[go: up one dir, main page]

WO2025223798A1 - Mélange de caoutchouc réticulable au soufre, produit de vulcanisation du mélange de caoutchouc et pneu de véhicule - Google Patents

Mélange de caoutchouc réticulable au soufre, produit de vulcanisation du mélange de caoutchouc et pneu de véhicule

Info

Publication number
WO2025223798A1
WO2025223798A1 PCT/EP2025/058927 EP2025058927W WO2025223798A1 WO 2025223798 A1 WO2025223798 A1 WO 2025223798A1 EP 2025058927 W EP2025058927 W EP 2025058927W WO 2025223798 A1 WO2025223798 A1 WO 2025223798A1
Authority
WO
WIPO (PCT)
Prior art keywords
groups
rubber
sulfur
phr
rubber compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2025/058927
Other languages
German (de)
English (en)
Inventor
Andreas Wolf
Julia Große
Christoph Vatterott
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.)
Continental Reifen Deutschland GmbH
Original Assignee
Continental Reifen Deutschland GmbH
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 Reifen Deutschland GmbH filed Critical Continental Reifen Deutschland GmbH
Publication of WO2025223798A1 publication Critical patent/WO2025223798A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • 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

Definitions

  • the invention relates to a sulfur-curable rubber compound, its vulcanizate, and a vehicle tire. Furthermore, the invention relates to the use of the sulfur-curable rubber compound.
  • the rubber composition of the tread largely determines the driving characteristics of a vehicle tire, especially a pneumatic tire.
  • the present invention was based on the objective of providing a rubber compound which, compared to the prior art, as published, for example, in DE 102017 221 232 A1 or WO 2023 104 252 A1, exhibits an overall improvement in the property profile encompassing rolling resistance behavior, abrasion behavior, in particular abrasion resistance, and wet braking properties.
  • the rubber compound, vulcanizate, and vehicle tire according to the invention achieve an improvement in the conflicting objectives of rolling resistance, abrasion resistance (especially wear resistance), and wet braking performance (especially wet grip).
  • the rolling resistance is improved.
  • the rubber compound according to the invention exhibits good processability, in particular mixability and extrudability, so that the vulcanizate and the vehicle tire according to the invention are also easy to process.
  • the invention encompasses all advantageous embodiments, which are reflected, inter alia, in the claims.
  • the invention also encompasses embodiments resulting from the combination of different features, for example, components of the rubber compound, and different degrees of preference given to these features, such that a combination of a first feature designated as "preferred” or described within an advantageous embodiment with a further feature designated, for example, as “particularly preferred,” is also encompassed by the invention.
  • the unit phr (parts per hundred parts of rubber by weight) used in this document is the standard unit of measurement for compound formulations in the rubber industry.
  • the dosage of the parts by weight of the individual substances is expressed in this document as a percentage of 100 parts by weight of the total mass of all rubbers present in the mixture, with a molecular weight Mw measured using gel permeation chromatography (GPC) in accordance with ISO 13885-1 of greater than 20,000 g/mol.
  • the rubber mixture contains at least one diene rubber from the group consisting of natural polyisoprene (NR) and synthetic polyisoprene (IR).
  • the rubber mixture further contains at least one diene rubber, which is a butadiene rubber (synonyms: BR, BR rubber, polybutadiene).
  • diene rubber which is a butadiene rubber (synonyms: BR, BR rubber, polybutadiene).
  • butadiene rubber according to the invention is explicitly not one of the diene rubbers mentioned below, such as butadiene-isoprene rubber or styrene-butadiene rubber.
  • diene rubbers that may be present in smaller quantities in the mixture according to the invention are butadiene-isoprene rubber, styrene-butadiene rubber (SBR), in particular solution-polymerized styrene-butadiene rubber (SSBR) and emulsion-polymerized styrene-butadiene rubber (ESBR), styrene-isoprene rubber, halobutyl rubber, polynorbornene, isoprene-isobutylene copolymer, ethylene-propylene-diene rubber, nitrile rubber, chloroprene rubber, acrylate rubber, fluorocarbon rubber, silicone rubber, polysulfide rubber, epichlorohydrin rubber, styrene-isoprene-butadiene terpolymer, hydrogenated Acrylonitrile butadiene rubber and hydrogenated styrene butadiene rubber.
