Phosphorus-containing Reactant Patents (Class 528/287)
  • Patent number: 6093786
    Abstract: Polytrimethylene terephthalate is prepared in a process which includes adding a hindered phenol and an aromatic organophosphite to the polymerization reaction mixture. The process generates a reduced level of acrolein and prepares an improved polyester product compared with processes without the phenol and organophosphite additives.
    Type: Grant
    Filed: August 15, 1997
    Date of Patent: July 25, 2000
    Assignee: Shell Oil Company
    Inventor: Donald Ross Kelsey
  • Patent number: 6051620
    Abstract: Polyester polyols which contain at least one dihydrazide linkage --C(.dbd.O)--NHNH--C(.dbd.O)-- reduce the incidence of scorching when used as a reactant in the manufacture of polyurethane foam. Also disclosed are compounds of structures (2) and (3):D--HN(--NH--C(.dbd.O)--R--C(.dbd.O)NH).sub.0-1 --NH--D (2)(A--C(.dbd.T)--NH)--.sub.
    Type: Grant
    Filed: June 11, 1997
    Date of Patent: April 18, 2000
    Assignee: CK Witco Corporation
    Inventors: Ibrahim Bechara, Thomas R. Baranowski, James Stogis, Thomas H. Morong
  • Patent number: 6046263
    Abstract: Products are described which are obtainable by reacting compounds of formula I with compounds of formula IIa or/and IIb and IIIa or/and IIIb and additionally, where appropriate, IV ##STR1## wherein the general symbols are as defined in claim 1, the compound of formula I being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate, the compound of formula IIa being, for example, diethanolamine, the compound of formula IIIa being, for example, methyl oleate, and the compound of formula IV being, for example, sulfur. The cited products can be used as liquid antioxidants in organic materials.
    Type: Grant
    Filed: May 19, 1998
    Date of Patent: April 4, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Michael Rasberger, Samuel Evans, Paul Dubs, Stephan Allenbach
  • Patent number: 6037421
    Abstract: The present invention provides a condensation polymer, selected from the group consisting of polyamides and polyesters, that comprises between about 0.5% and about 4.0%, based on the theoretical moles of monomeric repeat units, of a trifunctional repeat unit. One of the functional groups of the trifunctional repeat unit comprises a moiety that imparts a desired property to the polymer, such as stain resistance or UV stabilization. One particular embodiment of the invention is a nylon 66 polymer that comprises between about 0.5% and 4.0%, based on the theoretical moles of nylon 66 repeat units, of a trifunctional repeat unit having the general formula: ##STR1## wherein R is the functional group that imparts a desired property to the polymer; a, b, and c are separately integers from 0-5. Preferably a+b=5 and c is 3.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: March 14, 2000
    Assignee: Solutia Inc.
    Inventor: Jawed Asrar
  • Patent number: 5998568
    Abstract: A method for making a polyester resin comprises reacting a first polyfunctional alcohol or polyfunctional thiol and a carbonate in the presence of a catalyst to form an alkoxylated intermediate. The catalyst comprises: (1) a metal, a salt of a metal, or mixtures thereof and (2) a quaternary ammonium salt, a tertiary amine, an imidazole, or mixtures thereof. The alkoxylated intermediate is then reacted with a polyfunctional organic acid or anhydride thereof to form the polyester resin.
    Type: Grant
    Filed: January 14, 1999
    Date of Patent: December 7, 1999
    Assignee: Reichhold, Inc.
    Inventors: Hildeberto Nava, Karin F. Nelson-Baron
  • Patent number: 5989697
    Abstract: Claimed is a copolyether amide having a melting point in the range of 180.degree. to 260.degree. C., incorporating at least 10 wt. % and not more than 30 wt. % of ethylene oxide groups, and composed of 30 to 60 wt. % of polyamide segments and 70 to 40 wt. % of segments derived from a (cyclo)aliphatic or aromatic dicarboxylic acid or a dimeric fatty acid and a polyoxyalkylene diamine derived from a polyoxyalkylene group having a molecular weight of 600 to 6000 and an atomic ratio of carbon to oxygen of 2.0 to 4.3. Also claimed is a non-porous, waterproof film having a water vapor permeability of at least 1000 g/m.sup.2 day determined at 30.degree. C. and 50% RH in accordance with ASTM E96-66 which is based on a the use of these films in rainwear, shoes, tents, chairs, as mattress covers and underslating, for medical purpose garments, and for the manufacture of dressings.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: November 23, 1999
    Assignee: Akzo Nobel, NV
    Inventor: Bert Gebben
  • Patent number: 5990318
    Abstract: Novel soluble polyester-supported chiral phosphines have been prepared and have been used in the preparation of rhodium and ruthenium catalysts. Such polymer-supported catalysts show high catalytic activities and enantioselectivities. In the case of Ru(BINAP) catalyst supported on soluble polyester, the resulting catalysts were found to be more active than those of the corresponding homogeneous Ru(BINAP) catalysts in the asymmetric hydrogenation of 2-arylpropenoic acids. These soluble polyester-supported catalysts can be easily separated from the reaction mixture and then be reused without loss of activity and selectivity.
