Reactant Contains A Single Hetero-atom In A Ring And At Least Three Carbon Atoms, E.g., Oxetane, Etc. Patents (Class 528/417)
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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: 5254416Abstract: An electron conductive high polymer is described, having at least a repeating unit represented by following formula (1); ##STR1## wherein X.sub.1 and X.sub.1 ' each represents a divalent linkage group; R.sub.1 and R.sub.1 ' each represents an alkylene group; R.sub.2 represents a cyclic ester derivative group, an acyclic ester derivative group, a cyclic ether derivative group, or a sulfone derivative group; R.sub.3 represents a hydrogen atom, an alkyl group, an aryl group, a cyclic ester derivative group, an acyclic ester derivative group, a cyclic ether derivative group, or a sulfone derivative group; a, b, and c each represents 0 or 1; and Y represents --NR.sub.4 --, --O--, --S--, --Te--, or --Se--wherein R.sub.4 represents a hydrogen atom, an alkyl group, or an aryl group. A positive electrode for battery using the electron conductive high polymer is also described.Type: GrantFiled: January 9, 1992Date of Patent: October 19, 1993Assignee: Fuji Photo Film Co., Ltd.Inventor: Tadahiko Kubota
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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: 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: 5200452Abstract: Difficultly inflammable polymeric resins are obtained by curing resin mixtures comprising(a) a resin component comprising at least one thermically curable 1-oxa-3-aza tetraline groups containing compound; and(b) an organic metal or semimetal compound, or a carbon monoxide complex compound, of an element of the 6th, 7th or 8th auxiliary group of the periodic system or of copper, antimony or bismuth.Type: GrantFiled: November 18, 1991Date of Patent: April 6, 1993Assignee: Gurit-Essex AGInventor: Herbert Schreiber
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Patent number: 5198532Abstract: 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 polyol, cyclic derivatives of the polyol, or mixtures thereof, and controlling process conditions to avoid substantial undesirable degeneration. Lower molecular weight polyethercyclicpolyols are polycondensed with epihalohydrins to form higher molecular weight polyethercyclicpolyols.Type: GrantFiled: April 14, 1992Date of Patent: March 30, 1993Assignee: Shell Oil CompanyInventors: George C. Blytas, Harry Frank, Anne H. Zuzich
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Patent number: 5175217Abstract: The invention relates to a method for the photochemical conversion of tachysterol compounds into previtamin D compounds and of trans-vitamin D compounds into cis-vitamin D compounds under the influence of radiation, by exposing the tachysterol compound and trans-vitamin D compound, respectively, dissolved in a suitable solvent system, in the presence of a polymeric photosensitizer consisting of a polymer chain ("backbone") comprising covalently bound sensitizers suitable for the photochemical conversion, to light with a wavelength of preferably between approx. 300 and approx.Type: GrantFiled: August 23, 1990Date of Patent: December 29, 1992Assignee: Duphar International Research B.V.Inventors: Eric Goethals, Sebastianus J. Halkes, Robert B. Koolstra
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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: 5162453Abstract: Comb-shaped polymers, comprised of hydrophilic backbones and dye-containi hydrophobic side chains are synthesized for use in multilayered, noncentrosymmetric, thin films by means of Langmuir-Blodgett processing techniques. The second harmonic signal generation exhibited by these films increases quadratically with the number of layers of polymeric dye in the film.Type: GrantFiled: November 29, 1990Date of Patent: November 10, 1992Assignee: The United States of America as represented by the Secretary of the NavyInventors: Robert C. Hall, Geoffry A. Lindsay, James M. Hoover
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Patent number: 5155237Abstract: 2,2-Dihydrocarbyl-3-propiolactones are prepared by the thermolysis at 175.degree. C. to 350.degree. C. of low molecular weight (oligomeric) poly(3-hydroxy-2,2-dihydrocarbylpropionic acid) that contains carboxyl ends groups, in the presence of alkali metal, ammonium or phosphonium cations. The propiolactones may be polymerized to high molecular weight polymers.Type: GrantFiled: January 22, 1991Date of Patent: October 13, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Roe C. Blume, Lewis E. Manring