  • SBR sty
  • the mixture preferably does not include liquid rubbers, and in particular does not include rubbers that are liquid at room temperature and ambient pressure.
  • nitrile rubber hydrogenated acrylonitrile butadiene rubber, chloroprene rubber, butyl rubber, halobutyl rubber, or ethylene propylene diene monomer rubber are used in the manufacture of technical rubber articles such as belts, straps, and hoses, and/or shoe soles.
  • the following are used in this process: Experts know that these rubbers have a preferred application in terms of their mixture compositions, which are known with regard to fillers, plasticizers, vulcanization systems and additives.
  • the diene rubber according to the invention comprises 50 to 100 phr polyisoprene, preferably 55 to 85 phr polyisoprene, particularly preferably 60 to 80 phr, which is preferably natural polyisoprene (NR).
  • phr polyisoprene preferably 55 to 85 phr polyisoprene, particularly preferably 60 to 80 phr, which is preferably natural polyisoprene (NR).
  • the diene rubber according to the invention further comprises 0 to 50 phr butadiene rubber (BR), preferably 10 to 40 phr, particularly preferably 15 to 25 phr butadiene rubber.
  • BR butadiene rubber
  • the combination of 50 to 100, preferably 55 to 85 phr, particularly preferably 60 to 80 phr polyisoprene, preferably natural polyisoprene (NR), and 0 to 50 phr, preferably 10 to 40 phr, particularly preferably 15 to 25 phr butadiene rubber (BR) solves the problem underlying the invention particularly well and the rubber mixture exhibits particularly optimal processability.
  • the proportions of NR and BR add up to approximately 100 phr or exactly 100.00 phr.
  • the rubber mixture contains less than 100 phr of NR and BR, at least one further rubber, preferably at least one further diene rubber selected from the above list, is included, such that the sum of the contained rubbers by definition equals 100 phr.
  • the butadiene rubber (polybutadiene, BR) contained in the rubber compound according to the invention is preferably of the low-cis type.
  • the so-called high-cis and low-cis types refer to polybutadienes with a cis content greater than or equal to 90 wt.% (weight %, high-cis type) and polybutadienes with a cis content less than 90 wt.% (low-cis type), respectively.
  • the polybutadienes used can be end-group modified and/or functionalized along the polymer chains.
  • Polybutadienes can be modified simply or in any number of ways. These modifications can involve hydroxy groups, ethoxy groups, epoxy groups, siloxane groups, amino groups, aminosiloxane groups, carboxy groups, phthalocyanine groups, and/or silane sulfide groups.
  • Other modifications, also known as functionalizations, are also possible and are known to experts. These functionalizations can include metal atoms.
  • the BR rubber used in the present rubber compound is a BR specifically functionalized for the bonding of silicon dioxide or silica, preferably having a glass transition temperature Tg below -70 °C, more preferably below -75 °C.
  • the glass transition temperature Tg is preferably not colder than -110 °C, more preferably not colder than -100 °C, and more preferably not below -95 °C.
  • a preferred glass transition temperature is between -85 °C and -95 °C or between -75 °C and -85 °C.
  • the BR rubber used in the present rubber compound is preferably of the low-cis type.
  • the chain ends of the BR rubber used in the present rubber compound are preferably functionalized for the attachment of silicas.
  • the BR rubber used in the present rubber compound is preferably not oil-extended.
  • the BR rubber used in the present rubber compound preferably has a weight-average molar mass Mw, measured by GPC (in accordance with ISO 13885-1), in the range of 200000 to 2000000 g/mol, preferably in the range of 250000 to 1000000 g/mol, particularly preferably in the range of 300000 to 750000 g/mol, particularly preferably between 300000 and 600000 g/mol.
  • Mw weight-average molar mass Mw
  • the BR rubber functionalized for silica is preferably mixed in the present rubber mixture with a high-surface-area silicon dioxide, as specified in more detail later.
  • the functionalized BR rubber can have several functionalizations and, for example, can also be functionalized for interaction with carbon black.
  • the combination results in an unexpectedly significant performance advantage for the rubber compound. This includes a marked improvement in rolling resistance, unexpectedly improved wet braking performance, and unexpectedly good abrasion resistance.
