WO2015043902A1 - Schwefelvernetzbare kautschukmischung - Google Patents
Schwefelvernetzbare kautschukmischung Download PDFInfo
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- WO2015043902A1 WO2015043902A1 PCT/EP2014/068786 EP2014068786W WO2015043902A1 WO 2015043902 A1 WO2015043902 A1 WO 2015043902A1 EP 2014068786 W EP2014068786 W EP 2014068786W WO 2015043902 A1 WO2015043902 A1 WO 2015043902A1
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- WIPO (PCT)
- Prior art keywords
- rubber
- phr
- groups
- styrene
- functionalized
- Prior art date
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Classifications
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B7/00—Mixing; Kneading
- B29B7/74—Mixing; Kneading using other mixers or combinations of mixers, e.g. of dissimilar mixers ; Plant
- B29B7/7476—Systems, i.e. flow charts or diagrams; Plants
- B29B7/7495—Systems, i.e. flow charts or diagrams; Plants for mixing rubber
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- 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
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- 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
- B60C1/0025—Compositions of the sidewalls
-
- 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
- B60C11/00—Tyre tread bands; Tread patterns; Anti-skid inserts
- B60C11/0008—Tyre tread bands; Tread patterns; Anti-skid inserts characterised by the tread rubber
-
- 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
- B60C13/00—Tyre sidewalls; Protecting, decorating, marking, or the like, thereof
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- 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
-
- 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 vehicle tires, straps, belts and hoses.
- the rubber composition of the tread highly determines the
- the focus here is mainly on the properties of rolling resistance and Abrasion.
- Tire property often brings with it a deterioration of another property.
- Tire property often brings with it a deterioration of another property.
- vehicle tires are understood in the present document pneumatic vehicle tires, solid rubber tires and two-wheeled tires.
- Rubber compound by the choice of suitable polymer systems is widely discussed in the art.
- Glass transition temperature of the polymer used / the polymers used is determined. The higher the glass transition temperature of a polymer, the higher the glass transition temperature of the rubber compound and the worse it is
- Roll resistance behavior of rubber compounds is the rebound resilience at 60 to 70 ° C and the values for the hysteresis loss expressed by the tan ⁇ at 60 to 70 ° C.
- 1,4-polybutadiene rubber has a very low glass transition temperature of about -105 ° C, which makes it
- Rubber is suitable for improving the rolling resistance behavior of rubber compounds.
- wet grip behavior of the rubber compounds is also known that the wet grip behavior of the rubber compounds.
- Rubber composition is significantly deteriorated.
- styrene-butadiene copolymers having different styrene and vinyl contents and with different modifications for the rubber mixtures, whereby here too the described
- Diene rubber here specifically natural rubber, and 80 to 20 phr styrene butadiene
- Copolymer having a glass transition temperature between -50 ° C and -25 ° C used.
- the use of 10 to 50 phr diene rubber, here styrene-butadiene rubber, with a glass transition temperature less than -45 ° C to improve the ratio of dry and wet grip is described in EP 1253170 AI.
- US 6,812,822 B2 turn 5 to 40 phr styrene-butadiene copolymer with a
- Rubber with a glass transition temperature of -20 ° C or less used to improve the damping properties ("vibration-insulating properties") of the rubber mixture.
- DE 40 01 822 C2 describes a rubber composition comprising 10 to 100
- a solution-polymerized styrene-butadiene rubber having a vinyl content of 20 to 70 parts by weight and a styrene content of 54.5 to 65 parts by weight and 0 to 90 parts by weight of an emulsion-polymerized styrene-butadiene rubber having a glass transition point of at least -60 ° C and a styrene content of 20 to 65 parts by weight and at least 70 parts by weight of carbon black, which are mixed into this rubber composition.
- This rubber composition is intended for use on treads of high performance tires with high hysteresis loss, high thermal resistance and remarkable grip.
- This mixture shows improved laboratory properties, which with improved
- EP 2357211 A1 discloses a rubber mixture which comprises at least one aliphatic and / or aromatic hydrocarbon resin, at least one filler and at least one functionalized diene rubber whose functionalization is present along the polymer chain and / or at the end and one
- hydroxy groups are disclosed in Table 1 for attachment of the polymers to silica.
- EP 2289990 AI discloses a rubber composition, the same amounts of
- Silica and carbon black, as well as functionalized polymers disclosing inter alia the use of 50 phr of siloxy- or siloxy-aldimine functionalized polybutadiene instead of 50 phr of an unfunctionalized polybutadiene.
- Such a rubber compound shows improved rolling resistance indicators (rebound 100 ° C) while the wet grip properties deteriorate (rebound 23 ° C).
- the influence on the tearing properties, in particular the tearing properties, are not disclosed in EP 2289990 A1.
- Functionalization carries polyorganosiloxane groups containing epoxy groups, wherein three or more polymer chains are attached to a polyorganosiloxane group.
- This polymer with an unfunctionalized butadiene rubber in a siliceous rubber compound results in improved rolling resistance, abrasion and wet grip properties.
- the invention is therefore based on the prior art based on the object to provide a rubber compound, especially for vehicle tires, straps, belts and hoses, which behave by a further improvement in rolling resistance and characterized in abrasion behavior, the other physical Properties remain at the same level or in particular the tearing properties and / or the wet grip properties are also further optimized.
- the should be based on the prior art based on the object to provide a rubber compound, especially for vehicle tires, straps, belts and hoses, which behave by a further improvement in rolling resistance and characterized in abrasion behavior, the other physical Properties remain at the same level or in particular the tearing properties and / or the wet grip properties are also further optimized.
- Rubber composition optionally have an improvement in winter properties and / or handling behavior.
- T g glass transition temperature
- the remaining tire properties remain at an approximately equal level or even improved, in particular the wet grip and / or the tear properties and / or the dry braking behavior and / or the
- phr parts per hundred parts of rubber by weight
- the dosage of the parts by weight of the individual substances is referred to in this document to 100 parts by weight of the total mass of all high molecular weight and thus solid rubbers present in the mixture.
