Heterocyclic Compound Contains A 1,2-epoxy Ring Patents (Class 528/250)
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Patent number: 11326051Abstract: It has been desired to develop a method for producing an oxymethylene polymer, by which an oxymethylene polymer having a high polymerization degree can be produced with high efficiency while suppressing increase in the amount of generation of an odor. Further, it has been desired to develop an oxymethylene polymer resin composition, wherein generation of an odor at the time of molding or after molded to obtain a molded body is suppressed. The present invention provides a method for producing an oxymethylene polymer, wherein the oxymethylene polymer is produced by polymerizing a cyclic oligomer of formaldehyde, and wherein a boron trifluoride compound and an aryl fluoride boron compound are used as polymerization catalysts. The present invention also provides an oxymethylene polymer resin composition containing an oxymethylene polymer and a derivative of an aryl fluoride boron compound.Type: GrantFiled: June 10, 2020Date of Patent: May 10, 2022Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Takuya Okada, Daisuke Sunaga
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Patent number: 8008422Abstract: In general, the invention provides curable resin compositions that may be used to rebuild insulation and/or to provide environmental protection for cable splices, potted articles, and the like. The curable resin compositions can be curable at room temperature. The components used to form and cure the resin compositions may be provided in two or more parts. In specific embodiments, the invention provides curable resin compositions having anhydride, polyol, epoxy, and urethane components.Type: GrantFiled: July 11, 2008Date of Patent: August 30, 2011Assignee: 3M Innovative Properties CompanyInventor: Jeanine I. Zeller-Pendrey
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Patent number: 7851585Abstract: The invention relates to polyacetal compositions comprising a mixture of (i) a polyacetal resin, (ii) p-aramid particles and (III) a vinyl-terminated dimethyl siloxane polymer. These compositions are useful in preparing molded articles exhibiting a good balance between high self-lubricating properties and wear resistance, and especially useful in articles that are in motion with respect to other parts they are in contact with.Type: GrantFiled: October 16, 2008Date of Patent: December 14, 2010Assignee: E. I. du Pont de Nemours and CompanyInventors: Anne-Laure Brison, Andreas Renken
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Patent number: 7795357Abstract: Multiblock copolymers are described and contain the structural unit of formula I -A-O—R1—O—CO—(R2—CO—)m—X-D-X—(CO—R2)m—CO—X—??(I), where A is a radical derived from a homo- or copolyoxymethylene, R1 is an alkylene radical-having at least two carbon atoms or a cycloalkylene radical, R2 is a direct carbon-carbon bond, or an alkylene, cycloalkylene, arylene, or aralkylene radical, X is selected from —O—, —S—, or —NH—, D is a divalent radical B which is a radical of a hydroxy-terminated, mercaptan-terminated, or amino-terminated polymer which derives from polyalkylene glycols, polyvinyl ethers, polyvinyl ether-alkene copolymers, polyvinyl esters, polyvinyl ester-alkene copolymers, polyvinyl alcohols, polyvinyl alcohol-alkene copolymers, polyvinylaromatics, polyacrylates, polymethacrylates, polyacetals, polycarbonates, polyesters, polyamides, polyimines, polyetherester elastomers, polyetheramide elastomers, polyalkadienes, polyurethanes, polyureas, polysiloxanes, or a triblock copolymer radical -PAO-B-PAO-, whType: GrantFiled: September 3, 2004Date of Patent: September 14, 2010Assignee: Ticona GmbHInventors: Dirk Zierer, Klaus Kurz, Jens Schiebisch, Karl-Friedrich Mück, Holger Schmalz
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Publication number: 20100010190Abstract: In general, the invention provides curable resin compositions that may be used to rebuild insulation and/or to provide environmental protection for cable splices, potted articles, and the like. The curable resin compositions can be curable at room temperature. The components used to form and cure the resin compositions may be provided in two or more parts. In specific embodiments, the invention provides curable resin compositions having anhydride, polyol, epoxy, and urethane components.Type: ApplicationFiled: July 11, 2008Publication date: January 14, 2010Inventor: Jeanine I. Zeller-Pendrey
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Publication number: 20090264615Abstract: A process and an apparatus for the preparation of oxymethylene polymers is described. The process encompasses the polymerization of a monomer that forms oxymethylene groups, if appropriate in the presence of a cyclic acetal, together with an acetal of formaldehyde and with an initiator for cationic polymerization, preferably in a gas-tight kneader or extruder. The temperature profile of the polymerization here is designed in such a way that the polymerization mixture, which is initially heterogeneous by virtue of precipitating polymer, is converted to a homogeneous phase at the end of the polymerization. The homogeneous phase in which the polymer is present in liquid form is stabilized via addition of deactivators. After removal of volatile constituents, oxymethylene polymers are obtained with high thermal stability and with good mechanical properties.Type: ApplicationFiled: April 14, 2009Publication date: October 22, 2009Inventors: Michael Haubs, Eberhard Mann, Jurgen Lingnau
