EP4408918A1 - Pneu de deux-roues, de préférence pneu de bicyclette, et procédé de production d'un pneu de deux-roues, de préférence un pneu de bicyclette - Google Patents

Pneu de deux-roues, de préférence pneu de bicyclette, et procédé de production d'un pneu de deux-roues, de préférence un pneu de bicyclette

Info

Publication number
EP4408918A1
EP4408918A1 EP22782847.2A EP22782847A EP4408918A1 EP 4408918 A1 EP4408918 A1 EP 4408918A1 EP 22782847 A EP22782847 A EP 22782847A EP 4408918 A1 EP4408918 A1 EP 4408918A1
Authority
EP
European Patent Office
Prior art keywords
tire
rubber
wheeler
particularly preferably
raw materials
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
EP22782847.2A
Other languages
German (de)
English (en)
Inventor
Rainer Kahner
Alexander Burkhart
Erin Klokkers
Thorsten Torbrügge
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 EP4408918A1 publication Critical patent/EP4408918A1/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • C08L9/06—Copolymers with styrene
    • 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
    • B60C2200/00—Tyres specially adapted for particular applications
    • B60C2200/12—Tyres specially adapted for particular applications for bicycles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2207/00—Properties characterising the ingredient of the composition
    • C08L2207/20—Recycled plastic
    • C08L2207/24—Recycled plastic recycling of old tyres and caoutchouc and addition of caoutchouc particles

Definitions

  • Two-wheeler tire preferably a bicycle tire
  • method for producing a two-wheeler tire preferably a bicycle tire
  • the invention relates to a two-wheeler tire, preferably a bicycle tire, and a method for producing a two-wheeler tire, preferably a bicycle tire.
  • two-wheeler tires in particular bicycle tires, have one or more components made from at least one rubber mixture, depending on the design.
  • WO 2016/105932 A1 discloses the use of vegetable oil and recycled rubber particles in the tread underplate of vehicle tires, with bicycle tires not being mentioned at all.
  • the present invention is based on the object of providing a two-wheeler tire, preferably a bicycle tire, which is composed more sustainably without having any losses in its properties with regard to the requirements in ferry operation.
  • the two-wheeler tire should not have any significant Have disadvantages in rolling resistance behavior or even have improved rolling resistance behavior.
  • the grip behavior in particular the wet grip behavior, and the abrasion behavior should not be significantly negatively affected.
  • the conflicting objectives of rolling resistance and wet grip should not be adversely affected.
  • the object is achieved by the two-wheel tire according to claim 1 and the method for producing a two-wheel tire according to claim 11.
  • the two-wheeler tire according to the invention preferably a bicycle tire, is characterized in that at least one component has a rubber mixture that contains at least one substance from renewable raw materials.
  • rubber mixture of the at least one component of the two-wheeler tire according to the invention is referred to below as “rubber mixture of the two-wheeler tire according to the invention” or even more briefly as “rubber mixture”.
  • the term “substance from renewable raw materials” is to be understood as meaning a substance which is materially produced from renewable raw materials as a source or is itself a raw material from renewable sources, plant sources being particularly preferred.
  • the substance from renewable raw materials is not rubber, and thus in particular not natural rubber. This means that, regardless of the rubber selected, it contains at least one substance from renewable raw materials that is not rubber.
  • the rubber mixture of the two-wheeler tire according to the invention thus contains at least one substance from renewable raw materials and optionally also natural rubber as rubber.
  • the bicycle tire according to the invention has the advantage that it is composed more sustainably and at the same time has no disadvantages in terms of its physical properties.
  • the two-wheeler tire according to the invention has no significant disadvantages or even an improvement in the rolling resistance behavior, while the other properties, in particular the grip, especially wet grip, and abrasion behavior remain at a comparable level.
  • the two-wheeler tire according to the invention thus even shows an improvement in the conflicting goals of rolling resistance behavior and abrasion behavior as well as rolling resistance behavior and wet grip behavior.
  • the method according to the invention is characterized by greater sustainability and provides the two-wheeler tire according to the invention, which is surprisingly distinguished by an improvement in the stated conflicting goals of rolling resistance behavior and abrasion behavior as well as rolling resistance behavior and wet grip behavior.
  • the two-wheeler tire according to the invention and the method according to the invention thus enable a smaller CO2 footprint while at the same time improving performance.
  • All advantageous configurations which are reflected in the patent claims, among other things, are included in the invention.
