Amine derivatives as an additive in rubbers

Abstract

The present invention relates to the use of amine derivatives as additives in rubbers for improving the properties of vehicle tires.

Description

Amine derivatives as additives in rubbers Description The present invention relates to the use of various amine derivatives as additives in rubbers to improve the properties of vehicle tires. Modern vehicle tires are subject to increased demands on their properties, not least from a sustainability perspective, in particular low rolling resistance to reduce fuel consumption and associated emissions, and high abrasion resistance to reduce the emission of tire wear into the environment and increase the service life of the tires without simultaneously impairing the grip of the tires on the surface under various conditions (e.g. temperature, weather conditions, road conditions). To improve these properties, vehicle tires can contain various fillers and vulcanization accelerators in their rubber compounds. These fillers are often inorganic materials such as carbon black, silicates, or zinc oxide, while the rubbers themselves are non-polar polymers. Therefore, the miscibility and compatibility of these components is often poor due to their different polarities. Other additives, such as vulcanization accelerators and activators, antioxidants, and plasticizers, require uniform distribution within the rubber to ensure their effectiveness. There is therefore a need for additives that can be used to better incorporate filler materials such as carbon black, silicates or zinc oxide, as well as the other additives mentioned, into rubbers and to fulfil the functions in the rubbers or during their production, for example as antioxidants, activators or plasticizers. Furthermore, silanes are often used as processing aids in the production of rubber compounds for tires to improve the mixing of carbon black or silica. These release alcohols, particularly ethanol, during the process. This represents an emission that must be avoided or reduced for occupational health and safety and environmental reasons. US 2008 / 0214718 A1 describes the use of polyisobutene derivatives for dispersing metal oxides, such as ZnO, in polymers, e.g., polychloroprene, urethane-acrylic, or acrylic latices. Examples of such polyisobutene derivatives are reaction products of polyisobutenyl-substituted succinic acid (PIBSA) with polyamines, such as triethylenetetraamine, for hydrophobizing zinc oxide in dispersions. Applications in rubber are not described. Rubber differs from the dispersions described simply in that it is a continuous hydrophobic and organic matrix, whereas in dispersions aqueous and organic phases alternate and are separated from each other by phase boundaries. The problem was solved by using amine derivatives of the formula wherein X is a single bond or an organic spacer, R 1a straight-chain or branched alkenyl radical having a molecular weight Mn of 104 to 100,000 g / mol, preferably of 104 to 10,000 g / mol, particularly preferably of 156 to 5,000 g / mol and very particularly preferably of 500 to 2,500 g / mol R 2 and R 3 independently of each other, another single bond to the organic spacer X, hydrogen, Ci- to C4-alkyl, a group -R-NR 4 R 5 or a repeating residue -[-R-NH-] X -H x is a positive integer from 1 to 4 R is a divalent organic radical having 2 to 6 carbon atoms, which may optionally be oxygen atoms, preferably selected from the group consisting of 1,2-ethylene, 1,2- Propylene and 1,3-propylene, R 4 and R 5 independently hydrogen or Ci- to C lkyl is to improve at least one of the following properties - Dispersion coefficient - particle size - Wet grip - Abrasion resistance - Rolling resistance -Vulcanization speed of rubber-containing tires. In a preferred embodiment, the spacer X comprises a structural unit of the formula or respectively, wherein the bonding sites are each connected to the nitrogen atom and the radical R 1 are connected. In another preferred embodiment, the spacer X is a single bond. For the remainder R 1 it is a straight-chain or branched, preferably branched alkenyl radical having a molecular weight Mn of 104 to 100,000 g / mol, preferably of 104 to 10,000 g / mol, particularly preferably of 156 to 5,000 g / mol and very particularly preferably of 500 to 2,500 g / mol. Examples for R 1 are - linear C10 to C10-alkenyl - branched C9- to C50-alkenyl obtainable by polymerization of C3- and / or C ikenes - branched alkenyl, derived from homo- and copolymers containing isobutene in polymerized form and having a number-average molecular weight Mn of 104 to 100,000 g / mol, preferably of 104 to 10,000 g / mol, particularly preferably of 156 to 5,000 g / mol and very particularly preferably of 500 to 2,500 g / mol. In a preferred embodiment, R 1 a structural unit resulting from the polymerization of isobutene or an isobutene-containing monomer mixture as described below. Ideally, the homopolymer is then R 1 to leave a residue wherein n is from 0 to 960, preferably from 0 to 94, more preferably from 1 to 46 and most preferably from 3 to 22. In a further preferred embodiment, R 1a structural unit from the polymerization of 1- and / or 2-butene, especially 1-butene or a butene-containing monomer mixture. In a further preferred embodiment, R 1 a structural unit from the polymerization of propene or a propene-containing monomer mixture. In this application, C1- to C4-alkyl I, unless expressly stated otherwise, preferably represents methyl, ethyl, n-propyl or n-butyl, preferably methyl, ethyl or n-butyl, particularly preferably methyl or n-butyl and very particularly preferably methyl. In a preferred embodiment, X is a single bond and R 2 and R 3 hydrogen at the same time. In a further preferred embodiment, the amine derivative has the formula wherein R, R 1 and x have the above meanings. In this preferred embodiment, X is an organic spacer derived from succinic acid, and R 2 another single bond to the organic spacer X and R 3 a repeating radical -[-R-NH-]xH with R preferably 1,2-ethylene and x a positive integer from 1 to 4. In a further preferred embodiment, the amine derivative has the formula or or mixtures thereof, wherein R is a divalent alkylene radical which may optionally be interrupted by oxygen atoms R 1 a straight-chain or branched alkenyl radical with 9 to 200 carbon atoms R 4 and R 5 independently of each other is hydrogen or Ci- to C lkyl. In this embodiment, X is an organic spacer, R 2 Hydrogen, R 3 a group -R-NR 4 R 5 , in which R is preferably 1,3-propylene and R 4and R 5 are each methyl. In the last embodiment, the product is often also present in a mixture with a compound in which X is an organic spacer, R 2 another single bond to the organic spacer X, R 3 a group -R-NR 4 R 5 , in which R is preferably 1,3-propylene and R 4 and R 5 are each methyl. The invention is explained in more detail below: rubber In vehicle tire compounds, especially for the treads, blends of butyl rubber with diene elastomers and other components are used. Such mixtures are described, for example, in WO2019 / 199839 A1 , paragraph

