Polymerizing In The Presence Of A Specified Material Other Than A Reactant Patents (Class 528/408)
  • Patent number: 5726216
    Abstract: 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: Grant
    Filed: July 8, 1996
    Date of Patent: March 10, 1998
    Assignee: Lockheed Martin Energy Systems, Inc.
    Inventors: Christopher J. Janke, George F. Dorsey, Stephen J. Havens, Vincent J. Lopata
  • Patent number: 5723562
    Abstract: 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: Grant
    Filed: December 5, 1996
    Date of Patent: March 3, 1998
    Assignee: Elf Atochem North America, Inc.
    Inventor: Daryl L. Stein
  • Patent number: 5712331
    Abstract: 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: Grant
    Filed: August 15, 1995
    Date of Patent: January 27, 1998
    Assignee: Rockwell International Corporation
    Inventor: Hong-Son Ryang
  • Patent number: 5668244
    Abstract: 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: Grant
    Filed: June 16, 1995
    Date of Patent: September 16, 1997
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Miki Kawashima, Takeo Yamaguchi, Kunio Horiuchi, Hiromi Uchida
  • Patent number: 5646226
    Abstract: 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: Grant
    Filed: June 6, 1996
    Date of Patent: July 8, 1997
    Assignee: Hawaii Agriculture Research Center
    Inventors: Navzer D. Sachinala, Morton H. Litt
  • Patent number: 5620831
    Abstract: 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: Grant
    Filed: March 28, 1995
    Date of Patent: April 15, 1997
    Assignee: Taiyo Ink Manufacturing Co., Ltd.
    Inventor: Osamu Kawana
  • Patent number: 5621131
    Abstract: 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: Grant
    Filed: October 12, 1995
    Date of Patent: April 15, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Willi Kreuder, Donald Lupo, Josef Salbeck, Hermann Schenk, Thomas Stehlin
  • Patent number: 5565527
    Abstract: 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: Grant
    Filed: June 1, 1995
    Date of Patent: October 15, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Bruchmann, Roland Minges, Christian Schade, Konrad Stiefenhoefer
  • Patent number: 5552510
    Abstract: 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: Grant
    Filed: May 27, 1994
    Date of Patent: September 3, 1996
    Assignees: Centre National De La Recherche Scientifique, Hydro-Quebec
    Inventors: Jean-Yves Sanchez, Michel Armand, Jean-Pierre Petit, Yves Choquette, Glaura Goulart Silva
  • Patent number: 5545712
    Abstract: 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: Grant
    Filed: August 23, 1995
    Date of Patent: August 13, 1996
    Assignee: Mitsu Toatsu Chemicals, Inc.
    Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
  • Patent number: 5510457
    Abstract: 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: Grant
    Filed: April 24, 1995
    Date of Patent: April 23, 1996
    Assignee: National Science Council
    Inventors: Show-An Chen, Chin-Chang Lee
  • Patent number: 5508379
    Abstract: 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: Grant
    Filed: December 21, 1994
    Date of Patent: April 16, 1996
    Assignee: BASF Corporation
    Inventors: Gregory L. Menovcik, Walter H. Ohrbom
  • Patent number: 5492996
    Abstract: 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: Grant
    Filed: February 21, 1995
    Date of Patent: February 20, 1996
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Thuy D. Dang, Jom P. Chen, Fred E. Arnold
  • Patent number: 5493005
    Abstract: 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: Grant
    Filed: February 21, 1995
    Date of Patent: February 20, 1996
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Fred E. Arnold, Jom P. Chen
  • Patent number: 5483008
    Abstract: 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: Grant
    Filed: February 5, 1993
    Date of Patent: January 9, 1996
    Assignee: Research Development Corporation of Japan
    Inventors: Yasuhisa Sakurai, Teruo Okano, Masayuki Yokoyama, Kazunori Kataoka, Yukio Nagasaki, Nobuyuki Ohsako, Masao Kato
  • Patent number: 5468841
    Abstract: 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: Grant
    Filed: April 13, 1994
    Date of Patent: November 21, 1995
    Assignee: Aerojet General Corporation
    Inventors: Aslam A. Malik, Thomas G. Archibald, Roland P. Carlson, Gerald E. Manser
  • Patent number: 5468840
    Abstract: 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: Grant
    Filed: August 29, 1994
    Date of Patent: November 21, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
  • Patent number: 5463020
    Abstract: 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: Grant
    Filed: June 30, 1994
    Date of Patent: October 31, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Michael Huellmann, Christof Palm, Wolfgang Franzischka
  • Patent number: 5462698
    Abstract: 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: Grant
    Filed: March 31, 1994
    Date of Patent: October 31, 1995
    Assignee: Tokuyama Corporation
    Inventors: Takashi Kobayakawa, Satoshi Imura, Kazumasa Itonaga, Kazuhiko Kuramoto
  • Patent number: 5453468
    Abstract: 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: Grant
    Filed: January 24, 1995
    Date of Patent: September 26, 1995
    Assignee: Ausimont S.p.A.
