Preparing Esters From Alkylene Oxides Patents (Class 560/200)
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Patent number: 11518897Abstract: Provided are an ink composition including water, particles including a polymer having at least one selected from the group consisting of a urethane group and a urea group, and a gelling agent having a hydrogen-bonding group; a method for producing the ink composition; and an image-forming method.Type: GrantFiled: December 26, 2019Date of Patent: December 6, 2022Assignee: FUJIFILM CORPORATIONInventors: Ichiro Koyama, Shota Suzuki
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Patent number: 9193822Abstract: The invention relates to a process for producing polyester polyols with secondary hydroxyl end groups, including the step of the reaction of a polyester including carboxyl end groups with an epoxide of the general formula (1): wherein R1 stands for an alkyl residue or an aryl residue and the reaction is carried out in the presence of a catalyst that includes at least one nitrogen atom per molecule. The process is distinguished in that the polyester including carboxyl end groups exhibits an acid value from ?25 mg KOH/g to ?400 mg KOH/g and a hydroxyl value from ?5 mg KOH/g and in that the polyester including carboxyl end groups is produced by ?1.03 mol to ?1.90 mol carboxyl groups or carboxyl-group equivalents of an acid component being employed per mol hydroxyl groups of an alcohol. The polyester polyols obtained, including secondary hydroxyl end groups, can be used for the purpose of producing polyurethane polymers.Type: GrantFiled: May 4, 2010Date of Patent: November 24, 2015Assignee: Bayer MaterialScience AGInventors: Hartmut Nefzger, Erika Bauer, Jörg Hofmann, Klaus Lorenz, Bert Klesczewski
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Publication number: 20140357889Abstract: A method of synthesizing urethane-free polyfunctional acrylate compounds. The method includes reaction of a polyol with acrylic acid in the presence of an inhibitor. A catalyst may also be present. The catalyst may be an acid and the inhibitor may be a substituted phenol compound. Excess acid may be removed by adding a salt and excess water may be removed by adding a drying agent. The reaction converts alcohol groups of the polyol to acrylate groups to provide a radiation-curable polyfunctional acrylate compound. The reaction is applicable to polyols generally and provides a scalable high yield process for forming urethane-free polyfunctional acrylates over a wide range of molecular weights. Coatings made from the acrylate products exhibit modulus and tensile strength characteristics favorable for primary fiber coatings.Type: ApplicationFiled: April 23, 2014Publication date: December 4, 2014Applicant: Corning IncorporatedInventors: Kevin Robert McCarthy, Weijun Niu, David Neal Schissel, Arthur Lawrence Wallace
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Patent number: 8748558Abstract: Methods for producing biocompatible compositions are provided. The biocompatible compositions include an aliphatic polyester macromer produced without the use of solvents or catalysts. The resulting aliphatic polyester macromer may be reacted with a polyisocyanate to form an end-capped aliphatic polyester macromer which, in turn, may be reacted with a polyol to produce a polyurethane. The polyurethane, in turn, may be reacted with a second polyisocyanate to produce an isocyanate-functional polyurethane. The compositions prepared by the methods of the present disclosure may be used as adhesives or sealants for medical/surgical uses.Type: GrantFiled: April 21, 2008Date of Patent: June 10, 2014Assignee: Covidien LPInventors: Walter Skalla, Allison Calabrese, Ahmad R. Hadba, Nadya Belcheva
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Patent number: 8575378Abstract: Methods of producing plant polyols from plant oils include reacting a plant oil with a designed reactant having one or more nucleophilic functional groups and one or more active hydrogen functional groups in the presence of an addition reaction catalyst in a single reaction step. The resultant polyols may be directly reacted with polyisocyanates to produce polyurethanes.Type: GrantFiled: July 28, 2009Date of Patent: November 5, 2013Inventors: Thomas M. Garrett, Xian Xian Du