[0008] until

[0070] , which is incorporated into the present disclosure by reference. In the context of this document, rubbers are understood to mean diene elastomers, i.e. homo- and copolymers of diene monomers, preferably natural rubber, polybutadienes, styrene-butadiene copolymers and polyisoprene and mixtures thereof, for example mixtures of natural rubber and styrene-butadiene copolymers, of natural rubber and polybutadienes or natural rubber and polyisoprenes. The diene elastomers usually have a glass transition temperature Tg of -75 to 0 °C Polybutadienes These are polymers of 1,3-dienes, preferably buta-1,3-diene with a cis-1,4-linkage of at least 90%, preferably at least 95%. Other comonomers can be polymerized in small amounts. The elastomer used is preferably polybutadiene with more than 90% cis-1,4 linkages, obtained by known catalytic processes with transition metal compounds, as described, for example, in French patent application FR-A-1436607. Examples of suitable conjugated dienes include, in particular, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Aromatic vinyl compounds can also be polymerized; suitable aromatic vinyl compounds include, in particular, styrene, o-, m-, and p-methylstyrene, or the commercially available "vinyltoluene" mixture. Styrene-butadiene copolymers Typical styrene-butadiene copolymers have a styrene content of 5 to 60, preferably 20 to 50 wt.%, with the remaining comonomers predominantly being 1,3-butadiene. The content of 1,2-units is generally 4 to 80 mol.%, and that of cis-1,4-units is more than 80 mol.%. Styrene-butadiene-isoprene terpolymers are also conceivable. Polyisoprene These include homo- and copolymers of isoprene, which can be of natural or preferably synthetic origin. In these, the proportion of cis-1,4 units is at least 90 mol%, preferably at least 98 mol%. Butyl rubber These are copolymers of 85 to 99.5 mol%, preferably 90 to 99.5, particularly preferably 95 to 99.5 mol% of C4-C14 isoolefins with 0.5 to 15 mol%, preferably 0.5 to 10, particularly preferably 0.5 to 5 mol% of C4-C14 conjugated dienes. The preferred isoolefin is isobutene, preferred conjugated dienes are 1,3-butadiene and isoprene, particularly preferably isoprene. The butyl rubber has a viscosity-average molecular weight of 100,000 to 1,500,000, preferably 250,000 to 800,000. The starting materials for the synthetic rubbers, preferably 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, styrene and / or isobutene, particularly preferably 1,3-butadiene, isoprene and / or isobutene, can originate at least partially, preferably entirely, from renewable sources. Their proportion of the total monomers used, measured according to ASTM D 6866 (see below), is advantageously at least 1% by weight, preferably at least 2% by weight, particularly preferably at least 10% by weight, very particularly preferably at least 25% by weight, and in particular at least 50% by weight. The proportion of monomers from renewable sources can be up to 100% by weight, preferably up to 95% by weight, particularly preferably up to 90% by weight, very particularly preferably up to 85% by weight, and in particular up to 80% by weight. Plasticizer Plasticizers (process oils) improve the processability of the composition; these are usually esters of aliphatic acids, for example fatty acid esters and fatty acid glycerides, preferably naturally occurring oils such as sunflower oil or rapeseed oil, or hydrocarbons such as paraffinic oils, aromatic oils, naphthenic petroleum oils and polybutene oils. Also suitable as plasticizers are resins known as tackifiers for adhesives and paints. These are preferably copolymers of Cs fractions of naphtha or steamer field discharges with vinyl aromatics, particularly copolymers of 1,3-butadiene, 1-butene, 2-butenes, 1,2-butadiene, 3-methyl-1-butene, 1,4-pentadiene, 1-pentene, 2-methyl-1-butene, 2-pentenes, isoprene, cyclopentadiene (which can also be present as a dicyclopentadiene dimer), piperylene, cyclopentene, 1-methylcyclopentene, 1-hexene, methylcyclopentadiene, or cyclohexene. In particular, these are copolymers of cyclopentadiene and / or dicyclopentadiene with vinylaromatics, especially styrene, α-methylstyrene, o-, m-, or p-methylstyrene, or divinylstyrene. These vinylaromatics are components of the Cg fractions of naphtha or steamer field discharges. Preferred resins as plasticizers are cyclopentadiene and / or dicyclopentadiene copolymers, cyclopentadiene and / or dicyclopentadiene-styrene copolymers, polylimonenes, limonene-styrene copolymers, limonene-cyclopentadiene and / or dicyclopentadiene copolymers, Cs fraction-styrene copolymers and Cs fraction-Cg fraction copolymers. Filler Examples of fillers are calcium carbonate, clays, mica, silica, silicates, talc, bentonite, titanium dioxide, aluminum oxide, zinc oxide and carbon black, preferably zinc oxide, silicates and carbon black. Typical particle sizes are in the range of 0.0001 to 100 pim. Silicates are understood here as derivatives of silicic acid, including its calcium or aluminum compounds. The silicates can be obtained from solution or pyrogenically and can be colloidal or precipitated. Highly dispersible silicates are preferred. The BET surface area is usually less than 450 m2 / g, preferably 30 to 400, particularly preferably from 100 to 250 m 2 / g and preferably from 130 to 220 m 2 / g, a CTAB surface of 100 to 250 m 2 / g and preferably from 150 to 200 m 2 / g, an oil uptake of DBP of 150 to 250 ml / 100 g and an average projection area of ​​the aggregates of more than 8500 nm 2 and preferably 9000 to 11000 nm 2 before use and from 7000 to 8400 nm 2 after thermomechanical mixing with an elastomer. The selected specific silica can be used alone or in the presence of other fillers, such as carbon black or another conventional silica. A particularly suitable silicon dioxide is, for example, the silicon dioxide obtained by the process described in European patent application EP-A-157703. The BET surface area, the CTAB surface area, and the oil absorption are measured according to the methods described in European patent application EP-A-157703. The mean projected area of ​​the silica is determined according to the method described in DE 69206445 T2, page 8, last paragraph to page 9, first paragraph. antioxidant Antioxidants act against oxidative degradation, in particular p-phenylenediamines are to be mentioned, for example N,N'-alkyl- or aryldisubstituted p-phenylenediamines, particularly preferred is N-(1,3-dimethylbutyl)-N'-phenyl I-1,4-phenylenediamine. Hardeners, crosslinkers, activators The rubber compositions are reacted with the aid of at least one curing agent and at least one crosslinking agent, which are known to the person skilled in the art. Examples include organic peroxides and polyamines. In particular, sulfur is used as a vulcanizing agent. Amines, diamines, guanidines, thioureas, thiatols, thiram, sulfenamides, sulfenimides, thiocarbamates, and xanthates are used as activators for the vulcanization process. N-cyclohexylbenzothiazole-2-sulfenamide (CBS) is particularly suitable. Sulphur, metal oxides, fatty acids, especially stearic