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Patent number: 7348128Abstract: A photosensitive resin which exhibits excellent storage stability, affinity, miscibility, or solubility with respect to a variety of compounds, and high sensitivity can be solidified even under hydrous conditions as well as exhibiting high cure-related sensitivity and high flexibility and being uniformly solidified even under highly hydrous conditions, a photosensitive resin composition containing the resin, and a novel compound. The photosensitive resin is a saponified poly(vinyl acetate)-based photosensitive resin having a structural unit represented by formula (1): (wherein R1 represents H or Me; R2 represents a linear or branched C2-C10 alkylene group; n is an integer of 1 to 3; X represents m is an integer of 0 to 6; and Y represents an aromatic ring or a single bond).Type: GrantFiled: November 13, 2003Date of Patent: March 25, 2008Assignee: Toyo Gosei Co., Ltd.Inventors: Seigo Yamada, Masahiro Takano, Mitsuharu Miyazaki, Shin Utsunomiya
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Patent number: 7259213Abstract: This invention relates to epoxy resins containing indole as structural unit, indole resins and resin compositions containing said epoxy resins and indole resins useful for applications such as laminating, molding, casting and adhesion on account of their excellent fire retardance, adhesiveness, moisture resistance and heat resistance. The indole resins of this invention and the epoxy resins obtained therefrom are represented by the following general formulas I and II wherein R1 is H, alkyl or the like, X is a crosslinking group represented by —C(R2R3)— or C(R4R5)—Ar—C(R4R5)— (wherein R2-R5 are H, alkyl or the like and Ar is a benzene or biphenyl ring), G is glycidyl group and n is an integer of 1-20.Type: GrantFiled: February 10, 2003Date of Patent: August 21, 2007Assignee: Nippon Steel Chemical Co., Ltd.Inventors: Masashi Kaji, Hisashi Yamada
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Patent number: 7074876Abstract: Disclosed herein is a blocked mercaptosilane selected from the group consisting of [[(ROC(?O))p—(G)j]k—Y—S]r—G—(SiX3)s; and??(1) [(X3Si)q—G]a—[Y—[S—G—SiX3]b]c??(2) wherein Y is a polyvalent species (Q)zA(?E) selected from the group consisting of —C(?NR)—; —SC(?NR)—; —SC(?O)—; —OC(?O)—; —S(?O)—; —S(?O)2—; —OS(?O)2—; (—NR)S(?O)2—; —SS(?O)—; —OS(?O)—; (—NR)S(?O)—; —SS(?O)2—; (—S)2P(?O)—; —(—S)P(?O)—; —P(?O)(—)2; (—S)2P(?S)—; —(—S)P(?S)—; —P(?S)(—)2; (—NR)2P(?O)—; (—NR)(—S)P(?O)—; (—O)(—NR)P(?O)—; (—O)(—S)P(?O)—; (—O)2P(?O)—; —(—O)P(?O)—; —(—NR)P(?O)—; (—NR)2P(?S)—; (—NR)(—S)P(?S)—; (—O)(—NR)P(?S)—; (—O)(—S)P(?S)—; (—O)2P(?S)—; —(—O)P(?S)—; and —(—NR)P(?S)—; wherein the atom A attached to unsaturated heteroatom E is attached to the sulfur which in turn is linked via a group G to the silicon atom; each R is chosen independently from hydrogen, straight, cyclic, or branched alkyl that may or may not contain unsaturation, alkenyl groups, aryl groups, and aralkyl groups, with each R containing from 1 to 18 cType: GrantFiled: November 9, 2001Date of Patent: July 11, 2006Assignee: General Electric CompanyInventors: Richard W. Cruse, Robert J. Pickwell, Keith J. Weller, Eric R. Pohl
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Patent number: 7030207Abstract: The invention is to provide a polymer, having a high affinity to water, is liquid in spite of being a polymer, simultaneously possesses also a thermal stability and is suitably used as a heating medium or a lubricant. It is the polyacetal (co)polymer, being liquid at room temperature, prepared by copolymerizing (A) 75 to 100 mol % of 1,3-dioxolane and (B) 25 to 0 mol % of trioxane and having the total amount of terminal groups of 15 to 300 mmol/kg and an amount of a hemiformal terminal group of 80 mmol/kg or less.Type: GrantFiled: July 23, 2002Date of Patent: April 18, 2006Assignee: Polyplastics Co., Ltd.Inventors: Yoshihisa Tajima, Hiroaki Nakao, Kuniaki Kawaguchi
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Patent number: 7001959Abstract: Copolymers are described containing blocks of the structural repeat units of the formula I and blocks containing structural units of the formula II [—O—CH2—]x,??(I) [—O—R1—],??(II) where R1 is a divalent radical derived from a hydroxy-terminated aliphatic or cycloaliphatic oligomer or polymer which, where appropriate, has ether groups and/or carbonyloxy groups in the chain, and x is a whole number, at least 10. The copolymers may be used for producing moldings.Type: GrantFiled: November 3, 2003Date of Patent: February 21, 2006Assignee: Ticona GmbHInventors: Karl-Friedrich Mück, Klaus Kurz, Michael Hoffmockel
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Publication number: 20040034188Abstract: The present invention provides novel monofunctional polyethylene glycol aldehydes for the pegylation of therapeutically active proteins. The pegylated protein conjugates that are produced, retain a substantial portion of their therapeutic activity and are less immunogenic than the protein from which the conjugate is derived. New syntheses for preparing such aldehydes are described.Type: ApplicationFiled: May 7, 2003Publication date: February 19, 2004Inventors: Perry Rosen, Kwang Nho
