Sulfur Or Halogen In Alcohol Moiety Patents (Class 560/87)
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Patent number: 8765235Abstract: Provided is a novel polymerizable azomethine compound which has a high ?n and is colorless. The compound is represented by the formula (I). P1 and P2 each are a polymerizable group; m1 and m2 each are an integer of from 1 to 10; R1 and R2 each are an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an alkoxycarbonyl group having from 2 to 5 carbon atoms, an acyloxy group having from 2 to 5 carbon atoms, an acyl group having from 2 to 4 carbon atoms, an amide group having from 2 to 5 carbon atoms, a cyano group or a halogen atom; n1 and n2 each are an integer of from 0 to 4; R3 is a hydrogen atom, or an alkyl group having from 1 to 4 carbon atoms; Z1 and L1 each are a predetermined divalent group; n is 0, 1 or 2.Type: GrantFiled: December 17, 2012Date of Patent: July 1, 2014Assignee: FUJIFILM CorporationInventors: Masatoshi Mizumura, Shunya Katoh, Yasuhiro Ishiwata, Masaomi Kimura
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Patent number: 8742159Abstract: To provide a fluorinated compound having an RF group with at most 6 carbon atoms, whereby a fluorinated polymer having a highly durable water/oil repellency can be produced, and an environmental load is little, and a fluorinated polymer having a highly durable water/oil repellency and presenting little environmental load, obtainable by polymerizing such a fluorinated compound. A fluorinated compound represented by the following formula (I) and its polymer: CH2?C(M)COOXPhCOO(CH2)mCrF2r+1??(I) (in the formula (I), M is a hydrogen atom, a methyl group or a halogen atom, X is CHR1CH2O or CH2CHR1O, R1 is a C1-4 linear or branched alkyl group or CH2OR2, R2 is a C1-4 linear or branched alkyl group, Ph is a phenylene group, m is an integer of from 1 to 4, and r is an integer of from 1 to 6).Type: GrantFiled: September 14, 2012Date of Patent: June 3, 2014Assignee: Asahi Glass Company, LimitedInventor: Taiki Hoshino
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Patent number: 8471056Abstract: To provide a fluorinated compound having an RF group with at most 6 carbon atoms, whereby a fluorinated polymer having a highly durable water/oil repellency can be produced, and an environmental load is little, and a fluorinated polymer and a fluorinated copolymer having a highly durable water/oil repellency and presenting little environmental load, obtainable by polymerizing such a fluorinated compound. A fluorinated compound represented by the following formula (I) and its polymer: CH2?C(M)COO(CH2)nPhCOO(CH2)mCrF2r+1??(I) (in the formula (I), M is a hydrogen atom, a methyl group or a halogen atom, n is an integer of from 0 to 2, Ph is a phenylene group, m is an integer of from 1 to 4, and r is an integer of from 1 to 6).Type: GrantFiled: March 28, 2012Date of Patent: June 25, 2013Assignee: Asahi Glass Company, LimitedInventor: Taiki Hoshino
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Publication number: 20110269722Abstract: The invention provides the compounds of formula (I) or pharmaceutically acceptable salts thereof. The invention also provides pharmaceutical compositions comprising one or more compounds of formula I or intermediates thereof and one more of pharmaceutically acceptable carriers, vehicles or diluents. The invention further provides methods of preparation and methods of use of prodrugs including NO-releasing prodrugs, double prodrugs and mutual prodrugs comprising the compounds of formula I.Type: ApplicationFiled: December 23, 2010Publication date: November 3, 2011Inventor: Apparao Satyam
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Patent number: 7910179Abstract: Disclosed are a vinylsulfone derivative, a liquid crystal composition comprising the same, and a compensation film for a liquid crystal display device using the same liquid crystal composition. More particularly, the vinylsulfone derivative is a liquid crystal material of a high-quality view angle compensation film, which improves a contrast ratio measured at a tilt angle when compared to a contrast ratio measured from the front surface and minimizes color variations in a black state depending on view angles.Type: GrantFiled: November 21, 2006Date of Patent: March 22, 2011Assignee: LG Chem, Ltd.Inventors: Jae Ho Cheong, Min Jin Ko, Dae Ho Kang, Ki Youl Lee
