Material Contains A Group Iiia Metal Atom (al, Ga, In, Tl) Patents (Class 528/416)
  • Patent number: 9040657
    Abstract: Alkylene oxide polymerizations are performed in the presence of a double metal cyanide polymerization catalyst and certain magnesium, Group 3-Group 15 metal or lanthanide series metal compounds. The presence of the magnesium, Group 3-Group 15 metal or lanthanide series metal compound provides several benefits including more rapid catalyst activation, faster polymerization rates and the reduction in the amount of ultra high molecular weight polymers that are formed. The catalyst mixture is unexpectedly useful in making polyethers having low equivalent weights.
    Type: Grant
    Filed: December 18, 2011
    Date of Patent: May 26, 2015
    Assignee: Dow Global Technologies LLC
    Inventors: David S. Laitar, David A. Babb, Carlos M. Villa, Richard Keaton, Jean-Paul Masy
  • Patent number: 8703898
    Abstract: A hyperbranched polyether polyol obtained by a ring-opening reaction between a hydroxyalkyloxetane (a1) and a monofunctional epoxy compound (a2), wherein the polyether polyol includes a primary hydroxyl group (H1) and a secondary hydroxyl group (H2) in the molecular structure thereof, and has a number average molecular weight (Mn) of 1,000 to 4,000 and a hydroxyl value of 150 to 350 mg·KOH/g.
    Type: Grant
    Filed: June 20, 2006
    Date of Patent: April 22, 2014
    Assignee: DIC Corporation
    Inventors: Rainer B. Frings, Toshihiro Ooki, Yasuhiro Takada, Hitoshi Hayakawa
  • Patent number: 8609193
    Abstract: A method for ionic polymerization of ethylene oxide. In the first step of the method, a gaseous monomer composition comprising ethylene oxide at a first flow rate is mixed with a gaseous ionic polymerization initiator at a second flow rate, thereby forming a mixture. The formed mixture is then heated with at least one heated filament to thereby form at least one polymer. The method may also be employed to coat a variety of different substrates in situ during the polymerization reaction.
    Type: Grant
    Filed: March 17, 2010
    Date of Patent: December 17, 2013
    Assignee: Drexel University
    Inventors: Kenneth K. S. Lau, Ranjita K. Bose
  • Patent number: 8609805
    Abstract: The present invention provides a highly efficient process for manufacturing copolyether glycol having a mean molecular weight of from about 650 to about 5000 dalton by polymerization of tetrahydrofuran and at least one alkylene oxide in the presence of an acid catalyst and at least one compound containing reactive hydrogen atoms. More particularly, the invention relates to a process for manufacturing copolyether glycol which comprises recycle to the polymerization reaction step of at least a portion of the oligomeric cyclic ether which is co-produced with the copolyether glycol, said process exhibiting an Space Time Yield value of greater than about 0.9.
    Type: Grant
    Filed: September 28, 2011
    Date of Patent: December 17, 2013
    Assignee: Invista North America S.A R.L.
    Inventors: Qun Sun, Gary L. Kiser, Robert D. Orlandi
  • Patent number: 8455590
    Abstract: It is an object to provide a film having both high transparency and high heat resistance, and particularly a coating solution for forming a coating film from which an optical film can be produced. A triaroylbenzene-skeleton polymer in which a terminal of a polymer produced by polymerizing a compound of Formula [1] below is modified by a compound of Formula [2] below. A coating solution for forming a coating film, comprising the polymer. A film obtained from the coating solution for forming a coating film. In the formulae below, X1 is a divalent group of Formula [1a], Formula [1b], or Formula [1c] below (where Y1 and Y2 are independently a C1-2 alkylene group; n is an integer of 1 to 6; and m is an integer of 1 to 6), X2 is divalent benzene, thiophene, furan, or fluorine, and X3 is a hydrogen atom, a halogen atom, CF3, a C1-6 alkoxy group, or a C1-6 alkyl group.
    Type: Grant
    Filed: October 2, 2009
    Date of Patent: June 4, 2013
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Takuro Oda
  • Patent number: 8450450
    Abstract: The present invention relates to an improved process for manufacturing polyether and copolyether glycols by polymerization of a reaction mixture comprising at least one tetrahydrofuran or at least one tetrahydrofuran and at least one other cyclic ether, for example, an alkylene oxide, in the presence of a particular perfluorosulfonic acid resin catalyst comprising a copolymer of tetrafluoroethylene (TFE) or chlorotrifluoroethylene (CTFE) and a monomer of the formula CF2?CF—O—CF2—CF2—SO2F.
