Of Ester Of Polyoxy Alcohols Patents (Class 560/79)
-
Patent number: 12240809Abstract: The invention relates to a solid composition comprising at least 90.0 wt. % bis(2-hydroxyethyl) terephthalate (BHET), as based on dry weight and having a pore volume in the range of 0.20 to 1.0 cm3/g. The porosity is above 25% or even above 35%. The solid composition is made by crystallisation, followed by granulation and fluid bed drying.Type: GrantFiled: August 20, 2020Date of Patent: March 4, 2025Assignee: Ioniqa Technologies B.V.Inventors: Andre Banier De Haan, Joost Robert Wolters, Michael Josef De Groot, Jannigje Maria Jacomina Gravendeel
-
Patent number: 11107787Abstract: A member for semiconductor device includes a metal portion configured to be bonded to another member by solder, and a treated coating covering a surface of the metal portion, the treated coating including a treatment agent. The treated coating vaporizes at a temperature lower than or equal to a solidus temperature of the solder.Type: GrantFiled: November 8, 2018Date of Patent: August 31, 2021Assignee: FUJI ELECTRIC CO., LTD.Inventors: Shinji Sano, Yoshihiro Kodaira, Masayuki Soutome, Kazunaga Onishi
-
Patent number: 10927231Abstract: Particles of a transition metal are used as a catalyst for depolymerisation of condensation polymers in alcohol. In the method of catalysed depolymerisation of a condensation polymer in a solid form into monomers and/or oligomers, transition metal particles; are mixed with the condensation polymer in alcohol to obtain a reaction mixture. This reaction mixture is processed to disperse the condensation polymer into the alcohol and decompose it, wherein the transition metal particles act as a catalyst and the alcohol is a reagent. The catalyst is particularly supplied as a catalyst composition of transition metal particles in an alcoholic liquid. The transition metal particles are typically non-porous and may have an oxide surface.Type: GrantFiled: January 30, 2018Date of Patent: February 23, 2021Inventors: Sonja Irene-Marie Reginalde Castillo, Vincent Gertrudis Antonius Philippi
-
Patent number: 10767027Abstract: The present invention relates, in part, to methods for depolymerizing a polymer, in which the method includes use of a magnetic catalyst. The magnetic catalyst can include, e.g., a ore-shell particle, such as a particle having a magnetic core and a shell including a metal-organic framework.Type: GrantFiled: October 17, 2019Date of Patent: September 8, 2020Assignees: National Technology & Engineering Solutions of Sandia, LLC, The Regents of the University of CaliforniaInventors: Jian Sun, Blake A. Simmons, Seema Singh
-
Patent number: 10508186Abstract: A process for chemically recycling polyethylene terephthalate (PET) which utilizes a microwave absorber to optimize glycolytic depolymerization of PET via microwave irradiation. The method of chemically degrading PET to its reactive intermediate, bis(2-hydroxyethyl) terephthalate (BHET), is carried out by: (a) combining PET with ethylene glycol and a catalytic system comprising a catalyst and a microwave absorber to produce a heterogeneous reaction mixture; and then (b) heating by microwave irradiating the reaction mixture to a temperature sufficient to produce a reaction product comprising BHET. The BHET monomer then can be purified and re-polymerized to form new, virgin PET.Type: GrantFiled: November 18, 2016Date of Patent: December 17, 2019Assignee: The University of North Carolina at Chapel HillInventor: Matthew Parrott
-
Patent number: 8299281Abstract: 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: GrantFiled: March 16, 2010Date of Patent: October 30, 2012Assignee: ExxonMobil Research and Engineering CompanyInventors: Jihad Mohammed Dakka, Edmund J Mozeleski, Lisa Saunders Baugh
-
Patent number: 7511081Abstract: 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: GrantFiled: March 24, 2005Date of Patent: March 31, 2009Inventors: Do-Gyun Kim, Hyo-Sung Kim
-
Patent number: 7381354Abstract: 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: GrantFiled: May 21, 2007Date of Patent: June 3, 2008Assignee: Albemarle CorporationInventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
-
Patent number: 7329772Abstract: 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: GrantFiled: April 29, 2004Date of Patent: February 12, 2008Assignee: Crompton CorporationInventor: John R. Baranski
-
Patent number: 7323289Abstract: 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: GrantFiled: October 6, 2003Date of Patent: January 29, 2008Assignee: Brewer Science Inc.Inventors: Charles J. Neef, Mandar Bhave, Michelle Fowler, Michelle Windsor
-
Patent number: 7258823Abstract: 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: GrantFiled: May 20, 2004Date of Patent: August 21, 2007Assignee: Albemarle CorporationInventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