  • the rubber mixture contains as a further component 20 to 100 phr, preferably 30 to 70 phr, particularly preferably 40 to 60 phr, more preferably 45 to 55 phr of at least one silicon dioxide.
  • the at least one silicon dioxide has a mean nitrogen surface area (BET surface area) according to DIN ISO 9277 of at least 210 m2/g (square meters per gram), preferably 210 to 425 m2/g, more preferably 210 to 320 m2/g, more preferably 265 to 320 m2/g.
  • the at least one silicon dioxide preferably further exhibits a mean CTAB surface area according to ASTM D 3765 of over 200 m2/g, preferably 200 to 400 m2/g, more preferably 200 to 300 m2/g, particularly preferably 245 to 300 m2/g.
  • the at least one silicon dioxide is preferably amorphous silicon dioxide, preferably precipitated silica, which is also referred to as precipitated silicon dioxide.
  • the silicon dioxide used has an extremely high specific surface area and is classified as Ultra High Surface silicon dioxide.
  • the present invention has succeeded in achieving good abrasion resistance, good processability, and surprisingly improved rolling resistance properties.
  • a suitable silicon dioxide with an average BET surface area of 275 m2/g and an average CTAB surface area of 250 m2/g is available, for example, under the trade name Premium SW from Solvay Silica Korea Co., Ltd.
  • the rubber compound of these aforementioned embodiments also contains comparatively small amounts of plasticizers, preferably in amounts of 0 to 20 phr, more preferably 0 to 10 phr, and particularly preferably 1 to 5 phr.
  • the plasticizer(s) contained are preferably selected from the substances listed below.
  • the rubber compound according to the invention can also contain at least one further filler that has a reinforcing effect or does not have a reinforcing effect.
  • reinforcing fillers are in particular carbon blacks, preferably selected from industrial carbon blacks and pyrolysis carbon blacks, with industrial carbon blacks being further preferred, and further silicon dioxides which have a CTAB surface area according to ASTM D 3765 of less than 190 m2/g.
  • the carbon black has an iodine number, according to ASTM D 1510, also referred to as the iodine adsorption number, between 30 and 250 g/kg, preferably 40 to 180 g/kg, particularly preferably 40 to 100 g/kg, and most preferably 60 to 90 g/kg.
  • the carbon blacks used preferably have a DBP value according to ASTM D 2414 of 80 to 200 ml/100 g, preferably 100 to 200 ml/100 g, and particularly preferably 110 to 180 ml/100 g.
  • the DBP value according to ASTM D 2414 determines the specific absorption volume of a carbon black or a light-colored filler using dibutyl phthalate.
  • the carbon blacks used also include so-called "recovered” carbon blacks.
  • the carbon blacks used may also be oxidized.
  • the total amount of soot contained corresponds to the quantities customary in the industry, preferably 0 to 50 phr.
  • the rubber compound may optionally contain coal.
  • it is used as
  • HTC coal is used, which is produced by hydrothermal carbonization of at least one starting material.
  • the abbreviation "HTC” stands for hydrothermal carbonization, a process known in the art. In this process, at least one starting material is heated together with water in a closed, pressure- and heat-resistant device, such as an autoclave. The resulting mixture is thus a suspension and/or solution of the starting material(s) in water. The heating process and the resulting steam generate increased pressure, which depends in particular on the temperature and the fill level of the device. Hydrothermal carbonization mimics the process that occurs naturally over millions of years to form lignite, but within a short time, usually just a few hours.
  • “HTC coal” refers to the solid product of hydrothermal carbonization.
  • Soot and coal can also be used as a mixture.
  • the rubber compound contains at least one further reinforcing filler selected from the group consisting of carbon blacks, preferably selected from industrial carbon blacks and pyrolysis carbon blacks, with industrial carbon blacks being further preferred.
  • a carbon black of type N339 is particularly suitable and preferred.
  • the fillers comprise little or no further silicon dioxides, which have a CTAB surface area according to ASTM D 3765 of less than 200 m2/g or a BET surface area of less than 210 m2/g.
  • "Little” here means an amount of at most 5 phr, preferably at most 1.5 phr.