    Type: Grant
    Filed: March 6, 1998
    Date of Patent: November 23, 1999
    Assignee: The Hong Kong Polytechnic University
    Inventors: Albert Sun-Chi Chan, Qing-Hua Fan
  • Patent number: 5986040
    Abstract: A moldable linear polyester resin consisting essentially of a polyester having the formula: ##STR1## where R is an alkyl from 1 to 6 carbon atoms and n is greater than about 70, said polyester resin being derived from the transesterification reaction of a starting DMCD and a starting CHDM wherein the trans-cis ratio of repeating units derived from DMCD is preferably greater than about 8 to 1, and the trans-cis ratio of repeating units derived from DMCD is preferable greater than about 1 to 1, said polyester resin having crystalline properties with a preferable viscosity greater than 4500 poise and a melting temperature greater than 216 degrees Centigrade.
    Type: Grant
    Filed: September 3, 1998
    Date of Patent: November 16, 1999
    Assignee: General Electric Company
    Inventors: Bimal R. Patel, Gary F. Smith, Timothy E. Banach
  • Patent number: 5942596
    Abstract: The present invention relates to a process comprising polymerizing repeat units derived from an acid component comprising terephthalic acid and naphthalenedicarboxylic acid and at least one glycol in the presence of less than about 10 ppm sodium carbonate and between about 10 and about 60 ppm phosphorus. Polyesters formed via the process of the present invention display surprisingly good clarity and color.
    Type: Grant
    Filed: February 24, 1998
    Date of Patent: August 24, 1999
    Assignee: Eastman Chemical Company
    Inventors: Maureen Clare Maag, David Taylor Bowers, Robert Lewis Stoots, Jr.
  • Patent number: 5922828
    Abstract: A novel process to produce polyethylene terephthalate (PET) using a specific catalyst stabilizer system is described. The catalyst stabilizer system is specific for producing PET wherein the polycondensation catalyst is a titanium and the stabilizer possesses an irreversible oxidation potential of at least +2.0 volts versus SCE. The novel process results in PET having acceptable color and low acetaldehyde content.
    Type: Grant
    Filed: August 13, 1997
    Date of Patent: July 13, 1999
    Assignee: Hoechst Celanese Corp.
    Inventor: David Anthony Schiraldi
  • Patent number: 5914388
    Abstract: A process for the preparation of polyphosphazenes is provided that includes the cationic solution polymerization reaction of a phosphoranimine, using a main group or transition metal halide, or other appropriate halide salt, including a linear phosphazene salt of any chain length, or a preformed non-phosphazene polymer containing a main or transition metal chloride, as an initiator. In a preferred embodiment, triarmed-star polyphosphazenes having the formula N{RN(H)R'.sub.2 P--(N.dbd.PR'.sub.2).sub.n }.sub.3 are prepared via this method. Also, a methods for synthesis of the monomer Cl.sub.3 P.dbd.NSiMe.sub.3 and cyclic trimer N.sub.3 P.sub.3 X.sub.6 from the reactants N(SiR.sub.3).sub.3 and PX.sub.5 are also described.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: June 22, 1999
    Assignee: The Penn State Research Foundation
    Inventors: Harry R. Allcock, Christopher T. Morrissey, Ian Manners, Charles H. Honeyman, James M. Nelson, Chester A. Crane, Scott D. Reeves, A. Paul Primrose, Thomas J. Hartle, R. Prange
  • Patent number: 5874515
    Abstract: There is disclosed a process for reducing the number of gels generated in polyethylene terephthalate (PET) resin. Gels are crosslinked polymers created by thermal and thermo-oxidative degradation induced during polymer production. The instant process comprises the addition of primary and secondary antioxidants prior to the PET polycondensation reaction in order to reduce the amount of thermal degradation which occurs. The polyethylene terephthalate produced by this process formed approximately 25 to 90% fewer gels while maintaining physical properties suitable for use in fiber, film, and molding applications.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: February 23, 1999
    Assignee: Hoechst Celanese Corporation
    Inventors: Xiaoyan Huang, Ligia Dominguez
  • Patent number: 5859154
    Abstract: An adherent coating composition and method has a resin composition that is the polymerization reaction product of one or more polyhydric alcohols and two polybasic carboxylic acids and salt forming compounds of phosphorus. The carboxylic acid is comprised of at least adipic acid and phthalic anhydride in a mole ratio in the range of about 0.6:1 to about 3:1, and the phosphorus compound is present in the range of about 1 to about 5 weight percent of the resin composition. The resin composition can have a weight average molecular weight in the range of about 1100 to about 4000 and an acid value in the range of about 5 to about 40. Optionally, the resin can have up to about 35 weight percent of tetrahydrophthlic anhydride. The resin composition is ungelled and curable with crosslinking agents in an amount of about 30 to about 90 weight percent of resin to about 10 to about 45 weight percent of the crosslinking agent.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: January 12, 1999
    Assignee: PPG Industries, Inc.
    Inventors: Rodger G. Temple, Paul H. Lamers, H. Hayne Crum, III, Karen L. Wild
  • Patent number: 5847184
    Abstract: The present invention relates to a process for preparing of phosphorus-containing dicarboxylic acids of the formula (I) ##STR1## where R.sup.1 and R.sup.2 are identical or different and are each a straight-chain or branched alkyl radical having from 1 to 8 carbon atoms, a cycloaliphatic radical having 5 or 6 carbon atoms in the ring, an unsubstituted or substituted aryl radical having from 6 to 10 carbon atoms, or R.sup.1 and R.sup.2 form, with inclusion of the phosphorus atom, a ring having from 5 to 8 members, and m and n are each, independently of one another 0 or 1, by reacting a compound of the formula (II) ##STR2## where R.sup.1, R.sup.2 and m are as defined above, with fumaric acid, maleic acid or itaconic acid in the presence of a saturated aliphatic monocarboxylic acid having a total of from 1 to 5 carbon atoms as solvent at from 100.degree. to 200.degree. C. under atmospheric pressure or superatmospheric pressure.
