Polyoxyalkylene Alcohol Moiety Patents (Class 560/91)
  • Patent number: 11180606
    Abstract: A polyester polyol of formula produced by a first polycondensation (a) of a sugar alcohol Z in C3 to C8 and two diacids Y and Y? which are the same or different in C4 to C36, and a second polycondensation (b) of the product produced in (a) with two diols X and X? which are the same or different in C2 to C12, the polymer including such a polyester polyol. Also, a method for producing the polyester polyols and the use thereof in foams, adhesives, coatings or elastomers of polyurethane or polyisocyanurate.
    Type: Grant
    Filed: August 24, 2017
    Date of Patent: November 23, 2021
    Assignees: TEREOS STARCH & SWEETENERS BELGIUM, CENTRE NATIONAL DE LA RECHERCHE SCIEN'I'IFIQUE, SOCIÉTÉ SOPREMA SAS, UNIVERSITÉ DE STRASBOURG
    Inventors: Pierre Etienne Bindschedler, Alexandru Sarbu, Stephanie Laurichesse, Remi Perrin, Pierre Furtwengler, Luc Avérous, Andreas Redl
  • Patent number: 8759565
    Abstract: Disclosed are processes to prepare monocarboxylic acid esters (mono- and/or diesters) of polytrimethylene ether glycol that are substantially free of residues from the catalyst used to produce the polytrimethylene ether glycol esters, as well as methods for their preparation and end uses thereof. The esters, such as the bis-2-ethylhexanoate esters, have uses as functional fluids.
    Type: Grant
    Filed: June 23, 2010
    Date of Patent: June 24, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Hari Babu Sunkara, Raja Hari Poladi, Gyorgyi Fenyvesi
  • Patent number: 8592623
    Abstract: Polyester polyols are produced from at least one carboxylic acid hydride and diethylene glycol by a process in which the formation of 1,4-dioxane is suppressed. These polyester polyols are useful for producing polyurethane (PUR) and polyisocyanurate (PIR) foams and metal composite elements containing these PUR or PIR foams.
    Type: Grant
    Filed: November 3, 2009
    Date of Patent: November 26, 2013
    Assignee: Bayer MaterialScience AG
    Inventors: Rolf Roers, Hartmut Nefzger, Erika Bauer, Johannes Van De Braak, Torsten Heinemann, Jürgen Schloβmacher
  • Patent number: 8367747
    Abstract: Novel bioabsorbable and/or biocompatible polyurethanes, polyureas, polyamideurethanes and polyureaurethanes with tunable physical, mechanical properties and hydrolytic degradation profiles are provided for use in biomedical applications such as stents, stent coatings, scaffolds, foams, and films. The disclosed polymers may be derived from biocompatible and/or bioabsorbable polyisocyanates. The present invention also relates to new and improved methods for the preparation of the biocompatible and/or bioabsorbable polyisocyanates.
    Type: Grant
    Filed: May 22, 2009
    Date of Patent: February 5, 2013
    Assignee: Bezwada Biomedical, LLC
    Inventor: Rao S. Bezwada
  • Publication number: 20120129966
    Abstract: The present invention relates to the production and use of polyester polyols produced from at least one aromatic dicarboxylic acid or an alkyl ester of an aromatic dicarboxylic acid or the anhydride of an aromatic dicarboxylic acid and at least one ?,?-diol, wherein the formation of 1,4-dioxane from diethylene glycol is largely suppressed by means of specific reaction management.
    Type: Application
    Filed: June 2, 2010
    Publication date: May 24, 2012
    Applicant: Bayer MaterialScience AG
    Inventors: Hartmut Nefzger, Erika Bauer, Johannes Van De Braak, Silvia Kasperek
  • Publication number: 20120116099
    Abstract: The present invention relates to a method of continuously conveying a liquid which is used as starting material in a chemical reaction by means of a displacement pump having physically separate forward-transport valves and a liquid-filled bidirectional flow line between displacement pump and forward-transport valves, wherein an auxiliary liquid which is a product or a starting material of the chemical reaction and has a melting point which is below the melting point or below the saturation temperature of the liquid to be conveyed is present in the bidirectional flow line. The present invention additionally provides for the use of a product formed by hydrogenation of an aromatic compound as auxiliary liquid for conveying an aromatic compound and also the use of an alcohol or an ester derived from alcohol and carboxylic acid as auxiliary liquid for conveying carboxylic acids or carboxylic acid derivatives.
