Of Ester Of Polyoxy Alcohols Patents (Class 560/79)
  • Patent number: 8299281
    Abstract: Provided are processes for making, and processes for using triglycerides as plasticizers. Mixed triglyceride plasticizers can be produced by recovery of linear or branched C4 to C13 aldehydes from a hydroformylation product, oxidation to the acid with oxygen and/or air, recovery of the resulting acid, and esterification with a crude glycerol, wherein the total carbon number of the triester groups is from 20 to 25 for greater than or equal to 45 wt % of the plasticizer. The product selectivity obtained from esterifying with crude glycerol is comparable to that of esterifying with pure glycerol. Such plasticizers can be phthalate-free and provide outstanding properties including a suitable melting or glass transition or pour point, low volatility, increased compatibility, and excellent low temperature properties in a range of polymeric resins.
    Type: Grant
    Filed: March 16, 2010
    Date of Patent: October 30, 2012
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Jihad Mohammed Dakka, Edmund J Mozeleski, Lisa Saunders Baugh
  • Patent number: 7511081
    Abstract: The present invention relates to a recycling method of a mixed waste of polyester and polyamide (hereinafter, referred to as “mixed waste”) in which polyesters including polyethylene terephthalate and polyamides are inseparable from one another. In accordance with the recycling method of the present invention, it is possible to prepare a solid block polymer having an acid value of 1 to 150 mgKOH/g, a weight average molecular weight of 3,000 to 50,000 and a softening point of 10 to 150° C., or a liquid polyester-amide block polymer composition having good compatibility, solubility and dispersibility. In addition, the polymer having an acid value of more than 20 mgKOH/g is reacted with a basic compound to form a neutralized salt which is then used to prepare a water-soluble polyester-amide block polymer composition.
    Type: Grant
    Filed: March 24, 2005
    Date of Patent: March 31, 2009
    Inventors: Do-Gyun Kim, Hyo-Sung Kim
  • 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: 7329772
    Abstract: A method of making a hindered phenolic antioxidant is disclosed wherein the method comprises: reacting an ester of the formula: wherein R1, R2, and R3 are independently selected alkyl groups and n is 0, 1, or 2, with an aliphatic polyhydroxyl alcohol of the general formula R(OH)n wherein R is an aliphatic group of from 2 to about 12 carbon atoms and n is an integer of from 2 to 7, provided that one hydroxyl is primary and the others are secondary or tertiary, in the presence of a strong acid catalyst; then, neutralizing the strong acid catalyst with an overbased detergent; and isolating the hindered phenolic antioxidant after the neutralization step.
    Type: Grant
    Filed: April 29, 2004
    Date of Patent: February 12, 2008
    Assignee: Crompton Corporation
    Inventor: John R. Baranski
  • Patent number: 7323289
    Abstract: Novel anti-reflective coatings comprising small molecules (e.g., less than about 5,000 g/mole) in lieu of high molecular weight polymers and methods of using those coatings are provided. In one embodiment, aromatic carboxylic acids are used as the chromophores, and the resulting compounds are blended with a crosslinking agent and an acid. Anti-reflective coating films prepared according to the invention exhibit improved properties compared to high molecular weight polymeric anti-reflective coating films. The small molecule anti-reflective coatings have high etch rates and good via fill properties. Photolithographic processes carried out with the inventive material result in freestanding, 110-nm profiles.
    Type: Grant
    Filed: October 6, 2003
    Date of Patent: January 29, 2008
    Assignee: Brewer Science Inc.
    Inventors: Charles J. Neef, Mandar Bhave, Michelle Fowler, Michelle Windsor
  • 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: 7022259
    Abstract: A liquid crystal compound with high helical twisting power, a method for preparing the same, and a liquid crystal composition containing the same. The liquid crystal compounds include cyclic group chain structures similar to the liquid crystal to serve as the core structure, and multi-ring structures of natural alcohol with optical activity, such as alcoholates of terpenol, borneol, cinchonidine, quinine, or derivatives thereof. As a result, the liquid crystal composition containing the liquid crystal compounds can filter out light of specific wavelengths from incident light due to optical activity and high helical twisting power thereof.