  • the invention also includes configurations that result from the combination of different features of different gradations when these features are preferred, so that a combination of a first feature referred to as “preferred” or a feature described in the context of an advantageous embodiment with a further feature, e.g. B. "particularly preferred" designated feature is covered by the invention.
  • the specification phr (parts per hundred parts of rubber by weight) used in this document is the quantity specification for compound formulations customary in the rubber industry.
  • the dosage of the parts by weight of the individual substances is based on 100 parts by weight of the total mass of all high molecular weight (weight average molecular weight distribution Mw according to GPC greater than 60,000 g/mol) and therefore solid rubbers present in the mixture.
  • a two-wheeler tire is preferred, with the substance made from renewable raw materials being a plasticizer made from renewable raw materials. As a result, a particularly good rolling resistance behavior of the rubber mixture and thus of the two-wheeler tire is achieved with other properties remaining the same.
  • the plasticizer from renewable raw materials is particularly preferably a vegetable oil.
  • the vegetable oil can be any vegetable oil known to a person skilled in the art.
  • the vegetable oil is particularly preferably selected from the group consisting of rapeseed oil and sunflower oil, with rapeseed oil being particularly preferred.
  • the rubber mixture preferably contains a plasticizer from renewable raw materials, particularly preferably rapeseed oil, in amounts of 5 to 60 phr, particularly preferably 15 to 50 phr, very particularly preferably 15 to 30 phr.
  • a two-wheeler tire is also preferred, with the substance made from renewable raw materials being a filler made from renewable raw materials.
  • the filler is silica produced from renewable raw materials from rice husk ash.
  • the rubber mixture preferably contains a filler made from renewable raw materials, particularly preferably silica produced from rice husk ash, in amounts of 5 to 150 phr, particularly preferably 20 to 100 phr, very particularly preferably 30 to 70 phr.
  • a filler made from renewable raw materials particularly preferably silica produced from rice husk ash, in amounts of 5 to 150 phr, particularly preferably 20 to 100 phr, very particularly preferably 30 to 70 phr.
  • rice husk ash silica is also known to those skilled in the art as “rice husk ash silica” (RHAS).
  • silica that is obtained from the inorganic combustion residues (ash) of rice husks.
  • the ash obtained from rice husks has a comparatively high proportion of silica, at more than 80% by weight, and is therefore particularly suitable for extracting silica.
  • the silica produced from rice husk ash contained in the rubber mixture of the two-wheeler tire according to the invention preferably has a nitrogen surface area (BET surface area) (according to DIN ISO 9277 and DIN 66132) of 35 to 400 m 2 /g, particularly preferably 35 to 350 m 2 /g, most preferably from 75 to 320 m 2 /g and again most preferably from 120 to 235 m 2 /g, and a CTAB surface area (according to ASTM D 3765) from 30 to 400 m 2 /g, more preferably from 30 to 330 m 2 /g, most preferably from 70 to 300 m 2 /g and again most preferably from 110 to 230 m 2 /g.
  • BET surface area nitrogen surface area
  • a suitable silica produced from rice husk ash with a BET surface area of 155 m 2 /g and a CTAB surface area of 156 to 157 m 2 /g is available, for example, under the trade name "Precipitated Silica K160" from FengHai (PanJin) Rice Biotechnology Co.,Ltd available.
  • a two-wheeler tire is also preferred, the rubber mixture containing a tree resin as a substance from renewable raw materials.
  • the tree resin is a rosin resin.
  • the rubber mixture preferably contains 0.5 to 20 phr, particularly preferably 1 to 10 phr, very particularly preferably 1 to 5 phr of tree resin, preferably rosin.
  • the rubber mixture contains a plasticizer made from renewable raw materials, preferably vegetable oil, particularly preferably rapeseed oil, and a filler made from renewable raw materials, preferably silica produced from rice husk ash.
  • a plasticizer made from renewable raw materials preferably vegetable oil, particularly preferably rapeseed oil
  • a filler made from renewable raw materials preferably silica produced from rice husk ash.
  • Such a two-wheeler tire is characterized in that, due to the plasticizer and the filler, it is composed of a comparatively high proportion by mass of renewable raw materials and is therefore sustainable.
  • the two-wheeler tire surprisingly has improved rolling resistance behavior with other properties remaining the same, such as abrasion and wet grip behavior.
  • a two-wheeler tire is also preferred, the rubber mixture containing a plasticizer made from renewable raw materials, preferably vegetable oil, particularly preferably rapeseed oil, and a filler made from renewable raw materials, preferably silica produced from rice husk ash, and a tree resin, preferably colophony resin.