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Patent number: 6670041Abstract: Water-dilutable binders which are self-crosslinking at room temperature, comprising reaction products ABF with epoxy-amine adducts A and formaldehyde resin formers B selected from phenols B1, (substituted) ureas B2, melamine B3, guanamines B4, and mixtures of said resin formers, with formaldehyde F or compounds which give off formaldehyde under the reaction conditions, may be formulated, following at least partial neutralization, to give aqueous coating materials which give coatings affording outstanding corrosion protection.Type: GrantFiled: November 2, 2001Date of Patent: December 30, 2003Assignee: Solutia Austria GmbHInventors: Willibald Paar, Roland Feola, Johann Gmoser, Michael Gobec
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Patent number: 6646016Abstract: Resins useful in methods of breaking oil-water emulsions. The resins obtained by reacting a compound of formula 1 with an aldehyde and alkoxylating, in any order: wherein X is —NHR1; —COOH; or —CONHR2; and is ortho—, meta— or para— to X and is a radical of —O—R3; —C(O)R4; —OC(O)R5; —NR6R7; wherein R1-R7 values are defined herein.Type: GrantFiled: May 14, 2002Date of Patent: November 11, 2003Assignee: Clariant GmbHInventors: Frank Holtrup, Elisabeth Wasmund, Wolfram Baumgärtner, Michael Feustel
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Patent number: 6617416Abstract: A polyoxymethylene copolymer which is a polyoxymethylene copolymer obtained by copolymerizing trioxane and 8 to 20 mol, per 100 mol of the trioxane, of 1,3-dioxolane and which (i) has a crystallization time period of 10 to 2,000 seconds at 143° C., (ii) withstands 30 to 1,000 cycles of a bending durability test and (iii) has residence heat stability for 40 minutes or more, and a molded article formed of the copolymer. According to the present invention, there can be provided a polyoxymethylene copolymer excellent in bending durability and heat stability and excellent in moldability, and a molded article formed thereof.Type: GrantFiled: October 15, 2002Date of Patent: September 9, 2003Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takahiro Nakamura, Masanori Furukawa, Akira Okamura, Daigo Nakaya, Isamu Masumoto
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Patent number: 6576714Abstract: The present invention provides a production process for a terminal-end-stabilized glyoxylic acid (salt)-based polymer, which process enables to reduce the amount of the polymerization solvent, as recovered or removed after the end of the polymerization (before the start of the hydrolysis) or after the end of the hydrolysis, without lowering the production efficiency. The production process for a terminal-end-stabilized glyoxylic acid (salt)-based polymer comprises the step of polymerizing a monomer component including a glyoxylic acid ester in order to produce the terminal-end-stabilized glyoxylic acid (salt)-based polymer, wherein a terminal end stabilizer is used as a reaction medium of the polymerization.Type: GrantFiled: February 22, 2001Date of Patent: June 10, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Takuya Saeki, Akihiko Kanzaki, Junichi Nakamura, Yoshikazu Fujii, Shigeru Yamaguchi
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Patent number: 6506838Abstract: Modified oxymethylene polymers comprising a linear polymer of oxymethylene repeat units, blocked at one end by at least one terminal group selected from the group consisting of an alkylene oxide as an adduct to alcohol and an alkylene oxide as an adduct to carboxylic acid, the linear polymer excluding the terminal group having a number average molecular weight of 10,000-500,000 and the modified oxymethylene polymer having a molecular weight distribution (Mw/Mn) of not more than 2.5, obtained by anionic polymerization of formaldehyde and the alkylene oxide as an adduct to alcohol and/or carboxylic acid. The present modified oxymethylene polymers can give moldings with improved repeated impact resistance at the welded parts and controlled smell generation, and improved sliding characteristics, wherein the sliding characteristics are further improved upon combination with an olefinic polymer.Type: GrantFiled: October 25, 2000Date of Patent: January 14, 2003Assignee: Asahi Kasei Kabushiki KaishaInventor: Toshiharu Seyama
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Publication number: 20020091195Abstract: Water-dilutable, cationically stabilized epoxy resins ZYX are obtained by reacting, in the first stage, aromatic or aliphatic epoxide compounds Z with aliphatic amines Y to form epoxy-amine adducts ZY which are neutralized and then in aqueous dispersion are reacted in a second stage with a further epoxy resin X. The resins ZYX may be formulated without additional curatives to give aqueous coating materials which exhibit a good corrosion protection effect.Type: ApplicationFiled: November 2, 2001Publication date: July 11, 2002Inventors: Willibald Paar, Roland Feola, Johann Gmoser, Maximilian Friedl