    Type: Application
    Filed: July 6, 2010
    Publication date: May 10, 2012
    Applicant: BASF SE
    Inventors: Joachim Pfeffinger, Willi Gilcher, Juergen Morell
  • Patent number: 7863477
    Abstract: A polyester production process employing an esterification system that uses a distillation column to recover alcohol produced from an esterification zone and then utilizes the recovered alcohol to form a paste, which is recirculated back to the esterification zone with little or no cooling.
    Type: Grant
    Filed: March 8, 2007
    Date of Patent: January 4, 2011
    Assignee: Eastman Chemical Company
    Inventor: Bruce Roger DeBruin
  • Patent number: 7772417
    Abstract: Supported heterogeneous organotin catalysts of the formula X1, X2, or X3: wherein Z is a spacer group; Y is an insoluble phenyl-group containing copolymer; R1, R2, R3, R5, and R6 are independently selected from halogen, alkyl, alkylene, phenyl, vinyl, allyl, naphthyl, aralkyl, and Z; and R4 is alkyl, alkylene, phenyl, vinyl, allyl, naphthyl, or aralkyl.
    Type: Grant
    Filed: February 19, 2010
    Date of Patent: August 10, 2010
    Assignee: Chemtura Corporation
    Inventors: Uwe Schneider, Bernard Jousseaume, Karine Darriet, Thierry Toupance
  • Patent number: 7728097
    Abstract: A novel macromer or mixture thereof is described herein, comprising benzoyl isocyanate terminal moieties and at least two residues of a water-soluble polymer having a molecular weight ranging from 80 to 10,000 adjacent to the carbonyl group of the benzoyl isocyanate moieties, thereby forming at least two ester linkages in the macromer or mixture thereof. A method for making a diisocyanate macromer is also described herein.
    Type: Grant
    Filed: June 28, 2006
    Date of Patent: June 1, 2010
    Assignee: Ethicon, Inc.
    Inventors: Benjamin D. Fitz, Michael Justus, Christopher M. Westergom
  • Publication number: 20090137749
    Abstract: The invention relates to a method for producing low-acid polyalkylene terephthalate from which MPO can be advantageously manufactured. In certain embodiments, the acid content of commercially available polybutylene terephthalate (PBT) is reduced by adding a small amount of 1,4-butane diol (BDO) to a solution of the commercially available PBT in refluxing ortho-dichlorobenzene (oDCB) solvent.
    Type: Application
    Filed: October 23, 2008
    Publication date: May 28, 2009
    Inventors: Peter D. Phelps, Paul M. Andrusyszyn
  • Patent number: 7408077
    Abstract: The invention relates to novel compounds of the formula I, II; III or IV wherein the general symbols are as defined in claim 1. These compounds are useful as surface modifiers for polymers in order to improve resistance to fog formation or water and oil repellency.
    Type: Grant
    Filed: February 28, 2002
    Date of Patent: August 5, 2008
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Piero Piccinelli, Manuele Vitali, Andrea Landuzzi, Giovanni Da Roit, Primo Carrozza, Markus Grob, Nicola Lelli
  • Patent number: 7385075
    Abstract: A process is described for preparing esters of an acid component selected from among polybasic C4-C10 carboxylic acids and an alcohol component selected from among C3-C12 alkanols or from among C3-C12 alkanediols, the alkyl chain of which may have interruption by from 1 to 3 oxygen atoms, by a) heating at boiling point, in a reaction zone and in the presence of an esterification catalyst, a mixture essentially consisting of the acid component or of an anhydride thereof and of the alcohol component, b) using rectification to separate the vapor comprising alcohol and water into an alcohol-rich fraction and a water-rich fraction, and c) returning the alcohol-rich fraction into the reaction zone and conducting the water-rich fraction out of the process. The process is simple to carry out and permits rapid achievement of essentially quantitative conversion.
    Type: Grant
    Filed: November 13, 2001
    Date of Patent: June 10, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Disteldorf, Günther Golfier, Bernd Morsbach, Kurt Schwirten
  • Patent number: 7381354
    Abstract: Flame retardant formulations comprised of at least one bromine-containing polyol are produced by a process which comprises: A) heating a mixture formed from components comprised of (i) tetrabromophthalic anhydride, (ii) at least one aliphatic polyol, and (iii) at least one liquid straight chain aliphatic diester of a straight-chain alkane dicarboxylic acid to form an intermediate composition; and B) contacting all or a portion of the intermediate composition one or more times with (iv) at least one alkylene oxide that results in the formation of a liquid product formulation, and optionally, removing any excess alkylene oxide present; the amounts of (i), (ii), (iii), and (iv) used being proportioned to form a formulation having a bromine content of at least about 40 wt %, a viscosity at 25° C. of about 20,000 cps or less, and an acid number as determinable by aqueous sodium hydroxide titration and expressed in terms of potassium hydroxide, of less than about 1 milligram of KOH per gram of the formulation.