-
Patent number: 7045564Abstract: 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: GrantFiled: August 29, 2003Date of Patent: May 16, 2006Assignee: Albemarle CorporationInventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
-
Patent number: 7022259Abstract: 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: GrantFiled: September 30, 2003Date of Patent: April 4, 2006Assignee: Industrial Technology Research InstituteInventors: Dao-Hung Lee, Ding-Jen Chen, Kung-Lung Cheng
-
Patent number: 6855844Abstract: 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: GrantFiled: October 25, 2000Date of Patent: February 15, 2005Assignee: Stepan CompanyInventors: Eric J. Geiger, Douglas K. Hillshaffer
-
Patent number: 6740686Abstract: 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 oType: GrantFiled: November 27, 2000Date of Patent: May 25, 2004Assignee: Crompton CorporationInventors: Denis Ghesquiere, Remy Dumont
-
Patent number: 6667416Abstract: 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: GrantFiled: July 26, 2001Date of Patent: December 23, 2003Assignee: Mitsui Takeda Chemicals, Inc.Inventors: Kouichi Murayama, Katsumi Inaoka, Takashi Kumaki
-
Patent number: 6642407Abstract: 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: GrantFiled: April 26, 2002Date of Patent: November 4, 2003Assignee: Exxon Mobil Chemical Patents Inc.Inventors: Krishna Kulai Rao, Russell D. Sellen, Xiaobing Feng, James Spanswick, William F. Huber, Jr.
-
Patent number: 6582626Abstract: 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: GrantFiled: November 8, 2001Date of Patent: June 24, 2003Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Hiroshi Hasebe, Sadao Takehara, Kiyofumi Takeuchi
-
Patent number: 6569352Abstract: 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: GrantFiled: October 25, 1999Date of Patent: May 27, 2003Assignee: Stepan CompanyInventors: Douglas K. Hillshafer, George Magnus
-
Patent number: 6407201Abstract: 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: GrantFiled: August 21, 2000Date of Patent: June 18, 2002Assignee: Bayer CorporationInventors: Ronald P. Taylor, Jeffrey A. Dodge, Hartmut Nefzger
-
Publication number: 20020035166Abstract: 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: ApplicationFiled: July 26, 2001Publication date: March 21, 2002Inventors: Kouichi Murayama, Katsumi Inaoka, Takashi Kumaki
-
Patent number: 6329535Abstract: 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: GrantFiled: October 20, 2000Date of Patent: December 11, 2001Assignee: Degussa Dental GmbH & Co. KGInventors: Horst Weigel, Steffen Krill, Hans Joachim Hasselbach, Klaus Huthmacher
-
Patent number: 6103924Abstract: 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: GrantFiled: April 21, 1999Date of Patent: August 15, 2000Assignee: Degussa-Huls AGInventors: Nongyuan Shi, Mario Scholz, Steffen Hasenzahl, Horst Weigel, Bernd Drapal, Ralph McIntosh, Hans J. Hasselbach, Klaus Huthmacher
-
Patent number: 6100374Abstract: 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: GrantFiled: March 9, 1999Date of Patent: August 8, 2000Assignee: Mitsui Chemicals Inc.Inventors: Hiroshi Iwasaki, Satoshi Inoki, Hiromi Ueki
-
Patent number: 5908956Abstract: 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: GrantFiled: December 17, 1997Date of Patent: June 1, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Ikuo Takahashi, Masahiro Chikamori
-
Patent number: 5530128Abstract: 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: GrantFiled: February 2, 1994Date of Patent: June 25, 1996Assignee: Celltech Therapeutics LimitedInventors: John R. Porter, John R. Morphy, Thomas A. Millican, Nigel R. A. Beeley
-
Patent number: 5414107Abstract: 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: GrantFiled: July 20, 1994Date of Patent: May 9, 1995Assignee: Hoechst Celanese CorporationInventor: Brad L. Smith
-
Patent number: 5413681Abstract: 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: GrantFiled: November 15, 1993Date of Patent: May 9, 1995Assignee: Eastman Chemical CompanyInventors: Gerald C. Tustin, Thomas M. Pell, Jr., David A. Jenkins, Mary T. Jernigan
-
Patent number: 5332859Abstract: Described is a batchwise process for producing tetrabromophthalic diester flame retardants having consistent product characteristics.Type: GrantFiled: November 3, 1992Date of Patent: July 26, 1994Assignee: Great Lakes Chemical Europe, Ltd.Inventor: Brian Tarbit
-
Patent number: 5328982Abstract: 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: GrantFiled: November 2, 1992Date of Patent: July 12, 1994Assignee: Eastman Chemical CompanyInventors: George W. Tindall, Randall L. Perry, Art T. Spaugh, Jr.