    Inventors: Leno Mascia, Claudio Tonelli, Giovanni Simeone
  • Patent number: 5447797
    Abstract: 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: Grant
    Filed: August 9, 1993
    Date of Patent: September 5, 1995
    Assignee: Siemens Aktiengesellschaft
    Inventors: Bernhard Stapp, Lothar Schoen, Volker Muhrer
  • Patent number: 5444105
    Abstract: 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: Grant
    Filed: July 30, 1993
    Date of Patent: August 22, 1995
    Assignee: Mount Sinai School of Medicine of the City University of New York
    Inventor: Leonard Ornstein
  • Patent number: 5442035
    Abstract: 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: Grant
    Filed: September 29, 1993
    Date of Patent: August 15, 1995
    Assignee: Shell Oil Company
    Inventors: Larry S. Corley, Harold E. De La Mare
  • Patent number: 5393866
    Abstract: 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: Grant
    Filed: November 10, 1993
    Date of Patent: February 28, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Nobuyuki Murai, Masayuki Shirato, Hiroshi Takeo, Hidetoshi Tanaka
  • Patent number: 5391681
    Abstract: 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: Grant
    Filed: May 27, 1993
    Date of Patent: February 21, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Muhlebach, Peter Flury
  • Patent number: 5374697
    Abstract: 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: Grant
    Filed: July 14, 1993
    Date of Patent: December 20, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Beat Muller
  • Patent number: 5344964
    Abstract: 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: Grant
    Filed: November 24, 1993
    Date of Patent: September 6, 1994
    Assignee: Industrial Technology Research Institute
    Inventors: Shiao-Jung Chu, Fu-Chen Liu, Ching-Tang Lin, Wen-Fa Lin, Kuei-Chih Wang, Sheng-Te Yang
  • Patent number: 5338828
    Abstract: Novel cyclic imino ether compositions containing one or more mesogenic moieties, when polymerized, result in products having improved properties.
    Type: Grant
    Filed: September 10, 1993
    Date of Patent: August 16, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5336745
    Abstract: 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: Grant
    Filed: May 16, 1991
    Date of Patent: August 9, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Herve M. Cheradame, Robert D. Lundberg, Frank J. Chen, Jean de la Crois Habimana
  • Patent number: 5319068
    Abstract: 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: Grant
    Filed: February 3, 1992
    Date of Patent: June 7, 1994
    Assignee: Olin Corporation
    Inventors: Roger W. Day, Rahim Hani
  • Patent number: 5313000
    Abstract: 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: Grant
    Filed: January 27, 1992
    Date of Patent: May 17, 1994
    Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the U.K. of Britain and Northern Ireland
    Inventor: Malcolm J. Stewart
  • Patent number: 5302695
    Abstract: 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: Grant
    Filed: September 10, 1993
    Date of Patent: April 12, 1994
    Assignee: Shell Oil Company
    Inventors: Harry Frank, George C. Blytas, Anne H. Zuzich
  • Patent number: 5296567
    Abstract: 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: Grant
    Filed: April 6, 1992
    Date of Patent: March 22, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Baumann, Werner Margotte, Beat Muller
  • Patent number: 5294582
    Abstract: 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: Grant
    Filed: June 14, 1993
    Date of Patent: March 15, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Tadafumi Miyazono, Koji Tabuchi
  • Patent number: 5280069
    Abstract: The new compound N,N,N'N'-tetraglycidyl-3,3'-diethyl-4,4'-diaminodiphenylmethane and curable resin compositions containing it.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: January 18, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Bryan Dobinson, Michael R. Thoseby
  • Patent number: 5278247
    Abstract: 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: Grant
    Filed: April 24, 1992
    Date of Patent: January 11, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Tadafumi Miyazono, Koji Tabuchi
  • Patent number: 5264596
    Abstract: 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: Grant
    Filed: August 13, 1992
    Date of Patent: November 23, 1993
    Assignee: Thiokol Corporation
    Inventors: Rodney L. Willer, Alfred G. Stern, Robert S. Day
  • Patent number: 5254664
    Abstract: 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: Grant
    Filed: December 31, 1991
    Date of Patent: October 19, 1993
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Subhash C. Narang, Asutosh Nigam, Apparao Satyam, Susanna C. Ventura, Yoshihiro Arita
  • Patent number: 5239042
    Abstract: 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: Grant
    Filed: November 15, 1991
    Date of Patent: August 24, 1993
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Isaburo Fukawa, Tsuneaki Tanabe
  • Patent number: 5219981
    Abstract: 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: Grant
    Filed: March 1, 1991
    Date of Patent: June 15, 1993
    Assignee: The Dow Chemical Company
    Inventors: Thomas Gregory, Carl W. Hurtig, Harvey D. Ledbetter, Kenneth J. Quackenbush, Steven Rosenberg
  • Patent number: 5218141
    Abstract: 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: Grant
    Filed: November 6, 1991
    Date of Patent: June 8, 1993
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 5216122
    Abstract: 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: Grant
    Filed: May 21, 1991
    Date of Patent: June 1, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Walter T. Reichle, Geoffrey A. D'Netto, Guy M. Troy, Meyer R. Rosen, Elke M. A. Clark
  • Patent number: 5210179
    Abstract: 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: Grant
    Filed: January 28, 1992
    Date of Patent: May 11, 1993
    Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventor: Malcolm J. Stewart
  • Patent number: 5210153
    Abstract: 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: Grant
    Filed: January 6, 1992
    Date of Patent: May 11, 1993
    Inventors: Gerald E. Manser, Richard S. Miller
  • Patent number: 5196259
    Abstract: 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: Grant
    Filed: December 7, 1990
    Date of Patent: March 23, 1993
    Assignee: The Dow Chemical Company
    Inventors: Peter E. Pierini, Ritchie A. Wessling, Peter K. Kim
  • Patent number: 5164477
    Abstract: 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: Grant
    Filed: August 2, 1991
    Date of Patent: November 17, 1992
    Assignee: Shiro Kobayashi
    Inventors: Shiro Kobayashi, Hiroshi Uyama
  • Patent number: 5162494
    Abstract: 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: Grant
    Filed: November 5, 1990
    Date of Patent: November 10, 1992
    Assignee: Thiokol Corporation
    Inventors: Rodney L. Willer, Alfred G. Stern, Robert S. Day
  • Patent number: 5149767
    Abstract: 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: Grant
    Filed: October 11, 1990
    Date of Patent: September 22, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Munk, Martin Roth
  • Patent number: 5132377
    Abstract: 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: Grant
    Filed: June 4, 1990
    Date of Patent: July 21, 1992
    Assignee: Nippon Paint Company, Limited
    Inventors: Shinji Nakano, Satoshi Urano
  • Patent number: 5130413
    Abstract: 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: Grant
    Filed: August 30, 1990
    Date of Patent: July 14, 1992
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yukimitsu Asai, deceased, by Keiji Asai, legal representative, by Yoshie Asai, legal representative, Hiroyuki Kawata, Tooru Nakagawa