acid, and in particular organosilane crosslinkers (see below under silane coupling agents) can be used as crosslinkers, for example vinyl triethoxysilane, vinyl tris (beta-methoxyethoxy) silane, methacryloylpropyl trimethoxysilane, gamma-aminopropyl triethoxysilane, gamma-mercaptopropyl trimethoxysilane and the like. In a particular embodiment, bis-(3-triethoxysilylpropyl)tetrasulfide is used. ZnO, CaO, MgO, Al2O3, CrOa, TiO2, FeO, FeOa, and NiO can be used as metal oxides. These can be used as oxides or as the corresponding fatty acid compound, preferably as stearate. Among these, zinc oxide is preferred. Silane coupling agent Typical coupling agents ensure a stable chemical and / or physical interaction between the individual components, for example fillers and rubbers. Typically these are sulfur-containing compounds, organosilanes or polysiloxanes. Preferred coupling agents are those which carry a polysulfide group and an alkoxysilyl group; particularly preferred are silane polysulfides, for example bis((Ci-C4)alkoxy(Ci-C4)alkylsilyl(Ci-C4)alkyl)polysulfides (especially disulfides, trisulfides, or tetrasulfides), such as bis(3-trimethoxysilylpropyl)polysulfide or bis(3-triethoxysilylpropyl)polysulfide. Further examples are bis(3-triethoxysilylpropyl)tetrasulfide (TESPT) of the formula [(C2H5O)3Si(CH2)3S2]2, or bis(triethoxysilylpropyl)disulfide (TESPD) of the formula [(C2H5O)3Si(CH2)3S]2. Other examples are bis(mono(Ci-C4)alkoxy di(Ci-C4)alkylsilylpropyl)polysulfide, especially disulfides, trisulfides or tetrasulfides), especially bis(monoethoxydimethylsilylpropyl)tetrasulfide. composition For example, butyl rubber makes up 5 to 40, preferably 5 to 25, phr in the tread compound of a vehicle tire. "Phr" (parts per hundred rubber) indicates the composition based on 100 parts by mass of the polymer blend. Polybutadienes can make up 30 to 50 phr, styrene-butadiene copolymers 40 to 70 phr, and polyisoprenes 0 to 20 phr, provided that the total of these polymers equals 100 phr. All non-rubber components are based on the total of these polymers. The proportion of fillers, especially carbon black and silicates, is usually 20 to 200 phr, preferably 30 to 150 phr. The proportion of plasticizers is usually 10 to 30 phr. According to the invention, the above-mentioned amine derivatives are added to these rubbers, which in a preferred embodiment may be polyisobutenyl-substituted: The polyisobutene underlying the chain is homo- and copolymers containing isobutene in polymerized form and having a number-average molecular weight Mn of 500 to 50,000, preferably 550 to 40,000, particularly preferably 650 to 30,000, very particularly preferably 750 to 20,000 and in particular 900 to 15,000. In a preferred embodiment, the polyisobutene is one with a Mn of 950 to 1050. Among these polyisobutenes, those with a high content of terminally arranged ethylenic double bonds (o-double bonds) are preferred, particularly those with an o-double bond content of at least 50 mol%, preferably at least 60 mol%, more preferably at least 70 mol%, and most preferably at least 80 mol%. These are referred to as highly reactive polyisobutenes. In a further preferred embodiment, the polyisobutene is one having a Mn of 2300 to 10000. For the production of such homopolymers or copolymers containing isobutene in polymerized form, both pure isobutene and isobutene-containing C4 hydrocarbon streams are suitable as isobutene sources, for example, C4 raffinates, in particular "raffinate 1," C4 cuts from isobutane dehydrogenation, C4 cuts from steamer fields, and from FCC crackers (fluid-catalyzed cracking), provided they are largely freed of the 1,3-butadiene they contain. A C4 hydrocarbon stream from an FCC refinery unit is also known as a "b / b" stream. Other suitable isobutene-containing C4 hydrocarbon streams include, for example, the product stream from a propylene-isobutane co-oxidation or the product stream from a metathesis unit, which are generally used after conventional purification and / or concentration. Suitable C4 hydrocarbon streams typically contain less than 500 ppm, preferably less than 200 ppm, of butadiene.The presence of 1-butene as well as cis- and trans-2-butene is largely uncritical. The isobutene concentration in the aforementioned C4 hydrocarbon streams is typically in the range of 40 to 60 wt.%. Thus, raffinate 1 generally consists essentially of 30 to 50 wt.% isobutene, 10 to 50 wt.% 1-butene, and 10 to 40 wt.% cis- and trans-2-butene. Butene and 2 to 35% by weight of butanes; in the polymerization process according to the invention, the unbranched butenes in the raffinate 1 are generally virtually inert and only the isobutene is polymerized. In a preferred embodiment, the monomer source used for the polymerization is a technical C4 hydrocarbon stream having an isobutene content of 1 to 100% by weight, in particular 1 to 99% by weight, especially 1 to 90% by weight, particularly preferably 30 to 60% by weight, in particular a raffinate 1 stream, a b / b stream from an FCC refinery unit, a product stream from a propylene-isobutane co-oxidation or a product stream from a metathesis unit. The use of water as the sole or additional initiator has proven particularly effective when using a raffinate 1 stream as the isobutene source, especially when polymerizing at temperatures from -20°C to +30°C, especially from 0°C to +20°C. However, at temperatures from -20°C to +30°C, especially from 0°C to +20°C, the use of an initiator can be omitted when using a raffinate 1 stream as the isobutene source. The isobutene or the isobutene-containing C4 hydrocarbon stream can originate at least partially, preferably completely, from renewable sources, as described, for example, in WO 2012 / 40859 A1, particularly from page 5, line 9 to page 6, line 24. The proportion of isobutene from renewable sources in the total isobutene used, measured according to ASTM D 6866, as described in WO 2012 / 40859 A1, is advantageously at least 1% by weight, preferably at least 2% by weight, more preferably at least 10% by weight, most preferably at least 25% by weight and in particular at least 50% by weight. The proportion of isobutene from renewable sources can be up to 100% by weight, preferably up to 95% by weight, more preferably up to 90% by weight, most preferably up to 85% by weight and in particular up to 80% by weight. Isobutene obtained from renewable raw materials can be characterized by the fact that the 14 C / 12C isotope ratio is determined, preferably according to ASTM D 6866 ("Determining the Biobased Content of Natural Range Materials Using Radiocarbon and Isotope Ratio Mass Spectrometry Analysis"). According to this test method, the 14 C / 12 C isotope ratio of a sample measured and compared with the 14 C / 12 C isotope ratio in a standardized 100% bio-based material. The result is the bio-based content in the sample. The application of ASTM-D6866 to derive the "biobased content" is based on the same concepts as radiocarbon dating, but without the use of age equations. The analysis is performed by determining a ratio of the amount of radiocarbon ( 14C) is determined in an unknown sample compared to