- Rubber with a high T g was used to increase the glass transition temperature of the
- These rubbers can, according to the present invention, be stabilized by at least one styrene-butadiene rubber functionalized with phthalocyanine groups and / or hydroxyl groups and / or epoxy groups and / or silane-sulfide groups and having a glass transition temperature (T g ) in the range between -120 ° C and -75 ° C are replaced, which surprisingly also shows a significant improvement in the abrasion behavior.
- T g glass transition temperature
- the T g of the styrene-butadiene rubber functionalized with phthalocyanine groups and / or hydroxyl groups and / or epoxy groups and / or silane-sulfide groups is generally lower than that of the previously used functionalized styrene-butadiene rubbers.
- the proportion of styrene-butadiene rubbers having a higher T g can be further increased, in order to further exploit the advantages of the so-called "high-T g -styrene-butadiene rubber". that of the functionalized styrene-butadiene rubber used in the rubber mixture with phthalocyanine groups and / or hydroxyl groups and / or epoxy groups and / or silane-sulfide groups
- Functionalized with phthalocyanine groups and / or hydroxyl groups and / or epoxy groups and / or silane-sulfide groups in the context of the present application means that the rubber along the polymer chain at least one of these groups and / or at the chain end of each polymer chain at least a phthalocyanine group and / or hydroxyl group and / or epoxy group and / or silane-sulfide group carries. It is also conceivable that not all polymer chains have a phthalocyanine group and / or hydroxyl group and / or epoxy group and / or silane-sulfide group.
- the weight fraction of functionalized polymer chains is preferably from 30 to 100% by weight, more preferably from 50 to 100% by weight, and very preferably from 70 to 100% by weight.
- the polymer chains are preferably at their chain end with at least one
- Phthalocyanine group and / or hydroxyl group and / or epoxy group and / or silane-sulfide group functionalized Phthalocyanine group and / or hydroxyl group and / or epoxy group and / or silane-sulfide group functionalized.
- the functionalized styrene-butadiene rubber is preferably anionic
- the living anionic polymer chains react with one or more modifier compounds, thereby attaching the functional group (s).
- the functionalized styrene-butadiene rubber is functionalized with at least one hydroxy group and / or at least one silane-sulfide group.
- silane sulfide group is under the present invention.
- the present invention refers to an organic radical containing at least one sulfur atom and at least one substituted silyl group -SiR 3 .
- silane-sulfide groups contain one or more sulfur atom (s).
- styrene-butadiene rubber functionalized with at least one silane-sulfide group over a functionalized styrene-butadiene rubber containing siloxy, -siloxane, siloxy-aldimine or aminosiloxane groups, but which are sulfur-free, ie contain no sulfur atoms, are functionalized, improved physical properties are achieved, in particular improved rolling resistance indicators and / or improved abrasion behavior and / or improved tear properties and / or improved handling predictors, such as
- radicals R are independently of one another Ci-Ci 6 alkyl or benzyl groups; and R "is a C 1 -C 4 alkyl group;
- R ' is selected from C 6 -C 18 aryl, C 7 -C 50 alkylaryl, Ci-C 50 alkyl and C 2 -C 50 dialkyl ethers (ie, -alkyl-O-alkyl), wherein each group is optionally substituted with one or more groups, which is / are selected from the group consisting of Ci-C4-alkyl, Ci- C 4 alkoxy, C 6 -C 12 aryl, C 7 -C 16 alkylaryl, di ( Ci-C 7 hydrocarbyl) amino, bis (tri (Ci-Ci 2 - alkyl) silyl) amino, tris (Ci-C 7 hydrocarbyl) silyl, and -C 12 thioalkyl; and
- x is an integer selected from the numbers 1, 2 and 3;
- x is an integer selected from the numbers 0, 1 and 2;
- y is an integer selected from the numbers 0, 1 and 2;
- z is an integer selected from the numbers 1, 2 and 3;
- Such a functionalized styrene-butadiene rubber is recognizably functionalized with silane-sulfide groups as in formula II).
- x is an integer selected from the numbers 0, 1 and 2;
- y is an integer selected from the numbers 0, 1 and 2;
- z is an integer selected from the numbers 1, 2 and 3;
- each R is independently selected from C 1 -C 8 -alkyl groups and R 'is a C 1 -C 5 -alkyl group. According to another preferred embodiment of the invention is the
- R 2 , R 3 , R 10 , R 11 , R 12 , R 14 , R 16 , R 17 and R 18 are independently selected from Ci-Ci 6 alkyl and -Benzyl groups, and wherein the alkyl groups R 10 , R 11 and R 12 and R 16 , R 17 and R 18 may be bonded to each other in the form of a ring containing two silicon atoms and nitrogen (N); and
- R 1 and R 13 are independently selected from C 1 -C 4 alkyl groups
- R 4, R 9 and R 15 are independently selected from C ö -C 8 -aryl, C 7 -C50-
- each group is optionally substituted with one or more groups, which is / are selected from the group consisting of Ci-C4-alkyl, Ci-C 4 alkoxy, C 6 -C 2 - aryl, C 7 -C 6 - Alkylaryl, di (C 1 -C 7 -hydrocarbyl) amino, bis (tri (C 1 -C 12 -alkyl) silyl) amino, tris (C 1 -C 7 -hydrocarbyl) silyl and C 1 -C 12 -thioalkyl; and
- R 5 , R 6 and R 7 are independently selected from hydrogen (-H), C 1 -C 16 -alkyl and C 6 -C 2 -aryl;
- R is selected from Ci-C 6 alkyl and C 2 -C ö aryl
- R 19, R 20 and R 21 are independently selected from hydrogen and C 1 -C 16 alkyl
- x and p are each an integer selected from the numbers 1 and 2; and y and q are each an integer selected from the numbers 1 and 2; and
- the compound according to formula IV is an example of the silane-sulfide modifier according to formula (3).