  • a plasticizer made from renewable raw materials, preferably vegetable oil, particularly preferably rapeseed oil
  • a filler made from renewable raw materials preferably silica produced from rice husk ash
  • a tree resin preferably colophony resin
  • Such a two-wheeler tire is characterized by the fact that it is comparatively high due to the plasticizer and the filler as well as the resin Mass proportion of renewable raw materials and is therefore composed sustainably.
  • the two-wheeler tire surprisingly has improved rolling resistance behavior with other properties remaining the same, such as abrasion and wet grip behavior.
  • a two-wheeler tire is also preferred, the rubber mixture additionally containing at least one recycled substance.
  • a “recycled substance” is to be understood as meaning a substance that is obtained by the reprocessing of waste, ie manufactured and used articles, or of new articles, ie articles which have been manufactured but not yet used.
  • rubber-containing waste is particularly preferred, such as used tires in particular.
  • New items are items that were manufactured from raw materials as part of a value chain by specifically modifying them, but were not subsequently used. This can in particular be rejects.
  • the recycled substance is reclaimed rubber.
  • Regenerated rubber (regenerated rubber or reclaim) is obtained from sulphur-crosslinked rubber vulcanizates by splitting the sulfur bridges, with the rubber mixtures being converted from the elastic to the plastic state by the devulcanization that takes place (devulcanized rubber mixtures).
  • Such a regenerated rubber product has an average particle size of 1 ⁇ m to 3 mm, preferably 1 ⁇ m to 1 mm and particularly preferably 1 ⁇ m to 100 ⁇ m, and thus has comparatively fine particles.
  • the average particle size is determined using a light microscope.
  • regenerated rubber also includes the use of various regenerated rubbers, unless otherwise stated or unless otherwise indicated.
  • All vulcanized rubber items are included as starting materials for the regenerated rubber, such as, for example and preferably, the sulfur-crosslinked rubber vulcanizates from used tires or conveyor belts or from vulcanized waste occurring in the production of technical rubber items or pneumatic vehicle tires.
  • one or more crushing steps often take place before the actual regeneration process, as a result of which vulcanized rubber granulate or vulcanized rubber powder or flour is obtained.
  • a two-wheeler tire is also preferred, the rubber mixture containing a plasticizer made from renewable raw materials, preferably vegetable oil, particularly preferably rapeseed oil, and a filler made from renewable raw materials, preferably silica produced from rice husk ash, and a tree resin, preferably colophony resin, and at least one recycled substance , preferably regenerated rubber contains.
  • a plasticizer made from renewable raw materials, preferably vegetable oil, particularly preferably rapeseed oil
  • a filler made from renewable raw materials preferably silica produced from rice husk ash
  • a tree resin preferably colophony resin
  • at least one recycled substance preferably regenerated rubber contains.
  • Such a two-wheeler tire is characterized in that it is made up of a comparatively high proportion by mass of the plasticizer and the filler as well as the resin and the recycled substance in a sustainable manner.
  • the two-wheeler tire has a surprisingly improved rolling resistance behavior with other properties remaining the same, such as abrasion and wet grip behavior.
  • the rubber mixture of the two-wheeler tire contains at least one rubber.
  • the rubber mixture of the two-wheeler tire according to the invention preferably contains at least one rubber which is selected from diene rubbers and rubbers with a saturated polymer chain, in particular a saturated main chain.
  • the diene rubber is preferably selected from the group consisting of natural polyisoprene (NR), synthetic polyisoprene (IR), butadiene rubber (BR), styrene-butadiene rubber (SBR).
  • the saturated polymer chain rubber is preferably ethylene propylene diene rubber (EPDM).
  • the rubber mixture of the two-wheeler tire particularly preferably contains at least one diene rubber, which is preferably selected from the group consisting of natural polyisoprene (NR), synthetic polyisoprene (IR), butadiene rubber (BR), styrene-butadiene rubber (SBR).
  • NR natural polyisoprene
  • IR synthetic polyisoprene
  • BR butadiene rubber
  • SBR styrene-butadiene rubber
  • the rubber mixture preferably contains at least one natural polyisoprene, preferably in amounts of 2 to 100 phr, and according to a particularly advantageous embodiment of the invention 5 to 35 phr, very particularly preferably 20 to 30 phr. This achieves particularly good processability of the rubber mixture according to the invention and optimized tear properties.
