Patents by Inventor Jean-Luc Couturier

Jean-Luc Couturier has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 9221745
    Abstract: A process for synthesizing a long-chain saturated ?,?-amino ester (acid) including from 6 to 17 carbon atoms, said process including a first step of cross metathesis between a first acrylic compound chosen from acrylonitrile, acrylic acid or an acrylic ester and a second monounsaturated compound including at least one nitrile, acid or ester trivalent function, one of these compounds including a nitrile function and the other an acid or ester function, in the presence of a ruthenium carbene metathesis catalyst, and a second step of hydrogenation of the monounsaturated nitrile-ester (acid) obtained, wherein said monounsaturated compound including at least one nitrile, acid or ester trivalent function has previously been subjected to a purification by thermal and/or chemical treatment.
    Type: Grant
    Filed: July 27, 2012
    Date of Patent: December 29, 2015
    Assignee: ARKEMA FRANCE
    Inventors: Jean-Luc Couturier, Jean-Luc Dubois
  • Publication number: 20150353479
    Abstract: A process for the synthesis of an unsaturated product by cross metathesis between a first unsaturated compound having at least 8 carbon atoms and a second unsaturated compound having less than 8 carbon atoms, including: feeding a reactor with the first unsaturated compound, the second unsaturated compound and a metathesis catalyst; withdrawing an output stream, at the output of the reactor; separating the output stream, making it possible to recover at least: on the one hand, the unsaturated product and, on the other hand, the first unsaturated compound and the second unsaturated compound; recycling the first unsaturated compound and the second unsaturated compound to the reactor; in which the first unsaturated compound is capable of producing an unsaturated coproduct, including at least 14 carbon atoms, by homometathesis; and in which the flow rates for feeding the reactor with first unsaturated compound and with second unsaturated compound are adjusted.
    Type: Application
    Filed: January 7, 2014
    Publication date: December 10, 2015
    Applicant: ARKEMA FRANCE
    Inventors: Jean-Luc DUBOIS, Jean-Luc COUTURIER
  • Publication number: 20150344416
    Abstract: A process for the synthesis of an unsaturated product by cross metathesis between a first unsaturated compound having at least 8 carbon atoms and a second unsaturated compound having less than 8 carbon atoms, the first unsaturated compound being capable of producing an unsaturated coproduct comprising more than 14 carbon atoms, by homometathesis, said process including at least one production phase which includes: feeding a reactor with the first unsaturated compound; feeding the reactor with the second unsaturated compound; feeding the reactor with at least a first metathesis catalysts, then feeding the reactor with at least a second metathesis catalyst; withdrawing a product stream arising from the reactor; the turnover number of the first catalyst being higher than the turnover number of the second catalyst so as to achieve the same target degree of conversion of the first unsaturated compound.
    Type: Application
    Filed: January 7, 2014
    Publication date: December 3, 2015
    Applicant: ARKEMA FRANCE
    Inventors: Jean-Luc DUBOIS, Jean-Luc COUTURIER
  • Publication number: 20150336879
    Abstract: A process for the synthesis of a monounsaturated nitrile-ester (acid) by cross metathesis starting from an unsaturated compound I including at least one trivalent nitrile, acid or ester functional group, wherein the process includes a stage in which two types of cross metathesis are alternated consecutively: — a first type of cross metathesis cm1 with an acrylic compound II chosen from acrylonitrile, acrylic acid or an acrylic ester, one of the compounds I or II including a nitrile functional group and the other of these compounds II or I including an acid or ester functional group, and—a second type of cross metathesis cm2 with a light C2 to C4 alkene compound III. Also, a process for the synthesis of an ?,?-amino ester (acid) obtained by a process including a stage in which the two types of cross metathesis defined above are alternated consecutively, followed by a hydrogenation stage.
    Type: Application
    Filed: January 7, 2013
    Publication date: November 26, 2015
    Applicant: ARKEMA FRANCE
    Inventors: Jean-Luc DUBOIS, Jean-Luc COUTURIER
  • Patent number: 9096490
    Abstract: The subject matter of the invention is a process for synthesizing a saturated long-chain ?,?-amino ester (acid) obtained in a first step by cross-metathesis between an acrylic first compound and a monounsaturated second compound comprising at least one nitrile, acid or ester trivalent function, one of these compounds comprising a nitrile function and the other an acid or ester function, in the presence of a ruthenium carbene metathesis catalyst, and in a second step by hydrogenation of the monounsaturated nitrile ester (acid) obtained in the presence of the metathesis catalyst of the preceding stop, acting as a hydrogenation catalyst.