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Publication number: 20100316952Abstract: A salt represented by the formula (a1): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C4 perfluoroalkyl group, X1 represents —CO—O—Xa1— or —CH2—O—Xa2— wherein Xa1 and Xa2 independently each represent a C1-C15 alkylene group and one or more —CH2— in the alkylene group can be replaced by —O— or —CO—, Y1 represents a C3-C36 alicyclic hydrocarbon group or a C6-C24 aromatic hydrocarbon group, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O— or —CO—, and Z+ represents an organic cation.Type: ApplicationFiled: June 9, 2010Publication date: December 16, 2010Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Koji Ichikawa, Masako Sugihara, Hiromu Sakamoto
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Publication number: 20090231664Abstract: An electrochromic compound represented by the following General Formula (1). A-(CX2)n—B ??General Formula (1) In the formula, A is a monovalent binding group, B is a redox chromophore, X is a halogen atom, and n is an integer of 1 or more.Type: ApplicationFiled: March 10, 2009Publication date: September 17, 2009Inventors: Takeshi SHIBUYA, Shigenobu Hirano, Hiroshi Kondo, Yuki Nakamura, Yukiko Abe, Tohru Yashiro
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Patent number: 7507853Abstract: The present invention relates to an improved process for the preparation of phenolic carboxylic acid derivatives catalysed by biocatalytic esterification, transesterification or amidation of a corresponding lower alkyl ester. Biocatalysis is performed in the presence of suitable enzymes, e.g. hydrolases, especially esterases, amidases, lipases and proteases.Type: GrantFiled: October 2, 2003Date of Patent: March 24, 2009Assignee: Ciba Specialty Chemicals CorporationInventors: Reinhold Öhrlein, Gabriele Baisch, Kai-Uwe Schöning, Jemima Schmidt, Sandra Franziska Mayer
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Patent number: 7393569Abstract: A polymerizable liquid crystal composition containing compounds represented by the formula (1-1) and the formula (1-2), compounds represented by the formula (2-1) and the formula (2-2), and a compound represented by the formula (3-1): the polymerizable liquid crystal composition having homogeneous, homeotropic, or hybrid alignment, which can be coated on a support substrate, for example, of a transparent plastic film such as a triacetyl cellulose film or cycloolefin polymer film, or glass, and is aligned on a substrate as a polymer film while maintaining the alignment.Type: GrantFiled: June 9, 2006Date of Patent: July 1, 2008Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventors: Maiko Ito, Masami Kimura, Ryushi Shundo
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Patent number: 6734320Abstract: Novel non-symmetric, partially fluorinated compositions and method of manufacture which are useful as lubricants or as additives to lubricant formulations involving the molecular structure: R1f—F′—R2—F″—R3h where R1f represents a wholly or partially fluorinated organic residue end group, F′ and F″ represent functional linkages which may be alike or different, R2 represents the backbone and R3h represents a non-fluorinated organic residue end group. Such compositions are produced by reacting a mixture of alcohols, mercaptans or amines containing at least one partially fluorinated compound and at least one non-fluorinated compound in the mixture, thus producing the R1f and the R3h residues, with a difunctional organic compound (e.g., diacid, dinitrile, disulfonyl halide, diisocyanate, diisothiocyanate, diphosphoryl halide or dithiophosphoryl halide).Type: GrantFiled: April 30, 2002Date of Patent: May 11, 2004Assignee: E. I. du Pont de Nemours and CompanyInventor: Richard P. Beatty
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Patent number: 6207853Abstract: A process for the preparation of an enantiomerically enriched 2-substituted succinic acid derivative of formula 2, which comprises asymmetric hydrogenation of the dehydro precursor of formula 7 or 8, or a mixture thereof wherein R1 and R2 are independently H, a salt-forming cation, or an organic group of up to 30 C atoms, and R3 and R4 are independently H or an organic group of up to 30 C atoms, provided that R3 and R4 are not both H, in the presence of a transition metal complex of a chiral phosphine ligand having the partial formula 10 wherein n is 0 to 6 and R represents at least one non-hydrogen organic group of up to 30 C atoms.Type: GrantFiled: December 17, 1998Date of Patent: March 27, 2001Assignee: Chirotech Technology, Inc.Inventors: Mark Joseph Burk, Frank Bienewald, Martin Edward Fox, Antonio Zanotti-Gerosa