that of a modern reference standard. This parameter is expressed as a percentage using the unit "pMC" (percent modern carbon). If the material being analyzed is a mixture of present-day radiocarbon and fossil carbon (with very low radiocarbon content), the resulting pMC value correlates directly with the amount of biomass material present in the sample. "Bio-based materials" are organic materials made from carbon derived from CO2 recently (on a human timescale) fixed from the atmosphere through solar energy (photosynthesis). On land, this CO2 is absorbed or fixed by plants (e.g., agricultural crops or forest plantations). In the oceans, the CO2 is captured or fixed through photosynthesis by and in bacteria or phytoplankton. Thus, a bio-based material has an isotope ratio of 14 C / 12 C greater than 0. In contrast, a fossil material has a 14 C / 12 C isotope ratio of about 0. A small part of the carbon atoms of carbon dioxide in the atmosphere is the radioactive isotope 14C, which is formed when atmospheric nitrogen is hit by a neutron produced by cosmic radiation, causing the nitrogen to lose a proton and form carbon of atomic mass 14 ( 14 C), which is then immediately oxidized to carbon dioxide. A small but measurable portion of atmospheric carbon is in the form of 14 CO2. Atmospheric carbon dioxide is assimilated by green plants to produce organic molecules during the process known as photosynthesis. Virtually all life forms on Earth depend on the production of organic molecules by green plants to generate the chemical energy that enables growth and reproduction. Therefore, the 14 C, which forms in the atmosphere, ultimately part of all life forms and their biological products, which accumulate biomass and organisms that feed on biomass with 14C. In contrast, carbon from fossil sources, especially oil or coal, does not have the characteristic 14 C: 12 C ratio of renewable organic molecules derived from atmospheric carbon dioxide. In a preferred embodiment of the present invention, the isobutene used in the polyisobutene has a bio-based content, measured as 14 C: 12 C ratio ASTM-D6866 of more than 0%, preferably at least 1%, more preferably at least 5%, most preferably at least 10%, in particular at least 20% and especially at least 25%. Advantageously, this bio-based proportion can be at least 30%, preferably at least 40%, particularly preferably at least 50%, most particularly preferably at least 66%, in particular at least 75% and especially at least 85%. With a proportion of at least 90%, preferably at least 95%, particularly preferably at least 98% and even 100%, this can be described as predominantly or completely bio-based isobutene. According to this embodiment, resources are conserved and the product is manufactured at least partially with renewable raw materials. In another embodiment of the present invention, the isobutene used in the polymerization can be obtained entirely from renewable raw materials or consist of mixtures of isobutene from renewable and fossil sources. This embodiment is particularly preferred where and as long as isobutene from renewable sources is not available in industrially sufficient quantities and economically. The isobutene-containing monomer mixture mentioned above may contain small amounts of contaminants such as water, carboxylic acids, or mineral acids without causing critical yield or selectivity losses. It is advisable to avoid the accumulation of these contaminants by removing such contaminants from the isobutene-containing monomer mixture, for example, by adsorption on solid adsorbents such as activated carbon, molecular sieves, or ion exchange resins. Although less preferred, monomer mixtures of isobutene or the isobutene-containing hydrocarbon mixture can also be reacted with olefinically unsaturated monomers copolymerizable with isobutene. If monomer mixtures of isobutene are to be copolymerized with suitable comonomers, the monomer mixture preferably contains at least 5% by weight, more preferably at least 10% by weight, and especially at least 20% by weight of isobutene, and preferably at most 95% by weight, more preferably at most 90% by weight, and especially at most 80% by weight of comonomers. In a preferred embodiment, the amine derivatives which can be used according to the invention are polyisobutene derivatives containing at least one amino group (-NR 2 R 3 ). Herein mean R 2 and R 3each independently of one another is hydrogen or Ci-C4-alkyl or, although less preferably, can form a five- to seven-membered ring with the central nitrogen atom, which may optionally contain a further heteroatom. Preferred are R 2 and R 3 independently of one another hydrogen, methyl, ethyl, n-propyl or n-butyl or together 1,4-butylene, 1,5-pentylene or 3-oxa-1,5-pentylene, particularly preferably hydrogen or methyl and very particularly preferably hydrogen. In a preferred embodiment, these are so-called polyisobutenamines (PIBA), which can be prepared from the highly reactive polyisobutene by hydroformylation and reductive amination with ammonia, monoamines or polyamines such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine, as is known in particular from EP-A 244 616. The reaction is preferably carried out with ammonia. Thus, the radical R 1 one carbon atom more than the underlying polyisobutene introduced by hydroformylation. Due to its production process, polyisobutene is a mixture of double bond isomers, which determine the properties and especially the chemical reactivity of polyisobutene. The most important are Isomers with alpha double bonds, as well as Isomers with beta-double bonds where the residue PIB stands for the residue of polyisobutene without the substructure shown. Furthermore, further isomers are conceivable, as shown, for example, in WO 2023 / 152258, which, however, only play a minor role in the invention. In a preferred embodiment of the invention, the polyisobutene used for the hydroformylation has an alpha double bond content of at least 70%, preferably at least 75%, more preferably at least 80%, most preferably at least 85%, and in particular at least 90%. Such a polyisobutene is also referred to as highly reactive polyisobutene. The content of beta-double bonds can be up to 25%, preferably up to 20, particularly preferably up to 15, most particularly preferably up to 10 and in particular up to 5%. The content of isomers other than those with alpha or beta double bonds usually does not exceed 5%. The content of isomers is determined using the 1 H-NMR spectroscopy, with the sensitivity being determined by the frequency of the measuring device. 