    Type: Grant
    Filed: September 30, 2003
    Date of Patent: April 4, 2006
    Assignee: Industrial Technology Research Institute
    Inventors: Dao-Hung Lee, Ding-Jen Chen, Kung-Lung Cheng
  • 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: 6740686
    Abstract: The invention concerns a method for making a polyurethane foam by reacting at least a polyester polyol with at least a polyisocyanate in the presence of a foaming agent and a catalytic agent, such a polyester polyol having been previously obtained by reacting a reactive acid A comprising at least an aliphatic or aromatic polyacid with functionality not less than 2 with at least a polyol P2 with functionality equal to 2 and at least an aliphatic or aromatic polyacid with functionality not less than 2 with at least a polyol P2 with functionality equal to 2 and at least a polyol P3 with functionality not less than 3, being thereafter called AP2P3, wherein the catalytic agent at least partly consists of at least one amine polyester polyol AP2P3, wherein at least part of polyol P3 consists of at least a polyoxyalkylene polyalkanolamine having at least a tertiary amine function, the alkanol radicals of said polyalkanolamine being C1-C6, the alkylene oxide units being C2-C4 and the statistical mean of the number N o
    Type: Grant
    Filed: November 27, 2000
    Date of Patent: May 25, 2004
    Assignee: Crompton Corporation
    Inventors: Denis Ghesquiere, Remy Dumont
  • Patent number: 6667416
    Abstract: To provide a method for producing polyester polyol that can provide a simple process to produce extensively improved production efficiencies and also produce the polyester polyol of stable in quality, an apparatus for producing the polyester polyol produced by the method, a polyester polyol produced by the method, and a polyurethane foam obtained by use of the polyester polyol produced by the method, polyethylene terephthalate and raw polyol are allowed to react in a reaction vessel to produce polyester polyol and also ethylene glycol which is a by-product of the reaction is distilled off and the distillate is modified in a modifying vessel so that it can have a predetermined hydroxyl value and then is fed to the reaction vessel again as the raw glycol, to thereby produce the polyester polyol.
    Type: Grant
    Filed: July 26, 2001
    Date of Patent: December 23, 2003
    Assignee: Mitsui Takeda Chemicals, Inc.
    Inventors: Kouichi Murayama, Katsumi Inaoka, Takashi Kumaki
  • 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: 6582626
    Abstract: A polymerizable compound represented by formula (I): wherein Q1 and Q2 each independently represent a hydrogen atom or a methyl group; p and q each independently represent an integer of 2 to 18; X1 and X2 each independently represent a single bond, —O—, —COO— or —OCO—; L1 represents —COO— or —OCO—; L2 represents —CH2CH2COO— or —CH2CH2OCO—; and Y1, Y2 and Y3 each independently represent a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkanoyl group having 2 to 7 carbon atoms, a cyano group or a halogen atom. Also disclosed are a polymerizable liquid crystal composition containing the compound, and an optically anisotropic medium produced from the composition.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: June 24, 2003
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Hiroshi Hasebe, Sadao Takehara, Kiyofumi Takeuchi
  • 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
  • Patent number: 6407201
    Abstract: The present invention provides a plasticizer compound having the general formula: in which n=1 to 3, R represents a C2-C8 straight or branched aliphatic hydrocarbon chain or C6-C10 aromatic or cycloaliphatic group, and R′ and R″ are each independently a branched oxyalkylene chain represented by the chemical formula C8H16O and by the chemical structures: The present invention is also directed to a coverstock formulation comprising the above-plasticizer compound.
