WO2010133373A1 - Agent de couplage organosilane - Google Patents

Agent de couplage organosilane Download PDF

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Publication number
WO2010133373A1
WO2010133373A1 PCT/EP2010/003117 EP2010003117W WO2010133373A1 WO 2010133373 A1 WO2010133373 A1 WO 2010133373A1 EP 2010003117 W EP2010003117 W EP 2010003117W WO 2010133373 A1 WO2010133373 A1 WO 2010133373A1
Authority
WO
WIPO (PCT)
Prior art keywords
organosilane
carbon atoms
coupling agent
formula
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2010/003117
Other languages
English (en)
French (fr)
Inventor
Karine Longchambon
José Carlos ARAUJO DA SILVA
Nicolas Seeboth
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Michelin Recherche et Technique SA Switzerland
Societe de Technologie Michelin SAS
Original Assignee
Michelin Recherche et Technique SA Switzerland
Societe de Technologie Michelin SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Michelin Recherche et Technique SA Switzerland, Societe de Technologie Michelin SAS filed Critical Michelin Recherche et Technique SA Switzerland
Priority to EP10734903.7A priority Critical patent/EP2432786B1/fr
Priority to US13/321,825 priority patent/US8987361B2/en
Priority to RU2011151971/04A priority patent/RU2575932C2/ru
Priority to CN201080021988.XA priority patent/CN102439016B/zh
Priority to JP2012511199A priority patent/JP5806659B2/ja
Publication of WO2010133373A1 publication Critical patent/WO2010133373A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage

Definitions

  • R which may be identical or different, each represent a monovalent hydrocarbon group chosen from alkyls, linear or branched, cycloalkyls or aryls, having from 1 to 18 carbon atoms;
  • R 2 represents a monovalent hydrocarbon group chosen from alkyls, linear or branched, cycloalkyls or aryls, having from 1 to 30 carbon atoms,
  • the product C (30.1 g, 0.101 mol) is obtained in a yield of 62% in the form of a white solid with a melting point of 57 ° C.
  • the molar purity estimated by 1 H and 29 Si NMR is greater than 98%.
  • the yield can be increased to 70% by additional crystallization of the mother liquors.
  • organosilane according to the invention is of particular interest from the point of view of the environment: with respect to the problem of VOC evolution mentioned in test 1 and with respect to the possibility of removing the zinc from the vulcanization system from a rubber composition without deteriorating the properties of this composition.
  • N234 (Evonik-Degussa company); (8) MES oil ("Catenex SNR" from Shell);

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/EP2010/003117 2009-05-20 2010-05-20 Agent de couplage organosilane Ceased WO2010133373A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP10734903.7A EP2432786B1 (fr) 2009-05-20 2010-05-20 Agent de couplage organosilane
US13/321,825 US8987361B2 (en) 2009-05-20 2010-05-20 Organosilane coupling agent
RU2011151971/04A RU2575932C2 (ru) 2009-05-20 2010-05-20 Органосилановое связующее
CN201080021988.XA CN102439016B (zh) 2009-05-20 2010-05-20 有机硅偶联剂
JP2012511199A JP5806659B2 (ja) 2009-05-20 2010-05-20 オルガノシランカップリング剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0902452A FR2947552B1 (fr) 2009-05-20 2009-05-20 Agent de couplage organosilane
FR0902452 2009-05-20

Publications (1)

Publication Number Publication Date
WO2010133373A1 true WO2010133373A1 (fr) 2010-11-25

Family

ID=41328474

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/003117 Ceased WO2010133373A1 (fr) 2009-05-20 2010-05-20 Agent de couplage organosilane

Country Status (7)

Country Link
US (1) US8987361B2 (enExample)
EP (1) EP2432786B1 (enExample)
JP (1) JP5806659B2 (enExample)
CN (1) CN102439016B (enExample)
FR (1) FR2947552B1 (enExample)
RU (1) RU2575932C2 (enExample)
WO (1) WO2010133373A1 (enExample)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013087698A1 (fr) * 2011-12-16 2013-06-20 Compagnie Generale Des Etablissements Michelin Agent de couplage mercaptosilane bloque
WO2018002534A1 (fr) * 2016-06-30 2018-01-04 Compagnie Generale Des Etablissements Michelin Polysulfure de monohydroxysilane

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018080754A (ja) * 2016-11-16 2018-05-24 内山工業株式会社 エンジン回りのガスケット及びその製造方法
CN110016166A (zh) * 2017-12-05 2019-07-16 东洋橡胶工业株式会社 橡胶组合物