- the functionalized styrene-butadiene rubber is formed by reaction of the living polymer chains in the anionic polymerization with a silane-sulfide modifier according to formula IV) and formula V):
- the compound according to formula V) is an example of the silane-sulfide modifier according to formula (1).
- the above-mentioned solution-polymerized styrene-butadiene rubber in the unvulcanized state has a glass transition temperature of -75 ° C to -120 ° C (minus 75 to minus 120 ° C), preferably -75 to -110 ° C, particularly preferably -80 to -110 ° C, most preferably -80 ° C to -100 ° C, and thus can be regarded as styrene-butadiene rubber having a comparatively low glass transition temperature.
- the functionalized styrene-butadiene rubber used in the rubber mixture has a styrene content of 0 to 12% by weight. This means that at 0% by weight of styrene a butadiene rubber is present.
- the styrene content of the styrene-butadiene rubber is 0 to 2% by weight, particularly preferably 0% by weight. According to a further preferred embodiment of the invention, the styrene content of the styrene-butadiene rubber is 0.1 to 12% by weight, particularly preferably 5 to 12% by weight, very particularly preferably 9 to 11% by weight.
- the solution-polymerized styrene-butadiene rubber preferably has a vinyl content, based on the butadiene content, of 1 to 30% by weight, preferably 1 to 15% by weight, particularly preferably 5 to 12% by weight and very particularly preferably 7 to 12 Gew.-, again very particularly preferably from 7 to 11 Gew.-. on. This achieves a low glass transition temperature of the polymer.
- the polymers discussed in the context of the present invention are synthesized by means of 13 C-NMR (deuterochloroform CDC1 3 solvent, nuclear magnetic resonance) and comparison with data from infrared spectrometry (IR; FT-IR spectrometer from Nicolet, KB r - Window 25 mm diameter x 5 mm, 80 mg sample in 5 mL 1,2-dichlorobenzene) The determination of the glass transition temperature (T g ) of the polymers
- the preferred molecular weight distribution of the functionalized styrene-butadiene rubber, Mw / Mn, is between 1.2 and 3.0.
- Mw / Mn is less than 1.2, poor processability of the polymer and the rubber composition of the present invention and poor distribution of the ingredients, especially poor filler dispersion of the rubber composition, result.
- Mw / Mn is greater than 3.0, the content of low molecular weight components is too high, resulting in increased hysteresis and hence poor rolling resistance of the rubber composition.
- the above functionalized styrene-butadiene rubber is in the rubber mixture of the invention in amounts of 5 to 95 phr, preferably 20 to 95 phr, more preferably 40 to 95, particularly preferably 60 to 95 phr, again very particularly preferably in amounts of 70 to 90 used phr.
- the used with phthalocyanine groups and / or hydroxyl groups and / or epoxy groups and / or silane-sulfide groups functionalized styrene-butadiene rubber in a preferred embodiment has a styrene content of 0 wt and a
- Vinyl content of 1 to 15% by weight, particularly preferably 7 to 12% by weight.
- the styrene-butadiene rubber functionalized with phthalocyanine groups and / or hydroxyl groups and / or epoxy groups and / or silane-sulfide groups may be solution-polymerized or emulsion-polymerized. Preference is given to solution-polymerized styrene-butadiene rubber S (S) BR having a styrene content of 0 to 12% by weight.
- S (S) BR solution-polymerized styrene-butadiene rubber
- S (S) BR having a styrene content of 0 to 12% by weight.
- the fiction, contemporary rubber mixture also contains 5 to 95 phr, preferably 5 to 80 phr, more preferably 5 to 60 phr, most preferably 5 to 40 phr, again very particularly preferably 10 to 30 phr of at least one other rubber.
- the at least one further rubber is selected from the group consisting of natural polyisoprene and / or synthetic polyisoprene and / or butadiene rubber and / or solution-polymerized styrene-butadiene rubber and / or emulsion-polymerized styrene-butadiene rubber and / or liquid rubbers a molecular weight Mw of greater than 20,000 g / mol and / or halobutyl rubber and / or polynorbornene and / or isoprene-isobutylene copolymer and / or ethylene-propylene-diene rubber and / or nitrile rubber and / or chloroprene rubber and / or acrylate rubber and / or fluororubber and / or silicone rubber and / or polysulfide rubber and / or epichlorohydrin rubber and / or styrene-isoprene-butadiene ter
- nitrile rubber hydrogenated acrylonitrile-butadiene rubber
- Chloroprene rubber, butyl rubber, halobutyl rubber or ethylene-propylene-diene rubber are used in the manufacture of technical rubber articles such as belts, straps and hoses.
- the further rubber is at least one
- Diene rubber selected from the group consisting of synthetic rubber
- the natural polyisoprene and the synthetic polyisoprene may be all types known to those skilled in the art.
- the further diene rubber is preferably at least natural polyisoprene.
- a particularly good processability (extrudability, miscibility, etc.) of the rubber mixture according to the invention is achieved.
- the styrene-butadiene rubber from the group of other diene rubbers is within the scope of present application, a known in the art styrene-butadiene rubber and can therefore be present in the blend with the essential to the invention
- solution-polymerized styrene-butadiene rubber which is functionalized with phthalocyanine groups and / or hydroxyl groups and / or epoxy groups and / or silane-sulfide groups and whose styrene content is 0 to 12% by weight and which in the unvulcanized state has a glass transition temperature T g according to DSC of -75 to -120 ° C, can be used.
- Rubber mixture 5 to 95 phr of at least one natural polyisoprene and / or 5 to 95 phr of at least one synthetic polyisoprene, preferably 5 to 20 phr of at least one natural polyisoprene and / or 5 to 20 phr of at least one synthetic polyisoprene.
- the rubber mixture contains from 5 to 15 phr of at least one natural and / or synthetic polyisoprene in
- Embodiment particularly preferably a styrene content of 0 to 2 parts by weight, most preferably of 0 wt., Has.
- a rubber composition in comparison to a rubber composition containing the same amount of butadiene rubber having a Tg of -105 ° C of the prior art, improved abrasion resistance and improved rolling resistance performance, where the other tire performances are not significantly deteriorated and / or stay the same.