    Type: Grant
    Filed: September 22, 1995
    Date of Patent: December 8, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans-Jerg Kleiner
  • Patent number: 5756033
    Abstract: The present invention is a pre-oriented, undrawn polyester fiber spun with spooling speeds of at least 3,000 m/min., wherein the polyester is a copolymer comprised essentially of ethylene terephthalate units and up to 10 weight % of other dicarboxylic acids or other diols, and carboxy phosphonic acid units of the formula: ##STR1## wherein R is selected from C.sub.1-10 -alkylene, C.sub.1-10 -cycloalkylene or C.sub.6-10 -arylene, in a quantity corresponding to 30 to 500 ppm phosphorus, in relation to polyester. The invention also comprises a process for the production of this fiber.
    Type: Grant
    Filed: February 6, 1997
    Date of Patent: May 26, 1998
    Assignee: Zimmer Aktiengesellschaft
    Inventors: Heinz-Dieter Schumann, Ulrich Thiele
  • Patent number: 5747606
    Abstract: An increase in the molecular weight of polyester and recycled polyester can be achieved by blending said polyester with a difunctional epoxy resin and a sterically hindered hydroxyphenylalkylphosphonic acid ester or half-ester and heating the blend to above the melting point (glass transition temperature) of the polyester.
    Type: Grant
    Filed: July 11, 1997
    Date of Patent: May 5, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Rudolf Pfaendner, Kurt Hoffmann, Heinz Herbst
  • Patent number: 5744572
    Abstract: A process for the acceleration of the polycondensation of polyester made by the esterification of at least one dicarboxylic acid with at least one diol, precondensation, melt phase polycondensation, granulation, crystallization and solid phase polycondensation comprising the addition, prior to the precondensation reaction, of from about 30 to about 900 ppm phosphorus in relation to the polyester in the form of carboxy phosphonic acid of the formula: ##STR1## wherein, R is selected from the group consisting of C.sub.1-10 -alkylene, C.sub.1-10 -cycloalkylene, and C.sub.6-10 -arylene and R.sup.1, R.sup.2, and R.sup.3 are selected from the group consisting of hydrogen, C.sub.1-10 -alkyl, C.sub.1-10 -cycloalkyl, and C.sub.6-10 -aryl, provided that at least two of R.sup.1, R.sup.2, and R.sup.3 are hydrogen.
    Type: Grant
    Filed: February 6, 1997
    Date of Patent: April 28, 1998
    Assignee: Zimmer AG
    Inventors: Heinz-Dieter Schumann, Ulrich Thiele
  • Patent number: 5714570
    Abstract: A method for preparing polyester by use of a catalyst. The method comprises the steps of: esterifying either a terephthalic acid, a dicarboxylic acid containing terephthalic acid or derivatives thereof with either ethylene glycol or a glycol containing ethylene glycol, or derivatives thereof to produce an esterification product containing either bis(.beta.-hydroxyethyl) terephthalate, its low molecular weight polymer, or a combination of .beta.-hydroxyethyl terephthalate and its low molecular weight polymer; and continuously polycondensing the obtained esterification product to prepare a polyester, wherein in the said polycondensing step, a composite polymerization catalyst dissolved in an ethylene glycol or an ethylene glycol-containing solution, consisting of a compound of antimony, a compound of titanium, and a compound of tin is used.
    Type: Grant
    Filed: July 16, 1996
    Date of Patent: February 3, 1998
    Assignee: Korea Institute of Science and Technology
    Inventors: Chung Yup Kim, Hyun Nam Cho, Hoi Wan Yoo, Hyung Joon Kim
  • Patent number: 5698664
    Abstract: A process for the preparation of polyphosphazenes is provided that includes the cationic solution polymerization reaction of a phosphoranimine, using a main group or transition metal halide, or other appropriate halide salt, including a linear phosphazene salt of any chain length, or a preformed nonphosphazene polymer containing a main or transition metal chloride, as an initiator.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: December 16, 1997
    Assignees: The Penn State Research Foundation, University of Toronto
    Inventors: Harry R. Allcock, Christopher T. Morrissey, Ian Manners, Charles H. Honeyman
  • Patent number: 5688906
    Abstract: A method for forming a polyamic acid having nonlinear optical (NLO) or pre-NLO side chains, which method includes the steps of:(1) providing a bis-(aromatic dicarboxylic acid anhydride) containing at least one NLO or pre-NLO side chain having the structure represented by:D-R-Awherein D, R and A form a delocalized resonance configuration in which R is a pi-conjugated non-centrosymmetric moiety, A is hydrogen or an electron withdrawing moiety and D is an electron donating moiety covalently linked to the bis-(aromatic dicarboxylic acid anhydride); and(2) reacting the bis-(aromatic dicarboxylic acid anhydride) with an aromatic diamine to form a polyamic acid having NLO or pre-NLO side chains. Methods for preparing polyamic acids having NLO or pre-NLO side chains by reacting aromatic diamines having NLO or pre-NLO side chains with bis-(aromatic dicarboxylic acid anhydrides) are also disclosed. Methods of forming the polyamic acids into polyimides having NLO side chains are also included.