  • the rubber mixture preferably contains at least one polybutadiene (butadiene rubber), specifically preferably in amounts of 2 to 100 phr, and according to a particularly advantageous embodiment of the invention 5 to 35 phr, very particularly preferably 20 to 30 phr. This achieves particularly good abrasion and tear properties and good processability with low hysteresis loss of the rubber mixture according to the invention.
  • the rubber mixture contains at least one styrene-butadiene rubber (SBR), preferably in amounts of 2 to 100 phr, and according to a particularly advantageous embodiment of the invention 25 to 90 phr, very particularly preferably 40 to 60 phr. This achieves good processability with low hysteresis loss and good abrasion and tear properties of the rubber mixture according to the invention.
  • SBR styrene-butadiene rubber
  • the SBR is preferably an SSBR, resulting in optimized hysteresis properties.
  • the rubber mixture preferably contains a polymer blend of two or more, in particular three, of the rubbers mentioned NR, BR and SBR, preferably SSBR, the sum of all the rubbers present being 100 phr.
  • the natural and/or synthetic polyisoprene of all embodiments can be either cis-1,4-polyisoprene or 3,4-polyisoprene. However, preference is given to using cis-1,4-polyisoprenes with a cis-1,4 content>90% by weight. On the one hand, such a polyisoprene can be obtained by stereospecific polymerization in solution with Ziegler-Natta catalysts or using finely divided lithium alkyls. On the other hand, natural rubber (NR) is a cis-1,4-polyisoprene in which the cis-1,4 content in the natural rubber is greater than 99% by weight.
  • a mixture of one or more natural polyisoprenes with one or more synthetic polyisoprene(s) is also conceivable.
  • natural rubber means naturally occurring rubber that can be obtained from Hevea rubber trees and "non-Hevea” sources.
  • Non-Hevea sources include guayule shrubs and dandelions such as TKS (Taraxacum kok-saghyz; Russian dandelion).
  • a low-cis polybutadiene is, for example, Li-BR (lithium-catalyzed butadiene rubber) with a cis content of 20 to 50% by weight. Particularly good abrasion properties and low hysteresis of the rubber compound are achieved with a high-cis BR.
  • the polybutadiene(s) used can/can be end-group-modified with modifications and functionalizations and/or functionalized along the polymer chains.
  • the modification can involve those with hydroxyl groups and/or ethoxy groups and/or epoxy groups and/or siloxane groups and/or amino groups and/or aminosiloxane and/or carboxy groups and/or Act phthalocyanine groups and / or silane sulfide groups.
  • functionalizations further modifications known to the person skilled in the art, also referred to as functionalizations, are also possible.
  • Metal atoms can be part of such functionalizations.
  • styrene-butadiene rubber styrene-butadiene copolymer
  • SSBR solution-polymerized styrene-butadiene rubber
  • ESBR emulsion-polymerized styrene-butadiene rubber
  • the styrene-butadiene copolymer used can be end-group-modified with the modifications and functionalizations mentioned above for polybutadiene and/or functionalized along the polymer chains.
  • the rubber mixture of the two-wheeler tire according to the invention can also contain at least one filler which is not a substance from renewable raw materials and is preferably selected from the group consisting of carbon blacks and other silicas which are not produced from rice hull ash.
  • the terms “silica” and “silicic acid” are used synonymously in the context of the present invention.
  • the additional silicic acid can be the types of silicic acid known to those skilled in the art which are suitable as fillers for tire rubber mixtures.
  • a finely divided, precipitated silica which has a nitrogen surface area (BET surface area) (according to DIN ISO 9277 and DIN 66132) from 35 to 400 m 2 /g, preferably from 35 to 350 m 2 / g, more preferably from 85 to 320 m 2 / g and most preferably from 120 to 235 m 2 / g, and a CTAB surface area (according to ASTM D 3765) from 30 to 400 m 2 / g, preferably from 30 to 330 m 2 /g, more preferably from 80 to 300 m 2 /g and most preferably from 115 to 200 m 2 /g.
  • BET surface area nitrogen surface area
  • CTAB surface area accordinging to ASTM D 3765
  • Such silicas lead z. B. in rubber mixtures for tire treads to particularly good physical properties of the vulcanizates.
  • advantages in compound processing can result from a reduction in mixing time with the same product properties, which lead to improved productivity.
  • silicas z. B. both those of the type U Itrasil® VN3 (trade name) from Evonik and highly dispersible silicas, so-called HD silicas (e.g. Zeosil® 1165 MP from Solvay), can be used.
