公开(公告)号：US20230145123A1

公开(公告)日：2023-05-11

申请号：US17783018

申请日：2020-12-14

Applicant: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN

Inventor： Julien Thuilliez ,  Robert Ngo ,  François Jean-Baptiste-Dit-Dominique

IPC: C08F297/06 ,  C08F236/06

CPC classification number: C08F297/06 ,  C08F236/06

Abstract: The invention relates to a diorganomagnesium compound of formula RB—Mg—RA, RA being different from R8, RA being a polymer chain containing units of a monomer chosen from the group of monomers consisting of 1,3-dienes, aromatic α-monoolefins and mixtures thereof, RB comprising a benzene nucleus substituted with a magnesium atom, one of the carbon atoms of the benzene nucleus ortho to the magnesium being substituted with a methyl, an ethyl, an isopropyl or forming a ring with the carbon atom which is its closest neighbour and which is meta to the magnesium, the other carbon atom of the benzene nucleus ortho to the magnesium being substituted with a methyl, an ethyl or an isopropyl, on condition that if one of the two ortho carbon atoms is substituted with an isopropyl, the second ortho carbon atom is not substituted with an isopropyl.

公开(公告)号：US11498985B2

公开(公告)日：2022-11-15

申请号：US16606371

申请日：2018-04-16

Applicant: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN

Inventor： Julien Thuilliez ,  Nuno Pacheco

IPC: C08F210/02 ,  C08F2/06

Abstract: A process for the synthesis of an ethylene/butadiene copolymer is provided. The process is continuous and comprises the following steps: a. feeding at least one stirred polymerization reactor with a mixture of ethylene, butadiene, hydrocarbon-based solvent and catalytic system allowing the formation of cyclic trans-1,2-cyclohexane units in the polymer chain with a mole ratio of ethylene to the sum of the ethylene and butadiene monomers ranging from 0.5 to 0.99; the concentration of ethylene and butadiene monomers in the polymerization reaction medium being less than 15% by weight; the operating pressure of the reactor is greater than or equal to the saturated vapour pressure of the polymerization reaction medium; and the polymerization temperature is greater than 90° C.; b. recovering the ethylene/butadiene copolymer, this copolymer comprising, statistically distributed, ethylene units, butadiene units and trans-1,2-cyclohexane units, the molar fraction of ethylene units in the copolymer being greater than or equal to 50%.

公开(公告)号：US10822475B2

公开(公告)日：2020-11-03

申请号：US16062343

申请日：2016-12-16

Applicant: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN

Inventor： Julien Thuilliez ,  Nuno Pacheco

IPC: C08L9/00 ,  C08F210/02 ,  C08F236/06 ,  C08F4/6192 ,  C08F210/16

Abstract: An ethylene/butadiene copolymer comprising statistically distributed ethylene units butadiene units, and trans-1,2-cyclohexane units is provided. The molar fraction of ethylene units in the copolymer is greater than or equal to 50%, relative to the total number of moles of ethylene, butadiene and trans-1,2-cyclohexane units. The microstructure of the copolymer is homogeneous. A process for preparing such a copolymer and also to the uses of this copolymer, in particular in rubber compositions for tires, is also provided.

公开(公告)号：US09315590B2

公开(公告)日：2016-04-19

申请号：US13709446

申请日：2012-12-10

Applicant: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN ,  MICHELIN RECHERCHE ET TECHNIQUE S.A. ,  CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE ,  ECOLE POLYTECHNIQUE

Inventor： Guillaume Cortial ,  Pascal Le Floch ,  Francois Nief ,  Julien Thuilliez

IPC: C08F4/50 ,  C08F4/52 ,  C08F4/46 ,  C08L15/00 ,  C08F236/08 ,  C08F236/06

CPC classification number: C08F4/50 ,  C08F4/463 ,  C08F4/52 ,  C08F136/06 ,  C08F236/06 ,  C08F236/08 ,  C08K3/04 ,  C08L15/00 ,  C08F4/545 ,  C08L19/006 ,  C08F36/04

Abstract: The present invention relates to a novel catalytic system for polymerization, and more particularly for preparing conjugated diene polymers bearing a polar function at the chain end. This catalytic system is based on a metal salt of a rare-earth metal and, as alkylating agent, an organometallic compound based on a metal belonging to the 2nd column or the 13th column of the Periodic Table, capable of transferring a polar function to the diene elastomer during the conjugated diene polymerization step. The novel catalytic system makes it possible to reduce the steps for synthesizing a chain-end functionalized elastomer, while ensuring optimal functionalization, advantageously close or equal to 100%.