- wet grip behavior and tearing properties remain at a level for use in
- Rubber composition shows improved abrasion properties, improved rolling resistance behavior and an equal and / or increased rigidity as an indicator of constant and compared to a rubber mixture containing the same amount of butadiene rubber with a T g of -105 ° C from the prior art / or improved handling behavior wherein the remaining tire properties are not significantly degraded and / or remain the same.
- wet grip behavior and tear properties remain on one for use in treads
- the rubber composition has improved rolling resistance and wet braking and attrition and dry braking properties as compared to the prior art.
- the rubber mixture contains 30 to 50 phr of the above-described functionalized styrene-butadiene rubber having a T g of -100 to -87 ° C, which in this embodiment particularly preferably a styrene content of 0 to 2% by weight, most preferably from 0% by weight, and from 5 to 10 phr of natural polyisoprene and from 40 to 60 phr of at least one further styrene-butadiene rubbers.
- a rubber composition has particularly advantageous abrasion and wet grip properties, without showing disadvantages in terms of rolling resistance.
- the above-described functionalized styrene-butadiene rubber having a T g of -100 to -87 ° C, which in this embodiment particularly preferably a styrene content of 0 to 2% by weight, most preferably from 0% by weight, and from 5 to 10 phr of natural polyisoprene and from 40 to 60 p
- the at least one further diene rubber is particularly preferably two different diene rubbers.
- the two different diene rubbers are styrene-butadiene rubber and natural polyisoprene.
- Rubber mixture 5 to 15 phr at least one natural and / or synthetic
- Such a rubber mixture shows in comparison to a rubber mixture containing the same amount of butadiene rubber with a T g of -105 ° C from the prior Technique includes behaving an improved roll resistance, the rest being
- Tire properties will not be significantly worsened and / or remain the same.
- wet grip performance and tear properties remain at a level acceptable for use in vehicle tire treads.
- Such a rubber composition replaces a rubber composition of the prior art with the same glass transition temperature, wherein compared to the prior art by the use of the described functionalized styrene-butadiene rubber having a T g of -87 to -80 ° C simultaneously the amount of High-T g -SSBRs can be increased, resulting in a simultaneous improvement of the
- the rubber mixture may further contain at least one further diene rubber, in particular natural and /
- Such a rubber mixture replaces a rubber mixture of the prior art with the same glass transition temperature, which compared to the prior art by the use of the described functionalized styrene-butadiene rubber having a T g of -120 to -75 ° C, preferably from -. 110 to -75 ° C, more preferably from -110 to -80 ° C, most preferably from -87 to -80 ° C at the same time the amount of high-T g -SSBRs can be increased, resulting in a simultaneous
- the fiction, contemporary rubber mixture contains 20 to 300 phr, preferably 20 to 150 phr, more preferably 40 to 150 phr and most preferably 80 to 110 phr of at least one silica.
- the rubber composition according to the invention may contain, in addition to silica, other known polar and / or nonpolar fillers, such as e.g. Soot, included.
- the silicas may be the silicas known to those skilled in the art which are suitable as a filler for tire rubber mixtures. However, it is particularly preferred if a finely divided, precipitated silica is used which has a nitrogen surface area (BET surface area) (according to DIN ISO 9277 and DIN 66132) of 35 to 350 m 2 / g, preferably from 35 to 260 m 2 / g, more preferably from 100 to 260 m 2 / g and most preferably from 130 to 235 m 2 / g, and a CTAB surface area (according to ASTM D 3765) of from 30 to 400 m 2 / g, preferably from 30 to 250 m 2 / g, particularly preferably from 100 to 250 m 2 / g and very particularly preferably from 125 to 230 m 2 / g.
- BET surface area nitrogen surface area
- CTAB surface area accordinging to ASTM D 3765
- Such silicas lead z. B. in rubber compounds for tire strip to particularly good physical properties of the vulcanizates.
- silicas can thus z. B. both those of the type Ultrasil® VN3 (Trade name) of Evonik as well as highly dispersible silicas, so-called HD silicas (eg Zeosil® 1165 MP from Rhodia) are used.
- a coupling agent in the form of silane or an organosilicon compound, is preferably used.
- one or more different silane coupling agents can be used in combination with each other.
- Rubber mixture may thus contain a mixture of different silanes.
- 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 blends known silane coupling agents can be used.
- Such known from the prior art coupling agents are bifunctional organosilanes having on the silicon atom at least one alkoxy, cycloalkoxy or phenoxy group as a leaving group and have as other functionality a group which may optionally undergo a chemical reaction with the double bonds of the polymer after cleavage , In the latter group may be z.
- they may be the following chemical groups:
- silane coupling agents z. 3-mercaptopropyltriethoxysilane
- TESPT Sulfur atoms with different contents of the different sulfides.
- TESPT can also be used as a mixture with carbon black
- silane mixture which comprises 40 to 100% by weight of disulfides, particularly preferably 55 to 85% by weight of disulfides and very particularly preferably 60 to 80% by weight of disulfides.
- blocked mercaptosilanes as z. B. from WO 99/09036 are known, can be used as a silane coupling agent.
- Silanes as described in WO 2008/083241 Al, WO 2008/083242 Al, WO 2008/083243 Al and WO 2008/083244 Al, can also be used. Suitable for. B. silanes, which are sold under the name NXT in different variants by the company Momentive, USA, or those sold under the name VP Si 363® by Evonik Industries.
- the amount of coupling agent is preferably 0.1 to 20 phr, more preferably 1 to 15 phr.
- the rubber mixture contains 80 to 110 phr of silica. This results in particularly good Abriebeigenschaften at the same time good tear properties and improved dry braking properties.
- 2 to 15, particularly preferably 2 to 10, phr of carbon black are additionally preferably contained in the rubber mixture.
- Rubber mixture 40 to 60 phr of at least one carbon black This results in a particularly high improvement in Abriebeigenschaften compared to the prior art, while the stiffness is increased, so that the handling behavior is further improved. At the same time, this rubber compound shows a particularly high improvement in the rolling resistance properties.