    Type: Grant
    Filed: August 21, 2000
    Date of Patent: June 18, 2002
    Assignee: Bayer Corporation
    Inventors: Ronald P. Taylor, Jeffrey A. Dodge, Hartmut Nefzger
  • Publication number: 20020035166
    Abstract: To provide a method for producing polyester polyol that can provide a simple process to produce extensively improved production efficiencies and also produce the polyester polyol of stable in quality, an apparatus for producing the polyester polyol produced by the method, a polyester polyol produced by the method, and a polyurethane foam obtained by use of the polyester polyol produced by the method, polyethylene terephthalate and raw polyol are allowed to react in a reaction vessel to produce polyester polyol and also ethylene glycol which is a by-product of the reaction is distilled off and the distillate is modified in a modifying vessel so that it can have a predetermined hydroxyl value and then is fed to the reaction vessel again as the raw glycol, to thereby produce the polyester polyol.
    Type: Application
    Filed: July 26, 2001
    Publication date: March 21, 2002
    Inventors: Kouichi Murayama, Katsumi Inaoka, Takashi Kumaki
  • Patent number: 6329535
    Abstract: A process for preparing esterified chroman compounds from 2,6,6-trimethylcylohex-2-ene-1,4-dione, wherein the esterified intermediates are reacted directly to give the desired chroman derivatives without an additional purification step.
    Type: Grant
    Filed: October 20, 2000
    Date of Patent: December 11, 2001
    Assignee: Degussa Dental GmbH & Co. KG
    Inventors: Horst Weigel, Steffen Krill, Hans Joachim Hasselbach, Klaus Huthmacher
  • Patent number: 6103924
    Abstract: Preparation of 2,3,5-trimethylhydroquinone diesters by rearrangement of 2,6,6-trimethylcyclohex-2-ene-1,4-dione (4-oxo-isophorone, ketoisophorone) in the presence of a solid, acid catalyst and an acylating agent, for example carboxylic acid anhydrides or carboxylic acid halides. The 2,3,5-trimethylhydroquinone diester may then optionally be saponified to the free 2,3,5-trimethylhydroquinone, which is a valuable building block in the synthesis of vitamin E.
    Type: Grant
    Filed: April 21, 1999
    Date of Patent: August 15, 2000
    Assignee: Degussa-Huls AG
    Inventors: Nongyuan Shi, Mario Scholz, Steffen Hasenzahl, Horst Weigel, Bernd Drapal, Ralph McIntosh, Hans J. Hasselbach, Klaus Huthmacher
  • 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: 5908956
    Abstract: This method provides trimethylhydroquinone diester by using a recyclable catalyst which shows high activity and operability in the reaction, while reducing the risk of corrosion of the reactor. The method for the production of 2,5,6-trimethylhydroquinone diester comprises reacting 2,6,6-trimethylcyclohexe-2-en-1,4-dione with an acylating agent in the presence of a solid catalyst. The acylating agent includes a C.sub.2-4 carboxylic acid anhydride (e.g. acetic anhydride) and a C.sub.2-4 carboxylic acid halide (e.g. acetyl chloride). The solid catalyst includes a solid acid catalyst (e.g. strongly or super-strongly acidic ion exchange resin, compound oxide, zeolite, heteropoly acid).
    Type: Grant
    Filed: December 17, 1997
    Date of Patent: June 1, 1999
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Ikuo Takahashi, Masahiro Chikamori
  • Patent number: 5530128
    Abstract: Compounds of formula (1) are described wherein R represents a --CONHOH, carboxyl, carboxyl ester, or --P(O)(X.sup.1 R.sup.8)X.sup.2 R.sup.9, where X.sup.1 and X.sup.2 are the same or different and each is oxygen or sulphur, R.sup.8 and R.sup.9 are the same or different and each represents hydrogen or an optionally substituted alkyl, aryl or aralkylthioalkyl group; R.sup.2 represents an optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, aralkoxy, or aralkylthio group, or an amino, substituted amino, carboxyl, or carboxyl ester group; R.sup.3 represents hydrogen or alkyl; R.sup.4 represents hydrogen or alkyl; R.sup.5 represents an optionally substituted alkyl or alkenyl group optionally interrupted by one or more --O-- or --S-- atoms or --N(R.sup.7)-- groups, where R.sup.7 is a hydrogen atom or a C.sub.1-6 alkyl group, or --(Alk).sub.n R.sup.6 where Alk is an alkyl or alkenyl group optionally interrupted by one or more --O-- or --S-- atoms or --N(R.sup.
    Type: Grant
    Filed: February 2, 1994
    Date of Patent: June 25, 1996
    Assignee: Celltech Therapeutics Limited
    Inventors: John R. Porter, John R. Morphy, Thomas A. Millican, Nigel R. A. Beeley
  • Patent number: 5414107
    Abstract: A process for recycling by-products produced from a process for the manufacture of polyethylene terephthalate is disclosed. The process includes the steps of: (a) providing ethylene glycol distillation bottoms from an ethylene glycol recovery unit associated with the manufacture of polyethylene terephthalate, the bottoms containing an alkali metal organic salt produced during the manufacture of polyethylene terephthalate, the alkali metal organic salt being in excess of about 100 ppm of the bottoms; (b) stripping the alkali metal from the organic acid by use of a strong acid; and (c) depolymerizing the organic acid.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: May 9, 1995
    Assignee: Hoechst Celanese Corporation
    Inventor: Brad L. Smith
  • Patent number: 5413681
    Abstract: A process useful for the recovery of terephthalic acid and ethylene glycol from poly(ethylene terephthalate) or its copolymers. The process is economical, beneficial to the environment and provides polymer grade terephthalic acid and ethylene glycol from post-consumer resin. The process is a six-step process including: (1) contacting a resin containing poly(ethylene terephthalate) with water at elevated temperature and pressure, (2) cooling the resulting mixture to provide a solid portion containing terephthalic acid and a liquid portion containing ethylene glycol, (3) recovery of the ethylene glycol from the liquid portion by distillation, (4) recovery of the terephthalic acid by heating the solid portion in the presence of water vapor at elevated temperature to produce a vapor containing terephthalic acid and water, (5) cooling terephthalic acid water vapor mixture to a temperature below the dew point of terephthalic acid and (6) collecting the polymer grade terephthalic acid.
    Type: Grant
    Filed: November 15, 1993
    Date of Patent: May 9, 1995
    Assignee: Eastman Chemical Company
    Inventors: Gerald C. Tustin, Thomas M. Pell, Jr., David A. Jenkins, Mary T. Jernigan
  • 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: 5328982
    Abstract: Ester bonds are hydrolyzed in the conversion of substantially amorphous polyesters to their monomeric components, by being contacted with a mixture of (a) an alcohol, such as methanol, or glycol, (b) a polar aprotic solvent such as N-methyl-pyrrolidone or dimethyl sulfoxide and (c) an alkoxide or hydroxide such as sodium hydroxide.
    Type: Grant
    Filed: November 2, 1992
    Date of Patent: July 12, 1994
    Assignee: Eastman Chemical Company
    Inventors: George W. Tindall, Randall L. Perry, Art T. Spaugh, Jr.
  • Patent number: 5319128
    Abstract: A process for the production of terephthalate diesters having the following formula (I). ##STR1## Substituents R and R' are the same or different and represent a straight chain, branched or cyclic aliphatic group, an aromatic group, an alkaryl group or an aralkyl group, each group having from 6 to 20 carbon atoms. The process involves reacting a terephthalate polyester with a high molecular weight alcohol or a mixture of high molecular weight alcohols each having from 6 to 20 carbon atoms, in the presence of a catalyst and recovering the desired compound according to formula (I). This process is particularly useful for recycling scrap terephthalate polyester products such as those produced from polyethylene terephthalate (PET), crystallized polyethylene terephthalate (CPET), glycol-modified polyethylene terephthalate copolyester (PETG), polybutylene terephthalate (PBT), polycyclohexanedimethylene terephthalate (PCT), as well as the acid- and glycol-modified copolyesters of PCT, respectively PCTA and PCTG.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: June 7, 1994
    Assignee: Synergistics Industries, Ltd.
    Inventors: Louis Dupont, Ved P. Gupta
  • Patent number: 5101064
    Abstract: A process for the production of terephthalate diesters having the following formula (I). ##STR1## Substituents R and R' are the same or different and represent a straight chain, branched or cyclic aliphatic group, an aromatic group, an alkaryl group or an aralkyl group, each group having from 6 to 20 carbon atoms. The process involves reacting a terephthalate polyester with a high molecular weight alcohol or a mixture of high molecular weight alcohols each having from 6 to 20 carbon atoms, in the presence of a catalyst and recovering the desired compound according to formula (I). This process is particularly useful for recycling scrap terephthalate polyester products such as those produced from polyethylene terephthalate (PET), crystallized polyethylene terephthalate (CPET), glycol-modified polyethylene terephthalate copolyester (PETG), polybutylene terephthalate (PBT), polycyclohexanedimethylene terephthalate (PCT), as well as the acid- and glycol-modified copolyesters of PCT, respectively PCTA and PCTG.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: March 31, 1992
    Assignee: Synergistics Industries Limited
    Inventors: Louis Dupont, Ved P. Gupta
  • Patent number: 5045122
    Abstract: Ester bonds are hydrolyzed, such as in the conversion of polyesters to their monomeric components, by being contacted with a mixture of (a) an alcohol, such as methanol, or glycol, (b) a polar aprotic solvent such as N-methyl-pyrrolidone or dimethyl sulfoxide and (c) an alkoxide or hydroxide such as sodium hydroxide.
    Type: Grant
    Filed: December 14, 1989
    Date of Patent: September 3, 1991
    Assignee: Eastman Kodak Company
    Inventors: George W. Tindall, Randall L. Perry
  • Patent number: 4929749
    Abstract: A process for the production of terephthalate esters having the following general formula (I). ##STR1## Substituents R and R' are the same or different and represent a straight chain or branched alkyl group having from 6 to 15 carbon atoms. The process comprises reacting a terephthalate polyester with a high molecular weight alcohol or mixture of high molecular weight alcohols in the presence of a catalyst and recovering the desired compound according to formula (I). This process is particularly useful for recycling scrap terephthalate polyesters such as polyethylene terephthalate and polybutylene terephthalate.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: May 29, 1990
    Assignee: Synergistics Industries, Limited
    Inventors: Ved P. Gupta, Louis A. DuPont
  • Patent number: 4876378
    Abstract: A process for the formation and recovery of dialkyl naphthalene-2,6-dicarboxylates from poly-(alkylene naphthalene-2,6-dicarboxylate) polyesters. Alcoholysis of poly(ethylene naphthalene-2,6-dicarboxylate) in the presence of a transesterification catalyst on cooling yields solid dialkyl naphthalene-2,6-dicarboxylate which may be collected by filtration and further purified by recrystallization from xylenes. Novel alkyl hydroxyalkyl naphthalene-2,6-dicarboxylate compounds may be isolated from the filtrate and either reconverted to polyester or further alcoholized to dialkyl naphthalene-2,6-dicarboxylate.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: October 24, 1989
    Assignee: Eastman Kodak Company
    Inventor: Dale E. Van Sickle
  • Patent number: 4868324
    Abstract: Crude diphenyl phthalates, including isomeric mixtures thereof which are prepared by reacting mixtures of isophthalic and terephthalic acids with phenol, preferably in the presence of an organotitanate, organozirconate, or organostannate catalyst, are purified by dissolving the crude phthalate in an organic solvent, contacting the resulting solution with dilute aqueous alkali to neutralize the ester, separating the resulting oil and aqueous phases, and thereafter recovering from the oil phase a purified diaryl phthalate of reduced color and low acidity.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: September 19, 1989
    Assignee: Celanese Engineering Resins, Inc.
    Inventors: A. Lee Stautzenberger, Ellen A. Langford, Edward E. Quick
  • Patent number: 4754053
    Abstract: Bis(2-ethyl-1-hexyl) tetrabromophthalate produced by the reaction of tetrabromophthalic anhydride with 2-ethyl-1-hexanol in the presence of titanium isopropoxide catalyst may be purified by contacting the reaction mixture with sodium carbonate decahydrate with agitation for a time and at a temperature sufficient to enhance product quality, followed by isolation of bis(2-ethyl-1-hexyl) tetrabromophthalate.
    Type: Grant
    Filed: May 12, 1987
    Date of Patent: June 28, 1988
    Assignee: Great Lakes Chemical Corporation
    Inventors: Rastko I. Mamuzic, Bhabatosh Bhattacharya
  • Patent number: 4745211
    Abstract: A process for preparation of a purified bis(2-hydroxyethyl) ester of 2,6-naphthalenedicarboxylic acid wherein 2,6-naphthalenedicarboxylic acid is reacted with a catalyst comprised of a tertiary amine and a titanium-containing compound in order to produce the ester.
    Type: Grant
    Filed: September 15, 1987
    Date of Patent: May 17, 1988
    Assignee: Eastman Kodak Company
    Inventors: Winston J. Jackson, Jr., Thomas H. Wicker, Jr.
  • Patent number: 4613678
    Abstract: Esterification of aromatic dicarboxylic acids with cyclic alkylene carbonates in the presence of organic compounds containing at least one six-membered aromatic nitrogen-containing heterocyclic moiety.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: September 23, 1986
    Assignee: The Dow Chemical Company
    Inventor: Daniel J. Swart
  • Patent number: 4578502
    Abstract: Solid scrap polyethylene terephthalate (PET) resin may be reprocessed by depolymerizing said scrap in the presence of water or methanol, recovering the monomers resulting from the depolymerization reaction and repolymerizing the monomers to form polymeric polyethylene phthalate.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: March 25, 1986
    Inventor: Warner J. G. Cudmore
  • Patent number: 4507475
    Abstract: A process for purifying crude polyether polyols which are prepared by anionic polymerization of alkylene oxides in the presence of basic catalysts. The polyols are mixed with water and ortho-phosphoric acid in certain quantity ratios, an adsorption agent is incorporated in the reaction mixture, the mixture is filtered and the water is removed from the polyether polyol by distillation.
    Type: Grant
    Filed: July 22, 1983
    Date of Patent: March 26, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Straehle, Raymond Denni, Matthias Marx
  • Patent number: 4506091
    Abstract: A process for preparing esters which comprises reacting a polycarboxylic acid with an excess of alcohol and in the presence of an organotitanate catalyst, treating the crude mixture with a suitable chelate compound, removing the unreacted alcohol and hydrolyzing the treated titanium catalyst residues with steam, and recovering the purified ester by filtration.
    Type: Grant
    Filed: September 1, 1983
    Date of Patent: March 19, 1985
    Inventor: Donald L. Deardorff
  • Patent number: 4444692
    Abstract: Hydroxyl terminated reactive liquid polymers are prepared by reacting ethylene oxide, in presence of an amine catalyst, with a carboxyl terminated reactive liquid polymer serum which contains, in addition to the carboxyl terminated liquid polymer, a solvent, an initiator, other reaction products formed during the reaction, and any unreacted reactants; adding a strong acid to form water-soluble amine salts; water-washing; coagulating; separating; drying; and recovering a shelf stable product.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: April 24, 1984
    Assignee: The B. F. Goodrich Company
    Inventor: Yoshihisa Okamoto
  • Patent number: 4435592
    Abstract: Polyether-ester polyols are prepared by reacting a crude polyether polyol, tetrahydrophthalic anhydride and an alkylene oxide. These polyols may be used in preparing polyrethane products.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: March 6, 1984
    Assignee: BASF Wyandotte Corporation
    Inventor: Curtis J. Reichel
  • Patent number: 4394286
    Abstract: Disclosed is partially hydrolyzed, DMT process residue. Also disclosed is the reaction product of propylene oxide and the partially hydrolyzed, DMT process residue. The reaction product is useful as a polyol reactant in the preparation of urethane foams.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: July 19, 1983
    Assignee: Hercofina
    Inventor: William H. Millick, III
  • Patent number: 4390398
    Abstract: Volatile reactants are heated under reflux in a reactor and form volatile reaction by-products which are continuously removed in a vapor effluent from a reflux column and partial condenser. The effluent, which entrains some of the reactants, is condensed in a first total condenser and is fed to a distillation apparatus for separation of the volatile reactants and by-products and return of the separated reactants to the reactor. Before the condensate reaches the distillation apparatus, it is temporarily stored in a receiver from which it is controllably fed to a pre-heater where it is evaporated and then fed as a vapor to the distillation column of the distillation apparatus for separation. The distillation column includes at one end a reboiler which retains the reactants. The other end of the distillation column is coupled to a second total condenser in which the volatile by-products are condensed and withdrawn through a cooler for disposal.
    Type: Grant
    Filed: May 12, 1980
    Date of Patent: June 28, 1983
    Assignee: Fiberglas Canada Limited
    Inventors: Robert J. Coker, Gary W. Bate, Henk J. Deuzeman
  • Patent number: 4329489
    Abstract: Preparation of a fluorocarbon compound used to make a soil-resistant yarn is improved by removing most of the impurities from the fluoro-carbon compound mass with heat and vacuum after the final washing step and then adding an emulsifier to the fluorocarbon compound mass so that the mass can be handled as a liquid concentrate rather than a tacky solid.
    Type: Grant
    Filed: May 19, 1980
    Date of Patent: May 11, 1982
    Assignee: Allied Chemical Corporation
    Inventors: Peter R. Saunders, Raymond J. Biron
  • Patent number: 4304925
    Abstract: In a process for purifying an ester with little contamination by catalytic metal components in a high yield which comprises treating an esterification reaction mixture with a basic substance, said esterification reaction mixture being obtained by reacting an organic carboxylic acid or its anhydride with an alcohol in the presence of an organometallic compound as an esterification catalyst, and purifying the product in a manner known per se; the improvement wherein prior to said treatment with the basic substance, water is added to the esterification reaction mixture and the mixture is heated.
    Type: Grant
    Filed: March 26, 1980
    Date of Patent: December 8, 1981
    Assignee: Sekisui Kagaku Kogyo Kabushiki Kaisha
    Inventors: Tsutomu Watanabe, Tadayoshi Kawakami
  • Patent number: 4255591
    Abstract: There is provided an improved continuous homogeneous catalytic carbonylation process wherein a mixed gas stream is removed from the carbonylation reactor, condensable liquids separated from said gas stream and said gas stream vented, the improvement comprising contacting said gas stream with a plurality of hollow fiber membranes selectively permeable to hydrogen under conditions substantially non-degrading of the membranes to generate a non-permeated gas stream of higher carbon monoxide content and recycling said non-permeated gas stream to the carbonylation process reactor. There is also provided for the recovery and recycle to the process of carbonylation products such as acetic or propionic acids by adsorption and removal from a solid adsorbent or absorption in a liquid absorbent.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: March 10, 1981
    Assignee: Monsanto Company
    Inventors: Earle C. Makin, Jerry L. Price, Yu W. Wei
  • Patent number: 4216337
    Abstract: A process for preparing esters which comprises reacting a polycarboxylic acid with an alcohol, removing the unreacted alcohol from the resultant esterification reaction mixture, heating the crude ester at a temperature of 160.degree. to 340.degree. C., contacting the heat-treated crude ester with an adsorbent, and recovering the ester of high purity. The ester obtained has superior electrical insulation, transparency and thermal stability.
    Type: Grant
    Filed: July 10, 1978
    Date of Patent: August 5, 1980
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Makoto Baba, Teruyuki Ninomiya, Chieko Ono
  • Patent number: 4118582
    Abstract: Spent ethylene glycol recovered from polyester manufacture contains dissolved antimony catalyst residues and other impurities. Prior to distillation of the spent glycol to recover purified ethylene glycol, the antimony compounds are removed by adjusting the pH of the spent glycol to about 2 to 7, preferably 5 to 7, preferably by adding an organic acid (e.g., acetic acid) adding an alkali metal borohydride (e.g., sodium borohydride) in the absence of oxygen and with intimate mixing to form a metallic antimony precipitate, and recovering the precipitate. The process is further improved by adding a catalytic amount of a strong inorganic base, e.g., sodium hydroxide, prior to the pH adjustment step, to convert any terephthalyl values to dihydroxyethyl terephthalate which can be recovered.
    Type: Grant
    Filed: January 17, 1977
    Date of Patent: October 3, 1978
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Charles Carey Walker
  • Patent number: 4105701
    Abstract: A liquid contaminated with a carbonyl compound, especially an aldehyde, is purified by being contacted with a bed of solid polyvinyl alcohol particles or fibers. The carbonyl compound is adsorbed or chemisorbed onto the solid polyvinyl alcohol surface with resulting reaction in the carbonyl content of the liquid.
    Type: Grant
    Filed: April 28, 1975
    Date of Patent: August 8, 1978
    Assignee: Celanese Corporation
    Inventor: Donald R. Larkin
  • Patent number: 4102922
    Abstract: A method is provided for the removal of contaminating alkanes from the vaporized carbonylation products of a process wherein carboxylic acids are produced by the reaction in the liquid phase of an alcohol or an ester, halide or ether derivative of said alcohol with carbon monoxide in the presence of a catalyst system containing a rhodium or iridium component and an iodine or bromine component. The method involves distillation of the alkane-containing vaporized carbonylation products, phase separation of the overhead from said distillation, further distillation of a slipstream of the resulting heavy phase using carbon monoxide as stripping gas and removal of the alkanes as the bottoms stream from the latter distillation.
    Type: Grant
    Filed: October 12, 1976
    Date of Patent: July 25, 1978
    Assignee: Monsanto Company
    Inventor: Jerry L. Price
  • Patent number: 4085083
    Abstract: Polyesters derived from the reaction of a dibasic acid, a polyethylene glycol and an aliphatic alcohol are used as plasticizers for vinyl acetate polymers.
    Type: Grant
    Filed: August 7, 1975
    Date of Patent: April 18, 1978
    Assignee: Ciba-Geigy AG
    Inventors: Frank Lamb, Malcolm Combey, Hugh Melvin Cooper
  • Patent number: 4077945
    Abstract: A batch process for esterifying ethylene glycol and terephthalic acid at elevated temperature and pressure in which a part of the ethylene glycol required for the complete esterification reaction is placed in an autoclave and heated under pressure, and the remainder of the glycol is added to said heated glycol in the form of a paste with terephthalic acid. Preferably the glycol initially present in the autoclave amounts to 0.3 to 0.8 moles per mole of terephthalic acid while the glycol added as a paste amounts to 1.4 to 0.9 moles per mole of terephthalic acid. The glycol initially in the autoclave may be glycol reclaimed from the mixture volatilized during the reaction and may contain up to 20% water, preferably 2-6% water.
    Type: Grant
    Filed: April 18, 1977
    Date of Patent: March 7, 1978
    Assignee: Zimmer Aktiengesellschaft
    Inventors: Helmut Heinze, Eberhard Hackel