makiko Hatori, Michiyo Yoshinaga, Li-Biao Han, Shigeru Shimada, Kazuhiko Sato
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Publication number: 20180044359Abstract: An object of the invention is to provide a method for efficiently producing an acyloxysilane which is useful as a functional chemical, an acyloxysilane obtained thereby, and the use thereof. The present invention provides: a method for producing an acyloxysilane, including a reaction step of reacting an alkoxysilane with a carboxylic anhydride in the presence of a catalyst, wherein the alkoxysilane is a specified alkoxysilane represented by General Formula (I), the carboxylic anhydride is a specified carboxylic acid represented by General Formula (IIA) or (IIB), the catalyst is an acid catalyst, and an acyloxysilane obtained in the reaction step is a specified acyloxysilane represented by General Formula (IIIA) or (IIIB); and the use of the acyloxysilane as a surface treatment agent or the like.Type: ApplicationFiled: March 9, 2016Publication date: February 15, 2018Inventors: Hiroshi Yamashita, Makiko Hatori, Michiyo Yoshinaga, Li-BIAO Han, Shigeru Shimada, Kazuhiko Sato
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Patent number: 7829044Abstract: The invention provides a process by which rare earth metal ions can be efficiently extracted by easy operation, and effective extracting reagents for the process. Specifically, phosphonamides represented by the general formula [1]; a process for producing the same; reagents for extracting rare earth metal ions, containing the phosphonamides; and a process for extraction of rare earth metal ions with the phosphonamides: [1] wherein R1 is alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, aralkyl, or a heterocyclic group, with the proviso that each group may be substituted; R2 is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, aralkyl, or a heterocyclic group, with the proviso that each group may be substituted; R3 is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, aralkyl, or a heterocyclic group, with the proviso that each group may be substituted, or the two R3s may be united to form alkylene, cycloalkylene, or arylene.Type: GrantFiled: March 3, 2003Date of Patent: November 9, 2010Assignee: Japan Science and Technology AgencyInventors: Yoshikazu Makioka, Teruyuki Hayashi, Masato Tanaka, Li-Biao Han
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Publication number: 20100174079Abstract: Disclosed is a process for producing an optically active phosphorus compound having an R- or S-type absolute configuration on phosphorus in a simple manner and at high efficiency, while avoiding racemization. An optically active phosphorus compound having an R- or S-type absolute configuration on phosphorus represented by the general formula (III) can be produced by reacting an optically active phosphorus compound having an R- or S-type absolute configuration on phosphorus represented by the general formula (I) with a metal compound represented by the general formula (II) and water. (I) wherein R1 represents a hydrogen atom, analkyl group, a cycloalkyl group, an aralkyl group or an aryl group; and R2 represents a hydrogen, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, alkenyl group, an alkoxy group, an aryloxy group, a heterocyclic ring residue or a silyl-containing group. R3M (II) wherein R3 is the same as R2; and M represents a lithium or magnesium halide MgX (X?Cl, Br or I).Type: ApplicationFiled: August 20, 2007Publication date: July 8, 2010Applicant: National Institute of Advanced Industrial Science TechnologyInventors: Li-Biao Han, Qing Xu
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Publication number: 20080091040Abstract: A novel, optically active alkenylphosphinic acid ester having chirality on a phosphorus atom; and a simple process for producing the ester. An optically active, hydrogen phosphinic acid ester is reacted with an acetylene compound in the presence of a catalyst containing a metal of group 9 or 10 of the periodic table to thereby obtain a novel, optically active alkenylphosphinic acid ester which has chirality on a phosphorus atom and is represented by the following general formula [1] and/or [2].Type: ApplicationFiled: October 5, 2007Publication date: April 17, 2008Applicants: Japan Science and Technology Corporation, National Institute of Advanced Industrial Science and TechnologyInventors: Li-Biao Han, Chang-Qiu Zhao, Masato Tanaka
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Patent number: 7166737Abstract: The present invention relates to a new manufacturing method for phosphonate esters, which have utility as a carbon-carbon binding formation agent, as well as a synthesis intermediate for biologically active substances such as medical drugs and agri-chemicals. Specifically the present invention relates to a new industrially advantageous manufacturing method for phosphonate esters in which the phosphonate esters of the subject can be efficiently obtained with a high yield rate through a simple operation while having barely any side reaction or sub-product. More specifically, the present invention pertains to a manufacturing method for phosphonate esters in which secondary phosphonate esters and alkene compounds are reacted in a transition metal catalyst. In addition the present invention relates to a new manufacturing method for allylphosphonate esters in which secondary cyclic phosphonate esters and 1,3-diene compounds are reacted in a palladium catalyst.Type: GrantFiled: May 26, 2004Date of Patent: January 23, 2007Assignees: Japan Science and Technology Corporation, National Institute of Advanced Industrial Science and TechnologyInventors: Li-Biao Han, Farzad Mirzaei, Masato Tanaka