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Patent number: 6197987Abstract: The present invention relates to chemically stable, polyfunctional, perfluorinated polyorganosiloxanes (POS) comprising on the one hand fluorinated lateral grafts resulting from the hydrosilylation of perfluorinated olefins with SiH units and having alkyl and/or alkyl ester linkages but not ether linkages, and on the other hand other, non-perfluorinated functional units E capable of giving them diverse and varied physical and chemical properties and opening up avenues in numerous applications. Examples of these POS according to the invention are those of the following formula: According to another of its features, the invention relates to a process for the preparation of these polyfunctional perfluorinated POS. Applications: antifoams, agents for lowering surface tension, dirt repellents, antiadhesives, lubricants, oleophobic and/or hydrophobic agents, coatings etc.Type: GrantFiled: February 9, 1999Date of Patent: March 6, 2001Assignee: Rhone-Bouling ChimieInventors: Philippe Jost, Philippe Karrer, Gérard Mignani, Philippe Olier
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Patent number: 6184411Abstract: The invention is directed to an improved process for the preparation of a compound of formula (I) wherein R is alkyl, n is 0 to 2, m is 1 to 4 and A is alkyl, interrupted or uninterrupted alkylene, alkanetriyl or pentaerythrityl, by transesterifying the corresponding lower alkyl with a higher alkanol of the formula A-(OH)m in the presence of a tin catalyst; wherein the improvement comprises reacting the tin catalyzed transesterification reaction mass with a carboxylic acid or hydrate thereof neat, in the absence of an aqueous medium, until the tin catalyst forms an insoluble derivative, and then separating the insoluble derivative from the reaction mass by filtration without the assistance of a filtration aid. The invention allows for a convenient method by which to remove the residual tin catalyst from the substituted hydroxyphenylcarboxylic acid ester compounds of formula (I).Type: GrantFiled: January 28, 1999Date of Patent: February 6, 2001Assignee: Ciba Specialty Chemicals CorporationInventor: John Richard Ross
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Patent number: 5969177Abstract: The invention relates to a series of novel alkoxylated fluoro esters which contain a terminal carboxy group. This class of compounds provides unique solubility in many organic solvents as well as very substantive salts of the carboxylic acid when neutralized with base. In addition, the compounds of the present invention have tremendous spreadability when applied to substrate. The compounds of the present invention are prepared by reacting a the hydroxyl group in a fluoro alcohol with an anhydride.Type: GrantFiled: February 2, 1998Date of Patent: October 19, 1999Assignee: Petroferm IncInventors: Anthony J. O'Lenick, Jr., Jeff K. Parkinson, Robert T. Torbush
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Patent number: 5750711Abstract: The dicarboxylic acid derivatives according to the invention have the following structure ##STR1## wherein X denotes O, S, (CF.sub.2).sub.m, C(CF.sub.3).sub.2 or CF.sub.2 --CF(CF.sub.3) (m=1 to 10), and R stems from the following compounds: fluoro- or trifluoromethyl- and nitro- or cyanophenols, thiophenols or -aminobenzenes, 4-hydroxy-, 4-mercapto- or 4-aminocoumarins, N-hydroxysuccinimides or N-hydroxymaleimides, 2-hydroxy- or 2-mercaptobenzoxazoles or -benzothiazoles and 1-hydroxy- or 1-mercaptobenzotriazoles.Type: GrantFiled: August 28, 1996Date of Patent: May 12, 1998Assignee: Siemens AktiengesellschaftInventors: Racai Sezi, Hellmut Ahne, Eberhard Kuehn
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Patent number: 5424474Abstract: The present invention relates to fluorinated carboxylic acid esters of phosphono- and phosphinocarboxylic acids containing hydroxyl and/or mercapto groups, their use as waterproofing and/or oil-repellency agents, and a method for their preparation.Type: GrantFiled: December 23, 1993Date of Patent: June 13, 1995Assignee: Bayer AGInventors: Klaus Pohmer, Rainer Weber, Hans-Dieter Block, Hans-Heinrich Moretto
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Patent number: 5414102Abstract: The present invention relates to fluorinated carboxylic acid esters of phosphonocarboxylic acids containing acrylate and/or methacrylate groups, their use as waterproofing or oil-repellency agents, and a method for their preparation.Type: GrantFiled: December 27, 1993Date of Patent: May 9, 1995Assignee: Bayer AktiengesellschaftInventors: Klaus Pohmer, Rainer Weber, Hans-Dieter Block, Hans-Heinrich Moretto