    Type: Grant
    Filed: August 19, 2010
    Date of Patent: May 28, 2013
    Assignee: Invista North America S.A R.L.
    Inventor: Qun Sun
  • Patent number: 8436133
    Abstract: The present invention relates to the use of group 3 post-metallocene complexes based on sterically encumbered bis(naphthoxy)pyridine and bis(naphthoxy)thiophene ligands in the ring-opening polymerisation of polar monomers such as, for examples, lactones, lactides, cyclic carbonates.
    Type: Grant
    Filed: February 17, 2009
    Date of Patent: May 7, 2013
    Assignees: Total Petrochemicals Research Feluy, Centre National de la Recherche Scientifique (CNRS)
    Inventors: Jean-François Carpentier, Evgueni Kirillov, Abbas Razavi
  • Patent number: 8372946
    Abstract: The present invention relates to a continuous process for manufacturing copolyether glycols with high incorporation of alkylene oxide by polymerization of tetrahydrofuran and at least one alkylene oxide in the presence of an acid catalyst, at least one compound containing reactive hydrogen atoms, and a specific diluent or solvent. More particularly, the invention relates to a diluent or solvent-assisted continuous process for manufacturing copolyether glycols with high incorporation of alkylene oxide.
    Type: Grant
    Filed: April 15, 2009
    Date of Patent: February 12, 2013
    Assignee: Invista North America S.A R.L.
    Inventors: Qun Sun, Robert D. Orlandi
  • Publication number: 20110318646
    Abstract: The present invention is directed at a binder for a battery electrode comprising an ethylene oxide-containing copolymer including a first monomer of ethylene oxide (EO) and at least one additional monomer selected from an alkylene-oxide that is different from the first monomer of EO, an alkyl glycidyl ether, or a combination thereof; wherein the ethylene oxide-containing copolymer has a weight average molecular weight less than about 200,000 g/mole (e.g., from about 10,000 to about 100,000), the molar fraction of the first monomer of EO (XEo) in the ethylene oxide-containing copolymer is greater than 0.80 (e.g., from about 0.80 to about 0.995), and the ethylene oxide-containing copolymer h a peak melting temperature (Tp), in ° C., for a selected XEO in the range of about 0.80 to about 0.995, which is below a maximum value of Tpmax, at the selected XEO, which is calculated using the equation Tpmax=(60?150 (1?XEO)).
    Type: Application
    Filed: February 10, 2010
    Publication date: December 29, 2011
    Applicant: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Susan J. Babinec, Houxiang Tang, Abhijit Ghosh-Dastidar, Eric P. Wasserman, Richard A. Galley, Michael M. Luong
  • Publication number: 20110305837
    Abstract: A method for ionic polymerization of ethylene oxide. In the first step of the method, a gaseous monomer composition comprising ethylene oxide at a first flow rate is mixed with a gaseous ionic polymerization initiator at a second flow rate, thereby forming a mixture. The formed mixture is then heated with at least one heated filament to thereby form at least one polymer. The method may also be employed to coat a variety of different substrates in situ during the polymerization reaction.
    Type: Application
    Filed: March 17, 2010
    Publication date: December 15, 2011
    Applicant: DREXEL UNIVERSITY
    Inventors: Kenneth K.S. Lau, Ranjita K. Bose
  • Publication number: 20100190955
    Abstract: A catalyst composition for polymerizing oxiranes is provided that yields high molecular weight poly(oxiranes). The catalyst composition comprises: a hydrophobically modified particulate inorganic oxide; an aluminum alkyl complex; and a compound containing a Lewis basic free electron pair. Polymerization methods and poly(oxirane) polymers are also provided.
    Type: Application
    Filed: September 6, 2007
    Publication date: July 29, 2010
    Applicant: DOW GLOBAL TECHNOLOGIES INC.
    Inventors: Eric P. Wasserman, Richard A. Galley, Woo Min Song, Abhijit Ghosh-Dastidar
  • Publication number: 20090299032
    Abstract: A catalyst, co-catalyst, and/or chain transfer agent is added at a time after initiation of an addition polymerization reaction to produce a polymer product with a widened molecular weight distribution relative to having all of the components in the original reaction mixture. The catalyst, co-catalyst, or chain transfer agent may be added discretely or continuously to the reaction to produce a product with a bimodal, trimodal, or other broadened molecular weight distribution.
    Type: Application
    Filed: May 29, 2008
    Publication date: December 3, 2009
    Applicant: NOVOMER INC.