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Publication number: 20120259049Abstract: This invention relates to a clean-up solvent and paint thinner for solvent-borne resins and coatings selected from compositions of Formula (I) wherein R1 is a C1-C10 alkyl group, phenyl or benzyl, R2 is either hydrogen or methyl, R3 is a carbon chain including 4-6 carbon atoms, and n=2-4; of Formula (II) wherein R1 and R4 are, independently, C1-C10 alkyl groups, phenyl or benzyl, R2 is either hydrogen or methyl, R3 is a carbon chain including 0-4 carbon atoms, and n=1-4; and mixtures thereof. The invention also relates to a solvent-borne composition including a solvent-borne polymer and the low and zero VOC composition of the invention; and a method for cleaning or thinning a solvent-borne composition.Type: ApplicationFiled: March 30, 2012Publication date: October 11, 2012Inventors: Felipe A. DONATE, Aleksandr T. GAMBLE, Sarah E. ITTNER, Rebecca J. WACHOWICZ
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Patent number: 8044232Abstract: The present invention relates to a succinic diester polymer which is used in the preparation of water-in-oil macroemulsions. Said polymer, which has an excellent ability to stabilize a water-in-oil macroemulsion, has the formula (I) wherein L is a polyalkenyl group having a number average molecular weight of are poly(alkyleneoxy) chains with a molecular weight of from 500 to 1,200, where each alkyleneoxy group contains 2 or 3 carbon atoms and the number of alkyleneoxy groups being ethyleneoxy groups is at least 50% of the total number of alkyleneoxy groups, and R1 and R2 independently are alkyl groups having of from 1 to 3 carbons atoms. The emulsions of the invention can be used as a diesel fuel, a gasoline fuel, a heating fuel, a dry cleaning liquid, a metalworking fluid or a personal care formulation.Type: GrantFiled: November 24, 2006Date of Patent: October 25, 2011Assignee: Akzo Nobel N.V.Inventors: Albert Van De Berg, Anna Lif, Ingemar Uneback
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Patent number: 7960496Abstract: Disclosed herein is a novel stabilizer for preparing a polymer polyol, which is used to prepare polyurethane foam having improved physical properties. The stabilizer is prepared by allowing maleic anhydride to react with a polyether polyol, having an OH functionality of 3-8 and a molecular weight of 3,000-15,000, and then adding ethylene oxide to the reaction solution. Because the molecular weight and functionality of the stabilizer are increased through aging and dimerization, the stabilizer has a high molecular weight of 5,000-30,000, a high OH functionality of 6-10 and a viscosity of 3,000-15,000 cps/25° C. A polymer polyol derived from the stabilizer has low viscosity compared to those of prior products and contributes to the improvement in the physical properties of the resulting polyurethane foam.Type: GrantFiled: December 14, 2007Date of Patent: June 14, 2011Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Jang Hyun Choi, Seung Moo Huh, Jeon Koo Lee, Jong Yeol Choi
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Publication number: 20110082314Abstract: The present invention relates to a process for preparing polyalkylene glycol di(meth)acrylates by reacting polyalkylene glycol with (meth)acrylic anhydride, wherein the reaction mixture contains at most 0.5% by weight of metal compounds and/or amines, the reaction is carried out in the presence of polymerization inhibitors and the reaction temperature is at least 60° C.Type: ApplicationFiled: May 5, 2009Publication date: April 7, 2011Applicant: EVONIK ROEHM GMBHInventors: Thorben Schuetz, Joachim Knebel, Mario Gomez Andreu
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Publication number: 20100261627Abstract: The present invention is generally directed to diester-based lubricant compositions. The present invention is also directed to methods of making these and other similar lubricant compositions. In some embodiments, the methods for making such diester-based lubricants utilize a biomass precursor and/or low value Fischer-Tropsch (FT) olefins and/or alcohols so as to produce high value diester-based lubricants. In some embodiments, such diester-based lubricants are derived from FT olefins and fatty acids. The fatty acids can be from a bio-based source (i.e., biomass, renewable source) or can be derived from FT alcohols via oxidation.Type: ApplicationFiled: June 25, 2010Publication date: October 14, 2010Applicant: Chevron U.S.A. Inc.Inventors: Stephen Joseph Miller, Saleh A. Elomari
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Patent number: 7659425Abstract: The present invention relates to a process for preparing hydroxyalkyl (meth)acrylates by reacting at least one compound A which contains at least one epoxide group with at least one compound B which contains at least one carboxylic acid group, wherein A and/or B also contains at least one (meth)acrylate group, in the presence of Lewis acid catalysts, each of which contains at least one directly bonded di(cyclo)alkylamino group.Type: GrantFiled: February 16, 2006Date of Patent: February 9, 2010Assignee: Bayer MaterialScience AGInventors: Jan Weikard, Christoph Gürtler
