Acylated Oxy In Acid Moiety Patents (Class 560/185)
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Patent number: 5633020Abstract: A coating composition with a solids content of at least about 65% by weight comprises a polyanhydride having more than one non-cyclic anhydride moiety, a co-reactant resin such as a glycidyl (meth)acrylate-containing polymer and a latent catalyst wherein the equivalent ratio of epoxy to anhydride is from about 0.8:1 to 1.3:1.Type: GrantFiled: October 4, 1995Date of Patent: May 27, 1997Assignee: The Dow Chemical CompanyInventors: Michael L. Gould, David A. Grilli, Marvin L. Dettloff, Richard A. Hickner, James A. Rabon
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Patent number: 5612439Abstract: Novel functionalized peroxides which may be used as crosslinking, grafting and curing agents, initiators for polymerization reactions and as monomers for condensation polymerizations to form peroxy-containing polymers, which in turn can be used to prepare block and graft copolymers, have the following Formula I: ##STR1## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, X, Y.sup.1, Y.sup.2, Y.sup.3, Z.sup.1, Z.sup.2, x, y and z are as defined in the Summary of the Invention. The compounds of Formula I may be prepared by reacting hydroxy-containing tertiary hydroperoxides with diacid halides, phosgene, dichloroformates, diisocyanates, anhydrides and lactones to form the functionalized peroxides. These reaction products may be further reacted, if desired, with dialcohols, diamines, aminoalcohols, epoxides, epoxy alcohols, epoxy amines, diacid halides, dichloroformates and diisocyanates to form additional functionalized peroxides.Type: GrantFiled: June 6, 1995Date of Patent: March 18, 1997Assignee: Elf Atochem North America, Inc.Inventor: Daryl L. Stein
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Patent number: 5602274Abstract: A polyanhydride having a molecular weight of no more than about 2000 is useful in a coating composition with a coreactant resin such as an epoxy resin and comprises:(a) a polyvalent organic moiety;(b) a plurality of ester linkages bonded to the polyvalent organic moiety;(c) divalent organic moieties bonded to the ester linkages; and(d) non-cyclic anhydride moleties bonded to the divalent organic moleties.Type: GrantFiled: February 28, 1995Date of Patent: February 11, 1997Assignee: The Dow Chemical CompanyInventors: Michael L. Gould, David A. Grilli, Marvin L. Dettloff, Richard A. Hickner, James A. Rabon
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Patent number: 5559267Abstract: Chiral 1,4-diol cyclic sulfates and their use as precursors in the preparation of chiral phospholane ligands, and chiral complexes useful as catalysts for carrying out enantioselective reactions.Type: GrantFiled: May 24, 1995Date of Patent: September 24, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Mark J. Burk
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Patent number: 5557007Abstract: Novel unsaturated polylactone acrylates are produced by the reaction of an unsaturated polylactone, such as that produced in the reaction of a lactone with tetrahydrobenzyl alcohol, and a lower-alkyl acrylate under transesterification conditions. The unsaturated polylactone acrylate product may be subsequently epoxidized to form novel 3,4-epoxy polylactone acrylates.Type: GrantFiled: September 28, 1990Date of Patent: September 17, 1996Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: James P. Stanley
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Patent number: 5519161Abstract: Novel compositions that are useful as nutrients are disclosed. These compounds are preferably water soluble parenteral nutrients and are glycerol esters of .beta.-acyloxybutyrates of the formula ##STR1## wherein each R is the same or different and is hydrogen, or --COCH.sub.2 CHOR'CH.sub.3), provided that at least one R is not hydrogen and wherein R' is a linear acid ester of even carbon number from 2 to 20 carbons. These compositions are useful as a substitute for glucose in feeding.Type: GrantFiled: May 3, 1995Date of Patent: May 21, 1996Inventors: Ronald H. Birkhahn, Robert J. Clemens, Charles A. McCombs, John C. Hubbs
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Patent number: 5434289Abstract: A process for producing an optically active .beta.-hydroxyketone represented by formula (I): ##STR1## by catalytic asymmetrical aldol reaction is disclosed, comprising reacting a silyl-enol ether represented by formula (II): ##STR2## with a substituted aldehyde represented by formula (III):R.sup.5 CHO (III)in the presence of a binaphthol-titanium complex represented by formula (IV): ##STR3## An optically active .beta.-hydroxyketone is efficiently produced with diastereo-specificity and enantio-specificity.Type: GrantFiled: March 10, 1994Date of Patent: July 18, 1995Assignee: Takasago International CorporationInventors: Koichi Mikami, Satoru Matsukawa, Masaki Shimizu, Masahiro Terada, Noboru Sayo