  • the rubber mixture contains 5 to 150 phr, particularly preferably 20 to 100 phr, of at least one further silica. This allows the properties of the rubber compound to be adjusted individually and the additional silica and the silica produced from rice hull ash to be metered in flexibly.
  • the rubber compound contains up to 10 phr of additional silica that is not made from rice hull ash.
  • the rubber mixture contains no further silica, ie 0 phr silica and is therefore free from silica which is not produced from rice hulls. In this way, optimal properties are achieved and the addition of further silica is saved as a process step.
  • the rubber mixture preferably contains silica produced from rice husk ash as a filler, preferably in amounts of 5 to 150 phr, particularly preferably 20 to 100 phr, very particularly preferably 30 to 70 phr.
  • silica from rice husk ash as the main filler and in particular to completely or at least partially replace “conventional” silicic acid, ie silica that is not made from rice husk ash.
  • silica from rice husk ash has an advantageous profile of properties, which is shown in particular in two-wheeler tires according to the invention, in particular bicycle tires, by an improvement in the conflicting goals.
  • the rubber mixture preferably contains 1 to 20 phr, particularly preferably 3 to 10 phr, of at least one carbon black.
  • Suitable carbon blacks are all types of carbon black known to those skilled in the art.
  • the carbon black has an iodine number, according to ASTM D 1510, which is also referred to as the iodine adsorption number, between 30 and 250 g/kg, preferably 30 to 180 g/kg, particularly preferably 40 to 180 g/kg, and very particularly preferably 70 to 130 g/kg, and a DBP number according to ASTM D 2414 of 30 to 200 ml/100 g, preferably 70 to 200 ml/100 g, particularly preferably 90 to 160 ml/100 g.
  • ASTM D 1510 which is also referred to as the iodine adsorption number
  • the DBP number according to ASTM D 2414 determines the specific absorption volume of a carbon black using dibutyl phthalate.
  • the rubber mixture can also contain at least one plasticizer that is not a substance from renewable raw materials and is preferably selected from the group consisting of mineral oils, phosphoric acid esters such as tri-(2-ethylhexyl) phosphate, and liquid rubbers with a weight-average molecular weight distribution Mw according to GPC of 60,000 g/mol or less.
  • mineral oil this is preferably selected from the group consisting of DAE (Distilled Aromatic Extracts), RAE (Residual Aromatic Extract), TDAE (Treated Distillated Aromatic Extracts), MES (Mild Extracted Solvents), white oils and naphthenic oils, where RAE is particularly preferred.
  • the rubber mixture contains 5 to 60 phr, particularly preferably 15 to 50 phr, very particularly preferably 15 to 30 phr of at least one mineral oil softener, preferably RAE.
  • the rubber compound contains no mineral oil softener, i.e. 0 phr mineral oil softener.
  • the rubber mixture preferably contains a plasticizer from renewable raw materials, particularly preferably rapeseed oil, in amounts of 5 to 60 phr, particularly preferably 15 to 50 phr, very particularly preferably 15 to 30 phr.
  • the rubber mixture can contain customary additives in customary parts by weight, which are preferably added in at least one basic mixing stage during its production.
  • additives include a) antioxidants such.
  • 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
  • triazines such as 2-N,4-N,6-N-tris[4-(5-methylhexan-2-ylamino)phenyl]- 1,3,5-triazine-2,4,6-triamine (PPD triazine) and/or dihydroquinolines, such as 2,2,4-trimethyl-1,2-dihydroquinoline (TMQ), and N-phenyl-1-naphthylamine (PAN), 2,2'-methylenebis(4-methyl-6-tert-butylphenol) (BKF), butylated
  • activators such as. B. zinc oxide and fatty acids (e.g. stearic acid) and/or other activators such as zinc complexes such as zinc ethylhexanoate, c) activators and/or agents for binding fillers, in particular carbon black, such as S-(3-aminopropyl)thiosulfuric acid and/or their metal salts (binding to carbon black) and silane coupling agents (binding to silicic acid or silica), d) antiozonant waxes, e) resins, in particular adhesive resins, f) mastication aids, such as e.g.
  • processing aids such as in particular fatty acid esters and metal soaps, such as zinc soaps and / or calcium soaps, and / or polyethylene glycols
  • colorants in particular pigments based on titanium dioxide (TiÜ2), optionally in combination with color pigments.
  • the rubber mixture preferably contains at least one antiaging agent which is selected from the group consisting of
  • N-phenyl-N'-(1,3-dimethylbutyl)-p-phenylenediamine (6PPD) and N,N'-ditolyl-p-phenylenediamine (DTPD).
  • the rubber mixture of the two-wheeler tire according to the invention preferably contains at least one silane coupling agent.
  • the silane coupling agents can be of any type known to those skilled in the art.
  • the rubber mixture can thus contain a mixture of different silanes.
  • the silane coupling agents react with the surface silanol groups of the silicic acid or silica or other polar groups during the mixing of the rubber or the rubber mixture (in situ) or even before the filler is added to the rubber in the sense of a pretreatment (premodification).
  • Coupling agents known from the prior art are bifunctional organosilanes which have at least one alkoxy, cycloalkoxy or phenoxy group as a leaving group on the silicon atom and which have a group as another functionality which, after cleavage, can undergo a chemical reaction with the double bonds of the polymer.
  • the latter group can be z.
  • Blocked mercaptosilanes as z. B. are known from WO 99/09036, can be used as a silane coupling agent.
  • Silanes as described in WO 2008/083241 A1, WO 2008/083242 A1, WO 2008/083243 A1 and WO 2008/083244 A1, can also be used.
  • the rubber mixture of the two-wheeler tire according to the invention particularly preferably contains at least one silane coupling agent which is selected from the group consisting of 3,3'-bis(triethoxysilylpropyl) disulfide (TESPD), 3,3'-bis(triethoxysilylpropyl) tetrasulfide (TESPT) and 3-Octanoylthio-1-propyltriethoxysilane, TESPD is very particularly preferred.
  • TESPD 3,3'-bis(triethoxysilylpropyl) disulfide
  • TESPT 3,3'-bis(triethoxysilylpropyl) tetrasulfide
  • 3-Octanoylthio-1-propyltriethoxysilane TESPD is very particularly preferred.
  • the proportion of the total amount of further additives is preferably 3 to 150 phr, particularly preferably 5 to 100 phr and very particularly preferably 20 to 85 phr, again preferably 35 to 85 phr.
  • Zinc oxide (ZnO) may be included in the total amount of the other additives. This can be any type of zinc oxide known to those skilled in the art, such as ZnO granules or powder.
  • the conventionally used zinc oxide usually has a BET surface area of less than 10 m 2 /g. However, a zinc oxide with a BET surface area of 10 to 100 m 2 /g, such as so-called “nano-zinc oxides”, can also be used.
  • the two-wheeler tire according to the invention is preferably vulcanized.
  • the rubber mixture is also preferably vulcanized.
  • the vulcanization of the rubber mixture is preferably carried out in the presence of sulfur and/or sulfur donors with the aid of vulcanization accelerators, it being possible for some vulcanization accelerators to 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, thiourea accelerators, xanthogenate accelerators and guanidine accelerators.
  • a sulfenamide accelerator selected from the group consisting of N-cyclohexyl-2-benzothiazole sulfenamide (CBS), N,N-dicyclohexylbenzothiazole-2-sulfenamide (DCBS), benzothiazyl-2-sulfenemorpholide (MBS), N- tert-butyl-2-benzothiazylsulfenamide (TBBS) and guanidine accelerators such as diphenylguanidine (DPG).
  • CBS N-cyclohexyl-2-benzothiazole sulfenamide
  • DCBS N,N-dicyclohexylbenzothiazole-2-sulfenamide
  • MVS benzothiazyl-2-sulfenemorpholide
  • TBBS N- tert-butyl-2-benzothiazylsulfenamide
  • DPG diphenylguanidine
  • the two-wheeler tire according to the invention is preferably a bicycle tire, in particular a pneumatic bicycle tire or a tubeless bicycle tire or a solid rubber tire for bicycles, preferably a pneumatic bicycle tire.
  • the present invention has succeeded in providing bicycle tires that have a surprising improvement in the conflicting objectives of rolling resistance behavior and abrasion behavior as well as rolling resistance behavior and wet grip behavior.
  • the improvement is also particularly surprising because, as explained above, the conflicting goals mentioned are aggravated precisely in the case of bicycle tires—due to the lower operating temperature as the reference temperature for the rolling resistance.
  • a bicycle tire according to the invention is preferred which is a bicycle tire with a width of preferably 20 to 150 mm, particularly preferably 25 to 100 mm, very particularly preferably 25 to 70 mm and/or an inner diameter of the tire casing of preferably 340 to 640 mm. particularly preferably 550 to 630 mm, very particularly preferably 570 to 620 mm.
  • the "width" is the width of the tire casing across the direction of rotation.
