EP1525259A1 - Kautschukzusammensetzung für reifen, die zyklische polysulfide-kupplungsmittel enhält - Google Patents

Kautschukzusammensetzung für reifen, die zyklische polysulfide-kupplungsmittel enhält

Info

Publication number: EP1525259A1
Authority: EP; European Patent Office
Prior art keywords: group; composition according; inorganic filler; elastomer; formula
Prior art date: 2002-07-19
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP03764971A

Other languages

English (en)

French (fr)

Inventor

Jose Carlos Araujo Da Silva

Christiane Blanchard

Gérard Mignani

Salvatore Pagano

Jean-Claude Tardivat

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.)

Compagnie Generale des Etablissements Michelin SCA

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.)

2002-07-19

Filing date

2003-07-11

Publication date

2005-04-27

2003-07-11 Application filed by Michelin Recherche et Technique SA Switzerland, Societe de Technologie Michelin SAS filed Critical Michelin Recherche et Technique SA Switzerland

2005-04-27 Publication of EP1525259A1 publication Critical patent/EP1525259A1/de

Status Withdrawn legal-status Critical Current

Links

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235000019502 Orange oil Nutrition 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000012190 activator Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
239000002318 adhesion promoter Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000005370 alkoxysilyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
230000002929 anti-fatigue Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000010692 aromatic oil Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000007767 bonding agent Substances 0.000 description 1
VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 1
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004040 coloring Methods 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
230000008094 contradictory effect Effects 0.000 description 1
230000001808 coupling effect Effects 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
125000002993 cycloalkylene group Chemical group 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000007872 degassing Methods 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001493 electron microscopy Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000446 fuel Substances 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
238000007306 functionalization reaction Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003999 initiator Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000003446 ligand Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
238000000399 optical microscopy Methods 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012766 organic filler Substances 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
150000001282 organosilanes Chemical class 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000005561 phenanthryl group Chemical group 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
230000019612 pigmentation Effects 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920003192 poly(bis maleimide) Polymers 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000000518 rheometry Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
150000004819 silanols Chemical class 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000009864 tensile test Methods 0.000 description 1
229920006027 ternary co-polymer Polymers 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
150000008111 thiosulfinates Chemical class 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/548—Silicon-containing compounds containing sulfur
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers

Definitions

a coupling agent also called a bonding agent, which has the function of ensuring the bond between the surface of the particles of inorganic filler and the elastomer, while facilitating the dispersion of this filler inorganic within the elastomeric matrix.
the BET specific surface is determined in a known manner by gas adsorption using the Brunauer-Emmett-Teller method described in "The Journal of the American Chemical Society” Vol. 60, page 309, February 1938, more precisely according to French standard NF ISO 9277 of December 1996 [multi-point volumetric method (5 points) - gas: nitrogen - degassing: hour at 160 ° C - relative pressure range p / in: 0.05 at 0.17].
the CTAB specific surface is the external surface determined according to French standard NF T 45-007 of November 1987 (method B).
organosilicon compound used as coupling agent in the compositions in accordance with the invention is that this compound can be grafted onto the elastomer by means of a sulfur group with cyclic polysulfide function, of formula:
organicsilicon (or “organosilicon”) compound must be understood, by definition, an organic compound containing at least one Carbon-Silicon bond.
Group Z preferably comprises from 1 to 18 carbon atoms, it more preferably represents an alkylene chain, a saturated cycloalkylene group, an arylene group, or a divalent group consisting of a combination of at least two of these groups. It is more preferably selected from alkylenes and Ci-Cjg arylene C 6 -C 2; it can be substituted or interrupted by one or more heteroatoms, chosen in particular from S, O and. N. Even more preferably, Z is a C ⁇ -C 8 alkylene, better a C alkylene ! -C 4 , in particular methylene, ethylene or propylene, more particularly propylene.
the cyclic polysulphide group corresponds to formula (I) in which at least one, preferably all of the following characteristics is verified:
R 4 and R 5 are both chosen from methyl, ethyl, propyl, isopropyl;
Tables 1 and 2 give the formulation of the two compositions (Table 1 - rate of the various products expressed in phr) as well as their properties before and after cooking (at the optimum cooking at 150 ° C.).
the appended figure shows the evolution of the rheometric torque (in dN.m) as a function of time (in min), for a temperature of 150 ° C., the curves denoted Cl and C2 corresponding respectively to the compositions C-1 and C-2.
the rheometric curves of the appended figure confirm the superiority of the composition according to the invention (curve C2) in terms of a share of vulcanization kinetics (see slope K of the curve of increase in torque, after 8 to 10 min of cooking), on the other hand vulcanization yield (see maximum torque, for example after 20 min of cooking).