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Patent number: 5393820Abstract: Flame retardant polyesters are disclosed comprising esters of tribromoneopentyl alcohol with orthophthalic acid and its halogenated derivatives, particularly tetrabromo-orthophthalic acid an hydride.Type: GrantFiled: November 3, 1992Date of Patent: February 28, 1995Assignee: The Associated Octel Company LimitedInventors: Paul Ashworth, Michael J. Schneider
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Patent number: 5370821Abstract: The invention relates to optically active compounds represented by the general formula ##STR1## wherein R.sub.1, R.sub.2, Q.sub.1, Q.sub.2, Q.sub.3, ##STR2## and M are defined as in the specification, methods and intermediates for their preparation, liquid crystal compositions comprising at least one optically active compound of formula I and their use in electrooptical display, switching and modulation devices.Type: GrantFiled: January 11, 1993Date of Patent: December 6, 1994Assignees: Takeda Chemical Industries, Ltd., Hitachi, Ltd.Inventors: Koichi Matsumura, Mitsuru Kawada, Yoshitaka Uesugi, Yuka Sudo, Katsumi Kondo, Teruo Kitamura
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Patent number: 5360575Abstract: An optically active lactic acid derivative having the formula (1a): ##STR1## wherein A is O or S; B is --(CH.sub.2).sub.m -- or --(CH.sub.2).sub.n --O; R1 is an alkoxy group having 1-22 carbon atoms, a phenolate, a substituted phenolate, a hydroxy group, or a halogen atom; R2 is an alkyl group having 2-8 carbon atoms; m is 0, 1, 2, 3 or 4; n is 2, 3, 4 or 5; C* is an asymmetric carbon atom. Liquid crystal compositions and liquid crystal devices containing the above mentioned derivatives are also disclosed.Type: GrantFiled: November 8, 1991Date of Patent: November 1, 1994Assignee: Industrial Technology Research InstituteInventors: Wen-Liang Tsai, Hwei-Long Kuo
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Patent number: 5275757Abstract: Novel anti-ferroelectric liquid crystal compounds represented by the following general formula (I) and a liquid crystal display element wherein such a compound is used. ##STR1## Ph represents a phenylene group, R represents a straight-chain alkyl group having 6 to 10 carbon atoms,X represents an oxygen atom or a single bond provided that when X is an oxygen atom, L is an integer of 5 to 8, m is 1 and n is an integer of 1 to 7, or L and m are zero (0) and n is an integer of 6 to 8, and when X is a single bond,L is an integer of 5 to 8, m is 1 and n is an integer of 1 to 7, andC* represents an asymmetric carbon atom.Type: GrantFiled: December 4, 1992Date of Patent: January 4, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hiroshi Mineta, Tomoyuki Yui, Takahiro Matsumoto
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Patent number: 5269965Abstract: The invention relates to optically active compounds represented by the general formula ##STR1## wherein R.sub.1, R.sub.2, Q.sub.1, Q.sub.2, Q.sub.3, ##STR2## and M are defined as in the specification, methods and intermediates for their preparation, liquid crystal compositions comprising at least one optically active compound of formula I and their use in electrooptical display, switching and modulation devices.Type: GrantFiled: April 15, 1993Date of Patent: December 14, 1993Assignees: Takeda Chemical Industries, Hitachi, Ltd.Inventors: Koichi Matsumura, Mitsuru Kawada, Yoshitaka Uesugi, Yuka Sudo, Katsumi Kondo, Teruo Kitamura
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Patent number: 5194667Abstract: This invention relates to fiber surface treating agnets containing a pyromellitate nucleus which have fungicidal, anti-microbial and anti-static properties, and blends of such agents with other types of surface modifiers.Type: GrantFiled: March 5, 1990Date of Patent: March 16, 1993Assignee: Allied-Signal Inc.Inventors: Bryce C. Oxenrider, David J. Long
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Patent number: 5117041Abstract: Allyl end-capped propylene terephthalate polyester oligomers are sulfonated in an aqueous system in the presence of a free radical initiator by a process in which only a part (about 15% to 40%) of the source of bisulfite is added at the start of the sulfonation step with the remainder being added later in that step, in such increments as will permit maintaining a clear single phase, to give sulfinate-containing sulfonated products, following which the sulfinate content is oxidized to give sulfonated end-capped propylene terephthalate polyester oligomers.Type: GrantFiled: November 13, 1990Date of Patent: May 26, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Edward F. McBride