  • the two-wheeler tire according to the invention is a bicycle tire according to the definition according to ETRTO (“European Tire and Rim Technical Organization”).
  • the bicycle tire is a racing bike tire, a city trekking, gravel or cargo bike tire, or a mountain bike tire or a solid rubber tire.
  • the two-wheeler tire is a pneumatic two-wheeler tire, preferably a pneumatic bicycle tire, particularly preferably a racing bike tire, a city trekking, gravel or cargo bike tire, or mountain bike tire, with a tread, a tire carcass, tire side walls and in each axial half of the tire a bead area with a tire bead with a core, wherein the pneumatic bicycle tire in the bead areas is one axially outside of the carcass arranged protective layer with reinforcements embedded in rubber material, wherein the tire carcass is formed from a first carcass ply and a second carcass ply each having reinforcements, wherein the second carcass ply is arranged in a zenith of the two-wheel pneumatic tire radially inside the first carcass ply and extends from the zenith of the two-wheel pneumatic tire over the tire sidewalls extend into both bead areas and there wraps around the respective core from axially inside to axially outside and ends
  • a two-wheeler tire is also preferred, the component being at least the tread and/or the cap and/or the base of a tread with a cap-base structure and/or a puncture protection layer and/or a damping layer and/or at least one sidewall and/or at least one carcass ply.
  • the method according to the invention for producing a two-wheeler tire comprises at least the following method steps:
  • step B) shaping the rubber mixture from step A) into a component of a two-wheeler tire
  • step C) introducing the component from step B) onto or into a green tire; D) Vulcanization of the green tire from step C)
  • steps A) to D) are carried out in a manner known to those skilled in the art using devices known to those skilled in the art.
  • the rubber mixture is produced according to the process customary in the rubber industry, in which a basic mixture with all the components apart from the vulcanization system (e.g. sulfur and substances that influence vulcanization) is first produced in one or more mixing stages.
  • the finished mixture is produced by adding the vulcanization system in a final mixing stage.
  • the finished mixture is processed further, e.g. by an extrusion process or calendering, and brought into the appropriate form, preferably in the form of a tread strip.
  • Tables 1 and 2 summarize the results of laboratory tests on the rubber mixture of the two-wheeler tire according to the invention and the results of tire tests.
  • the examples marked with “E” are according to the invention, while those marked with “V” represent comparative examples.
  • the mixtures on which the tire tests in Table 2 are based are comparable to those in the laboratory tests from Table 1, so that only the essential components are shown in Table 2 to better explain the invention.
  • the mixtures containing regrind also have an increased amount of sulfur and accelerators.
  • the mixtures were used as treads.
  • the tires were city trekking tires and had a tread width of 42 mm and an inner diameter of 622 mm.
  • the preparation of the mixture was otherwise carried out according to the Rubber industry standard process under standard conditions in two stages in a laboratory mixer with a volume of 300 milliliters to 3 liters, in which initially in the first mixing stage (basic mixing stage) all the components except for the vulcanization system (sulphur and vulcanization-influencing substances) are mixed for 200 to 600 seconds at 140 to 165 °C, target temperatures from 140 to 157 °C.
  • the ready-to-use mixture was produced by adding the vulcanization system in the second stage (ready-to-mix stage), with mixing at 90 to 120° C. for 180 to 300 seconds.
  • Test specimens were produced from all the mixtures by vulcanization according to t95 to t100 (measured on a moving die rheometer according to ASTM D 5289-12/ISO 6502) under pressure at 160°C and material properties typical of the rubber industry were determined with these test specimens using the test methods given below .
  • Rapeseed oil RAPESEED OIL STANDARD , Biona Jerzin sro e) indene-coumarone resin: Novares C 30, Rain Carbon Germany GmbH f) colophony resin: Tyreon-160, Orgkhim g) activators: 3 phr each of zinc oxide and 2 phr of stearic acid h) silane : TESPD
  • the examples according to the invention are characterized by improved rolling resistance indicators, while abrasion and wet grip remain at a comparable level, the latter being particularly evident from the tire tests in Table 2.
  • results were determined based on the torque method of the ISO 28580 standard at 22 °C.
  • a drum diameter of 800 mm, a load of 50 kg and a speed of 30 km/h were used.
  • the abrasion according to Table 3 is an abrasion according to DIN ISO 4649 with the modification "half load” (5 N instead of 10 N contact force).
  • Table 3 compares mixture examples without regrind.
  • the data from the tire tests show, among other things, improved properties in terms of rolling resistance.