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Patent number: 6365704Abstract: To provide a resin material in which various properties of a polyacetal resin such as excellent appearance, slidability and thermal stability are maintained and a rigidity is improved as well. That is, a polyacetal copolymer which is prepared by a copolymerization of 100 parts by weight of trioxane (A), 0.0005 to 2 parts by weight of the component (B), which is a compound (B-1) having at least three glycidyl groups in the molecule or a compound (B-2) having at least two epoxy groups in the molecule, and 0 to 20 parts by weight of a cyclic ether compound (C) copolymerizable with trioxane, and which has a total terminal group amount of 15 to 150 mmol/kg, when (B) is (B-2).Type: GrantFiled: July 5, 2001Date of Patent: April 2, 2002Assignee: Polyplastics Co., Ltd.Inventors: Hidetoshi Okawa, Kaoru Yamamoto
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Publication number: 20020013447Abstract: The invention provides a method for treating drill cuttings, preferably marine cuttings, preferably in situ, so that the cuttings can be discharged into the environment, preferably back into marine waters without causing oxygen depletion of marine sediment. In a preferred embodiment, the treatment emulsifies and then encapsulates free hydrocarbons in the marine cuttings.Type: ApplicationFiled: April 16, 2001Publication date: January 31, 2002Inventors: Lirio Quintero, Jose Limia
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Patent number: 6255440Abstract: Polyacetal copolymers, obtained by copolymerizing (A) 100 parts by weight of trioxane, (B) 0.01 to 10 part(s) by weight of at least one compound selected from among glycidyl ether compounds of the following general formula (I), (II) or (III) and (C) 0 to 20 part(s) by weight of a cyclic ether compound [excluding the glydicyl ether compound (B)] copolymerizable with trioxane, are a polyacetal resin having a high rigidity, excellent creep properties, a high surface hardness and excellent sliding properties: wherein R1 is a C1-12 alkyl group, an aryl group or a substtituted aryl group; wherein R2 represents a C2-20 polyalkylene oxide glycol residue; wherein R4 represents an alkyl group having 1 to 30 carbon atoms; R5 represents an alkylene group having 1 to 30 carbon atoms.Type: GrantFiled: September 21, 2000Date of Patent: July 3, 2001Assignee: Polyplastics Co., Ltd.Inventors: Hidetoshi Okawa, Yoshihisa Tajima
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Patent number: 6208553Abstract: This invention provides novel high density memory devices that are electrically addressable permitting effective reading and writing, that provide a high memory density (e.g., 1015 bits/cm3), that provide a high degree of fault tolerance, and that are amenable to efficient chemical synthesis and chip fabrication. The devices are intrinsically latchable, defect tolerant, and support destructive or non-destructive read cycles. In a preferred embodiment, the device comprises a fixed electrode electrically coupled to a storage medium comprising one or more thiol-derivatized porphyrins. The storage medium has a multiplicity of different and distinguishable oxidation states and data is stored in said oxidation states by the addition or withdrawal of one or more electrons from the storage medium via the electrically coupled electrode(s).Type: GrantFiled: July 1, 1999Date of Patent: March 27, 2001Assignee: The Regents of the University of CaliforniaInventors: Daniel Tomasz Gryko, Peter Christian Clausen, Kristian M. Roth, David F. Bocian, Werner G. Kuhr, Jonathan S. Lindsey
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Patent number: 6139804Abstract: A process for producing a polyoxymethylene using a reactor having a discharging port having a weir, which process comprises introducing trioxane or a mixture of trioxane and a compound reactive therewith into the reactor from its feeding port and continuously recovering the powdery polyoxymethylene formed, from said discharging port having a weir. Owing to the presence of the weir, the residence time of reaction mixture in reactor is long, making high the conversion of the monomer.Type: GrantFiled: April 24, 1997Date of Patent: October 31, 2000Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Yukio Tanigawa, Hiromasa Matumoto
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Patent number: 6072021Abstract: This invention concerns a process for the copolymerization of formaldehyde with cyclic ethers, the process comprising combining in a hydrocarbon solvent a cyclic ether, a cationic initiator comprising an anion formed from tetraphenyl borate derivatives, and mixtures thereof, and a cation, and anhydrous formaldehyde. These initiators provide high activity, high cyclic ether incorporation rates, and stability while minimizing the production of by-products.Type: GrantFiled: October 21, 1998Date of Patent: June 6, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Douglas John Adelman, Richard Beckerbauer
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Patent number: 5994455Abstract: A process for the preparation of polyoxymethylene copolymers, wherein 1,3,5-trioxane is polymerized with generally known comonomers in the presence of a strong protonic acid initiator and in the presence of a formaldehyde dialkyl acetal, and wherein the initiator is dissolved in the formaldehyde dialkyl acetal before admixing to the trioxane and the comonomers.Type: GrantFiled: September 8, 1998Date of Patent: November 30, 1999Assignee: Ticonna GmbHInventors: Karl-Friedrich Muck, Horst Roschert, Robert M. Gronner, Satyajit Verma, Michael G. Yearwood
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Patent number: 5973072Abstract: The present invention is directed to a polymeric vehicle, the formulated coating composition and a coating binder made from the polymeric vehicle and a method for making the polymeric vehicle where the polymeric vehicle includes a phenolic urethane reactive diluent. The phenolic urethane reactive diluent may be made from a phenolic ester alcohol having at least one aliphatic hydroxyl group.Type: GrantFiled: March 21, 1996Date of Patent: October 26, 1999Assignee: Exxon Chemical Patents, Inc.Inventors: Frank N. Jones, Vijay Swarup, Ramachandran P. Subrayan, Suru Zhang
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Patent number: 5942595Abstract: Disclosed is a process for copolymerization of formaldehyde with cyclic ethers in the presence of organic nitro compounds. The process enhances the selectivity for the cyclic copolymer.Type: GrantFiled: July 13, 1998Date of Patent: August 24, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Douglas John Adelman, Richard Beckerbauer
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Patent number: 5929195Abstract: A branched or crosslinked polyacetal resin is excellent in blow moldability, has impact resistances such as plane impact resistance, and the smoothness of the inner surfaces of moldings produced therefrom, and is suitable for molding, particularly blow molding. It can be produced by the bulk polymerization of (A) trioxane with (B) a cyclic ether and/or cyclic formal and (C) a polyfunctional glycidyl ether compound in the presence of (D) a cationic polymerization catalyst, a mixture prepared by mixing the cyclic ether and/or cyclic formal (B) with the polyfunctional glycidyl ether compound (C) and the cationic polymerization catalyst (D) is added to trioxane (A) to conduct the polymerization.Type: GrantFiled: July 14, 1998Date of Patent: July 27, 1999Assignee: Polyplastics Co., Ltd.Inventors: Kuniaki Kawaguchi, Kaoru Yamamoto, Hajime Serizawa
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Patent number: 5873911Abstract: Polymeric, water soluble, quaternary ammonium compounds (F) obtainable by quaternization of(a) at least one amino-group-containing urea compound that contains one or more groups of the formula--NH--CO--NH--G--L-- (.alpha.)in which G signifies a bridging groupand L signifies a tertiary, quaternizable amino groupwith(b) (b.sub.1) an epihalohydrin and optionally(b.sub.2) at least one further quaternizing agentto a quaternized product (q)and reaction of the quaternized product (q) with(c) a dialdehyde of formula (I) ##STR1## in which Z signifies methylene or the direct bond, or a urea derivative thereof, are suitable as fixing adjuvants in particular in continuous processes under nearly neutral to acidic conditions especially for the improvement of wet fastnesses of dyeings on hydrophilic fibrous material.Type: GrantFiled: August 14, 1997Date of Patent: February 23, 1999Assignee: Clariant Finance (BVI) LimitedInventors: Bernard Danner, Francis Palacin
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Patent number: 5849858Abstract: Furfuryl alcohol/formaldehyde resins exhibiting high water compatibility and low amounts of volatile organic compounds such as furfuryl alcohol.Type: GrantFiled: April 2, 1998Date of Patent: December 15, 1998Assignee: QO Chemicals, Inc.Inventors: George S. Everett, George R. MacLennan, Michael C. Chen
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Patent number: 5760142Abstract: Epoxide-amine dendrimers synthesized by a repetitive and step-wise addition reaction of epoxides comprising functional moieties which are available for conversion into amino groups followed by a reaction of these groups to primary amino moieties. The amino terminated dendrimers are reacted with (2,3-epoxypropoxy) methacrylate, a monoepoxide and/or a monoisocyante. The methacrylate terminated dendrimers are polymerizable using redox initiators and/or photoinitiators. The resulting dendrimers show a very low volume shrinkage from that of the starting materials, on the order of less than about 5 percent by volume.Type: GrantFiled: December 4, 1996Date of Patent: June 2, 1998Assignee: Dentsply DeTrey G.m.b.H.Inventor: Joachim E. Klee
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Patent number: 5756594Abstract: Polymers which contain polyacetal blocks are obtainable by polymerizing carboxylates containing aldehyde groups in the presence of initiators and reacting the polymers with at least bifunctional crosslinking agents in the presence of acids or Lewis acids and, if required hydrolyzing the ester groups present as polymerized units, process for the preparation of the polymers containing polyacetal blocks by polymerizing carboxylates containing aldehyde groups in the presence of initiators and reacting the resulting polyacetals containing terminal hydroxyl groups with at least bifunctional crosslinking agents in the presence of acids or Lewis acids, and the use of the resulting polymers as additives in phosphate-free and reduced phosphate detergents and cleaning agents, as scale inhibitors and as dispersants for pigments.Type: GrantFiled: September 19, 1997Date of Patent: May 26, 1998Assignee: BASF AktiengesellschaftInventors: Angelika Funhoff, Dieter Boeckh, Matthias Kroner, Richard Baur, Alexander Kud, Gunnar Schornick, Volker Schwendemann