    Type: Grant
    Filed: May 9, 2011
    Date of Patent: August 4, 2015
    Assignees: ARKEMA FRANCE, UNIVERSITE DE RENNES 1, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
    Inventors: Jean Luc Couturier, Jean Luc Dubois, Xiaowei Miao, Cedric Fischmeister, Christian Bruneau, Pierre Dixneuf
  • Patent number: 9073872
    Abstract: The present invention relates to nitrogenous associative molecules comprising at least one unit rendering them capable of associating with one another or with a filler by noncovalent bonds, and comprising a function capable of reacting with a polymer containing unsaturations so as to form a covalent bond with said polymer.
    Type: Grant
    Filed: July 12, 2011
    Date of Patent: July 7, 2015
    Assignee: ARKEMA FRANCE
    Inventors: Nicolas Seeboth, Serguey Ivanov, Jean-Luc Couturier, Manuel Hidalgo
  • Patent number: 9045432
    Abstract: A compound includes at least one group Q and at least one group A linked together by at least one “spacer” group Sp, in which: group Q includes a dipole containing at least one nitrogen atom, preferably a nitrile oxide, nitrone, or nitrile imine function; group A contains at least one nitrogen atom, and is preferably an imidazolidinyl, ureyl, bis-ureyl, ureido-pyrimidyl, and triazolyl group; and Sp is an atom or a group of atoms forming a link between Q and A, preferably, a linear, branched or cyclic hydrocarbon-based optionally substituted chain, and may contain one or more aromatic radicals and/or heteroatoms. The compound may react with an unsaturated polymer forming a covalent bond with the polymer. The compound is useful for providing good interaction between fillers and polymers by establishing labile, non-covalent bonds between the polymer chains and the filler, thereby limiting processing problems.
    Type: Grant
    Filed: July 12, 2011
    Date of Patent: June 2, 2015
    Assignee: Arkema France
    Inventors: Nicolas Seeboth, Serguey Ivanov, Jean-Luc Couturier, Manuel Hidalgo
  • Patent number: 8975363
    Abstract: A shock absorber is prepared from a material formed from branched molecules comprising associative groups. The branched molecules each contains at least bifunctional fragments and at least trifunctional fragments joined together by ester or thioester bridges alone or in combination with amide or urea bridges.
    Type: Grant
    Filed: March 29, 2010
    Date of Patent: March 10, 2015
    Assignee: Arkema France
    Inventors: Manuel Hidalgo, Nicolas Dufaure, Jean-Luc Couturier, Bruno Hemelryck
  • Patent number: 8889771
    Abstract: The invention relates to the field of plasticizers, compounds used as additives in polymers for facilitating the transformation thereof or modifying the mechanical properties thereof especially rigidity.
    Type: Grant
    Filed: April 18, 2011
    Date of Patent: November 18, 2014
    Assignee: Arkema France
    Inventors: Nicolas Dufaure, Jean-Luc Couturier, Manuel Hidalgo
  • Patent number: 8884041
    Abstract: A method for synthesizing ?-amino-alkanoic acids or the esters thereof from natural unsaturated fatty acids passing through an intermediate ?-unsaturated nitrile compound. The method is simple to implement and, relative to known methods, avoids the environmental constraints and economic disadvantages resulting from the reaction by-products. The method includes synthesizing an ?-amino acid (ester) of formula R3OOC—(CH2)q-CH2NH2, in which R3 is H or an n-butyl radical and q is an integral index of between 2 and 13, from a monounsaturated fatty acid (ester) of formula (R1-CH?CH—(CH2)p-COO)xR2, in which x represents 1, 2 or 3, R1 is H or a hydrocarbon radical comprising from 4 to 11 carbon atoms and, where appropriate, a hydroxyl function, R2 is H or an alkyl radical comprising from 2 to 4 carbon atoms, and may contain one or more heteroatoms, and p is an integral index of between 2 and 11, including a reaction step of ammoniation.