Abstract translation: 本发明涉及一种用于聚合的新型催化体系，更具体地说涉及在链末端制备具有极性官能团的共轭二烯聚合物。 该催化体系基于稀土金属的金属盐，并且作为烷基化剂，基于属于周期表第二列或第十三列的金属的有机金属化合物，其能够将极性官能团转移到 二烯烃弹性体。 新颖的催化体系使得有可能减少合成链端官能化弹性体的步骤，同时确保最佳官能化，有利地接近或等于100％。

公开(公告)号：US20130274407A1

公开(公告)日：2013-10-17

申请号：US13709446

申请日：2012-12-10

Applicant: Francoise Hervagault ,  Elaine Le Floch ,  Clémence Le Floch ,  Paul Le Floch ,  COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN ,  ECOLE POLYTECHNIQUE ,  CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE ,  MICHELIN RECHERCHE ET TECHNIQUE S.A.

Inventor： Guillaume CORTIAL ,  Pascal Le Floch ,  Francois Nief ,  Julien Thuilliez

IPC: C08F4/50 ,  C08F4/46 ,  C08F4/52

CPC classification number: C08F4/50 ,  C08F4/463 ,  C08F4/52 ,  C08F136/06 ,  C08F236/06 ,  C08F236/08 ,  C08K3/04 ,  C08L15/00 ,  C08F4/545 ,  C08L19/006 ,  C08F36/04

Abstract: The present invention relates to a novel catalytic system for polymerization, and more particularly for preparing conjugated diene polymers bearing a polar function at the chain end. This catalytic system is based on a metal salt of a rare-earth metal and, as alkylating agent, an organometallic compound based on a metal belonging to the 2nd column or the 13th column of the Periodic Table, capable of transferring a polar function to the diene elastomer during the conjugated diene polymerization step. The novel catalytic system makes it possible to reduce the steps for synthesizing a chain-end functionalized elastomer, while ensuring optimal functionalization, advantageously close or equal to 100%.

Abstract translation: 本发明涉及一种用于聚合的新型催化体系，更具体地说涉及在链末端制备具有极性官能团的共轭二烯聚合物。 该催化体系基于稀土金属的金属盐，并且作为烷基化剂，基于属于周期表第二列或第十三列的金属的有机金属化合物，其能够将极性官能团转移到 二烯烃弹性体。 新颖的催化体系使得有可能减少合成链端官能化弹性体的步骤，同时确保最佳官能化，有利地接近或等于100％。

公开(公告)号：US12043680B2

公开(公告)日：2024-07-23

申请号：US16972360

申请日：2019-05-27

Applicant: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN

Inventor： José-Carlos Araujo Da Silva ,  Vincent Lafaquiere ,  Emma Moreso ,  Julien Thuilliez ,  Aurélie Triguel

IPC: C08F210/04 ,  B60C1/00 ,  C08F4/54 ,  C08F210/02 ,  C08K3/013 ,  C08L9/00 ,  C08L23/08

CPC classification number: C08F210/04 ,  B60C1/00 ,  C08F4/545 ,  C08F210/02 ,  C08K3/013 ,  C08L9/00 ,  C08L23/083

Abstract: A copolymer of ethylene and of isoprene, which comprises from 10 to 35 mol % of isoprene units, at least 70% of which are in the 3,4 configuration and a portion of which is in the 1,2 configuration is provided. A copolymer of this type with a reduced crystallinity is synthesized with a much higher productivity than its homologues of ethylene and of butadiene, and also confers improved curing properties on rubber compositions.

公开(公告)号：US10934377B2

公开(公告)日：2021-03-02

申请号：US16320014

申请日：2017-07-24

Applicant: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN

Inventor： Vincent Lafaquiere ,  Julien Thuilliez

IPC: C08F4/52 ,  C08F4/56 ,  C08F236/04 ,  C08F236/06 ,  C08F210/18 ,  C07F3/02 ,  C07F17/00 ,  C08F110/02 ,  C08F236/08 ,  C07F5/00

Abstract: A catalytic system based at least on a preformation monomer which is ethylene or a mixture of ethylene and of a conjugated diene, on a metallocene of formula {P(Cp1)(Cp2)Y} or Cp3Cp4Y and on an organometallic compound as cocatalyst, Y denoting a group comprising a metal atom which is a rare earth metal, the Cp1, Cp2, Cp3 and Cp4 groups, which are identical or different, being selected from the group consisting of fluorenyl groups, cyclopentadienyl groups and indenyl groups, the groups being substituted or unsubstituted, and P being a group bridging the two Cp1 and Cp2 groups and comprising a silicon or carbon atom, is provided. Such a catalytic system exhibits an improved stability of the catalytic activity over time, in particular on storage.

公开(公告)号：US10513150B2

公开(公告)日：2019-12-24

申请号：US15735531

申请日：2016-06-16

Applicant: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN

Inventor： Séverin Dronet ,  Julien Thuilliez

IPC: B60C1/00 ,  C08F236/06 ,  C08F236/08 ,  C08G8/02 ,  C08L9/00 ,  C08G81/02 ,  C08C19/25

Abstract: The present invention relates to comb block copolymers, combining an elastomeric backbone and rigid pendent blocks and thus having thermoplastic elastomer properties. The invention targets in particular comb block copolymers which may be used as a material as is.According to the invention, the comb block copolymer is a diene/polypropylene thermoplastic elastomer copolymer, characterized in that it consists of a backbone, said backbone being derived from a diene elastomer, and in that it comprises from 5% to 50% by weight, relative to the total weight of the copolymer, of pendent semicrystalline polypropylene groups distributed along the backbone.Another subject of the invention is the process for preparing same, and the compositions comprising same.Finally, a subject of the invention is a tire, one of the constituent elements of which comprises such a composition.

公开(公告)号：US10266553B2

公开(公告)日：2019-04-23

申请号：US15528688

申请日：2015-12-11

Applicant: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN ,  MICHELIN RECHERCHE ET TECHNIQUE, S.A. ,  UNIVERSITE CLAUDE BERNARD LYON 1 ,  CENTRE NATIONAL DE LA RECHERCE SCIENTIFIQUE ,  CPE LYON FORMATION CONTINUE ET RECHERCHE

Inventor： Guillaume Cortial ,  Julien Thuilliez ,  Christophe Boisson ,  Franck D'Agosto ,  Sébastien Norsic

IPC: C07F7/08 ,  C08F10/02

Abstract: A compound and the use thereof to prepare a functional or telechelic polyolefin is provided. The compound has the following formula (II): Y((CH2)p—B′)m  (II), wherein m=2 or 3; Y being an alkaline earth metal or zinc when m=2, Y being aluminum when m=3; B′ being selected from the group comprising N(SiMe3)2; N(SiMe2CH2CH2SiMe2); C6F5; C3F7; C6F13; para-C6H4—NMe2; para-C6H4—O-Me; para-C6H4—N(SiMe3)2; and CH(OCH2CH2O); and p being an integer from 0 to 50.

公开(公告)号：US10189978B2

公开(公告)日：2019-01-29

申请号：US14762327

申请日：2014-01-21

Applicant: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN ,  Michelin Recherche et Technique S.A.

Inventor： Julien Thuilliez ,  Benoit Schnell ,  Julien Cladiere

IPC: C08L23/00 ,  C08L23/08 ,  B60C1/00 ,  C08L9/06 ,  C08F236/10

Abstract: The present invention relates to a rubber composition based on a reinforcing filler and on an elastomer matrix comprising a highly saturated diene elastomer comprising at least five distinct units of A, B, C, D and E distributed randomly within the elastomer at respective molar fractions of m %, n %, o %, p % and q %, where m+n+o+p+q=100; m≥50; n+o+p+q≥10; and 15≥p+q≥2.This rubber composition enables a satisfactory degree of stiffness to be reached while maintaining hysteresis properties acceptable for use in the manufacture of tires for running vehicles.