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Patent number: 7045651Abstract: The present invention provides a novel production process for a hydroxyalkyl (meth)acrylate, in which it is possible that: in a batch reaction system, the amount of the hydroxyalkyl (meth)acrylate (which is the objective product) as produced is kept nearly on the same level as conventional and further, at the same time, there is suppressed the side production of the alkylene oxide's diaddition product (dialkylene glycol mono(meth)acrylate) that lowers the purity of the product to thus give a bad influence upon its quality.Type: GrantFiled: May 12, 2003Date of Patent: May 16, 2006Assignee: Nippon Shokubai Co., Ltd.Inventors: Tokumasa Ishida, Masahiro Uemura
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Patent number: 6855844Abstract: Disclosed are polyester-ether polyols and their use in urethane prepolymers, urethane foams and non-foam urethane coatings, adhesives, sealants and/or elastomers. Methods for producing such polyester-ether polyols using double metal cyanide catalysts are disclosed, along with methods for producing urethane prepolymers. The polyester-ether polyols of the instant invention are preferably the reaction product of phthalic anhydride, diethylene glycol, and propylene oxide. These polyester-ether polyols are useful as either the primary polyol in urethane compositions or in combination with conventional auxiliary polyester- and/or polyether-based polyols. The polyester-ether polyols impart greatly improved solubility and compatibility to mixtures of either polyether and/or polyester polyols. The polyester-ether polyols of the instant invention are desirably of lower viscosity than their precursor intermediate polyester polyols and are generally soluble in either polyester- and/or polyether-based polyols.Type: GrantFiled: October 25, 2000Date of Patent: February 15, 2005Assignee: Stepan CompanyInventors: Eric J. Geiger, Douglas K. Hillshaffer
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Patent number: 6838575Abstract: The invention relates to a process for the preparation, in a single step, of enones by an aldol condensation of a ketone, such as a gem-dimethyl cyclohexylethanone or gemdimethyl cyclohexenylethanone derivative, with an aldehyde in the presence of a novel catalytic system and a co-ingredient, such as a carboxylic acid anhydride or an anhydrous salt, and without the pre-formation of an enolate. The catalytic system is a metal complex, such as a [(Cl)n(alkoxy)4-nTi] or [(Cl)n(alkoxy)4-nZr] complex where n is 1 to 3.Type: GrantFiled: October 17, 2003Date of Patent: January 4, 2005Assignee: Firmenich SAInventor: Denis Jacoby
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Patent number: 6765116Abstract: A process to prepare an improved fluid rare earth phosphate catalyst composition useful in preparing alkylene oxide adducts of organic compounds having active hydrogen atoms is provided. The catalyst is prepared by dissolving a rare earth salt in a C9-C30 active hydrogen containing organic compound and then adding phosphoric acid to the organic compound rare earth mixture.Type: GrantFiled: August 23, 2002Date of Patent: July 20, 2004Assignee: Shell Oil CompanyInventor: Charles Lee Edwards
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Patent number: 6753402Abstract: Polyester-polyether block copolymers can be prepared by catalytic addition of alkylene oxides onto H-functional initiator substances, using polyester alcohols as H-functional initiator substances and multimetal cyanide compounds as catalysts.Type: GrantFiled: April 10, 2002Date of Patent: June 22, 2004Assignee: BASF AktiengesellschaftInventors: Stephan Bauer, Georg Heinrich Grosch, Gerlinde Tischer, Kathrin Harre, Eva Baum, Thomas Ostrowski, Reinhard Lorenz, Regina Pretzsch, Michael Pcolinski, Stefan Dinsch, Inge Rotermund
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Publication number: 20040096507Abstract: The present invention relates to novel hexa-arm polyethylene glycol (6-arm PEG) and its derivatives. The core of 6-arm PEG derivatives is sorbitol and the end groups can be derivatized into many different reactive functionalities that are useful in conjugating with many different targets. The present invention also provides a biodegradable polymeric hydrogel-forming composition comprising the 6-arm PEG and its derivatives, and methods of using such 6-arm PEG derivatives as surgical or biological implants or sealants.Type: ApplicationFiled: December 23, 2002Publication date: May 20, 2004Applicant: SunBio Inc.Inventors: Nho Kwang, Hyun Chang-min, Lee Jung-Hun, Kim In-Kyung, Pak Young-Kyoung