    Type: Grant
    Filed: May 21, 2007
    Date of Patent: June 3, 2008
    Assignee: Albemarle Corporation
    Inventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
  • Patent number: 7258823
    Abstract: Flame retardant formulations comprised of at least one bromine-containing polyol are produced by a process which comprises: A) heating a mixture formed from components comprised of (i) tetrabromophthalic anhydride, (ii) at least one aliphatic polyol, and (iii) at least one liquid straight chain aliphatic diester of a straight-chain alkane dicarboxylic acid to form an intermediate composition; and B) contacting all or a portion of the intermediate composition one or more times with (iv) at least one alkylene oxide that results in the formation of a liquid product formulation, and optionally, removing any excess alkylene oxide present; the amounts of (i), (ii), (iii), and (iv) used being proportioned to form a formulation having a bromine content of at least about 40 wt %, a viscosity at 25° C. of about 20,000 cps or less, and an acid number as determinable by aqueous sodium hydroxide titration and expressed in terms of potassium hydroxide, of less than about 1 milligram of KOH per gram of the formulation.
    Type: Grant
    Filed: May 20, 2004
    Date of Patent: August 21, 2007
    Assignee: Albemarle Corporation
    Inventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
  • Patent number: 7045564
    Abstract: A flame retardant formulation which is the combination of at least (1) at least one bromine-containing polyol flame retardant formed from the reaction of (a) tetrabromophthalic anhydride, (b) an aliphatic polyol, and (c) an epoxide, and (2) at least one aliphatic diester of an alkane dicarboxylic acid, with the proviso that the formulation has a viscosity at 25° C. of about 20,000 cps or less, and a bromine content of at least about 40 wt %. A flame retardant compound formed from A) tetrabromophthalic anhydride; B) diethylene glycol; C) at least one alpha-omega alkane diol, or at least one alpha-omega alkane diol and at least one aliphatic monool; and D) at least one alkylene oxide; with the proviso that the compound has a viscosity at 25° C. of about 60,000 cps or less, and a bromine content of at least about 43 wt %. Polymer compositions formed from (a) a polyurethane or a polyisocyanurate and (b) a formulation of the invention.
    Type: Grant
    Filed: August 29, 2003
    Date of Patent: May 16, 2006
    Assignee: Albemarle Corporation
    Inventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
  • Patent number: 6951954
    Abstract: A process for the continuous production of at least one of bis(3-hydroxypropyl) terephthalate and low molecular weight oligomers of 1,3-propanediol and terephthalic acid is disclosed. According to the process, preheated 1,3-propanediol (about 150° C. to about 200° C.) and preheated lower dialkyl esters of terephthalic acid (about 150° C. to about 220° C.) are combined in a mole ratio of about 1.2:1 to about 2.3:1 and fed to an ester exchange vessel where the mixture undergoes a continuous transesterification reaction. The liquid reaction mixture is continuously heated and mixed, at a temperature of about 215° C. to about 250° C., and a pressure of about 800 mm Hg to about 1,000 mm Hg. Gaseous reaction products are continuously separated from the liquid reaction mixture, and a stream of liquid reaction products containing bis(3-hydoxypropyl) terephthalate and low molecular weight oligomers of 1,3-propanediol and terephthalic acid is continuously removed from a base portion of the ester exchange vessel.
    Type: Grant
    Filed: February 11, 2000
    Date of Patent: October 4, 2005
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Carl J. Giardino, David B. Griffith, Chungfah Howard Ho, James M. Howell, Michelle Hoyt Watkins
  • Patent number: 6855844
    Abstract: Disclosed are polyester-ether polyols and their use in urethane prepolymers, urethane foams and non-foam urethane coatings, adhesives, sealants and/or elastomers. Methods for producing such polyester-ether polyols using double metal cyanide catalysts are disclosed, along with methods for producing urethane prepolymers. The polyester-ether polyols of the instant invention are preferably the reaction product of phthalic anhydride, diethylene glycol, and propylene oxide. These polyester-ether polyols are useful as either the primary polyol in urethane compositions or in combination with conventional auxiliary polyester- and/or polyether-based polyols. The polyester-ether polyols impart greatly improved solubility and compatibility to mixtures of either polyether and/or polyester polyols. The polyester-ether polyols of the instant invention are desirably of lower viscosity than their precursor intermediate polyester polyols and are generally soluble in either polyester- and/or polyether-based polyols.