  • Non-reinforcing fillers within the scope of the present invention include aluminosilicates, kaolin, chalk, starch, magnesium oxide, titanium dioxide or rubber gels as well as fibers (such as aramid fibers, glass fibers, carbon fibers, cellulose fibers).
  • Other potentially reinforcing fillers include, for example, carbon nanotubes (CNTs) including discrete CNTs, so-called hollow carbon fibers (HCF) and modified CNTs containing one or more functional groups, such as hydroxy, carboxy and carbonyl groups), graphite and graphene and so-called "carbon-silica dual-phase filier".
  • the rubber mixture further contains 1 to 30 pph silanes in the form of at least two organosilicon compounds.
  • the unit pph (parts per hundred parts of filler by weight) used in this document is the quantity commonly used in the rubber industry for coupling agents for fillers.
  • pf refers to all silicon dioxides present, including those contained according to the invention and any other silicon dioxides. This means that other fillers that may be present, such as carbon black, are not included in the calculation of the silane quantity.
  • the rubber mixture contains as silanes at least a) 1 to 30 ph, preferably 3 to 30 ph, particularly preferably 3 to 20 ph, most preferably 5 to 15 ph, at least one silane A selected from the silanes with the general formulas A-1) and A-Xl):
  • the silane A contained as component a) according to the invention is, by virtue of the Sx group, where the index x is an integer from 2 to 10, or by virtue of the SX group, a silane that can bind to polymers.
  • the mixture may also contain various silanes of type A, i.e., with different Sx and/or S-X groups.
  • the silane B contained according to the invention has no or only single sulfur atoms that cannot bond to the polymer chains of the diene rubber, since the chemical bond -C-S-C- does not usually open during vulcanization.
  • the silane B contained according to the invention is therefore a so-called “non-binding silane”, whereby in particular the “non-binding to diene rubbers” is meant.
  • the mixture may also contain various silanes of type B).
  • silane A Preferably, at least 5 pphf to 15 pphf of the silane according to formula A-XII are included as silane A:
  • at least 3 pphf to 10 pphf of the silane according to formula B-Il are included as silane B:
  • silanes A and B preferably the silanes according to formulas A-X1) and B-I1), in combination with the other components contained in the invention, the problem underlying the invention is solved particularly well.
  • the total amount of silanes A contained is 3 to 30 pphf, particularly preferably 3 to 20 pphf, and most preferably 5 to 15 pphf.
  • the total amount of silanes B contained is 2 to 30 pphf, particularly preferably 3 to 15 pphf, and most preferably 3 to 10 pphf.
  • silanes A and B particularly good properties are obtained with regard to the conflicting objectives of abrasion, rolling resistance, wet braking properties, and the processability of the rubber compound.
  • the molar ratio of silanes A to silanes B is particularly preferably 20:80 to 90:10, more preferably 45:55 to 80:20.
  • the rubber compound may contain common additives in usual proportions by weight, which are preferably added during its manufacture in at least one basic mixing stage.
  • additives include:
  • Ozone-protecting waxes and anti-aging agents such as diamines, like N-phenyl-N'-(1,3-dimethylbutyl)-p-phenylenediamine (6PPD), N,N'-diphenyl-p-phenylenediamine (DPPD), N,N'-ditolyl-p-phenylenediamine (DTPD), N-(1,4- dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD), N-isopropyl-N'-phenyl-p-phenylenediamine (IPPD), and/or dihydroquinolines, such as 2,2,4-trimethyl-1,2-dihydroquinoline (TMQ), and/or substituted bisphenols, such as 2,2'-methylenebis(4-methyl-6-tert-butylphenol) (BPH), and/or substituted phenols, such as butylhydroxytoluene (BHT),
  • diamines like
  • Activators such as zinc oxide and fatty acids (e.g., stearic acid) and/or other activators, such as zinc complexes like zinc ethylhexanoate,
  • Hydrocarbon resins in particular phenolic resins, especially as adhesive resins,
  • Mastication aids such as 2,2’-dibenzamidodiphenyldisulfide (DBD) and
  • Process aids in particular fatty acid esters and metal soaps, such as zinc soaps and/or calcium soaps,
  • mineral oil When using mineral oil, it is preferably selected from the group consisting of DAE (Destilled Aromatic Extracts), RAE (Residual Aromatic Extract), TDAE (Treated Destillated Aromatic Extracts), MES (Mild Extracted Solvents) and naphthenic oils.
  • DAE Destilled Aromatic Extracts