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Patent number: 6723872Abstract: The present invention provides: a process in which, when a hydroxyalkyl ester is produced by carrying out a reaction between a carboxylic acid and an alkylene oxide in the presence of a catalyst, the contamination of the hydroxyalkyl ester with water can be inhibited to the maximum limit without washing the inside of a production apparatus together with the raw carboxylic acid or the hydroxyalkyl ester as an aimed product, or without carrying out azeotropic distillation with water and an azeotropic solvent. The process comprises a washing step and thereafter a drying step in the interval of from the stop of a production of the hydroxyalkyl ester till the restart of this production, wherein the washing step is a step of washing the inside of a production apparatus with water and/or an aqueous basic solution, and wherein the drying step is a step of drying under reduced pressure and/or hot-air-drying the inside of the production apparatus.Type: GrantFiled: January 30, 2002Date of Patent: April 20, 2004Assignee: Nippon Shokubai Co., Ltd.Inventors: Yasuhiro Shingai, Kouji Deguchi
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Patent number: 6649786Abstract: This invention provides a process to produce a hydroxyl group-containing ester-forming addition reaction product having an acid value of 20 mgKOH/g or less, which process is characterized in that 2,2-dimethylolalkanoic acid having 6 to 8 carbon atoms is melted, and is then mixed with alkanoic acid monoglycidylester having 8 to 24 carbon atoms so that an ester-forming addition reaction may occur. Thus obtained reaction product contains almost no undesirable high-molecular components, is quite excellent in reactivity and compatibility with a curing agent, and is useful for the manufacture of high-solids paint etc.Type: GrantFiled: August 21, 2002Date of Patent: November 18, 2003Assignee: Kansai Paint Co., Ltd.Inventor: Hisashi Isaka
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Patent number: 6541656Abstract: Economical and efficient processes for producing an &agr;, &bgr;-unsaturated carboxylic acid heterocycle-inserted ester and an &agr;,&bgr;-unsaturated carboxylic acid polyheteroalkylene ester as well as a catalyst suited for use in economically and efficiently producing an &agr;,&bgr;-unsaturated carboxylic acid ester are provided. The invention provides (1) a process for producing an &agr;,&bgr;-unsaturated carboxylic acid ester which comprises reacting an &agr;,&bgr;-unsaturated carboxylic acid ester with a heterocyclic compound, (2) a process for producing an &agr;,&bgr;-unsaturated carboxylic acid ester which comprises reacting an &agr;,&bgr;-unsaturated carboxylic acid with a heterocyclic compound in the presence of a polymerization inhibitor and a metal oxide catalyst, and (3) a catalyst for the production of an &agr;,&bgr;-unsaturated carboxylic acid ester comprising a metal oxide.Type: GrantFiled: February 8, 2001Date of Patent: April 1, 2003Assignee: Nippon Shokubai Company, Ltd.Inventors: Keiji Yurugi, Takafumi Kubo
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Publication number: 20030060571Abstract: Monofunctional polyfluorooxetane oligomers and polymers are prepared by the cationic polymerization of fluorooxetane monomers with a monoalcohol. The fluorooxetane oligomers or polymers can be copolymerized with generally cyclic ethers. Alternatively, the polyfluorooxetane oligomer or polymer having a single hydroxyl end group can be functionalized with a variety of compounds so as to yield a functional end group such as an acrylate, a methacrylate, an allylic, an amine, etc., with the functionalized oligomer or polymer being suitable for use in radiation curable or thermal curable coating compositions. These functionalized polymers can be copolymerized and cured to provide improvements in wetting and surface properties that have previously been provided by migratory chemicals such as waxes and oils.Type: ApplicationFiled: March 28, 2002Publication date: March 27, 2003Applicant: OMNOVA Solutions Inc.Inventors: Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson, Robert E. Medsker
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Patent number: 6498268Abstract: A method of producing alkylene glycol esters of unbranched aliphatic dicarboxylic acids with limited homolog distribution, and the use of the esters produced as monomer structural units for producing polymers are disclosed.Type: GrantFiled: May 19, 2000Date of Patent: December 24, 2002Assignee: Cognis Deutschland GmbHInventor: Hans-Christian Raths