    Type: Grant
    Filed: July 26, 2012
    Date of Patent: November 11, 2014
    Assignee: Arkema France
    Inventors: Jean-Luc Couturier, Jean-Luc Dubois
  • Publication number: 20140323684
    Abstract: A method for synthesizing a ?-amino acid compound having formula HOOC—R?—CH2NH2, where R is an alkyl radical including between 6 and 15 carbon atoms or an alkylene radical including between 6 and 15 carbon atoms and between 0 and 2 unsaturations. The method including the following steps: 1) hydroformylation of an unsaturated fatty nitrile selected from compounds having formula R1—CH?CH—[(CH2)q—CH?CH]m—(CH2)r—CN, said step consisting in reacting the nitrile with the carbon monoxide and dihydrogen such as to obtain at least one fatty nitrile aldehyde having formula HOC—R?—CN; 2) dioxygen oxidation, wherein the nitrile aldehyde obtained in step 1) is converted into fatty nitrile acid having formula HOOC—R?—CN; and 3) reduction, in which the nitrile acid obtained in step 2) is converted into co-amino acid having formula HOOC—R?—CH2NH2.
    Type: Application
    Filed: December 3, 2012
    Publication date: October 30, 2014
    Inventors: Jean-Luc Dubois, Jean-Luc Couturier, Jean-François Carpentier, Jérémy Ternel
  • Patent number: 8865806
    Abstract: The invention relates to the field of plasticizers, compounds used as additives in polymers for facilitating the transformation thereof or modifying the mechanical properties thereof, especially rigidity.
    Type: Grant
    Filed: April 18, 2011
    Date of Patent: October 21, 2014
    Assignee: Arkema France
    Inventors: Nicolas Dufaure, Julien Jouanneau, Guillaume Le, Jean-Luc Couturier, Manuel Hidalgo
  • Patent number: 8835661
    Abstract: A process for the synthesis of C11 and C12 ?-amino-alkanoic acid esters including a step of continuous nitrilation in the gas phase or in a mixed gas-liquid phase, a step of metathesis and a step of reduction by hydrogenation, using, as raw material, C10 and C11 ?-alkenoic acid esters.
    Type: Grant
    Filed: July 26, 2012
    Date of Patent: September 16, 2014
    Assignee: Arkema France
    Inventors: Jean-Luc Couturier, Jean-Luc Dubois
  • Publication number: 20140200358
    Abstract: A process for the synthesis of C11 and C12 ?-amino-alkanoic acid esters including a step of continuous nitrilation in the gas phase or in a mixed gas-liquid phase, a step of metathesis and a step of reduction by hydrogenation, using, as raw material, C10 and C11 ?-alkenoic acid esters.
    Type: Application
    Filed: July 26, 2012
    Publication date: July 17, 2014
    Applicant: ARKEMA FRANCE
    Inventors: Jean-Luc Couturier, Jean-Luc Dubois
  • Patent number: 8779213
    Abstract: The present invention relates to a bio-based glutaraldehyde compound and to the different non-fossil, natural raw material manufacture methods thereof. To prepare said compound, glycerol created by the methanolysis of vegetable oil or animal fat is used, leading after dehydration to acrolein that is caused to react with a vinyl/alkyl/ether as per a Diels-Alder cyclization reaction, followed by hydrolysis so as to obtain the bio-based glutaraldehyde of the invention. Sugars containing five carbon atoms, that is, pentoses created from for example hemicellulose, may also be used, leading after dehydration to furfural, which leads, after complete hydrogenation followed by selective oxidation, to the bio-based glutaraldehyde of the invention.
    Type: Grant
    Filed: October 19, 2010
    Date of Patent: July 15, 2014
    Assignee: Arkema France
    Inventors: Jean Luc Couturier, Jean Luc Dubois
  • Publication number: 20140194584
    Abstract: The invention relates to a process for the synthesis of a monounsaturated nitrile-ester (acid) by cross metathesis starting from an unsaturated compound I comprising at least one trivalent nitrile, acid or ester functional group, characterized in that it comprises a stage in which two types of cross metathesis are alternated consecutively: a first type of cross metathesis cm1 with an acrylic compound II chosen from acrylonitrile, acrylic acid or an acrylic ester, one of the compounds I or II comprising a nitrile functional group and the other of these compounds II or I comprising an acid or ester functional group, and a second type of cross metathesis cm2 with a light C2 to C4 alkene compound III, preferably with ethylene. The invention also relates to a process for the synthesis of an ?,?-amino ester (acid) obtained by a process comprising a stage in which the two types of cross metathesis defined above are alternated consecutively, followed by a hydrogenation stage.