  • RAE Residual Aromatic Extract
  • TDAE Temporal Destillated Aromatic Extracts
  • MES Mild Extracted Solvents
  • the quantity of other additives in the total quantity is preferably 3 to 150 phr, particularly preferably 3 to 100 phr and most preferably 5 to 80 phr.
  • the rubber compound according to the invention is preferably used in vulcanized form, particularly in vehicle tires or other vulcanized technical rubber articles.
  • the vulcanization of the rubber compound according to the invention is preferably carried out in the presence of sulfur and/or sulfur donors using vulcanization accelerators, wherein some vulcanization accelerators can also act as sulfur donors.
  • the accelerator is selected from the group consisting of thiazole accelerators, mercapto accelerators, sulfenamide accelerators, thiocarbamate accelerators, thiuram accelerators, thiophosphate accelerators, thiohamperm accelerators, xanthate accelerators, and guanidine accelerators.
  • At least one sulfenamide accelerator is selected from the group consisting of N-cyclohexyl-2-benzothiazole sulfenamide (CBS), N,N-dicyclohexylbenzothiazole-2-sulfenamide (DCBS), benzothiazole-2-sulfene morpholide (MBS), N-tert-butyl-2-benzothiazole sulfenamide (TBBS), N-tert-butyl-2-benzothiazole sulfenimide (TBSI), and/or at least one guanidine accelerator, such as diphenylguanidine (DPG).
  • CBS N-cyclohexyl-2-benzothiazole sulfenamide
  • DCBS N,N-dicyclohexylbenzothiazole-2-sulfenamide
  • MVS benzothiazole-2-sulfene morpholide
  • TBBS N-tert-butyl-2-
  • sulfur-donating substance Any sulfur-donating substance known to experts can be used as the sulfur-donating substance.
  • one or more reversion protectants such as 1,6-bis(N,N-dibenzylthiocarbamoyldithio)hexane, hexamethylene-1,6-bis(thiosulfate) disodium salt dihydrate, and/or tetrabenzylthiuram disulfide (TBzTD), may be used in the rubber compound.
  • reversion protectants such as 1,6-bis(N,N-dibenzylthiocarbamoyldithio)hexane, hexamethylene-1,6-bis(thiosulfate) disodium salt dihydrate, and/or tetrabenzylthiuram disulfide (TBzTD)
  • vulcanization retarders may be present in the rubber compound.
  • the rubber compound is otherwise produced according to the standard procedure in the rubber industry, in which a base mixture containing all components except the vulcanization system (e.g., sulfur and vulcanization-influencing substances) is first produced in one or more mixing stages. The finished mixture is then produced by adding the vulcanization system in the mixing stages, preferably in the final stage.
  • the vulcanization system e.g., sulfur and vulcanization-influencing substances
  • the finished compound is further processed, for example, by extrusion or calendering, and formed into the desired shape.
  • the rubber compound according to the invention is particularly suitable for use in vehicle tires, especially pneumatic tires. Its application in all tire components is conceivable in principle, particularly and preferably in the tread and/or the sidewall, most preferably in the tread. In the case of a tread with a cap/base construction, the rubber compound according to the invention is preferably used at least in the cap.
  • the mixture is placed as a ready-made mixture into the appropriate shape, preferably a sidewall and/or a tread, before vulcanization and applied during the manufacture of the vehicle tire blank as is known.
  • the production of the rubber compound according to the invention for use as a body compound in vehicle tires is carried out as already described. The difference lies in the shaping after the extrusion process or the calendering of the compound. The resulting shapes of the still unvulcanized rubber compound for one or more different body compounds then serve to construct a tire blank.
  • body compound refers to the rubber compounds used for the other components of a tire, such as the horn profile, separating plate, inner liner (inner layer), core profile, belt, shoulder, belt profile, carcass, bead reinforcement, bead profile and bandage.
  • the extruded, still unvulcanized compound is formed into the appropriate shape and is often provided with reinforcing elements, e.g., synthetic fibers or steel cords, either during or after this process. Further processing is then carried out by vulcanization.
  • reinforcing elements e.g., synthetic fibers or steel cords
  • one object of the present invention is a vulcanizate obtained by sulfur vulcanization of at least one rubber compound according to the invention, including all preferred features.
