Oxirane Ring Containing Patents (Class 549/215)
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Patent number: 6107504Abstract: There are herein disclosed a siloxane compound represented by the formula (1) ##STR1## wherein R.sup.2 is a methyl group or a phenyl group; R.sup.3 is an alkyl group having 1 to 6 carbon atoms or A; l is an integer of 0 to 500; m is an integer of 0 to 1,000; n is an integer of 0 to 500; p is an integer of 0 to 2; and A is an ester group represented by the formula (2) ##STR2## wherein R.sup.6 is hydrogen or the methyl group; s is an integer of 0 to 100; and R.sup.1 is a branched or a straight-chain alkyl group having 1 to 30 carbon atoms, a cyclohexyl group, a phenyl group, a benzyl group, a glycidyl group, or a fluorine-containing organic group represented by the formula (3) ##STR3## wherein R.sup.4 is a saturated hydrocarbon having 0 to 6 carbon atoms, and when 0 is selected, R.sup.4 is not present; R.sup.5 is hydrogen or fluorine; a is 0 or 1; and b and c are each an integer of 0 to 20, but for a, b and c, 0 is not simultaneously selected, and a preparation method of the above siloxane compound.Type: GrantFiled: October 28, 1998Date of Patent: August 22, 2000Assignee: Chisso CorporationInventors: Yuuichi Yamamoto, Koichi Ayama
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Patent number: 6100408Abstract: The invention relates to a process for preparing 3-glycidyloxypropyltrialkoxysilanes of the general formulaCH.sub.2 (O)CHCH.sub.2 --O--(CH.sub.2).sub.3 Si(OR).sub.3 (I),in which R is an alkyl radical, by reacting allyl glycidyl etherCH.sub.2 (O)CHCH.sub.2 --O--CH.sub.2 CH.dbd.CH.sub.2 (II),with a trialkoxysilane of the general formulaHSi(OR).sub.3 (III),in which R is again an alkyl radical, in a heterogeneous, platinum-catalyzed hydrosilylation reaction, where the catalyst employed is a platinum(0) catalyst on a nonmetallic support.Type: GrantFiled: February 9, 1999Date of Patent: August 8, 2000Assignee: Huels AktiengesellschaftInventors: Jaroslaw Monkiewicz, Stefan Bade, Uwe Schoen
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Patent number: 6069259Abstract: A composition relating to an oligomeric alkoxy siloxane substituted with polymerizible epoxy or 1-alkenyl groups, and a process for the production of that composition, are disclosed. The process entails a hydrolysis-condensation oligomerization of an epoxy- or 1-alkenyl ether-functional trialkoxy silane, catalyzed by an ion exchange resin, and separation of the resin from the resulting oligomer.Type: GrantFiled: February 6, 1998Date of Patent: May 30, 2000Assignee: Rensselaer Polytechnic InstituteInventor: James Vincent Crivello
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Patent number: 6060620Abstract: A method of manufacturing acyloxysilane compounds having functional groups bonded to a silicon atom via Si--C bonds comprising reacting in a hydrosilation reaction an unsaturated compound (a) selected from the group consisting of (i) styrene or styrene derivative, (ii) vinylsilane compound, (iii) siloxane compound having a vinyl group bonded directly to a silicon atom, (iv) epoxy-functional olefin, (v) diene compound, (vi) allyl compound described by formula CH.sub.2 .dbd.CHCH.sub.2 X, where X is a halogen atom, an alkoxy group, or an acyloxy group, (vii) olefin compound having a terminal vinyl group, and (viii) acetylene-type compound with a silicon compound (b) that contains hydrogen atom bonded to the silicon atom and acyloxy group in the presence of a platinum catalyst.Type: GrantFiled: September 14, 1999Date of Patent: May 9, 2000Assignee: Dow Corning Asia, Ltd.Inventor: Mamoru Tachikawa
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Patent number: 6001561Abstract: Chemiluminescent electron-rich aryl-substituted 1,2-dioxetane compounds are disclosed in which the aryl group is poly-substituted with suitable electron-donating groups such that the light-emitting pattern of the molecule results in a very high luminescent count, thus providing for a sensitive and precise assay for haptens, analytes, polynucleotides and the like. These substituted aryl-containing 1,2-dioxetane compounds can be used as direct labels in an immunoassay or when derivatized with an appropriate leaving group, can be used as a substrate for a enzyme immunoassay. The unusual chemiluminescence of the compounds allows the timing of the luminescent reaction to be exactly controlled.Type: GrantFiled: May 9, 1995Date of Patent: December 14, 1999Assignee: Abbott LaboratoriesInventors: Nai-Yi Wang, Roger C. Hu
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Patent number: 6001659Abstract: Chemiluminescent electron-rich aryl-substituted 1,2-dioxetane compounds are disclosed in which the aryl group is poly-substituted with suitable electron-donating groups such that the light-emitting pattern of the molecule results in a very high luminescent count, thus providing for a sensitive and precise assay for haptens, analytes, polynucleotides and the like. These substituted aryl-containing 1,2-dioxetane compounds can be used as direct labels in an immunoassay or when derivatized with an appropriate leaving group, can be used as a substrate for a enzyme immunoassay. The unusual chemiluminescence of the compounds allows the timing of the luminescent reaction to be exactly controlled.Type: GrantFiled: May 9, 1995Date of Patent: December 14, 1999Assignee: Abbott LaboratoriesInventors: Nai-Yi Wang, Roger C. Hu
