Unsaturation In Acid Moiety Patents (Class 560/205)
  • Patent number: 11161799
    Abstract: The present invention relates to the production of light (meth)acrylic esters by direct esterification of acrylic acid by methanol or ethanol. The invention more particularly relates to a process for the recovery/purification of C1-C2 alkyl acrylate comprising the azeotropic distillation of the crude reaction mixture using a distillation column comprising a sidestream drawing off of a fraction rich in alkyl alkoxypropionate byproduct, the boiling point of which is close to that of acrylic acid, and therefore problematic in the purification process.
    Type: Grant
    Filed: June 26, 2019
    Date of Patent: November 2, 2021
    Assignee: Arkema France
    Inventor: Pierre-Emmanuel Conoir
  • Patent number: 10941103
    Abstract: A process for continuously preparing a butyl acrylate H2C?CH—C(?O)OR, with R=n-butyl or isobutyl, wherein aqueous 3-hydroxypropionic acid is converted under dehydrating and esterifying conditions in the presence of the corresponding butanol R—OH in a reactor with a rectification column and butyl acrylate formed, unconverted butanol and water used and formed are distilled off overhead as a ternary azeotrope, after separation into a liquid aqueous phase and liquid organic phase each of the aqueous and organic phases is at least partly discharged, and the organic phase comprising the butyl acrylate and the butanol is subjected to distillative separation.
    Type: Grant
    Filed: August 13, 2018
    Date of Patent: March 9, 2021
    Assignee: BASF SE
    Inventors: Ortmund Lang, Tim Blaschke, Christian Raith, Michael Schafranka, Claus Hechler
  • Patent number: 10550052
    Abstract: Provided are an industrially advantageous method for separating and purifying isobutylene, the method enabling high-purity isobutylene to be efficiently obtained by a simple process, and a method for producing isobutylene. A method for separating and purifying isobutylene from a reaction gas containing the isobutylene and unreacted isobutanol, comprising: a step (1) of contacting the reaction gas containing the isobutylene and unreacted isobutanol with a first solvent to obtain a first gas containing the isobutylene and a recovered solution containing the unreacted isobutanol; a step (2) of contacting the first gas with a specific second solvent to allow the second solvent to absorb the isobutylene contained in the first gas to obtain an absorption solution containing the isobutylene; and a step (3) of distilling the absorption solution to obtain separated and purified isobutylene. A method for producing isobutylene using the separation and purification method.
    Type: Grant
    Filed: February 13, 2019
    Date of Patent: February 4, 2020
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Shimpei Kato, Daisuke Tomikawa, Manabu Hoshino
  • Patent number: 10421705
    Abstract: Provided is a production method whereby corresponding carboxylic acid esters can be obtained from a variety of carboxylic acids at a high yield, even under conditions using a simple reaction operation and little catalyst and even if the amount of substrate used is theoretical. A production method for carboxylic acid ester, whereby a prescribed diester dicarbonate, carboxylic acid, and alcohol are reacted in the presence of at least one type of magnesium compound and at least one type of alkali metal compound.
    Type: Grant
    Filed: December 11, 2015
    Date of Patent: September 24, 2019
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Akihiro Goto, Yoshihiro Kamon, Hiroyuki Mori
  • Patent number: 10301252
    Abstract: A process for continuously preparing the tert-butyl ester of an ethylenically unsaturated carboxylic acid, by a) reacting an ethylenically unsaturated carboxylic acid with isobutene in the presence of an acidic catalyst to give an esterification mixture; b) removing the acidic catalyst; c) removing low-boiling components; and d) supplying a tert-butyl ester-comprising liquid to a distillation apparatus and subjecting it to purifying distillation in the distillation apparatus, where d1) in the distillation apparatus the tert-butyl ester-comprising liquid is separated into a tert-butyl ester-comprising gaseous top product and a carboxylic acid-comprising liquid bottom product; d2) the tert-butyl ester-comprising gaseous top product is at least partly condensed and the condensate is recycled partly as reflux to the distillation apparatus; d3) the carboxylic acid-comprising liquid bottom product is recycled at least partly to step a); d4) carboxylic acid-comprising liquid bottom product is drawn off and passed to
    Type: Grant
    Filed: November 28, 2016
    Date of Patent: May 28, 2019
    Assignee: BASF SE
    Inventors: Catharina Horstmann, Claus Hechler, Gregor Grackiewicz, Bernd Schall
  • Patent number: 9975842
    Abstract: The present invention relates to a method for producing a C4-C10 alkyl (meth)acrylate, by direct esterification of (meth)acrylic acid by the corresponding alcohol, the reaction water being removed in the form of an azeotrope with the esterification alcohol from a distillation column mounted over the esterification reactor comprising a cationic resin as a catalyst. Said method is characterized in that the molar ratio of alcohol to acid at the inlet of the reactor is between 1.4 and 3, and in that the crude reaction mixture circulates in a recirculation loop joining the reactor and the water removal column, at a recirculation rate of between 6 and 25, expressed by the mass ratio between the flow fed into the loop and the flow sent to a purification treatment.