    Type: Application
    Filed: January 7, 2013
    Publication date: July 10, 2014
    Inventors: Jean-Luc Dubois, Jean-Luc Couturier
  • Publication number: 20140187808
    Abstract: A method for synthesizing ?-amino-alkanoic acids or the esters thereof from natural unsaturated fatty acids passing through an intermediate ?-unsaturated nitrile compound. The method is simple to implement and, relative to known methods, avoids the environmental constraints and economic disadvantages resulting from the reaction by-products. The method includes synthesizing an ?-amino acid (ester) of formula R3OOC—(CH2)q—CH2NH2, in which R3 is H or an n-butyl radical and q is an integral index of between 2 and 13, from a monounsaturated fatty acid (ester) of formula (R1-CH?CH—(CH2)p-COO) xR2, in which x represents 1, 2 or 3, R1 is H or a hydrocarbon radical comprising from 4 to 11 carbon atoms and, where appropriate, a hydroxyl function, R2 is H or an alkyl radical comprising from 2 to 4 carbon atoms, and may contain one or more heteroatoms, and p is an integral index of between 2 and 11, including a reaction step of ammoniation.
    Type: Application
    Filed: July 26, 2012
    Publication date: July 3, 2014
    Applicant: ARKEMA FRANCE
    Inventors: Jean-Luc Couturier, Jean-Luc Dubois
  • Publication number: 20140163196
    Abstract: A process for synthesizing a long-chain saturated ?,?-amino ester (acid) including from 6 to 17 carbon atoms, said process including a first step of cross metathesis between a first acrylic compound chosen from acrylonitrile, acrylic acid or an acrylic ester and a second monounsaturated compound including at least one nitrile, acid or ester trivalent function, one of these compounds including a nitrile function and the other an acid or ester function, in the presence of a ruthenium carbene metathesis catalyst, and a second step of hydrogenation of the monounsaturated nitrile-ester (acid) obtained, wherein said monounsaturated compound including at least one nitrile, acid or ester trivalent function has previously been subjected to a purification by thermal and/or chemical treatment.
    Type: Application
    Filed: July 27, 2012
    Publication date: June 12, 2014
    Applicant: ARKEMA FRANCE
    Inventors: Jean-Luc Couturier, Jean-Luc Dubois
  • Publication number: 20130345388
    Abstract: The invention relates to a process for synthesizing a nitrile-fatty acid (heminitrile) from unsaturated fatty acids, in the form of an acid or a simple ester or a “complex” ester of triglyceride type, which is first of all converted into an unsaturated fatty nitrile which is subjected to oxidative cleavage using H2O2 as oxidizing agent. This process can be used for preparing polyamide monomers, such as ?-amino acids or diamines or diacids equivalent to said heminitrile and for obtaining polyamides from raw materials which are of natural origin and from a renewable source.
    Type: Application
    Filed: December 14, 2011
    Publication date: December 26, 2013
    Applicant: ARKEMA FRANCE
    Inventors: Markus Brandhorst, Jean-Luc Couturier, Jean-Luc Dubois
  • Publication number: 20130261255
    Abstract: A subject matter of the present invention is a composition comprising: (i) from 0.1 to 49 parts by weight of at least one thermoplastic condensation polymer; and (ii) from 51 to 99.9 parts by weight of at least one supramolecular polymer capable of being obtained by the reaction of at least one at least trifunctional compound (A) carrying first and second functional groups with: at least one compound (B) carrying, on the one hand, at least one reactive group capable of reacting with the first functional groups of (A) and, on the other hand, at least one associative group; and at least one at least bifunctional compound (C), the functional groups of which are capable of reacting with the second functional groups of the compound (A) in order to form ester, thioester or amide bridges.
    Type: Application
    Filed: October 18, 2011
    Publication date: October 3, 2013
    Applicant: Arkema France
    Inventors: Yves Deyrail, Anthony Dufrenne, Samuel Devisme, Nicolas Dufaure, Jean-Luc Couturier, Bruno Van Hemelryck, Manuel Hidalgo