Polymerizing In The Presence Of A Specified Material Other Than A Reactant Patents (Class 528/408)
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Patent number: 5726216Abstract: Mixtures of epoxy resins with cationic initiators are curable under high energy ionizing radiation such as electron beam radiation, X-ray radiation, and gamma radiation. The composition of this process consists of an epoxy resin, a cationic initiator such as a diaryliodonium or triarylsulfonium salt of specific anions, and a toughening agent such as a thermoplastic, hydroxy-containing thermoplastic oligomer, epoxy-containing thermoplastic oligomer, reactive flexibilizer, rubber, elastomer, or mixture thereof. Cured compositions have high glass transition temperatures, good mechanical properties, and good toughness. These properties are comparable to those of similar thermally cured epoxies.Type: GrantFiled: July 8, 1996Date of Patent: March 10, 1998Assignee: Lockheed Martin Energy Systems, Inc.Inventors: Christopher J. Janke, George F. Dorsey, Stephen J. Havens, Vincent J. Lopata
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Patent number: 5723562Abstract: 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: December 5, 1996Date of Patent: March 3, 1998Assignee: Elf Atochem North America, Inc.Inventor: Daryl L. Stein
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Patent number: 5712331Abstract: A curable resin system in supercritical carbon dioxide as diluent includes an epoxy resin, a co-reactant selected from poly N-substituted aziridines, and a catalyst to promote cure at ambient temperature. The system is compatible with various epoxy resins such as bisphenol A epoxy, bisphenol F epoxy, novolac epoxy, cycloaliphatic epoxy, triglycidyl-aminophenol, and triglycidyl isocyanurate. The aziridine co-reactant may be selected from reaction products of NH aziridines with acrylates and methacrylates of trimethylolpropane, ethylene glycol, propylene glycol, bisphenol A, bisphenol F, pentaerythritol, glycerol, and their alkoxylated derivatives; reaction products of NH aziridines with epoxy compounds; and 1-aziridine ethanol and its reaction products with epoxy and isocyanate functional compounds. Suitable catalysts include acid salts and complexes, strong electron accepting compounds, combinations of silicon hydrides and metal complexes, and non-halogen containing boron derivatives.Type: GrantFiled: August 15, 1995Date of Patent: January 27, 1998Assignee: Rockwell International CorporationInventor: Hong-Son Ryang
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Patent number: 5668244Abstract: A liquid polyester obtained by reacting a cyclic acid anhydride (A) containing at least 10 mol % of one of specific cyclic acid anhydrides with an epoxy compound (B) in a cyclic acid anhydride (A):epoxy compound (B) molar ratio of 10:8-10:12, can be applied with a conventionally generally used film-forming machine such as a roll coater or a printing machine, can easily give a film-forming material such as a solvent-free coating composition or ink and a curable liquid resin for use as an adhesive, is a low-temperature curing liquid polyester useful as a compatibilizer, a surface-tension modifier, a pigment dispersing agent and a metal chelating agent, and is curable in air in the presence of a relatively small amount of a catalyst.Type: GrantFiled: June 16, 1995Date of Patent: September 16, 1997Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Miki Kawashima, Takeo Yamaguchi, Kunio Horiuchi, Hiromi Uchida
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Patent number: 5646226Abstract: A method for producing sucrose-based epoxy monomers having one to eight epoxy groups per molecule of sucrose, which comprises reacting a mixture comprising: a sucrose monomer having an allyl-containing group on at least one of the hydroxyl groups, and a reagent or catalyst selected from molybdenum, tungsten, vanadium, titanium and peracid, in the presence of hydrogen peroxide or a derivative thereof, in relative amounts sufficient to produce a sucrose-based epoxy monomer. Monomers thus produced are also provided. The sucrose-based epoxy monomers can be cured to produce a sucrose-based epoxy resin. Such resins are useful, for example, as adhesives, composites and coatings.Type: GrantFiled: June 6, 1996Date of Patent: July 8, 1997Assignee: Hawaii Agriculture Research CenterInventors: Navzer D. Sachinala, Morton H. Litt