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Patent number: 5981511Abstract: The current invention discloses hydroxyamidino derivatives useful as nitric oxide synthase inhibitors.Type: GrantFiled: March 5, 1997Date of Patent: November 9, 1999Assignee: G.D. Searle & Co.Inventors: Rolando E. Gapud, Timothy J. Hagen, Ann E. Hallinan, Donald W. Hansen, Jr., Robert E. Manning, Suzanne Metz, Barnett S. Pitzele, Foe S. Tjoeng, Mihaly V. Toth, R. Keith Webber
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Patent number: 5973176Abstract: The invention relates to hydrolyzable fluorinate silanes, methods of their roduction and of their use for producing silicic acid polycondensates and hetero silicic acid polycondensats The silanes in accordance with the invention are of the general formula: {[R'-(Y).sub.e ].sub.c+1 (C.sub.6 F.sub.4-c) (C.sub.6 F.sub.4).sub.d }.sub.f SiR.sub.a X.sub.b (I) in which the groups and indices are identical or different and have the following meaning:R=alkyl, alkenyl, aryl, alkylaryl or arylalkyl, substituted if required, each with 1 to 15 carbon atoms, whereby the groups may be interrupted by oxygen or sulfur atoms, ester, carbonyl, amide or amino groups;R'=I, Br, Cl (if d.noteq.0), F (if d.noteq.0), H (if X.noteq.H or R.noteq.methyl or e=1) or an organic group with 1 to 50 carbon atoms;X=hydrogen, halogen except fluorine, hydroxy, alkoxy, acyloxy, alkylcarbonyl, alkoxycarbonyl or NR".sub.Type: GrantFiled: April 3, 1997Date of Patent: October 26, 1999Assignee: Fraunhofer-Gesellschaft zur Foerderung der angewandten Forschung e.V.Inventors: Christof Roscher, Michael Popall, Birke-E. Olsowski
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Patent number: 5945408Abstract: The current invention discloses hydroxyamidino derivatives useful as nitric oxide synthase inhibitors.Type: GrantFiled: August 8, 1996Date of Patent: August 31, 1999Assignee: G.D. Searle & Co.Inventors: R. Keith Webber, Foe S. Tjoeng, Robert E. Manning
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Patent number: 5942638Abstract: A synthetic process for the selective preparation of reactive polyhedral oligomeric silsesquioxanes (POSS) as well as polyhedral oligomeric silicate (POS) (spherosilicate) is provided. The method claimed herein employs metal catalyzed metathesis reactions for the selective reaction of .alpha.-olefin containing polyhedral oligomeric silsesquioxanes or silicates with olefinic reagents bearing functionalities useful for grafting reactions, polymerization chemistry and sol-gel processes. The use of metal catalyzed metathesis chemistry to form both linear or network polyhedral silsesquioxane polymers directly from .alpha.-olefin-containing polyhedral oligomeric silsesquioxanes is also described.Type: GrantFiled: January 5, 1998Date of Patent: August 24, 1999Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Joseph D. Lichtenhan, Joseph J. Schwabb, Frank J. Feher, Daravong Soulivong
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Patent number: 5939576Abstract: A synthetic process for the selective preparation of reactive polyhedral oligomeric silsesquioxanes (POSS) as well as polyhedral oligomeric silicate (POS) (spherosilicate) is provided. The inventive process employs the use of metal catalyzed hydrosilylation reactions for the selective reaction of silane containing polyhedral oligomeric silsesquioxanes or silicates with olefinic reagents bearing functionalities useful for grafting reactions, polymerization chemistry and sol-gel processes. The invention also discloses metal-catalyzed hydrosulfidation reactions and metal-catalyzed hydrophosphidation reacttions for functionalization of polycyclic silicones.Type: GrantFiled: January 5, 1998Date of Patent: August 17, 1999Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Joseph D. Lichtenhan, Joseph J. Schwab, Frank J. Feher, Daravong Soulivong
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Patent number: 5919956Abstract: A process for the manufacture of an optionally protected 4,8,8-trimethyl-1-oxaspiro?2.5!oct-4-en-6-ol (I) starting from protected 4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one (II) comprises reacting the protected compound (II) with dihalomethyllithium and, if desired, cleaving off the protecting group from the thus-obtained protected 4,8,8-trimethyl-1-oxaspiro?2.5!oct-4-en-6-ol. The dihalomethyllithium can be produced in situ by reacting a dihalomethane with a lower alkyllithium in the presence of the compound of formula II. Preferably, protected (S)-4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one is converted into protected (3S,6S)-4,8,8-trimethyl-1-oxaspiro?2.5!oct-4-en-6-ol in this manner. Both the starting material (II) and the end product (I) of the process in accordance with the invention are known, valuable intermediates for the manufacture of carotenoids.Type: GrantFiled: September 29, 1997Date of Patent: July 6, 1999Assignee: Roche Vitamins Inc.Inventors: Hans Hilpert, Erich Widmer