- Suitable carbon blacks are all types of carbon black known to those skilled in the art.
- the carbon black has an iodine value, according to ASTM D 1510, which is also referred to as Jodadsorptionskohl between 30 g / kg and 250 g / kg, preferably 30 to 180 g / kg, particularly preferably 40 to 180 g / kg, and most preferably 40 to 130 kg / g, and a DBP number according to ASTM D 2414 of 80 to 200 ml / 100 g, preferably 100 to 200 ml / 100g, more preferably 115 to 200 ml / 100g.
- the DBP number according to ASTM D 2414 determines the specific absorption volume of a carbon black or a light filler by means of dibutyl phthalate.
- the rubber mixture carbon nanotubes (CNT) including discrete CNTs, so-called hollow carbon fibers (HCF) and modified CNT containing one or more functional groups, such as hydroxyl, carboxyl and carbonyl groups).
- CNT carbon nanotubes
- HCF hollow carbon fibers
- modified CNT containing one or more functional groups such as hydroxyl, carboxyl and carbonyl groups
- the rubber composition may also contain other polar fillers such as aluminosilicates, chalk, starch, magnesia, titania or rubber gels.
- polar fillers such as aluminosilicates, chalk, starch, magnesia, titania or rubber gels.
- the rubber mixture There may be present in the rubber mixture from 0 to 70 phr, preferably 0.1 to 60 phr, preferably 0.1 to 50 phr, of at least one plasticizer.
- plasticizers known to those skilled in the art, such as aromatic,
- mineral oil this is preferably selected from the group consisting of DAE (Distilled Aromatic Extracts) and / or RAE (Residual Aromatic Extract) and / or TDAE (Treated Distilled Aromatic Extracts) and / or MES (Mild Extracted Solvents) and / or naphthenic oils.
- the rubber mixture according to the invention may contain customary additives in customary parts by weight. These additives include
- anti-aging agents such as. N-phenyl-N '- (1,3-dimethylbutyl) -p-phenylenediamine (6PPD), N, N'-diphenyl-p-phenylenediamine (DPPD), N, N'-ditolyl-p-phenylenediamine (DTPD ), N-isopropyl-N'-phenyl-p-phenylenediamine (IPPD), 2,2,4-trimethyl-1,2-dihydroquinoline (TMQ),
- N-phenyl-N '- (1,3-dimethylbutyl) -p-phenylenediamine 6PPD
- DPPD N, N'-diphenyl-p-phenylenediamine
- DTPD N, N'-ditolyl-p-phenylenediamine
- IPPD N-isopropyl-N'-phenyl-p-phenylenediamine
- TMQ 2,2,4-tri
- activators such as Zinc oxide and fatty acids (eg stearic acid),
- Mastikationswhismittel such. 2,2'-dibenzamidodiphenyl disulphide (DBD) and f) processing aids, e.g. Fatty acid salts, e.g. Zinc soaps, and fatty acid esters and their derivatives.
- DBD 2,2'-dibenzamidodiphenyl disulphide
- processing aids e.g. Fatty acid salts, e.g. Zinc soaps, and fatty acid esters and their derivatives.
- the rubber mixture according to the invention when using the rubber composition according to the invention for the inner components of a tire or a technical rubber article, which have direct contact with existing reinforcements, the rubber mixture is usually added to a suitable adhesive system, often in the form of adhesive resins.
- the proportion of the total amount of further additives is 3 to 150 phr, preferably 3 to 100 phr and more preferably 5 to 80 phr.
- the conventionally used zinc oxide usually has a BET surface area of less than 10 m 2 / g. However, it is also possible to use so-called nano-zinc oxide having a BET surface area of 10 to 60 m 2 / g.
- the vulcanization is carried out in the presence of sulfur or sulfur donors by means of vulcanization accelerators, with some
- Vulkanisationsbelixer at the same time can act as a sulfur donor.
- Sulfur or sulfur donors and one or more accelerators are in the last
- the accelerator is selected from the group consisting of thiazole accelerators and / or mercapto accelerators and / or sulfenamide accelerators and / or
- Xanthogenate accelerators and / or guanidine accelerators.
- a sulfenamide accelerator selected from the group consisting of N-cyclohexyl-2-benzothiazolesufenamid (CBS) and / or N, N-dicyclohexylbenzothiazole-2-sulfenamide (DCBS) and / or benzothiazyl-2-sulfenmorpholide (MBS ) and / or N-tert-butyl-2-benzothiazyl sulfenamide (TBBS).
- CBS N-cyclohexyl-2-benzothiazolesufenamid
- DCBS N-dicyclohexylbenzothiazole-2-sulfenamide
- MBS benzothiazyl-2-sulfenmorpholide
- TBBS N-tert-butyl-2-benzothiazyl sulfenamide
- vulcanizing agent which cross-links with a functionality greater than four and at least one vulcanization accelerator.
- the vulcanizing agent which has a functionality of greater than four, for example, the general formula A):
- G [C a H 2a -CH 2 -S b Y] c
- G is a polyvalent cyclic hydrocarbon group and / or a polyvalent heterohydrocarbon group and / or a polyvalent siloxane group containing 1 to 100 atoms; wherein each Y independently selected from a rubber active group contains sulfur-containing functionalities; and wherein a, b and c are integers for which independently: a is 0 to 6; b is 0 to 8; and c is 3 to 5.
- the rubber-active group is preferably selected from a thiosulfonate group, a dithiocarbamate group, a thiocarbonyl group, a mercapto group, a hydrocarbon group and a sodium thiosulfonate group (Bunte salt group).
- Sulfur and sulfur donors including sulfur donating silanes such as TESPT, and vulcanization accelerators as described above and vulcanizing agents crosslinking with a functionality greater than four, as described in WO 2010/049261 A2, e.g. a vulcanizing agent of the formula A), and the above-mentioned systems Vulkuren®, Duralink® and Perkalink® conceptually summarized as a vulcanizing agent.