    Type: Grant
    Filed: August 7, 1995
    Date of Patent: November 18, 1997
    Assignee: Enichem S.p.A.
    Inventors: Kwan-Yue Alex Jen, Kevin Joel Drost
  • Patent number: 5681919
    Abstract: A magnetic recording medium is prepared by applying a magnetic coating composition onto a non-magnetic support and curing said composition, said coating composition containing ferromagnetic particles dispersed in a binder comprising a thermoplastic resin selected from the group consisting of polyurethanes and polyester wherein there is chemically bonded to said resin at least one aminoalkylphosphonate represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different oxyalkyl radicals having from 2 to 12 carbon atoms, R.sup.3 is an alkylene radical having from 1 to 12 carbon atoms, or an aralkylene radical having from 7 to 10 carbon atoms R.sup.4 is an alkyl radical having from 1 to 12 carbon atoms, a cycloalkyl radical having from 5 to 12 carbon atoms, or an aryl radical having from 6 to 12 carbon atoms wherein the aryl radical may contain a halogen atom, a hydroxyl group, or an amino group, and M.sup.+ is a metal ion or an ammonium ion.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: October 28, 1997
    Assignee: Morton International, Inc.
    Inventors: Charles J. Amirsakis, David E. Vietti, Daniel P. Heberer, Louis C. Dolmon, Lawrence Picchiotti
  • Patent number: 5677416
    Abstract: There are disclosed a wholly aromatic polyester represented by formula I with enhanced flame retardance and chemical stability, and a method for the preparing the same. The polymer is prepared in interface polymerization wherein an alkali aqueous phase containing cyclotriphosphagene-containing bisphenols is in contact with an organic phase containing aromatic dicarboxylic acid chlorides in the presence of a phase transfer catalyst. ##STR1## wherein m and n each are an integer which satisfies the following conditions: 0<m/(m+n)<1 and 0<n/(m+n)<1; X represents --O--, --S--, --SO.sub.2 --, --SO--, --CO--, an alkylene group of C.sub.1-4, or an alkylidene group of C.sub.1-4 ; and R.sub.1, R.sub.2, R.sub.3, R.sub.1 ', R.sub.2 ', R.sub.3 ' and R.sub.4 ' are the same or different, and represent a hydrogen atom, a halogen atom, or an alkyl group of C.sub.1-4 or the derivatives thereof, respectively.
    Type: Grant
    Filed: October 30, 1996
    Date of Patent: October 14, 1997
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Young-Hoon Ko, Seonkyeong Cheong
  • Patent number: 5654380
    Abstract: Provided are an aliphatic polyester carbonate having biodegradability and having a content of carbonate unit of at least 5 mol %, a weight-average molecular weight of at least 100,000, a melt viscosity of 2,000-50,000 poises at 190.degree. C. and under a load of 60 kg and a melting point of 70.degree.-180.degree. C., and a process for producing said aliphatic polyester carbonate which comprises reacting an aliphatic dihydroxy compound with an aliphatic dibasic acid in the presence of an ester exchange catalyst to obtain an oligomer and then reacting the oligomer with a diaryl carbonate in the presence of the ester exchange catalyst. A phosphorus compound may be added to the aliphatic polyester carbonate for the purpose of stabilization.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: August 5, 1997
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Ryozo Kawai, Mitsuo Miura, Kyohei Takakuwa, Yoshinori Isahaya, Takayasu Fujimori, Jiro Suito, Makoto Nakamura
  • Patent number: 5608027
    Abstract: A composition comprising a phosphorus containing acid and an ester of a phosphorus containing acid useful for imparting improved physical and chemical properties to polymers containing polyesters, copolyester carbonates, polycarbonates, and mixtures thereof, a method of treating said polymers with said composition, and articles of manufacture comprising said polymers and said composition.
    Type: Grant
    Filed: November 22, 1995
    Date of Patent: March 4, 1997
    Assignee: General Electric Company
    Inventors: Richard Crosby, James L. DeRudder, Larry I. Flowers, Ye-Gang Lin, Roy R. Odle
  • Patent number: 5602212
    Abstract: A linear copolyester is prepared by polycondensation of an aromatic bicarboxylic acid with an alkylene glycol and with a carboxyphosphinic acid or anhydride which produces monomeric units having the formula: ##STR1## wherein R.sub.1 is an alkylene or phenyl radical and R.sub.2 is an alkyl or phenyl radical.This copolyester can be used as a flame-retardant additive for organic polymers.
    Type: Grant
    Filed: May 28, 1996
    Date of Patent: February 11, 1997
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Carlo Neri, Gianluigi Landoni
  • Patent number: 5571888
    Abstract: A process for preparing a flame-retardant phosphorus-containing unsaturated polyester resin blend, comprising the following steps:(a) reacting(1) a phosphorus-containing monomer having the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are respectively H, C.sub.1 -C.sub.4 alkyl, phenyl, alkaryl or aralkyl, with(2) a saturated dicarboxylic acid, or a saturated dicarboxylic acid anhydride,(3) a double bond-containing unsaturated dicarboxylic acid or a double bond-containing unsaturated dicarboxylic acid anhydride, and(4) a diolin the presence of a metal catalyst combined with an acid to form an unsaturated polyester oligomer having the formula: ##STR2## wherein R.sub.5 and R.sub.6 are respectively C.sub.1 -C.sub.4 alkylene, alkarylene, phenylene or aralkylene,R.sub.4 is a vinyl-containing group,x is an integer of 1-10,y is an integer of 1-10,z is an integer of 1-10, and(b) blending said unsaturated polyester oligomer with a vinyl-containing monomer.