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Patent number: 5412134Abstract: The protected cyclobutanone of the formula ##STR1## is treated with a dialkylaluminum chloride, an alkylaluminum dichloride, a trialkylaluminum compound, diphenylsilane in the presence of tris(triphenylphosphine) rhodium (I) chloride, or iridium tetrachloride to yield the corresponding diprotected cyclobutanol. This compound is useful as an intermediate in the preparation of antiviral agents.Type: GrantFiled: May 26, 1992Date of Patent: May 2, 1995Assignee: E. R. Squibb & Sons, Inc.Inventors: Janak Singh, Gregory S. Bisacchi, Richard H. Mueller
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Patent number: 5374366Abstract: A synthetic lubricating oil contains an esterification product obtained from a hydroxycarboxylic acid polyol ester (A) and at least one aliphatic monocarboxylic acid (B), and optionally either an aliphatic carboxylic acid having two or more carboxyl groups (C) or a combination of an aliphatic carboxylic acid having two or more carboxyl groups (C) and an aliphatic polyhydric alcohol (D).Type: GrantFiled: February 18, 1993Date of Patent: December 20, 1994Assignee: Sanken Chemical Co., Ltd.Inventors: Makoto Nakahara, Katsuhiro Fujii, Masao Izumi
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Patent number: 5338879Abstract: A composition comprising a lactone-modified alicyclic compound (I), or an epoxidized lactone-modified alicyclic compound (II) of the following formulae: ##STR1## wherein R is an alkyl group, an aromatic group or an alkenyl group having carbon number of from 1 to 30, Y.sup.1 is at least one of the structural groups; ##STR2## Y.sup.2 is at least one of the structural group; ##STR3## X is the structural group; ##STR4## and R.sup.a and R.sup.b each independently is hydrogen or a methyl group, c and c' represent a number of from 4 to 8, from n1 to nL represents 0 or a number of more than 0, respectively, and n1+n2+n3+ . . . +nL corresponds to the total mole numbers of a lactone introduced into one molecule.These compositions can be made into a heat-curable composition, a photo-curable composition, a polymerizable composition and another photo-curable composition.Type: GrantFiled: August 13, 1992Date of Patent: August 16, 1994Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Fujiwa, Shin Takemoto, Tomohisa Isobe, Yoshiyuki Harano
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Patent number: 5324856Abstract: Disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) separating the diastereomers by conventional physical means and (3) hydrolyzing at least one of said separated diastereomers to make at least the .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid.Also disclosed is a process for making an .alpha.Type: GrantFiled: August 17, 1992Date of Patent: June 28, 1994Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 5319130Abstract: Novel functionalized peroxides which may be used as crosslinking, grafting and curing agents, initiators for polymerization reactions and as monomers for condensation polymerizations to form peroxy-containing polymers, which in turn can be used to prepare block and graft copolymers, have the following Formula I: ##STR1## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, X, Y.sup.1, Y.sup.2, Y.sup.3, Z.sup.1, Z.sup.2, x, y and z are as defined in the Summary of the Invention. The compounds of Formula I may be prepared by reacting hydroxy-containing tertiary hydroperoxides with diacid halides, phosgene, dichloroformates, diisocyanates, anhydrides and lactones to form the functionalized peroxides. These reaction products may be further reacted, if desired, with dialcohols, diamines, aminoalcohols, epoxides, epoxy alcohols, epoxy amines, diacid halides, dichloroformates and diisocyanates to form additional functionalized peroxides.Type: GrantFiled: June 25, 1992Date of Patent: June 7, 1994Assignee: Elf Atochem North America, Inc.Inventor: Daryl L. Stein