- the fiction, contemporary rubber mixture preferably contains at least one
- Vulcanizing agent selected from the group consisting of sulfur and / or
- Sulfur donors and / or vulcanization accelerators and / or vulcanizing agents which crosslink with a functionality greater than four. This can be from the
- rubber composition according to the invention vulcanizates, in particular for use in vehicle tires produce.
- the fiction, contemporary rubber mixture preferably contains at least one
- Vulcanizing agents selected from the group consisting of sulfur and / or sulfur donors and / or vulcanization accelerators and / or vulcanizing agents which crosslink with a functionality greater than four. This can be from the
- rubber composition according to the invention vulcanizates, in particular for use in vehicle tires produce.
- vulcanization retarders may be present in the rubber compound.
- a plurality of accelerators are used. Preference is given to using a sulfenamide accelerator, particularly preferably CBS, in combination with the guanidine accelerator DPG (diphenylguanidine).
- the Amount of DPG is 0 to 5 phr, preferably 0.1 to 3 phr, more preferably 0.5 to 2.5 phr, most preferably 1 to 2.5 phr.
- Another object of the present invention is to provide a vehicle tire characterized by improved rolling resistance performance and improved abrasion performance. This object is achieved in that the vehicle tire in at least one component contains the rubber mixture according to the invention as described above. All the above explanations regarding the components and their characteristics apply.
- the component is preferably a tread. As is known to those skilled in the tread contributes to a relatively high proportion of the total drag and significantly to the abrasion of the tire.
- the invention is further based on the object, the abrasion behavior of
- Rubber mixture for the production of vehicle tires, in particular for the production of the tread of a tire and / or a body mixture of a tire and the
- inner tire components are essentially squeegee, sidewall, inner lining (inner layer), core profile, belt, shoulder, belt profile,
- Carcass bead reinforcement, bead profile, horn profile and bandage.
- Mixing stages is a basic mixture with all components except the vulcanization system (sulfur and vulkanisationsbeeinflus sende substances) is produced. By adding of the vulcanization system in a final mixing stage, the finished mixture is produced. The finished mixture is further processed eg by an extrusion process and brought into the appropriate form.
- the vulcanization system sulfur and vulkanisationsbeeinflus sende substances
- the mixture is preferably made in the form of a tread and applied as known in the manufacture of the vehicle tire blank.
- the tread may also be in the form of a narrow
- Rubber composition according to the invention can be used both for the cap and for the base.
- the extruded mixture is shaped into the appropriate shape and often or subsequently with reinforcing materials, e.g. synthetic fibers or steel cords. In most cases, this results in a multi-layered structure, consisting of one and / or several layers of rubber mixture, one and / or more layers of identical and / or different reinforcement and one and / or several other layers of the like and / or another rubber mixture.
- BR polybutadiene, high-cis, Nd-catalyzed butadiene rubber
- DPG diphenylguanidine
- CBS N-cyclohexyl-2-benzothiazolesufenamide
- the rubber blends of the present invention El, E2 and E3, surprisingly exhibit greater rebound resilience at 70 ° C than VI, although the glass transition temperatures Tg of El, E2 and E3 are each greater than those of VI.
- a greater rebound resilience at 70 ° C is an indicator of an improved
- the rubber compounds E4, E5 and E6 of the present invention exhibit improved abrasion and rolling resistance properties at the same glass transition temperature (the rubber composition) as their comparative mixture V2 (see FIG.
- rubber mixtures according to the invention possible to increase the proportion of high-T g rubber and thus at the same time the abrasion and rolling resistance of the Rubber compound to improve. At the same time, the remaining physical properties remain almost at the same level.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201480053450.5A CN105579507B (zh) | 2013-09-27 | 2014-09-04 | 硫可交联的橡胶混合物 |
BR112016004453-3A BR112016004453B1 (pt) | 2013-09-27 | 2014-09-04 | mistura de borracha reticulável com enxofre, seu uso, e pneu para veículos automotivos |
US15/073,211 US9856368B2 (en) | 2013-09-27 | 2016-03-17 | Sulfur-crosslinkable rubber mixture |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP13186373.0 | 2013-09-27 | ||
EP13186373.0A EP2853558B1 (de) | 2013-09-27 | 2013-09-27 | Schwefelvernetzbare Kautschukmischung |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US15/073,211 Continuation US9856368B2 (en) | 2013-09-27 | 2016-03-17 | Sulfur-crosslinkable rubber mixture |
Publications (1)
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WO2015043902A1 true WO2015043902A1 (de) | 2015-04-02 |
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ID=49293493
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PCT/EP2014/068786 WO2015043902A1 (de) | 2013-09-27 | 2014-09-04 | Schwefelvernetzbare kautschukmischung |
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US (1) | US9856368B2 (de) |
EP (1) | EP2853558B1 (de) |
CN (1) | CN105579507B (de) |