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Patent number: 5073570Abstract: The new compositions of matter of the present invention comprise compounds having one of the following formulas: ##STR1## wherein: R is hydrogen or methyl;n is 1 to 16;R.sub.1 and R.sub.2 are defined as R.sub.3 and R.sub.4 below or are joined to form a cycloalkyl, cycloalkenyl, aromatic or a heterocyclic ring containing an oxygen, nitrogen or sulfur atom or an alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl substituted derivative thereof;R.sub.3 and R.sub.4 are independently selected from (A) hydrogen, alkyl, cycloalkyo, alkenyl, cycloalkenyl, aryl, a heterocyclic ring containing an oxygen, nitrogen or sulfur atom, alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl and (B) substituted derivatives of the alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl and the heterocyclic ring wherein the substitutions are alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl;W may be a single bond, oxygen, NR.sub.5, or (CR.sub.6 R.sub.7).Type: GrantFiled: February 16, 1989Date of Patent: December 17, 1991Assignee: Lonza Inc.Inventor: Chuen-Ing J. Tseng
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Patent number: 5023380Abstract: Compounds have a structure represented by Formula I:CF.sub.2 =CF-X-R-(X-CF=CF.sub.2).sub.mwherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF=CF.sub.2 ; and m is an integer of from 1 to about 3. Polymers formed from such compounds are also prepared. The compounds are preferably prepared by a method by a process comprising the steps of:(a) forming a salt having anion corresponding to a compound of Formula II:HX--R--(XH).sub.m ;wherein X, R and m are as defined for Formula I;(b) reacting the salt with a 1,2-dihalo-1,1,2, 2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III:Z-CF.sub.2 CF.sub.2 -X-R-(X-CF.sub.2 CF.sub.2 - Z).sub.Type: GrantFiled: June 9, 1989Date of Patent: June 11, 1991Assignee: The Dow Chemical CompanyInventors: David A. Babb, Bobby R. Ezzell, Katherine S. Clement
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Patent number: 4992504Abstract: Composition containing a chlorine-containing polymer and at least one compound of the formula IA ##STR1## in which R.sup.1 and R.sup.3 independently of one another are C.sub.1 -C.sub.12 alkyl, phenyl, phenyl which is substituted by one to three C.sub.1 -C.sub.12 alkyl groups, C.sub.7 -C.sub.10 phenylalkyl or C.sub.7 -C.sub.10 phenylalkyl which is substituted on the phenyl ring by one to three C.sub.1 -C.sub.12 alkyl groups and R.sup.1 is additionally --R.sup.2 --X--R.sup.3, R.sup.2' is C.sub.1 -C.sub.10 alkylene, R.sup.4 is hydrogen, C.sub.2 -C.sub.5 alkoxycarbonyl or C.sub.2 -C.sub.5 alkanoyl and X is oxygen or sulfur.Compounds of the formula IA in which R.sup.Type: GrantFiled: January 5, 1990Date of Patent: February 12, 1991Assignee: Ciba-Geigy CorporationInventors: Hermann O. Wirth, Hans-Helmut Friedrich
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Patent number: 4990633Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.Type: GrantFiled: May 4, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
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Patent number: 4939289Abstract: This invention relates to fiber surface treating agents containing a pyromellitate nucleus which have fungicidal, anti-microbial and anti-static properties, and blends of such agents with other types of surface modifiers.Type: GrantFiled: May 6, 1988Date of Patent: July 3, 1990Assignee: Allied-Signal Inc.Inventors: Bryce C. Oxenrider, David J. Long
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Patent number: 4929750Abstract: Oligomeric and polymeric derivativies of 1,10-bis(2-hydroxyethylthio)decane, processes for the preparation thereof and their therapeutic use.Type: GrantFiled: July 22, 1988Date of Patent: May 29, 1990Assignee: Nuovo Consorzio Sanitario NazionaleInventors: Paolo Ferruti, Giancarlo Scapini
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Patent number: 4898970Abstract: This invention relates to a process for producing a fluorinated ester containing a trifluoromethyl group by esterification in the presence of .gamma.-butyrolactone as a solvent, and more particularly a process or producing a fluorinated ester containing a trifluoromethyl group which is useful as a raw material of various fluorine containing compound.Type: GrantFiled: February 1, 1983Date of Patent: February 6, 1990Assignees: Onoda Cement Co., Ltd., Tosoh CorporationInventors: Eiji Ogura, Kunihiro Mito, Shoji Arai