  • Another object of the present invention is a vehicle tire comprising at least one component of at least one vulcanizate according to the invention, including all preferred features.
  • vehicle tires are understood to mean pneumatic vehicle tires and solid rubber tires, including tires for industrial and construction vehicles, truck, car and two-wheeler tires.
  • a preferred vehicle tire according to the invention comprises at least one vulcanizate according to the invention including all preferred features at least in the tread and/or the sidewall, particularly preferably at least in the tread.
  • another object of the present invention is the use of the sulfur-crosslinkable rubber compound according to the invention, including all preferred features, for the manufacture of technical rubber articles, such as bellows, conveyor belts, air springs, belts, straps or hoses, as well as shoe soles.
  • examples according to the invention are designated E1 and E2, and the comparative examples are designated V1 and V2. Furthermore, examples E10 and E20 according to the invention are disclosed in Table 3.
  • Sprintan SLR 3402 is a solution-polymerized styrene-butadiene copolymer with 15% styrene and 30% vinyl content.
  • BR500 is a butadiene rubber (BR) with a low cis content.
  • BR500 has a trans content of 49%, a cis content of 35%, and a vinyl content of 15%.
  • BR500 is functionalized and exhibits a high carbon black (soot) affinity.
  • BR511 is a low-cis butadiene rubber (BR). BR511 has a trans content of 37%, a cis content of 30%, and a vinyl content of 30%. BR511 is functionalized and exhibits a high affinity for silicon dioxide.
  • KBR820 is a low-cis butadiene rubber (BR). It has a cis content of 40.5% and a vinyl content of 12%. KBR820 is functionalized and exhibits a high affinity for silicon dioxide.
  • Silica 1 Zeosil® 1165MP, Solvay, mean CTAB surface area 157 m2/g, mean BET surface area 161 m2/g,
  • Silica 2 Premium SW, Solvay, average CTAB surface area 250 m2/g, average BET surface area 275 m2/g,
  • Silane 2 Bis-[3-(triethoxysilyl)-propyl] disulfide (TESPD, silane with 75% S2), Evonik Industries
  • Silane 3 3-Octanoylthio-1-propyltriethoxysilane, NXT, Momentive
  • the silane (according to formula A-X1) was produced as follows:
  • Na2CO3 (59.78 g; 0.564 mol) and an aqueous solution of NaSH (40% in water;
  • silane of formula B-Il 1,6-Bis(thiopropyltriethoxysilyl)hexane
  • NMR method The molar ratios and mass fractions given as analytical results in the examples above are derived from 13 C-NMR measurements with the following parameters: 100.6 MHz, 1000 scans, solvent CDCb, internal standard for calibration: tetramethylsilane, relaxation aid Cr(acac)s, a defined amount of dimethyl sulfone was used to determine the mass fraction in the product. It is added as an internal standard and the mass fraction is calculated from the molar ratios of the products.
  • the mixture was produced according to the procedure common in the rubber industry under normal conditions in 2-5 stages.
  • Test specimens were produced from all mixtures by vulcanization to t95 to t100 (measured on the Moving Die Rheometer according to ASTM D 5289-12/ ISO 6502) under pressure at 140-150 °C and material properties typical for the rubber industry were determined with these test specimens using the test procedures specified below.
  • Abrasion Relative weight loss of the respective tires after 15,000 km to 20,000 km of road driving at an average temperature of 5 to 10 °C.
  • the measured values are given as a percentage relative to the measured values of the comparison example V1. A higher percentage indicates better tire performance.
  • the rubber compounds according to the invention in particular compound E1, surprisingly result in a Significantly improved wet braking performance is achieved while maintaining at least the same or improved rolling resistance and wear behavior compared to V1.
  • rolling resistance and wear behavior can be significantly improved, and wet braking performance can be improved even further.
  • the tire according to E2 exhibits particularly advantageous abrasion and rolling resistance characteristics.
  • the rubber compounds according to the invention exhibit optimal processability, in particular mixability and extrudability.
  • the conflict of objectives arising from the aforementioned properties is resolved at a higher level by the rubber compound according to the invention.
  • E10 and E20 correspond to E1 and E2 (see Table 1) except that the proportion of BR was increased from 20 phr to 40 phr and the proportion of NR was decreased from 80 phr to 60 phr.