    Type: Grant
    Filed: October 25, 2000
    Date of Patent: February 15, 2005
    Assignee: Stepan Company
    Inventors: Eric J. Geiger, Douglas K. Hillshaffer
  • Patent number: 6768021
    Abstract: Disclosed herein is an improved process for producing ethyl acetate comprising contacting acetic acid and ethanol in a reaction zone in the presence of an acid catalyst, distilling formed vapors and condensing to form an organic phase rich in ethyl acetate and an aqueous phase rich in water, separating the phases and further distilling each phase to obtain a final purified ethyl acetate product and a water stream low in organic components, the improvement comprising directing the organic phase from the first distillation to the reaction zone. An alternate embodiment involves directing at least a portion of the organic phase from the first distillation to a membrane separation unit which removes water and/or alcohol from the organic phase rich in ethyl acetate.
    Type: Grant
    Filed: December 22, 1999
    Date of Patent: July 27, 2004
    Assignee: Celanese International Corporation
    Inventors: Kimberly Ann Horan, Carl David Murphy, Russell Mark Stephens, R. Jay Warner, Kenneth Allen Windhorst
  • Patent number: 6642407
    Abstract: This invention provides a process for purifying the crude aromatic dicarboxylic acids produced by oxidation of dialkyl aromatic hydrocarbons and for using the purified acids in the preparation of polyethylene terephthalate, polyethylene naphthalate and other polyesters. The invention simplifies the manufacturing process by converting the crude aromatic acids into bis-glycol esters in an esterification reactor 4, from which the esterified partial oxidation impurities present in the oxidation product are removed by distillation in distillation tower 5. After removal of the volatile impurities, the dicarboxylic acid esters can separated by distillation in distillation tower 6 or by crystallization and converted to polyesters by polycondensation. The volatile impurities removed as overhead from tower 5 can be recycled as stream 16 to the oxidation reactor where they act as oxidation promoters thereby optionally allowing for a bromine-free oxidation process for dialkyl aromatic hydrocarbons.
    Type: Grant
    Filed: April 26, 2002
    Date of Patent: November 4, 2003
    Assignee: Exxon Mobil Chemical Patents Inc.
    Inventors: Krishna Kulai Rao, Russell D. Sellen, Xiaobing Feng, James Spanswick, William F. Huber, Jr.
  • Patent number: 6569352
    Abstract: Disclosed are polyester-ether polyols and their use in urethane prepolymers, urethane foams and non-foam urethane coatings, adhesives, sealants and/or elastomers. Methods for producing such polyester-ether polyols are disclosed, along with methods for producing urethane prepolymers. The polyester-ether polyols of the instant invention are preferably the reaction product of phthalic anhydride, diethylene glycol, and propylene oxide. These polyester-ether polyols are useful as either the primary polyol in urethane compositions or in combination with conventional auxiliary polyester- and/or polyether-based polyols. The polyester-ether polyols impart greatly improved solubility and compatibility to mixtures of either polyether and/or polyester polyols. The polyester-ether polyols of the instant invention are desirably of lower viscosity than their precursor intermediate polyester polyols and are generally soluble in either polyester- and/or polyether-based polyols.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: May 27, 2003
    Assignee: Stepan Company
    Inventors: Douglas K. Hillshafer, George Magnus
  • Publication number: 20020111518
    Abstract: Fluorinated multifunctional alcohols containing at least 3 primary hydroxyl groups are disclosed. Such alcohols allow for easy synthesis of multifunctional crosslinkers such as acrylates, epoxies and vinyl ethers. The multifunctional crosslinkers are used in fluorinated optical coating and waveguide compositions to increase curing speed and crosslinking density.
    Type: Application
    Filed: January 31, 2002
    Publication date: August 15, 2002
    Inventors: Fang Wang, Baopei Xu, Indira S. Pottebaum, Chuck C. Xu
  • Patent number: 6284811
    Abstract: A polyester-polyol being liquid at 40° C. and having a viscosity of not more than 10,000 mPa·s at 60° C., prepared by polycondensation of an acid component including at least one phthalic acid component selected from phthalic anhydride and o-phthalic acid, and an aliphatic polybasic acid, with a polyhydric alcohol; a process for preparing a polyurethane foam including reacting a polyisocyanate component with a polyol component including the polyester-polyol; a process for preparing an isocyanate prepolymer from a polyisocyanate component and a polyol component including the polyester-polyol; and a process for preparing a polyurethane foam including reacting an isocyanate prepolymer prepared from a polyisocyanate component and a polyol component including the polyester-polyol, with a polyol component. The resulting polyurethane foam shows remarkably improved physical properties such as tensile strength and tear strength, while having low density, acceptable appearance and texture.