  • these results of a two-wheeler tire according to the invention, in particular a bicycle tire show an improvement in the conflicting objectives of rolling resistance behavior and abrasion behavior as well as rolling resistance behavior and wet grip behavior.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Tires In General (AREA)

Abstract

L'invention concerne un pneu de deux-roues, de préférence un pneu de bicyclette, et un procédé de fabrication d'un pneu de deux-roues, de préférence un pneu de bicyclette. Le pneu de deux-roues contient dans au moins un de ses composants un mélange de caoutchoucs qui contient au moins les éléments suivants : au moins un caoutchouc, de préférence au moins un caoutchouc diénique ; et au moins une substance issue de matières premières renouvelables autres que le caoutchouc.
EP22782847.2A 2021-09-30 2022-09-20 Pneu de deux-roues, de préférence pneu de bicyclette, et procédé de production d'un pneu de deux-roues, de préférence un pneu de bicyclette Pending EP4408918A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102021211028.2A DE102021211028A1 (de) 2021-09-30 2021-09-30 Zweiradreifen, bevorzugt Fahrradreifen, und Verfahren zur Herstellung eines Zweiradreifens, bevorzugt eines Fahrradreifens
PCT/DE2022/200219 WO2023051882A1 (fr) 2021-09-30 2022-09-20 Pneu de deux-roues, de préférence pneu de bicyclette, et procédé de production d'un pneu de deux-roues, de préférence un pneu de bicyclette

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EP4408918A1 true EP4408918A1 (fr) 2024-08-07

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US (1) US20250018745A1 (fr)
EP (1) EP4408918A1 (fr)
CN (1) CN117980393A (fr)
DE (1) DE102021211028A1 (fr)
WO (1) WO2023051882A1 (fr)

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US20240158615A1 (en) * 2022-11-02 2024-05-16 The Goodyear Tire & Rubber Company Precipitated silica pretreated with a coupling agent and polyethylene glycol for a rubber composition

Family Cites Families (15)

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Publication number Priority date Publication date Assignee Title
JP2001505225A (ja) 1997-08-21 2001-04-17 シーケイ・ウイトコ・コーポレーション 充填材含有ゴム用保護化メルカプトシラン・カップリング剤
AU2003255474A1 (en) * 2002-09-04 2004-03-29 Michelin Recherche Et Technique S.A. Rubber composition for tyre treads
US7968634B2 (en) 2006-12-28 2011-06-28 Continental Ag Tire compositions and components containing silated core polysulfides
US7968636B2 (en) 2006-12-28 2011-06-28 Continental Ag Tire compositions and components containing silated cyclic core polysulfides
US7968635B2 (en) 2006-12-28 2011-06-28 Continental Ag Tire compositions and components containing free-flowing filler compositions
US7968633B2 (en) 2006-12-28 2011-06-28 Continental Ag Tire compositions and components containing free-flowing filler compositions
DE102008055472A1 (de) * 2008-12-02 2010-06-10 Continental Reifen Deutschland Gmbh Kautschuckmischung und Reifen
JP2011174048A (ja) * 2010-01-27 2011-09-08 Sumitomo Rubber Ind Ltd 二輪車用タイヤのトレッド用ゴム組成物及び二輪車用タイヤ
WO2011123406A1 (fr) * 2010-03-31 2011-10-06 Michelin Recherche Et Technique S.A. Pneu à faible hystérésis
FR2980481B1 (fr) * 2011-09-26 2013-10-11 Michelin Soc Tech Pneumatique a adherence amelioree sur sol mouille
WO2013093752A1 (fr) * 2011-12-20 2013-06-27 Pirelli Tyre S.P.A. Pneu d'hiver
EP3224315B1 (fr) * 2014-11-28 2021-10-27 Compagnie Générale des Etablissements Michelin Composition de caoutchouc
JP5841225B1 (ja) * 2014-12-12 2016-01-13 株式会社ブリヂストン タイヤ
US10227479B2 (en) 2014-12-23 2019-03-12 Bridgestone Americas Tire Operations, Llc Rubber composition and tire comprising sustainable resources and related methods
IT201800005915A1 (it) * 2018-05-31 2019-12-01 Pneumatici per veicoli e composizioni elastomeriche per pneumatici comprendenti particolari silici da cenere di lolla di riso

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DE102021211028A1 (de) 2023-03-30
WO2023051882A1 (fr) 2023-04-06
US20250018745A1 (en) 2025-01-16
CN117980393A (zh) 2024-05-03

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