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Patent number: 5099042Abstract: Polymers are produced from 4 and 5 member cyclic ethers, which polymers have hydroxyl functionalities of 4.Type: GrantFiled: March 14, 1989Date of Patent: March 24, 1992Assignee: Thiokol CorporationInventors: Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 5055547Abstract: The present invention relates to copolyethers comprising copolymers of 7,oxa-bicyclo(2,2,1)heptane, and its alkyl-derivatives, with one or more single-ring or condensed-rings cycloaliphatic ethers, comprising the characteristic group; ##STR1## wherein R' is hydrogen and R" is H, a halogen, or an alkyl radical containing a small number of carbon atoms, and which may also be halogen-substituted.If the ether contains one ring only, it contains from 5 to 12 atoms in the ring, and if it contains a condensed-ring system, it contains a total number of from 10 to 18 atoms in the rings.Those copolyethers show a anisotropic behaviour in the molten state, and therefore have liquid-crystal properties.Type: GrantFiled: May 10, 1989Date of Patent: October 8, 1991Assignee: Montedison S.p.A.Inventors: Leonardo Fiore, Giuseppe Motroni, Mauro Maritano
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Patent number: 5041531Abstract: A process for preparing polyepichlorohydrin which comprises polymerizing epichlorohydrin in the presence of a catalytic amount of 1,4-butaneditriflate. The resulting polymer can have a molecular weight of about 5,000 to about 15,000. The polymer is telechelic. It can be terminated with a broad variety of functional groups.Type: GrantFiled: April 27, 1990Date of Patent: August 20, 1991Assignee: The United States of America as represented by the Secretary of the Air ForceInventor: Chung S. Kim
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Patent number: 5032673Abstract: The present invention relates to copolyethers constituted by copolymers of 7,oxa-bicyclo(2,2,1)heptane, and its alkyl-derivatives, with one or more cycloaliphatic ethers, comprising from 2 to 4 carbon atoms in their ring.These copolyethers show an anisotropic behavior in the molten state, and therefore are endowed with liquid-crystal properties.Type: GrantFiled: May 8, 1989Date of Patent: July 16, 1991Assignee: Montedison S.p.A.Inventors: Leonardo Fiore, Giuseppe Motroni, Mauro Maritano
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Patent number: 4994551Abstract: Novel, semi-crystalline depsipeptide polymers and copolymers particularly suitable for use in fabricating bioabsorbable medical implant devices such as sutures or clips and obtained through ring-opening polymerization of certain 3-substituted-2,5-morpholinediones prepared by reacting a naturally occurring alpha-amino acid with an alpha-halo acid chloride in inert solvent in the presence of an acid acceptor.Type: GrantFiled: December 21, 1989Date of Patent: February 19, 1991Assignee: Pfizer Inc.Inventors: Fu-Ning Fung, Raymond C. Glowaky
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Patent number: 4988797Abstract: Cyclic ethers having 4 and 5 member rings are polymerized with a alcohol initiator and an acid catalyst. The acid catalyst is used at a molar ratio relative to hydroxyl groups of the alcohol initiator of between about 0.05:1 and about 0.5:1.Type: GrantFiled: March 14, 1989Date of Patent: January 29, 1991Assignee: Thiokol CorporationInventors: Robert B. Wardle, Jerald C. Hinshaw
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Patent number: 4977199Abstract: Photopolymerizable compositions, based on 2-methoxytetrahydropyran and 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, which can be applied as coatings on substrates and photocured at high speeds.Type: GrantFiled: January 13, 1989Date of Patent: December 11, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Joseph V. Koleske, George T. Kwiatkowski
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Patent number: 4970295Abstract: A process for the preparation of polyethers is disclosed in which an oxetane monomer, or a mixture of an oxetane monomer and an oxolane monomer, and a carboxylic acid anhydride are contacted with a bleaching earth catalyst. The process yields ester-terminated polyethers which may be saponified to obtain hydroxy-terminated polyether polyols.Type: GrantFiled: February 27, 1989Date of Patent: November 13, 1990Assignee: ARCO Chemical Technology, Inc.Inventor: Jonathan L. Schuchardt