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Publication number: 20020156200Abstract: Monofunctional polyfluorooxetane oligomers and polymers Zare prepared by the cationic polymerization of fluorooxetane monomers with a monoalcohol. The fluorooxetane oligomers or polymers can be copolymerized with generally cyclic ethers. Alternatively, the poly-fluorooxetane oligomer or polymer having a single hydroxyl end group can be functionalized with a variety of compounds so as to yield a functional end group such as an acrylate, a methacrylate, an allylic, an amine, etc., with the functionalized oligomer or polymer being suitable for use in radiation curable or thermal curable coating compositions. These functionalized polymers can be copolymerized and cured to provide improvements in wetting and surface properties that have previously been provided by migratory chemicals such as waxes and oils.Type: ApplicationFiled: March 28, 2002Publication date: October 24, 2002Applicant: OMNOVA Solutions Inc.Inventors: Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson, Robert E. Medsker
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Publication number: 20020143112Abstract: Monofunctional polyfluorooxetane oligomers and polymers are prepared by the cationic polymerization of fluorooxetane monomers with a monoalcohol. The fluorooxetane oligomers or polymers can be copolymerized with generally cyclic ethers. Alternatively, the polyfluorooxetane oligomer or polymer having a single hydroxyl end group can be functionalized with a variety of compounds so as to yield a functional end group such as an acrylate, a methacrylate, an allylic, an amine, etc., with the functionalized oligomer or polymer being suitable for use in radiation curable or thermal curable coating compositions. These functionalized polymers can be copolymerized and cured to provide improvements in wetting and surface properties that have previously been provided by migratory chemicals such as waxes and oils.Type: ApplicationFiled: March 28, 2002Publication date: October 3, 2002Applicant: OMNOVA Solutions Inc.Inventors: Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson, Robert E. Medsker
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Publication number: 20020137853Abstract: Monofunctional polyfluorooxetane oligomers and polymers are prepared by the cationic polymerization of fluorooxetane monomers with a monoalcohol. The fluorooxetane oligomers or polymers can be copolymerized with generally cyclic ethers. Alternatively, the polyfluorooxetane oligomer or polymer having a single hydroxyl end group can be functionalized with a variety of compounds so as to yield a functional end group such as an acrylate, a methacrylate, an allylic, an amine, etc., with the functionalized oligomer or polymer being suitable for use in radiation curable or thermal curable coating compositions. These functionalized polymers can be copolymerized and cured to provide improvements in wetting and surface properties that have previously been provided by migratory chemicals such as waxes and oils.Type: ApplicationFiled: March 27, 2002Publication date: September 26, 2002Applicant: OMNOVA Solutions Inc.Inventors: Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson, Robert E. Medsker
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Patent number: 6388041Abstract: Disclosed are polyoxyethylene derivatives having different functional groups at both ends of the molecule represented by the following formula (I) and a process for producing the derivatives by anionic living polymerization. The present invention provides polymers which are especially suitable for use as medical materials. wherein A′ and B′ are organosilyl type amino-protecting groups, R is a hydrogen atom or a C1-6 alkyl group, and Y is a hydrogen atom, an alkali metal or a certain functional group.Type: GrantFiled: November 7, 2000Date of Patent: May 14, 2002Assignee: Nano Carrier Co LtdInventors: Kazunori Kataoka, Masao Kato, Yukio Nagasaki, Takahisa Hayashida, Michihiro Iijima, Teruo Okano
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Patent number: 6277497Abstract: A high solids coating composition comprising a branched hydroxy-functional polyester oligomer and a curing agent; and the oligomer itself containing at least 20% by weight of the binder of at least one of the following tertiary acid ester end groups: where R1, R2 and R3 are independently selected from CH3 and CH2OH; the composition being suitable as an automobile clearcoat or pigmented topcoat.Type: GrantFiled: January 14, 2000Date of Patent: August 21, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Armand Aerts, Anne Demarre, Jozef Huybrechts, G. Todd Palmer
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Patent number: 5990264Abstract: Poly(ester-ethers) are produced by the copolymerization of tetrahydrofurans and cyclic carboxylic anhydrides using selected metal perfluoroalkylsulfonates and related compounds as catalysts. The resulting copolymers are useful as intermediates for monomers for use in other polymerizations.Type: GrantFiled: July 31, 1996Date of Patent: November 23, 1999Assignee: E. I. du Pont de Nemours and CompanyInventor: Neville Everton Drysdale