Citations (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2094859A5 (enExample) 1970-12-10 1972-02-04 Ppg Industries Inc
FR2149339A1 (enExample) 1971-08-17 1973-03-30 Degussa
FR2206330A1 (enExample) 1972-11-13 1974-06-07 Degussa
US3873489A (en) 1971-08-17 1975-03-25 Degussa Rubber compositions containing silica and an organosilane
US3997581A (en) 1974-02-04 1976-12-14 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of sulfur containing organosilicon compounds
US4002594A (en) 1975-07-08 1977-01-11 Ppg Industries, Inc. Scorch retardants for rubber reinforced with siliceous pigment and mercapto-type coupling agent
EP0501227A1 (fr) 1991-02-25 1992-09-02 Compagnie Generale Des Etablissements Michelin-Michelin & Cie Composition de caoutchouc et enveloppes de pneumatiques à base de ladite composition
EP0680997A1 (de) 1994-05-04 1995-11-08 Bayer Ag Schwefelhaltige Organosiliciumverbindungen enthaltende Kautschukmischungen
EP0735088A1 (fr) 1995-03-29 1996-10-02 Compagnie Generale Des Etablissements Michelin-Michelin & Cie Composition de caoutchouc destinée à la fabrication d'enveloppes de pneumatiques à base de silices précipitées "dopées" à l'aluminium
EP0791622A1 (en) 1996-02-20 1997-08-27 The Goodyear Tire & Rubber Company Silica reinforced rubber composition and tire with tread thereof
EP0810258A1 (fr) 1996-05-28 1997-12-03 Compagnie Generale Des Etablissements Michelin-Michelin & Cie Composition de caoutchouc diénique à base d'alumine en tant que charge renforçante et son utilisation pour la fabrication d'enveloppes de pneumatiques
EP0881252A1 (fr) 1997-05-26 1998-12-02 Compagnie Générale des Etablissements MICHELIN-MICHELIN & CIE Composition de caoutchoc à base de silice destinée à la fabrication d'enveloppes de pneumatiques routiers ayant une résistance au roulement améliorée
WO1999002590A1 (fr) 1997-07-07 1999-01-21 Compagnie Generale Des Etablissements Michelin - Michelin & Cie Composition de caoutchouc de pneumatique couleur
WO1999002602A1 (fr) 1997-07-11 1999-01-21 Compagnie Generale Des Etablissements Michelin - Composition de caoutchouc dienique renforcee d'une charge blanche, comportant a titre d'agent de couplage (charge blanche/elastomere) un polyorganosiloxane multifonctionnalise
WO1999002601A1 (fr) 1997-07-09 1999-01-21 Compagnie Generale Des Etablissements Michelin - Michelin & Cie Composition de caoutchouc vulcanisable au soufre contenant de la silice
WO1999028376A2 (fr) 1997-11-28 1999-06-10 Compagnie Generale Des Etablissements Michelin - Michelin & Cie Charge alumineuse renforcante et composition de caoutchouc comportant une telle charge
EP0964021A2 (de) * 1998-06-10 1999-12-15 Degussa-Hüls Aktiengesellschaft Neue oligomere Organosilanpolysulfane, deren Verwendung in Kautschukmischungen und zur Herstellung von Formkörpern
WO2000005300A1 (fr) 1998-07-22 2000-02-03 Societe De Technologie Michelin Systeme de couplage (charge blanche/elastomere dienique) a base d'alkoxysilane polysulfure, d'enamine et de derive guanidique
WO2000005301A1 (fr) 1998-07-22 2000-02-03 Societe De Technologie Michelin Systeme de couplage (charge blanche/elastomere dienique) a base d'alkoxysilane polysulfure, de dithiophosphate de zinc et de derive guanidique
WO2000053671A1 (en) 1999-03-10 2000-09-14 Bridgestone/Firestone Research, Inc. Solid silica coupling agent composites in silica rubber
EP1043357A1 (de) 1999-04-03 2000-10-11 Degussa-Hüls Aktiengesellschaft Kautschukmischungen
WO2000073372A1 (fr) 1999-05-28 2000-12-07 Societe De Technologie Michelin Composition de caoutchouc pour pneumatique, a base d'elastomere dienique et d'un oxyde de titane renforçant
WO2000073373A1 (fr) 1999-05-28 2000-12-07 Societe De Technologie Michelin Composition de caoutchouc pour pneumatique, a base d'elastomere dienique et d'un oxyde de titane renforcant
DE19951281A1 (de) 1999-10-25 2001-04-26 Cebim Handelsmij B V Bauplatten auf der Grundlage von zementgebundenen Holzspanplatten sowie Verfahren zu deren Herstellung und ihre Verwendung
WO2003054075A1 (fr) * 2001-12-20 2003-07-03 Societe De Technologie Michelin Composition de caoutchouc pour pneumatique comportant un agent de couplage a fonction polythiosulfenamide
WO2003097734A1 (fr) * 2002-05-15 2003-11-27 Societe De Technologie Michelin Composition de caoutchouc pour pneumatique comportant un agent de couplage a fonction polythiobenzothiazyle