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Patent number: 7135583Abstract: A novel process for preparation of alkenylphosphine oxides or alkenylphosphinic acid esters provided by which the objective compounds can be easily, safely and efficiently synthesized and easily separated and purified with little formation of by-products. Specifically, a process of conducting the addition reaction of an easily available secondary phosphine oxide or hydrogen phosphinic acid ester with an acetylene compound with a catalyst containing a Group 9 or 10 metal of the periodic table to thereby obtain the corresponding alkenylphosphine oxide or alkenylphosphinic acid ester.Type: GrantFiled: February 12, 2002Date of Patent: November 14, 2006Assignees: Japan Science and Technology Corporation, National Institute of Advanced Industrial Science & TechnologyInventors: Li-biao Han, Chang-qiu Zhao, Masato Tanaka
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Patent number: 6949667Abstract: Novel alkenylphosphonic acid esters of the following general formula (I): R1CH?CR2[P(O)(OCR3R4CR5R6O)]??(I) and a simple process for the preparation thereof are provided by the use of secondary cyclic phosphonic acid esters as the starting material.Type: GrantFiled: December 28, 2000Date of Patent: September 27, 2005Assignee: National Institute of Advanced Industrial Science and TechnologyInventors: Li-Biao Han, ChangQiu Zhao, Masato Tanaka
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Publication number: 20050107599Abstract: The invention provides a process by which rare earth metal ions can be efficiently extracted by easy operation, and effective extracting reagents for the process. Specifically, phosphonamides represented by the general formula [1]; a process for producing the same; reagents for extracting rare earth metal ions, containing the phosphonamides; and a process for extraction of rare earth metal ions with the phosphonamides: [1] wherein R1 is alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, aralkyl, or a heterocyclic group, with the proviso that each group may be substituted; R2 is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, aralkyl, or a heterocyclic group, with the proviso that each group may be substituted; R3 is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, aralkyl, or a heterocyclic group, with the proviso that each group may be substituted, or the two R3s may be united to form alkylene, cycloalkylene, or arylene.Type: ApplicationFiled: March 3, 2003Publication date: May 19, 2005Inventors: Yoshikazu Makioka, Teruyuki Hayashi, Masato Tanaka, Li-Biao Han
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Publication number: 20040220422Abstract: The present invention relates to a new manufacturing method for phosphonate esters, which have utility as a carbon-carbon binding formation agent, as well as a synthesis intermediate for biologically active substances such as medical drugs and agri-chemicals.Type: ApplicationFiled: May 26, 2004Publication date: November 4, 2004Inventors: Li-Biao Han, Farzad Mirzaei, Masato Tanaka
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Patent number: 6765107Abstract: The present invention relates to a new manufacturing method for phosphonate esters, which have utility as a carbon-carbon binding formation agent, as well as a synthesis intermediate for biologically active substances such as medical drugs and agri-chemicals. Specifically the present invention relates to a new industrially advantageous manufacturing method for phosphonate esters in which the phosphonate esters of the subject can be efficiently obtained with a high yield rate through a simple operation while having barely any side reaction or sub-product. More specifically, the present invention pertains to a manufacturing method for phosphonate esters in which secondary phosphonate esters and alkene compounds are reacted in a transition metal catalyst. In addition the present invention relates to a new manufacturing method for allylphosphonate esters in which secondary cyclic phosphonate esters and 1,3-diene compounds are reacted in a palladium catalyst.Type: GrantFiled: July 30, 2002Date of Patent: July 20, 2004Assignees: National Institute of Advanced Industrial Science and Technology, Japan Science and Technology AgencyInventors: Li-Biao Han, Farzad Mirzaei, Masato Tanaka
