WO2008074567A1 - Mélange caoutchouté et pneu - Google Patents

Mélange caoutchouté et pneu Download PDF

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Publication number
WO2008074567A1
WO2008074567A1 PCT/EP2007/062041 EP2007062041W WO2008074567A1 WO 2008074567 A1 WO2008074567 A1 WO 2008074567A1 EP 2007062041 W EP2007062041 W EP 2007062041W WO 2008074567 A1 WO2008074567 A1 WO 2008074567A1
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WO
WIPO (PCT)
Prior art keywords
rubber
weight
organosilane
content
organosilanes
Prior art date
Application number
PCT/EP2007/062041
Other languages
German (de)
English (en)
Inventor
Hajo Weinreich
Wolfgang Arenz
Original Assignee
Continental Aktiengesellschaft
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 Continental Aktiengesellschaft filed Critical Continental Aktiengesellschaft
Publication of WO2008074567A1 publication Critical patent/WO2008074567A1/fr

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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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B60C1/0016—Compositions of the tread
    • 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
    • C08L15/00—Compositions of rubber derivatives
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C08L9/06—Copolymers with styrene
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L19/00—Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00
    • C08L19/006—Rubber characterised by functional groups, e.g. telechelic diene polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L7/00—Compositions of natural rubber
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
    • Y02T10/00—Road transport of goods or passengers
    • Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
    • Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction 