    Type: Grant
    Filed: June 22, 2015
    Date of Patent: May 22, 2018
    Assignee: ARKEMA FRANCE
    Inventors: Anne Moreliere, Gilles Frimour, Jean-Michel Paul, Stephane Denis
  • Patent number: 9951163
    Abstract: The present invention provides a resist or a compound for use as a resist, which is highly sensitive and well-balanced without losing the fundamental physical properties required as a chemically amplified resist (e.g., resolution, line edge roughness (LER)). The present invention is directed to a (meth)acrylate compound represented by general formula (1) and a process for preparation thereof, as well as a (meth)acrylic copolymer obtainable by polymerization of the (meth)acrylate compound of general formula (1) and a photosensitive resin composition thereof: (wherein R1 represents a hydrogen atom or a methyl group, R2 represents a linear or branched alkyl group containing 2 to 4 carbon atoms, and each R3 may be the same or different and represents a group represented by the following formula (2) or (3), etc.) (provided that formulae (2) and (3) are as defined in the specification of the present application).
    Type: Grant
    Filed: January 30, 2015
    Date of Patent: April 24, 2018
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hiroyasu Tanaka, Shoichi Hayakawa, Hiroyuki Tanagi, Kikuo Furukawa, Hiroshi Horikoshi
  • Patent number: 9701610
    Abstract: Hydroxycarboxylic acids, e.g., 3-hydroxypropionic acid, and/or their ammonium salts are dehydrated to their corresponding unsaturated carboxylic acids, e.g., acrylic acid, by a process that uses a catalyst comprising ammonium bisulfate. The use of ammonium bisulfate reduces or eliminates the problems associated with processes that use sulfuric acid as a dehydrating catalyst, e.g, excess sulfuric acid consumption and/or recovery.
    Type: Grant
    Filed: October 14, 2014
    Date of Patent: July 11, 2017
    Assignees: Dow Global Technologies LLC, Rohm and Haas Company
    Inventors: Leonard E. Bogan, Jr., Mark A. Silvano, Raymond P. Roach, Sarah M. Hoyt, Robert Tengler, David C. Decoster, Sanjib Biswas, Muhunthan Sathiosatham, Sarah L. Hruby, Andrew M. Lemonds
  • Patent number: 9688622
    Abstract: Provided is a 1-(2-acyloxyethyl)cyclopropyl sulfonate compound of General Formula (2): wherein R1 is a monovalent hydrocarbon group having 1 to 10 carbon atoms and optionally containing one or more unsaturated bonds and Z is a monovalent hydrocarbon group having 1 to 10 carbon atoms and optionally containing one or more unsaturated bonds.
    Type: Grant
    Filed: February 17, 2017
    Date of Patent: June 27, 2017
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Naoki Ishibashi, Yusuke Nagae
  • Patent number: 9604902
    Abstract: A method of making 2-octyl acrylate comprising reacting 2-octanol with acrylic acid in the presence of an acid catalyst and added water is described. The 2-octanol may be derived from renewable resources, such as castor oil. The method is efficient and provides selectivity for 2-octyl acrylate.
    Type: Grant
    Filed: March 4, 2014
    Date of Patent: March 28, 2017
    Assignee: 3M Innovative Properties Company
    Inventors: Joshua L. Colby, Tabitha A. Clem, Terence D. Spawn, Aaron E. Hutt, Wade T. Teply
  • Patent number: 9546190
    Abstract: A simple, commercially viable process for the preparation of phosphonic acid monomers containing essentially no diester or inorganic phosphorous acid compounds is disclosed.
    Type: Grant
    Filed: November 26, 2013
    Date of Patent: January 17, 2017
    Assignee: Rohm and Haas Company
    Inventors: Muhunthan Sathiosatham, Douglass Sevon
  • Patent number: 9464024
    Abstract: Disclosed is a method of making methacrylic acid, or a carboxylic derivative thereof, from itaconic acid, isomers, or precursors thereof. A starting material comprising an acid selected from the group consisting of itaconic acid, citraconic acid, mesaconic acid, citric acid, aconitic acid, isocitric acid and mixtures thereof, is subjected to contact with 0.1 eq. to 3.0 eq. of a base, at a temperature of 150° C. to 350° C., under the influence of a transition metal-containing heterogeneous catalyst. A better yield at lower temperatures is achieved.
    Type: Grant
    Filed: August 26, 2014
    Date of Patent: October 11, 2016
    Assignee: Stichting Dienst Landbouwkundig Onderzoek
    Inventors: Jerome Emile Lucien Le Notre, Elinor Lindsey Scott, Roeland Leo Croes, Jacobus Van Haveren
  • Patent number: 9403750
    Abstract: The invention relates to a process for continuously producing 2-octyl acrylate by reacting acrylic acid and 2-octanol in the presence of a sulfonic acid esterification catalyst and at least one polymerization inhibitor. The water formed by the esterification reaction is entrained by distillation in a column surmounting the reactor in the form of a heteroazeotropic mixture with the 2-octanol which is then subjected, after condensation, to separation in a decanter so as to give an upper organic phase and a lower aqueous phase. The reaction mixture containing the reaction product and residual by-products are purified by separation means in order to obtain: (1) pure 2-octyl acrylate and (2) unreacted 2-octanol and acrylic acid compounds that will be recycled along with the catalyst.