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Publication number: 20040092752Abstract: A novel, optically active alkenylphosphinic acid ester having chirality on a phosphorus atom; and a simple process for producing the ester. An optically active, hydrogen phosphinic acid ester is reacted with an acetylene compound in the presence of a catalyst containing a metal of group 9 or 10 of the periodic table to thereby obtain a novel, optically active alkenylphosphinic acid ester which has chirality on a phosphorus atom and is represented by the following general formula [1] and/or [2].Type: ApplicationFiled: September 8, 2003Publication date: May 13, 2004Inventors: Li-Biao Han, Chang-Qiu Zhao, Masato Tanaka
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Publication number: 20040059146Abstract: A novel process for preparation of alkenylphosphine oxides or alkenylphosphinic acid esters provided by which the objective compounds can be easily, safely and efficiently synthesized and easily separated and purified with little formation of by-products. Specifically, a process of conducting the addition reaction of an easily available secondary phosphine oxide or hydrogen phosphinic acid ester with an acetylene compound with a catalyst containing a Group 9 or 10 metal of the periodic table to thereby obtain the corresponding alkenylphosphine oxide or alkenylphosphinic acid ester.Type: ApplicationFiled: August 8, 2003Publication date: March 25, 2004Inventors: Li-biao Han, Chang-qiu Zhao, Masato Tanaka
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Publication number: 20030166612Abstract: Novel alkenylphosphonic acid esters of the following general formula (I):Type: ApplicationFiled: December 4, 2002Publication date: September 4, 2003Inventors: Li-Biao Han, ChangQiu Zhao, Masato Tanaka
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Publication number: 20030105345Abstract: The present invention relates to a new manufacturing method for phosphonate esters, which have utility as a carbon-carbon binding formation agent, as well as a synthesis intermediate for biologically active substances such as medical drugs and agri-chemicals.Type: ApplicationFiled: July 30, 2002Publication date: June 5, 2003Inventors: Li-Biao Han, Farzad Mirzaei, Masato Tanaka
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Patent number: 6191298Abstract: A phosphonic acid ester compound of the formula: R1C(SR3)═CHP(═O)(OR2)2 or [P(═O)(OR2)2]CH═C(SR3)—R4—C(SR3)═CH[P(═O)(OR2)2] wherein R1 represents a monovalent group selected from hydrogen, alkyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkenyl and silyl, R2 and R3 each represent aryl and R4 represents alkylene or cycloalkylene. The ester compound is produced by reaction of an acetylene compound, R1C≡CH or HC≡C—R4—C≡CH, with with a phosphorothioate, (R2O)2P(═O)SR3, in the presence of a palladium complex catalyst.Type: GrantFiled: March 9, 2000Date of Patent: February 20, 2001Assignee: Agency of Industrial Science and TechnologyInventors: Li-Biao Han, Masato Tanaka
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Patent number: 6111127Abstract: A process for the preparation of an unsaturated phosphonic acid ester of the formula:R.sup.1 CH.dbd.C(R.sup.2)P(.dbd.O)(OR.sup.3).sub.2wherein an acetylene compound of the formula:R.sup.1 C.tbd.CR.sup.2is reacted with a secondary phosphite of the formula:HP(.dbd.O)(OR.sup.3).sub.2in the presence of a palladium complex catalyst. The process is characterized in that the reaction is performed in the presence of water or in that the palladium complex catalyst contains, as a ligand, a 1,3-bisphosphinopropane of the formula: ##STR1## wherein R.sup.4, R.sup.5, R.sup.6 and R.sup.7 stand, independently from each other, for an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group.Type: GrantFiled: September 13, 1999Date of Patent: August 29, 2000Assignees: Agency of Industrial Science & Technology, Masato TanakaInventors: Masato Tanaka, Li-Biao Han
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Patent number: 5977394Abstract: Disclosed is a silyl thioalkene compound, as a class of organosilicon compounds, represented by the general formulaR(--CSAr.dbd.CHSiX.sub.3).sub.n,in which the subscript n is 1 or 2, R is, when n is 1, a hydrogen atom or unsubstituted or substituted monovalent hydrocarbon group or, when n is 2, a divalent hydrocarbon group, Ar is an unsubstituted or nucleus-substituted aromatic monovalent aromatic hydrocarbon group and X is a halogen atom, a monovalent hydrocarbon group or hydrocarbyloxy group, having usefulness as an intermediate in the synthesis of various precision organic chemicals. The compound, of which X is a halogen atom X.sup.1, can be prepared, for example, by the reaction of an alkyne compound of the general formulaR(--C.tbd.CH).sub.n,with a silyl sulfide compound of the general formulaArS--SiX.sup.1.sub.3,in the presence of a platinum complex catalyst.Type: GrantFiled: March 3, 1999Date of Patent: November 2, 1999Assignee: Japan as represented by Director General of Agency of Industrial Science and TechnologyInventors: Li-Biao Han, Masato Tanaka
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Patent number: 5693826Abstract: An unsaturated phosphonic ester is produced by reaction of an acetylene compound with a secondary phosphite in the presence of a palladium complex catalyst.Type: GrantFiled: August 19, 1996Date of Patent: December 2, 1997Assignee: Director-General Of Agency Of Industrial Science And TechnologyInventors: Masato Tanaka, Li-Biao Han