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Patent number: 5620831Abstract: Disclosed are novel cyanoguanidine derivatives which are usable as an epoxy resin curing agent and are represented by the following general formula (1). A thermosetting resin composition and a photocurable and thermosetting resin composition containing the following cyanoguanidine derivatives and other derivatives as the epoxy resin curing agent are also disclosed. ##STR1## wherein R.sup.1 represents a substituent selected from the group consisting of the following substituents (a) through (k).Type: GrantFiled: March 28, 1995Date of Patent: April 15, 1997Assignee: Taiyo Ink Manufacturing Co., Ltd.Inventor: Osamu Kawana
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Patent number: 5621131Abstract: Conjugated polymers comprising recurring units of the formula (I), ##STR1## A, B, C, D are identical or different and are each from one to fifteen identical or different arylene and/or heteroarylene and/or vinylene groups which, like the spirobifluorene skeleton itself, may be unsubstituted or substituted;S are identical or different substituents;m, n are 0 or 1.The polymers of the invention having the formula (I) are suitable as electroluminescence materials and have, in particular, a high color purity of the emission.Type: GrantFiled: October 12, 1995Date of Patent: April 15, 1997Assignee: Hoechst AktiengesellschaftInventors: Willi Kreuder, Donald Lupo, Josef Salbeck, Hermann Schenk, Thomas Stehlin
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Patent number: 5565527Abstract: Polymeric, catalytically active compounds comprising polymer chains to which imidazole groups are linked terminally or laterally are used as catalysts for the dimerization of isocyanates.Type: GrantFiled: June 1, 1995Date of Patent: October 15, 1996Assignee: BASF AktiengesellschaftInventors: Bernd Bruchmann, Roland Minges, Christian Schade, Konrad Stiefenhoefer
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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: 5545712Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered, alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.Type: GrantFiled: August 23, 1995Date of Patent: August 13, 1996Assignee: Mitsu Toatsu Chemicals, Inc.Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
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Patent number: 5510457Abstract: A method for preparing a processable polyisothianaphthene polymer includes steps of dissolving an isothianaphthene monomer in a solvent and introducing therein an initiator to initiate a polymerization reaction to produce a precursor of poly(dihydroisothianaphthene), dissolving thoroughly the precursor of poly(dihydroisothianaphthene) in the solvent in an appropriate ratio to obtain a poly(dihydroisothianaphthene) solution, proceeding a dehydrogenation reaction for the poly(dihydroisothianaphthene) solution by introducing a dehydrogenation agent to obtain a polyisothianaphthene microgel solution, and terminating the dehydrogenation reaction by introducing an inhibitor. This invention offers a simple, feasible, and economical way to prepare a large-area film with uniform film thickness, excellent stability, and good electrochromic, conducting, and mechanical properties.Type: GrantFiled: April 24, 1995Date of Patent: April 23, 1996Assignee: National Science CouncilInventors: Show-An Chen, Chin-Chang Lee
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Patent number: 5508379Abstract: Polyester polymers having pendant carbamate groups are disclosed. The polymers are prepared by reacting:(a) reacting a hydroxyalkyl cyclic carbonate compound with a compound having at least one cyclic anhydride group to form a half-ester acid comprising a cyclic carbonate group,(b) reacting the cyclic carbonate group on the half-ester from step (a) with ammonia, ammonium hydroxide, or a primary amine to ring open the cyclic carbonate and form a compound comprising an acid group, a hydroxyl group, and a pendant carbamate group, and(c) reacting a mixture comprising the compound from step (b) and optionally comprising a polyol or a polyacid or both to form the polyester having pendant carbamate groups.Type: GrantFiled: December 21, 1994Date of Patent: April 16, 1996Assignee: BASF CorporationInventors: Gregory L. Menovcik, Walter H. Ohrbom
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Patent number: 5492996Abstract: Alcohol-soluble aromatic heterocyclic polymers having repeating units of the formula: ##STR1## wherein X is --O-- or --S--, and R is selected from the group consisting of: ##STR2## and R' is selected from the group consisting of alkyl having 1 to 5 carbon atoms, alkaryl having 7 to 12 carbon atoms, aralkyl having 7 to 12 carbon atoms and substituted aromatic having 1 to 3 substituent groups.The alcohol-soluble polymers may be used for fabricating organic/inorganic hybrid composites with metal alkoxides M(OQ).sub.v, wherein M is Si, Ti, Al or the like and Q is a lower alkyl group. These polymers can also be used to coat materials or substrates which are susceptible to attack by highly corrosive acids. On drying, the ionic bond between the trialkylamine and the sulfo group is broken and the polymer reverts to the parent structure, thereby leaving a polymer coating. Yet further, the original amine can be exchanged with a less volatile amine or an amine having a desired functionality.Type: GrantFiled: February 21, 1995Date of Patent: February 20, 1996Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Thuy D. Dang, Jom P. Chen, Fred E. Arnold
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Patent number: 5493005Abstract: Alcohol-soluble, aromatic heterocyclic copolymers having repeating units of the formula: ##STR1## wherein x has a value of 0.10 to 0.90 and y has a value of 1.0-x. These copolymers are useful in the preparation of organic/inorganic hybrid materials having transparency which comprise the sol-gel derived, hydrolytically condensed reaction product of a metal alkoxide of the formula M(OR).sub.w wherein R is a lower alkyl group, M is Si, Ti, Al or a mixture thereof, and w is the valence value of M, and the above copolymer.Type: GrantFiled: February 21, 1995Date of Patent: February 20, 1996Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Fred E. Arnold, Jom P. Chen
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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: 5468841Abstract: The present invention provides an improved method of carrying out cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO). Such cyclic ether monomers are polymerized with an initiator precursor (i.e., an alcohol) and boron trifluoride tetrahydrofuranate (BF.sub.3 .cndot.THF). It has been discovered that when boron trifluoride tetrahydrofuranate is used as a catalyst in the cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO), polymers are produced that have improved functionality and low poly-dispersity. The polymers formed using the method of the present invention are useful for forming cross-linked elastomers which, in turn, are useful for forming elastomeric binders for high-energy compositions, such as propellants, explosives, gasifiers or the like.Type: GrantFiled: April 13, 1994Date of Patent: November 21, 1995Assignee: Aerojet General CorporationInventors: Aslam A. Malik, Thomas G. Archibald, Roland P. Carlson, Gerald E. Manser
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Patent number: 5468840Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered. alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.Type: GrantFiled: August 29, 1994Date of Patent: November 21, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
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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: 5462698Abstract: A photochromic composition comprising (A) 100 parts by weight of a compound having at least one epoxy group in the molecule and (B) 0.0001 to 10,000 parts by weight of a photochromic compound. The compound (A) is represented by the following general formula ##STR1## wherein A is a residue of an n-valent alcoholic hydroxyl-containing compound, a residue of an n-valent phenolic-hydroxyl-containing compound, or a residue of an n-valent carboxylic acid, R.sup.1 is a hydrogen atom or a methyl group, and n is an integer of 1 to 4.Examples of the (B) photochromic compound include fulgide compounds, spirooxazine compounds and chromene compounds. A polymer obtained by polymerizing the above photochromic composition of the invention by a radical polymerization method has a good durability of photochromic properties, and also possesses a dark color-forming density, a fast color fading speed, is transparent, and has a high surface hardness. Thus, especially, the polymer is suitable for use as a photochromic lens.Type: GrantFiled: March 31, 1994Date of Patent: October 31, 1995Assignee: Tokuyama CorporationInventors: Takashi Kobayakawa, Satoshi Imura, Kazumasa Itonaga, Kazuhiko Kuramoto
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Patent number: 5453468Abstract: The invention relates to two classes of prepolymers containing a perfluoropolyethereal chain and carboxylic end groups, suitable as cross-linking agents for epoxy prepolymers. The first class contains anhydride-derived end groups; the second lactone-derived end groups; prepolymers therefrom are also disclosed. Additional non-fluorinated curing agents may also be added.Type: GrantFiled: January 24, 1995Date of Patent: September 26, 1995Assignee: Ausimont S.p.A.Inventors: Leno Mascia, Claudio Tonelli, Giovanni Simeone
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Patent number: 5447797Abstract: A reaction resin mixture, which is able to be hardened thermally and by means of UV radiation, contains the following constituents:a cationically polymerizable epoxide resin;a latent hardening initiator in the form of an aralkyl-thiolanium salt; anda sensitizer of the structure ##STR1## A being --CO--, --NR-- and --CO--CO--, and D being --O--, --S--, --CO-- and --CH.sub.2).sub.x (where x= 1 or 2) or rather a single bond or two hydrogen atoms.Type: GrantFiled: August 9, 1993Date of Patent: September 5, 1995Assignee: Siemens AktiengesellschaftInventors: Bernhard Stapp, Lothar Schoen, Volker Muhrer
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Patent number: 5444105Abstract: A composition is disclosed for transferring and adhering tape-mounted hisogical sections, to specimen mounting surfaces, usually glass microscope slides to expedite and simplify the safe removal of the mounting tape and the subsequent processing of the slide-mounted section. The composition is a curable polymeric mixture which has high tack prior to curing, is substantially non-diffusable and non-flowable into tissue sections and, after curing, has a refractive index substantially similar to that of the specimen section and is non-labile to conventional histological solvents and stains. A preferred composition comprises diacrylate-terminated polyurethane, a diacrylate ester of an epoxy resin and a diethoxyacetophenone initiator. It is usually formed onto the mounting surface as a solution in a conventional organic solvent, such as isopropanol or toluene.Type: GrantFiled: July 30, 1993Date of Patent: August 22, 1995Assignee: Mount Sinai School of Medicine of the City University of New YorkInventor: Leonard Ornstein
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Patent number: 5442035Abstract: Cure of an epoxy resin by an aliphatic amine is accelerated by a calcium sulfonate or calcium hydrocarbyl sulfate salt. The calcium salt is preferably a salt of a detergent-range sulfonic acid or hydrocarbyl sulfuric acid which is soluble in either the amine or the epoxy resin.Type: GrantFiled: September 29, 1993Date of Patent: August 15, 1995Assignee: Shell Oil CompanyInventors: Larry S. Corley, Harold E. De La Mare
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Patent number: 5393866Abstract: A method for the production of polytetramethylene ether glycol wherein polymerization of tetrahydrofuran in the presence of fluorosulfonic acid is followed by hydrolysis of the resulting polymer, characterized by(1) using the fluorosulfonic acid at 0.007-0.3 molar equivalents with respect to the tetrahydrofuran;(2) using in combination therewith fuming sulfuric acid which contains free sulfur trioxide at 0.05-1.0 molar equivalent with respect to the fluorosulfonic acid; and(3) adding said fuming sulfuric acid to the tetrahydrofuran prior to adding the fluorosulfonic acid thereto.According to the method, high quality polytetramethylene ether glycol with a low fluorine content may be obtained at a high yield without lowering the polymerization temperature. For example, PTMG may be obtained with 3 or fewer, and preferably 2 or fewer terminal fluorines per 2,000 termini of the resulting PTMG.Type: GrantFiled: November 10, 1993Date of Patent: February 28, 1995Assignee: Mitsubishi Kasei CorporationInventors: Nobuyuki Murai, Masayuki Shirato, Hiroshi Takeo, Hidetoshi Tanaka
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Patent number: 5391681Abstract: Curable compositions based on epoxy resins or a mixture of epoxy resins and polyisocyanates and containing at least one compound of formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are each independently of one another hydrogen, alkyl, aryl, arylalkyl or halogen, and R.sub.2 together with R.sub.3 and R.sub.5 together with R.sub.6 and R.sub.8 together with R.sub.9 may each also represent a fused benzene ring.The compositions have high reactivity and at the same time good storage stability.Type: GrantFiled: May 27, 1993Date of Patent: February 21, 1995Assignee: Ciba-Geigy CorporationInventors: Andreas Muhlebach, Peter Flury
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Patent number: 5374697Abstract: Sulfonium compounds of formula 1 or 2 ##STR1## wherein R is a mononuclear cycloalkyl radical containing 3 to 8 ring carbon atoms or a mononuclear cycloalkyl radical which contains 3 to 8 ring carbon atoms and to which at least one further ring containing carbon atoms is fused,X is a non-nucleophilic anion, andZ is a single bond, an oxygen or sulfur atom, a group of formula >S.sup..sym. --R X.sup..crclbar., wherein R and X are as defined above, or is >C.dbd.O or a methylene bridge,which sulfonium compounds are either unsubstituted or carry one or more than substituent selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.8 alkyl, phenyl, hydroxyl, C.sub.1 -C.sub.8 alkoxy, phenoxy, benzyloxy, alkoxycarbonyl containing 1 to 4 carbon atoms in the alkoxy moiety or acyl of 1 to 12 carbon atoms.Type: GrantFiled: July 14, 1993Date of Patent: December 20, 1994Assignee: Ciba-Geigy CorporationInventor: Beat Muller
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Patent number: 5344964Abstract: A method for preparing ester end-capped polyalkylene ether is disclosed. Cyclic ether monomers are subjected to ring-opening polymerization at a temperature of 10.degree.-80.degree. C. and a pressure of 0-10 atm in the presence of a solid acid of a mixed oxide of group III and group IV elements serving as catalyst and a mixture of acid and acid anhydride serving as molecular weight moidifier. The group III and group IV elements used should have a Ho index of +3.0 to -10.0.Type: GrantFiled: November 24, 1993Date of Patent: September 6, 1994Assignee: Industrial Technology Research InstituteInventors: Shiao-Jung Chu, Fu-Chen Liu, Ching-Tang Lin, Wen-Fa Lin, Kuei-Chih Wang, Sheng-Te Yang
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Patent number: 5338828Abstract: Novel cyclic imino ether compositions containing one or more mesogenic moieties, when polymerized, result in products having improved properties.Type: GrantFiled: September 10, 1993Date of Patent: August 16, 1994Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5336745Abstract: A method is provided for the direct synthesis of novel polymeric materials functionalized with desirable nitrogen-containing functional groups such as terminal azido, cyano, carbonylamino or thiocarbonylamino groups. Polymerization and functionalization occur in a substantially simultaneous manner. All necessary reactants for the functionalization are present when polymerization is initiated. The nitrogen-containing functional group is provided as a part of a molecule having a release moiety which is preferably resonance stabilized or of tertiary alkyl type and which acts to aid the nitrogen-containing species in functioning as a leaving group.Type: GrantFiled: May 16, 1991Date of Patent: August 9, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Herve M. Cheradame, Robert D. Lundberg, Frank J. Chen, Jean de la Crois Habimana
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Patent number: 5319068Abstract: Energetic binders, and, more specifically, a class of nitramine-containing polyether polymers characterized by favorable viscosity and glass transition temperature, as well as resistance to hydrolysis are prepared.Type: GrantFiled: February 3, 1992Date of Patent: June 7, 1994Assignee: Olin CorporationInventors: Roger W. Day, Rahim Hani
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Patent number: 5313000Abstract: This invention relates to the production of hydroxy-terminated polymers in the 2,000-20,000 MW range suitable for use as prepolymers in curing reactions with isocyanates to produce elastomers. The process involves the continuous addition over periods of 25-50 hours of an oxirane (monoepoxide) or a mixture of an oxirane and an oxetane to a reaction mixture, consisting of stoichiometric excesses of oxonium ion-forming catalyst such as BF.sub.3 -etherate and a diol initiator dissolved in an inert solvent. Under these conditions, chain extension of the diol occurs and the formation of cyclic oligomers and other impurities is minimised. The mole ratio of the initiator to catalyst is maintained at above 10:1 to suppress the formation of cationic terminal species on the growing polymer chain.Type: GrantFiled: January 27, 1992Date of Patent: May 17, 1994Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the U.K. of Britain and Northern IrelandInventor: Malcolm J. Stewart
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Patent number: 5302695Abstract: Polyethercyclicpolyols are prepared by thermally condensing a polyol having at least three hydroxyl groups of which at least two of the hydroxyl groups are vicinal, precursors of the glycol, cyclic derivatives of the polyol, or mixtures thereof, and controlling process conditions to avoid substantial undesirable degeneration. Lower molecular weight polyethercyclicpolyols are polycondensed with epoxy alcohols to form higher molecular weight polyethercyclicpolyols.Type: GrantFiled: September 10, 1993Date of Patent: April 12, 1994Assignee: Shell Oil CompanyInventors: Harry Frank, George C. Blytas, Anne H. Zuzich