    Type: Grant
    Filed: October 30, 2012
    Date of Patent: August 2, 2016
    Assignee: Arkema France
    Inventors: Alain Riondel, Coralie Graire, Andre Levray, Reinhard Linemann
  • Patent number: 9206109
    Abstract: In a method of stabilizing acrylic compounds, a liquid phase containing at least one acrylic compound is mixed with at least one metal and at least one ligand. The acrylic compound can be acrylic acid, methacrylic acid, and their respective esters. The metal can be copper, manganese, and cerium. The ligand can be a quinoline compound of formula (I), an N-oxide of a compound of formula (I), 2,2?-bis(2,3-dihydro-3-oxoindolylidene), or an aliphatic y-dentate ligand with y being 2-6 and comprising at least two nitrogen atoms joined by aliphatic or aromatic C1-C4 bridges comprising y-2 further coordinating nitrogen atoms or heteroatoms: where X is OH, NH2, O—(C1-C4)-alkyl, O—C(O)—(C1-C4)-alkyl, or O—C(O)-phenyl; R1 is H, or (C1-C4)-alkyl; R2 is H, (C1-C4)-alkyl, Cl, Br, or SO3H; and R3 is H, Cl or Br.
    Type: Grant
    Filed: December 12, 2013
    Date of Patent: December 8, 2015
    Assignee: BASF SE
    Inventors: Tobias Johannes Korn, Peter Zurowski, Thorsten Friese, Sylke Haremza, Ulrich Jaeger, Steffen Rissel, Volker Schliephake
  • Patent number: 9035086
    Abstract: The present invention relates to a covalently organo-modified LDH (LDH/APTES) was found to be an efficient and reusable heterogeneous catalyst for C—C bond forming reactions (i.e. Aldol condensation, Knoevenagel condensation, Henry reaction, Michael addition). More particularly, this catalyst shows consistent activity for several cycles in C—C bond forming reaction. These catalysts were successfully characterized by XRD, FT-IR, 29Si CP MAS NMR.
    Type: Grant
    Filed: February 14, 2012
    Date of Patent: May 19, 2015
    Assignee: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
    Inventors: Kulamani Parida, Sudarshan Singha, Mitarani Sahoo
  • Publication number: 20150119598
    Abstract: Provided is a simple and efficient method for producing (E)-2-isopropyl-5-methyl-2,4-hexadienyl acetate. More specifically, provided is a method for producing (E)-2-isopropyl-5-methyl-2,4-hexadienyl acetate including the steps of: isomerizing 2-isopropenyl-5-methyl-4-hexenoic acid (1) into (E)-2-isopropyl-5-methyl-2,4-hexadienoic acid (2), reducing thus formed (E)-2-isopropyl-5-methyl-2,4-hexadienoic acid (2) into (E)-2-isopropyl-5-methyl-2,4-hexadienol (3), and acetylating thus formed (E)-2-isopropyl-5-methyl-2,4-hexadienol (3) into (E)-2-isopropyl-5-methyl-2,4-hexadienyl acetate (4), wherein Ac represents an acetyl group.
    Type: Application
    Filed: October 29, 2014
    Publication date: April 30, 2015
    Inventors: Takeshi KINSHO, Naoki ISHIBASHI, Yoshiyuki YUMOTO
  • Patent number: 9017931
    Abstract: A negative pattern is formed by coating a resist composition comprising a polymer comprising recurring units having a tertiary ester type acid labile group having a plurality of methyl or ethyl groups on alicycle and an acid generator onto a substrate, prebaking, exposing to high-energy radiation, baking, and developing in an organic solvent developer so that the unexposed region of resist film is dissolved away and the exposed region of resist film is not dissolved. The resist composition exhibits a high dissolution contrast during organic solvent development and forms a fine hole or trench pattern of dimensional uniformity.
    Type: Grant
    Filed: August 16, 2013
    Date of Patent: April 28, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Jun Hatakeyama, Masayoshi Sagehashi, Teppei Adachi
  • Patent number: 8987501
    Abstract: A radioisotope labeled reagent includes a compound having the general formula (I), L-(aCbH2)naCbH3??(I) where a in each occurrence independently is a carbon mass number between 11 and 14 inclusive, b in each occurrence independently is a hydrogen mass number between 1 and 3 inclusive, such that a in each occurrence is not 12 simultaneously with b in each occurrence being 1; L is a leaving group R1SO2—O—, R1—S—, 12C1H3(12C3H2)n—S—R1C(O)O—, NC—, (R1)3P—, XMg- and Li—, where n is an integer between 0 and 3 inclusive, where X is chloro, bromo or iodine, where R1 is H, aryl, a substituent containing aryl, C1-C20 alkyl, a substituent containing C1-C20 alkyl, C2-C20 alkenyl, a substitute containing C2-C20 alkenyl, C2-C20 alkynyl, and a substitute containing C2-C20 alkynyl with the proviso that when n is 0, a is 13 and b is 2 and R1 in R1—S is not aryl.