    Type: Grant
    Filed: May 17, 2000
    Date of Patent: September 4, 2001
    Assignee: Kao Corporation
    Inventors: Minoru Sawai, Makoto Okubo, Kenichi Miyamoto, Kazunari Takemura, Masahiro Mori
  • Patent number: 6255523
    Abstract: The present invention relates to powder coating compositions which can be cured at low temperatures. The powder coating composition of the invention include a unique combination of a branched oligoester polyol and uretdione crosslinking agent which when cured results in a coating binder with desirable hardness, flexibility, solvent resistance, corrosion resistance, weatherability and gloss.
    Type: Grant
    Filed: September 18, 1998
    Date of Patent: July 3, 2001
    Assignee: McWhorter Technologies, Inc.
    Inventors: Kamlesh Pai Panandiker, John Michael Bronk, Franklin Paul Spitler
  • Patent number: 6100374
    Abstract: The process for preparing polyethylene naphthalate according to the invention is intended to obtain polyethylene naphthalate having a low impurity content from naphthalenedicarboxylic acid containing impurities.
    Type: Grant
    Filed: March 9, 1999
    Date of Patent: August 8, 2000
    Assignee: Mitsui Chemicals Inc.
    Inventors: Hiroshi Iwasaki, Satoshi Inoki, Hiromi Ueki
  • Patent number: 5907054
    Abstract: The present invention provides a process for the production of an ester of polyoxyalkylene glycol on an industrially favorable basis which comprises the ring opening polymerization of a cyclic ether in the presence of a carboxylic anhydride and a solid acid polymerization catalyst to obtain a polymer esterified at some or all of the ends thereof, wherein the water content in the reaction system is maintained at not more than 30 ppm by weight during the polymerization reaction.
    Type: Grant
    Filed: June 2, 1997
    Date of Patent: May 25, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Tohru Setoyama, Yoshio Kabata, Mitsuharu Kobayashi
  • Patent number: 5763642
    Abstract: Esterification of an ultra-low unsaturation polyoxy(higher)alkylene polyol with a dicarboxylic acid or reactive derivative thereof to form a poly(half ester) followed by capping the poly(half ester) with a capping agent capable of forming an amide linkage or ester linkage while retaining primary hydroxyl functionality, generates high primary hydroxyl content polyols with substantially retained hydrophile/lipophile balance and low polydispersity. Low color products having primary hydroxyl contents in excess of 80 equivalent percent may be routinely achieved.
    Type: Grant
    Filed: June 19, 1997
    Date of Patent: June 9, 1998
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Gangfeng Cai
  • Patent number: 5510447
    Abstract: This invention relates to a polymeric vehicle comprising a modified polymer containing covalently bonded mesogenic groups. The modified polymer may be used as the sole component of the polymeric vehicle for a coating to which may be added solvents and known additives to provide a formulated coating. The polymeric vehicle may further include other modified or unmodified polymers and cross-linking resins. The polymeric vehicle provides a coating binder and coating film of high hardness, flexibility and impact resistance.
    Type: Grant
    Filed: October 19, 1994
    Date of Patent: April 23, 1996
    Assignee: North Dakota State University
    Inventors: Frank N. Jones, Der-Shyang Chen, Adel F. Dimian, Daozhang Wang
  • 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: 5457241
    Abstract: This invention relates to the polyalk-1-enyl ethers having the formula ##STR1## which is the reaction product of a hydroxylated compound and an alk-1-enyloxy oxirane and to the process for preparing the polyalk-1-enyl ether product.
    Type: Grant
    Filed: January 5, 1994
    Date of Patent: October 10, 1995
    Assignee: ISP Investments Inc.
    Inventors: Jeffrey S. Plotkin, Kolazi S. Narayanan, Paul D. Taylor
  • Patent number: 5455025
    Abstract: Non-aqueous compositions for topical application comprising one or more active ingredients and a fatty alkoxylate ester emollient agent comprising a diester or triester of an aliphatic or aromatic tricarboxylic acid formed by reacting the acid with a stoichiometric excess of one or more polyalkoxylated fatty alcohols.
    Type: Grant
    Filed: April 12, 1994
    Date of Patent: October 3, 1995
    Assignee: Croda, Inc.
    Inventors: Abel G. Pereira, Kevin F. Gallagher, Phillip G. Abend, John C. Carson, Jr.