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Patent number: 5296567Abstract: The present document describes the use of an inhibitor for cationic polymerization as an additive to a thermocurable composition based on at least one cationically polymerizable organic material and an initiator for cationic polymerization in the form of an onium compound or a compound of the formula (I)[M.sup.+n (L).sub.x ].sup.n+ nX.sup.- (I),in which n is 2 or 3, M is a metal cation selected from the group comprising Zn.sup.2+, Mg.sup.2+, Fe.sup.2+, Co.sup.2+, Ni.sup.2+, Cr.sup.2+, Ru.sup.2+, Mn.sup.2+, Sn.sup.2+, VO.sup.2+, Fe.sup.3+, Al.sup.3+ and Co.sup.3+, X.sup.- is an anion selected from the group comprising PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, BiF.sub.6.sup.-, derivatives of these anions in which at least one fluorine atom has been replaced by a hydroxyl group, and CF.sub.3 SO.sub.3.sup.-, or in which up to 50% of the anions X.sup.-, based on the total amount of anions, may be any desired anions, L is water or an organic .sigma.Type: GrantFiled: April 6, 1992Date of Patent: March 22, 1994Assignee: Ciba-Geigy CorporationInventors: Dieter Baumann, Werner Margotte, Beat Muller
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Patent number: 5294582Abstract: As a curing catalyst of epoxy resins, superacid salts of an N,N'-di- or N,N',N'-trisubstitued urea, the urea component of which is produced by reacting an organic isocyanate and a primary or secondary amine, at least one of which is monofunctional, are soluble in conventional organic solvents compatible with epoxy resins and catalyze the cationic polymerization reaction of epoxy resins at room temperature.Type: GrantFiled: June 14, 1993Date of Patent: March 15, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Tadafumi Miyazono, Koji Tabuchi
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Patent number: 5280069Abstract: The new compound N,N,N'N'-tetraglycidyl-3,3'-diethyl-4,4'-diaminodiphenylmethane and curable resin compositions containing it.Type: GrantFiled: April 30, 1991Date of Patent: January 18, 1994Assignee: Ciba-Geigy CorporationInventors: Bryan Dobinson, Michael R. Thoseby
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Patent number: 5278247Abstract: As a curing catalyst of epoxy resins, superacid salts of an N,N'-di- or N,N',N'-trisubstituted urea, the urea component of which is produced by reacting an organic isocyanate and a primary or secondary amine, at least one of which is monofunctional, are soluble in conventional organic solvents, compatible with epoxy resins and catalyze the cationic polymerization reaction of epoxy resins at room temperature.Type: GrantFiled: April 24, 1992Date of Patent: January 11, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Tadafumi Miyazono, Koji Tabuchi
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Patent number: 5264596Abstract: Isotactic poly(glycidyl nitrate) useful in solid propellants is produced by polymerizing chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate. Chiral (R) glycidyl nitrate or its enantiomer is prepared by sequential treatment of chiral (S) glycidyl tosylate or its enantiomer with nitric acid and sodium hydroxide. Chiral (S) glycidyl tosylate or its enantiomer, (R) glycidyl tosylate, can be produced by Sharpless epoxidation of allyl alcohol or by direct tosylation or commercially available chiral glycidol. Likewise, chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate, can be prepared directly via nitration of (S) or (R) glycidol, respectively.Type: GrantFiled: August 13, 1992Date of Patent: November 23, 1993Assignee: Thiokol CorporationInventors: Rodney L. Willer, Alfred G. Stern, Robert S. Day
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Patent number: 5254664Abstract: A reaction of the compound (A) having at least two 2-oxazoline groups with the compound (B) having at least two functional groups of one or a plural kind selected from the group consisting of an aromatic hydroxyl group, an amino group and a thiol group proceeds in a short period of time to produce a cured resin with superior mechanical strength, heat resistance and adhesion properties.Type: GrantFiled: December 31, 1991Date of Patent: October 19, 1993Assignee: Nippon Shokubai Co., Ltd.Inventors: Subhash C. Narang, Asutosh Nigam, Apparao Satyam, Susanna C. Ventura, Yoshihiro Arita
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Patent number: 5239042Abstract: There are disclosed dibenzofuran amorphous polymer comprising a recurring unit represented by following formula (II) and having a molecular weight giving a reduced viscosity of at least 0.2 dl/g as measured in the form of a 0.5% (W/V) solution in N-methyl-pyrrolidone at 25.degree. C., a process for producing said amorphous polymer, a dibenzofuran copolymer comprising, in addition to a recurring unit represented by following formula (II), at least one type of recurring unit represented by following general formula (III) in a specific proportion and having a molecular weight giving a reduced viscosity of at least 0.2 dl/g as measured in the form of a 0.5% (W/V) solution in concentrated sulfuric acid at 25.degree. C., and a process for producing said copolymer. ##STR1## wherein A is --O--, --CO--, --S--, --SO.sub.2 --, a divalent alkylene group or a single bond and n is a number of 0, 1 or 2.Type: GrantFiled: November 15, 1991Date of Patent: August 24, 1993Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Isaburo Fukawa, Tsuneaki Tanabe
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Patent number: 5219981Abstract: Polybenzazole polymers can be synthesized rapidly in large quantities at high molecular weight and high concentration by a two-step process of forming oligomers in a batch reactor and advancing the molecular weight of the polymer in an extruder.Type: GrantFiled: March 1, 1991Date of Patent: June 15, 1993Assignee: The Dow Chemical CompanyInventors: Thomas Gregory, Carl W. Hurtig, Harvey D. Ledbetter, Kenneth J. Quackenbush, Steven Rosenberg
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Patent number: 5218141Abstract: Polyoxybutylene polyoxyalkylene glycol dicarboxylates are prepared by a process in which tetrahydrofuran is copolymerized with a molar excess of a 1,2-alkylene oxide in the presence of a carboxylic anhydride using, as a catalyst, a bleaching earth containing less than 3% by weight of water.Type: GrantFiled: November 6, 1991Date of Patent: June 8, 1993Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 5216122Abstract: Residual ethylene oxide is removed from poly(ethylene oxide) by the steps of adding to particles of high molecular weight poly(ethylene oxide) a finely divided solid particulate material which is capable of coating the poly(ethylene oxide) particles and impeding their agglomeration under conditions of heating, heating the particles of poly(ethylene oxide) at a temperature of at least 40.degree. C. and preferably which is near their crystalline melting point, and maintaining the temperature for a sufficient time to reduce the ethylene oxide in the particles of poly(ethylene oxide) to ten ppm or less. In one embodiment, the poly(ethylene oxide) is heated by holding the particles in a heated enclosure; in another, it is heated as a slurry in a liquid medium; in yet another, it is heated by warm gas in a gaseously-fluidized bed; and in a fourth, it is heated by microwave radiation.Type: GrantFiled: May 21, 1991Date of Patent: June 1, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Walter T. Reichle, Geoffrey A. D'Netto, Guy M. Troy, Meyer R. Rosen, Elke M. A. Clark
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Patent number: 5210179Abstract: Hydroxyterminated prepolymers, used in curing reactions with isocyanates to produce elastomers, are prepared by continuously adding over periods of 12-50 hours an oxetane monomer to a reaction mixture containing a diol initiator and a catalyst capable of catalyzing the cationic quasi-living cationic polymerization of the monomer, the rate of addition to maintain stoichiometric excess over the monomer. Polymerization is terminated by adding brine. Polymers of increased molecular weight and reduced impurity levels result.Type: GrantFiled: January 28, 1992Date of Patent: May 11, 1993Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventor: Malcolm J. Stewart
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Patent number: 5210153Abstract: Novel block polymers which are thermoplastic elastomers which are thermoplastic elastomers are provided for use as binders in high-energy compositions such as propellants, explosives, gasifiers or the like. The block polymers have an ABA structure wherein the A blocks are crystalline at temperatures below 60.degree. C. and the B blocks are amorphous at temperatures above -20.degree. C. Both the A and B blocks are polyethers formed from monomers of oxetanes and/or tetrahydrofuran. The block polymers melt in the range of 60.degree. C. to 120.degree. C. and have low viscosities above their melting points due to mutual miscibility of the A and B blocks.Type: GrantFiled: January 6, 1992Date of Patent: May 11, 1993Inventors: Gerald E. Manser, Richard S. Miller
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Patent number: 5196259Abstract: Fibers may be prepregged with a dope containing polybenzoxazole or polybenzothiazole. The prepreg may be contacted with water or another nonsolvent to coagulate the polymer and form a matrix composite.Type: GrantFiled: December 7, 1990Date of Patent: March 23, 1993Assignee: The Dow Chemical CompanyInventors: Peter E. Pierini, Ritchie A. Wessling, Peter K. Kim
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Patent number: 5164477Abstract: A polyfunctional polymerization initiator suitable to cationic ring-opening polymerization of heterocyclic monomers, having at least one carbon atom bonded directly to a carbon-carbon double bond in a linear or cyclic organic group and, further, having at least two following groups containing the above said carbon atoms and represented by the general formula:--CH.sub.2 Xwhere X represents an electron attracting group such as I, Br, Cl, F, --OSO.sub.2 R, --SOR, --OCOR, --OPO(OR).sub.2 and --OP(OR)R and R is optionally selected from (substituted) alkyl groups or (substituted) aryl groups.Various types of telechelic polymer, block copolymer, comb-like polymer and star-like polymer having controlled molecular weight and narrow molecular weight distribution can be produced efficiently from the heterocyclic monomer as the starting material.Type: GrantFiled: August 2, 1991Date of Patent: November 17, 1992Assignee: Shiro KobayashiInventors: Shiro Kobayashi, Hiroshi Uyama
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Patent number: 5162494Abstract: Isotactic poly(glycidyl nitrate) useful in solid propellants is produced by polymerizing chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate. Chiral (R) glycidyl nitrate or its enantiomer is prepared by sequential treatment of chiral (S) glycidyl tosylate or its enantiomer with nitric acid and sodium hydroxide. Chiral (S) glycidyl tosylate or its enantiomer, (R) glycidyl tosylate, can be produced by Sharpless epoxidation of allyl alcohol or by direct tosylation of commercially available chiral glycidol. Likewise, chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate, can be prepared direcly via nitration of (S) or (R) glycidol, respectively.Type: GrantFiled: November 5, 1990Date of Patent: November 10, 1992Assignee: Thiokol CorporationInventors: Rodney L. Willer, Alfred G. Stern, Robert S. Day
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Patent number: 5149767Abstract: Thermosetting mixtures containing(a) an epoxy resin having on average more than one 1,2-epoxide group in the molecule,(b) a di- or polyisocyanate compound and(c) a sulfonium salt of the formulae I to IV ##STR1## in which A is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.10 cycloalkylalkyl or phenyl which is unsubstituted or substituted by one or more substitutents from the group comprising C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acryl having 1-12 C atoms, Ar, Ar.sub.1 and Ar.sub.2 indpendently of one another are each phenyl which is unsubstituted or substituted by one or more substitutents from the group comprising C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.Type: GrantFiled: October 11, 1990Date of Patent: September 22, 1992Assignee: Ciba-Geigy CorporationInventors: Kurt Munk, Martin Roth
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Patent number: 5132377Abstract: Quaternary ammonium salts of a non-nucleophilic anion having an .alpha.-substituted benzyl group attached to the quatenary nitrogen atom or having a heterocycle including the quaternary nitrogen atom are useful as a cation polymerization initiator having a heat latency. A variety of resinous compositions containing this initiator is also disclosed.Type: GrantFiled: June 4, 1990Date of Patent: July 21, 1992Assignee: Nippon Paint Company, LimitedInventors: Shinji Nakano, Satoshi Urano
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Patent number: 5130413Abstract: A process for producing an unsaturated group-terminated high-molecular weight polyalkylene oxide by adding an alkali metal and/or an alkali metal compound capable of producing an alkali metal hydroxide on reaction with water to a hydroxyl-terminated polyalkylene oxide having a repeating unit represented by formula --R.sup.1 --O-- (wherein R.sup.1 represents a divalent alkylene group having from 2 to 8 carbon atoms) to substitute the hydrogen atom of the hydroxyl end group with an alkali metal (alkoxidation) the resulting polyalkylene oxide is reacted with a polyhalogen compound to increase the molecular weight of the polyalkylene oxide and then additional alkali metal and/or alkali metal compound is added before reacting the resulting high-molecular weight polyalkylene oxide with an unsaturated halogen compound to introduce an unsaturated group to the molecular chain terminals.Type: GrantFiled: August 30, 1990Date of Patent: July 14, 1992Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Yukimitsu Asai, deceased, by Keiji Asai, legal representative, by Yoshie Asai, legal representative, Hiroyuki Kawata, Tooru Nakagawa