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US13A (en) * 1836-08-31 Mode of laying veneers on ogee and other moldings
ES2256317T3 (es) * 2000-10-13 2006-07-16 Societe De Technologie Michelin Organosilano polifuncional utilizable como agente de acoplamiento y su procedimiento de obtencion.
RU2267493C2 (ru) * 2004-01-15 2006-01-10 Семен Моисеевич Кавун Блокированный меркаптосилановый сшивающий агент для резиновых смесей с кремнекислотными и минеральными наполнителями
JP5501563B2 (ja) * 2004-07-29 2014-05-21 コンパニー ゼネラール デ エタブリッスマン ミシュラン 亜鉛を含まない又は実質的に含まないゴム組成物
FR2908416B1 (fr) * 2006-11-09 2009-01-16 Michelin Soc Tech Composition de caoutchouc pour pneumatique incorporant un nouveau systeme anti-oxydant
FR2940290B1 (fr) * 2008-12-22 2010-12-31 Michelin Soc Tech Agent de couplage mercaptosilane bloque
FR2940302B1 (fr) * 2008-12-22 2012-07-27 Michelin Soc Tech Composition de caoutchouc comportant un agent de couplage mercaptosilane bloque

Patent Citations (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2094859A5 (enExample) 1970-12-10 1972-02-04 Ppg Industries Inc
GB1310379A (en) 1970-12-10 1973-03-21 Ppg Industries Inc Tire tread
FR2149339A1 (enExample) 1971-08-17 1973-03-30 Degussa
US3842111A (en) 1971-08-17 1974-10-15 Degussa Sulfur containing organosilicon compounds
US3873489A (en) 1971-08-17 1975-03-25 Degussa Rubber compositions containing silica and an organosilane
FR2206330A1 (enExample) 1972-11-13 1974-06-07 Degussa
US3997581A (en) 1974-02-04 1976-12-14 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of sulfur containing organosilicon compounds
US4002594A (en) 1975-07-08 1977-01-11 Ppg Industries, Inc. Scorch retardants for rubber reinforced with siliceous pigment and mercapto-type coupling agent
EP0501227A1 (fr) 1991-02-25 1992-09-02 Compagnie Generale Des Etablissements Michelin-Michelin & Cie Composition de caoutchouc et enveloppes de pneumatiques à base de ladite composition
US5227425A (en) 1991-02-25 1993-07-13 Compagnie Generale Des Etablissements Michelin-Michelin & Cie Copolymer rubber composition with silica filler, tires having a base of said composition and method of preparing same
EP0680997A1 (de) 1994-05-04 1995-11-08 Bayer Ag Schwefelhaltige Organosiliciumverbindungen enthaltende Kautschukmischungen
US5650457A (en) 1994-05-04 1997-07-22 Bayer Ag Rubber mixtures incorporating sulphur-containing organosilicon compounds
EP0735088A1 (fr) 1995-03-29 1996-10-02 Compagnie Generale Des Etablissements Michelin-Michelin & Cie Composition de caoutchouc destinée à la fabrication d'enveloppes de pneumatiques à base de silices précipitées "dopées" à l'aluminium
US5852099A (en) 1995-03-29 1998-12-22 Compagnie Generale des Etablissements Michelin--Michelin & Cie Rubber composition for the manufacture of tires which has a base of precipitated silicas "doped" with aluminum
EP0791622A1 (en) 1996-02-20 1997-08-27 The Goodyear Tire & Rubber Company Silica reinforced rubber composition and tire with tread thereof
US5733963A (en) 1996-02-20 1998-03-31 The Goodyear Tire & Rubber Company Silica reinforced rubber composition and tire with tread thereof
EP0810258A1 (fr) 1996-05-28 1997-12-03 Compagnie Generale Des Etablissements Michelin-Michelin & Cie Composition de caoutchouc diénique à base d'alumine en tant que charge renforçante et son utilisation pour la fabrication d'enveloppes de pneumatiques
US5900449A (en) 1996-05-28 1999-05-04 Compagnie Generale Des Etablissements Michelin-Michelin & Cie Diene rubber composition based on alumina as reinforcing filler and its use for the manufacture of a tire
EP0881252A1 (fr) 1997-05-26 1998-12-02 Compagnie Générale des Etablissements MICHELIN-MICHELIN & CIE Composition de caoutchoc à base de silice destinée à la fabrication d'enveloppes de pneumatiques routiers ayant une résistance au roulement améliorée