1 H-NMR spectroscopy was performed at 700 MHz at 25 °C. Isomers were particularly preferably identified using the method described in Guo et al., Journal of Polymer Science, Part A: Polymer Chemistry, 2013, 51, 4200-4212. In a preferred embodiment, the polyisobutene has a number-average molecular weight Mn of 104 to 10,000 g / mol with the above-specified contents of alpha and beta double bonds, preferably from 156 to 5,000, particularly preferably from 500 to 2,500. In a further less preferred embodiment, the polyisobutene (A) has a number-average molecular weight Mn of more than 10,000 up to 100,000 g / mol, preferably from 11,000 to 90,000, particularly preferably from 12,000 to 80,000, very particularly preferably from 13,000 to 75,000 and in particular from 14,000 to 70,000 and a Alpha-double bond content of at least 20 to 60%, preferably at least 25 to 45%, particularly preferably at least 30 to 40%. Such a polyisobutene is also referred to as medium molecular weight polyisobutene. It is conceivable, although less preferred, to use high molecular weight polyisobutene with a number average molecular weight of more than 100,000 up to 5,000,000 g / mol, which generally has a content of alpha double bonds of not more than 50%, preferably not more than 40% and particularly preferably not more than 30%. The molecular weight is determined by gel permeation chromatography with polystyrene as standard. The idealized structure of a polyisobutenamine is In this, the sequence number n is defined as above. For a number-average molecular weight Mn of the preferred underlying polyisobutene of 168 to 2300, n is from 1 to 39, for an Mn of 224 to 1500, n is from 2 to 25, for an Mn of 550 to 1300, n is from 8 to 21, for an Mn of 700 to 1300, n is from 10 to 21, and for an Mn of 950 to 1050, n is from 15 to 17. If the underlying polyisobutene is produced from isobutene-containing C4 hydrocarbon streams (see above) containing monomers other than isobutene, the polymeric backbone comprises other monomers in polymerized form, e.g. 1-butene and cis- and trans-2-butene, in particular 1-butene. Such a polyisobutenamine is obtainable by polymerizing isobutene to a polyisobutene with an (idealized) terminal double bond, which is then subjected to hydroformylation and subsequent amination with ammonia. This process is described by way of example in Example 1 of US Pat. No. 4,832,702. The parameter n corresponds to the degree of polymerization minus 2 of the isobutene in the polyisobutene; the polyisobutene used preferably has a molecular weight of approximately 1000 g / mol. In a further preferred embodiment, these are compounds containing free amino and imido groups, such as preferably reaction products of alkyl- or alkenyl-substituted succinic anhydride with aliphatic polyamines (polyalkyleneimines) such as in particular ethylenediamine, Diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine and hexaethyleneheptamine, which have an imide structure. Such polyisobutenylsuccinimides have the formula on, in which R 1 represents a polyisobutenyl radical having a number-average molecular weight Mn of 104 to 100,000 g / mol, preferably of 104 to 10,000 g / mol, particularly preferably of 156 to 5,000 g / mol and very particularly preferably of 500 to 2,500 g / mol, and x represents a positive integer of, for example, 1 to 4, preferably 2 to 4, particularly preferably 3 or 4. Preferably, the residue R 1 a molecular weight of 550 to 2300, preferably 650 to 1500 and particularly preferably 750 to 1300 g / mol. In a further preferred embodiment, the reaction products of alkyl- or alkenyl-substituted succinic anhydride with N-mono- or doubly substituted 1,3-alkylenediamines, preferably 1,3-propylenediamines, are used as amine derivatives which can be used according to the invention. Beispiele dafür sind N-Cyclohexylpropylendiamin-1 ,3; N-2-Ethylhexylpropylendiamin-1 ,3; N-Dodecyl-1 ,3- Propylendiamin; N-Stearylpropylendiamin-1 ,3; N-Oleylpropylendiamin-1,3; N-3-Aminopropyltalgfettamin; N- Arachidyl propy lendiam i n- 1 ,3; N-Beheny Ipropy lendi am i n- 1 ,3; N-Benzyl-propylendiamin-1 ,3; N-Phenylpropylendiamin- 1,3; 2-Aminoethylstearylamin; 2-Aminoethylbehenylamin; 2-Aminoethyloleylamin; 2-Aminoethyltalgfettamin; N- Stearylbishexamethylendiamin-1,6; N-Stearyldipropylentriamin; N-Dodecyldipropylentriamin; N,N- Dimethylaminopropylamin-1,3; N,N-Ditridecylpropylendiamin-1,3; N,N-Bis(2-Ethylhexyl)-3-Aminopropylenamin; Bis- aminopropyltalgfettamin; Bis-aminopropyllaurylamin, 1-(2-Aminopropyl)-stearylamin; 1-(2-Aminopropyl)-piperazin; N- 2-Aminoethyl-piperidin; N-3-Aminopropylimidazol. Bevorzugt ist N,N-Dimethylaminopropylamin-1,3. As a rule, the respective amides are formed first when the anhydride functionalities are opened, or at higher reaction temperatures the ring closure to the respective imides occurs. The preparation is described, for example, in WO 2012 / 004300. If the temperature in the reaction of the alkyl- or alkenyl-substituted succinic anhydride with the N-mono- or doubly substituted 1,w-alkylenediamine is kept below about 80 °C, an amide is predominantly formed, although minor amounts of imide are also formed under these reaction conditions. The compounds which can be used according to the invention and which contain a spacer X derived from succinic acid are generally based on polyisobutenyl-substituted succinic anhydrides (PIBSA), which are obtainable by ene reaction of highly reactive polyisobutenes with maleic anhydride and serve as starting compounds for the amides or imides. In a preferred embodiment, highly reactive polyisobutenes having the number-average molecular weight Mn indicated above are used for these polyisobutenyl-substituted succinic anhydrides. In a preferred embodiment, the polyisobutenyl-substituted succinic anhydrides (PIBSA) to be used also have more than singly substituted products. The ratio of the higher to the monomaleated components can be expressed as the "bismaleation degree" (BMG). The BMG is known per se (see also US 5,883,196) and can be determined using the following formula: BMG = 100% x [(wt-%(BM PIBSA) / (wt-%(BM PIBSA)+wt-%(PIBSA))] where wt-%(X) stands for the respective weight fraction of component X (X = PIBSA (mono-maleated polyisobutene) or BM PIBSA (more than mono-maleated polyisobutene)) in the reaction product of polyisobutene with maleic anhydride. The degree of bismaleation is preferably calculated from the saponification number of the sample according to DIN 53401: 1988-06. If necessary, the sample must be solubilized with a suitable solvent, preferably a 2:1 mixture of toluene and ethanol. It should be noted that only the ratio of the more highly maleated components to the singly maleated components is taken into account, whereas unreacted polyisobutene in the reaction mixture, for example, that which does not contain reactive double bonds, is not included in the determination of the degree of bismaleation. Therefore, the reaction mixture may also contain unreacted polyisobutene. which usually corresponds to the proportion in the polyisobutene used that does not contain any reactive double bonds, whereas the proportion in the polyisobutene containing reactive double bonds preferably reacts completely or almost completely. In a preferred embodiment, the PIBSA have a degree of bismaleation of at least 5%, preferably at least 8%, particularly preferably at least 10%. With further advantage, such reaction products of polyisobutene with a degree of bismaleation of at least 12%, preferably at least 15%, particularly preferably at least 20% can be used. The degree of bismaleation can be up to 60%, preferably up to 55%, particularly preferably up to 50%, especially up to 45%, and