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Patent number: 5917075Abstract: The hydrolyzable and polymerizable silanes have the formula I, ##STR1## wherein X is hydrogen, a halogen, a hydroxy, an alkoxy group, an acyloxy oup, an alkylcarbonyl group, an alkoxycarbonyl group or --NR.sup.2.sub.2 group; wherein R.sup.Type: GrantFiled: December 22, 1997Date of Patent: June 29, 1999Assignee: Fraunhofer-Gesellschaft zur Foerderung der angewandten Forschung, e.V.Inventor: Herbert Wolter
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Patent number: 5883214Abstract: Epoxysilanes having epoxide groups bonded via SiC are obtained by reaction of epoxyalkoxysilanes with silanols. The transparent siloxane mixtures containing epoxide can be employed directly as resin components for mixing with epoxy resins for casting resin applications.Type: GrantFiled: February 23, 1996Date of Patent: March 16, 1999Assignee: Siemens AktiengesellschaftInventors: Ernst Wipfelder, Klaus Hohn
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Patent number: 5869699Abstract: A new class of stable dioxetanes bears a polycyclic stabilizing group and aryloxy moiety, the oxygen atom of which is provided with a protective group which can be removed by an enzymatic or chemical trigger admixed with the dioxetane. The polycyclic stabilizing group is preferably spiroadamantane. The group further bears an alkoxy, aryloxy, aralkyloxy or cycloalkyloxy moiety which is partially or completely substituted with halogens, particularly fluorine and chlorine. Proper selection of electron active groups on the stabilizing moiety, the aryl group and the OR group yields enhanced enzyme kinetics, superior light intensity and excellent detection sensitivity in various assays.Type: GrantFiled: June 10, 1997Date of Patent: February 9, 1999
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Patent number: 5869698Abstract: Dioxetanes which couple with organic and biological molecules of the formula: ##STR1## wherein X is a leaving group which is removed by an `activating agent to produce light, wherein A is a coupling substituent, Ar is a substituent selected from the group consisting of phenyl and naphthyl to provide a label are described. R.sub.1 is an optional linker substituent and can have between 1 and 30 carbon atoms with some of the carbon atoms being oxygen, sulfur, nitrogen or phosphorus. Ar as phenyl is preferred. The dioxetane coupled molecules are useful in assays of all types where luminescence can be used as an indicator.Type: GrantFiled: August 12, 1997Date of Patent: February 9, 1999Assignee: Board of Governors of Wayne State UniversityInventors: Arthur P. Schaap, Louis J. Romano, Jaidev S. Goudar
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Patent number: 5811504Abstract: Monomers of formula (I) ##STR1## where ##STR2## is a mesogen, ##STR3## is a spacer, and --X is a group having an epoxy function exhibit a reduced tendency to undergo self-condensation via addition polymerization and afford liquid crystalline polymers upon condensation with a crosslinking agent.Type: GrantFiled: August 3, 1995Date of Patent: September 22, 1998Assignee: Cornell Research Foundation, Inc.Inventors: Atsushi Shiota, Christopher K. Ober
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Patent number: 5756767Abstract: The hydrolyzable and polymerizable silanes have the formula I, ##STR1## wherein X is hydrogen, a halogen, a hydroxy, an alkoxy group, an acyloxy group, an alkylcarbonyl group, an alkoxycarbonyl group or --NR.sup.2.sub.2 group; wherein R.sup.Type: GrantFiled: May 15, 1997Date of Patent: May 26, 1998Inventor: Herbert Wolter
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Patent number: 5703246Abstract: A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I) wherein, X is oxygen, NR.sup.4 or CHR.sup.5 ; R.sup.1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R.sup.2 is hydrogen, alkyl, aryl, heteroaromatic, CO.sub.2 R.sup.8, CHR.sup.14 NHR.sup.13, heterocyclic or cycloalkyl; or R.sup.1 and R.sup.2 join together to form a cycloalkyl ring; R.sup.3 is hydrogen, alkyl, aryl, heteroaromatic, CO.sub.2 R.sup.8, R.sup.8.sub.3 Sn, CONR.sup.8 R.sup.9 or trimethylsilyl; R.sup.4 and R.sup.5 are, independently, alkyl, cycloalkyl, aryl, heteroaromatic, SO.sub.2 R.sup.8, SO.sub.3 R.sup.8, COR.sup.8, CO.sub.2 R.sup.8, CONR.sup.8 R.sup.9 or CN, or R.sup.4 can also be P(O)(aryl).sub.2 ; R.sup.8 and R.sup.9 are independently alkyl, aryl or arylalkyl; R.sup.13 and R.sup.14 are independently hydrogen, alkyl or aryl; the process comprising reacting a mixture of a compound of formula (II), wherein R.sup.1, R.sup.2 and X are as defined above, and a sulphide of formula SR.sup.6 R.Type: GrantFiled: March 15, 1996Date of Patent: December 30, 1997Assignee: Zeneca LimitedInventors: Varinder Kumar Aggarwal, Hesham Nimer Hasan Abdel-Rahman, Hee Yoon Lee