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Patent number: 5952452Abstract: A high solids coating composition comprising a branched hydroxy-functional polyester oligomer and a curing agent; and the oligomer itself containing at least 20% by weight of the binder of at least one of the following tertiary acid ester end groups: ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are independently selected from CH.sub.3 and CH.sub.2 OH; the composition being suitable as an automobile clearcoat or pigmented topcoat.Type: GrantFiled: July 16, 1997Date of Patent: September 14, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Armand Aerts, Anne DeMarre, Jozef Huybrechts, G. Todd Palmer
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Patent number: 5750770Abstract: Hydroxy functional, unsaturated diesters are disclosed that comprise the esterification reaction products of unsaturated anhydrides with secondary alcohols to form monoesters, followed by oxyalkylation of the monoester with epoxy compounds, whereby a diester is formed with hydroxy functionality. Use of secondary alcohol yields monoesters less prone to disproportionation. The unsaturated diesters may be copolymerized with vinyl monomers to form hydroxy functional copolymers useful in coating applications, wherein they may be included in compositions along with a curing agent that is reactive with hydroxy groups.Type: GrantFiled: October 10, 1995Date of Patent: May 12, 1998Assignee: PPG Industries, Inc.Inventors: Edward E. McEntire, Lyle L. Foringer
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Patent number: 5688750Abstract: A base fluid for metal working fluids comprises a stoichiometrically neutral salt of the partial esterification product having an acid number of 10-120, preferably 20-100 of polymerized fatty acids and a monohydric alkoxylated alcohol, selected from (a) straight or branched chain saturated monohydric C.sub.1 -C.sub.24 alcohols, alkoxylated with 2-25 moles of C.sub.2 -C.sub.5 alkylene oxide, (b) alkoxy poly(alkylene) glycol etherified with C.sub.1 -C.sub.4 aliphatic monohydric alcohol and which is alkoxylated with 2-25 moles of C.sub.2 -C.sub.5 alkylene oxide, (c) an aliphatic, straight or branched chain, saturated or unsaturated C.sub.1 -C.sub.24 monohydric alcohol, and mixtures thereof, which partial ester is converted into a stoichiometrically neutral salt by neutralizing it by ammonium hydroxide, or an alkali metal hydroxide or an alkyl amine or an alkanol amine. Also the novel stoichiometrically neutral alkali metal and alkanol amine salts of the partial esters have been claimed.Type: GrantFiled: December 1, 1995Date of Patent: November 18, 1997Assignee: Unichema Chemie B. V.Inventors: Nigel Andrew John Cooban, Hendrik Leendert Rieffe
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Patent number: 5684179Abstract: An improved method for recovering purified diesters of polytetramethylene ethers involving the polymerization of tetrahydrofuran (THF) optionally with one or more comonomers (e.g., 3-methyl THF, ethylene oxide, propylene oxide, or the like) utilizing a solid acid catalyst (e.g., Nafion.RTM.) and a carboxylic acid with carboxylic acid anhydride (e.g., acetic acid with acetic anhydride) as molecular weight control agents wherein after polymerization product recovery involves bulk flashing of unreacted THF and stripping of remaining THF, carboxylic acid and carboxylic acid anhydride (e.g., acetic acid and acetic anhydride) by use of superheated THF. Such a process is useful in producing high purity commercial grade PTMEA that advantageously avoids problems associated with the presence of high boilers when converting to PTMEG.Type: GrantFiled: December 14, 1995Date of Patent: November 4, 1997Assignee: E. I. du Pont de Nemours and CompanyInventor: Suriyanarayan Dorai
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Patent number: 5672662Abstract: Active esters of PEG acids and related polymers are provided that have a single propionic or butanoic acid moiety and no other ester linkages. These polymer acids have a half life in water of from about 10 to 25 minutes. For example, alpha-methoxy, omega-propionic acid succinimidyl ester of PEG ("methoxy-PEG-SPA") has a nearly ideal reactivity with amino groups on proteins and other biologically active substances. The half life of methoxy-PEG-SPA is about 16.5 minutes in water. The invention also provides conjugates with proteins, enzymes, polypeptides, drugs, dyes, nucleosides, oligonucleotides, lipids, phospholipids, liposomes, and surfaces of solid materials that are compatible with living organisms, tissue, or fluid.Type: GrantFiled: October 2, 1995Date of Patent: September 30, 1997Assignee: Shearwater Polymers, Inc.Inventors: J. Milton Harris, Antoni Kozlowski