    Type: Grant
    Filed: October 4, 2012
    Date of Patent: March 24, 2015
    Assignee: PerkinElmer Health Sciences, Inc.
    Inventor: Jerry Scot Pounds
  • Publication number: 20150080606
    Abstract: Described herein are methods for preparing methacrylic acid from biobased starting materials.
    Type: Application
    Filed: September 16, 2014
    Publication date: March 19, 2015
    Inventor: JOSHUA LENSBOUER
  • Publication number: 20150065745
    Abstract: A reactor and process for the production of bio-diesel. The reactor includes one or more coiled reaction lines. The lines are positioned within a tank containing a heat transfer media such as molten salt, maintained at about 750° F. A pump circulates the media within the tank. An emulsion of alcohol; refined feed stock, including glycerides and/or fatty acids; and preferably water is pumped through the reaction lines at temperatures and pressures sufficient to maintain the alcohol in a super-critical state. The curvature of the coils, pump pulsing, and the flow rate of the emulsion keep the emulsion in a turbulent state while in the reactor, ensuring thorough mixing of the alcohol and feed stock. The alcohol reacts with the glycerides and fatty acids to form bio-diesel. The reaction is fast, efficient with regard to energy input and waste generation, and requires minimal alcohol.
    Type: Application
    Filed: November 22, 2013
    Publication date: March 5, 2015
    Applicant: LOUISIANA ECO GREEN, L.L.C.
    Inventors: Kemper J. McSpadden, Gerard M. Thomassie
  • Publication number: 20150057455
    Abstract: Methods and systems for producing high purity 3-hydroxypropionic acid (3-HP) from an aqueous medium, such as a fermentation broth, are described. Aqueous 3-HP solution can be purified by flash evaporation wherein the 3-HP is vaporized at an elevated temperature without conversion to acrylic acid. This process can be integrated with downstream processes for producing other chemical and consumer products.
    Type: Application
    Filed: March 14, 2014
    Publication date: February 26, 2015
    Inventors: Cindy HOPPE, Sarah M. HOYT, Robert TENGLER, David DeCOSTER, Bradley HARKRADER, Patrick H. AU-YEUNG, Sanjib BISWAS, Pedro R. VARGAS, II, Raymond P. ROACH, Timothy Charles FRANK
  • Patent number: 8933179
    Abstract: A method of producing a compound of formula (i): wherein R=H or CH3 the method comprising exposing a source of a compound of formula (ii) to reaction conditions of temperature and pressure: formula (ii) wherein R is defined as above wherein, when R=CH3, the source of a compound of formula (ii) is exposed to reaction conditions of temperature and pressure while being in a liquid phase.
    Type: Grant
    Filed: December 21, 2010
    Date of Patent: January 13, 2015
    Assignee: Lucite International UK Limited
    Inventors: David William Johnson, Graham Ronald Eastham, Martyn Poliakoff, Thomas Andrew Huddle
  • Publication number: 20140377706
    Abstract: An aqueous solution containing 0.1-20 wt % of a substituted choline or thiocholine hydroxide is a useful developer for photosensitive resist materials. A resist pattern is formed by applying a chemically amplified positive resist composition onto a substrate to form a resist film, exposing the resist film to high-energy radiation, and developing the exposed resist film in an ammonium hydroxide-containing aqueous solution.
    Type: Application
    Filed: May 27, 2014
    Publication date: December 25, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Masaki Ohashi
  • Publication number: 20140364519
    Abstract: Ligand functionalized substrates, methods of making ligand functionalized substrates, and methods of using functionalized substrates are disclosed.
    Type: Application
    Filed: August 25, 2014
    Publication date: December 11, 2014
    Inventors: Catherine A. Bothof, Yi He, Jerald K. Rasmussen, Kannan Seshadri, Clinton P. Waller, JR., Douglas E. Weiss
  • Publication number: 20140357890
    Abstract: A method for efficiently producing t-butanol as a raw material of a methacrylic resin from isobutanol is described, including a step (1) of dehydrating isobutanol to obtain butenes, and a step (2) of hydrating the butenes to obtain t-butanol. A method for producing methacrolein and methacrylic acid is also described, which further includes a step (3) of dehydrating and oxidizing the obtained t-butanol to obtain methacrolein and methacrylic acid. An apparatus for performing the steps (1) to (3) is also described.
    Type: Application
    Filed: November 6, 2012
    Publication date: December 4, 2014
    Applicant: MITSUBISHI RAYON CO., LTD.