    Type: Grant
    Filed: June 14, 1995
    Date of Patent: November 5, 1996
    Assignee: Industrial Technology Research Institute
    Inventors: Yi-Ni Cheng, Shinn-Jen Chang, Yuung-Ching Sheen, Shyue-Pyng Juang
  • Patent number: 5565545
    Abstract: Process for adjusting the haze value of ethylene terephthalate homopolymers and low-modified copolymers to a value in the range of 0.5 to 20 NTU while they are being produced by direct esterification and polycondensation, where an amount of antimony and germanium catalyst that is determined on the basis of the desired degree of turbidity is added before or at the start of the esterification step in the absence of other catalysts and other compounds that would affect the haze value, and after achieving a conversion of 90 to 98%, another dose of antimony catalyst corresponding to a total added amount of Sb+Ge in the range of 160 to 350 ppm is added, and then after addition of the catalyst is concluded, a phosphorus stabilizer is added to the reaction mixture in an amount to correspond to 0 to 50 ppm phosphorus.
    Type: Grant
    Filed: February 15, 1995
    Date of Patent: October 15, 1996
    Assignee: Zimmer Aktiengesellschaft
    Inventors: Gerald Kriesche, Ulrich Thiele
  • Patent number: 5550207
    Abstract: A linear copolyester is prepared by polycondensation of an aromatic bicarboxylic acid with an alkylene glycol and with a carboxyphosphinic acid or anhydride which produces monomeric units having the formula: ##STR1## wherein R.sub.1 is an alkylene or phenyl radical and R.sub.2 is an alkyl or phenyl radical. This copolyester can be used as a flame-retardant additive for organic polymers.
    Type: Grant
    Filed: May 23, 1994
    Date of Patent: August 27, 1996
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Carlo Neri, Gianluigi Landoni
  • Patent number: 5530088
    Abstract: A heat resistant phosphorus-containing polymeric flame retardant and a process for preparing the same are disclosed. The process is characterized in that in polycondensation a selected metal salt serving as cocatalyst is used to catalyze a phosphorus-containing compound, a saturated dicarboxylic acid or the derivatives thereof, and a diol to form a high phosphorus content, high molecular weight flame retardant. The selected metal salts can promote the polymerization of phosphorus-containing compounds and polyester, and can inhibit side reactions and depolymerization so as to increase the phosphorus content of the resulting products and reduce the manufacturing cost. The flame retardants thus prepared can endure processing at an elevated temperature and thus are suitable for being applied in flame retardant fibers, fabrics, nonwoven fabrics, adhesives, and plastics.
    Type: Grant
    Filed: June 21, 1995
    Date of Patent: June 25, 1996
    Assignee: Industrial Technology Research Institute
    Inventors: Yuung-Ching Sheen, Shinn-Jen Chang, Yi-Ni Cheng, Rong-Shuh Chang
  • Patent number: 5523381
    Abstract: Described is a process for producing linear polyesters of improved whiteness and reduced yellowness by esterification of aromatic dicarboxylic acids or transesterification of their bis(lower alkyl) esters with or without aliphatic dicarboxylic acids with diols to form bisdiol esters and their oligomers and further condensation of these preproducts to spinnable polyesters, which comprises adding to the esterification, transesterification or polycondensation hatch from 0.5 to 15% by weight of phosphorus-containing modifiers and conducting the polycondensation initially in the melt to an IV from 0.4 to 0.55 dl/g and thereafter in solid phase to an IV from 0.62 to 0.72, the indicated IV values being measured at 25.degree. C. in dichloroacetic acid. The phosphorus-containing modifiers used preferably have the formula V or VI ##STR1## where R.sup.6 is alkylene or polymethylene of 2 to 6 carbon atoms or phenyl and R.sup.5 is alkyl of 1 to 6 carbon atoms, aryl or aralkyl, in the cocondensed state.
    Type: Grant
    Filed: August 15, 1994
    Date of Patent: June 4, 1996
    Assignee: Hoechst AG
    Inventors: Ralf Ueberdiek, Eckhard Husing
  • Patent number: 5519108
    Abstract: A catalyst composition for use in the preparation of poly(butylene terephthalate) from dimethyl terephthalate, comprising: (a) a titanium compound primary catalyst, from about 0.0005 PHR to about 5 PHR; (b) a first co-catalyst containing at least one of Zn, Co, Mn, Mg, Ca, or Pb series compounds, between about 0.0001 PHR and 5 PHR; and (c) a second co-catalyst containing an alkali metal phosphate, an alkali metal phosphite, an alkali hypophosphite, or an alkali metal polyphosphate between about 0.0001 PHR and 5 PHR; wherein PHR represents parts of the primary catalyst or the co-catalyst per one hundred parts, by weight, of dimethyl terephthalate. Preferred titanium compounds include tetrabutyl titanate or tetra(isopropyl)titanate. Preferred metal compounds for use as first co-catalyst are metal acetates. The alkali metal phosphate can be a phosphate salt containing one, two, or three metal groups; and the alkali metal phosphite can be a phosphite salt containing one or two metal groups.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: May 21, 1996
    Assignee: Industrial Technology Research Institute
    Inventors: Wu-Bin Yuo, Chien-Shiun Liao, Wen-Jeng Lin, Cheng Yeh, Yu-Shan Chao, Li-Kuel Lin
  • Patent number: 5516879
    Abstract: A catalyst composition for use in the preparation of poly(butylene terephthalate) from dimethyl terephthalate, comprising: (a) a titanium compound primary catalyst, from about 0.01 PHR to about 1 PHR; and (b) an alkali metal phosphate or alkali metal phosphite co-catalyst, from about 0.001 PHR to about 1 PHR; wherein PHR represents parts of the primary catalyst or the co-catalyst per one hundred parts, by weight, of dimethyl terephthalate. Preferred titanium compounds include tetrabutyl titanate or tetra(isopropyl) titanate; the alkali metal phosphate can be a phosphate salt containing one, two, or three metal groups; and the alkali metal phosphite can be a phosphite salt containing one or two metal groups. With this catalyst composition, the transesterification rate was increased by 10 percent or more. Furthermore, the reaction product poly(butylene terephthalate) shows an increased intrinsic viscosity over those without the co-catalyst, indicating a greater degree of polymerization.
    Type: Grant
    Filed: March 28, 1995
    Date of Patent: May 14, 1996
    Assignee: Industrial Technology Research Institute
    Inventors: Wu-Bin Yuo, Wen-Jeng Lin, Hsin-Herng Wang, Jian-Hong Chen
  • Patent number: 5502118
    Abstract: Polymer salts whose anionic component is a polyester which comprises the product of reaction of the individual components a), b) and c) and if desired d) and if desired e), wherea) is a dicarboxylic acid or a reactive derivative of a dicarboxylic acid, being free from sulfo groups,b) is a difunctional aromatic, aliphatic or cycloaliphatic sulfo compound whose functional groups are hydroxyl or carboxyl, or hydroxyl and carboxyl,c) is an aliphatic, cycloaliphatic or aromatic diol, a polyetherdiol or a polycarbonatediol,d) is a polyfunctional compound (functionality>2) whose functional groups are hydroxyl or carboxyl, or hydroxyl and carboxyl, ande) is a monocarboxylic acidand whose cationic component comprises hydrogen atoms, metal cations, substituted ammonium cations, immonium cations, guanidinium cations, phosphonium, arsonium or stibonium cations or a mixture of the abovementioned cations, are suitable as charge control agents and charge improvers in electrophotographic toners and developers, in triboele
    Type: Grant
    Filed: September 21, 1994
    Date of Patent: March 26, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Tobias Macholdt, Ru/ diger Bauer, Joachim Zo/ ller
  • Patent number: 5500285
    Abstract: Phosphino oxide group containing compounds useful as flame retardant additives, having the general formula (I): ##STR1## wherein: X and X.sub.1 represent a hydrogen atom or, when taken jointly, they represent an NR.sub.1 moiety in which R.sub.1 stands for a hydrogen atom; a linear or branched aliphatic C.sub.1 -C.sub.5 moiety; a linear or branched C.sub.2 -C.sub.6 acyl moiety; a phenyl moiety;R represents a cyclic or polycyclic C.sub.4 -C.sub.9 moiety containing two carboxy groups, possibly esterified with univalent alcohols or glycols, or transformed into anhydrides, or two hydroxy groups.
    Type: Grant
    Filed: January 17, 1995
    Date of Patent: March 19, 1996
    Assignees: Great Lakes Chemical Italia S.r.l., Eniricerche S.p.A.
    Inventors: Vittorio Carletti, Gianfranco Longhini, Riccardo Po', Roberto Podesta', Anna M. Romano, Cecilia Querci
  • Patent number: 5494993
    Abstract: Described are low-pill, low-flammability linear fiber-forming polyesters formed from dicarboxylic acid and diol components, which polyesters contain in their polymer chain modifying units formed by esterification or transesterification from compounds of the formulae I and/or II and/or III ##STR1## where R.sup.1 and R.sup.2 are identical or different and each is a univalent aliphatic, araliphatic or aromatic hydrocarbon radical having 1 to 12 carbon atoms, orR.sup.1 and R.sup.2 are together a bivalent aliphatic, araliphatic or aromatic radical,R.sup.3 is an (n+1)-valent organic radical,A is a group capable of ester formation, n is an integer from 1 to 3,R.sup.4 and R.sup.5 are identical or different and each is hydrogen or a univalent aliphatic, araliphatic or aromatic hydrocarbon radical having 1 to 12 carbon atoms,y is an integer from 1 to 10,R.sup.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: February 27, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Volker Freudenberger, Peter Klein, Hans-Jerg Kleiner
  • Patent number: 5492998
    Abstract: Novel polymers of general formula: ##STR1## wherein R is an alkyl or aryl group that contains an active hydrogen atom (as determined by the Zerewitinoff test); A is a spacing group having at least one carbon atom; B is a spacing group having at least two carbon atoms; and R and R' are alkyl or aryl groups. The polymer is synthesized via the Mannich pathway, involving formation of an imine intermediate.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: February 20, 1996
    Assignees: Lifesource International, Ltd., Jojani Inc.
    Inventor: Nicholas M. Irving
  • Patent number: 5464694
    Abstract: There are described a spinnable polyester for producing fully oriented polyester yarn by high speed spinning based on polyethylene terephthalate modified by incorporation of aliphatic dicarboxylic acids as cocondensed units and which may additionally contain up to 5% by weight of further additaments customary for modifying polyethylene terephthalate, wherein modifying aliphatic dicarboxylic acids present as cocodensed units have in total from 4 to 10 carbon atoms and are present in such an amount that the glass transition temperature of the polyester is 70.degree. C. or below, the recrystallization temperature of the polyester is 180.degree. C. or below and the heat of fusion of the polyester, determined by DSC measurement, is 30 J/g or below, a polyester yarn producible therefrom by high speed spinning, which has a novel combination of high strength, high modulus and enhanced shrinkage capacity, and a process for producing this yarn.
    Type: Grant
    Filed: September 2, 1993
    Date of Patent: November 7, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Bernd Heinrich
  • Patent number: 5436312
    Abstract: Aqueous filler composition comprising a polyester resin, which is built up of the educts (a), (b), (c), (d) and (e) or their ester-forming derivatives, the sum of the reactants corresponding to 100 mol-% and the ratio of the sum of the hydroxyl equivalents (eg OH) to the sum of the carboxyl equivalents in the reactants being between 0.5 and 2.0, where(a) is at least one dicarboxylic acid which is not a sulfo or phosphorus monomer,(b) is 0 to 15 mol-% of at least one difunctional sulfo or phosphono monomer, the functional groups of which are carboxyl and/or hydroxyl groups, having at least one sulfonate or phosphonate group,(c) is at least one difunctional compound which is derived from a glycol containing two --C(R).sub.
    Type: Grant
    Filed: September 15, 1994
    Date of Patent: July 25, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Reiner Exner, Michael Schwab, Ute Kuhn, Joachim Zoeller
  • Patent number: 5418309
    Abstract: The present invention provides a powder coating composition which is suitable for precoated steel plates. The powder coating composition has excellent storage stability (e.g. blocking resistance) and provides a cured film having good weather resistance and a good balance of hardness and processability. The powder coating composition comprises;(I) 95 to 70% by weight of a polyester resin having a glass transition temperature of 40.degree. to 70.degree. C., prepared from (i) and acid component containing at least 80 mole % of an aromatic dicarboxylic acid with (ii) a polyol component which comprises(a) at least 50 mole % of neopentyl glycol, and(b) 1 to 10% by weight of a diol selected from the group consisting of a linear chain C.sub.8 -C.sub.16 alkylene diol, 2-methyl-1,8-octane diol and a mixture thereof, and(II) 5 to 30% by weight of a curing agent.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: May 23, 1995
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Hisaki Tanabe, Yasuhiko Nakae, Yoshio Eguchi
  • Patent number: 5417908
    Abstract: Process for making a polyester having polyethylene terephthalate units including transesterifying a terephthalic acid ester with a glycol using a manganese salt as catalyst and then subjecting the product to a polycondensation reaction using a germanium-containing catalyst to form a polyester; adding phosphorous compounds to block 80 to 99% by weight of the active manganese salt thus leaving an unblocked portion of the manganese salt prior to the polycondensation; and adding 10 to 100 ppm of Ge at the end of a ethylene glycol stage of the polymerization so that the Ge and the unblocked portion of the manganese salts provide the germanium-containing catalyst for the polycondensation reaction. The P/Mn molar ratio being less than 1. The reaction mixture contains 10 to 100 ppm of manganese during the reaction.
    Type: Grant
    Filed: December 15, 1993
    Date of Patent: May 23, 1995
    Assignee: Rhone-Poulenc Viscosuisse SA
    Inventors: Josiane Enggasser, Roland Stahlin, Paul Gesche
  • Patent number: 5399428
    Abstract: A flame retardant linear polyester comprising the product of a polyethylene terephthalate prepolymer, bis-hydroxy alkyl bibenzoate and a flame-retarding amount of a carboxy-phosphinic acid, a process for producing the polyester and products produced from the polyester are disclosed.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: March 21, 1995
    Assignee: Monsanto Company
    Inventor: Jawed Asrar
  • Patent number: 5399429
    Abstract: A flame retardant linear polyester comprising the product of recycled polyethylene terephthalate, bis-hydroxy alkyl bibenzoate and a flame-retarding amount of a carboxy-phosphinic acid, a process for producing the polyester and products produced from the polyester are disclosed.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: March 21, 1995
    Assignee: Monsanto Company
    Inventor: Jawed Asrar
  • Patent number: 5399654
    Abstract: A phosphorus-containing wholly aromatic polyester is produced by an interfacial polymerization method which includes the step of reacting a phosphorus-containing bisphenol compound and a bisphenol compound with dicarboxylic acid chlorides. An organic layer containing the dicarboxylic acid chlorides and phase transfer catalyst is added into an alkaline aqueous layer which contains a bisphenol compound.
    Type: Grant
    Filed: October 21, 1993
    Date of Patent: March 21, 1995
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Young H. Ko, Seung D. Cho, Byung C. Jeon
  • Patent number: 5391700
    Abstract: This invention provides a process for producing with industrially good efficiency a polyester having a high melting point and biodegradability. In this process, ring-opening copolymerization of a cyclic acid anhydride containing succinic anhydride as a main component with a cyclic ether containing ethylene oxide as a main component is carried out in the presence of a catalyst by introducing successively the cyclic ether into a reaction vessel containing the cyclic acid anhydride in a melting state or solution state. The rate per hour of introducing the cyclic ether is within the range of 3 to 90 parts by weight per 100 parts by weight of the cyclic acid anhydride, and the reaction vessel has an inside pressure within the range of atmospheric pressure to 50 kgf/cm.sup.2 as a gauge pressure.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: February 21, 1995
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hiroshi Itoh, Takashi Namba, Hiroya Kobayashi, Masashi Yukitake
  • Patent number: 5391698
    Abstract: The invention relates to phosphoric acid polyesters according to the formulae ##STR1## in which R is .dbd.CH.sub.2, .dbd.C.sub.2 H.sub.4 or .dbd.C.sub.3 H.sub.6 and m is 1 to 10 and n is 1 to 6.To prepare these phosphoric acid polyesters, the cyclic phosphoric acid ester 2,4,8,10-tetraoxa-3,9-dioxo-3,9-dihydroxy-phosphaspiro[5.5]-undecane is reacted with tris-hydroxyalkyl cyanurate or tris-hydroxyalkyl isocyanurate at temperatures of 120.degree. to 250.degree. C. in the presence of a catalyst for 2 to 12 hours, while mixing intensively.
    Type: Grant
    Filed: January 25, 1994
    Date of Patent: February 21, 1995
    Assignee: Hoechst Aktiengessellschaft
    Inventor: Horst Staendeke
  • Patent number: 5389721
    Abstract: A process for forming extended chain polyesters and block or graft polyesters or copolyesters which comprises the steps of (a) forming an intimate mixture of one or more polyesters, and an effective amount of one or more chain extension reagents, which are phosphorous (III)-containing compounds, and (b) heating said mixture for a time and at a temperature sufficient to form said extended chain, or graft or block copolyester or polyester; wherein the polyester used in step (a) contains no or substantially no substances which comprise elements from groups VA and VIA of the periodic table in elemental form; and wherein preferably, said polyesters conatain one or more elements belonging to groups IIA, IIIA, IVA, VB, IIB, IIIB, IVB, VIII and the lanthanides.
    Type: Grant
    Filed: May 27, 1994
    Date of Patent: February 14, 1995
    Assignee: AlliedSignal Inc.
    Inventor: Shaul M. Aharoni
  • Patent number: 5384184
    Abstract: A polyester block copolymer having an inherent viscosity of at least 0.6, which comprises (A) 30 to 90% by weight of polyester segments comprising a benzenedicarboxylic acid as the main acid component and a diol having 5 to 12 carbon atoms between the hydroxyl groups as the main glycol component and (B) 70 to 10% by weight of polyester segments comprising an aromatic dicarboxylic acid as the main acid component and ethylene glycol, trimethylene glycol, tetramethylene glycol or 1,4-cyclohexane dimethanol as the main glycol component, wherein (i) when a polyester having an inherent viscosity of at least 0.6 is formed by polycondensation of the components constituting the polyester segments (A), the melting point of the obtained polyester is lower than 50.degree. C. or the obtained polyester is amorphous, and (ii) when a polyester having an inherent viscosity of at least 0.
    Type: Grant
    Filed: September 28, 1993
    Date of Patent: January 24, 1995
    Assignee: Teijin Limited
    Inventors: Noritsugu Saiki, Toshitsugu Matsuki, Masayuki Hayashi
  • Patent number: 5382474
    Abstract: Disclosed is a process for producing polyethylene terephthalate fibers with reduced flammability which comprises the following steps:(a) condensating terephthalic acid and ethylene glycol in a mole ratio of from 1:1.1-1.5 at a temperature of from 180.degree.to 240.degree. C. in the presence of a catalyst;(b) adding a polyalkylene glycol phosphate ester;(c) polycondensating at a temperature of from 265.degree.-280.degree. C. under a pressure decreasing from 760 torr to less than 2 torr to form the polyethylene terepthalate; and(d) melt spinning fibers.
    Type: Grant
    Filed: September 24, 1992
    Date of Patent: January 17, 1995
    Assignee: BASF Corporation
    Inventors: Atish Adhya, Thomas F. Corbin, Robert L. Lilly
  • Patent number: 5370938
    Abstract: Disclosed are polyester adhesive compositions which exhibit increased melt viscosity and improved adhesion comprised of residues of terephthalic acid, ethylene glycol and diethylene glycol and having reacted therewith or copolymerized therein the residue of a phosphite ester compound and optionally containing a phenolic antioxidant. Also disclosed are articles coated with the polyester compositions and bonded laminate articles based on the compositions.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: December 6, 1994
    Assignee: Eastman Chemical Company
    Inventors: Alan W. White, Barry G. Pearcy, Marc A. Strand, Joey C. Carico
  • Patent number: 5369160
    Abstract: Disclosed is a thermoplastic polyamide with reduced flammability obtained by melt mixing a polyamide with a phosphate ester of the general formula: ##STR1## wherein n is a number of from 1 to 10;m is a number of from 0 to 3;x is a number of from 0 to 3;R is linear or branched C.sub.1 -to C.sub.18 -alkyl radical.
    Type: Grant
    Filed: September 24, 1992
    Date of Patent: November 29, 1994
    Assignee: BASF Corporation
    Inventors: Atish Adyha, Robert L. Lilly