Landscapes

  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • 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)

Abstract

L'invention concerne un mélange de caoutchouc réticulable au soufre, le produit de vulcanisation du mélange de caoutchouc et un pneu de véhicule. Le mélange de caoutchouc contient au moins les constituants suivants : a) de 50 à 100 pce d'au moins un polyisoprène, b) de 0 à 50 pce d'au moins un caoutchouc butadiène, le caoutchouc butadiène ayant été fonctionnalisé pour une liaison de silice, c) de 20 à 100 pce d'au moins un dioxyde de silicium à grande surface de contact, d) de 1 à 30 pce de silanes choisis parmi au moins deux composés organosiliciés.
PCT/EP2025/058927 2024-04-22 2025-04-02 Mélange de caoutchouc réticulable au soufre, produit de vulcanisation du mélange de caoutchouc et pneu de véhicule Pending WO2025223798A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102024203747.8A DE102024203747A1 (de) 2024-04-22 2024-04-22 Schwefelvernetzbare Kautschukmischung, Vulkanisat der Kautschukmischung und Fahrzeugreifen
DE102024203747.8 2024-04-22

Publications (1)

Publication Number Publication Date
WO2025223798A1 true WO2025223798A1 (fr) 2025-10-30

Family

ID=95284585

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2025/058927 Pending WO2025223798A1 (fr) 2024-04-22 2025-04-02 Mélange de caoutchouc réticulable au soufre, produit de vulcanisation du mélange de caoutchouc et pneu de véhicule

Country Status (2)

Country Link
DE (1) DE102024203747A1 (fr)
WO (1) WO2025223798A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102016201195A1 (de) * 2016-01-27 2017-07-27 Continental Reifen Deutschland Gmbh Kautschukmischung und Fahrzeugreifen
DE102017221232A1 (de) 2017-11-28 2019-05-29 Continental Reifen Deutschland Gmbh Schwefelvernetzbare Kautschukmischung, Vulkanisat der Kautschukmischung und Fahrzeugreifen
WO2023104252A1 (fr) 2021-12-06 2023-06-15 Continental Reifen Deutschland Gmbh Mélange de caoutchouc réticulable au soufre, vulcanisat du mélange de caoutchouc, et pneu de véhicule
EP4079538B1 (fr) * 2021-04-14 2024-01-24 Continental Reifen Deutschland GmbH Mélange de caoutchouc réticulable au soufre, vulcanisat du mélange de caoutchouc et pneumatique de véhicule
EP4311690A1 (fr) * 2022-07-28 2024-01-31 The Goodyear Tire & Rubber Company Composition de caoutchouc pour pneu de camion