    Inventors: Ken Ooyachi, Toshiya Yasukawa, Shuji Akihara
  • Publication number: 20140316073
    Abstract: A polymeric composition that includes at least one polymer and an effective amount of a nanoparticulate component. The nanoparticulate component is at least one of inorganic functional nanoparticulate compounds and graphene in which the nanoparticulate component is associated with the polymer. The polymer disclosed herein can have electromagnetic activity. The resulting polymeric composition exhibit a measurable electrical conductivity (?) range of 10?14 to 4.7*106 (S/m) at 20° C. A polymeric precursor that includes at least one component selected from the group that includes isocyanates, polyisocyanates, MDI-terminated prepolymers and an effective amount of a nanoparticulate component. The nanoparticulate component is at least one of inorganic functional nanoparticulate component being at least one of inorganic functional nanoparticulate compounds and graphene that is associated with the prepolymer.
    Type: Application
    Filed: March 17, 2014
    Publication date: October 23, 2014
    Applicant: Mackinac Polymers LLC
    Inventors: Ralph Locke, Michael Kerman, Melissa Arredondo, William Cowell
  • Patent number: 8859804
    Abstract: Disclosed is a method for producing a (meth)acrylate ester wherein a high purity (meth)acrylate ester is obtained with a high yield, with a reduced loss of (meth)acrylic acid anhydride. In the method, (meth)acrylic acid is recovered with a high yield, and the (meth)acrylate ester is purified easily. Specifically disclosed is a method for producing a (meth)acrylate ester which comprises: (1) a step of producing (meth)acrylic acid anhydride by reacting a specific fatty acid anhydride and (meth)acrylic acid, while removing a by-produced fatty acid; (2) a step of obtaining a (meth)acrylate ester by reacting an alcohol and unpurified (meth)acrylic acid anhydride obtained in step (1) preferably at a temperature not less than 90° C.; and (3) a step of recovering (meth)acrylic acid by distillation preferably at a temperature not less than 90° C. The method may also comprise a step of heating or distilling the reaction liquid obtained in step (2) at a temperature not less than 90° C.
    Type: Grant
    Filed: February 4, 2010
    Date of Patent: October 14, 2014
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Ryuichi Ansai, Hiroyuki Nogami, Kuniyoshi Ogura
  • Publication number: 20140303338
    Abstract: A process for producing acrolein, comprising: a glycerin dehydration step of conducting dehydration reaction of glycerin to obtain an acrolein-containing gas; a partial-condensation step of cooling the acrolein-containing gas to condense a part of acrolein, water and a high-boiling substance contained in the acrolein-containing gas, thereby obtaining a purified gas and a condensate; and a separation step of separating the purified gas from the condensate; wherein a polymerization inhibitor is added to the acrolein-containing gas or the condensate in the partial-condensation step.
    Type: Application
    Filed: September 25, 2012
    Publication date: October 9, 2014
    Applicant: Nippon Shokubai Co., Ltd.
    Inventors: Hideaki Tsuneki, Masanori Nonoguchi, Koji Nishi
  • Publication number: 20140275575
    Abstract: The present application provides a method for producing an beta-lactone product. The method includes the steps of: reacting an epoxide, a solvent with a carbonylation catalyst and carbon monoxide to produce a reaction stream comprising a beta-lactone then separating a portion of the beta-lactone in the reaction stream from the solvent and carbonylation catalyst to produce: i) a beta-lactone stream with the beta-lactone, and ii) a catalyst recycling stream including the carbonylation catalyst and the high boiling solvent; and adding the catalyst recycling stream to the feed stream.
    Type: Application
    Filed: May 12, 2014
    Publication date: September 18, 2014
    Applicant: Novomer, Inc.
    Inventors: Scott D. Allen, Ronald R. Valente, Han Lee, Anna E. Cherian, Donald L. Bunning, Nye A. Clinton, Olan Stanley Fruchey, Bernard Duane Dombek
  • Publication number: 20140249274
    Abstract: A high functionality macromer that is the reaction product of (1) a polyisocyanate having an NCO group content of about from about 10% to about 33% having a functionality greater than 2, (2) at least one alcohol with reactive unsaturation, and (3) a hydroxyl group-containing polyether having an OH number of from 9 to 60 and a functionality of from 1 to 6 is used to produce a pre-formed stabilizer that is used to produce a high solids content polymer polyol.
    Type: Application
    Filed: March 4, 2013
    Publication date: September 4, 2014
    Applicant: Bayer MaterialScience LLC
    Inventor: Rick L. Adkins
  • Patent number: 8816123
    Abstract: A decarboxylation reaction of a (3-methyl-3-butenyl)malonic acid dialkyl ester, carried out by heating in the presence of water and a base, produces an alkyl 5-methyl-5-hexenoate. The decarboxylation reaction produces the alkyl 5-methyl-5-hexenoate inexpensively and effectively. The base can optionally be a tertiary amine compound or a heterocyclic amine compound. Producing the alkyl 5-methyl-5-hexenoate can optionally further include removing an alcohol.
    Type: Grant
    Filed: December 1, 2010
    Date of Patent: August 26, 2014
    Assignee: Kuraray Co., Ltd.
    Inventor: Katsuji Ujita
  • Patent number: 8816124
    Abstract: Disclosed is an energetic reactive plasticizer for a plastic bonded explosive (PBX), and specifically an energetic reactive plasticizer for PBX which has high performance and insensitiveness without a plasticizer leak by being bonded with a polymer binder for a plastic bonded explosive.
    Type: Grant
    Filed: August 8, 2013
    Date of Patent: August 26, 2014
    Assignee: Agency for Defense Development
    Inventors: Young Hwan Kwon, Jin Seuk Kim, Bum Jae Lee, In Joo Bae
  • Patent number: 8808960
    Abstract: A compound represented by the formula (I): wherein R1 represents a hydrogen atom etc., R2 and R3 each independently represent a hydrogen atom etc., R4 represents a C1-C8 divalent hydrocarbon group, R5 represents a single bond etc., and R6 represents an unsubstituted or substituted C6-C20 aromatic hydrocarbon group, a polymer comprising a structural unit derived from the compound represented by the formula (I) and a chemically amplified positive resist composition comprising the polymer, at least one acid generator and at least one solvent.
    Type: Grant
    Filed: March 8, 2010
    Date of Patent: August 19, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Akita, Isao Yoshida, Kazuhiko Hashimoto
  • Patent number: 8809451
    Abstract: According to the present invention, a polymer is obtained by polycondensation of a fluorinated dicarboxylic acid derivative of the general formula (M-1) or an acid anhydride of the fluorinated dicarboxylic acid with a polyfunctional compound having two to four reactive groups corresponding in reactivity to carbonyl moieties of the fluorinated dicarboxylic acid derivative or acid anhydride. [Chem. 134] AOCF2C-Q-CF2COA???(M-1) In the above formula, Q represents a divalent organic group having a substituted or unsubstituted aromatic ring; and A and A? each independently represent an organic group. This polymer exhibits a sufficiently low dielectric constant for use as a semiconductor protection film and has the capability of forming a film at a relatively low temperature of 250° C. or lower.
    Type: Grant
    Filed: February 18, 2010
    Date of Patent: August 19, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Yoshimi Isono, Satoru Narizuka, Hidehisa Nanai, Kazuhiro Yamanaka
  • Publication number: 20140228571
    Abstract: In a method of stabilizing acrylic compounds, a liquid phase containing at least one acrylic compound is mixed with at least one metal and at least one ligand. The acrylic compound can be acrylic acid, methacrylic acid, and their respective esters. The metal can be copper, manganese, and cerium. The ligand can be a quinoline compound of formula (I), an N-oxide of a compound of formula (I), 2,2?-bis(2,3-dihydro-3-oxoindolylidene), or an aliphatic y-dentate ligand with y being 2-6 and comprising at least two nitrogen atoms joined by aliphatic or aromatic C1-C4 bridges comprising y-2 further coordinating nitrogen atoms or heteroatoms: where X is OH, NH2, O—(C1-C4)-alkyl, O—C(O)—(C1-C4)-alkyl, or O—C(O)-phenyl; R1 is H, or (C1-C4)-alkyl; R2 is H, (C1-C4)-alkyl, Cl, Br, or SO3H; and R3 is H, Cl or Br.
    Type: Application
    Filed: December 12, 2013
    Publication date: August 14, 2014
    Applicant: BASF SE
    Inventors: Tobias Johannes KORN, Peter Zurowski, Thorsten Friese, Sylke Haremza, Ulrich Jäger, Steffen Rissel, Volker Schliephake
  • Patent number: 8802889
    Abstract: A process for production of allyl acetate includes steps of reacting acetic acid 3, oxygen 1 and propylene 2 in the presence of a catalyst in an oxidation reactor 5 to form allyl acetate and water; separating the unreacted acetic acid by a distillation column 9; and recovering an acetic acid-containing liquid which contains acetic acid and returning the acetic acid-containing liquid to the oxidation reactor 5 via an acetic acid-water evaporator 4, the process further including a heating step of heating a process liquid which contains the acetic acid-containing liquid to a temperature of 80 to 250° C. by a heater.
    Type: Grant
    Filed: September 20, 2011
    Date of Patent: August 12, 2014
    Assignee: Showa Denko K.K.
    Inventor: Wataru Oguchi
  • Patent number: 8796475
    Abstract: The present application provides a method for producing an beta-lactone product. The method includes the steps of: reacting an epoxide, a solvent with a carbonylation catalyst and carbon monoxide to produce a reaction stream comprising a beta-lactone then separating a portion of the beta-lactone in the reaction stream from the solvent and carbonylation catalyst to produce: i) a beta-lactone stream with the beta-lactone, and ii) a catalyst recycling stream including the carbonylation catalyst and the high boiling solvent; and adding the catalyst recycling stream to the feed stream.