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Patent number: 4965342Abstract: High molecular weight (Mw>25,000, preferably >50,000; n.sub.inh up to 3) ear atactic poly (3-hydroxyoxetane) (PHO) are made by polymerizing the trimethylsilyl ether of 3-hydroxyoxetane with a coordination catalyst, or preferably with a cationic catalyst such as i-Bu.sub.3 Al-0.7 H.sub.2 O, followed by hydrolysis. The new polymer is atactic, highly crystalline, has a melting point of 155.degree. C., is devoid of measurable end groups, has a two-peak .sup.13 C-NMR, and can be readily compression molded at 200.degree. C. to a film which can be drawn at room temperature to give enhanced strength.Isotactic high molecular weight PHO (mp=223.degree. C.; .DELTA.H.sub.f =25.6 cal/g) and branched high molecular weight PHO are also prepared.Type: GrantFiled: October 10, 1989Date of Patent: October 23, 1990Assignee: Arizona Board of Regents, acting on behalf of Arizona State UniversityInventors: Edwin J. Vandenberg, Jeffrey C. Mullis
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Patent number: 4952644Abstract: ABA triblock and A.sub.n B star polymers are produced by sequential cationic polymerization of 4 and 5 member ring cyclic ethers to initially form a B block and subsequent cationic polymerization of 4 and 5 member ring cyclic ethers to form A blocks at the termini of the B block. The B block is grown from the hydroxyl groups of a polyol having two or more hydroxyl groups, resulting in a B block having terminal hydroxyl functionality of two or greater. In growing each of the B and A blocks, the acid catalyst is used at a molar ratio relative to hydroxyl groups of the polyol initiator of between about 0.05:1 and about 0.5:1.Type: GrantFiled: June 7, 1989Date of Patent: August 28, 1990Assignee: Thiokol CorporationInventors: Robert B. Wardle, Jerald C. Hinshaw, William W. Edwards
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Patent number: 4952673Abstract: A process for the purification of the polyetherdiols obtained by copolymerization of tetrahydrofuran and 1-alkene oxides by catalytic hydrogenation at temperatures up to 250.degree. C.Type: GrantFiled: August 1, 1988Date of Patent: August 28, 1990Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4933396Abstract: The present invention provides a method for making primary amine terminated linear polyethers of molecular weight above about 3500 which have virtually no contamination from in-chain secondary amine functionalities or amine-terminated tertiary amine side-chains. This method involves the production of novel intermediates.The invention also provides purely linear polyether-polyurea block copolymers formed by chain extension of the primary amine terminated linear polyethers.Type: GrantFiled: May 18, 1989Date of Patent: June 12, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Charles M. Leir, Jerome J. Hoffman, John E. Stark
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Patent number: 4916209Abstract: Novel, semi-crystalline depsipeptide polymers and copolymers particularly suitable for use in fabricating bioabsorbable medical implant devices such as sutures or clips and obtained through ring-opening polymerization of certain 3-substituted-2,5-morpholinediones prepared by reacting a naturally occurring alpha-amino acid with an alpha-halo acid chloride in inert solvent in the presence of an acid acceptor.Type: GrantFiled: December 23, 1987Date of Patent: April 10, 1990Assignee: Pfizer Inc.Inventors: Fu-Ning Fung, Raymond C. Glowaky
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Patent number: 4898923Abstract: A novel class of polymers comprises one or more dipyridinium units, having the formula ##STR1## contained within the main polymer backbone where Ar.sup.1, Ar.sup.2, and Ar.sup.3 are aromatic or heteroaromatic nuclei each of which can consist of one ring or two fused or catenated rings having 5 to 12 ring carbon and heteroatoms which can include 1 to 3 unitary heteroatoms selected from S, N, and O, R.sup.1 is any divalent organic bridging group, and Z.sup..crclbar. is a counterion.Type: GrantFiled: March 1, 1989Date of Patent: February 6, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Alan R. Katritzky, Larry R. Krepski, Jerald K. Rasmussen, Steven M. Heilmann, Richard D. Tarr