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Patent number: 5693734Abstract: Organosilicon compounds containing furanyl groups which contain units of the formula ##EQU1## in which R is identical or different and is a hydrogen atom or monovalent, SiC-bonded, aliphatically saturated, optionally substituted hydrocarbon radical, which can be interrupted by oxygen atoms,R.sup.1 is identical or different and is an optionally substituted hydrocarbon radical having 1 to 8 carbon atoms, which can be interrupted by 1 to 3 oxygen atoms.A is identical or different and is an SiC-bonded furanyl radical of the formula ##STR1## where R.sup.2 has the meaning given above for the radical R and R.sup.3 is a divalent hydrocarbon radical having 2 to 30 carbon atoms, which can contain one or more groups, chosen from the group consisting of ##STR2## a is 0, 1, 2 or 3, b is 0, 1 or 2 andc is 0, 1 or 2,with the proviso that the sum a+b+c is less than or equal to 3 and the organosilicon compound contains at least one radical A per molecule.Type: GrantFiled: June 27, 1995Date of Patent: December 2, 1997Assignee: Wacker-Chemie GmbHInventors: Christian Herzig, Bernward Deubzer, Martina Bloechl, Inge Seeger-Feichtinger
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Patent number: 5674965Abstract: A compound of Formula (1): ##STR1## wherein: X is E--(L.sup.4 O).sub.m --CO--(T).sub.p ;Y is --Si(R.sup.1).sub.3 or X as defined above;T is O, CH.sub.2 or NR.sup.2 ;P is 0 or 1;q is 0, 1, 2, 3 or 4;E comprises an alicyclic or aliphatic epoxy group;each L.sup.1, L.sup.2, L.sup.3 and L.sup.4 independently is an unsubstituted or substituted alkylene group of 1 to 6 carbon atoms wherein any substitution is selected from methyl, amino, ester, hydroxy and ester groups;m is 0 or 1;each R.sup.1 when Y is --Si(R.sup.1).sub.3 is independently unsubstituted alkyl or substituted alkoxy provided that at least one R.sup.1 is unsubstituted alkoxy; andeach R.sup.2 independently is H, --L.sup.1 X unsubstituted or substituted alkyl wherein any substitution is selected from poly(oxyalkylene), epoxy and hydrolyzable silyl groups, or --CONH(C.sub.1-20 -alkyl). The compounds are useful in coating compositions and films and coatings formed therefrom.Type: GrantFiled: May 12, 1995Date of Patent: October 7, 1997Assignee: Zeneca LimitedInventors: John Gerard Carey, John Christopher Padget, David Alan Pears
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Patent number: 5663397Abstract: There is disclosed a method of preparing cyclic silyl enol ethers (1-oxa-2-sila-5-cyclohexenes), comprising reacting a silacyclobutane with an acid halide in the presence of a palladium catalyst and an organic base. There is also disclosed novel cyclic silyl enol ethers obtained by the above method. The above cyclic silyl enol ethers belong to a new class of silyl enol ethers which are useful in the production of medicines and agricultural chemicals, and they can be used as intermediates of fine chemicals or as various reagents for fine synthesis.Type: GrantFiled: September 13, 1996Date of Patent: September 2, 1997Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Hiroshi Yamashita, Masato Tanaka
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Patent number: 5650474Abstract: A process for preparing an organic functional group-containing organopolysiloxane of the following average compositional formula (1)YmR.sup.1 nSi(OR.sup.2)pO.sub.(4-m-n-p)/2 (1)wherein Y represents an organic group having a functional group, R.sup.1 represents at least one monovalent substituted or unsubstituted hydrocarbon group, R.sup.2 represents a hydrogen atom, an alkenyl group and/or an alkenyl group, 0<m.ltoreq.1, 0.ltoreq.n<2, and 0.ltoreq.p.ltoreq.2 provided that 0<m+n+p.ltoreq.3. The organopolysiloxane is obtained by subjecting an organic functional group-containing alkoxysilane, with or without a functional group-free alkoxysilane, siloxane and/or silicone obtained from the group-free alkoxysiloxane and/or siloxane, to hydrolysis and polycondensation in the presence of a substantially neutral fluorine-containing compound. The functional group includes an epoxy group, a (meth)acryloxy group, a mercapto group and the like.Type: GrantFiled: February 16, 1996Date of Patent: July 22, 1997Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaaki Yamaya, Kazuyuki Matsumura, Yuji Yoshikawa
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Patent number: 5629437Abstract: The invention is directed to water soluble silane compositions that are essentially alcohol free comprising compounds of the structure:(RO).sub.3-x (HO).sub.x Si(CH.sub.2).sub.3 (OCH.sub.2 CH.sub.2).sub.b OH(Ia ){(RO).sub.2-y (HO).sub.y Si(CH.sub.2).sub.3 (OCH.sub.2 CH.sub.2).sub.b O}.sub.z (IIa)wherein x ranges from 1 to 3, b ranges from 1 to 30, y is 0 or 1, and z ranges from 1 to 3, and R is an aryl or alkyl having from 1 to 10 carbon atoms. The invention further comprises methods for forming such compounds and for their use in preparing water soluble silane compositions by reaction with relative insoluble silane compounds terminated in functional groups selected from the group comprising epoxies, vinyls, mercaptos and acrylates.Type: GrantFiled: January 30, 1996Date of Patent: May 13, 1997Assignee: Huls America Inc.Inventors: Loren Linder, Joel Zazyczny