especially up to 40%. By choosing suitable reaction conditions, especially a high excess of maleic anhydride, the degree of bismaleation can be increased to up to 80% and even up to 100%. The best results are achieved with a degree of bismaleation of 10 to 50%, preferably 12 to 45% and particularly preferably 15 to 40%. The amine derivatives according to the invention are generally added to the rubber mixture in amounts of 2 to 20, preferably 4 to 14, particularly preferably 5 to 10 phr. Typically, these compounds are added to the rubber compound along with the other ingredients and heated in a kneader or extruder to initiate vulcanization. It may also be advantageous to first thoroughly mix the rubber compound and fillers with the amine derivatives and then add the other ingredients, especially antioxidants, activators, and / or plasticizers, later. Accordingly, a further embodiment of the present invention is a process for reducing the viscosity of rubber compositions in the manufacture of rubber-containing tires, in which - at least one rubber with - soot and / or silicates and - at least one processing aid and / or additive for improving at least one performance property of the tire in a kneader and / or extruder, wherein at least one amine derivative as described above is added to the rubber mass before and / or during processing. The processes for vulcanization and production of rubber compounds are known per se and can be transferred to the use of amine derivatives. It is an advantage of the amine derivatives that they have a beneficial effect on improving at least one of the following properties - Dispersion coefficient - particle size - Wet grip - Abrasion resistance - rolling resistance of rubber-containing tires. The amine derivatives are particularly suitable for improving the dispersion of fillers, especially silica, in rubber compounds. Furthermore, they show a particular advantage in reducing rolling resistance. During the production of rubber compounds, the use of amine derivatives also has the advantage of significantly reducing the viscosity of the rubber compounds during processing and production of rubber-containing tires. Accordingly, a further subject of the present invention is a process for reducing the viscosity of rubber compositions in the production of rubber-containing tires, in which - at least one rubber with - soot and / or silicates and - at least one processing aid and / or additive for improving at least one performance property of the tire in a kneader and / or extruder by adding at least one amine derivative as described to the rubber mass before and / or during processing. Furthermore, these compounds exhibit advantages with regard to wet grip at low temperatures (-10 °C) and / or rolling resistance and / or abrasion resistance of the tires containing them. The amine derivatives preferably improve at least two of these three properties. It is a particular advantage that the amine derivatives simultaneously exhibit advantages with regard to wet grip at low temperatures (-10 °C) and rolling resistance and abrasion resistance of the tires. By increasing the abrasion resistance of tires, the release of microplastics from tire wear during motor vehicle operation is reduced. Another subject matter is rubber compositions containing - at least one rubber selected from the group consisting of isobutene-isoprene rubber, styrene-butadiene rubber and natural rubber, - at least one filler selected from the group consisting of calcium carbonate, clays, mica, silica, silicates, talc, bentonite, titanium dioxide, aluminum oxide, zinc oxide and carbon black, - at least one antioxidant, preferably a p-phenylenediamine, - at least one peroxide and / or polyamine as hardener and / or crosslinker, - at least one activator for the vulcanization process selected from the group consisting of amines, diamines, guanidines, thioureas, thiatols, thiramen, sulfenamides, sulfenimides, thiocarbamates and xanthates, - at least one silane crosslinker selected from the group consisting of bis((Ci-C4)alkoxy(Ci-C4)alkylsilyl(Ci-C4)alkyl)polysulfides, (especially disulfides, trisulfides or tetrasulfides), bis(3-trimethoxysilylpropyl) polysulfide, bis(3-triethoxysilylpropyl)polysulfide, bis(3-triethoxysilylpropyl)tetrasulfide (TESPT) of the formula [(C2H5O)3Si(CH2)3S2]2, and bis(triethoxysilylpropyl)disulfide (TESPD) of the formula [(C2H5O)3Si(CH2)3S]2, and at least one amine derivative of the formula A further subject of the present invention are those cases in which at least one of the two radicals R 2 and R 3 Hydrogen is, preferably when both are hydrogen, compounds of the formula R 1 -X-NR 3 -Si(OC2H5)2-(CH2)3-S4-(CH2)3-Si(OC2H5)3 and R 1 -X-NR 3 -Si(OC2H5)2-(CH2)3-S2-(CH2)3-Si(OC2H5)3, in which R 1 , X and R 3have the above meanings, and rubber compositions containing at least one of these compounds, their use in rubber-containing tires, in particular for improving the compatibility of silicates in rubber-containing tires and their use for improving at least one of the following properties - Dispersion coefficient - particle size - Wet grip - Abrasion resistance - Rolling resistance -Vulcanization speed of rubber-containing tires. Another object of the present invention are derivatives of polyisobutenamine with the silane coupling agent having the idealized structure as follows: where the sequence number n is as defined above and Y for -(S) y -R 25 -Si(OR 26 )3and y stand for 1, 2, 3 or 4 and R 25an alkylene radical having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, particularly preferably 2 or 3 carbon atoms and very particularly preferably selected from the group consisting of methylene, 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,4-butylene, 5-oxa-1,5-pentylene and 1,6-hexylene, in particular 1,3-propylene, and R 26 is Ci- to Ce-alkyl, preferably Ci- to C alkyl, particularly preferably methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl, very particularly preferably methyl, ethyl or n-butyl, in particular methyl or ethyl and especially methyl. These compounds, as well as rubber compositions containing at least one of these compounds, their use in rubber-containing tires, particularly for improving the compatibility of silicates or as coupling agents in rubber-containing tires and their use for improving at least one of the following properties - Dispersion coefficient - particle size - Wet grip - Abrasion resistance - Rolling resistance -Vulcanization speed of rubber-containing tires are also the subject of the present invention. A further object of the present invention for those cases in which at least one of the two residues R 2 and R 3 Hydrogen, preferably when both are hydrogen, are derivatives of the amine compounds with the Fatty acids used in activators, especially stearic acid, with the structure as follows: R 1 -X-NR 3 -(C=O)-R 10 in which R 1 , X and R 3 have the above meanings and R 10 the residue of a fatty acid, preferably a saturated alkyl residue or mono- or polyunsaturated alkenyl residue having 9 to 19 carbon atoms. Preferred is the residue R 10 -(C=O)- derived from fatty acids such as lauric acid, myristic acid, stearic acid, palmitic acid, lauric acid, oleic acid, linoleic acid and linolenic acid or mixtures thereof. Technically common fatty acid mixtures are preferably tallow fatty acid, coconut oil fatty acid, tallow fatty acid, coconut palm kernel oil fatty acid, soybean oil fatty acid, rapeseed oil fatty acid, peanut oil fatty acid or palm oil fatty acid, which contain oleic acid and palmitic acid as main components. These compounds, as well as rubber compositions containing at least one of these compounds, their use in rubber-containing tires, especially vulcanization activators or accelerators in rubber-containing tires and their use for improving at least one of the following properties - Dispersion coefficient - particle size - Wet grip - Abrasion resistance - Rolling resistance -Vulcanization speed of rubber-containing tires are also the subject of the present invention. Furthermore, the compounds according to the invention are suitable for binding alcohols, particularly ethanol, released during the production of rubber compositions for tires, so that lower emissions are released during production. Without wishing to be bound by any theory, it is assumed that such alcohols R released during the production of rubber compounds for tires 6 OH, especially ethanol, react with previously unreacted succinic anhydride or carboxylic acid groups and form carboxylic acid esters. It is also conceivable that the released alcohol R 6 OH, especially ethanol, alcohols or amines are displaced from the existing carboxylic acid ester, amide or imide bond in a transesterification or transamidation. For example, the following compounds can be formed: From the connections can be formed From the connection can be formed or where the variables each have their above meaning. In the case of amine derivatives of the formula wherein R 2 and R 3 is hydrogen, one of the radicals R 2 and R 3 or both by R 6 , preferably replaced by ethyl. These compounds resulting from the reaction with released alcohol, as well as rubber compositions containing at least one of these compounds, their use in rubber-containing tires, particularly for improving the compatibility of silicates or as coupling agents in rubber-containing tires and their use for improving at least one of the following properties - Dispersion coefficient - Particle size - Wet adhesion - Abrasion resistance - Rolling resistance -Vulcanization speed of rubber-containing tires are also the subject of the present invention. The present invention is illustrated by the following examples, but is not limited thereto. Examples Manufacturing examples Connection 1 Polyisobutenamine with a number average molecular weight Mn of approximately 1000 g / mol, commercially available as Kerocom PIBA 03 from BASF SE, Ludwigshafen, dissolved in Mihagol. Connection 2 150.20 g Glissopal® 1000 from BASF SE, Ludwigshafen, number average molecular weight Mn (determined by GPC) approx. 1000 g / mol, polydispersity approx. 1.6, content of alpha double bonds (determined by 13 C NMR) approx. 88%, beta-double bonds 6%, were heated with 29.4 g (0.30 mol, 2 eq.) of maleic anhydride in an autoclave at 225 °C and stirred for 7 h. The reaction mixture was then cooled to 80 °C and treated with 150 ml of heptane. The solution was stirred at 100 °C for 1 h and then filtered. The solvent was removed in vacuo (yield = 164.00 g). (SV: 175 mg KOH / g). A polyisobutenylsuccinic anhydride (PIBSA) with a bismaleation degree of approximately 100% was obtained. Connection 3 122.2 g of a polyisobutenylsuccinic anhydride obtained analogously to compound 2 with a SV of 91.8 mg KOH / g was dissolved in 100.60 g of toluene. The reaction mixture was treated with 11.20 g (0.11 mol) of 3-dimethylaminopropylamine and stirred for 2 h at 120 °C. The reaction mixture was then cooled to room temperature, and the solvent was removed under vacuum (yield = 130.50 g). Connection 4 126.10 g of a polyisobutenylsuccinic anhydride obtained analogously to compound 2 with a SV of 89.0 mg KOH / g was dissolved in 100.00 g of toluene. 18.90 g (0.10 mol) of tetraethylenepentamine was added to the reaction mixture and stirred at 120 °C for 2 h. The reaction mixture was then cooled to room temperature, and the solvent was removed under vacuum (yield = 142.10 g). Method description Improvement of the dispersion coefficient The macrodispersion (Dispersion Index Analysis System, DIAS) of the undistributed filler agglomerates (particles) is determined by comparing the reflectance of the particle surfaces with the total observation area using a light microscope at 125x magnification of at least 10 images. This yields the degree of dispersion (expressed as a percentage), taking correction factors to account for the filler volume content and the void volume of the fillers. The aim is to achieve a high dispersion coefficient. Determination of particle size The mean particle diameter was determined optically together with the calculation of the dispersion coefficient. A small particle size is advantageous. Wet grip at low temperatures (-10 °C) and rolling resistance A strip test specimen (40 x 10 x 2 mm) of the produced rubber compound is subjected to dynamic mechanical analysis (DMA) in an ARES test device from Rheometric Scientific™. Measurement parameters: Temperature range -60 to 80 °C Frequency 1 Hz Amplitude 0.5% The tan(ö) value at -10 °C is considered a measure of traction on wet roads at low temperatures, the tan(ö) value at +60 °C as a measure of rolling resistance. High values ​​for tan(ö).io»c mean high wet grip and are advantageous, low values ​​for tan(ö)eo°c mean low rolling resistance and are desirable. Abrasion resistance The abrasion was measured according to DIN ISO 4649 in an abrasion apparatus from Frank at a load of 10 N over a sliding length of 40 m and a rotation of 40 rrr 1 certainly. The abrasion index is given in percent [%], higher values ​​are positive. Reduction of viscosity during processing The components of the rubber masses were mixed together in the specified proportions and the Mooney viscosity of the mass was determined at a temperature of 100 °C at 2 revolutions / min in a Mooney meter Alpha Technologies MV 2000 E (Mooney ML (1+4) 100 °C). Viscosity is measured in Mooney units (MU). Vulcanization acceleration A silica-containing rubber compound as described below was treated at 160 °C at an amplitude of 0.5% and a frequency of 1.67 Hz in a Monsanto Rheometer MDR 2000E, with the torque being monitored over time. The increase in torque describes the progress of vulcanization. Furthermore, the rubber mass was vulcanized at 160 °C at a load of 280 bar in a Rucks Maschinenbau KV 207.00 apparatus to determine the tgo value. A reduction in the tgo time is advantageous. Application examples Silica-containing ("reference") rubber compounds were prepared as a comparison or with the additives according to the invention with the following composition: 1) Rubber Nipol NS616 (modified S-SBR, styrene content: 20 wt%, vinyl group content: 67 mol%, SP value: 17.25 (J / cm 3 ) 1 / 2 , Tg: -25°C, Mw: 510,000, non-oil-extended) manufactured by ZEON CORPORATION (SBR1 in EP 3263360 A1 , paragraph

[0054] ) 2) Amorphous SIO2, Ultrasil 7000 GR from Evonik 3) Bis(triethoxysilylpropyl)tetrasulfide 4) IPPD: N-isopropyl-N'-phenyl-1,4-phenylenediamine 5) DPG: N, N'-Diphenylguanidine 6) CBS: N-Cyclohexylbenzothiazole-2-sulfenamide Rubber compositions according to the invention By adding the specified amount of the compounds according to the invention, silica-containing rubber compositions K1 to K5 were prepared analogously to the silica-containing reference rubber composition "Reference." To compensate, the proportion of plasticizer was partially reduced accordingly. Example 1 (Improving the dispersion coefficient) Example 2 (reduction of particle size) Example 3 (wet grip at low temperatures (-10 °C)) Example 4 (rolling resistance) Example 5 (Abrasion resistance) Example 6 (Shore A hardness) The Shore A hardness was determined using a Zwick digitest device according to DIN ISO 48-4. Example 7 (Acceleration of vulcanization)

Claims

Patent claims 1 . Use of amine derivatives of the formula wherein X is a single bond or an organic spacer, R 1 a straight-chain or branched alkenyl radical having a molecular weight Mn of 104 to 100,000 g / mol, preferably of 104 to 10,000 g / mol, particularly preferably of 156 to 5,000 g / mol and very particularly preferably of 500 to 2,500 g / mol R 2 and R 3 independently of each other, a further single bond to the organic spacer X, hydrogen, Ci- to C4-alkyl, a group -R-NR 4 R 5 or a repeating radical -[-R-NH-]xH x is a positive integer from 1 to 4 R is a divalent organic radical having 2 to 6 carbon atoms, preferably selected from the group consisting of 1,2-ethylene, 1,2-propylene and 1,3-propylene, R 4 and R 5independently hydrogen or Ci- to C lkyl is to improve at least one of the following properties - Dispersion coefficient - particle size - Wet grip - Abrasion resistance - Rolling resistance -Vulcanization speed of rubber-containing tires.

2. Use according to claim 1, characterized in that the amine derivative is a polyisobutenamine of the formula wherein n is a positive integer from 0 to 960, preferably from 0 to 94, particularly preferably from 1 to 46 and most preferably from 3 to 22.

3. Use according to claim 1, characterized in that the amine derivative has the formula or fulfilled, in which R is a divalent alkylene radical which may optionally be interrupted by oxygen atoms R 4 and R 5independently of one another is hydrogen or ci- to C alkyl.

4. Use according to claim 3, characterized in that - R 1 ,3-propylene and - R 4 and R 5 each is Ci- to C lkyl.

5. Use according to claim 1, characterized in that the amine derivative has the formula fulfilled, in which R is a divalent alkylene radical which may optionally be interrupted by oxygen atoms and x is a positive integer from 1 to 4.

6. Use according to claim 5, characterized in that - R 1,2-ethylene and - x is a positive integer from 1 to 4, preferably 2 or 3.

7. Use according to one of claims 1 or 3 to 6, characterized in that R 1 is selected from the group consisting of - linear C10 to C10-alkenyl - branched C9- to C50-alkenyl, which is obtainable by polymerization of C3- and / or C ikenes - branched alkenyl, derived from homo- and copolymers containing isobutene in polymerized form and having a number-average molecular weight Mn of 104 to 100,000 g / mol, preferably of 104 to 10,000 g / mol, particularly preferably of 156 to 5,000 g / mol and very particularly preferably of 500 to 2,500 g / mol.

8. Use according to one of claims 1 or 3 to 6, characterized in that the residue R 1 to a remainder wherein n is from 0 to 960, preferably from 0 to 94, more preferably from 1 to 46 and most preferably from 3 to 22.

9. Use according to one of the preceding claims for improving simultaneously at least two, preferably all three of the following properties - Wet grip - Abrasion resistance - Rolling resistance of rubber-containing tires.

10. Use according to any one of claims 1 to 9 for reducing microplastics from tire abrasion.

11. Use according to any one of claims 1 to 9 for reducing fuel consumption and associated emissions by reducing the rolling resistance of rubber-containing tires.

12. Use according to one of the preceding claims, characterized in that the The rubber is an isobutene-isoprene rubber.

13. Use according to one of claims 1 to 11, characterized in that the rubber is a styrene-butadiene rubber.

14. A process for reducing the viscosity of rubber compounds in the manufacture of rubber-containing tires, in which - at least one rubber with - soot and / or silicates and - at least one processing aid and / or additive for improving at least one performance property of the tire in a kneader and / or extruder, characterized in that at least one amine derivative as described in one of claims 1 to 8 is added to the rubber mass before and / or during processing.

15. Use of amine derivatives as described in any one of claims 1 to 8 for lowering the Viscosity of rubber compounds in the production of rubber-containing tires.

16. Rubber composition containing - at least one rubber selected from the group consisting of natural rubber, polybutadienes, styrene-butadiene copolymers and polyisoprene and mixtures thereof, preferably mixtures of natural rubber and styrene-butadiene copolymers, of natural rubber and polybutadienes or of natural rubber and polyisoprenes, - at least one filler selected from the group consisting of calcium carbonate, clays, mica, silica, silicates, talc, bentonite, titanium dioxide, aluminum oxide, zinc oxide and carbon black, - at least one antioxidant, preferably a p-phenylenediamine, - at least one peroxide and / or polyamine as hardener and / or crosslinker, - at least one activator for the vulcanization process selected from the group consisting of amines, diamines, guanidines, thioureas, thiatols, thiramen, sulfenamides, sulfenimides, thiocarbamates and xanthates, - at least one silane crosslinker selected from the group consisting of bis((Ci-C4)alkoxy(Ci-C4)alkylsilyl(Ci-C4)alkyl)polysulfides (especially disulfides, trisulfides or tetrasulfides), bis(3-trimethoxysilylpropyl), bis(3-triethoxysilylpropyl)polysulfide, bis(3-triethoxysilylpropyl)tetrasulfide (TESPT) of the formula [(C2H5O)3Si(CH2)3S2]2, and bis(triethoxysilylpropyl)disulfide (TESPD) of the formula [(C2H5O)3Si(CH2)3S]2, and at least one amine derivative as described in any one of claims 1 to 8.

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