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Patent number: 4721580Abstract: Oligomeric esters and mixtures thereof useful as soil release agents in consumer laundering and fabric care compositions are disclosed. Preferred oligomers have the formulae ##STR1## wherein E is ##STR2## wherein the R substituents may be the same or different and are members selected from the group consisting of --CH.sub.2 CH(CH.sub.3)--, --CH(CH.sub.3)CH.sub.2 --and --CH.sub.2 CH.sub.2 --, n is an integer from 1 to 30 and x is an integer from 0 to about 20 provided that when E is ##STR3## x is at least 1. Mixtures of the oligomers having one and two NaO.sub.3 S(CH.sub.2 CH.sub.2 O).sub.n --substituents are particularly effective and formulable soil release agents in detergent compositions.Type: GrantFiled: January 7, 1987Date of Patent: January 26, 1988Assignee: The Procter & Gamble CompanyInventor: Eugene P. Gosselink
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Patent number: 4717494Abstract: A liquid thermal accumulator composition comprising a dicarboxylic acid anhydride, an alcohol and a monoester of the dicarboxylic acid and the alcohol. A process for accumulation of thermal energy utilizing said composition is also disclosed.Type: GrantFiled: June 25, 1986Date of Patent: January 5, 1988Assignee: UBE Industries, Ltd.Inventors: Hiroshi Itatani, Mikito Kashima, Masami Aikawa
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Patent number: 4681974Abstract: A fluorine-containing polymer comprising units of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are, the same or different, a fluorine-containing organic group, R.sup.3 and R.sup.4 are, the same and different, hydrogen or a lower acyl group, and Q.sup.1 and Q.sup.2 are, the same or different, a divalent organic group with at least one oxy group, which polymer having a number average molecular weight of 5,000 to 100,000, which is easily dissolved in oils and lowers surface tension thereof.Type: GrantFiled: April 23, 1985Date of Patent: July 21, 1987Assignee: Daikin Industries Ltd.Inventors: Iwao Hisamoto, Masayuki Yamana
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Patent number: 4647284Abstract: Perfluoroalkyl-alkyl-sulfide or sulfonyl-alkylene esters of meta- and para-pyromellitates, partially esterified with 3-chloro-1,2-propane diol, of the formulae: ##STR1## or mixtures thereof, wherein R.sub.f is perfluoroalkyl of 3 to 18 carbon atoms, andm is 0 or 2, are useful for incorporation into organic polymers to render them oil repellent and soil resistant.Type: GrantFiled: October 28, 1985Date of Patent: March 3, 1987Assignee: Ciba-Geigy CorporationInventors: Athanasios Karydas, Robert A. Falk
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Patent number: 4613681Abstract: This invention relates to a process for the preparation of a fluorinated compound of the general formulaR.sub.F C.sub.2 H.sub.4 ORcomprising reacting an iodide of the general formula R.sub.F C.sub.2 H.sub.4 I with a percarboxylic acid of the general formula R.sup.1 CO.sub.3 H at a temperature and for a time sufficient to form said fluorinated compound; in said formulae R.sub.F is a straight or branched chain perfluorinated radical containing 1 to 20 C atoms, R is a hydrogen atom or --COR.sup.1, and R.sup.1 is a hydrogen atom or an aliphatic or aromatic hydrocarbon radical.Type: GrantFiled: June 30, 1980Date of Patent: September 23, 1986Assignee: Produits Chimiques Ugine KuhlmannInventors: Louis Foulletier, Andre Lantz
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Patent number: 4605587Abstract: Improved retention on yarn and processing properties have been discovered in a composition of matter comprising meta and para pyromellitates ##STR1## and 2 to 50 percent by weight of specific dimers of I. and II., wherein A is (CH.sub.2).sub.2 (CF.sub.2).sub.n CF.sub.3, where n is 5 to 13 and B is CH.sub.2 CHOHCH.sub.2 Cl.Type: GrantFiled: February 19, 1982Date of Patent: August 12, 1986Assignee: Allied CorporationInventors: Robert H. Thomas, Willis B. Hammond, Michael P. Friedberger, William A. Archie