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Patent number: 5728798Abstract: In preparing a polyacetal copolymer through copolymerization of trioxane as the principal monomer with a cyclic ether or cyclic formal having at least one carbon-carbon bond as the comonomer, 0.05 to 100 ppm (on the weight basis), based on the total amount of the monomers, of a heteropoly-acid or an acidic salt thereof is used as a polymerization catalyst, and a liquid mixture preliminarily prepared by mixing at least part or the whole of the comonomer with the polymerization catalyst is added to trioxane to effect copolymerization. According to such the process, the polymerization yield and the degree of polymerization (molecular weight) are enhanced, and a polyacetal copolymer having an improved stability can be obtained.Type: GrantFiled: March 7, 1997Date of Patent: March 17, 1998Assignee: Polyplastics Co., Ltd.Inventors: Akira Nakai, Kaoru Yamamoto
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Patent number: 5552510Abstract: The present invention relates to copolymers, to a process for their preparation and to their use for the production of ionically conductive materials. A copolymer according to the invention consists of monomer units corresponding to the formula --CH.sub.2 --O--CHR--CH.sub.2 O (I) and monomer units corresponding to the formula --CH.sub.2 --CHR'--O-- (II), in which: R denotes a hydrogen atom, a linear or branched alkyl radical containing from 1 to 8 carbon atoms or a radical CH.sub.3 (--O--CH.sub.2 --CH.sub.2).sub.n --O--CH.sub.2 --, in which 1.ltoreq.n.ltoreq.10; R' denotes an aliphatic radical containing an unsaturation which can be polymerized by a radical route and inert in the conditions of cationic polymerization. The copolymers can be obtained by cationic polymerization of the appropriate oxirane and dioxolane. Application to the production of ionically conductive materials.Type: GrantFiled: May 27, 1994Date of Patent: September 3, 1996Assignees: Centre National De La Recherche Scientifique, Hydro-QuebecInventors: Jean-Yves Sanchez, Michel Armand, Jean-Pierre Petit, Yves Choquette, Glaura Goulart Silva
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Patent number: 5512608Abstract: A multi-part composition is provided which is suitable for use as an adhesive, a potting compound, a coating or a sealant. It consists of a polymerizable acrylate formulation and an activating formulation, the latter usually comprising an amine-aldehyde condensation product diluted with a liquid vinyl ether; liquid epoxides may also be included as diluents in the activating formulation.Type: GrantFiled: January 27, 1995Date of Patent: April 30, 1996Assignee: Dymax CorporationInventors: Andrew G. Bachmann, Stephen E. Cantor
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Patent number: 5506332Abstract: A process for preparing polyacetals by copolymerization of glyoxylic esters with other copolymerizable monomers in the presence of anionic or cationic polymerization initiators, with or without the introduction of stable end groups and with or without hydrolysis of the copolymerized units of glyoxylic ester present in the copolymer comprises using as monomers cyclic formals derived from diols, homopolymers of formaldehyde, trioxepane or mixtures thereof, although up to 50% by weight of this group of monomers may be replaced by other customary copolymerizable monomers, and the poly(acetal-carboxylate)s thus obtainable are useful as additives in reduced-phosphate and phosphate-free detergents and cleaners, as water treatment agents and as dispersants for finely divided substances.Type: GrantFiled: February 2, 1995Date of Patent: April 9, 1996Assignee: BASF AktiengesellschaftInventors: Angelika Funhoff, Graham E. McKee, Heinrich Hartmann, Richard Baur, Alexander Kud, Volker Schwendemann
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Patent number: 5500477Abstract: A moulding composition based on linear polyoxymethylene copolymers and customary additives with a melt index MFI (2,16 kg, 190.degree. C.) of .ltoreq.0,8, preferably .ltoreq.0,5 and especially .ltoreq.0,2 g/10 min has an extraordinary high toughness, which eliminates an addition of elastomer modifiers. In its preparation Lewis acids or protonic acids are used as initiators.Type: GrantFiled: April 26, 1995Date of Patent: March 19, 1996Assignee: Hoechst AktiengesellschaftInventors: Gerhard Reuschel, Dietrich Fleischer, Kaoru Yamamoto, Shuichi Chino
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Patent number: 5447996Abstract: There are disclosed an adhesive obtained by dispersing a cured amino resin fine powder soluble in acid or oxidizing agent into an uncured heat-resistant resin matrix hardly soluble in acid or oxidizing agent when being subjected to a curing treatment as well as a printed circuit board using this adhesive and a method of producing the same. The adhesive has excellent properties such as resistance to chemicals, heat resistance, electric properties, hardness and adhesion property owing to the use of the amino resin fine powder. Therefore, the printed circuit board using such an adhesive is not influenced by service circumstance and is high in the connection reliability without forming short circuit between patterns. Furthermore, in the method of producing the printed circuit board, the adhesive is provided in form of a sheet-or a prepreg, whereby the printed circuit board can be produced easily and cheaply.Type: GrantFiled: May 24, 1994Date of Patent: September 5, 1995Assignee: Ibiden Co., Ltd.Inventors: Motoo Asai, Chie Onishi
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Patent number: 5385958Abstract: A multi-part composition is provided which is suitable for use as an adhesive, a potting compound, a coating or a sealant. It consists of a polymerizable acrylate formulation and an activating formulation, the latter usually comprising an amine-aldehyde condensation product diluted with a liquid vinyl ether; liquid epoxides may also be included as diluents in the activating formulation.Type: GrantFiled: March 5, 1993Date of Patent: January 31, 1995Assignee: Dymax CorporationInventors: Andrew G. Bachmann, Stephen E. Cantor
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Patent number: 5373068Abstract: Use of isophoronediamine isomer mixtures containing more than 40%, preferably more than 50 up to 70%, of the trans-isomer and less than 60%, preferably less than 50 down to 30%, of the cis-isomer as reactant in polyaddition resins selected from epoxy, polyurethane and polyurea resins. As curing agents in epoxy resins compared with previously known isomer mixtures, the isomer mixtures containing more than 40% of the trans-isomer and less than 60% of the cis-isomer unexpectedly lead to an extended pot life with simultaneously reduced maximum curing temperature and therefore reduced shrinkage problems. The isomer mixtures are also surprisingly suitable as amine components with reduced reactivity for the chain extension of polyurethane/polyureas.Type: GrantFiled: September 9, 1993Date of Patent: December 13, 1994Assignee: Degussa AktiengesellschaftInventors: Hermann Piana, Klaus Huthmacher
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Patent number: 5344893Abstract: There are disclosed an adhesive obtained by dispersing a cured amino resin fine powder soluble in acid or oxidizing agent into an uncured heat-resistant resin matrix hardly soluble in acid or oxidizing agent when being subjected to a curing treatment as well as a printed circuit board using this adhesive and a method of producing the same. The adhesive has excellent properties such as resistance to chemicals, heat resistance, electric properties, hardness and adhesion property owing to the use of the amino resin fine powder. Therefore, the printed circuit board using such an adhesive is not influenced by service circumstance and is high in the connection reliability without forming short circuit between patterns. Furthermore, in the method of producing the printed circuit board, the adhesive is provided in form of a sheet or a prepreg, whereby the printed circuit board can be produced easily and cheaply.Type: GrantFiled: July 17, 1992Date of Patent: September 6, 1994Assignee: Ibiden Co., Ltd.Inventors: Motoo Asai, Chie Onishi
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Patent number: 5273792Abstract: The present invention is directed to a novel epoxy polymeric composition resulting from reacting (A) at least one compound containing an average of more than one epoxide group per molecule with (B) at least one curing agent for component (A). At least a portion of the curing agent (B) is at least a first curing agent compound which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron withdrawing group. The present invention also includes a process for preparing the above polymeric materials. The polymeric materials of the present invention also exhibit nonlinear optical capabilities when formed into an optically transparent medium with a noncentrosymmetric alignment of molecules. The nonlinear optical materials of the present invention are useful in electrooptic devices for use in communications and data-processing.Type: GrantFiled: March 13, 1992Date of Patent: December 28, 1993Assignee: The Dow Chemical CompanyInventor: John J. Kester
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Patent number: 5270355Abstract: A paper coated resin has been provided which simultaneousy provides coated papers with improved ink receptivity, water resistance and blister resistance in a good balance. The resin is obtainable by introducing alicyclic amino and/or alicyclic epoxy compounds into a polyalkylenepolyamine-urea-aldehyde(epihalohydrin) resin or by introducing alicyclic amino and/or alicyclic epoxy compounds into a polyalkylenepolyamine-urea-aldehyde(epihalohydrin) resin and/or an amine-epihalohydrin resin and reacting or mixing these resins.Type: GrantFiled: January 13, 1992Date of Patent: December 14, 1993Assignee: DIC-Hercules Chemicals, Inc.Inventors: Hiroharu Kawano, Satoshi Takizawa, Hiroki Owaki, Haruka Hirayama
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Patent number: 5260405Abstract: A binding agent for molding compositions and molded bodies produced by reacting a low molecular weight lignin from the Organosolv process with phenol in a weight ratio of 1:20 to 3:1 at 100.degree. to 180.degree. C., adjusting the pH to an acidic value and condensing the mixture with 0.2 to 0.9 moles of formaldehyde per mole of phenol at 60.degree. to 120.degree. C. to form the binding agent useful for producing curable molding compositions, high-temperature molding compositions, refractory products, textile fleeces and friction coatings as well as carbon materials.Type: GrantFiled: October 26, 1992Date of Patent: November 9, 1993Assignee: Rutgerswerke Aktiengesellschaft AGInventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
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Patent number: 5254639Abstract: A binding agent for molded bodies and molding compositions produced by prereacting a mixture of 5 to 60% by weight of lignin or a lignin fraction produced by the Organosolv process and 40 to 95% by weight of a phenol novolac resin and subjecting the latter to high shear forces in a kneader or extruder and optionally mixing the same with a curing agent useful in molding compositions and high temperature-stable molded products such as refractory products, friction coatings, textile fleeces and carbon or graphite materials.Type: GrantFiled: October 26, 1992Date of Patent: October 19, 1993Assignee: Rutgerswerke Aktiengesellschaft AGInventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
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Patent number: 5158611Abstract: A process for producing a resin is disclosed, comprising reacting (a) a polyalkylenepolyamine, (b) an alicyclic dibasic carboxylic acid and/or a reaction product having a free carboxyl group that is obtained by reacting an alicyclic dibasic carboxylic acid with a glycol, (c) a urea, and (d) an aldehyde and/or an alkylating agent. The resulting resin is useful as a wet strength agent to provide a paper coating composition having improved printability and printing effects.Type: GrantFiled: August 22, 1991Date of Patent: October 27, 1992Assignee: Sumitomo Chemical Co., Ltd.Inventors: Shigeru Ura, Haruo Tanaka, Hisao Takagishi, Yoshiya Fukuyama, deceased, Hiroko Fukuyama, heir, Takuya Fukuyama, heir, Yuko Fukuyama, heir
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Patent number: 5093462Abstract: Hydroxy functional epoxidized amino resins comprising glycidamide groups. The polyglycidamides are produced from alkoxymethyl amino resins by reaction with acrylamide, followed by reaction with a polyol to introduce hydroxy functionality and then the unsaturated groups of the hydroxyfunctional acrylamidomethyl amino resins are epoxidized with an epoxidation agent such as hydrogen peroxide. The polyglycidamides are formulated with epoxy reactants to provide curable epoxy systems.Type: GrantFiled: May 27, 1988Date of Patent: March 3, 1992Assignee: Monsanto CompanyInventor: William F. Pfohl
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Patent number: 5079330Abstract: A polyoxymethylene multi-copolymer obtainable by copolymerizing(a) trioxane,(b) at least one cyclic ether or formal compound chosen from the group of ethylene oxide, 1,3-dioxolane, 1,3-dioxepane, 1,3,5-trioxepane and 1,3,6-trioxocane, and(c) at least one compound chosen from the group of glycidyl phenyl ether, styrene oxide and glycidyl naphthyl ether,and characterized in that the number average molecular weight of said polyoxymethylene multi-copolymer is from 10,000 to 100,000, that the melting point (Tm) and crystallization temperature (Tc) there of are in a relationship ofTm-Tc<15 (.degree.C.)and that the size of the spherulites is 10 .mu.m or less, or a resin composition comprised of this polyoxymethylene multi-copolymer and a polyoxymethylene resin, is distinguished in crystallinity, mechanical strength and surface appearance and is particularly suited for faster cycle molding.Type: GrantFiled: August 6, 1990Date of Patent: January 7, 1992Assignee: Toray Industries, Inc.Inventors: Yoshiki Makabe, Shigeru Okita, Yoshiyuki Yamamoto
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Patent number: 5034499Abstract: Acetal copolymers of trioxane with epoxy functional groups are obtained by copolymerizing trioxane with 5,6-epoxy-1,3-dioxepane. The epoxide group in the polymer chain provides a highly reacting functional group for further modification. Acetal copolymers with backbone epoxide groups exhibit toughness and thermal stability. The backbone epoxide groups can also be aminated in a one step hydrolysis-amination process.Type: GrantFiled: April 13, 1988Date of Patent: July 23, 1991Assignee: Hoechst Celanese Corp.Inventors: Nan-Loh Yang, Andrew Auerbach, James L. Paul, Yong C. Zheng, Shian S. Wang
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Patent number: RE39182Abstract: A process for the preparation of polyoxymethylene copolymers, wherein 1,3,5-trioxane is polymerized with generally known comonomers in the presence of a strong protonic acid initiator and in the presence of a formaldehyde dialkyl acetal, and wherein the initiator is dissolved in the formaldehyde dialkyl acetal before admixing to the trioxane and the comonomers.Type: GrantFiled: November 30, 2001Date of Patent: July 11, 2006Assignee: Ticona GmbHInventors: Karl-Friedrich Mück, Horst Röschert, Robert M. Gronner, Satyajit Verma, Michael G. Yearwood