Definitions

  • the invention relates to a sulfur-crosslinkable rubber compound, in particular for the tread of two-wheeled pneumatic tires, comprising at least one diene rubber, at least one polar filler and at least one silane coupling tang.
  • the invention further relates to a pneumatic vehicle tire, in particular a two-wheeled tire, having a tread which consists at least in part of such a sulfur-vulcanized rubber mixture.
  • the rolling resistance In order to influence the rolling resistance, it is known to vary the degree of filling, the type of filler, the crosslinking system and / or the glass transition temperature of the rubber. To influence tire properties such as abrasion, wet skid and rolling resistance, it is z. For example, it is known to use various styrene-butadiene copolymers with different styrene and vinyl contents and with different modifications for the rubber blends. It is known from EP 1 270 657 A1 to improve the properties of a tire with regard to wet grip, winter properties, abrasion and rolling resistance by using 30 to 90 phr of a solution-polymerized styrene-butadiene copolymer for the rubber mixture which forms the tire tread strip.
  • S-SBR having a styrene content of 5 to 35% by weight and a vinyl content of 10 to 85% by weight.
  • the S-SBR is coupled, for example with tin, and is chemically modified with an amino group.
  • the rubber composition also contains 10 to 70 phr of at least one other diene rubber, 20 to 100 phr of silica, 1 to 15 phr of silane coupling agent and 5 to 60 phr of a specific plasticizer.
  • EP 1 457 501 A1 discloses styrene-butadiene copolymers having a high vinyl content modified with primary amino groups and alkoxysilyl groups, processes for preparing these styrene-butadiene copolymers, rubber mixtures with these styrene-butadiene copolymers and tires whose Treads consist of this rubber mixture.
  • the tires should be characterized by a good balance between abrasion resistance, durability, hysteresis loss and wet grip behavior.
  • EP 1 153 972 A1 describes rubber compounds for tire treads which comprise styrene-butadiene copolymers having coupling centers with epoxide groups, optionally further diene rubbers, processing oil, silica and vulcanizing agent.
  • the coupling centers are within the polymer backbone and not as end groups.
  • the rubber compounds show good processability and should cause a low rolling resistance with good wet grip when tires.
  • Polar fillers such as silica, silicates or aluminosilicates have on their surface polar groups, eg. For example, OH groups, and have been used for many years in rubber blends to improve the properties of rubber blends.
  • silane Coupling agents used in rubber compounds.
  • the silane coupling agents react with the superficial silanol groups of the silica or other polar groups during the mixing of the rubber or the rubber mixture (in situ) or even before the addition of the filler to the rubber in the sense of a pretreatment (pre-modification).
  • the silane coupling agents used are bifunctional organosilanes which have at least one alkoxy, cycloalkoxy or phenoxy group as leaving group on the silicon atom and which have a vulcanization-reactive group as other functionality which, if appropriate, can undergo a chemical reaction with the double bonds of the polymer after cleavage.
  • silane coupling agents z may be 3-mercaptopropyltriethoxysilane, 3-thiocyanato-propyltrimethoxysilane or 3,3'-bis (triethoxysilylpropyl) polysulfanes having 2 to 8 sulfur atoms, such as. B. 3,3'-bis (triethoxysilylpropyl) tetrasulfan (TESPT), the corresponding disulfane (TESPD) or mixtures of the AnIf anen having 1 to 8 sulfur atoms with different
  • silane coupling agents Used in the various sulfanes, are used in the tire industry almost exclusively silane coupling agents with sulfur chains. As a dosage of the silane coupling agents, the manufacturers recommend amounts of 1 to a maximum of 10 phf (parts per hundred parts of filament by weight), since then an optimal binding of the filler to the rubber (s) can take place.
  • the invention is based on the object of providing rubber mixtures for the treads of pneumatic vehicle tires, in particular two-wheeled tires, which cause a reduced rolling resistance and a reduced abrasion while maintaining a good wet behavior during the tire.
  • organosilanes as vulcanization reactive functional group having a sulfur chain with 2 to 8 sulfur atoms and the first organosilane a content of S 2 - organosilanes of at least 80 mol% and the second organosilane mixture one
  • phr parts per hundred parts of rubber by weight
  • the dosage of the parts by weight of the individual substances is always based on 100 parts by weight of the total mass of all the rubbers present in the mixture.
  • phf parts per hundred parts of filament by weight
  • the dosage of the parts by weight of the individual substances is based on 100 parts by weight of the mass of polar filler, in particular silica, with which the silane coupling agent interacts.
  • a diene rubber with functionalizations that can chemically or electrostatically interact with polar fillers different rubbers with For example, be modified amino, alkoxysilyl and / or epoxy groups.
  • rubber types come z.
  • natural rubber synthetic polyisoprene, polybutadiene and styrene-butadiene copolymers into consideration, which can also be coupled, for example with tin, can be used.
  • Various functionalized diene rubbers can also be used in the blend.
  • the diene rubber with the functionalizations is a solution-polymerized styrene-butadiene copolymer which is modified with primary amino groups, alkoxysilyl groups and / or epoxide groups.
  • solution-polymerized styrene-butadiene copolymers for example, so-called HPR types from JSR Corporation, the preparation of which is disclosed, for example, in EP 1 457 501 A1, or NS 116 R from Nippon Zeon (see, for example, US Pat. No. 4,616,069) can be used ,
  • the solution-polymerized styrene-butadiene copolymer preferably has a vinyl content of 35-80% by weight and a styrene content of 10-35% by weight.
  • the amino groups and with alkoxysilyl groups functionalized solution polymerized styrene-butadiene copolymers HPR 355 (Tg: -27 0 C, 28 wt .-% styrene, 56 wt .-% vinyl) can and HPR (350 Tg: -35 0 C, 21% by weight of styrene, 55% by weight of vinyl) from JSR Corporation.
  • the rubber mixture preferably contains silica in amounts of from 40 to 110 phr.
  • silica content is concerned, in the context of the present invention it is possible in principle to use any finely divided precipitated silica which is conventionally used for the preparation of rubber mixtures.
  • such silicas are used as a filler having a BET surface area (according to ASTM D 5604) of 35 to 350 m 2 / g, preferably from 145 to 270 m 2 / g, a CTAB surface (according to ASTM D 3765) of 30 to 350 m 2 / g, preferably from 120 to 285 m 2 / g, a pore volume (according to DIN 66133) of 0.2 to 3.4 mL / g, preferably from 0.7 to 1.7 mL / g and a DBP number (according to ASTM D 2414) of 50 to 300 mL / 100 g, preferably from 150 to 250 mL / 100 g.
  • BET surface area accordinging to ASTM D 5604
  • CTAB surface accordinging to ASTM D 3765
  • a pore volume accordinging to DIN 66133
  • a DBP number accordinging to ASTM D 2414
  • silicas can thus z.
  • B those of the type VN3 (trade name) of the company Degussa as well as highly dispersed silicic acids, so-called HD silicas, (eg Ultrasil 7000 from Degussa) are used.