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Patent number: 5506309Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.Type: GrantFiled: June 6, 1995Date of Patent: April 9, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhulke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5483008Abstract: The present invention relates to a bifunctional polyether having groups different from each other at both ends, with a polymerization degree of 5 to 10000 and consisting of repeating units each represented by the following formula (I): ##STR1## (wherein R.sub.1, represents a hydrogen atom, halogen atom, or a lower alkyl group optionally substituted by a halogen atom, and R.sub.1 in each repeating unit may be the same or different), as well as to a process for the preparation thereof and a polymerization initiator therefor. The process of production and polymerization initiator of the present invention enable 100% introduction of a primary amino group into one of the ends of polyether.Type: GrantFiled: February 5, 1993Date of Patent: January 9, 1996Assignee: Research Development Corporation of JapanInventors: Yasuhisa Sakurai, Teruo Okano, Masayuki Yokoyama, Kazunori Kataoka, Yukio Nagasaki, Nobuyuki Ohsako, Masao Kato
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Patent number: 5463020Abstract: Polytetrahydrofuran or C.sub.2 -C.sub.10 -alkylene oxide/tetrahydrofuran copolymers having a molecular weight of from 250 to 20,000 Dalton are prepared by the cationic polymerization of tetrahydrofuran or tetrahydrofuran and C.sub.2 -C.sub.10 -alkylene oxides in the prsence of a promoter by a process in which the catalyst used is a mixture of one or more C.sub.2 -C.sub.6 -di- or tricarboxylic acids with boric acid.Type: GrantFiled: June 30, 1994Date of Patent: October 31, 1995Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Michael Huellmann, Christof Palm, Wolfgang Franzischka
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Patent number: 5386045Abstract: A process for producing alkoxylated mono-, di-, and tri-esters in which a starting material ester and an alkylene oxide are reacted in the presence of selected calcium based catalysts.Type: GrantFiled: August 5, 1992Date of Patent: January 31, 1995Assignee: Vista Chemical CompanyInventors: Upali Weerasooriya, Donald T. Robertson, John Lin, Bruce E. Leach, Cynthia L. Aeschbacher, Tonyette S. Sandoval
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Patent number: 5370810Abstract: A material useful as a dispersant additive in oleaginous compositions selected from fuels and lubricating oils comprising the reaction products of:(i) at least one intermediate adduct comprised of the reaction products of(a) at least one polyepoxide, and(b) at least one member selected from the group consisting of polyamines, polyols, and amino alcohols; and(ii) at least one of (a) hydrocarbyl substituted C.sub.3 -C.sub.10 monocarboxylic or C.sub.4 -C.sub.10 dicarboxylic acid producing material; (b) an aldehyde and a hydrocarbyl substituted hydroxy aromatic compound; or (c) an aldehyde and the reaction product of a hydrocarbyl substituted C.sub.3 -C.sub.10 monocarboxylic or C.sub.4 -C.sub.10 dicarboxylic acid or anhydride and an amine substituted hydroxy aromatic compound.Also included is a process for preparing said material and an oleaginous composition containing said material.Type: GrantFiled: January 5, 1993Date of Patent: December 6, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Jacob Emert, Antonio Gutierrez, Robert D. Lundberg
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Patent number: 5210325Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalyst which comprises one or more compounds comprising a rare earth element and phosphorus supported on an inert porous support. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 10, 1992Date of Patent: May 11, 1993Assignee: Shell Oil CompanyInventors: Richard A. Kemp, Paul R. Weider
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Patent number: 5177249Abstract: The present invention relates to compounds comprising ester groups having at least three ester functions, to processes for the production thereof, and to the use of the products.Compounds having at least three functional ester groups of the general formula: ##STR1## are described, wherein the abbreviations have the following meanings: X=--CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--,Y=bivalent, saturated aliphatic hydrocarbon residue optionally substituted,Z=optionally substituted acyl residue --CO--RR.sub.1 =the residue of an alcohol, or a group from an alkylene-oxide-adduct taking the alcohol function in the ester grouping.n=1 to 3 andm=1 to 3.Type: GrantFiled: November 20, 1990Date of Patent: January 5, 1993Assignee: Chemische Fabrik Stockhausen GmbHInventor: Reinmar Peppmoller