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Patent number: 5616763Abstract: A hydrosilation process where a silicon hydride is reacted with an unsaturated reactant in the presence of a platinum catalyst and an aldehyde accelerator. The aldehyde accelerators are especially useful for facilitating the hydrosilation of unsaturated reactants where the unsaturation is in the internal portion of the reactant's structure, for example, as in cyclopentene and cyclohexene.Type: GrantFiled: January 29, 1996Date of Patent: April 1, 1997Assignee: Dow Corning CorporationInventors: Howard M. Bank, Gary T. Decker
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Patent number: 5616756Abstract: There is disclosed an organosilicon compound which contains a silicon-bonded functional group at each molecular chain terminal as well as a terminal -SiH group on a side chain branching from the main chain, said functional group being selected from amino-functional organic groups, epoxy-functional organic groups, hydroxyl group or a group obtained by substituting active hydrogen in the preceding groups with triorganosilyl group.Type: GrantFiled: May 29, 1996Date of Patent: April 1, 1997Assignee: Dow Corning Toray Silicone Co., Ltd.Inventor: Hisataka Nakashima
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Patent number: 5614640Abstract: This invention relates to novel alicyclic epoxy-functional siloxanes. The invention also relates to a method for the preparation of these epoxy-functional siloxanes. The epoxy functional siloxanes of this invention can be added to photocurable compositions which when exposed to ultraviolet radiation will yield a highly releasing, very printable/writable, and highly water-repellent cured film.Type: GrantFiled: March 21, 1996Date of Patent: March 25, 1997Assignee: Dow Corning Toray Silicone Co., Ltd.Inventor: Tadashi Okawa
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Patent number: 5603868Abstract: Chemiluminescent electron-rich aryl-substituted 1,2-dioxetane compounds are disclosed in which the aryl group is poly-substituted with suitable electron-donating groups such that the light-emitting pattern of the molecule results in a very high luminescent count, thus providing for a sensitive and precise assay for haptens, analytes, polynucleotides and the like. These substituted aryl-containing 1,2-dioxetane compounds can be used as direct labels in an immunoassay or when derivatized with an appropriate leaving group, can be used as a substrate for a enzyme immunoassay. The unusual chemiluminescence of the compounds allows the timing of the luminescent reaction to be exactly controlled.Type: GrantFiled: October 30, 1992Date of Patent: February 18, 1997Assignee: Abbott LaboratoriesInventors: Nai-Yi Wang, Roger C. Hu
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Patent number: 5583194Abstract: The invention provides a method for making a curable epoxysilicone composition through the hydrosilation reaction between an ethylenically unsaturated epoxide and an SiH-containing silicone to produce an epoxysilicone product, and catalyzed by a quaternary ammonium, phosphonium or arsonium hexahaloplatinate which does not promote the oxirane ring-opening reaction of either the ethylenically unsaturated epoxide starting material or the epoxysilicone product. The invention also provides for a curable epoxysilicone composition made by the above method.Type: GrantFiled: February 14, 1994Date of Patent: December 10, 1996Assignee: General Electric CompanyInventors: James V. Crivello, Mingxin Fan
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Patent number: 5512640Abstract: Disclosed is a method of producing an epoxy-modified silicone, which comprises causing a reaction between (A) 100 parts of an ethylenic unsaturated group-containing epoxide and (B) from 50 to 40,000 parts of an organohydrogenpolysiloxane and/or an organohydrogensilane in the presence of (C) from 0.00001 to 0.5 part by weight, on a platinum basis, of a platinum compound as catalyst and (D) from 0.1 to 1,000 parts by weight of an aliphatic alcohol containing from 1 to 10 carbon atoms.Type: GrantFiled: November 7, 1994Date of Patent: April 30, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yoshihito Osawa, Hiroshi Ohashi
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Patent number: 5484950Abstract: A process for the selective monoadditon of an olefin or acetylene to a siloxane which contains two reactive Si--H bonds to produce a product in which only one of the two Si--H functions has added across the olefin or acetylene is disclosed. A process for making unsymmetrical siloxanes from symmetrical dihydrosiloxanes and products of both of these processes are also disclosed. Products are represented by the formula I in which R.sup.1 and R.sup.Type: GrantFiled: December 21, 1992Date of Patent: January 16, 1996Assignee: Polyset Company, Inc.Inventor: James V. Crivello