  • 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: 5440060
    Abstract: The demands on the properties of pigments, in particular in the areas of emulsion paints and printing inks, which are continuously becoming more specific made it necessary to develop selective and environmentally safe dispersing and emulsifying agents and coupling auxiliaries.The compounds according to the invention are alkoxylation products prepared from fatty amine dialkylenediamines which, if desired, are linked to give recurring structural units by means of esterification with dicarboxylic acids and in which, preferably, the hydroxyl end groups of these fatty amine alkylenediamine alkoxylates have been esterified with fatty acids, aromatic carboxylic acids and/or resin acids and any hydroxyl groups still present have been converted to the corresponding mono-ester-containing anionic radicals by means of dicarboxylic acids and sulfites.
    Type: Grant
    Filed: August 30, 1993
    Date of Patent: August 8, 1995
    Assignee: Hoechst AG
    Inventors: Heinz Uhrig, Albert Munkel
  • Patent number: 5397810
    Abstract: The present invention relates to a novel polyol obtained by using a specified polyhydric alcohol, polyoxyalkylene polyol, aliphatic amine and/or alkamlamine as a raw material and adding an organic polycarboxylic acid or its anhydride and an alkylene oxide; a polyurethane resin prepared from said novel polyol and an organic polyisocyanate; a rigid polyurethane foam prepared by using a hydrochlorofluorocarbon or hydrofluorocarbon foaming agent which has very low public hazards; and a composite utilizing thereof.The production of rigid polyurethane foam by using the polyol of the invention can be carried out in good operation efficiency and low public hazards. Additionally, properties of the foam thus obtained is equivalent to those of rigid polyurethane foams obtained by using conventional chlorofluorocarbons. Consequently, the rigid polyurethane foam of the invention is very useful for insulation materials and structural insulation materials.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: March 14, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Masayuki Kimura, Toshio Nozawa, Masahiko Hashiba
  • Patent number: 5364956
    Abstract: The compound described in the present invention is represented by the following general formula: R.sub.1 (OCH.sub.2 CH.sub.2).sub.n O(COACOOXO).sub.m COACO(OCH.sub.2 CH.sub.2).sub.k OR.sub.2 wherein A is C.sub.2 -C.sub.4 alkylene group or a residual group of aromatic dicarboxylic acid, namely a group formed by removing two carboxylic groups from an aromatic dicarboxylic acid,X is straight or branched chain alkylene group, a residual group of glycols (namely a group formed by removing two hydroxyl groups from a glycol) selected from the group consisting of diethylene glycol, triethylene glycol, dipropylene glycol, and tripropylene glycol, or a residual group of thiodiethanol,n is 1 to 3,R.sub.1 is selected from the group consisting of C.sub.1 -C.sub.10 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.8 alkyl or benzyl,m is 0 to 13 andk is 0 to 3.
    Type: Grant
    Filed: November 18, 1992
    Date of Patent: November 15, 1994
    Inventor: Satoshi Matsumoto
  • Patent number: 5360900
    Abstract: Two methods for preparing polyester-polyether polyols from polyalkylene terephthalates are disclosed. The first method comprises reacting the polyalkylene terephthalate with a solution of low molecular weight polyols and ethoxylated methyl glucoside at a suitable temperature, generally between about 370.degree. and 450.degree. F., and under vacuum distillation.The second method comprises dissolving the polyalkylene terephthalates in a mixture of low molecular weight polyols at a suitable temperature and under vacuum distillation to form the polyester polyol component. The polyether polyol component is made by reacting ethoxylated methyl glucoside with an alkylene oxide in the presence of a suitable catalyst. The final product is made by blending about 80-95% by weight of the polyester component with about 5-20% by weight of the polyether component.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: November 1, 1994
    Assignee: Oxid, Inc.
    Inventors: Alberto DeLeon, David J. Shieh
  • Patent number: 5332860
    Abstract: Polyurethane foams having improved retention of insulative properties can be prepared using one or more of two novel polyols. One of the polyols is a polyether prepared by reacting a monoepoxide with a compound having the general formula: ##STR1## wherein X is H, Li, Na, K; A is N, S or O; L is a covalent bond or a connecting group having from 1 to 10 carbons; M is any group capable of reacting with an ethylene oxide molecule in the presence of a basic catalyst; and J is an integer from 2 to 8. The other polyol is prepared by (1) admixing ethylene carbonate and one or more hydroxyl functional compounds under reaction conditions sufficient to react the ethylene carbonate and the hydroxyl functional compounds to produce a polyol precursor, and (2) admixing the polyol precursor with diethylene glycol and an anhydride, a dicarboxylic acid, a tricarboxylic acid or mixtures thereof, optionally in the presence of a catalyst.