WO1999002590A1 (fr) 1997-07-07 1999-01-21 Compagnie Generale Des Etablissements Michelin - Michelin & Cie Composition de caoutchouc de pneumatique couleur
WO1999002601A1 (fr) 1997-07-09 1999-01-21 Compagnie Generale Des Etablissements Michelin - Michelin & Cie Composition de caoutchouc vulcanisable au soufre contenant de la silice
WO1999002602A1 (fr) 1997-07-11 1999-01-21 Compagnie Generale Des Etablissements Michelin - Composition de caoutchouc dienique renforcee d'une charge blanche, comportant a titre d'agent de couplage (charge blanche/elastomere) un polyorganosiloxane multifonctionnalise
WO1999028376A2 (fr) 1997-11-28 1999-06-10 Compagnie Generale Des Etablissements Michelin - Michelin & Cie Charge alumineuse renforcante et composition de caoutchouc comportant une telle charge
EP0964021A2 (de) * 1998-06-10 1999-12-15 Degussa-Hüls Aktiengesellschaft Neue oligomere Organosilanpolysulfane, deren Verwendung in Kautschukmischungen und zur Herstellung von Formkörpern
WO2000005301A1 (fr) 1998-07-22 2000-02-03 Societe De Technologie Michelin Systeme de couplage (charge blanche/elastomere dienique) a base d'alkoxysilane polysulfure, de dithiophosphate de zinc et de derive guanidique
WO2000005300A1 (fr) 1998-07-22 2000-02-03 Societe De Technologie Michelin Systeme de couplage (charge blanche/elastomere dienique) a base d'alkoxysilane polysulfure, d'enamine et de derive guanidique
WO2000053671A1 (en) 1999-03-10 2000-09-14 Bridgestone/Firestone Research, Inc. Solid silica coupling agent composites in silica rubber
EP1043357A1 (de) 1999-04-03 2000-10-11 Degussa-Hüls Aktiengesellschaft Kautschukmischungen
WO2000073372A1 (fr) 1999-05-28 2000-12-07 Societe De Technologie Michelin Composition de caoutchouc pour pneumatique, a base d'elastomere dienique et d'un oxyde de titane renforçant
WO2000073373A1 (fr) 1999-05-28 2000-12-07 Societe De Technologie Michelin Composition de caoutchouc pour pneumatique, a base d'elastomere dienique et d'un oxyde de titane renforcant
DE19951281A1 (de) 1999-10-25 2001-04-26 Cebim Handelsmij B V Bauplatten auf der Grundlage von zementgebundenen Holzspanplatten sowie Verfahren zu deren Herstellung und ihre Verwendung
WO2003054075A1 (fr) * 2001-12-20 2003-07-03 Societe De Technologie Michelin Composition de caoutchouc pour pneumatique comportant un agent de couplage a fonction polythiosulfenamide
WO2003097734A1 (fr) * 2002-05-15 2003-11-27 Societe De Technologie Michelin Composition de caoutchouc pour pneumatique comportant un agent de couplage a fonction polythiobenzothiazyle

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE REGISTRY CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 13 June 2002 (2002-06-13), XP002558915, Database accession no. 429689-31-6 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013087698A1 (fr) * 2011-12-16 2013-06-20 Compagnie Generale Des Etablissements Michelin Agent de couplage mercaptosilane bloque
FR2984326A1 (fr) * 2011-12-16 2013-06-21 Michelin Soc Tech Agent de couplage mercaptosilane bloque
WO2018002534A1 (fr) * 2016-06-30 2018-01-04 Compagnie Generale Des Etablissements Michelin Polysulfure de monohydroxysilane
FR3053337A1 (fr) * 2016-06-30 2018-01-05 Compagnie Generale Des Etablissements Michelin Polysulfure de monohydroxysilane

Also Published As

Publication number Publication date
EP2432786A1 (fr) 2012-03-28
EP2432786B1 (fr) 2015-05-13
CN102439016A (zh) 2012-05-02
RU2011151971A (ru) 2013-07-10
JP5806659B2 (ja) 2015-11-10
RU2575932C2 (ru) 2016-02-27
FR2947552A1 (fr) 2011-01-07
CN102439016B (zh) 2015-07-22
US8987361B2 (en) 2015-03-24
FR2947552B1 (fr) 2011-08-26
JP2012527499A (ja) 2012-11-08
US20120165468A1 (en) 2012-06-28

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