-
Patent number: 5319128Abstract: 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: GrantFiled: March 30, 1992Date of Patent: June 7, 1994Assignee: Synergistics Industries, Ltd.Inventors: Louis Dupont, Ved P. Gupta
-
Patent number: 5101064Abstract: 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: GrantFiled: March 15, 1990Date of Patent: March 31, 1992Assignee: Synergistics Industries LimitedInventors: Louis Dupont, Ved P. Gupta
-
Patent number: 5045122Abstract: 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: GrantFiled: December 14, 1989Date of Patent: September 3, 1991Assignee: Eastman Kodak CompanyInventors: George W. Tindall, Randall L. Perry
-
Patent number: 4929749Abstract: 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: GrantFiled: March 15, 1989Date of Patent: May 29, 1990Assignee: Synergistics Industries, LimitedInventors: Ved P. Gupta, Louis A. DuPont
-
Patent number: 4876378Abstract: 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: GrantFiled: May 23, 1988Date of Patent: October 24, 1989Assignee: Eastman Kodak CompanyInventor: Dale E. Van Sickle
-
Patent number: 4868324Abstract: 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: GrantFiled: May 24, 1988Date of Patent: September 19, 1989Assignee: Celanese Engineering Resins, Inc.Inventors: A. Lee Stautzenberger, Ellen A. Langford, Edward E. Quick
-
Patent number: 4754053Abstract: 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: GrantFiled: May 12, 1987Date of Patent: June 28, 1988Assignee: Great Lakes Chemical CorporationInventors: Rastko I. Mamuzic, Bhabatosh Bhattacharya
-
Patent number: 4745211Abstract: 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: GrantFiled: September 15, 1987Date of Patent: May 17, 1988Assignee: Eastman Kodak CompanyInventors: Winston J. Jackson, Jr., Thomas H. Wicker, Jr.
-
Patent number: 4613678Abstract: 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: GrantFiled: June 30, 1980Date of Patent: September 23, 1986Assignee: The Dow Chemical CompanyInventor: Daniel J. Swart
-
Patent number: 4578502Abstract: 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: GrantFiled: January 22, 1985Date of Patent: March 25, 1986Inventor: Warner J. G. Cudmore
-
Patent number: 4507475Abstract: 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: GrantFiled: July 22, 1983Date of Patent: March 26, 1985Assignee: BASF AktiengesellschaftInventors: Wolfgang Straehle, Raymond Denni, Matthias Marx
-
Patent number: 4506091Abstract: 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: GrantFiled: September 1, 1983Date of Patent: March 19, 1985Inventor: Donald L. Deardorff
-
Patent number: 4444692Abstract: 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: GrantFiled: May 18, 1981Date of Patent: April 24, 1984Assignee: The B. F. Goodrich CompanyInventor: Yoshihisa Okamoto
-
Patent number: 4435592Abstract: 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: GrantFiled: September 29, 1982Date of Patent: March 6, 1984Assignee: BASF Wyandotte CorporationInventor: Curtis J. Reichel
-
Patent number: 4394286Abstract: 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: GrantFiled: May 20, 1981Date of Patent: July 19, 1983Assignee: HercofinaInventor: William H. Millick, III
-
Patent number: 4390398Abstract: 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: GrantFiled: May 12, 1980Date of Patent: June 28, 1983Assignee: Fiberglas Canada LimitedInventors: Robert J. Coker, Gary W. Bate, Henk J. Deuzeman
-
Patent number: 4329489Abstract: 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: GrantFiled: May 19, 1980Date of Patent: May 11, 1982Assignee: Allied Chemical CorporationInventors: Peter R. Saunders, Raymond J. Biron
-
Patent number: 4304925Abstract: 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: GrantFiled: March 26, 1980Date of Patent: December 8, 1981Assignee: Sekisui Kagaku Kogyo Kabushiki KaishaInventors: Tsutomu Watanabe, Tadayoshi Kawakami
-
Patent number: 4255591Abstract: 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: GrantFiled: November 20, 1978Date of Patent: March 10, 1981Assignee: Monsanto CompanyInventors: Earle C. Makin, Jerry L. Price, Yu W. Wei
-
Patent number: 4216337Abstract: 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: GrantFiled: July 10, 1978Date of Patent: August 5, 1980Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Makoto Baba, Teruyuki Ninomiya, Chieko Ono