BR (1) | BR112016004453B1 (de) |
ES (1) | ES2612554T3 (de) |
WO (1) | WO2015043902A1 (de) |
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Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07238187A (ja) * | 1994-02-28 | 1995-09-12 | Asahi Chem Ind Co Ltd | タイヤトレッド用ゴム組成物 |
US20050272852A1 (en) * | 2004-06-02 | 2005-12-08 | Sandstrom Paul H | Natural rubber-rich composition and tire with tread thereof |
EP1884376A1 (de) * | 2006-08-03 | 2008-02-06 | The Yokohama Rubber Co., Ltd. | Luftreifen |
DE102007060859A1 (de) * | 2007-12-18 | 2009-06-25 | Continental Aktiengesellschaft | Kautschukmischung, insbesondere für Fahrzeugreifen |
EP2113531A2 (de) * | 2008-04-23 | 2009-11-04 | Continental Aktiengesellschaft | Kautschukmischung mit verbessertem Alterungsverhalten |
EP2289712A1 (de) * | 2009-08-31 | 2011-03-02 | The Goodyear Tire & Rubber Company | Reifen mit Kautschuklauffläche mit einer Kombination aus einer Harzmischung und funktionalisiertem Elastomer |
EP2345696A1 (de) * | 2010-01-12 | 2011-07-20 | Continental Reifen Deutschland GmbH | Kautschukmischung mit verbessertem Rollwiderstand und verbessertem Trockenbremsen |
EP2357211A1 (de) * | 2010-02-17 | 2011-08-17 | Continental Reifen Deutschland GmbH | Schwefelvernetzbare Kautschukmischung |
WO2011162771A1 (en) * | 2010-06-25 | 2011-12-29 | Michelin Recherche Et Technique S.A. | Low rolling resistance tread for cars and light trucks |
EP2404964A1 (de) * | 2010-07-07 | 2012-01-11 | Continental Reifen Deutschland GmbH | Kautschukmischung |
US20130059965A1 (en) * | 2010-05-26 | 2013-03-07 | The Yokohama Rubber Co., Ltd | Tire tread rubber composition |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4358154A (en) | 1980-12-05 | 1982-11-09 | Boeing Vertol Company | Vehicle crashworthy seat |
JP2714971B2 (ja) | 1989-01-30 | 1998-02-16 | 横浜ゴム株式会社 | タイヤトレッド用ゴム組成物 |
DE69423585T2 (de) | 1993-12-27 | 2000-07-20 | Sumitomo Rubber Industries Ltd., Kobe | Kautschukmischungen für Lauffläche eines Reifens |
US6812822B1 (en) | 1997-01-09 | 2004-11-02 | Donald Spector | Combined audio/video monitor and light box assembly |
EP1679315A1 (de) | 1997-08-21 | 2006-07-12 | General Electric Company | Blockierte Merkaptosilane als Kupplungsmittel für gefüllte Kautschukzusammensetzung |
US5901766A (en) | 1997-08-26 | 1999-05-11 | The Goodyear Tire & Rubber Company | Pneumatic tire having a tread compound containing high levels of low Tg polymer and resin |
US6127472A (en) * | 1997-11-11 | 2000-10-03 | Jsr Corporation | Rubber composition |
JP2002322317A (ja) | 2001-04-24 | 2002-11-08 | Yokohama Rubber Co Ltd:The | タイヤトレッド用ゴム組成物 |
EP1323777A1 (de) | 2001-12-28 | 2003-07-02 | JSR Corporation | Kautschukzusammensetzung und Befestigungsvorrichtung zur Vibrationsisolation auf Basis von dieser Kautschukzusammensetzung |
WO2003102053A1 (fr) | 2002-05-31 | 2003-12-11 | Zeon Corporation | Caoutchouc dienique conjugue, procede de fabrication et composition de caoutchouc |
RU2418013C2 (ru) | 2005-10-19 | 2011-05-10 | Дау Глобал Текнолоджиз Инк. | Эластомерные полимеры, модифицированные по концам цепей силансульфидом |
US7968633B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing free-flowing filler compositions |
US7968636B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing silated cyclic core polysulfides |
US7968634B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing silated core polysulfides |
US7968635B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing free-flowing filler compositions |
DE102007031986A1 (de) | 2007-07-10 | 2009-01-15 | Continental Aktiengesellschaft | Kautschukmischung, insbesondere für Reifen |
EP2070952A1 (de) * | 2007-12-14 | 2009-06-17 | Continental Aktiengesellschaft | Vulkanisierbare Gummimischung und deren Verwendung für Gummiprodukte |
US20110207847A1 (en) * | 2007-12-28 | 2011-08-25 | Bridgestone Corporation | Tire |
FR2937719B1 (fr) | 2008-10-29 | 2013-12-27 | Valeo Systemes Thermiques | Ailette pour echangeur de chaleur et echangeur de chaleur comportant une telle ailette |
US8124206B2 (en) | 2008-10-30 | 2012-02-28 | Momentive Performance Materials, Inc. | Sulfur-containing cycloaliphatic compound, filled sulfur-vulcanizable elastomer composition containing sulfur-containing cycloaliphatic compound and articles fabricated therefrom |
US8426512B2 (en) | 2009-08-31 | 2013-04-23 | The Goodyear Tire & Rubber Company | Rubber composition containing silica reinforcement and functionalized polybutadiene rubber and tires having a component thereof |
-
2013
- 2013-09-27 EP EP13186373.0A patent/EP2853558B1/de active Active
- 2013-09-27 ES ES13186373.0T patent/ES2612554T3/es active Active
-
2014
- 2014-09-04 BR BR112016004453-3A patent/BR112016004453B1/pt active IP Right Grant
- 2014-09-04 CN CN201480053450.5A patent/CN105579507B/zh active Active
- 2014-09-04 WO PCT/EP2014/068786 patent/WO2015043902A1/de active Application Filing
-
2016
- 2016-03-17 US US15/073,211 patent/US9856368B2/en active Active
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07238187A (ja) * | 1994-02-28 | 1995-09-12 | Asahi Chem Ind Co Ltd | タイヤトレッド用ゴム組成物 |
US20050272852A1 (en) * | 2004-06-02 | 2005-12-08 | Sandstrom Paul H | Natural rubber-rich composition and tire with tread thereof |
EP1884376A1 (de) * | 2006-08-03 | 2008-02-06 | The Yokohama Rubber Co., Ltd. | Luftreifen |
DE102007060859A1 (de) * | 2007-12-18 | 2009-06-25 | Continental Aktiengesellschaft | Kautschukmischung, insbesondere für Fahrzeugreifen |