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Patent number: 4604316Abstract: Improved retention on yarn and processing properties have been discovered in a composition of matter comprising meta and para pyromellitates ##STR1## and 70 to 95 percent by weight of specific dimers and other oligomers of I. and II., wherein A is (CH.sub.2).sub.2 (CF.sub.2).sub.n CF.sub.3, where n is 5 to 13 and B is CH.sub.2 CHOHCH.sub.2 Cl.Type: GrantFiled: September 14, 1982Date of Patent: August 5, 1986Assignee: Allied CorporationInventors: Robert H. Thomas, deceased, by Mary A. Thomas, executrix, Willis B. Hammond, Michael P. Friedberger, William A. Archie
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Patent number: 4551519Abstract: A novel process is disclosed for producing fluorinated pyromellitate surfactants. The process comprises two primary steps. The first step involves reacting pyromellitic dianhydride with fluorinated alcohol at a mole ratio of about two moles of fluorinated alcohol per mole of pyromellitic dianhydride, thereby producing a pyromellitate having two fluorinated esters moieties and two carboxylic acid moieties. Thereafter, the fluorinated pyromellitate with carboxylic acid moieties is reacted with an oxirane compound in the presence of trimellitic anhydride to produce fluorinated pyromellitate mixtures having a reduced percentage of fluorine.Type: GrantFiled: May 2, 1983Date of Patent: November 5, 1985Assignee: Allied CorporationInventor: Bryce C. Oxenrider
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Patent number: 4546155Abstract: A latent curing agent for epoxy resin, characterized in that the latent curing agent is an adduct obtained by reacting (a) a polyfunctional epoxy compound, (b) a compound having at least one OH, NH.sub.2, NH or SH group together with a tertiary amino group in the molecule and (c) a carboxylic acid anhydride is a good curing agent for epoxy resins. The present curing agent is useful in formulating storable, one-package, heat-curable epoxy resin-based compositions.Type: GrantFiled: September 26, 1984Date of Patent: October 8, 1985Assignee: Ajinomoto Co., Inc.Inventors: Takeshi Hirose, Nobuo Ito, Kiyomiki Hirai, Koji Takeuchi
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Patent number: 4537728Abstract: Novel polycarboxy benzene dianhydrides useful as surfactants are disclosed. The novel compounds of this invention are pyromellitate tetraesters wherein two ester moieties characteristically contain fluorinated alkyl groups or saturated hydrocarbon alkyl groups and wherein two ester moieties contain alkylene moieties having a terminal halogen.Type: GrantFiled: September 30, 1982Date of Patent: August 27, 1985Assignee: Allied CorporationInventors: Bryce C. Oxenrider, David J. Long
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Patent number: 4536522Abstract: The present invention is directed to the manufacture of polyols and polyurethanes using thiodialkylene glycols. More particularly, the present invention is directed to the manufacture of rigid polyurethane foam using novel polyols prepared by forming a condensation product of a polyethylene terephthalate with a low molecular weight glycol having a molecular weight of about 500 or less and a thiodialkylene glycol such as thiodiethylene glycol. The present invention is also directed to the use of thiodialkylene glycols as cross linking agents in the preparation of polyurethane foam from condensation products prepared by digesting a polyethylene terephthalate with a polyol having a molecular weight of about 500 or less such as a glycol or a triol.Type: GrantFiled: July 18, 1984Date of Patent: August 20, 1985Assignee: Texaco Inc.Inventors: Robert A. Grigsby, Jr., George P. Speranza, Michael E. Brennan, Ernest L. Yeakey
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Patent number: 4517376Abstract: Compounds having the formula: ##STR1## wherein R.sub.f is perfluorinated saturated aliphatic containing 3-20 carbons;R.sup.1 is optionally substituted alkyl, aryl, aralkyl or cycloalkyl; andn is a number from 1 to 4.Process for preparing compounds (I): ##STR2## The reaction can be carried out, e.g., by melting an iodine-substituted polyfluoroalkyl ester and contacting the molten ester with chlorine, or an iodine-substituted polyfluoroalkyl ester can be suspended or dissolved in a suitable liquid and reacted with chlorine. A suitable liquid is inert under the reaction conditions; e.g. alcohols or water should be avoided. Process of using compounds (I) to treat (a) textile materials so as to give them dry soil resistance and oil and water repellency, and (b) paper so as to make it repel water and oil.Type: GrantFiled: August 23, 1982Date of Patent: May 14, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventors: Stanley E. Krahler, William R. Remington