    Type: Grant
    Filed: April 10, 2013
    Date of Patent: August 5, 2014
    Assignee: Novomer, Inc.
    Inventors: Scott D. Allen, Ronald R. Valente, Han Lee, Anna E. Cherian, Donald L. Bunning, Nye A. Clinton, Olan Stanley Fruchey, Bernard Duane Dombek
  • Patent number: 8785677
    Abstract: The present invention is directed to a novel compound, but-2-enoic acid 1,2-dimethyl-butyl ester, and a method of improving, enhancing or modifying a fragrance formulation through the addition of an olfactory acceptable amount of but-2-enoic acid 1,2-dimethyl-butyl ester.
    Type: Grant
    Filed: February 25, 2013
    Date of Patent: July 22, 2014
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, Richard A. Weiss, James Anthony Lasome
  • Publication number: 20140199631
    Abstract: A polymer for resist use is obtainable from a monomer having formula (1) wherein R1 is H, CH3 or CF3 and R2 is H or an acid labile group. A resist composition comprising the polymer displays a high sensitivity and a high dissolution contrast during both alkaline development and organic solvent development.
    Type: Application
    Filed: December 17, 2013
    Publication date: July 17, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masayoshi Sagehashi, Koji Hasegawa, Kazuhiro Katayama
  • Patent number: 8772532
    Abstract: Provided are processes for the production of (meth)acrylic esters of polyols, in which for 80 mol % or more of the esters, all of the OH groups of the polyols are esterified. Certain processes relate to reaction of polyols with acrylic acid and/or methacrylic acid in the presence of acidic esterification catalysts and in the presence of polymerization inhibitors, operating with reaction mixtures which are liquid at reaction temperature and are free from nonreacting solvents and/or azeotropic entrainers, the resultant water of condensation being stripped from the gas phase of the reaction space, and the (meth)acrylic acid is metered in three or more portions.
    Type: Grant
    Filed: August 2, 2012
    Date of Patent: July 8, 2014
    Assignee: Cognis IP Management GmbH
    Inventors: Juergen Baro, Jean-Marc Ballin
  • Patent number: 8772533
    Abstract: The present invention is directed to a novel compound, but-2-enoic acid 1-ethyl-2-methyl-propyl ester, and a method of improving, enhancing or modifying a fragrance formulation through the addition of an olfactory acceptable amount of but-2-enoic acid 1-ethyl-2-methyl-propyl ester.
    Type: Grant
    Filed: February 25, 2013
    Date of Patent: July 8, 2014
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard K. Payne, Feng Geng, Gary J. Mertz
  • Publication number: 20140171677
    Abstract: A method of isomerizing a substance includes combining a substance including a terminal alkenyl group and a substance including a fluorosulfonic acid group in a reaction mixture, and forming a substance including a 2-alkenyl group from the substance including a terminal alkenyl group in the reaction mixture. The method may be used to functionalize a substance, as the substance including a 2-alkenyl group can be reacted with a functionalizing agent to form a substance including a first functional group. The methods may be used to form a dicarboxylic acid, such as suberic acid, from a renewable feedstock.
    Type: Application
    Filed: November 26, 2013
    Publication date: June 19, 2014
    Applicant: Elevance Renewable Sciences, Inc.
    Inventors: Paul A. Bertin, Jordan R. Quinn
  • Patent number: 8735436
    Abstract: The present disclosure relates to lipid compounds of the general formula (I): R1-O—C(R2)(R3)-X??(I) wherein R1 is a C10-C22 alkyl group, a C10-C22 alkenyl group having 1-6 double bonds, or a C10-C22 alkynyl group having 1-6 triple bonds; R2 and R3 are the same or different and may be chosen from different substituents; and X is a carboxylic acid or a derivative thereof, such as a carboxylic ester, a carboxylic anhydride, a phospholipid, triglyceride, or a carboxamide; or a pharmaceutically acceptable salt, solvate, solvate of such salt or a prodrug thereof. The present disclosure also relates to pharmaceutical compositions and lipid compositions comprising at least one compound according to the present disclosure, and to such compounds for use as medicaments or for use in therapy, in particular for the treatment of diseases related to the cardiovascular, metabolic, and inflammatory disease area.
    Type: Grant
    Filed: May 7, 2010
    Date of Patent: May 27, 2014
    Assignee: Pronova Biopharma Norge AS
    Inventors: Ragnar Hovland, Anne Kristin Holmeide, Tore Skjæret, Morten Brændvang
  • Publication number: 20140135523
    Abstract: A continuous process for preparing (meth)acrylates of C10-alcohol mixtures by reaction of glacial (meth)acrylic acid with an isomer mixture of C10-alcohols composed of 2-propylheptanol as the main isomer and at least one of the C10-alcohols 2-propyl-4-methylhexanol, 2-propyl-5-methylhexanol, 2-isopropylheptanol, 2-isopropyl-4-methylhexanol, 2-isopropyl-5-methylhexanol and/or 2-propyl-4,4-dimethylpentanol, and the use of a diester of dicarboxylic acids which have been esterified with N-oxyl-containing compounds as polymerization inhibitors in such a process.