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Patent number: 4891408Abstract: Novel tetraglycidates have the formula ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, alkyl of 1 to 8 carbon atoms, perfluoroalkyl, or cycloalkylidene of 5 to 7 carbon atoms. Epoxy resin systems exhibiting good tensile properties and moisture sensitivity can be made by copolymerizing the tetraglycidates with a polyamine curing agent. Prepregs can be made by combining the epoxy resin systems with a fiber reinforcement. The epoxy resin system may include a co-epoxide.Type: GrantFiled: August 13, 1987Date of Patent: January 2, 1990Assignee: Amoco CorporationInventor: Richard H. Newman-Evans
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Patent number: 4874838Abstract: The present invention relates to copolyethers comprising copolymers of 7,oxa-bicyclo(2,2,1)heptane, and its alkyl-derivatives, with one or more cycloaliphatic ethers, comprising from 2 to 4 carbon atoms in their ring. These copolyethers show an anisotropic behavior in the molten state, and therefore have liquid-crystal properties.Type: GrantFiled: September 11, 1987Date of Patent: October 17, 1989Assignee: Montedison S.p.A.Inventors: Leonardo Fiore, Giuseppe Motroni, Mauro Maritano
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Patent number: 4841021Abstract: A novel class of polymers comprises one or more dipyridinium units, having the formula ##STR1## contained within the main polymer backbone where Ar.sup.1, Ar.sup.2, and Ar.sup.3 are aromatic or heteroaromatic nuclei each of which can consist of one ring or two fused or catenated rings having 5 to 12 ring carbon and heteroatoms which can include 1 to 3 unitary heteroatoms selected from S, N and O, R.sup.1 is any divalent organic bridging group, and Z.sup..crclbar. is a counterion.Type: GrantFiled: November 30, 1987Date of Patent: June 20, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventors: Alan R. Katritzky, Larry R. Krepski, Jerald K. Rasmussen, Steven M. Heilmann, Richard D. Tarr
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Patent number: 4837096Abstract: Polymers having repeat units represented by formula (Ia) in the main chain thereof, ##STR1## wherein Ar represents an aromatic conjugated group, and n is 10 or more, and a method of producing polymers having repeat units of general formula (I), ##STR2## wherein Ar represents an aromatic conjugated group, and X.sup.1 and X.sup.2 each represent hydrogen or halogen when the bond between the two carbon atoms is a double bond, and when the bond is a triple bond, neither X.sup.1 nor X.sup.2 exist by the electrochemical reduction of a monomer having general formula,Z.sup.1 -Ar-Z.sup.2 (II),wherein Ar is the same as that defined in the above formula (I), and Z.sup.1 and Z.sup.2 each represent a methyl halide, are disclosed. These polymers are semiconductive or electroconductive and can be used as an active material of the electrodes of organic secondary batteries.Type: GrantFiled: October 23, 1987Date of Patent: June 6, 1989Assignees: Ricoh Company, Ltd., Kunitsugu AramakiInventors: Okitoshi Kimura, Toshiyuki Ohsawa, Toshiyuki Kabata, Hiroshi Nishihara, Kunitsugu Aramaki
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Patent number: 4833213Abstract: The present invention provides a method for making primary amine terminated linear polyethers of molecular weight above about 3500 which have virtually no contamination from in-chain secondary amine functionalities or amine-terminated tertiary amine side-chains. This method involves the production of novel intermediates.The invention also provides purely linear polyether-polyurea block copolymers formed by chain extension of the primary amine terminated linear polyethers.Type: GrantFiled: June 26, 1987Date of Patent: May 23, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventors: Charles M. Leir, Jerome J. Hoffman, John E. Stark
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Patent number: 4833183Abstract: Poly[3,3-bis(hydroxymethyl)oxetane] ("PBHMO") is prepared in high molecular weight (n.sub.inh to 5.2) by polymerizing the trimethylsilylether of 3,3-bis(hydroxymethyl)oxetane with i-Bu.sub.3 Al-0.7 H.sub.2 O cationic catalyst at low temperature, followed by hydrolysis. PBHMO is crystalline, high melting (about 314.degree. C.), highly insoluble and useful in the production of films and fibers. Poly[3-methyl-3-(hydromethyl)oxetane] ("PMHMO") and poly[3-ethyl-3-(hydroxymethyl)oxetane] ("PEHMO") are also prepared in high molecular weight (n.sub.inh up to 3.8) by the same procedures. Copolymers of BHMO, MHMO, and EHMO with each other or containing up to about 50% of other oxethanes, oxiranes and tetrahydrofurans; derivatives and alloys from these polymers and copolymers; and methods of preparing the polymers, copolymers, alloys and derivatives into useful films, fibers and articles is described.Type: GrantFiled: June 3, 1988Date of Patent: May 23, 1989Assignee: Arizona Board of RegentsInventor: Edwin J. Vandenberg
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Patent number: 4808681Abstract: This invention relates to novel conductive thienylene- and furanylene-vinylene polymers and to a process for their preparation. The polymer can be formed into coherent films in which no voids are visible upto magnifications of upto 5000 times. These polymers have band gaps below 2 eV which makes them more suitable than conventional polyphenylene and poly(phenylene vinylene) polymers for use e.g. in batteries.Type: GrantFiled: February 11, 1987Date of Patent: February 28, 1989Assignee: The British Petroleum Company PLCInventors: Kevin Harper, William J. W. Watson
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Patent number: 4804424Abstract: Polyethers are formed by polymerizing oxetanes having one or two pendant groups which contain cyano moieties, particularly 3-cyanomethyl-3-methyl oxetane and 3,3-Bis(cyanomethyl) oxetane. The polyethers may also contain mer units derived from other cyclic ethers, including other oxetanes and tetrahydrofurans. The cyano group gives the polyether improved compatibility with nitrate ester plasticizers. The polyethers are curable with polyfunctional isocyanates to form binders for propellants, explosives or the like.Type: GrantFiled: June 3, 1988Date of Patent: February 14, 1989Assignee: Morton Thiokol, Inc.Inventor: Jerald C. Hinshaw
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Patent number: 4792627Abstract: A process for producing a polyether polyol with a content of 0.5 to 99.5% by weight of oxytetramethylene groups derived from tetrahydrofuran by copolymerizing tetrahydrofuran or a mixture of tetrahydrofuran and other cyclic ether copolymerizable therewith with a polyhydric alcohol having two or more hydroxyl groups per one molecule with the use of a heteropoly-acid and/or its salt as a catalyst, which comprises allowing 0.1 to 15 molecules of water per one heteropoly-anion to exist in the catalyst phase.The above-described polyether polyol is an industrially useful polymer which is a starting material for polyurethane to be used for spandex or a synthetic leather, etc.Type: GrantFiled: December 22, 1986Date of Patent: December 20, 1988Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Shoichiro Tonomura, Hiroyuki Fukui, Hisaya Imai
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Patent number: 4764567Abstract: Polyoxyalkylene block polyether polyols having enhanced physical properties are prepared by catalyzing the ethylene oxide addition with cesium hydroxide or mixtures of cesium hydroxide with other basic catalysts. These polyethers are especially useful in surface active applications.Type: GrantFiled: November 20, 1986Date of Patent: August 16, 1988Assignee: BASF CorporationInventor: Roger A. Ott
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Patent number: 4764586Abstract: Internally plasticized elastomeric binders for projectile propellants are cured polyethers containing THF, CYMMO plus BMEMO, BEEMO and/or OMMO mer units. The polyethers are fluid at room temperature and are miscible with nitrate ester plasticizers. Propellant binders prepared from these polyethers are curable, have low T.sub.g 's, good mechanical properties, and I.sub.sp 's comparable to PEG-based binders.Type: GrantFiled: October 29, 1986Date of Patent: August 16, 1988Assignee: Morton Thiokol, Inc.Inventors: Gerald E. Manser, Graham C. Shaw, III