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Patent number: 5478954Abstract: Process for preparing highly pure enantiomers of oxirane alcohols, which comprises recrystallizing a mixture of the isomeric oxirane alcohols, in which the desired enantiomer is present in an excess of at least 60% ee, in a solvent or solvent mixture at a temperature just below the melting point of the oxirane alcohol.Oxirane alcohols prepared according to the invention are distinguished by high enantiomer purity. Ferroelectric liquid crystals, which contain highly pure enantiomers of oxirane alcohols according to the invention and/or derivatives derived therefrom, have particularly short switching times.Type: GrantFiled: July 28, 1993Date of Patent: December 26, 1995Assignee: Hoechst AktiengesellschaftInventor: Javier Manero
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Patent number: 5442026Abstract: The invention provides a method for making a curable epoxysilicone composition through the hydrosilation reaction between an ethylenically unsaturated epoxide and an SiH-containing silicone to produce an epoxysilicone product, and catalyzed by a rhodium containing selective catalyst which does not promote the oxirane ring-opening reaction of either the ethylenically unsaturated epoxide starting material or the epoxysilicone product. The rhodium containing selective catalyst has the general formula[R.sub.4 M].sup.+ [RhCl.sub.3 Br].sup.-wherein M is phosphorous or nitrogen and R is an organic radical comprising a C.sub.1-18 linear alkyl radical, aryl, alkaryl or aralkyl radical.Type: GrantFiled: November 10, 1994Date of Patent: August 15, 1995Assignee: General Electric CompanyInventors: James V. Crivello, Mingxin Fan
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Patent number: 5420323Abstract: The present invention relates to allylakylsilanes represented by the general formula (III) and their preparation methods by reacting allylsilanes represented by the formula I with olefin compounds represented by the formula II in the presence of hydrosilation catalysts such as chloroplatinic acid, platinum on silica, tributyl amine and Pd, Rh, Ni metals. ##STR1## wherein X represents independently chloro or alkoxy (C.sub.1-C.sub.4) and R is selected from the group consisting of Ph, CH.sub.2 Cl, C.sub.n H.sub.2n CH.sub.3 (n=0-15), Si(Me).sub.m Cl.sub.3-m (m=0-3), CF.sub.3, CH.sub.2 CF.sub.3, CN, CH.sub.2 CN, ##STR2## CH.sub.2 Si(Me).sub.m CL.sub.3-m (m=0-3), Si(Me).sub.m (OR.sup.1).sub.3-m (m=0-3), CH.sub.2 Si(Me).sub.m (OR.sup.1).sub.3-m (m=0-3), (wherein Me is methyl and R.sup.1 is methoxy or ethoxy group), Ph-CH.sub.2 Cl, and cyclohexenyl group.Type: GrantFiled: September 8, 1994Date of Patent: May 30, 1995Assignee: Korea Institute of Science and TechnologyInventors: Il N. Jung, Bok R. Yoo, Bong W. Lee, Mi-Yeon Suk
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Patent number: 5391794Abstract: The present invention relates to trissilylalkanes represented by formula (X), (XI), (XII), (XIII), (XIV), (XV), (XVI) and (XVII), and preparation methods thereof. ##STR1## wherein X can be Cl, OR.sup.1 (R.sup.1 =C.sub.1 -C.sub.4 alkyl) or OAc, and R.sup.2 can be Ph, CH.sub.2 Cl, C.sub.n H.sub.2n CH.sub.3 (n=0-15), Si(Me).sub.m Cl.sub.3-m, (m=0-3), CF.sub.3, CN, CH.sub.2 CN, CH.dbd.CH.sub.2, (CH.sub.2).sub.4 CH.dbd.CH.sub.2, ##STR2## Ph-CH.sub.2 Cl or cyclohex-3-enyl group.Type: GrantFiled: January 27, 1994Date of Patent: February 21, 1995Assignee: Korea Institute of Science and TechnologyInventors: Il N. Jung, Gyu H. Lee, Mi Y. Suk, Seung H. Yeon
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Patent number: 5387698Abstract: The invention provides a method for making a curable epoxysilicone composition through the hydrosilation reaction between an ethylenically unsaturated epoxide and an SiH-containing silicone to produce an epoxysilicone product, and catalyzed by a rhodium containing selective catalyst which does not promote the oxirane ring-opening reaction of either the ethylenically unsaturated epoxide starting material or the epoxysilicone product. The invention also provides for a curable epoxysilicone composition made by the above method for the catalyst, and two methods of making the catalyst.Type: GrantFiled: June 11, 1992Date of Patent: February 7, 1995Assignee: General Electric CompanyInventors: James V. Crivello, Mingxin Fan
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Patent number: 5386050Abstract: The present invention relates to a process for preparing (2-arylpropyl)alkylsilanes represented by the formula III by reacting (2-arylpropyl)silanes represented by the formula I with olefin compounds represented by the formula II in the presence of hydrosilation catalysts such as chloroplatanic acid, platinum on silica, tributylamine and Pd, Rh, Ni metals. ##STR1## Olefin compounds(cyclohexene or CH.sub.2 =CH--R.sup.3) (II) ##STR2## In the formulas (I) and (III), R.sup.1 and R.sup.2 represent independently hydrogen, alkyl(C.sub.1 -C.sub.4), fluoro, chloro or bromo; and Ar represents phenyl ring, naphthalene ring, or biphenyl ring. X represents hydrogen or chloro group. In the formula (III), R represents --(CH.sub.2 CH.sub.2)--R.sup.3, sec-butyl, or cyclohexyl wherein R.sup.3 =Ph, CH.sub.2 Cl, C.sub.n H.sub.2n CH.sub.3 (n=0-15), CH.sub.2 Si(Me).sub.m Cl.sub.3-m (m=O-3), (CH.sub.2).sub.2 Si(Me).sub.m (OMe).sub.3-m (m=O-3), (CH.sub.2).sub.3 Si(Me).sub.m (OMe).sub.3-m (m=O-3), Si(Me).sub.m Cl.sub.3-m (m=0-3), CF.Type: GrantFiled: January 3, 1994Date of Patent: January 31, 1995Assignee: Korea Institute of Science and TechnologyInventors: Il N. Jung, Bok R. Yoo, Bong W. Lee, Seung H. Yeon
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Patent number: 5362887Abstract: Novel fluorine-modified acid anhydrides of formula (1) are useful curing agents typically in epoxy resin compositions for encapsulating semiconductor devices. ##STR1## R.sup.1 is a hydrogen atom, substituted or unsubstituted monovalent hydrocarbon group, hydroxyl group, alkoxy group or alkenyloxy group. Rf is a divalent perfluoroalkylene or perfluoropolyether group of the general formula (2): ##STR2## wherein l is an integer of 0 to 8, k and m are integers of 0 to 15, j and n are 0 or 1, with the proviso that j, k, l, m and n are not equal to 0 at the same time.Type: GrantFiled: March 23, 1994Date of Patent: November 8, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshio Shiobara, Koji Futatsumori, Kazuhiro Arai, Hisashi Shimizu, Shigeki Ino
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Patent number: 5359106Abstract: Terminally reactive polysilanes of formula (1) are novel. ##STR1## R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently C.sub.1-12 alkyl or aryl groups, R.sup.5 is an organic group containing an alkoxysilyl, epoxy, glycidyloxy, acryl, methacryl, acetoxysilyl or amino group, A is a C.sub.2-6 alkylene group, n, m and k are numbers in the range: 0.ltoreq.n.ltoreq.10, 0.ltoreq.m.ltoreq.10, n+m.gtoreq.10, and k.gtoreq.1. The polysilanes are prepared by effecting addition reaction between a hydro-terminated polysilane and an unsaturated group-containing reactive compound in the presence of a hydrosilylation catalyst.Type: GrantFiled: December 22, 1993Date of Patent: October 25, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Eiichi Tabei, Shigeru Mori
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Patent number: 5359065Abstract: An improved method of preparing an ortho-, meta- or para-silyl aromatic or heteroaromatic compound represented by the formula ##STR1## wherein X is oxygen or sulfur,R.sub.1 represents the atoms necessary to complete an unsubstituted or substituted aromatic or heteroaromatic ring, andR.sub.2, R.sub.3 and R.sub.Type: GrantFiled: December 7, 1992Date of Patent: October 25, 1994Assignee: Eastman Kodak CompanyInventor: Sundaram Krishnamurthy
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Patent number: 5350811Abstract: An adhesive composition comprising (a) an epoxy resin obtained by reacting a 1,3-bis(dicarboxyphenyl)-1,1,3,3-tetrasubstituted disiloxane dianhydride with an alcohol or alcohol derivative, followed by reaction with an epoxy compound having two or more epoxy groups, or an epoxy resin obtained by reacting a 1,3-bis(dicarboxyphenyl)-1,1,3,3-tetrasubstituted disiloxane with an epoxy compound having two or more epoxy groups and (b) a curing agent is suitable for bonding semiconductor chips to a copper frame with a small warpage of the chips.Type: GrantFiled: June 17, 1993Date of Patent: September 27, 1994Assignee: Hitachi Chemical Co. Ltd.Inventors: Nobuo Ichimura, Mitsuo Yamazaki, Kohei Fujita, Hidetaka Satou, Yasuo Miyamoto, Masao Kawasumi, Tohru Kikuchi
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Patent number: 5347027Abstract: The present invention provides an electroless process for making a catalyst in a liquid or gaseous medium comprising contacting a base metal with a chemical cleaning agent and simultaneously or sequentially treating said base metal under reducing conditions with a noble metal-containing material, the catalyst prepared using the process, and a method of using the catalyst.Type: GrantFiled: April 22, 1993Date of Patent: September 13, 1994Assignee: OSi Specialties, Inc.Inventors: James S. Ritscher, Wei T. Yang, George M. Omietanski, Robert L. Ocheltree, Earl E. Malson
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Patent number: 5336786Abstract: Novel organic silicon compounds are based on a benzene ring having two epoxy radicals and an alkoxysilane radical. They are useful as resin modifiers, adhesive aids for epoxy resins, and silane coupling agents. Inorganic fillers such as silica surface treated with the compounds are useful in encapsulating resin compositions.Type: GrantFiled: December 3, 1993Date of Patent: August 9, 1994Assignee: Shin-Etsu Chemical Company, LimitedInventors: Toshio Shiobara, Koji Futatsumori, Satoshi Okuse, Takayuki Aoki, Miyuki Wakao, Shigeki Ino