    Type: Application
    Filed: September 27, 2013
    Publication date: May 15, 2014
    Applicant: BASF SE
    Inventors: Ulrich JAEGER, Volker SCHLIEPHAKE, Ortmund LANG, Jochen PETZOLDT, Tobias Johannes KORN, Virginie BETTE, Claus HECHLER
  • Publication number: 20140128465
    Abstract: The present invention includes methods for producing and purifying esters of polyunsaturated fatty acids that include reacting a composition having triglycerides with polyunsaturated fatty acid residues in the presence of an alcohol and a base to produce an ester of a polyunsaturated fatty acid from the triglycerides. The composition can be a polyunsaturated fatty acid-containing composition that has not been conventionally processed. The reacted composition can be further processed by distillation.
    Type: Application
    Filed: January 13, 2014
    Publication date: May 8, 2014
    Inventors: Krishna Raman, Jung Lee, Neil Leininger, Chris Luigart
  • Patent number: 8716516
    Abstract: The present invention relates to a process for preparing polyalkylene glycol di(meth)acrylates by reacting polyalkylene glycol with (meth)acrylic anhydride, wherein the reaction mixture contains at most 0.5% by weight of metal compounds and/or amines, the reaction is carried out in the presence of polymerization inhibitors and the reaction temperature is at least 60° C.
    Type: Grant
    Filed: May 5, 2009
    Date of Patent: May 6, 2014
    Assignee: Evonik Röhm GmbH
    Inventors: Thorben Schuetz, Joachim Knebel, Mario Gomez Andreu
  • Publication number: 20140087445
    Abstract: Ligand functionalized substrates, methods of making ligand functionalized substrates, and methods of using functionalized substrates are disclosed.
    Type: Application
    Filed: November 27, 2013
    Publication date: March 27, 2014
    Applicant: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Catherine A. Bothof, Yi He, Jerald K. Rasmussen, Kannan Seshadri, Clinton P. Waller, JR., Douglas E. Weiss
  • Patent number: 8637623
    Abstract: Disclosed is a monomer having an electron-withdrawing substituent and a lactone skeleton, represented by Formula (1), wherein Ra represents, e.g., hydrogen or an alkyl group having 1 to 6 carbons; R1 represents, e.g., a halogen or an alkyl or haloalkyl group having 1 to 6 carbons; “A” represents an alkylene group having 1 to 6 carbons, oxygen, sulfur, or is nonbonding; “m” denotes an integer of 0 to 8; Xs each represent an electron-withdrawing substituent; “n” denotes an integer of 1 to 9; and Y represents a bivalent organic group having 1 to 6 carbons. The monomer is useful as a monomer component typically for a highly functional polymer, because, when the monomer is applied to a resist resin, the resin is stable and resistant to chemicals, is highly soluble in organic solvents, and has improved hydrolyzability and/or solubility in water after hydrolysis.
    Type: Grant
    Filed: February 3, 2009
    Date of Patent: January 28, 2014
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hiroshi Koyama, Kyuhei Kitao, Akira Eguchi
  • Publication number: 20140005349
    Abstract: The present invention generally relates to alcohol-terminated polyisobutylene (PIB) compounds, and to a process for making such compounds. In one embodiment, the present invention relates to primary alcohol-terminated polyisobutylene compounds, and to a process for making such compounds. In still another embodiment, the present invention relates to polyisobutylene compounds that can be used to synthesize polyurethanes, to polyurethane compounds made via the use of such polyisobutylene compounds, and to processes for making such compounds. In yet another embodiment, the present invention relates to primary alcohol-terminated polyisobutylene compounds having two or more primary alcohol termini and to a process for making such compounds. In yet another embodiment, the present invention relates to primary terminated polyisobutylene compounds having two or more primary termini selected from amine groups or methacrylate groups.
    Type: Application
    Filed: September 4, 2013
    Publication date: January 2, 2014
    Applicant: The University of Akron
    Inventors: Joseph P. Kennedy, Yongmoon Kwon, Subramanyam Ummadisetty
  • Patent number: 8609321
    Abstract: A radiation-sensitive resin composition includes a polymer having a structural unit represented by a formula (I). In the formula (I), R1 represents a hydrogen atom or a methyl group. X represents a bivalent alicyclic hydrocarbon group not having or having a substituent. Y represents a bivalent hydrocarbon group having 1 to 20 carbon atoms. R2 represents a methyl group or a trifluoromethyl group.
    Type: Grant
    Filed: March 8, 2013
    Date of Patent: December 17, 2013
    Assignee: JSP Corporation
    Inventors: Hiromitsu Nakashima, Reiko Kimura, Kazuo Nakahara, Mitsuo Sato