    Type: Grant
    Filed: June 29, 1993
    Date of Patent: July 26, 1994
    Assignee: The Dow Chemical Company
    Inventors: Douglas R. Moore, Warren A. Kaplan, Ricky L. Tabor, Alan K. Schrock
  • Patent number: 5332859
    Abstract: Described is a batchwise process for producing tetrabromophthalic diester flame retardants having consistent product characteristics.
    Type: Grant
    Filed: November 3, 1992
    Date of Patent: July 26, 1994
    Assignee: Great Lakes Chemical Europe, Ltd.
    Inventor: Brian Tarbit
  • Patent number: 5302377
    Abstract: Fatty alkoxylate esters which are diesters or triesters of an aliphatic or aromatic dicarboxylic or tricarboxylic acid formed by reacting the acid with a stoichiometric excess of one or more polyalkoxylated fatty alcohols. Compositions for topical application are also disclosed including one or more active ingredients, water and an emollient agent of the fatty alkoxylate esters of the present invention.
    Type: Grant
    Filed: April 2, 1992
    Date of Patent: April 12, 1994
    Assignee: Croda, Inc.
    Inventors: Abel G. Pereira, Kevin F. Gallagher, Phillip G. Abend, John C. Carson, Jr.
  • Patent number: 5286835
    Abstract: Vinyl ether terminated ester oligomers having a range of molecular weights are prepared by reacting a vinyl ether terminated polybasic ester with a polyol in the presence of a catalyst. Continual removal of a hydroxy monovinyl ether avoids formation compounds containing acetal moieties. Alternatively, a polybasic ester is chain extended with a polyol with continual removal of the alcohol by-product. Then, the terminal ester moieties are end capped with a monohydroxy vinyl ether. The oligomers have application in coatings and the like.
    Type: Grant
    Filed: August 24, 1992
    Date of Patent: February 15, 1994
    Assignee: Allied-Signal Inc.
    Inventors: George D. Green, James R. Snyder, Darryl K. Barnes
  • Patent number: 5219479
    Abstract: Compounds of general formula (I), wherein R.sup.1 is hydrogen, C.sub.1-4 alkyl or a group of formula (II): --O(CH(R.sup.10)CH.sub.2 O).sub.n R.sup.20, R.sup.2 is hydrogen or a group of formula (III): --O(CH(R.sup.11)CH.sub.2 O).sub.m R.sup.21, R.sup.3 is a group of formula (IV): --(CH(R.sup.12)CH.sub.2 O).sub.p R.sup.22, and R.sup.4 is a group of formula (V): --(CH(R.sup.13)CH.sub.2 O).sub.r R.sup.23, where R.sup.10, R.sup.11, R.sup.12 and R.sup.13 each is hydrogen or CH.sub.3, R.sup.20 R.sup.21, R.sup.22 and R.sup.23 each is an acyl moiety of a polycarboxylic acid, and n, m, p and r each is an integer from 1 to 15; q is 1 or 2; with the provisos that if q is 2, then the 2 groups R.sup.1 may be the same or different and the 2 groups R.sup.2 may be the same or different; and, if one or more of the groups R.sup.20, R.sup. 21, R.sup.22, and R.sup.23 is an acyl moiety of a polycarboxylic acid group, then 0-3 of the remaining carboxy groups of the polycarboxylic acid form the acyl function(s) of a moiety R.sup.
    Type: Grant
    Filed: May 21, 1991
    Date of Patent: June 15, 1993
    Assignee: Esti Chem A/S
    Inventors: Thomas Mathiesen, Jan W. Jensen
  • Patent number: 5204454
    Abstract: Prepolymer polyols containing mesogenic moieties useful as reactants for the preparation of resinous materials are disclosed. Synthesized by condensing a polyether polyol with bifunctional mesogenic diacids, or diesters, the compounds of the invention are characterized by their reasonably low melt temperature which renders them suitable as additive materials in polymeric molding compositions and as precursors for the preparation of resinous materials.The liquid crystalline properties of the prepolymers of the invention were found to depend on the type and molecular weight of the glycols and on the molar ratio between the glycols and the mesogenic reactant.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: April 20, 1993
    Assignee: Miles Inc.
    Inventors: Randall A. Rodenhouse, Dittmar K. Nerger, Douglas A. Wicks
  • Patent number: 5116897
    Abstract: Described is a composition imparting antistatic properties to polyamide materials and of the general formula: ##STR1## wherein R is a C.sub.1-9 alkyl group or hydrogen, Z is a difunctional chain modifier group, R' is a C.sub.1-4 alkyl group or hydrogen and x and y are between about 10 and about 50.
