The Sulfur Is Part Of A -sh Or -sc(=x)- Group, Wherein X Is Chalcogen (h Of -sh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 556/429)
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Patent number: 7652162Abstract: A composition is provided that may include a sulfur-functional linear polyorganosiloxane. The sulfur-functional linear polyorganosiloxane may include a chemically protected sulfur group. Under certain conditions, the sulfur group may react with an unsaturated elastomer. The invention may include embodiments that relate to method of making and using the sulfur-functional linear polyorganosiloxane.Type: GrantFiled: December 16, 2005Date of Patent: January 26, 2010Assignee: Momentive Performance Materials Inc.Inventors: Norberto Silvi, Robert James Perry, Ben Purushotam Patel, Paul Burchell Glaser, Brennan Alexander Smith
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Publication number: 20090292054Abstract: The present invention relates to an activated silane compound obtained by reacting a hydrocarbyloxysilane compound with an organic metal compound in an organic solvent, and enhancing interaction of silica with carbon black and improving the fracture characteristic, the abrasion resistance and the low heating property provide an activated silane compound which can be reduced in a blending amount, a rubber composition prepared by blending it as a silane coupling agent and a pneumatic tire prepared by using the above rubber composition, which is excellent in a durability, a low heating property and the like.Type: ApplicationFiled: April 4, 2007Publication date: November 26, 2009Applicant: BRIDGESTONE CORPORATIONInventors: Tetsuya Omura, Kouichi Morita, Uchu Mukai
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Patent number: 7560583Abstract: A mercaptofunctional silane is provided of general Formula (1): [HSG1SiZ?Z?]m[HSG2SiZ?3]n[HSG3SiZ?2X]o[[HSG4SiZ?X2]p??(1) wherein the substituents are defined herein.Type: GrantFiled: October 6, 2006Date of Patent: July 14, 2009Assignee: Momentive Performance Materials Inc.Inventors: Antonio Chaves, Eric Raymond Pohl, Richard W. Cruse
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Patent number: 7550540Abstract: The disclosure herein relates to organofunctional silanes and mixtures of organofunctional silanes possessing mercaptan and hydrocarbyl and/or heterocarbyl functionality. These silanes reduce or eliminate the generation of volatile organic compounds (VOC's) during use, aid in the processing of filled elastomeric materials and enhance the end-use properties of the filled elastomer. The present disclosure relates to a rubber composition and article comprising these silanes.Type: GrantFiled: August 14, 2006Date of Patent: June 23, 2009Assignee: Momentive Performance Materials Inc.Inventors: Antonio Chaves, Eric R. Pohl, Christopher M. Hartshorn
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Publication number: 20090143538Abstract: A silane-coupling-agent-treated silica having a sulfur-deviation range of 50 to 200%, comprising 100 parts by mass of silica surface-treated with 1 to 50 parts by mass of a silane coupling agent represented by the following general formula (1): Y3-Si-Z-S—CO—R (wherein Y is an acetoxy group or an alkoxy group with 1 to 6 carbon atoms, Z is an alkylene group with 1 to 8 carbon atoms, and R is a hydrocarbon group with 1 to 18 carbon atoms) is disclosed. Furthermore, a vibration-damping and vibration-isolating rubber composition comprising 100 parts by mass of a raw rubber material having C—C bonds in the main chain and 1 to 200 parts of the aforementioned silane-coupling-agent-treated silica is claimed.Type: ApplicationFiled: August 9, 2005Publication date: June 4, 2009Applicant: DOW CORNING TORAY CO., LTD.Inventors: Yasuo Nomura, Susumu Takahashi
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Publication number: 20090137730Abstract: A rubber composition, superior in the processability and rubber properties compared with a rubber composition using a conventional mercaptosilane coupling agent, containing 100 parts by weight of a diene-based rubber, 10 to 160 parts by weight of a reinforcing filler containing silica and 0.1 to 20% by weight, based upon the weight of silica, of a mercaptosilane coupling agent blocked with a compound having a vinyl ether group and a pneumatic tire using the same.Type: ApplicationFiled: May 10, 2007Publication date: May 28, 2009Applicant: The Yokohama Rubber Co., LtdInventors: Yoshihiro Kameda, Misaki Matsumura
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Patent number: 7531680Abstract: A composition of matter is disclosed that comprises at least one silane coupling agent for coupling an elastomer and a filler wherein said silane comprises at least one hydrolysable group that, upon compounding said silane with said elastomer and filler, is released to yield a compound that improves downstream processability of the compounded composition or the properties of the final rubber product or both.Type: GrantFiled: May 31, 2006Date of Patent: May 12, 2009Assignee: Momentive Performance Materials Inc.Inventors: Richard W. Cruse, Robert J. Pickwell
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Patent number: 7528273Abstract: An aqueous process is described in which thiocarboxylate silane is produced from haloalkyl silane by reaction of the haloalkyl silane with an aqueous solution of thiocarboxylate salt in the presence of a catalytically effective amount of alkylguanidinium salt.Type: GrantFiled: April 14, 2005Date of Patent: May 5, 2009Assignee: Momentive Performance Materials Inc.Inventors: Tiberiu Ladislau Simandan, Thomas Link Guggenheim
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Patent number: 7504456Abstract: A rubber composition containing a rubber component, a filler and at least one organofunctional silane and/or mixture of organofunctional silanes in which individual silanes possess both free and blocked mercaptan functionality or particular mixtures of the organofunctional silanes possess both free and blocked mercaptan functionality. The organofunctional silanes and silane mixtures are useful, inter alia, as coupling agents for elastomeric compositions, e.g., rubber formulations employed in the manufacture of tires, where they exhibit a desirable balance of low scorch and good performance properties.Type: GrantFiled: February 21, 2006Date of Patent: March 17, 2009Assignee: Momentive Performance Materials Inc.Inventors: Antonio Chaves, Eric R. Pohl, Linda Vecere, Lesley Hwang, Robert Pickwell
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Patent number: 7449539Abstract: The present inventors have obtained a PSQ derivative of a completely condensed type into which a functional group is readily introduced by using a novel PSQ derivative of an incompletely condensed type in which four alkaline metal atoms are bonded to silsesquioxane of a cage type having eight Si's. The above silsesquioxane derivative is represented by Formula (1). A silsesquioxane derivative to which alkaline metal atoms are bonded is represented by Formula (2). In Formula (1) and Formula (2), R is a group selected from alkyl, aryl and arylalkyl; Y is a group represented by Formula (a) or Formula (b); and M is a monovalent alkaline metal atom. X in Formula (a) and Formula (b) is hydrogen, halogen, a hydroxyl group or a monovalent organic group, and Z is —O—, —CH2— or a single bond. The preferred organic group is a functional group or a group having a functional group.Type: GrantFiled: October 11, 2006Date of Patent: November 11, 2008Assignee: Chisso CorporationInventors: Yoshitaka Morimoto, Kenichi Watanabe, Nobumasa Ootake, Jyun-ichi Inagaki, Kazuhiro Yoshida, Koji Ohguma
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Publication number: 20080161590Abstract: The invention relates to sulfur silane coupling agents containing multiple blocked mercapto groups which are in a state of reduced activity until activated. The coupling agents are advantageously used in rubber formulations, for example, for fabricating tires with low rolling resistance.Type: ApplicationFiled: December 28, 2006Publication date: July 3, 2008Inventors: Richard W. Cruse, W. Michael York, Eric R. Pohl, Antonio Chaves, Tiberiu L. Simandan, Prashant Joshi
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Patent number: 7323582Abstract: Organosilicon compounds of the general formula I and/or II are produced by reacting silanes of the general formula III with alcohols of the general formula R?—OH, with elimination of R—OH, wherein R—OH may be continuously separated from the reaction mixture by distillation. The organosilicon compounds may be used in rubber mixtures. Compounds, such as rubbers, produced using such organosilicon compounds.Type: GrantFiled: July 30, 2004Date of Patent: January 29, 2008Assignee: Degussa AGInventors: Ulrich Deschler, Roland Krafczyk, Hans-Detlef Luginsland, Karsten Korth, Ingo Kiefer, Michael Horn
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Patent number: 7301042Abstract: Rubber composition intended for the manufacture of tire casings which have improved hysteretic properties and scorch safety, based on at least one elastomer and silica by way of reinforcing filler enclosing a reinforcing additive consisting of the mixture and/or the product of in situ reaction of at least one functionalized polyorganosiloxane compound containing, per molecule, at least one functional siloxy unit capable of bonding chemically and/or physically to the surface hydroxyl sites of the silica particles and at least one functionalized organosilane compound containing, per molecule, at least one functional group capable of bonding chemically and/or physically to the polyorganosiloxane and/or the hydroxyl sites of the silica particles and at least one other functional group capable of bonding chemically and/or physically to the polymer chains.Type: GrantFiled: April 23, 2002Date of Patent: November 27, 2007Inventor: Richard W. Cruse
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Patent number: 7189867Abstract: A compound having the formula CF3—CH(OH)—CH2—(L)n—CH2—SH or a disulfide thereof. Each L is substituted or unsubstituted methylene, substituted or unsubstituted oxyalkylene, and alkyl-substituted or unsubstituted siloxanylene. The compound is free of carboxysilane linkages. The value of n is a positive integer. A metal surface having the group CF3—CH(OH)—CH2—(L)n—CH2—S— bound thereto. A method of making CF3—CH(OH)—CH2—(L)n—CH2—SH by: reacting OHC—CH2—(L)n—CH2—X with (trifluoromethyl)trialkylsilane to form CF3—CH(OH)—CH2—(L)n—CH2—X; reacting the intermediate with a thiocarbonyl compound to form an adduct; and hydrolyzing the adduct followed by protonation. X is a halogen.Type: GrantFiled: September 19, 2006Date of Patent: March 13, 2007Assignee: The United States of America as represented by the Secretary of the NavyInventors: James H Wynne, Arthur W Snow
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Patent number: 7169873Abstract: The present inventors have obtained a PSQ derivative of a completely condensed type into which a functional group is readily introduced by using a novel PSQ derivative of an incompletely condensed type in which four alkaline metal atoms are bonded to silsesquioxane of a cage type having eight Si's. The above silsesquioxane derivative is represented by Formula (1). A silsesquioxane derivative to which alkaline metal atoms are bonded is represented by Formula (2). In Formula (1) and Formula (2), R is a group selected from alkyl, aryl and arylalkyl; Y is a group represented by Formula (a) or Formula (b); and M is a monovalent alkaline metal atom. X in Formula (a) and Formula (b) is hydrogen, halogen, a hydroxyl group or a monovalent organic group, and Z is —O—, —CH2— or a single bond. The preferred organic group is a functional group or a group having a functional group.Type: GrantFiled: September 17, 2002Date of Patent: January 30, 2007Assignee: Chisso CorporationInventors: Yoshitaka Morimoto, Kenichi Watanabe, Nobumasa Ootake, Jyun-ichi Inagaki, Kazuhiro Yoshida, Koji Ohguma
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Patent number: 7151188Abstract: Mercaptoalkylalkoxysilane is obtained by reacting at least one sulfide of the general formula MHS wherein M is an alkali metal or ammonium with a haloalkyl silane in an aqueous reaction medium in the presence of an acidic gas to maintain the pH of the reaction medium at or below about 10, and in the additional presence of alkylguanidinium salt phase transfer catalyst to provide mercaptoalkylalkoxysilane, the alkylguanidinium salt phase transfer catalyst being represented by the general formula: wherein each of R1-5 is a primary alkyl radical and R6 is a primary alkyl or bis(primary alkylene) radical, or at least one of the R1–R2, R3–R4 and R5–R6 combinations with the respective connecting nitrogen atom forms a heterocyclic radical; X is an anion; and n is 1 or 2.Type: GrantFiled: November 16, 2005Date of Patent: December 19, 2006Assignee: General Electric CompanyInventors: Tiberiu L. Simandan, Michael R. Powell
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Patent number: 7019160Abstract: The present invention relates to a process for the preparation of (mercaptoorganyl)-alkoxysilanes by reacting an alkali metal sulfide with a mixture of (haloorganyl)alkoxysilane and (haloorganyl)halosilane in an alcohol with the exclusion of air and under elevated pressure.Type: GrantFiled: November 4, 2004Date of Patent: March 28, 2006Assignee: Degussa AGInventors: Karsten Korth, Philipp Albert, Ingo Kiefer
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Patent number: 6998452Abstract: This invention relates to a process for producing a free radical control agent of the structural formula: wherein Z is selected from the group consisting of wherein R1 is an alkyl group of 1 to 4 carbon atoms, cyclohexyl or phenyl; wherein R2 is an alkoxy group of 1 to 8 carbon atoms or a cycloalkoxy group of 5 to 8 carbon atoms; wherein Alk is a divalent hydrocarbon of 1 to 18 carbon atoms; and wherein Y represents a functional group that is capable of activating a vinylic carbon toward free radical addition; said process comprising the steps of (1) reacting a mercaptosilane of the structural formula: Z-Alk-SH with carbon disulfide in the presence of a phase transfer catalyst and an alkali metal hydroxide to produce a trithiocarbonate salt; and (2) reacting the trithiocarbonate salt with a halogen containing compound of the structural formula X-Y to produce the free radical control agent, wherein X represents a halogen atom.Type: GrantFiled: January 14, 2005Date of Patent: February 14, 2006Assignee: The Goodyear Tire & Rubber CompanyInventor: Dane Kenton Parker
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Patent number: 6995280Abstract: The present invention is directed to a process for preparing (mercaptoorganyl)alkoxysilanes by conversion of alkali-metal hydrogensulfide with a mixture of (haloorganyl)alkoxysilane and (haloorganyl)halosilane in an alcohol with air excluded and at an elevated pressure.Type: GrantFiled: November 4, 2004Date of Patent: February 7, 2006Assignee: Degussa AGInventors: Karsten Korth, Philipp Albert, Ingo Kiefer
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Patent number: 6974500Abstract: To provide a primer composition having an excellent balance between storage stability and adhesiveness, while permitting a longer open time. The primer composition includes: a compound (a) represented by the following formula (1): and an organic solvent (b).Type: GrantFiled: August 18, 2003Date of Patent: December 13, 2005Assignee: The Yokohama Rubber Co., Ltd.Inventors: Akihiro Miyata, Kazunori Ishikawa, Hideyuki Matsuda
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Patent number: 6949666Abstract: The method for producing polyorganosiloxane from at least one type of organosilicon compound having a siloxane unit or alkoxysilane by the equilibrating reaction involving cleavage and recombination of the silicon-oxygen bond as a method carried out in the presence of an acidic catalyst capable of giving the product in high productivity and yield, corrosive to the system to a limited extent, and remaining in the product to a limited extent or degrading product quality to a limited extent if it remains, wherein a solid, acidic zirconium oxide catalyst is used as the acidic catalyst.Type: GrantFiled: November 1, 2002Date of Patent: September 27, 2005Assignee: Nippon Unicar Company LimitedInventors: Yasunori Chayama, Ikutaro Morikawa, Hiroaki Shoji
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Patent number: 6867319Abstract: A process for the preparation of (D) thiocyanato-bearing organoalkoxysilanes represented by the general formula (3) NCS—R1—Si(OR2)nR33-n wherein R1 is a divalent hydrocarbon group having 1 to 6 carbon atoms, R2 and R3 are monovalent hydrocarbon groups, and the subscript n has a value of from 0 to 3, in which (A) a thiocyanic acid salt represented by the general formula (1) MSCN, wherein M is an alkali metal and (B) a halogenated alkylalkoxysilane represented by the general formula (2) XR1Si(OR2)nR33-n wherein X is a halogen atom, and R1, R2, R3, and the subscript n are the same as above, are reacted in the presence of (C) a phase transfer catalyst.Type: GrantFiled: September 20, 2002Date of Patent: March 15, 2005Assignee: Dow Corning Toray Silicone Company, Ltd.Inventor: Keiji Wakita
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Patent number: 6861546Abstract: A mixture containing a monohydric alkyl alcohol and an alkoxysilane is purified by (i) adding an organic salt or an inorganic salt to the monohydric alkyl alcohol and the alkoxysilane; (ii) mixing the organic or inorganic salt with the monohydric alkyl alcohol and the alkoxysilane; and (iii) separating from (ii) a first phase containing the alkoxysilane, and a second phase containing the monohydric alcohol and the organic or inorganic salt. The preferred salt is lithium chloride, and the monohydric alkyl alcohol is most typically methyl alcohol or ethyl alcohol.Type: GrantFiled: February 3, 2004Date of Patent: March 1, 2005Assignee: Dow Corning CorporationInventor: Stephen Paul Ferguson
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Patent number: 6844460Abstract: Mercaptoalkylalkyldialkoxysilane compositions are prepared by reacting an alkoxysilane containing an unsaturated organic group, with a sulfur containing organic acid, in the presence of a peroxide catalyst. This step produces a thiol ester. In the next step, methanolysis of the thiol ester is carried out in the presence of a basic catalyst. The resulting product is a mercaptoalkylalkyldialkoxysilane composition such as mercaptoethylmethyldimethoxysilane, mercaptomethylmethyldiethoxysilane, mercaptopropylmethyldiethoxysilane, or mercaptopropylmethyldimethoxysilane. Carrying out the first step of the reaction at least in part in the presence of air obtains maximum efficiency.Type: GrantFiled: January 3, 2003Date of Patent: January 18, 2005Assignee: Dow Corning CorporationInventor: Binh Thanh Nguyen
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Patent number: 6777569Abstract: A process for the manufacture of a blocked mercaptosilane comprising: reacting at least one polysulfane-containing organosilicon compound of the general formula: (R13SiG)2Sn (a) in which each R1 is independently methoxy, ethoxy or alkyl of from 1 to about 6 carbon atoms, provided, that at least one R1 group is methoxy or ethoxy, G is an alkylene group of from 1 to about 12 carbon atoms and n is from 2 to about 8, with at least one alkali metal, alkaline earth metal or a basic derivative of an alkali metal or alkaline earth metal to provide the corresponding metal salt of the polysulfane-containing organosilicon compound and; (b) reacting the metal salt of the polysulfane-containing organosilicon compound with an acyl halide or carbonyl dihalide to provide a blocked mercaptosilane.Type: GrantFiled: March 3, 2003Date of Patent: August 17, 2004Assignee: General Electric CompanyInventors: Mark D. Westmeyer, Russell Burton, Tiberiu L. Simandan
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Patent number: 6727339Abstract: Oligomeric organosilanes useful in rubber mixtures are built up from the two structural units A and B, according to formula I The oligomeric organosilanes are produced by mixing and then co-oligomerizing the monomeric compounds of the structure types I and IIType: GrantFiled: July 3, 2002Date of Patent: April 27, 2004Assignee: Degussa AGInventors: Hans-Detlef Luginsland, Andre Hasse, Michael Radcziwill, Roland Krafczyk
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Patent number: 6680398Abstract: In a first embodiment of a process for making mercaptoalkylalkoxysilanes, a pH adjusting agent and a sulfide containing compound are mixed in an aqueous phase to provide a pH of 4-9, a phase transfer catalyst is added to the aqueous phase, a haloalkylalkoxysilane is then added to the aqueous phase to form a reaction mixture containing mercaptoalkylalkoxysilanes and water soluble byproducts, and the desired mercaptoalklyalkoxysilanes are separated from the water soluble byproducts. In an alternate embodiment, the haloalkylalkoxysilane, the phase transfer catalyst, and an anhydrous pH adjusting agent such as sulfur dioxide, carbon dioxide, hydrogen sulfide, phosphoric acid, boric acid, and hydrochloric acid, are mixed, then an aqueous solution of a sulfide containing compound is added to form a reaction mixture containing mercaptoalkylalkoxysilanes and water soluble byproducts, and desired mercaptoalklyalkoxysilanes are separated from water soluble byproducts.Type: GrantFiled: August 16, 2002Date of Patent: January 20, 2004Assignee: Dow Corning CorporationInventors: Lisa Marie Boswell, William Charles Maki, Anil Kumar Tomar
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Patent number: 6617039Abstract: The invention relates to a process for coating a substrate with a nitrogen-free compound corresponding to formula (I) and/or a hydrolysis product or condensation product [R1(R2)j]iSiR3k(OR4)4−k−i (I), wherein i represents the number 1, 2 or 3, j represents an integer from 1 to 10, k represents the number 0, 1 or 2, k+i is ≦3, and R1 represents OH, OR, SH, SR, OOC—R, R represents C1-C10-alkyl or C6-C12-aryl, R2 is an unsubstituted, singly substituted, or doubly substituted methylene group, R3 is a substituted or unsubstituted C1-C10-alkyl or C6-C12-aryl group, R4 represents a C1-C10-alkyl or C6-C12-aryl group, and wherein if j represents from 2 to 10 the methylene groups in the chain may optionally be interrupted once or several times by hetero atoms.Type: GrantFiled: December 12, 2001Date of Patent: September 9, 2003Assignee: Bayer AktiengesellschaftInventors: Michael Mager, Jürgen Kirsch, Steffen Hofacker
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Patent number: 6518335Abstract: A method is provided for preparing sulfur-containing silane coupling agents by reacting an alkoxysilane acetal with a sulfurating agent. The sulfur-containing silane coupling agents so prepared include certain novel mercapto silanes, and are useful in providing rubber tires with improved properties.Type: GrantFiled: January 5, 2000Date of Patent: February 11, 2003Assignee: Crompton CorporationInventors: James D. Reedy, Kenneth W. Hartman
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Patent number: 6284858Abstract: This invention relates to silicone compounds in which terminal SiO of cage-type and/or ladder-type polyphenylsilsesquioxanes is wholly or partly linked to a triorganosilyl group containing reactive functional group X and also relates to a process for preparing said silicone compounds by subjecting cage-terminated and silanol-free cage-type and/or ladder-type polyphenylsilsesquioxanes to an equilibrium reaction under heat with disiloxanes containing reactive functional group X of the following structural formula in an organic solvent in the presence of an alkaline rearrangement and condensation catalyst. This invention provides silicone compounds containing terminal reactive functional groups of excellent storage stability and properties of good reproducibility such as heat resistance.Type: GrantFiled: September 14, 1999Date of Patent: September 4, 2001Assignees: Nippon Steel Chemical Co., Ltd., Nippon Steel CorporationInventors: Takeshi Fujiyama, Nobuyuki Furukawa, Takero Teramoto
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Patent number: 6271331Abstract: The present invention relates to multifunctionalized alkoxy, the alkoxy functionality Y being introduced onto a suitable polyhydroorganosiloxane by a dehydrogenation/condensation reaction from the alcohol from which Y derives and then the functionality W by a hydrosilylation reaction from the olefinic compound form which W derives. The multifunctionalized alkoxy polyorganosiloxanes can be used as antiadhesion modulators in silicone compositions and as silica covering agents in silicone compositions containing fillers.Type: GrantFiled: December 3, 1999Date of Patent: August 7, 2001Inventors: Michel Gay, Philippe Jost, Michel Peignier, Christian Priou
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Patent number: 6268455Abstract: Provided is a novel mercaptomethylphenyl group-containing diorganopolysiloxane compound represented by the following Formula (1): wherein R1 represents methyl or phenyl; R2 represents a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group or A; l represents an integer of 0 to 500; m represents an integer of 0 to 1,000; n represents an integer of 0 to 500; p represents an integer of 0 to 2; and A is a group represented by Formula (2): wherein X represents a linear or branched alkylene group having 2 to 20 carbon atoms; at least one of R3, R4, R5, R6 and R7 represents mercaptomethyl, and the remaining groups each represent a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms.Type: GrantFiled: March 8, 2000Date of Patent: July 31, 2001Assignee: Chisso CorporationInventors: Takashi Matsuo, Youichi Kimae
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Patent number: 6169194Abstract: Oligonucleotides and other biomolecules are immobilized in high density on solid substrates through covalent forces using either a permanent thioether bond, or a chemoselectively reversible disulfide bond to a surface thiol. Substrates which have hydroxyl groups on their surfaces can be first silanized with a trichlorosilane containing 2-20 carbon atoms in its hydrocarbon backbone, terminating in a protected thiol group. The oligonucleotides or other biomolecules are first connected to a tether consisting of a hydrocarbon or polyether chain of 2-20 units in length which terminates in a thiol group. This thiol may be further modified with a halobenzylic-bifunctional water soluble reagent which allows the conjugate to be immobilized onto the surface thiol group by a permanent thioether bond. Alternatively, the oligonucleotide-tether-thiol group can be converted to a pyridyldisulfide functionality which attaches to the surface thiol by a chemoselectively reversible disulfide bond.Type: GrantFiled: October 16, 1997Date of Patent: January 2, 2001Inventors: Michael Thompson, Mark E. McGovern
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Patent number: 6147242Abstract: Silylalkylthiols are produced by reacting silylalkylsulfanylsilanes with water. The silylalkylsulfanylsilanes used as starting products can be produced by reacting bil-silylalkylpolysulfanes or bis-silylalkyldisulfanes with alkali metal and chlorosilanes.Type: GrantFiled: December 28, 1999Date of Patent: November 14, 2000Assignee: Degussa-Huls AGInventor: Christoph Batz-Sohn
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Patent number: 5916973Abstract: The present invention relates to compounds of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are independently selected from alkoxy radicals having from 1 to 8 carbon atoms, x is O or an integer of from 1 to 10; and Y is Li, K or Na. These compounds may be used as silica couplers in rubber compositions.Type: GrantFiled: August 13, 1997Date of Patent: June 29, 1999Assignee: The Goodyear Tire & Rubber CompanyInventors: Rene Jean Zimmer, Friedrich Visel, Uwe Ernst Frank, Thierry Florent Edme Materne
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Patent number: 5840952Abstract: After reacting sodium sulfide anhydride and hydrogen sulfide, 3-halopropylalkoxy silane represented by the general formulaX (CH.sub.2).sub.3 Si (OR).sub.a R.sub.3-a (I)is added reacted, wherein X denotes Cl or Br; R denotes a methyl, ethyl or propyl group wherein R's can be all identical or different from each other; and "a" denotes an integer 1, 2 or 3.Type: GrantFiled: October 31, 1996Date of Patent: November 24, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Muneo Kudo, Hideyoshi Yanagisawa, Shoji Ichinohe, Akira Yamamoto, Satoru Beppu, Hiroyuki Iwaki, Satoshi Sekizawa
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Patent number: 5831106Abstract: A process for preparing metallocene complexes of the general ##STR1## in which the substituents have the following meanings:M is titanium, zirconium, hafnium, vanadium, niobium or tantalum,X is fluorine, chlorine, bromine, iodine, hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl or --OR.sup.5,where R.sup.5 is C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl, alkylaryl, aryl-alkyl, fluoroalkyl or fluoroaryl with, in each case, 1 to 10 carbon atoms in the alkyl radical and 6 to 20 carbon atoms in the aryl radical,R.sup.1 to R.sup.4 and R.sup.6 to R.sup.9 are hydrogen, C.sub.1 -C.sub.10 -alkyl, 5- to 7-membered cycloalkyl which can in turn carry C.sub.1 -C.sub.10 -alkyls as substituents, or C.sub.6 -C.sub.15 -aryl or aryl-alkyl, it also being possible where appropriate for two adjacent radicals together to be cyclic groups having 4 to 15 carbon atoms, or Si(R.sup.10).sub.3 withR.sup.10 being C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl or C.sub.3 -C.sub.Type: GrantFiled: May 16, 1996Date of Patent: November 3, 1998Assignee: BASF AktiengesellschaftInventors: Franz Langhauser, David Fischer, Gunther Schweier, Hans-Herbert Brintzinger, Hans-Robert-Hellmuth Damrau
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Patent number: 5792881Abstract: The invention relates to hydrolyzable and polyadditive silanes, a method of heir production and of their use in the production of (hetero) silicic acid polycondensates and of polyadducts. The silanes in accordance with the invention have the general formula?(HS--R.sup.5).sub.n R.sup.6 --S--E--R.sup.5 !.sub.a SiX.sub.x R.sup.3.sub.4-a-x (I)in which the groups and indices are equal or different and have the following meaning:E=--CO--NH--, CS--NH--, --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH(OH)--;R.sup.3 =alkyl, alkenyl, aryl, alkylaryl or arylalkyl each with 1 to 15 carbon atoms, whereby these groups may be interrupted by oxygen or sulfur atoms, by ester, carbonyl, amide or amino groups;R.sup.5 =Alkene, arylene, arylenealkene or arylenealkene each with 1 to 15 carbon atoms, whereby these groups may be interrupted by oxygen or sulfur atoms, by ester, carbonyl, amide or amino groups;R.sup.Type: GrantFiled: March 5, 1997Date of Patent: August 11, 1998Assignee: Fraunhofer-Gesellschaft zur Forderung der angewandten Forschung e.V.Inventors: Herbert Wolter, Werner Storch
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Patent number: 5780661Abstract: Allyl silane compounds represented by the formula (CH.sub.2 .dbd.CH--CH.sub.2 --)R.sub.n SiCl.sub.3-n (R represents, independently of each other, hydrocarbon groups with a carbon number of C.sub.1 to C.sub.8 ; n represents an integer from 0 to 3) are reacted with AX (AX stands for mercaptans, thiocarboxylic acids, carbon tetrachloride, or chloroform, the letter X represents, respectively, H bonded to sulfur in the case of mercaptans and thiocarboxylic acids, chlorine in the case of carbon tetrachloride, and H in the case of chloroform, and the letter A represents a residual group bonded to X) in the presence of radical generating agents, thereby obtaining allylsilane compounds represented by the formula (ACH.sub.2 CHXCH.sub.2)R.sub.n SiCl.sub.3-n (R, n, A and X have the same meaning as above).Type: GrantFiled: June 5, 1997Date of Patent: July 14, 1998Assignee: Dow Corning Asia, Ltd.Inventors: Mitsuhiro Iwata, Hideki Sakurai, Takanobu Sanji
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Patent number: 5677291Abstract: A method of lowering plasma cholesterol level in a patient with hypercholesterolemia, by administration of a compound of formula (1) ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently a C.sub.1 -C.sub.6 alkyl group;Z is a thio, oxy or methylene group;A is a C.sub.1 -C.sub.4 alkylene group; andR.sub.5 is a C.sub.1 -C.sub.6 alkyl or --(CH.sub.2).sub.n --(Ar)wherein n is an integer 0, 1, 2 or 3; and Ar is phenyl or napthyl unsubstituted or substituted with one to three substituents selected from the group consisting of hydroxy, methoxy, ethoxy, chloro, fluoro or C.sub.1 -C.sub.6 alkyl.Type: GrantFiled: January 2, 1996Date of Patent: October 14, 1997Assignee: Hoechst Marion Roussel, Inc.Inventors: Simon J. T. Mao, Mark T. Yates, Roger A. Parker
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Patent number: 5631338Abstract: The present invention provides a process for preparing bisphenol A with a high conversion and selectivity by reacting phenol with acetone in the presence of both a polyorganosiloxane having a mercapto group-containing hydrocarbon group and an acid. It is preferable that the polyorganosiloxane having a mercapto group-containing hydrocarbon group and the acid is a polyorganosiloxane having both a mercapto group-containing hydrocarbon group and a sulfonic acid group.Type: GrantFiled: July 11, 1995Date of Patent: May 20, 1997Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Kaoru Inoue, Tuneyuki Ohkubo, Takashi Terajima
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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: 5486633Abstract: The present invention relates, in general, to photochemically removable protecting groups, and, in particular, to the use of styrylsilyl groups to protect reactive functional groups, such as, hydroxyl, amino and thiol groups.Type: GrantFiled: November 10, 1994Date of Patent: January 23, 1996Assignee: Duke UniversityInventors: Michael C. Pirrung, Yong Rok Lee
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Patent number: 5436358Abstract: The present invention relates to novel cyclic or linear 2-(aryl)propylalkylpolysiloxane type silicone fluids as represented by the formula I and their preparation methods by hydrolyzing mixtures of 2-(aryl)propylalkyldichlorosilane and diorganodichlorosilane as represented by the formula II and formula III respectively. ##STR1## wherein, X.sub.1 and X.sub.2 represent independently hydrogen or alkyl(C.sub.1 -C.sub.3), phenyl, phenoxy, fluoro, chloro, bromo, mercapto, mercaptomethyl group; R.sup.2 and R.sup.3 represent independently methyl or phenyl group; R.sup.1 in the formula I is same as CH.sub.2 CH.sub.2 R in formula II or cyclohexyl wherein R is C.sub.n H.sub.2n+2 (n=1-16), chloromethylene, cyanomethylene, phenyl, or cyano group; M represents H or SiMe.sub.3 group wherein Me is methyl group and when M is hydrogen, the silanol groups at the both ends of the molecule easily undergo dehydration and cyclize to form the cyclic silicone fluids; n and m can be 2-200 and the ratio n/m can be 1:0.01-1:100.Type: GrantFiled: September 8, 1994Date of Patent: July 25, 1995Assignee: Korea Institute of Science and TechnologyInventors: Il N. Jung, Bok R. Yoo, Bong W. Lee
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Patent number: 5428176Abstract: Processes for preparing 2,2-difluoroketene silyl O,S-acetals and .alpha.,.alpha.-difluoro-.beta.-silyloxy-1,3-dioxolane-4-propanoic acid O,S-esters.Type: GrantFiled: April 14, 1994Date of Patent: June 27, 1995Assignee: Eli Lilly and CompanyInventor: John A. Weigel
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Patent number: 5385999Abstract: This invention relates to polysiloxanes having fluoroaliphatic- and carboxyl- containing terminal groups, their preparation and their use in imparting water-, oil- and soil-repellency and a soft hand to fibrous substrates such as leather, and to the resulting treated substrate.Type: GrantFiled: November 3, 1993Date of Patent: January 31, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Claude D'Anvers, Dirk M. Coppens
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Patent number: 5354879Abstract: The present invention relates to a synthetic method of optically active starting materials for various medicaments, which are represented by Formula (I): ##STR1## wherein R.sup.1 is hydrogen or hydroxy protecting group; * is an asymmetric carbon; R.sup.2 ' is hydrogen or an optionally substituted lower alkyl; and Q is --CH.dbd.P(Ph).sub.3, --CH.sub.2 P(O)(OMe).sub.2, or --CH.sub.2 S(O)Me, in high optical purity on a large scale.In more detail, the present invention provides intermediates and a method for the production thereof for synthesizing optically active compounds which are able to inhibit activities of HMG-CoA reductase and are, therefore, useful for inhibition of cholesterol biosynthesis.Type: GrantFiled: February 19, 1993Date of Patent: October 11, 1994Assignee: Shionogi Seiyaku Kabushiki KaishaInventors: Toshiro Konoike, Yoshitaka Araki
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Patent number: 5342983Abstract: Organic silicon compounds which are expressed by the general chemical formulae (I) or (II): ##STR1## wherein R.sup.1 is a monovalent organic group with 1 to 8 carbon atoms; R.sup.2, R.sup.3 and R.sup.4 in each equation are independent and either a monovalent organic group with 1 to 8 carbon atoms or a siloxyl group expressed by ##STR2## wherein R.sup.5, R.sup.6 and R.sup.7 are independent in each equation and they are a monovalent organic group with 1 to 8 carbon atoms; and a is either 0, 1 or 2. The novel organic silicon compounds possess both a polymerizable double bond and organopolysiloxane within the same molecule. These compounds are superior in their polymerizability and copolymerizability and are useful as polymer reforming agents.Type: GrantFiled: March 5, 1993Date of Patent: August 30, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshio Yamazaki, Hideki Sugahara, Shoji Ichinohe, Toshinobu Ishihara, Tohru Kubota
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Patent number: 5237083Abstract: An aqueous glass fiber sizing composition acetate file former and an effective amount of a lubricant additive having the formula: ##STR1## where R is an alkyl or alkenyl group of 6 to 20 carbons, A is a divalent organic--S--or--NH--group, R.sup.1 is an alkyl group of 1 to 4 carbons, m is or 1 and n is 0 to 10 with the proviso that when n is O, m is also O.Type: GrantFiled: March 5, 1992Date of Patent: August 17, 1993Assignee: National Starch and Chemical Investment Holding CorporationInventors: Gary T. Martino, Michael J. Hasuly, John J. Tsai