  • the rubber mixture according to the invention contains a total of 4-12 phf, preferably 6-10 phf, at least two organosilane mixtures as silane coupling agents, wherein the organosilanes as Vulcanisationsreoxide functional group having a sulfur chain with 2 to 8 sulfur atoms and the first organosilane a content of S 2 - Organosilanes of at least 80 mol% and the second organosilane mixture has a content of S 2 -organosilanes of less than 20 mol% and a content of S 4 -organosilanes of at least 50 mol%.
  • the first and second organosilane mixtures are used in a ratio of 0.25: 1 to 10: 1, preferably 1: 1 to 5: 1.
  • the S 2 and S 4 organosilanes may have different organic radicals, such as 3-trimethoxysilylpropyl or 3-trimethoxysilylhexyl radicals. However, it is preferred if the S 2 organosilane is bis (3-triethoxysilylpropyl) disulfane and the S 4 organosilane is bis (3-triethoxysilylpropyl) tetrasulfan.
  • a second organosilane mixture having a content of S 2 -organosilanes of less than 20 mol% and a content of S 4 -organosilanes of at least 50 mol% z.
  • Si-69 or X50S silanes on carbon black N-330, 50:50 from Degussa be used.
  • the rubber composition may also contain other non-functionalized or otherwise functionalized rubbers in amounts up to 75 phr.
  • These rubbers may be selected from the group consisting of natural rubber (NR), synthetic polyisoprene (IR), polybutadiene (BR), styrene Butadiene copolymers (SBR), styrene-isoprene-butadiene terpolymer, butyl rubber, halobutyl rubber or ethylene-propylene-diene rubber (EPDM).
  • NR natural rubber
  • IR synthetic polyisoprene
  • BR polybutadiene
  • SBR styrene Butadiene copolymers
  • EPDM ethylene-propylene-diene rubber
  • the rubber mixture as further rubbers at least one diene rubber selected from the group consisting of
  • Natural rubber synthetic polyisoprene, polybutadiene and styrene-butadiene copolymers. These diene rubbers work well with the rubber compound and provide good tire properties in the cured tires.
  • the rubber mixture may contain polyisoprene (IR, NR) as the diene rubber.
  • polyisoprene IR, NR
  • IR, NR polyisoprene
  • These may be both cis-1,4-polyisoprene and 3,4-polyisoprene.
  • preference is given to the use of cis-1,4-polyisoprenes having a cis-1,4-content of> 90% by weight.
  • such a polyisoprene can be obtained by stereospecific polymerization in solution with Ziegler-Natta catalysts or using finely divided lithium alkyls.
  • natural rubber (NR) is one such 1,4-polyisoprene; the cis-1,4-content in natural rubber is greater than 99% by weight.
  • the rubber mixture contains polybutadiene (BR) as the diene rubber, these may be both 1,4-vinyl and vinyl polybutadiene (40-90% by weight vinyl content).
  • BR polybutadiene
  • these may be both 1,4-vinyl and vinyl polybutadiene (40-90% by weight vinyl content).
  • the other styrene-butadiene copolymers are those which do not fall under the specially modified solution-polymerized types of claim 1. It can be z. B. not or otherwise modified or coupled solution-polymerized styrene-butadiene copolymers act. However, it is also possible to use emulsion-polymerized styrene-butadiene copolymers (E-SBR) and also mixtures of E-SBR and S-SBR.
  • E-SBR emulsion-polymerized styrene-butadiene copolymers
  • the styrene content of the E-SBR is about 15 to 50 wt .-% and it can from The prior art types obtained by copolymerization of styrene and 1,3-butadiene in aqueous emulsion can be used.
  • the rubber mixture contains, as plasticizer, 5 to 30 phr of at least one liquid polybutadiene having a molecular weight of 1500-10,000 g / mol and a vinyl content of 15-50 wt .-% contains.
  • the rubber mixture can be further customary in the rubber industry additives such.
  • carbon blacks short fibers, rubber gels, other plasticizers, aging inhibitors, activators, such as.
  • zinc oxide and fatty acids eg., Stearic acid
  • waxes and Mastikationstosstoff in usual parts by weight.
  • the vulcanization is carried out in the presence of sulfur or sulfur donors, with some sulfur donors can also act as a vulcanization accelerator.
  • Sulfur or sulfur donors are added in the last mixing step in the amounts customary by the person skilled in the art (0.4 to 4 phr, sulfur, preferably in amounts of 1.5 to 2.5 phr) of the rubber mixture.
  • the rubber composition may contain vulcanization-affecting substances such as vulcanization accelerators, vulcanization retarders and vulcanization activators in conventional amounts in order to control the time and / or the required temperature of the vulcanization and to improve the vulcanizate properties.
  • the vulcanization accelerators may be selected, for example, from the following groups of accelerators: thiazole accelerators such as. B. 2-mercaptobenzothiazole, sulfenamide accelerators such as. B. benzothiazyl-2-cyclohexylsulfenamid (CBS), guanidine accelerators such as. N, N'-diphenylguanidine (DPG), dithiocarbamate accelerators such as.
  • the accelerators can also be used in combination with each other, which can result in synergistic effects.
  • the preparation of the rubber mixture according to the invention is carried out in a conventional manner, in which case a base mixture which contains all constituents except the vulcanization system (sulfur and vulcanization-influencing substances) is first prepared in one or more mixing stages and subsequently by addition of the vulcanization system Ready mix is produced. Subsequently, the mixture is further processed, for. B. brought by an extrusion process, and in the appropriate form. Preferably, the mixture is brought into the form of a tread.
  • a tread blending blank produced in this way is laid down in the production of the vehicle pneumatic tire blank, in particular a two-wheeled tire blank, as is known. It is irrelevant in the tires whether the entire tread has been made from a single mixture or z.
  • B. has a cap and base structure, because it is important that at least the coming into contact with the road surface of the rubber composition according to the invention has been prepared.
  • the comparative mixtures are marked with V, the mixtures according to the invention are marked with E.
  • the mixtures 1 to 6 differ only in the type and optionally amount of the following substances: solution-polymerized styrene-butadiene copolymer, plasticizer and silane coupling agents.
  • solution-polymerized styrene-butadiene copolymer plasticizer and silane coupling agents.
  • accelerator and sulfur were increased to keep the crosslink density in the polymer matrix constant.
  • test specimen preparation was carried out under standard conditions in two stages in a laboratory tangential mixer. From all mixtures test specimens were prepared by vulcanization for 20 minutes under pressure at 160 0 C and determined with these specimens for the rubber industry typical material properties listed in Table 2. The following test methods were used for the tests on test specimens: Tensile strength at room temperature in accordance with DIN 53 504
  • Abrasion according to DIN 53516 The abrasion of the mixture 1 was set equal to 100, values greater than 100 mean an improvement of the abrasion, equivalent to a reduction of the DIN abrasion volume.
  • Table 2 shows that abrasion performance and rolling resistance can be further improved by using a liquid polybutadiene as a plasticizer instead of an aromatic processing oil.

Abstract

L'invention concerne un mélange caoutchouté vulcanisable avec du soufre, notamment pour la bande de roulement de pneus pour deux roues, contenant, pour obtenir de faibles frottements au roulement, une faible abrasion et un bon comportement à l'humidité, - 25 phr (parties en poids, par rapport à 100 parties en poids du caoutchouc total dans le mélange) d'au moins un caoutchouc diène comportant des fonctionnalités pouvant interagir chimiquement ou électrostatiquement avec des matières de remplissage polaires, - > 7,5 phr d'au moins une matière de remplissage polaire et - 4 à 12 phf (parties en poids par rapport à 100 parties en poids de la matière de remplissage polaire) d'au moins deux mélanges organosilanes en tant qu'agents de couplage silane. Selon l'invention, lesdits organosilanes, en tant que groupements fonctionnels réagissant par vulcanisation, présentent une chaîne soufrée comportant de 2 à 8 atomes de soufre et le premier mélange organosilane a une teneur en organosilane S2 supérieure ou égale à 80 % en moles et le second mélange organosilane a une teneur en organosilanes S2 inférieure à 20 % en moles et une teneur en organosilanes S4 supérieure ou égale à 50 % en moles.
PCT/EP2007/062041 2006-12-16 2007-11-08 Mélange caoutchouté et pneu WO2008074567A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006059530.0 2006-12-16
DE102006059530A DE102006059530A1 (de) 2006-12-16 2006-12-16 Kautschukmischung und Reifen

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WO2008074567A1 true WO2008074567A1 (fr) 2008-06-26

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8067491B2 (en) 2006-12-28 2011-11-29 Momentive Performance Materials Inc. Silated cyclic core polysulfides, their preparation and use in filled elastomer compositions
US8188174B2 (en) 2006-12-28 2012-05-29 Momentive Performance Materials Inc. Silated core polysulfides, their preparation and use in filled elastomer compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0447066A1 (fr) * 1990-03-02 1991-09-18 Bridgestone Corporation Pneumatiques
EP0819694A2 (fr) * 1996-07-18 1998-01-21 Degussa Aktiengesellschaft Compositions de organopolysulfanes et procédé de préparation de compositions de caoutchouc les contenant
EP1270657A1 (fr) * 2001-06-29 2003-01-02 Continental Aktiengesellschaft Composition de caoutchouc pour bande de roulement d'un pneu
EP1484359A1 (fr) * 2003-06-03 2004-12-08 Sumitomo Rubber Industries Limited Composition de caoutchouc pour bandes de roulement et pneu pneumatique à base de ladite

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0447066A1 (fr) * 1990-03-02 1991-09-18 Bridgestone Corporation Pneumatiques
EP0819694A2 (fr) * 1996-07-18 1998-01-21 Degussa Aktiengesellschaft Compositions de organopolysulfanes et procédé de préparation de compositions de caoutchouc les contenant
EP1270657A1 (fr) * 2001-06-29 2003-01-02 Continental Aktiengesellschaft Composition de caoutchouc pour bande de roulement d'un pneu
EP1484359A1 (fr) * 2003-06-03 2004-12-08 Sumitomo Rubber Industries Limited Composition de caoutchouc pour bandes de roulement et pneu pneumatique à base de ladite

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8067491B2 (en) 2006-12-28 2011-11-29 Momentive Performance Materials Inc. Silated cyclic core polysulfides, their preparation and use in filled elastomer compositions
US8188174B2 (en) 2006-12-28 2012-05-29 Momentive Performance Materials Inc. Silated core polysulfides, their preparation and use in filled elastomer compositions
US8501849B2 (en) 2006-12-28 2013-08-06 Momentive Performance Materials Inc. Silated core polysulfides, their preparation and use in filled elastomer compositions

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