    Inventor: Scott D. Allen
  • Publication number: 20090215971
    Abstract: The present invention relates to a process for preparing polytetrahydrofuran or tetrahydrofuran copolymers by polymerization of tetrahydrofuran in the presence of a telogen and/or a comonomer over a fixed bed of an acid catalyst, in which the temperature of the polymerization mixture increases in the direction of flow through the catalyst bed.
    Type: Application
    Filed: May 25, 2007
    Publication date: August 27, 2009
    Applicant: BASF SE
    Inventors: Tobias Wabnitz, Stephan Hatscher, Stefan Käshammer, Rolf Pinkos
  • Patent number: 7488772
    Abstract: Mixtures or adducts of N-heterocyclic carbenes with metal amides or metal alkoxides are effective catalysts for the polymerization of macrocyclic polyester oligomers. The catalysts are stable at polymerization temperatures, and the polymerization is rapid, resulting in high monomer conversion, high molecular weight, and a mechanically sound material.
    Type: Grant
    Filed: November 9, 2005
    Date of Patent: February 10, 2009
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Wilson Tam, David T. Williamson
  • Patent number: 7456249
    Abstract: The present invention relates to a solid, acid catalyst for the preparation of polytetrahydrofuran, polytetrahydrofuran copolymers, diesters or monoesters of these polymers by polymerization of tetrahydrofuran in the presence of at least one telogen and/or comonomer, which has a BET surface area of at least 160 m2/g and an acid center density of at least 0.05 mmol/g for pKa values of from 1 to 6, to a process for preparing it and to a process for the polymerization of cyclic ethers over this catalyst.
    Type: Grant
    Filed: January 10, 2008
    Date of Patent: November 25, 2008
    Assignee: BASF SE
    Inventors: Stephan Schlitter, Martin Haubner, Michael Hesse, Stefan Kaeshammer, Rolf Pinkos, Christoph Sigwart
  • Patent number: 7417075
    Abstract: A cationically polymerizable composition containing a cationically polymerizable compound and a cationic polymerization initiator, wherein a total content of a cationic compound, a metal compound and a strong acid compound contained in the cationically polymerizable composition is in the range of 1 to 500 ppm by weight based on the total weight of the cationically polymerizable composition.
    Type: Grant
    Filed: August 22, 2005
    Date of Patent: August 26, 2008
    Assignee: Konica Minolta Medical & Graphic, Inc.
    Inventor: Nobumasa Sasa
  • Patent number: 7368524
    Abstract: The invention relates to two-component preparations comprising epoxy compounds and a noble metal species, in particular for the preparation of dental compositions. The invention particularly relates to two-component dental compositions which comprise epoxy compounds and are cured by cationic polymerization in the presence of a noble metal species.
    Type: Grant
    Filed: April 19, 2005
    Date of Patent: May 6, 2008
    Assignee: 3M Innovative Properties Company
    Inventors: Adrian S. Eckert, Uwe H. Hoheisel, Reinhold Hecht
  • Patent number: 7034103
    Abstract: The present invention provides process for producing polyols using a crystalline, hydroxide containing double metal cyanide (DMC) catalyst of the formulae (I) or (II), M1x[M2(CN)6]yOH.L??(I) M1x[M2(CN)6]y.zM1(OH)q.L??(II) wherein M1 represents a metal selected from Zn+2, Fe+2, Ni+2, Mn+2, Co+2, Sn+2, Pb+2, Fe+3, Mo+4, Mo+6, Al+3, V+4, V+5, Sr+2, W+4, W+6, Cu+2 and Cr+3, M2 represents a metal selected from Fe+2, Fe+3, Co+2, Co+3, Cr+2, Cr+3, Mn+2, Mn+3, Ir+3, Ni+2, Rh+3, Ru+2, V+4 and V+5, L represents an organic ligand and x, y and q are chosen to maintain electroneutrality. The polyols of the present invention may find use in the preparation of polyurethanes.
    Type: Grant
    Filed: January 5, 2005
    Date of Patent: April 25, 2006
    Assignee: Bayer Antwerpen N.V.
    Inventor: George G. Combs
  • Patent number: 6830704
    Abstract: A 2-cyanoacrylate composition useful as an adhesive contains a Lewis acid metal salt comprising a metal such as aluminum, gallium, indium or thalium, and the conjugate base of an acid such as a monohalo-, dihalo- or trihalo-acetate (e.g. aluminum trifluoroacetate salt). A clathrate such as a crown ether is also present.
    Type: Grant
    Filed: February 28, 2003
    Date of Patent: December 14, 2004
    Assignee: Toagosei Co., Ltd.
    Inventors: Seitaro Tajima, Mitsuyoshi Sato
  • Patent number: 6815529
    Abstract: This invention relates to a catalyst for producing aliphatic polycarbonate, which is composed of a rare-earth coordination compound; an alkyl metal compound; a polyol; and a carbonate. The catalytic efficiency of the catalyst of the present invention is more than 8×104 g polymer/mol RE(RE is rare earth metal). The number average molecular weight of the polymer is higher than 30,000. The degree of carbon dioxide fixation is more than 42 wt % and the content of alternative sequence structure exceeds 97%.
    Type: Grant
    Filed: August 29, 2001
    Date of Patent: November 9, 2004
    Assignee: Changchun Institute of Applied Chemistry Chinese Academy of Sciences
    Inventors: Xiaojiang Zhao, Xianhong Wang, Fosong Wang
  • Patent number: 6794451
    Abstract: A cationically polymerizable liquid composition is formed from a cationically polymerizable mixture (A) and a solid resin (B) that is compatible with the mixture (A) at room temperature and has a softening point of at least 40° C., so that the composition has a viscosity at 25° C. of 20 Pa·sec or below. The cationically polymerizable mixture (A) is formed from a monofunctional monomer (A-1) having in the molecule only one cyclic ether structure represented by formula (1) below, a polyfunctional monomer (A-2) having in the molecule at least two cyclic ether structures represented by formula (1) below, and a latent cationic polymerization initiator (A-3). A tacky polymer formed by cationic polymerization of the composition is also disclosed. (In formula (1), n denotes 0, 1, or 2, and R1 to R6 independently denote hydrogen atoms or hydrocarbon groups, which may have a substituent.
    Type: Grant
    Filed: February 12, 2002
    Date of Patent: September 21, 2004
    Assignee: Toagosei Co., Ltd.
    Inventors: Hiroshi Sasaki, Koutarou Yoneda
  • Patent number: 6632897
    Abstract: Described is the use of nanoscale metal oxide particles as catalysts for the thermal and/or photochemical polymerization of species having at least one polymerizable carbon-carbon multiple bond and/or at least one carbon containing ring capable of undergoing a ring opening polymerization.
    Type: Grant
    Filed: December 20, 1999
    Date of Patent: October 14, 2003
    Assignee: Institut Für Neue Materialien gemeinnützige
    Inventors: Elisabeth Geiter, Helmut Schmidt
  • Patent number: 6586564
    Abstract: The invention relates to double-metal cyanide (DMC) catalysts for preparing polyether polyols by the polyaddition of alkylene oxides on to starter compounds containing active hydrogen atoms, wherein the DMC catalysts are composed of: a) at least one DMC compound; b) at least one organic complexing ligand which is not a coronand; and c) at least one coronand. The DMC catalysts of the present invention have increased activity compared to known catalysts.
    Type: Grant
    Filed: August 28, 2002
    Date of Patent: July 1, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Schäfer, Jörg Hofmann, Pieter Ooms
  • Patent number: 6569981
    Abstract: This invention relates to crystallizing polyether polyols which can be produced firstly by the reaction of propylene oxide and polyhydroxy compounds in the presence of an alkoxy compound which contains zinc and/or aluminium atoms to form a crystallizing polyether polyol with an average molecular weight Mn from 500 to 5000, followed by the further reaction of the crystallizing polyether polyol which is thus obtained with 10 to 90% by weight, with respect to the amount of crystallizing polyol, of an epoxide in the presence of a catalyst which does not polymerize propylene oxide stereospecifically, to form a crystallizing polyether polyol with an average molecular weight Mn from 1000 to 20,000. The invention further relates to a method for the production thereof and to the use thereof for the production of polyurethane materials, particularly polyurethane foams, polyurethane elastomers and polyurethane coatings.
    Type: Grant
    Filed: October 25, 2001
    Date of Patent: May 27, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Schäfer, Jörg Hofmann, Pramod Gupta, Pieter Ooms
  • Patent number: 6547985
    Abstract: A 2-cyanoacrylate composition useful as an adhesive contains a Lewis acid metal salt which comprises a specific metal such as aluminum, gallium, indium or thallium, and the conjugate base of an acid having oxygen such as a monohalo-, dihalo or trihaloacetate, wherein the metal is bonded to the conjugate base through an oxygen atom, and a compound having clathrating ability such as a crown ether.
    Type: Grant
    Filed: April 7, 2000
    Date of Patent: April 15, 2003
    Assignee: Togosei Co., Ltd.
    Inventors: Seitaro Tajima, Mitsuyoshi Sato
  • Patent number: 6512074
    Abstract: Polymerization catalysts of oxirane compounds are catalysts which are suitable to carry out suspension precipitation polymerization of the oxirane compounds in an organic solvent which cannot dissolve the polymers and comprise a reaction product of (A) an alkylaluminum compound, (B) an oxoacid compound of phosphorus having at least one OH group in its molecule and (C) a nitrogen-containing cyclic compound having pKa of 6 to 8. A process for preparing the polymers of the oxirane compounds is a process wherein the monomeric oxirane compounds are subjected to the suspension precipitation polymerization in the organic solvent which cannot dissolve the polymers in the presence of the catalysts to prepare the polymers of the oxirane compounds.
    Type: Grant
    Filed: June 27, 2001
    Date of Patent: January 28, 2003
    Assignee: Daiso Co., Ltd.
    Inventors: Shigeru Shoji, Yasumi Shimizu, Katsuhito Miura
  • Patent number: 6458918
    Abstract: The present invention relates to a process for the preparation of novel, partially crystalline polyether polyols with a functionality of ≧2, an average molecular weight Mn of 500 to 100,000 and a molar proportion of isotactic triads determining the crystallinity of >28%. The new polyether polyols are prepared by polymerizing alkylene oxides in the presence of a bimetallic :-oxoalkoxide modified with hydroxyl compounds.
    Type: Grant
    Filed: April 27, 2000
    Date of Patent: October 1, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Schäfer, Jörg Hofmann, Pramod Gupta, Hanns-Peter Müller, Harald Pielartzik
  • Patent number: 6437090
    Abstract: A curing catalyst comprising at least one of a cationic curing catalyst component and an organo-metallic compound component. At least one of these components is capable of reversibly repeating the dissolution and precipitation through heating and cooling. The cationic curing catalyst component includes in its molecule at least one substituted or unsubstituted hydrocarbon group having 10 or more carbon atoms, or at least one cyclic organic structure having a substituted or unsubstituted hydrocarbon group having 10 or more carbon atoms.
    Type: Grant
    Filed: June 17, 1999
    Date of Patent: August 20, 2002
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shinji Murai, Shuji Hayase, Shinetsu Fujieda, Rumiko Hayase, Yasuyuki Hotta
  • Patent number: 6403842
    Abstract: Disclosed are a process for producing a poly(alkylene ether) glycol which comprises polymerizing a cyclic ether in the presence of at least a catalyst and a carboxylic acid anhydride, wherein the carboxylic acid anhydride has a ketene dimer content of 50 ppm or lower, and a process for producing a poly(alkylene ether) glycol which comprises polymerizing a cyclic ether in the presence of at least a catalyst and acetic anhydride, wherein the acetic anhydride is purified acetic anhydride obtained by treating acetic anhydride by contacting with at least one of a metal oxide and a mixed oxide, and optionally, distilling the acetic anhydride simultaneously with or after the contact treatment.
    Type: Grant
    Filed: January 13, 2000
    Date of Patent: June 11, 2002
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Mitsuharu Kobayashi, Nobuyuki Murai
  • Patent number: 6359108
    Abstract: A process for polymerizing cyclic ethers over a heterogeneous catalyst comprises using a heterogeneous catalyst comprising one or more pillared interlayered clays (PILCs).
    Type: Grant
    Filed: November 9, 1999
    Date of Patent: March 19, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Karsten Eller, Frank Stein, Christoph Sigwart, Rainer Becker, Klaus-Dieter Plitzko, Rolf Fischer, Ulrich Müller
  • Patent number: 6281154
    Abstract: Novel compounds having one group 13 element bound with one mono- or di-anionic tridentate ligand, a method of preparation thereof and use thereof as a copolymerization catalyst.
    Type: Grant
    Filed: October 28, 1998
    Date of Patent: August 28, 2001
    Assignees: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S), Centre National de la Recherche Scientifique (CNRS)
    Inventors: Guy Bertrand, Jean Bernard Cazaux, Norbert Emig, Régis Reau
  • Patent number: 6207793
    Abstract: An improved process for Polytetramethylene-Ether-Glycol-Diesters of the formula R—CO—O(CH2—CH2—CH2—CH2—O)n-COR1, in which R and R1 are identical or different and are alkyl radicals or derivatives thereof, by polymerization of tetrahydrofuran in the presence of a heterogeneous polymerization catalyst and in the presence of a carboxylic anhydride. The use of aluminum silicate catalyst composed of acid-activated and calcinated natural halloysite instead of the known catalytic silicates as bentonite, zeolite or kaolinite. The new catalyst with a very long lifetime produces polymers having more uniform properties and narrow molecular weight distribution even with a relative impure monomer.
    Type: Grant
    Filed: July 15, 1999
    Date of Patent: March 27, 2001
    Assignee: Korea PTG Co., Ltd.
    Inventor: Sung-Il Kim
  • Patent number: 6096836
    Abstract: Disclosed herein is a curing catalyst comprising at least one compound which is a substituted or unsubstituted aromatic or heteroaromatic compound and having any one of groups (I) --O--R.sub.1, (II) --O--CY--R.sub.1, or (III) --O--CY--X--R.sub.1, the groups being directly bonded to the armoatic or heteroaromatic ring, in a number of 1 to 10 wherein R.sub.1 may be the same or different and is a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, X is O or NH and Y is O or S. Furthermore, an epoxy resin composition comprising the curing catalyst is disclosed.
    Type: Grant
    Filed: March 2, 1998
    Date of Patent: August 1, 2000
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shuzi Hayase, Yoshihiko Nakano, Shinji Murai, Yukihiro Mikogami
  • Patent number: 6015914
    Abstract: Provided is a compound having an oxetanyl group and represented by the following formula: ##STR1## wherein R.sub.1 represents a methyl group or an ethyl group and R.sub.2 represents a hydrogen atom, a halogen atom, a straight or branched chain alkyl group of 1-5 carbon atoms, an unsubstituted or substituted phenyl group, an unsubstituted or substituted phenoxymethyl group, an unsubstituted or substituted phenoxypropyl group or an unsubstituted or substituted phenyl group. A process for producing the compound and a curing composition comprising the compound and a cationic polymerization initiator are also provided.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: January 18, 2000
    Assignee: Toagosei, Co., Ltd.
    Inventors: Hiroshi Sasaki, Akira Kuriyama
  • Patent number: 5969059
    Abstract: An impregnation resin composition comprising an alicyclic epoxy compound, an acid anhydride, an aluminum compound having an organic group, and butylglycidyl ether, wherein the alicyclic epoxy compound contains not more than 30 ppm in concentration of Na ion component.
    Type: Grant
    Filed: March 13, 1998
    Date of Patent: October 19, 1999
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shinji Murai, Shuji Hayase
  • Patent number: 5952458
    Abstract: Synthesis of a vinyl terminated polymer by reacting a cationically polymerizable monomer in the form of a cyclic ether with an acid chloride in a suitable solvent and in the presence of a Lewis acid. The vinyl-terminated polymers can be polymerized with other appropriate monomers resulting in thermoplastic elastomers having suitable properties for use as binders for explosives and propellants.
    Type: Grant
    Filed: September 24, 1998
    Date of Patent: September 14, 1999
    Assignee: The Government of the United States as represented by the Secretary of the Navy
    Inventor: Mostafa A. H. Talukder
  • Patent number: 5942595
    Abstract: Disclosed is a process for copolymerization of formaldehyde with cyclic ethers in the presence of organic nitro compounds. The process enhances the selectivity for the cyclic copolymer.
    Type: Grant
    Filed: July 13, 1998
    Date of Patent: August 24, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Douglas John Adelman, Richard Beckerbauer
  • Patent number: 5922633
    Abstract: A thermal latent acid catalyst which comprises (i) a compound having an epoxy group, (ii) a compound having a sulfur atom of the following formula: R.sup.5 --S--R.sup.6, wherein R.sup.5 and R.sup.6 are the same or different from each other and are a hydrogen atom or an organic group of 1 to 40 carbon atoms, R.sup.5 and R.sup.6 optionally are bonded with each other to form a cyclic structure; and (iii) a Lewis acid of the following formula: (X.sup.1).sub.n1 --M.sup.1 --(R.sup.7).sub.n2, wherein M.sup.1 is a boron atom, an aluminium atom, a tin atom, a lead atom or a transition element, X.sup.1 is one or more halogen atoms, R.sup.7 is one or more organic groups of 1 to 40 carbon atoms, R.sup.7 optionally forms a chelate ring by coordinating to the M.sup.1 atom, n1 and n2 are each an integer of 0 through 6, and n1 plus n2 equals an integer of 1 to 6. The ratio of the epoxy group of the epoxy compound (i) to the M.sup.1 atom of the Lewis acid is 0.
    Type: Grant
    Filed: April 18, 1997
    Date of Patent: July 13, 1999
    Assignee: NOF Corporation
    Inventors: Yoshinori Nakane, Hiroki Mizutani, Hayato Ishibashi, Masahiro Ishidoya
  • Patent number: 5886138
    Abstract: A process for the continuous and discontinuous production of tetrahydrofuran polymers by homopolymerizing tetrahydrofuran or copolymerizing tetrahydrofuran with 1,2-alkylene oxides in the presence of compounds with reactive hydrogen or carboxylic acid anhydrides on an acid-treated, calcined and granulated aluminium silicate catalyst which may consist of amorphous aluminium silicate, a zeolite or kaolin. By keeping the concentration of carboxylic acid anhydride or alkylene oxide constant below 1 wt. % in the polymerization recipe throughout the polymerization it is possible to largely prevent the formation of cyclic ethers and to obtain a polymer with a very narrow molecular weight distribution. In granular form, the catalysts exhibit a hitherto unknown activity and form polymers with a very narrow molecular weight distribution and low color and acid numbers.
    Type: Grant
    Filed: July 30, 1997
    Date of Patent: March 23, 1999
    Inventor: Herbert Muller
  • Patent number: 5811497
    Abstract: Disclosed herein is a curing catalyst comprising at least one compound which is a substituted or unsubstituted aromatic or heteroaromatic compound and having any one of groups (I) --O--R.sub.1, (II) --O--CY--R.sub.1, or (III) --O--CY--X--R.sub.1, the groups being directly bonded to the armoatic or heteroaromatic ring, in a number of 1 to 10 wherein R.sub.1 may be the same or different and is a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, X is O or NH and Y is O or S. Furthermore, an epoxy resin composition comprising the curing catalyst is disclosed.
    Type: Grant
    Filed: September 11, 1995
    Date of Patent: September 22, 1998
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shuzi Hayase, Yoshihiko Nakano, Shinji Murai, Yukihiro Mikogami
  • Patent number: 5770678
    Abstract: A process for polymerizing oxiranes, oxetanes, oxepanes, dioxolanes, trioxanes, and tetrahydrofurans to their respective polymers by contacting them with a selected metal compound is disclosed; and also a process for depolymerizing polytetrahydrofurans to monomeric tetrahydrofurans by contacting the polymer with a selected metal compound at a temperature of about 100.degree. C. to about 250.degree. C. The catalysts may be in solution or part of a heterogeneous solid, and selected organic compounds are used as accelerators in the polymerizations. The polymeric products, some of which are novel, may be used as polyether monomers for further polymerization, as by reaction with isocyanates to produce polyurethanes, and other useful polymers. Some of the polymeric products are relatively high in molecular weight and are suitable for direct use, for instance as spandex fibers.
    Type: Grant
    Filed: December 9, 1996
    Date of Patent: June 23, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Neville Everton Drysdale, Richard Edmund Bockrath, Norman Herron, Joel David Citron
  • 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: 5663289
    Abstract: This invention relates to novel multifunctional oxetanes, i.e., compounds having multiple oxetane groups, which are useful as initiators in the preparation of star polymers and polymer cascades containing energetic groups. In addition, this invention relates to a process for the preparation of star polymers and polymer cascades, whereby novel multifunctional oxetanes act as initiators in the formation of theses polymers. The reaction of these initiators with various propagating, high-energy oxetanes, such as 3,3-bis-(azidomethyl)oxetane (BAMO) and 3-nitratomethyl-3-methyloxetane (NMMO), gives star polymers with varying molecular weights and functionalities. The star polymers and polymer cascades of the present invention are useful as binders in high-energy formulations.
    Type: Grant
    Filed: October 28, 1994
    Date of Patent: September 2, 1997
    Assignee: Aerojet-General Corporation
    Inventors: Thomas G. Archibald, Roland P. Carlson, Aslam A. Malik, Gerald E. Manser
  • Patent number: 5641853
    Abstract: A process for polymerizing oxepanes, dioxolanes, trioxanes, and tetrahydrofurans to their respective polymers by contacting them with a selected metal compound and an accelerator which is a selected vinyl ester or a selected phosphorous compound.
    Type: Grant
    Filed: February 28, 1996
    Date of Patent: June 24, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Neville Everton Drysdale
  • Patent number: 5641857
    Abstract: Polytetrahydrofuran or polytetrahydrofuran monoesters of C.sub.1 -C.sub.20 -monocarboxylic acids or polytetrahydrofuran monoethers of monohydric C.sub.1 -C.sub.20 -alcohols, having an average molecular weight of from 250 to 10,000 Dalton and liquid at room temperature, are prepared by the cationic polymerization of tetrahydrofuran in the presence of a telogen by a process in which tetrahydrofuran is polymerized in the presence of water, 1,4-butanediol and/or polytetrahydrofuran having an average molecular weight of from 200 to 700 Dalton and/or of a C.sub.1 -C.sub.20 -monocarboxylic acid and/or of a monohydric C.sub.1 -C.sub.20 -alcohol with the aid of a catalytic amount of a zeolite catalyst which has an SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio of from 4:1 to 100:1 and in which the population ratio P of the acid centers on the external surface of the zeolite to the total number of acid centers of the zeolite is 0.03/l or more.
    Type: Grant
    Filed: November 7, 1995
    Date of Patent: June 24, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Roman Dostalek, Rolf Fischer, Ulrich Mueller, Rainer Becker
  • Patent number: 5614126
    Abstract: The invention relates to a substantially solventless curable resin composition, in particular for the fabrication of prepregs, which contains more than 45% by weight of substances which are solid at ambient temperature at least or at lower temperature, and which, in addition to comprising customary modifiers, comprises solid epoxy resins or a mixture of liquid and solid epoxy resins, at least one initiator which is sensitive to UV radiation for the polymerisation of the epoxy resins and has the formula I ##STR1## wherein a and b are each independently of the other 1 or 2, R.sup.1 ist a .pi.-arene, R.sup.2 is a .pi.-arene, an indenyl anion or a cyclopentadienyl anion, [X].sup..crclbar. is an anion [LQ.sub.m ].sup..crclbar.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: March 25, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Urs Gruber, Aloysius H. Manser
  • Patent number: 5478920
    Abstract: When selected silicon compounds are added to cationic polymerizations of cyclic ethers such as oxiranes and tetrahydrofurans, the rate of polymerization is often increased, and novel polyethers are produced. The polyether products are useful as monomers and macromonomers, particularly after hydrolysis of silicon containing end groups.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: December 26, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Neville E. Drysdale
  • Patent number: 5384337
    Abstract: A poromeric material for maintaining an electrostatic charge is provided, the material including a matrix of fibers, a polymeric binder for binding the matrix, and electrets present substantially uniformly throughout the poromeric material. Also provided are methods for making the poromeric material. In one embodiment, a polymeric binder mixture having electrets substantially uniformly contained therein is formed. The matrix of fibers is impregnated with the mixture and cured, whereby the electrets are substantially uniformly distributed throughout the matrix to produce the electrostatic poromeric material. In an alternative embodiment, the electrets are contained in the fibers of the matrix. The poromeric material may be used to encase a core to form a roller, for example, a hickey-removing roller.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: January 24, 1995
    Inventor: William D. Budinger
  • Patent number: 5362848
    Abstract: This invention relates to novel multifunctional oxetanes, i.e., compounds having multiple oxetane groups, which are useful as initiators in the preparation of star polymers and polymer cascades containing energetic groups. In addition, this invention relates to a process for the preparation of star polymers and polymer cascades, whereby novel multifunctional oxetanes act as initiators in the formation of theses polymers. The reaction of these initiators with various propagating, high-energy oxetanes, such as 3,3-bis-(azidomethyl)oxetane (BAMO) and 3-nitratomethyl-3-methyloxetane (NMMO), gives star polymers with varying molecular weights and functionalities. The star polymers and polymer cascades of the present invention are useful as binders in high-energy formulations.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: November 8, 1994
    Assignee: Aerojet-General Corporation
    Inventors: Thomas G. Archibald, Roland P. Carlson, Aslam A. Malik, Gerald E. Manser
  • Patent number: 5344911
    Abstract: Processes for producing a polyoxymethylene copolymer includes forming a crude polyoxymethylene copolymer by subjecting a reaction system containing trioxane, a cyclic ether or cyclic formal comonomer, and a catalyst (e.g., boron trifluoride or a coordination compound thereof) to copolymerization reaction conditions. During copolymerization, both the total content of impurities and catalyst in the copolymerization reaction system are adjusted. In this regard, the impurities content (i.e., those compounds which form unstable end groups in the polyoxymethylene copolymer and/or those compounds having a chain-terminating or chain-transfer function) in the copolymerization reaction system is adjusted to 1.times.10.sup.-2 mole percent or less based on the total monomer amount, while the the content of the catalyst in the copolymerization reaction system to between 1.times.10.sup.-3 to 1.times.10.sup.-2 mole percent based on the total monomer amount.
    Type: Grant
    Filed: March 5, 1993
    Date of Patent: September 6, 1994
    Assignees: Polyplastics Co., Ltd., Hoechst Aktiengesellschaft
    Inventors: Kaoru Yamamoto, Nagayoshi Maeda, Makoto Kamiya, Toshiro Murao, Gerhard Reuschel, Dietrich Fleischer