EP2113531A2 (de) * | 2008-04-23 | 2009-11-04 | Continental Aktiengesellschaft | Kautschukmischung mit verbessertem Alterungsverhalten |
EP2289712A1 (de) * | 2009-08-31 | 2011-03-02 | The Goodyear Tire & Rubber Company | Reifen mit Kautschuklauffläche mit einer Kombination aus einer Harzmischung und funktionalisiertem Elastomer |
EP2345696A1 (de) * | 2010-01-12 | 2011-07-20 | Continental Reifen Deutschland GmbH | Kautschukmischung mit verbessertem Rollwiderstand und verbessertem Trockenbremsen |
EP2357211A1 (de) * | 2010-02-17 | 2011-08-17 | Continental Reifen Deutschland GmbH | Schwefelvernetzbare Kautschukmischung |
US20130059965A1 (en) * | 2010-05-26 | 2013-03-07 | The Yokohama Rubber Co., Ltd | Tire tread rubber composition |
WO2011162771A1 (en) * | 2010-06-25 | 2011-12-29 | Michelin Recherche Et Technique S.A. | Low rolling resistance tread for cars and light trucks |
EP2404964A1 (de) * | 2010-07-07 | 2012-01-11 | Continental Reifen Deutschland GmbH | Kautschukmischung |
Cited By (32)
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CN108136827A (zh) * | 2015-10-08 | 2018-06-08 | 米其林集团总公司 | 包含链中部具有官能团的二烯弹性体的橡胶组合物 |
WO2017064235A1 (fr) | 2015-10-16 | 2017-04-20 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
US11365308B2 (en) | 2015-10-16 | 2022-06-21 | Compagnie Generale Des Etablissements Michelin | Rubber composition including a specific hydrocarbon resin |
US11802194B2 (en) | 2015-10-16 | 2023-10-31 | Compagnie Generale Des Etablissements Michelin | Rubber composition including a specific hydrocarbon resin |
CN108602986A (zh) * | 2016-01-26 | 2018-09-28 | 大陆轮胎德国有限公司 | 橡胶混合物及充气车辆轮胎 |
WO2017129276A1 (de) * | 2016-01-26 | 2017-08-03 | Continental Reifen Deutschland Gmbh | Kautschukmischung und fahrzeugluftreifen |
CN108602986B (zh) * | 2016-01-26 | 2020-11-06 | 大陆轮胎德国有限公司 | 橡胶混合物及充气车辆轮胎 |
WO2017168099A1 (fr) | 2016-03-31 | 2017-10-05 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
JP2019516816A (ja) * | 2016-03-31 | 2019-06-20 | コンパニー ゼネラール デ エタブリッスマン ミシュラン | 特定の炭化水素系樹脂を含むゴム組成物 |
CN106519353A (zh) * | 2016-10-28 | 2017-03-22 | 无锡市永兴金属软管有限公司 | 一种用于制备物料吸送软管的丁苯橡胶 |
CN110099804B (zh) * | 2016-12-20 | 2021-08-10 | 米其林集团总公司 | 包括经改性的二烯弹性体的橡胶组合物 |
CN110099804A (zh) * | 2016-12-20 | 2019-08-06 | 米其林集团总公司 | 包括经改性的二烯弹性体的橡胶组合物 |
US11220591B2 (en) | 2016-12-22 | 2022-01-11 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising a specific hydrocarbon resin |
WO2018115622A1 (fr) | 2016-12-22 | 2018-06-28 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
WO2018115623A1 (fr) | 2016-12-22 | 2018-06-28 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
WO2018115621A1 (fr) | 2016-12-22 | 2018-06-28 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
US11203680B2 (en) | 2016-12-22 | 2021-12-21 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising a specific hydrocarbon resin |
WO2018189496A1 (fr) | 2017-04-14 | 2018-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une resine hydrocarbonee specifique |
US11492465B2 (en) | 2017-04-14 | 2022-11-08 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising a specific hydrocarbon resin |
WO2021018546A1 (en) | 2019-07-26 | 2021-02-04 | Compagnie Generale Des Etablissements Michelin | Tire incorporating a rubber composition including a specific hydrocarbon resin |
WO2021018547A1 (en) | 2019-07-26 | 2021-02-04 | Compagnie Generale Des Etablissements Michelin | Tire incorporating a rubber composition including a specific hydrocarbon resin |
WO2021018545A1 (en) | 2019-07-26 | 2021-02-04 | Compagnie Generale Des Etablissements Michelin | Tire incorporating a rubber composition including a specific hydrocarbon resin |
WO2021018548A1 (en) | 2019-07-26 | 2021-02-04 | Compagnie Generale Des Etablissements Michelin | Tire incorporating a rubber composition including a specific hydrocarbon resin |
FR3099169A1 (fr) | 2019-07-26 | 2021-01-29 | Compagnie Generale Des Etablissements Michelin | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
FR3099167A1 (fr) | 2019-07-26 | 2021-01-29 | Compagnie Generale Des Etablissements Michelin | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
FR3099168A1 (fr) | 2019-07-26 | 2021-01-29 | Compagnie Generale Des Etablissements Michelin | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
FR3099166A1 (fr) | 2019-07-26 | 2021-01-29 | Compagnie Generale Des Etablissements Michelin | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
FR3119169A1 (fr) | 2021-01-26 | 2022-07-29 | Compagnie Generale Des Etablissements Michelin | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
FR3119168A1 (fr) | 2021-01-26 | 2022-07-29 | Compagnie Generale Des Etablissements Michelin | Pneu incorporant une composition de caoutchouc comprenant une résine hydrocarbure spécifique |
WO2022161742A1 (en) | 2021-01-26 | 2022-08-04 | Compagnie Generale Des Etablissements Michelin | Tire incorporating a rubber composition including a specific hydrocarbon resin |
WO2022161741A1 (en) | 2021-01-26 | 2022-08-04 | Compagnie Generale Des Etablissements Michelin | Tire incorporating a rubber composition including a specific hydrocarbon resin |
Also Published As
Publication number | Publication date |
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CN105579507A (zh) | 2016-05-11 |
CN105579507B (zh) | 2017-09-08 |
ES2612554T3 (es) | 2017-05-17 |
EP2853558A1 (de) | 2015-04-01 |
US9856368B2 (en) | 2018-01-02 |
US20160194485A1 (en) | 2016-07-07 |
BR112016004453B1 (pt) | 2020-12-08 |
EP2853558B1 (de) | 2016-11-09 |
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