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Patent number: 5332852Abstract: This invention resides in a process for production of predominantly a 1,4-O-metallation product of a hydride of silicon, germanium, or tin with an .alpha.,.beta.-unsaturated carbonyl compound. The reaction involved takes place in the presence of a heterogeneous noncomplexed rhodium-containing catalyst. This invention also resides in 1,4-O-metallation compositions having perfluoroalkyl R groups on either side of the C.dbd.C bond of an enol ether or on the acetal side of the C.dbd.C bond of a ketene acetal.Type: GrantFiled: June 3, 1991Date of Patent: July 26, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Salvatore A. Bruno
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Patent number: 5332797Abstract: A composite structure comprising a substrate bearing a layer of release coating prepared from one or more epoxypolysiloxanes together providing cycloaliphatic epoxy group(s) and non-cycloaliphatic (i.e., linear or branched aliphatic) epoxy group(s). The resulting release coating cures quickly and exhibits low release levels to adhesives. An oligomeric epoxypolysiloxane comprising both cycloaliphatic and non-cycloaliphatic epoxy groups is also disclosed.Type: GrantFiled: April 1, 1992Date of Patent: July 26, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Carl R. Kessel, Maureen C. Nelson
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Patent number: 5331076Abstract: Novel siloxane compounds having a fluorinated group, an SiH group reactive with silicone resins, and an epoxy-bearing organic group attached to a silicon atom, each in a backbone, are effective for providing adhesion and are useful tackifiers for various resins.Type: GrantFiled: December 23, 1992Date of Patent: July 19, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Kenichi Fukuda, Yasuo Tarumi, Hiroshi Inomata, Yasushi Yamamoto
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Patent number: 5310843Abstract: An MQ organopolysiloxane compatible with organic plastics, has an epoxy-containing organic group, and has the following general formula ##STR1## R.sup.1 represents monovalent hydrocarbon groups, R.sup.2 represents the hydrogen atom and monovalent hydrocarbon groups, R.sup.3 represents epoxy-containing organic groups and alkoxysilylalkyl groups, a is 0 or a positive number, b and c are positive numbers, a/c has a value of 0 to 4, b/c has a value of 0.05 to 4, and (a+b)/c has a value of 0.2 to 4. Also, a method for the preparation of this organopolysiloxane comprises an addition reaction of an Si-H containing organopolysiloxane with an epoxy-containing compound in the presence of a hydrosilylation catalyst.Type: GrantFiled: September 29, 1992Date of Patent: May 10, 1994Assignee: Dow Corning Toray Silicone Co., Ltd.Inventor: Yoshitsugu Morita
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Patent number: 5269951Abstract: Organosilicon compounds are disclosed which are multi-functional and possess utility as chain branching agents for aminofunctional polysiloxanes used in the softening of textiles and fabrics. The organosilicon compounds possess epoxy functionality and may have further alkyl functionality and/or polyalkylene oxide functionality.Type: GrantFiled: July 17, 1992Date of Patent: December 14, 1993Assignee: Dow Corning CorporationInventors: James McVie, Martin Rowlands
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Patent number: 5268489Abstract: Unsaturated cycloaliphatic esters like higher hydrocarbyl, functionally substituted or polyunsaturated cyclohex-3-ene carboxylates, made directly by cycloaddition of dienes with dienophillic (meth/eth)acrylates, and their derivatives like epoxides and urethanes, provide useful thermal and radiation curable coatings, inks, sealants, adhesives, solvents, acid scavengers, and intermediates for other uses.Type: GrantFiled: February 5, 1993Date of Patent: December 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
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Patent number: 5262506Abstract: There is described an organopolysiloxane which contains at least 2 amino groups, carboxyl groups, hydroxyl groups, or epoxy-functional organic groups at one and only one molecular chain terminal, as well as a method for the preparation of same. The organopolysiloxane has the formula ##STR1## wherein R is a monovalent hydrocarbon group which is free of aliphatically unsaturated bonds and wherein the groups R may be identical or different; A' is selected from the group consisting of groups, the carboxyl group, the hydroxyl group, and epoxy-functional organic groups; B is the same or a different divalent organic group having at least 2 carbon atoms; m is zero or one; and n is an integer with a value of zero to 200.Type: GrantFiled: April 20, 1992Date of Patent: November 16, 1993Assignee: Dow Corning Toray Silicone Co., Ltd.Inventors: Tadashi Okawa, Shuji Yamada