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Patent number: 4762951Abstract: The molecular weight distribution of polytetrahydrofuran and of copolymers of tetrahydrofuran and alkylene oxides is narrowed by a process in which the polymers are mixed with a solvent mixture consisting of (a) an alkanol, (b) a hydrocarbon and (c) water, the content of the individual components a, b and c in the mixture being from 8 to 60% by weight, after which the three phases formed are separated from one another and the polymer having the narrower molecular weight distribution is isolated from the two lower phases.Type: GrantFiled: March 4, 1987Date of Patent: August 9, 1988Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4728722Abstract: A process for the batchwise preparation of polyoxybutylene polyoxyalkylene glycols by copolymerizing tetrahydrofuran with a 1,2-alkylene oxide in the presence of compounds containing reactive hydrogen, the polymerization being carried out over a bleaching earth catalyst or zeolite catalyst, and the 1,2-alkylene oxide being fed to the reaction mixture in such manner that the concentration of the 1,2-alkylene oxide in the reaction mixture is kept at below 2% by weight during the polymerization.Type: GrantFiled: February 12, 1987Date of Patent: March 1, 1988Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4707540Abstract: Nitramine oxetanes, specifically 3-methyl nitraminomethyl-3-methyl oxetane and 3,3-Bis (methyl nitraminomethyl) oxetane are synthesized. Polyethers are formed incorporating the nitramine oxetanes, which polyethers are curable with isocyanates to form elastomers suitable for use as binders in propellants or the like.Type: GrantFiled: October 29, 1986Date of Patent: November 17, 1987Assignee: Morton Thiokol, Inc.Inventors: Gerald E. Manser, Richard W. Fletcher
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Patent number: 4683249Abstract: Amidines of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are alkyl groups and the sum of the carbons in R.sub.1 and R.sub.2 is from 2 to 16 are produced by cyanoethylation of the lactam: ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, followed by reduction and, finally, cyclization by dehydration. The compounds produced are useful for curing epoxy and urethane resins.Type: GrantFiled: April 8, 1986Date of Patent: July 28, 1987Assignee: San-Apro Kabushiki KaishaInventors: Keiichi Nakatani, Shohzo Ohnishi, Tadamasa Kurosaki
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Patent number: 4683289Abstract: A novel polyaminoamide of the formula: ##STR1## wherein R.sub.m and R.sub.m ' are, the same or different, a hydrogen atom or a monovalent organic group and A.sub.m is a divalent organic group, or R.sub.m and/or R.sub.m ' form a cyclic group together with A.sub.m and the nitrogen atom to which they are bonded. m changes from 1 to p (where p is a positive integer) and n.sub.m is a positive integer, which can be prepared by reacting a 2,2,3,3-tetrafluorooxetane of the formula: ##STR2## with m kind(s) of diamine(s) of the formula: ##STR3## wherein m is the same as defined above.Type: GrantFiled: October 11, 1985Date of Patent: July 28, 1987Assignee: Daikin Industries Ltd.Inventors: Yohnosuke Ohsaka, Yoshio Amimoto, Yoshio Negishi
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Patent number: 4658065Abstract: A process for producing a polyether polyol with a content of 0.5 to 99.5% by weight of oxytetramethylene groups derived from tetrahydrofuran by copolymerizing tetrahydrofuran or a mixture of tetrahydrofuran and another cyclic ether copolymerizable therewith with a polyhydric alcohol having two or more hydroxyl groups per one molecule with the use of a heteropoly-acid and/or its salt as a catalyst, which comprises allowing 0.1 to 15 molecules of water per one heteropoly-anion to exist in the catalyst phase.The above-described polyether polyol is an industrially useful polymer which is a starting material for polyurethane to be used for spandex or a synthetic leather, etc.Type: GrantFiled: March 27, 1985Date of Patent: April 14, 1987Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Shoichiro Tonomura, Hiroyuki Fukui, Hisaya Imai
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Patent number: 4569990Abstract: The color level of poly(tetramethylene ether) glycol made by polymerizing tetrahydrofuran using fluosulfonic acid as the catalyst is significantly lower if the fluosulfonic acid contains no more than about 1200 ppm of iron sulfites.Type: GrantFiled: August 27, 1984Date of Patent: February 11, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: William W. Kasper, Willard L. Quon, Timothy D. Van Domelen