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)

EP03764971A 2002-07-19 2003-07-11 Kautschukzusammensetzung für reifen, die zyklische polysulfide-kupplungsmittel enhält Withdrawn EP1525259A1 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR0209295		2002-07-19
FR0209295		2002-07-19
PCT/EP2003/007528 WO2004009695A1 (fr)	2002-07-19	2003-07-11	Composition de caoutchouc pour pneumatique comportant un agent de couplage a fonction polysulfure cyclique

Publications (1)

Publication Number	Publication Date
EP1525259A1 true EP1525259A1 (de)	2005-04-27

Family

ID=30470941

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP03764971A Withdrawn EP1525259A1 (de)	2002-07-19	2003-07-11	Kautschukzusammensetzung für reifen, die zyklische polysulfide-kupplungsmittel enhält

Country Status (3)

Country	Link
EP (1)	EP1525259A1 (de)
AU (1)	AU2003257451A1 (de)
WO (1)	WO2004009695A1 (de)

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Publication number	Priority date	Publication date	Assignee	Title
JP6009381B2 (ja) *	2013-03-15	2016-10-19	東洋ゴム工業株式会社	有機シラン及びその製造方法
JP6018001B2 (ja) *	2013-03-15	2016-11-02	東洋ゴム工業株式会社	ゴム組成物及び空気入りタイヤ
JP6161506B2 (ja) *	2013-10-17	2017-07-12	東洋ゴム工業株式会社	有機シラン及びそれを用いたゴム組成物
JP6377476B2 (ja) *	2014-09-25	2018-08-22	東洋ゴム工業株式会社	有機シラン及びそれを用いたゴム組成物
JP7840629B2 (ja)	2019-02-25	2026-04-06	株式会社Ｅｎｅｏｓマテリアル	含硫黄シラン化合物およびその組成物

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Publication number	Priority date	Publication date	Assignee	Title
US4100172A (en) *	1971-10-07	1978-07-11	Union Carbide Corporation	Sulfur containing norbornanyl silicon compounds
US6222055B1 (en) *	1995-07-06	2001-04-24	Fraunhofer-Gesellschaft Zur Foerderung Der Angwandten Forschung E.V.	Hydrolyzable and polymerizable and/or polyadditive silanes
US6350797B1 (en) *	1999-12-22	2002-02-26	Crompton Corporation	Use of cyclic sulfur silanes as coupling agents in sulfur-vulcanizable, silica-reinforced tire rubber compositions

2003
- 2003-07-11 AU AU2003257451A patent/AU2003257451A1/en not_active Abandoned
- 2003-07-11 EP EP03764971A patent/EP1525259A1/de not_active Withdrawn
- 2003-07-11 WO PCT/EP2003/007528 patent/WO2004009695A1/fr not_active Ceased

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004009695A1 *

Also Published As

Publication number	Publication date
AU2003257451A1 (en)	2004-02-09
WO2004009695A1 (fr)	2004-01-29

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2005-11-09	DAX	Request for extension of the european patent (deleted)
2006-12-13	RIN1	Information on inventor provided before grant (corrected)	Inventor name: MIGNANI, GERARD Inventor name: BLANCHARD, CHRISTIANE Inventor name: ARAUJO DA SILVA, JOSE, CARLOS Inventor name: TARDIVAT, JEAN-CLAUDE Inventor name: PAGANO, SALVATOREC/O MICHELIN OKAMOTO TIRE CORP.
2012-08-08	RAP1	Party data changed (applicant data changed or rights of an application transferred)	Owner name: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN Owner name: MICHELIN RECHERCHE ET TECHNIQUE S.A.
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2017-07-12	RAP1	Party data changed (applicant data changed or rights of an application transferred)	Owner name: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
2017-07-19	RAP1	Party data changed (applicant data changed or rights of an application transferred)	Owner name: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
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