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Patent number: 5130470Abstract: A process for polymerizing tetrahydrofuran using a fluorinated resin containing sulfonic acid groups a trifluoromethane sulfonic acid as catalyst and a mixture of maleic acid and maleic anhydride as weight control agent. The product has the formula ##STR1## which can be hydrogenated to produce polytetramethylene ether glycol. The preferred molecular weight range of the polytetramethylene ether glycol is 600 to 4,000.Type: GrantFiled: March 27, 1991Date of Patent: July 14, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Suriyanarayan Dorai, Willard L. Quon, Kirk M. Schall, Gary A. Hida
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Patent number: 5118870Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of a xerogel comprising one or more compounds comprising a rare earth element and phorphorus. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: April 23, 1990Date of Patent: June 2, 1992Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5057628Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more compounds of one or more of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventors: Charles L. Edwards, Richard A. Kemp
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Patent number: 5057627Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the phosphate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5026923Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the borate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: May 29, 1990Date of Patent: June 25, 1991Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5015697Abstract: A process is disclosed for preparing a composition comprising a polybutyl ketone and a hydroxyester of an epoxidized polybutene wherein the epoxide groups of said epoxidized polybutene are at least 70% trisubstituted. Acid compounds are reacted with epoxidized polybutenes to obtain compositions of increased reactivity as compared with polybutyl ketone compounds. These compositions are useful as chemical intermediates to modify such materials as polyesters and polyurethenes, for applications such as coatings, foams, and sealants.Type: GrantFiled: January 31, 1989Date of Patent: May 14, 1991Assignee: Amoco CorporationInventor: Wayne T. Riddick
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Patent number: 4970333Abstract: The production of esters via the reaction of an epoxide with a carboxylic acid hasbeen shown to give improved activity when a strong base macroporous anion exchange resin having an acrylic backbone is used in place of a styrene-divinylbenzene based anion exchange resin having an equivalent exchange capacity. Excellent results are obtained when acrylic acid and propylene oxide are reacted together in the presence of strong base macroporous anion exchange resins which have an acrylic backbone.Type: GrantFiled: October 29, 1987Date of Patent: November 13, 1990Assignee: The Dow Chemical CompanyInventors: James A. Rabon, Jr., William C. Pike, Clinton J. Boriack
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Patent number: 4962237Abstract: A catalytic process for polymerizing epoxides using active hydrogen initiators forming polyols having low unsaturation levels and high primary hydroxyl levels. The catalysts useful in this process are prepared from catalyst precursors exemplified by hydrotalcite. This process is more reactive with less acidic active hydrogen initiators. The polyols can be used in urethanes without removal of the catalyst.Type: GrantFiled: January 2, 1990Date of Patent: October 9, 1990Assignee: The Dow Chemical CompanyInventor: David E. Laycock
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Patent number: 4960952Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more lanthanum compounds comprising silicate, metasilicate and mixtures thereof. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 31, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 4814515Abstract: A method of manufacturing a modified polyhydroxy compound, which is characterized in that a polyhydroxy compound is heated for 30 minutes or more at a temperature ranging from 150.degree. to 250.degree. C. under stirring and in the presence of tin, tin compounds such as tin halogenide, tin hydroxide and tin oxide. The polyhydroxy compound modified by this method is effective in improving the foamability and mechanical strength of urethane foam, when it is used as a raw material in the manufacture of urethane foam.Type: GrantFiled: May 18, 1987Date of Patent: March 21, 1989Assignee: Human Industry CorporationInventors: Sadao Kumasaka, Satomi Tada, Hirokazu Wakabayashi