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102016201195A1 (de) * 2016-01-27 2017-07-27 Continental Reifen Deutschland Gmbh Kautschukmischung und Fahrzeugreifen
DE102017221232A1 (de) 2017-11-28 2019-05-29 Continental Reifen Deutschland Gmbh Schwefelvernetzbare Kautschukmischung, Vulkanisat der Kautschukmischung und Fahrzeugreifen
EP4079538B1 (fr) * 2021-04-14 2024-01-24 Continental Reifen Deutschland GmbH Mélange de caoutchouc réticulable au soufre, vulcanisat du mélange de caoutchouc et pneumatique de véhicule
WO2023104252A1 (fr) 2021-12-06 2023-06-15 Continental Reifen Deutschland Gmbh Mélange de caoutchouc réticulable au soufre, vulcanisat du mélange de caoutchouc, et pneu de véhicule
EP4311690A1 (fr) * 2022-07-28 2024-01-31 The Goodyear Tire & Rubber Company Composition de caoutchouc pour pneu de camion

Also Published As

Publication number Publication date
DE102024203747A1 (de) 2025-10-23

Similar Documents

Publication Publication Date Title
DE102015218745B4 (de) Kautschukmischung und Fahrzeugreifen
EP3150402B1 (fr) Compose caoutchouc et pneu de vehicule
EP3150401B1 (fr) Compose caoutchouc et pneu de vehicule
EP3150403B1 (fr) Compose caoutchouc et pneu de vehicule
WO2018033505A1 (fr) Mélange de caoutchouc réticulable au soufre et pneumatique de véhicule
WO2018033506A1 (fr) Mélange de caoutchouc réticulable au soufre et pneumatique de véhicule
DE102015218746A1 (de) Kautschukmischung und Fahrzeugreifen
WO2018033508A1 (fr) Mélange de caoutchouc réticulable au soufre et pneumatique de véhicule
WO2018033313A1 (fr) Mélange de caoutchouc, mélange caoutchouté réticulable au soufre et pneumatique de véhicule
EP4079538B1 (fr) Mélange de caoutchouc réticulable au soufre, vulcanisat du mélange de caoutchouc et pneumatique de véhicule
WO2023104252A1 (fr) Mélange de caoutchouc réticulable au soufre, vulcanisat du mélange de caoutchouc, et pneu de véhicule
WO2018033316A1 (fr) Mélange de caoutchouc, mélange de caoutchouc réticulable au soufre et pneumatique de véhicule
WO2019110176A1 (fr) Mélange de caoutchouc réticulable au soufre, vulcanisat de ce mélange de caoutchouc et pneu de véhicule
WO2018033500A1 (fr) Mélange de caoutchouc réticulable au soufre et pneumatique de véhicule
WO2025223798A1 (fr) Mélange de caoutchouc réticulable au soufre, produit de vulcanisation du mélange de caoutchouc et pneu de véhicule
DE102020208165A1 (de) Fahrzeugluftreifen
EP4423188B1 (fr) Composition de caoutchouc reticulable avec du soufre, vulcanisate de la-dite composition de caoutchouc et pneumatique
DE102019207526B4 (de) Schwefelvernetzbare Kautschukmischung, Vulkanisat und Verwendung in einem Fahrzeugreifen
DE102022212853A1 (de) Schwefelvernetzbare Kautschukmischung, Vulkanisat der Kautschukmischung und Fahrzeugreifen
DE102016201195A1 (de) Kautschukmischung und Fahrzeugreifen
DE102015216308B4 (de) Kautschukmischung, Verfahren zu deren Herstellung, Vulkanisat daraus und Verwendung zur Herstellung von Fahrzeugreifen
WO2022262913A1 (fr) Mélange de caoutchouc et pneu
DE102022210845A1 (de) Schwefelvernetzbare Kautschukmischung, Vulkanisat der Kautschukmischung und Fahrzeugreifen
WO2024199994A1 (fr) Mélange de caoutchoucs et pneu
WO2025176474A1 (fr) Procédé pour mélanger un mélange à base de caoutchouc

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 25716680

Country of ref document: EP

Kind code of ref document: A1