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Patent number: 5296003Abstract: Poly(oxyalkylene) hydroxyaromatic ethers having the formula: ##STR1## or a fuel-soluble salt thereof; where n is an integer from 5 to 100; x is an integer from 0 to 10; R.sub.1 and R.sub.2 are each independently hydrogen, hydroxy, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; R.sub.3 and R.sub.4 are each independently hydrogen or lower alkyl having 1 to 6 carbon atoms; R.sub.5 is an acyl group of the formula: ##STR2## wherein y is 1, 2 or 3; R.sub.6 is a divalent hydrocarbyl radical, when y is 1, a trivalent hydrocarbyl radical, when y is 2, or tetravalent hydrocarbyl radical, when y is 3, said hydrocarbyl radicals having 1 to about 20 carbon atoms; and each Z is independently selected from the group consisting of: ##STR3## where each R.sub.7 is independently alkyl having 1 to 30 carbon atoms, phenyl, aralkyl having 7 to 36 carbon atoms or alkaryl having 7 to 36 carbon atoms.Type: GrantFiled: March 8, 1993Date of Patent: March 22, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5294733Abstract: Preparation of cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketene type compound of the formula (R.sub.1) (R.sub.2) C.dbd.C.dbd.O to give a polymer: ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1) (R.sub.2)--COOR.sub.3, the acids in the mixture are converted for esters. The hydroxy ester of the ester mixture is converted to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the product ##STR4## wherein: R is selected, e.g.Type: GrantFiled: May 20, 1993Date of Patent: March 15, 1994Assignee: Eastman Kodak CompanyInventor: Charles A. McCombs
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Patent number: 5277900Abstract: A method of using resorbable waxes for coagulation of blood on endogenous hard tissue, especially bone, which waxes consist of waxy polyester-oligomers of hydroxybarboxylic acids which are viscous to solid at body temperature. On the basis of their structure, these waxes are degradable by endogenous metabolic mechanism, wherein the rate of degradation can be adjusted.Type: GrantFiled: February 11, 1985Date of Patent: January 11, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Wolfgang Ritter
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Patent number: 5248809Abstract: A process for preparing a polymerizable compound of the formula: ##STR1## or a polymerizable compound of the formula: ##STR2## is provided. These formed compounds are useful for the preparation of an acrylic resin which is low in viscosity and capable of forming a coating with excellent flexibility, weather resistance and water resistance.Type: GrantFiled: November 7, 1989Date of Patent: September 28, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Ryozo Takagawa, Hisaki Tanabe, Yoshio Eguchi, Koichi Tsutsui
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Patent number: 5234972Abstract: A novel itaconic acid monoester compound represented by the following general formula (1) ##STR1## (R.sub.1 represents --H or --CH.sub.3, and R.sub.2 represents a C.sub.2 -C.sub.10 alkylene group, an oxyethylene group or a derivative thereof).The above compound is ordinarily synthesized from itaconic anhydride and a hydroxyalkyl ester of (meth)acrylic acid.Further, the above compound has hydrophilic groups and hydrophobic groups in appropriate balance, is superior in hardness, compression strength and water absorbability, and is suitable for use particularly in a dental adhesive comprising the compound or a polymer thereof. When the compound is used in a dental adhesive, the dental adhesive shows strong adhesion to the teeth or a composite resin over a long period even under a wet condition inside the mouth, and has excellent durability.Type: GrantFiled: October 12, 1990Date of Patent: August 10, 1993Assignee: Ube Industries, Ltd.Inventors: Yoshihiro Saitoh, Kazusato Kanda, Kimio Fukuda
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Patent number: 5225589Abstract: Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketene type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3.Type: GrantFiled: February 3, 1992Date of Patent: July 6, 1993Assignee: Eastman Kodak CompanyInventor: Charles A. McCombs
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Patent number: 5213976Abstract: Process for extracting polyhydroxyalkanoates from the cell material of microorganisms by adding an organic solvent for the polyhydroxyalkanoate which is immiscible with water and which has a boiling point of below 100.degree. C., and, if appropriate, by adding water; stirring the resulting extraction mixture, if appropriate with refluxing; separating off the aqueous phase which contains the cell material in undissolved form from the organic phase; and injecting the organic phase into hot water, causing the dissolved polyhydroxyalkanoate to precipitate and the organic solvent to evaporate, and also isolating the precipitated polyhydroxyalkanoate flocs.Type: GrantFiled: September 17, 1991Date of Patent: May 25, 1993Assignee: PCD Polymere Gesellschaft m.b.H.Inventors: Wilfried Blauhut, Wolfgang Gierlinger, Friedrich Strempfl