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Patent number: 4564671Abstract: Polyoxybutylene polyoxyalkylene glycols are prepared by copolymerization of tetrahydrofuran with a 1,2-alkylene oxide in the presence of a compound containing reactive hydrogen, by a continuous process in which the polymerization is carried out in a reactor over a fixed-bed clay catalyst and with recycling of the reaction mixture, and less than 30% by weight, based on the reaction mixture to be recycled, of a mixture of tetrahydrofuran, 1,2-alkylene oxide and a compound containing reactive hydrogen is added to the reaction mixture, which is recycled to the reactor after flowing through the latter.Type: GrantFiled: December 14, 1984Date of Patent: January 14, 1986Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4560779Abstract: The present invention provides a method for synthesizing a novel oxether-1 monomer by a two step reaction scheme which involves effecting a reaction between 3-methyl-3-hydroxymethyl oxetane and 1,1,1-trinitroethane to form an intermediate reaction product which in turn is reacted with methyl iodide to produce the oxether-1 monomer. The monomer is easily polymerized using conventional polymerization techniques to produce a poly(oxether-1) polyol useful as a binder component in smokeless propellants and explosives.Type: GrantFiled: July 20, 1982Date of Patent: December 24, 1985Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: John M. Guimont, Gerald E. Manser, Donald L. Ross
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Patent number: 4543374Abstract: A binder composition for foundry molds and cores comprising a furan based binder, a metal sulfonate curing catalyst therefor and a cure promoter selected from copper chloride, zinc chloride and iron chloride.Type: GrantFiled: November 8, 1984Date of Patent: September 24, 1985Assignee: QO Chemicals, Inc.Inventor: James E. Menting
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Patent number: 4500705Abstract: The oligomeric cyclic ether content of a tetrahydrofuran-, an alkylene oxide-, or a tetrahydrofuran/alkylene oxide polymerizate can be reduced by bringing the polymerizate into contact with an aliphatic- or cycloaliphatic hydrocarbon of 6-8 carbon atoms, and separating the polymerizate and the hydrocarbon phases.Type: GrantFiled: January 9, 1984Date of Patent: February 19, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harry B. Copelin
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Patent number: 4492788Abstract: Ultra-high molecular weight poly(N-propionylethylenimines) are disclosed that are useful as water purification agents. The polymers of this invention include partially deacylated poly(N-propionylethylenimines) derived from poly(N-propionylethylenimines) having a weight average molecular weight, M.sub.w, between about 1 million and about 20 million. The polymers have a degree of deacylation that ranges from about 10% to about 90%.Type: GrantFiled: January 3, 1983Date of Patent: January 8, 1985Assignee: Allied CorporationInventor: Robert S. Cooke
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Patent number: 4483978Abstract: Energetic copolymers having repeating mer units derived from different monomers, one or both of which have pendant energetic groups such as azido, nitro or nitrato groups. Copolymers have improved formulating characteristics compared to homopolymers of the energetic monomers; e.g., they are less crystalline or less viscous. Preferably the monomers are cyclic oxides having three to six atoms in the ring. The energetic monomers are preferably azido, nitro or nitrato derivatives of oxetane or THF. Copolymerization is preferably carried out by cationic polymerization using an adduct of the preinitiator precursor (e.g., 1,4-butane diol) and a catalyst suitable for cationic polymerization (e.g., boron trifluoride etherate) which is employed in stoichiometric proportion to the monomers and a low molecular weight, low polydispersity copolymer results. Certain novel monomers also are provided.Type: GrantFiled: May 18, 1982Date of Patent: November 20, 1984Assignee: S R I InternationalInventor: Gerald E. Manser
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Patent number: 4474636Abstract: In the fabrication of composite articles, a binder containing hydroxymethylfurfural is employed.Type: GrantFiled: April 29, 1983Date of Patent: October 2, 1984Assignee: QO Chemicals, Inc.Inventor: Ben R. Bogner