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Patent number: 4460785Abstract: Pyromellitate diester-diacid chlorides are disclosed that are useful as intermediates in the synthesis of a variety of soil and water repelling compounds. The pyromellitates of this invention characteristically contain two ester moieties wherein said ester moieties contain a fluorinated or saturated hydrocarbon alkyl moiety. The pyromellitates additionally contain two acid chloride moieties which are capable of reacting with various compounds to produce various products useful as surfactants.Type: GrantFiled: September 30, 1982Date of Patent: July 17, 1984Assignee: Allied CorporationInventors: Bryce C. Oxenrider, David J. Long
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Patent number: 4446306Abstract: A reaction between pyromellitic dianhydride (PMDA) and less than two moles of fluoroalcohol produces an intermediate with ester, free acid and anhydride groups. Reaction with an oxirane compound such as epichlorohydrin reacts at the acid sites to produce pendant hydroxyls which react with anhydride on adjacent molecules to produce oligomers. Products with fluoroalcohol:PMDA ratios of, for example, about 1:0.6 to about 1:0.85 produce treated fibers with improved retention of oil repellancy, especially when annealed at 100.degree.-130.degree. C.Type: GrantFiled: May 20, 1982Date of Patent: May 1, 1984Assignee: Allied CorporationInventor: Bryce C. Oxenrider
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Patent number: 4435294Abstract: Oligomers containing pyromellitic rings, divalent linking groups, pendant fluoroalkoxy or hydrocarbon alkoxy groups and pendant polar groups of various kinds impart soil repellency to fibers that persists after repeated laundering. An exemplary material is prepared by the reaction of pyromellitic difluoroester/diacid chloride with 1,4-butanediol (the linking group) and 3-chloro-1,2-propanediol (the pendant polar group).Type: GrantFiled: September 30, 1982Date of Patent: March 6, 1984Assignee: Allied CorporationInventors: Bryce C. Oxenrider, David J. Long
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Patent number: 4410717Abstract: Tetraesters of pyromellitic dianhydride are disclosed wherein two ester moieties are saturated hydrocarbon groups and two ester moieties are halohydroxyalkyl groups. The compounds may be used as diluents for fluorinated pyromellitates that are useful as soil and water repelling agents. Mixtures formed by dissolving the compounds of this invention and known fluorinated pyromellitates in a common solvent are capable of imparting soil and water repelling properties to various fibers that are essentially equivalent to soil and water repelling properties imparted to such fibers by fluorinated pyromellitates alone. Additionally, the hydrocarbon pyromellitates of this invention may be used alone as water repellents.Type: GrantFiled: May 5, 1982Date of Patent: October 18, 1983Assignee: Allied CorporationInventors: Bryce C. Oxenrider, Alson K. Price
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Patent number: 4395566Abstract: An improved process for exterifying carboxyaromatics is disclosed wherein an anhydride of a carboxyaromatic, such as pyromellitic dianhydride, is reacted with a fluorinated alcohol and an epoxide to give a mixed ester capable of imparting oil and/or water repellency to textiles. The improvement comprises utilizing the epoxide as the reaction medium to reduce reaction times and waste water treatment requirements.Type: GrantFiled: March 8, 1982Date of Patent: July 26, 1983Assignee: American Hoechst CorporationInventors: James H. Covill, Michael G. Kelly, Thomas F. Leahy
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Patent number: 4386103Abstract: Dichloroamino acid derivatives other than .alpha.-dichloroamino acids are prepared from chlorination of corresponding amino acids, and are found to be potent germicidal and fungicidal agents.Type: GrantFiled: January 30, 1981Date of Patent: May 31, 1983Assignee: Merck & Co., Inc.Inventors: Stefano A. Pogany, Takeru Higuchi
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Patent number: 4369329Abstract: Ethers of 1,2-disubstituted tartaric acid esters proved to be excellent initiators for thermally initiatable radical polymerization reactions. They show a high reactivity even in low concentrations and yield thoroughly hardened products.Type: GrantFiled: March 10, 1980Date of Patent: January 18, 1983Assignee: Bayer AktiengesellschaftInventors: Heinrich Wolfers, Hans Rudolph, Heinrich Alberts