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Patent number: 5169409Abstract: Reaction products which provide antioxidant properties to lubricants and fuels while serving as effective dispersants and detergents in these mediums. These products, of the reaction of a hydroxyalkylene substituted polyamines and substituted succinic anhydrides, contain mixtures of esters, amides and imides. Furthermore, preferred embodiments of the reaction products have pendent alcohol groups which provide extra dispersancy and detergency over traditional dispersants which typically do not have alcohol groups.Type: GrantFiled: May 17, 1990Date of Patent: December 8, 1992Assignee: Mobil Oil Corp.Inventors: David A. Blain, Angeline B. Cardis
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Patent number: 5142019Abstract: An oligomer of the structure: ##STR1## wherein R.sub.1 is hydrogen, lower alkyl having 1 to 5 carbon atoms or hydroxyalkyl having 1 to 5 carbon atoms; R.sub.2 and R.sub.3 are the same or different radicals selected from hydrogen, alkyl having 1 to 5 carbon atoms or one of R.sub.2 and one of R.sub.3 radicals joined together with the carbon atom to which they are attached to form cycloalkyl; R.sub.5 is hydrogen or methyl; R.sub.6 is alkyl having 1 to 6 carbon atoms, cycloalkyl of 5 to 6 carbon atoms and hydroxyalkyl of 2 to 6 carbon atoms. The oligomers can be used as reactive components with other materials containing co-reactive functional groups selected from hydroxyl, carboxylic acid, carboxylic acid anhydride and isocyanate. Reactive compositions can be formed which are useful as resinous film formers in coating applications which can be cured without the generation of formaldehyde.Type: GrantFiled: October 3, 1991Date of Patent: August 25, 1992Assignee: PPG Industries, Inc.Inventors: Padmanabhan Sundararaman, Rudolf Maska, Cynthia L. Verardi
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Patent number: 5136061Abstract: An optically active pentane compound of the general formula (I): ##STR1## wherein R.sub.1 represents a lower alkyl group having 1 to 4 carbon atoms, R.sub.2 represents a lower alkoxycarbonyl group having an alkoxy moiety of 1 to 4 carbon atoms, or a straight-chain or branched alkyl group having 1 to 7 carbon atoms which is unsubstituted or substituted with a hydroxy or protected hydroxy group, A represents a halogen atom, hydroxy, protected hydroxy, or ethynyl group, or a group of the formula ##STR2## B represents a hydrogen atom, hydroxy, protected hydroxy or acyloxy group, D represents a hydrogen atom, or A and B together can form an acetal or epoxy group, A and D together can form an ethylidene group, and B and D together can form a carbon-carbon direct bond, and a chiral central carbon atoms marked with symbols *, # and .thrfore. in said formula (I) alternatively have one of an R-configuration and an S-configuration.Type: GrantFiled: June 13, 1991Date of Patent: August 4, 1992Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5128252Abstract: The invention provides an optically active compound which is R- or S- ester having the general formula: ##STR1## wherein R.sup.1 is hydrogen or acyl of 2-20 carbon atoms, R.sup.2 is alkyl, alkenyl or alkynyl of 3-40 carbon atoms, and the carbon indicated by * is an asymmetric carbon atom.Type: GrantFiled: April 25, 1991Date of Patent: July 7, 1992Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Naoyuki Yoshida
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Patent number: 5117035Abstract: A novel fluorine-containing acrylic acid derivative of the invention is represented by the formula:(CH.sub.2 .dbd.CF--CO).sub.p --A (I)wherein A is a residue derived from an organic compound having at least two active hydrogen atoms derived by removing at least two active hydrogen atoms, and p is an integer corresponding to the valency of the residue A, which is easily cured.Type: GrantFiled: May 24, 1989Date of Patent: May 26, 1992Assignee: Daikin Industries, Ltd.Inventors: Shigeru Morita, Masahiko Oka
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Patent number: 5110980Abstract: Hypochlorite digestion of bacterial biomass to recover intracellular poly-.beta.-hydroxylalkanoic acid (PHA) has not been used on a large scale since it has been widely reported to severely degrade the polymer. The process of the invention proposes to optimize the initial biomass concentration, the digestion time and pH of the hypochlorite solution to minimize degradation. Consequently, PHA of up to 95% purity with an average molecular weight of 600,000 can be recovered from biomass initially containing PHA having a molecular weight of 1,200,000. By incorporating a pretreatment step with an anionic surfactant solution, PHA of 99% purity with a molecular weight of 1.20.times.10.sup.6 was obtained from biomass containing 57% PHA by weight with an initial molecular weight of 1.25.times.10.sup.6.Type: GrantFiled: September 20, 1989Date of Patent: May 5, 1992Assignee: Ecole PolytechniqueInventors: Bruce A. Ramsay, Juliana Ramsay, Eric Berger, Claude Chavarie, Gerhart Braunegg
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Patent number: 5091560Abstract: A method for synthesizing an acyloxycarboxylic acid by providing a reaction chamber, establishing sources of an .alpha.-hydroxycarboxylic acid and an acid chloride, and repeatedly contacting substantially equal molar amounts of the .alpha.-hydroxycarboxylic acid and the acid chloride within the reaction chamber. The acyloxycarboxylic acid so synthesized is useful as a starting material for conversion to various esters which, when placed in aqueous solution with a source of hydrogen peroxide, result in a peracid and are useful for bleaching applications.Type: GrantFiled: December 21, 1990Date of Patent: February 25, 1992Assignee: The Clorox CompanyInventor: Richard R. Rowland
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Patent number: 5081224Abstract: This invention relates to processes for producing an olefin-terminated polyester. In one of the processes which comprises reacting an olefin-terminated diester compound with a lactone in the presence of a polymerization catalyst with transesterification ability, the lactone is in a limited amount added to the reaction system. In another process which comprises reacting an olefin-terminated diester compound, a lactone compound, a cyclic acid anhydride and an epoxy compound in the presence of a polymerization catalyst with transesterification ability, the lactone, cyclic acid anhydride and epoxy compound are each in a limited amount added to the reaction system. In accordance with this invention, olefin-terminated polyesters having high terminal modification rates can be synthesized.Type: GrantFiled: October 12, 1990Date of Patent: January 14, 1992Assignee: Kanegafuchi Chemical Industry Co., Ltd.Inventors: Hiroshi Ando, Kazumasa Hashimoto, Jun Hattori, Kazuya Yonezawa
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Patent number: 5055609Abstract: Citrate esters are formed utilizing organic titanates as a catalyst allowing excess alcohol to be removed. Four citrate esters have been found which provide advantageous plasticizing properties to PVC compositions which include superior toxicity test results and superior soapy water extraction tests results. The four citrate esters are: acetyltri-n-hexyl citrate, n-butyryltri-n-hexyl citrate, acetyltri-n-(hexyl/octyl/decyl) citrate, and acetyltri-n-(octyl/decyl) citrate. Articles formed from the PVC plasticized mixtures are extremely useful in the medical or health care field as they demonstrate a low order of toxicity.Type: GrantFiled: April 6, 1990Date of Patent: October 8, 1991Assignee: Morflex, Inc.Inventors: Ezekiel H. Hull, Edward P. Frappier
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Patent number: 5051530Abstract: There are provided novel ester derivatives represented by the following formula(I): ##STR1## wherein, R.sub.1 represents methyl, ethyl, isopropyl, t-butyl, or phenyl; R.sub.2 represents phenyl, methoxy, ethoxy, isopropanoxy, or t-butanoxy; and X represents Br, and a process for preparing the same which comprises reacting an aldehyde of the formula (III) with an acid halide of the formula (IV) at 20.degree.-80.degree. C. in the presence or absence of solvents. ##STR2## Wherein, R.sub.1, R.sub.2 and X have the same meaning as defined above.Type: GrantFiled: January 16, 1990Date of Patent: September 24, 1991Assignee: Korea Institute of Science and TechnologyInventors: MoonHo Chang, Han-Young Kang, HunYeong Koh, YongSeo Cho, SangChul Shim
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Patent number: 5032320Abstract: C.sub.5 -C.sub.9 lactone based adduct materials are made by reacting a C.sub.5 -C.sub.9 lactone with a polyol to form a lactone adduct intermediate, and thereafter reacting the intermediate with an aliphatic hydrocarbyl saturated or unsaturated, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about one to about 165 total carbon atoms in said straight or branched chain to insure that the resulting lactone adduct is hydrocarbon soluble. The resulting adduct material are useful per se, as oil soluble dispersant additives, and are useful in fuel and lubricating oil compositions including concentrates containing the additives.Type: GrantFiled: February 28, 1991Date of Patent: July 16, 1991Assignee: Exxon Chemical Patents Inc.Inventors: Antonio Gutierrez, Robert D. Lundberg
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Patent number: 5025017Abstract: Seco-mevinic acid derivatives are provided which has the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis. New intermediates for preparing the above seco-mevinic acid derivatives are also provided.Type: GrantFiled: September 28, 1989Date of Patent: June 18, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
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Patent number: 5011973Abstract: The process for producing bischoline-disulfonate derivatives of Formula (I) ##STR1## useful for enhancing the digestive function comprising reacting, in the presence of an organic solvent, a trimethylammonium salt derivative of Formula (II) ##STR2## wherein R.sup.1 and R.sup.2 are individually lower alkyl and X is a group removable by a disulfonic acid of Formula (III)R(SO.sub.3 H).sub.2 (III)wherein R is a naphthylene, or an organic base salt of said acid.Type: GrantFiled: May 15, 1989Date of Patent: April 30, 1991Assignee: Toyama Chemical Co., Ltd.Inventors: Yasuyuki Suzuki, Noboru Takagawa, Mikio Kawabata, Mariko Hayashi, Akiko Takagi, Takako Wakamiya, Isamu Saikawa
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Patent number: 4983689Abstract: Preparation of a macromolecular monomer of a lactone having an alpha-beta monoolefinically unsaturated "head" is effected at low temperature with a strong oxonium salt, such as a trialkyloxonium (TAO) hexafluorophosphate catalyst, with essentially no formation of cyclic oligomers and an insignificant amount of diacrylate. Cationic ring-opening polymerization of lactone monomer in conjunction with an unsaturated alcohol (propagator) having an acryloyl or methacryloyl double bond, produces a polylactone macromer having an ethylenic double bond at one end and a hydroxyl group at the other. The polymerization proceeds by polyaddition of the lactone to the OH group which is the propagating species. The macromer so formed allows the preparation of a macromer of block copolymer of the polylactone with a polyether such as epichlorohydrin, using the same TAO catalyst. In such a macromer of block copolymer, the polylactone ester block is next to the double bond, followed by the polyether block.Type: GrantFiled: December 12, 1988Date of Patent: January 8, 1991Inventor: Simon H. Yu
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Patent number: 4983759Abstract: A compound of a 3,5,6-trihydroxyhexanoic acid derivative of the formula: ##STR1## wherein P.sup.1 and P.sup.2 are independently hydrogen atoms or hydroxy-protecting groups, or together form a ring, and R is an alkyl group is effectively prepared by a process comprising steps of:reacting a butyronitrile derivative of the formula: ##STR2## wherein P.sup.1 and P.sup.2 are the same as defined above with an .alpha.-haloacetate of the formula:X--CH.sub.2 --COOR (III)wherein X is a halogen atom, and R is the same as defined above in the presence of a metallic catalyst selected from the group consisting zinc and zinc-copper to form a keto acid derivative of the formula: ##STR3## wherein P.sup.1, P.sup.2 and R are the same as defined above, and then reducing the obtained keto-acid derivative of the formula (IV).Type: GrantFiled: December 20, 1989Date of Patent: January 8, 1991Assignee: Kanegafuchi Chemical Industry Co., Ltd.Inventors: Kenji Inoue, Satomi Takahashi, Keiichi Yonetsu, Noboru Ueyama
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Patent number: 4954649Abstract: Citrate esters are formed utilizing organic titanates as a catalyst allowing excess alcohol to be removed. Four citrate esters have been found which provide advantageous plasticizing properties to PVC compositions which include superior toxicity test results and superior soapy water extraction test results. The four citrate esters are: acetyltri-n-hexyl citrate, n-butyryltri-n-hexyl citrate, acetyltri-n-(hexyl/octyl/decyl) citrate, and acetyltri-n-(octyl/decyl) citrate. Articles formed from the PVC plasticized mixtures are extremely useful in the medical or health care field as they demonstrate a low order of toxicity.Type: GrantFiled: June 21, 1989Date of Patent: September 4, 1990Assignee: Morflex Chemical Company, Inc.Inventors: Ezekiel H. Hull, Edward P. Frappier
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Patent number: 4931583Abstract: Citrate esters are formed utilizing organic titanates as a catalyst allowing excess alcohol to be removed. Four citrate esters have been found which provide advantageous plasticizing properties to PVC compositions which include superior toxicity test results and superior soapy water extraction test results. The four citrate esters are: acetyltri-n-hexyl citrate, n-butyryltri-n-hexyl citrate, acetyltri-n-(hexyl/octyl/decyl) citrate, and acetyltri-n-(octyl/decyl) citrate. Articles formed from the PVC plasticized mixtures are extremely useful in the medical or health care field as they demonstrate a low order of toxicity.Type: GrantFiled: June 15, 1989Date of Patent: June 5, 1990Assignee: Morflex Chemical Compay, Inc.Inventors: Ezekiel H. Hull, Edward P. Frappier
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Patent number: 4916254Abstract: .epsilon.-caprolactone-modified hydroxyalkyl acrylate or methyacrylate can be effectively produced from .epsilon.-caprolactone and a hydroxyalkyl acrylate or methacrylate in the presence of a stannous halide as a catalyst. The obtained monomer is used together with another copolymerizable monomer to produce a copolymer which is suitable for coating and photocurable composition.Type: GrantFiled: September 9, 1988Date of Patent: April 10, 1990Assignee: Daicel Chemical Industries, Inc.Inventors: Shoji Watanabe, Kiyoshi Okitsu
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Patent number: 4902820Abstract: Disclosed is a process for the preparation of .alpha.-acyloxycarbonyl compounds by contacting the corresponding .alpha.-dicarbonyl compound with an acyl iodide, which can be employed in an essentially pure form or generated in solution from hydrogen iodide and a carboxylic acid anhydride.Type: GrantFiled: February 21, 1989Date of Patent: February 20, 1990Assignee: Eastman Kodak CompanyInventor: Joseph R. Zoeller
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Patent number: 4894181Abstract: Carbocyclic compounds of the formula I ##STR1## wherein Q is a benzene or cyclohexane ring or a naphthalene system, X is in each case --CH.sub.2 --(CH.sub.2).sub.p -- where it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,p is 0, 1 or 2,A.sup.1 and A.sup.2 independently of one another are each a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by halogen atoms and/or CH.sub.3 groups and/or CN groups and in which it would also be possible for one or more CH groups to be replaced by N atoms, a 1,4-cyclohexylene group wherein it would also be possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O-- and/or --S--, a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group,Z is --CO--O--, --O--CO--, --O--, --CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CHCN--CH.sub.2 --, --CH.sub.2 --CHCN--, --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --NO.Type: GrantFiled: May 16, 1988Date of Patent: January 16, 1990Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
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Patent number: 4892967Abstract: Citrate esters are formed utilizing organic titanates as a catalyst allowing excess alcohol to be removed. Four citrate esters have been found which provide advantageous plasticizing properties to PVC compositions which include superior toxicity test results and superior soapy water extraction test results. The four citrate esters are: acetyltri-n-hexyl citrate, n-butyryltri-n-hexyl citrate, acetyltri-n-(hexyl/octyl/decyl) citrate, and acetyltri-n-(octyl/decyl) citrate. Articles formed from the PVC plasticized mixtures are extremely useful in the medical or health care field as they demonstrate a low order of toxicity.Type: GrantFiled: July 11, 1988Date of Patent: January 9, 1990Assignee: Morflex Chemical Company, Inc.Inventors: Ezekiel H. Hull, Edward P. Frappier
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Patent number: 4888439Abstract: A novel polyprenyl compound is identified with the formula and useful for a pharmaceutical drag. ##STR1## wherein X represents a group of the formula: ##STR2## (wherein R.sup.1 and R.sup.2, which may be the same or different, represent each a hydrogen atom, a lower alkyl group, a hydroxyalkyl group, or a lower alkenyl group); a group of the formula: ##STR3## (wherein A including the nitrogen atom shown represents a ring containing nitrogen and oxygen atoms); or a group of the formula: ##STR4## (wherein R.sup.3 represents a hydrogen atom or a lower alkyl group, and R.sup.4 represents a lower alkyl group); Y represents a group of the formula: ##STR5## or a group of the formula: ##STR6## (wherein R.sup.5 represents a hydrogen atom or a lower alkyl group), and n represents an integer of from 2 to 5.Type: GrantFiled: May 1, 1985Date of Patent: December 19, 1989Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Kouji Nakamoto, Akiharu Kajiwara, Manabu Murakami, Kiyoshi Oketani, Hideaki Fujisaki
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Patent number: 4883905Abstract: Citrate esters are formed utilizing organic titanates as a catalyst allowing excess alcohol to be removed. Four citrate esters have been found which provide advantageous plasticizing properties to PVC compositions which include superior toxicity test results and superior soapy water extraction test results. The four citrate esters are: acetyltri-n-hexyl citrate, n-butyryltri-n-hexyl citrate, acetyltri-n-(hexyl/octyl/decyl) citrate, and acetyltri-n-(octyl/decyl) citrate. Articles formed from the PVC plasticized mixtures are extremely useful in the medical or health care field as they demonstrate a low order of toxicity.Type: GrantFiled: September 17, 1987Date of Patent: November 28, 1989Assignee: Morflex Chemical Company, Inc.Inventors: Ezekiel H. Hull, Edward P. Frappier
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Patent number: 4870204Abstract: Citrate esters are formed utilizing organic titanates as a catalyst allowing excess alcohol to be removed. Four citrate esters have been found which provide advantageous plasticizing properties to PVC compositions which include superior toxicity test results and superior soapy water extraction test results. The four citrate esters are: acetyltri-n-hexyl citrate, n-butylryltri-n-hexyl citrate, acetyltri-n-(hexyl/octyl/decyl) citrate, and acetyltri-n-(octyl/decyl) citrate. Articles formed from the PVC plasticized mixtures are extremely useful in the medical or health care field as they demonstrate a low order of toxicity.Type: GrantFiled: September 17, 1987Date of Patent: September 26, 1989Assignee: Morflex Chemical Company, Inc.Inventors: Ezekiel H. Hull, Edward P. Frappier
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Patent number: 4868236Abstract: The invention deals with the preparation, compositions, and application of certain high molecular weight hydrophobic citrate polyesters of guerbet alcohols and their alkoxylates, which are useful in polycarbonate processing.Type: GrantFiled: January 23, 1989Date of Patent: September 19, 1989Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 4843111Abstract: Disclosed herein are novel diesters of (meth)acrylic acid represented by the following formula: ##STR1## wherein the mean values of m and n are respectively 0 to 5, preferably 0 to 3, the mean value of m+n is 1 to 10, preferably 1 to 6, and R represents H or CH.sub.3.Also, disclosed herein are resin compositions comprising said diester(s) of (meth)acrylic acid, polyurethane (meth)acrylate(s), monoethylenically unsaturated monomer(s) and initiator(s) of photopolymerization as an optional component.Type: GrantFiled: January 21, 1987Date of Patent: June 27, 1989Assignee: Nippon Kayaku Kabushiki KaishaInventors: Minoru Yokoshima, Tetsuo Ohkubo, Hideaki Hattori, Masayuki Kiyomoto
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Patent number: 4801739Abstract: A product of an oligomer derived from glycolic acid and/or lactic acid, the oligomer having a molecular weight of from 500 to 10,000, the free carboxylic acid group of the oligomer being at least partially in the form of an amide with an amino acid or an ester with a sterol may be used as a matrix material for depot forms, containing pharmacologically active agents.Type: GrantFiled: December 16, 1983Date of Patent: January 31, 1989Assignee: Sandoz Ltd.Inventors: Joachim Franz, Walter Prikoszovich, Zdenek Brich
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Patent number: 4789726Abstract: A process for the manufacture of polyesters, especially polylactides or poly(lactide-co-glycolide) of specified low-medium molecular weight, by controlled hydrolysis of a higher molecular weight polyester.Type: GrantFiled: April 2, 1987Date of Patent: December 6, 1988Assignee: Imperial Chemical Industries PLCInventor: Francis G. Hutchinson
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Patent number: 4786749Abstract: Lactone acrylates and organic anhydrides are condensed to form carboxyl-terminated lactone acrylates. These can be homopolymerized or copolymerized with ethylenically unsaturated monomers by means of radiation.Type: GrantFiled: February 20, 1986Date of Patent: November 22, 1988Assignee: Union Carbide CorporationInventors: Joseph V. Koleske, George T. Kwiatkowski
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Patent number: 4776875Abstract: Compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 denote alkyl, OH, CF.sub.3 or cyanoethyl, A preferably denotes --COOH, R.sub.3 denotes inter alia alkoxycarbonylalkoxy, fairly high-molecular (>C.sub.12) alkoxy, alkylcarbonylalkoxy or nitrobenzyloxy, are valuable herbicides and growth regulators.Type: GrantFiled: March 26, 1986Date of Patent: October 11, 1988Assignee: Hoechst AktiengesellschaftInventors: Heinz J. Loher, Klaus Bauer, Hermann Bieringer
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Patent number: 4760061Abstract: Mono- or bis-complex esters or ethers of a phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined mono- or bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus; whereinA is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages, whereinR.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --, whereinR.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene; whereinR.sup.12 is hydrogen or alkyl, and whereinR.sup.22 is hydrogen, cyano or nitro; or a salt thereof when appropriate.Type: GrantFiled: April 24, 1985Date of Patent: July 26, 1988Assignee: Imperial Chemical Industries PLCInventors: Philip N. Edwards, Brian S. Tait