    Type: Grant
    Filed: June 27, 1990
    Date of Patent: May 26, 1992
    Assignee: BASF Corporation
    Inventor: Wendel L. Burton
  • Patent number: 5087731
    Abstract: A process of alkoxycarbonylation making use of a new catalyst consisting of a palladium-phosphine complex, the phosphine having a pKa greater than or equal to 7, a chlorinated aromatic compound, carbon monoxide and an alcohol.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: February 11, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Huser, John Osborn
  • Patent number: 5068395
    Abstract: A process is disclosed for preparing polymeric plasticizers from polyethylene terephthalate which comprises reacting a trimellitic acid polyester ether with polyethylene terephthalate to prepare a nonlinear copolymer with hydroxyl functionality which is then reacted with a fatty acid of from 12 to 18 carbon atoms. The resulting composition has excellent properties as a polymeric plasticizer for polyvinylchloride resin.
    Type: Grant
    Filed: April 25, 1990
    Date of Patent: November 26, 1991
    Assignee: Amoco Corporation
    Inventor: Oscar M. Bathe
  • Patent number: 5015759
    Abstract: A process for increasing the direct esterification reaction rate between a diacid and 1,4-butanediol and for directly esterifying greater than 95% of the acid ends of the diacid by mixing in any order the diacid, the 1,4-butanediol and a catalyst compound selected from organo-titanium, organo-tin, and organo-zirconium compounds, to form a reaction mixture wherein the ratio of diol:diacid is at least 2:1 and then reacting the reaction mixture at an average temperature ranging between 190.degree. C. to 200.degree. C. for a period of time no longer than sixty minutes. The same process may be followed substituting ethylene glycol for 1,4-butanediol, provided the catalyst compound is added neat, further provided that the average reaction temperature ranges from 190.degree. C. to 200.degree. C., and also provided that the reaction mixture be reacted for a period of time no longer than seventy minutes.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: May 14, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: David J. Lowe
  • Patent number: 4943626
    Abstract: Polyether active hydrogen compounds having at least two terminal active hydrogen groups on primary carbon atoms are prepared by (a) forming polyoxyalkylene molecules each having at least one active hydrogen precursor, (b) linking at least two of the polyoxyalkylene molecules, and (c) converting the active hydrogen precursor groups to active hydrogen groups on primary carbon atoms. The polyoxyalkylene molecule is formed by exposing a reaction mixture comprising at least one alkylene oxide and at least one protective initiator to conditions effective for the polymerization of the alkylene oxides. Linking is accomplished at polyether chain ends distal to the protected active hydrogen precursor groups, such that the active hydrogen precursors remain on the linked polyether chains until they are converted to active hydrogen groups.
    Type: Grant
    Filed: July 29, 1988
    Date of Patent: July 24, 1990
    Assignee: The Dow Chemical Company
    Inventors: James E. McGrath, Youngtai Yoo, Robert B. Turner, Diane M. Lewis
  • Patent number: 4940696
    Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjunctive tissues.
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: July 10, 1990
    Assignee: Centre International de Recherches Dermatologioues (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 4937307
    Abstract: These low viscosity polyesters and their products, such as urethanes produced with organic polyisocyanate(s) alone or plus a reactive diluent, such as a glycol or polyester glycols are uniquely useful for coatings, liquid coatings and as an adhesive for films and rubbers. These copolyesters are highly viscous at 24.4.degree. C. but at 40.degree. to 60.degree. C. they are thin enough to be intimately mixed with reactants such as an organic polyisocyanate or epoxy resin and diluents without need to use solvents which pollute the atmosphere.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: June 26, 1990
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Daniel A. Chung
  • Patent number: 4902816
    Abstract: Polyols containing polyether and polyester moieties, based on phthalic acid are described. A phthalic acid derivative is reacted with a polyether polyol to give the novel polyols which are useful not only in polyisocyanurate foams, but also polyurethane foams as well. The phthalic acid derivative may be phthalic acid, phthalic anhydride and an ester of phthalic acid, for example. The polyester polyol is made from an initiator selected from the group consisting of alkanolamines, alkyleneamines, arylamines, sucrose, glycerin, sorbitol, .alpha.-methylglucoside, .beta.-methylglucoside, and mixtures thereof. The polyester polyol may be made by alkoxylating the initiators.
    Type: Grant
    Filed: March 28, 1988
    Date of Patent: February 20, 1990
    Assignee: ARCO Chemical Technology, Inc.
    Inventor: Kenneth G. McDaniel
  • Patent number: RE34805
    Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjunctive tissues.
    Type: Grant
    Filed: July 10, 1992
    Date of Patent: December 6, 1994
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon