Compound, preparation and use thereof in rubber blends and vehicle tires, as an Anti-aging agent, antioxidant, antioxidant and / or coloring agent

Abstract

The invention relates to a compound (I), a rubber blend containing the compound, a vehicle tire comprising the rubber blend in at least one component, a process for preparing the compound, and the use of the compound as an anti-aging agent and / or antioxidant and / or coloring agent, wherein R1 is selected from the group consisting of xi) aromatic groups, the aromatic groups optionally carrying substituents that are selected from the group consisting of halogen groups, cyano groups, ester groups, ketone groups, ether groups and thioether groups, and xii) linear, branched and cyclic aliphatic C3 to C12 groups, wherein X is selected from among O (oxygen atom), S (sulfur atom) and N(H) (secondary amino group), and Y is selected from among O (oxygen atom), S (sulfur atom) and N(H) (secondary amino group).

Description

[0001] Description

[0002] COMPOUND, ITS PRODUCTION AND USE IN RUBBER COMPOUNDS AND VEHICLE TIRES, AS AN AGING inhibitor, ANTIOXIDANT AND / OR DYE

[0003] The invention relates to a compound, a rubber mixture containing the compound, a vehicle tire which has the rubber mixture in at least one component, a process for producing the compound and the use of the compound as an ageing inhibitor and / or antioxidant and / or dye.

[0004] It is known that polymeric materials, particularly rubber, are used in vehicle tires and technical rubber articles.

[0005] Natural rubber, synthetic polymers (such as IR, BR, SSBR, ESBR, etc.), as well as natural and synthetic oils, greases, and lubricants, are subject to oxidation reactions during extended storage, especially in their intended application, which often takes place at elevated temperatures. These oxidation reactions adversely affect the original desired properties. Depending on the type of polymer, the polymer chains are shortened, even leading to liquefaction, or the material subsequently hardens.

[0006] Anti-aging agents therefore contribute significantly to the longevity of vehicle tires and other technical rubber products.

[0007] Known anti-aging agents are aromatic amines, such as 6PPD (N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine), IPPD (N-isopropyl-N'-phenyl-p-phenylenediamine) or

[0008] SPPD (N-(1-phenylethyl)-N'-phenyl-p-phenylenediamine). These molecules can react with oxygen or ozone or formed radicals, such as alkyl, alkoxy, and alkylperoxy radicals, and thus scavenge them and protect the polymers from further oxidation reactions.

[0009] A disadvantage of this class of substances, however, is the suspicion that they could be carcinogenic.

[0010] Anti-aging agents that react particularly with ozone and capture it are also called “ozone protectants” or “antiozonants”.

[0011] Another problem associated with anti-aging agents is undesirable blooming. Due to their poor solubility in the surrounding polymer matrix of the rubber article, molecules of the anti-aging agent diffuse to the surface of the article to be protected, forming a film there whose color is usually distinguishable from the rest of the article. In vehicle tires, this usually manifests itself in a brown discoloration of the otherwise black sidewall. In addition to the aesthetic disadvantages, this also has disadvantages with regard to the anti-aging effect. In most cases, bloomed substances are removed. This not only reduces the total amount of anti-aging agent, but also causes further molecules of the anti-aging agent to diffuse, so that the polymers are increasingly less protected.

[0012] The invention is based on the object of providing a novel compound that can be used, in particular, as an anti-aging agent in vehicle tires or other technical rubber articles. This compound has a lower hazard potential and is sufficiently soluble in the respective matrix, for example, and in particular, in the polymer. This should ensure continued optimal protection against oxygen and ozone while reducing health hazards, and minimize or prevent the tendency to blooming.

[0013] At the same time, the compound is intended to achieve a comparable or even improved anti-aging effect compared to aromatic amines, such as 6PPD. This object is achieved by the compound according to the invention according to claim 1, the rubber mixture according to the invention containing the compound, and the vehicle tire according to the invention, which comprises the rubber mixture according to the invention in at least one component.

[0014] Furthermore, the object is achieved by the process according to the invention for producing the compound according to the invention.

[0015] The compound according to claim 1 has the general formula I): where R 1is selected from the group consisting of xi) aromatic radicals, wherein the aromatic radicals optionally carry substituents selected from the group consisting of halogen radicals, cyano radicals, ester radicals, ketone radicals, ether radicals and thioether radicals, and xii) linear, branched and cyclic aliphatic C3 to C12 radicals, wherein the radicals R 2 and R 3can independently of one another be the same or different and are selected from the group consisting of linear, branched and cyclic, saturated and unsaturated, aliphatic C 1 to C 12 radicals, which optionally carry one or more halogen substituents, aryl radicals which optionally carry one or more halogen substituents, and halogen radicals, with fluorine, bromine and chlorine being preferred, cyano radicals, ester radicals, ketone radicals, ether radicals and thioether radicals; and where m takes the value 0 or 1 or 2 or 3, and where n takes the value 0 or 1 or 2 or 3 or 4, where X is selected from 0 (oxygen atom), S (sulfur atom) and N(H) (secondary amino group), where Y is selected from 0 (oxygen atom), S (sulfur atom) and N(H) (secondary amino group). It will be clear to the person skilled in the art that, for example, in the case of m being 0 (zero) or 1 or 2, instead of the R 2each hydrogen atom is bonded to the corresponding carbon atom of the benzene ring. This applies analogously to R 3 and n is less than 4. It will also be clear to the person skilled in the art that the representation of the links of (R 2 ) m , (R 3 )n' and R 1 HN in the benzene ring of the skeleton means that these groups can be arranged at any position on the respective benzene ring, except of course not two or more at the same position at the same time, which would be excluded due to the tetravalent nature of the carbon atom of the benzene ring.

[0016] In the context of the present invention, terms such as "C3 to C12 residues" mean residues with 3 to 12 carbon atoms. Irrespective of this, "C1" is used to designate the position of the most highly oxidized carbon atom or the highest priority according to the Cahn-Ingold-Prelog (CIP) convention. The person skilled in the art will understand what is meant in the respective context.

[0017] The compound according to the invention is a dibenzodiazepinone derivative and has a lower hazard potential than known anti-aging agents based on aniline (possible cleavage product of 6PPD).

[0018] This is a crucial advantage, especially in technical applications such as vehicle tires or other technical rubber products, since the rubber components can be released through abrasion or other degradation processes. Furthermore, the base compound dibenzodiazepinone is found in a variety of orally administered medications.

[0019] The compound according to the invention exhibits improved oxidation protection compared to the known anti-aging agent 6PPD, particularly at higher temperatures of more than 150°C, whereby a comparable or even improved protective effect is achieved with the compound according to formula I), particularly in vehicle tires and other technical rubber articles, but also in oils and lubricants. However, the invention is not intended to be tied to a specific mechanism of action or a specific explanation.

[0020] The compound according to the invention is therefore suitable as a replacement for 6PPD, whose degradation products are extremely toxic to coho salmon and thus probably also to other aquatic organisms.

[0021] The compound according to the invention also exhibits sufficient solubility in rubber compounds, particularly for vehicle tires and other technical rubber articles. This minimizes blooming of this compound, which is known to occur with many antioxidants, which in turn has a beneficial effect on the anti-aging effect. The less blooming of the antioxidant, the less antioxidant is intentionally or inadvertently removed from the surface of the article to be protected, and the less antioxidant diffuses to the surface.

[0022] The compound according to the invention according to formula I) is particularly suitable as an ageing inhibitor and / or ozone protectant in vehicle tires and / or other technical rubber articles, such as in particular an air spring, a bellows, conveyor belt, strap, belt, hose, rubber band, profile, a seal, a membrane, tactile sensors for medical applications or robot applications, or a shoe sole or parts thereof, and / or oils and / or lubricants.

[0023] The compound according to the invention according to formula I) is particularly suitable for producing a rubber article, in particular an air spring, a bellows, conveyor belt, strap, belt, hose, rubber band, profile, a seal, a membrane, tactile sensors for medical applications or robot applications, or a shoe sole or parts thereof.

[0024] For use of the compound according to formula I) in the aforementioned articles or substances, it is used in a composition and mixed into it. In the case of vehicle tires or other technical rubber articles, this is particularly a rubber compound.

[0025] The invention further relates to the use of the compound according to formula I) in oils and lubricants, such as, in particular, fuels or operating fluids for engines. The compound according to the invention can thus be used in particular in engines.

[0026] The invention further relates to the use of the compound according to the invention according to formula I) as a dye in fibers and / or polymers and / or paper and / or in (coating) paints and varnishes.

[0027] The invention encompasses all advantageous embodiments, which are reflected, inter alia, in the patent claims. In particular, the invention also encompasses embodiments resulting from the combination of different features with varying degrees of preference, so that a combination of a first feature designated as "preferred" or described within the scope of an advantageous embodiment with another feature designated, for example, as "particularly preferred" is also encompassed by the invention.

[0028] Furthermore, all statements regarding the features of the compound according to the invention also apply to the process according to the invention for producing the compound and the rubber mixture according to the invention containing the compound as well as the uses according to the invention.

[0029] The group -N(H)R is preferred 1 arranged in meta position to X.

[0030] Thus, the compound according to the invention preferably has the structure according to formula II): where R 1 , R 2 , R 3 , X and Y, and m and n are as defined above. This achieves the object underlying the invention particularly well, with the compound achieving, in particular, sufficient solubility in rubber mixtures, especially for vehicle tires.

[0031] X is, as can be seen in formula I) and II), incorporated into the ring structure and selected from O (oxygen atom), S (sulfur atom) and N(H) (secondary amino group).

[0032] It will be clear to the person skilled in the art that when X is NH, the nitrogen atom (N) is bonded to the adjacent carbon atoms, while the hydrogen atom (H) is bonded only to the nitrogen atom.

[0033] Preferably, X, for example and especially in formulas I) and II), is NH. This achieves the object underlying the invention particularly well, particularly achieving very good oxidation protection in polymers and / or rubber mixtures, especially for vehicle tires.

[0034] Y is, as can be seen in formulas I) and II), terminally bonded to the carbon atom and selected from O (oxygen atom), S (sulfur atom) and N(H) (secondary amino group).

[0035] It will be clear to the person skilled in the art that when Y is NH, the nitrogen atom (N) is bonded to the adjacent carbon atom, while the hydrogen atom (H) is bonded only to the nitrogen atom.

[0036] Preferably, Y, for example and in particular in formulas I) and II), is in each case equal to 0, i.e. an oxygen atom, which results in a carbonyl group (-C=O) next to X.

[0037] As a result, the object underlying the invention is achieved particularly well, whereby in particular very good oxidation protection is achieved in polymers and / or rubber mixtures, in particular for vehicle tires.

[0038] The residues R 2 and R 3 are independently identical or different and are selected from the group consisting of linear, branched and cyclic, saturated and unsaturated, aliphatic Ci to C-12 radicals, which optionally carry one or more halogen substituents, aryl radicals, which optionally carry one or more halogen substituents, and halogen radicals, with fluorine, bromine and chlorine being preferred, cyano radicals, ester radicals, ketone radicals, ether radicals and thioether radicals.

[0039] The mentioned residues R 2 and R 3 can already be bound to the respective benzene ring or its precursor, in particular by selecting suitable starting substances.

[0040] Preferably, for example and in particular in formulas I) and II), m is zero (0).

[0041] Preferably, for example and in particular in formulas I) and II), n is zero (0).

[0042] The preferred structures are those shown in formulas la) and Ha): where X, Y and R 1 as defined above.

[0043] Preferably, X is equal to N(H) and Y is equal to 0.

[0044] The rest R 1 is selected from the group consisting of xi) aromatic radicals, wherein the aromatic radicals optionally carry substituents selected from the group consisting of halogen radicals, cyano radicals, ester radicals, ketone radicals, ether radicals and thioether radicals, and xii) linear, branched and cyclic aliphatic C3 to C12 radicals.

[0045] The aromatic radical from subgroup xi) is, for example, and preferably selected from phenyl radicals (-CßHs) and benzyl radicals (-CH2-C6H5), with phenyl being particularly preferred.

[0046] The aromatic residues of subgroup xi) may bear substituents. As stated above, these are selected from the group consisting of halogen residues, cyano residues, ester residues, ketone residues, ether residues, and thioether residues.

[0047] The substituents are preferably selected from the group consisting of ester residues, ketone residues, ether residues and thioether residues.

[0048] According to preferred embodiments, the aromatic radical is unsubstituted at the two C atoms adjacent to the Ci atom, i.e., the carbon atom bonded to the N atom. In the case of a benzene ring as the basic structure, there is preferably no substituent in the ortho / trio position to the N atom.

[0049] According to further preferred embodiments, the aromatic radical of subgroup xi) is unsubstituted.

[0050] It is preferred that R 1 is bonded to the nitrogen atom (N) via a tertiary carbon atom. Thus, the Ci atom is preferably a tertiary carbon atom. For the purposes of the present invention, the term "tertiary carbon atom" refers to a carbon atom bonded to only one hydrogen atom.

[0051] This results in a particularly good protective effect against secondary and quaternary carbon atoms due to the presence of the compound in rubber compounds, in particular for vehicle tires and other technical rubber articles, and in particular an optimized reactivity in connection with the mechanisms relevant for ageing protection, whereby undesirable side reactions are avoided.

[0052] According to further advantageous embodiments, R1 , in particular in the above-mentioned formulas I), II), la), Ha), is a branched or cyclic alkyl radical having three to twelve carbon atoms, preferably three to eight carbon atoms, where R 1 is particularly preferably selected from 1,3-dimethylbutyl and

[0053] Cyclohexyl residues, where R 1 most preferably a 1,3-dimethylbutyl radical.

[0054] This achieves particularly good solubility in rubber compounds for vehicle tires and other technical rubber articles.

[0055] According to a particularly advantageous embodiment, the compound according to the invention has the structure according to formula III):

[0056] The compound according to formula III) exhibits sufficient solubility in polymers, particularly in rubber compounds for vehicle tires and other technical rubber articles. At the same time, the compound according to formula II) can be produced particularly easily and in an energy- and cost-saving manner, and, compared to 6PPD, exhibits comparable or even improved solubility.

[0057] Oxidation protection, especially at temperatures above 150 °C, and thus a comparable or improved anti-aging effect.

[0058] The compound according to formula III) can also be defined according to IPIIAC as

[0059] 2-(1,3-Dimethylbutylamino)-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one. A further subject of the present invention, as stated above, is a process for preparing the compound according to formula I), which comprises at least the following process steps: i) preparing or providing the substance according to formula B1): ii) reaction of the compound according to formula B1 ) with hydrogen and a ketone or aldehyde, preferably ketone, to give the compound according to formula I): where R 1 is selected from the group consisting of xi) aromatic radicals, wherein the aromatic radicals optionally carry substituents selected from the group consisting of halogen radicals, cyano radicals, ester radicals, ketone radicals, ether radicals and thioether radicals, and xii) linear, branched and cyclic aliphatic C3 to C12 radicals, wherein the radicals R 2 and R 3can independently of one another be the same or different and are selected from the group consisting of linear, branched and cyclic, saturated and unsaturated, aliphatic C 1 to C 12 radicals, which optionally carry one or more halogen substituents, aryl radicals which optionally carry one or more halogen substituents, and halogen radicals, with fluorine, bromine and chlorine being preferred, cyano radicals, ester radicals, ketone radicals, ether radicals and thioether radicals; and where m takes the value 0 or 1 or 2 or 3, and where n takes the value 0 or 1 or 2 or 3 or 4, where X is selected from 0 (oxygen atom), S (sulfur atom) and N(H) (secondary amino group), where Y is selected from 0 (oxygen atom), S (sulfur atom) and N(H) (secondary amino group).

[0060] For R 1 , R 2 , R 3, X, Y, m and n, all the above statements made in connection with the description of the compound according to the invention apply, including preferred embodiments and with regard to the possibilities of any gradation in the preference of these features and the combinations of these features.

[0061] The compound according to formula B1 ) can be prepared for X equal to N(H) (secondary amino group) and Y equal to 0 (oxygen atom), for example analogously to US 6919328 according to the following scheme S1 ): where TEA stands for triethylamine and DMSO stands for dimethyl sulfoxide.

[0062] The group -N(H)R is preferred 1 or in the starting substance the group -NO2 is arranged in meta-position to X, as already explained above.

[0063] Thus, the compound prepared according to the invention preferably has the structure according to formula II):

[0064] For this purpose, the starting substance according to formula B1 ) preferably has the structure according to formula B1 a):

[0065] B1 a) where R 1 , R 2 , R 3 , X and Y as well as m and n are as defined above, including all embodiments and combinations of features.

[0066] Here too, according to preferred embodiments, X is equal to N(H) and Y is equal to 0.

[0067] Preferably, a suitable catalyst, referred to in the present invention as “hydrogenation catalyst”, is used in the reaction with hydrogen in step ii).

[0068] The hydrogenation catalyst is preferably a noble metal catalyst, such as palladium (Pd) or platinum (Pt). The noble metal is preferably used on carbon (C), such as palladium on carbon (Pd / C).

[0069] Furthermore, other known catalysts such as Raney nickel or copper chromite can also be used.

[0070] The reaction in step ii) is particularly preferably carried out with hydrogen, using a hydrogenation catalyst. The reaction in step ii) is preferably carried out at a temperature of 50 to 130°C, preferably 50 to 100°C, particularly preferably 50 to 80°C, in particular, for example, 60°C.

[0071] Hydrogen is preferably injected at a pressure of 30 to 70 bar, particularly preferably 35 to 45 bar, in particular for example 40 bar, and is then preferably stirred for 1 to 20 hours, preferably 3 to 13 hours, particularly preferably 5 to 13 hours, in particular for example 10 hours.

[0072] Preferably, the reaction with hydrogen in step ii) takes place in a container suitable for the preferably comparatively high pressure, such as in particular in an autoclave or in another pressure reactor.

[0073] Particularly preferably, the reaction in step ii) is carried out with hydrogen using a hydrogenation catalyst and at a temperature of 50 to 130 °C, preferably 50 to 100 °C, particularly preferably 50 to 80 °C, and wherein hydrogen is injected at a pressure of 30 to 70 bar, particularly preferably 35 to 45 bar, in particular for example 40 bar, and the reaction takes place in an autoclave or in another pressure reactor.

[0074] The ketone in step ii) is the ketone derivative of the later residue R 1 ; In the case of an aldehyde, the aldehyde derivative is used.

[0075] For simplicity, the formula R is abbreviated 1 =O is used for the aldehyde or ketone, since the residue R 1 is the part that remains on the nitrogen atom after reaction with the aldehyde or ketone.

[0076] The ketone methyl isobutyl ketone is preferably used.

[0077] The solvent in step ii) can be either the ketone or aldehyde when in liquid form, or an inert solvent such as toluene or xylene, particularly when the ketone or aldehyde is in solid form. In the latter case, the ketone or aldehyde is used as a reactant only in stoichiometric amounts. Preference is given to a ketone or aldehyde R 1 =O, particularly preferably ketone, is used in liquid form as a solvent. This eliminates the need for an additional substance such as toluene or xylene.

[0078] Preferably, following step ii), purification is carried out, for example by filtration and washing with a solvent, in particular ethanol, and / or by column chromatography, for example on silica gel or by recrystallization from cyclohexane or higher-chain aliphatics.

[0079] A further subject of the invention is, as stated above, a rubber mixture.

[0080] The rubber mixture according to the invention contains the compound according to formula I), for example and preferably the compound according to formula III). The rubber mixture according to the invention can in principle be any rubber mixture, in particular in which the novel compound according to the invention according to formula I) or III) acts as an ageing inhibitor and / or antiozonant with lower toxicity.

[0081] The rubber mixture according to the invention contains at least one rubber.

[0082] The rubber mixture according to the invention preferably contains 0.1 to 10 phr, particularly preferably 0.1 to 7 phr, very particularly preferably 1 to 6 phr, again preferably 1 to 3 phr, of the compound according to formula I), for example and preferably the compound according to formula III).

[0083] The rubber mixture may also contain a mixture of several compounds falling under formula I).

[0084] The term phr (parts per hundred parts of rubber by weight) used in this document is the standard quantity used in the rubber industry for compound formulations. 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 (M) components present in the compound. w greater than 20,000 g / mol) rubbers.

[0085] According to advantageous embodiments of the invention, the rubber mixture according to the invention contains at least one diene rubber. The rubber mixture can thus contain one diene rubber or a mixture of two or more different diene rubbers.

[0086] Diene rubbers are rubbers that are produced by polymerization or copolymerization of dienes and / or cycloalkenes and thus have C=C double bonds either in the main chain or in the side groups.

[0087] The diene rubber is preferably selected from the group consisting of natural polyisoprene (NR), synthetic polyisoprene (IR), epoxidized polyisoprene (ENR), butadiene rubber (BR), butadiene-isoprene rubber, solution-polymerized styrene-butadiene rubber (SSBR), emulsion-polymerized styrene-butadiene rubber (ESBR), styrene-isoprene rubber, liquid rubbers with a molecular weight M w greater than 20,000 g / mol, halobutyl rubber, polynorbornene, isoprene-isobutylene copolymer, ethylene-propylene-diene rubber, nitrile rubber, chloroprene rubber, acrylate rubber, fluororubber, silicone rubber, polysulfide rubber, epichlorohydrin rubber, styrene-isoprene-butadiene terpolymer, hydrogenated acrylonitrile-butadiene rubber and hydrogenated styrene-butadiene rubber.

[0088] In particular, nitrile rubber, hydrogenated acrylonitrile-butadiene rubber, chloroprene rubber, butyl rubber, halobutyl rubber, and / or ethylene-propylene-diene rubber are used in the production of technical rubber articles, such as belts, straps, and hoses, and / or shoe soles. The preferred blend compositions for these rubbers—specific with regard to fillers, plasticizers, vulcanization systems, and additives—are known to those skilled in the art. The natural and / or synthetic polyisoprene in all embodiments can be either cis-1,4-polyisoprene or 3,4-polyisoprene. However, the use of cis-1,4-polyisoprenes with a cis-1,4 content of > 90 wt.% is preferred. 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 wt.%.

[0089] Furthermore, a mixture of one or more natural polyisoprenes with one or more synthetic polyisoprene(s) is also conceivable.

[0090] For the purposes of the present invention, the term "natural rubber" refers to naturally occurring rubber that can be obtained from Hevea rubber trees and non-Hevea sources. Non-Hevea sources include, for example, guayule shrubs and dandelions such as TKS (Taraxacum kok-saghyz; Russian dandelion).

[0091] If butadiene rubber (= BR, polybutadiene) is present in the rubber mixture according to the invention, it can be any type known to the person skilled in the art. These include, among others, the so-called high-cis and low-cis types, with polybutadiene with a cis content greater than or equal to 90 wt. % being referred to as the high-cis type and polybutadiene with a cis content less than 90 wt. % being referred to as the low-cis type. An example of a low-cis polybutadiene is Li-BR (lithium-catalyzed butadiene rubber) with a cis content of 20 to 50 wt. High-cis BR achieves particularly good properties and low hysteresis of the rubber mixture.

[0092] The polybutadiene(s) used can be end-group modified and / or functionalized along the polymer chains. The modifications can be 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 carboxyl groups and / or phthalocyanine groups and / or silane sulfide groups. However, other modifications known to the person skilled in the art, also referred to as functionalizations, are also possible. Metal atoms can be a component of such functionalizations.

[0093] If at least one styrene-butadiene rubber (styrene-butadiene copolymer) is present in the rubber mixture, it can be either solution-polymerized styrene-butadiene rubber (SSBR) or emulsion-polymerized styrene-butadiene rubber (ESBR), although a mixture of at least one SSBR and at least one ESBR can also be used. The terms "styrene-butadiene rubber" and "styrene-butadiene copolymer" are used synonymously in the present invention.

[0094] 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.

[0095] Preferably, the at least one diene rubber is selected from the group consisting of natural polyisoprene (NR, natural rubber), synthetic polyisoprene (IR), butadiene rubber (BR), solution-polymerized styrene-butadiene rubber (SSBR), emulsion-polymerized styrene-butadiene rubber (ESBR), butyl rubber (HR) and halobutyl rubber.

[0096] According to a particularly preferred embodiment of the invention, the at least one diene rubber is selected from the group consisting of natural polyisoprene (NR), synthetic polyisoprene (IR), butadiene rubber (BR), solution-polymerized styrene-butadiene rubber (SSBR) and emulsion-polymerized styrene-butadiene rubber (ESBR).

[0097] According to a particularly advantageous embodiment of the invention, the rubber mixture contains at least one natural polyisoprene (NR), preferably in amounts of 50 to 100 phr, and according to a particularly advantageous embodiment of the invention, 80 to 100 phr, very particularly preferably 95 to 100 phr, again preferably 100 phr. Such a rubber mixture exhibits, in particular, optimized tear properties and abrasion properties with good processability and reversion stability.

[0098] In the event that the rubber mixture contains less than 100 phr NR, it preferably contains as further rubber at least one diene rubber selected from the group consisting of synthetic polyisoprene (IR), butadiene rubber (BR), solution-polymerized styrene-butadiene rubber (SSBR) and emulsion-polymerized styrene-butadiene rubber (ESBR).

[0099] According to a further particularly advantageous embodiment of the invention, the rubber mixture contains at least one natural polyisoprene (NR), preferably in amounts of 5 to 55 phr, and according to a particularly advantageous embodiment of the invention, 5 to 25 phr, very particularly preferably 5 to 20 phr. Such a rubber mixture exhibits, in particular, good processability and reversion stability as well as optimized tear properties and optimal rolling resistance behavior.

[0100] According to a further particularly advantageous embodiment of the invention, the rubber mixture contains at least one polybutadiene (BR, butadiene rubber), preferably in amounts of 10 to 80 phr, particularly preferably 10 to 50 phr, and according to a particularly advantageous embodiment of the invention 15 to 40 phr. This achieves particularly good tear and abrasion properties of the rubber mixture according to the invention and optimal braking behavior.

[0101] According to a further particularly advantageous embodiment of the invention, the rubber mixture contains at least one solution-polymerized styrene-butadiene rubber (SSBR), preferably in amounts of 10 to 80 phr, particularly preferably 30 to 80 phr, and according to a particularly advantageous embodiment of the invention 50 to 70 phr. This achieves particularly good rolling resistance properties of the rubber mixture according to the invention. According to particularly advantageous embodiments of the invention, SSBR is used in combination with at least one other rubber in order to achieve an optimal and balanced property profile. The rubber mixture preferably contains at least one filler, preferably in amounts of 30 to 500 phr, particularly preferably 50 to 400 phr, again preferably 80 to 300 phr.

[0102] According to advantageous embodiments of the invention, the filler is a reinforcing filler, which is preferably selected from the group consisting of carbon black and silicon dioxide.

[0103] Suitable carbon blacks include all types of carbon black known to those skilled in the art. The carbon black is preferably selected from industrial carbon blacks and pyrolysis carbon blacks, with industrial carbon blacks being even more preferred.

[0104] The carbon black preferably has an iodine number according to ASTM D 1510, which is also referred to as iodine adsorption number, between 30 and 250 g / kg, preferably 30 to 180 g / kg, more preferably 40 to 180 g / kg, and most preferably 40 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, more preferably 90 to 200 ml / 100 g.

[0105] The DBP number according to ASTM D 2414 determines the specific absorption volume of a carbon black or a light filler using dibutyl phthalate.

[0106] The use of such a type of carbon black in the rubber compound, especially for vehicle tires, ensures the best possible compromise between abrasion resistance and heat build-up, which in turn influences the ecologically relevant rolling resistance.

[0107] Particularly suitable and preferred is a carbon black with an iodine adsorption number between 80 and 110 g / kg and a DBP number of 100 to 130 ml / 100g, such as in particular carbon black of type N339.

[0108] The silicon dioxide is preferably amorphous silicon dioxide, for example, precipitated silica, also known as precipitated silicon dioxide. Alternatively, pyrogenic silicon dioxide, for example, can also be used.

[0109] However, it is particularly preferred to use a finely divided, precipitated silica which has a nitrogen surface area (BET surface area) (according to DIN ISO 9277 and DIN 66132) of 35 to 400 m 2 / g, preferably from 35 to 350 m 2 / g, particularly 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) of 30 to 400 m 2 / g, preferably from 30 to 330 m 2 / g, particularly preferably from 80 to 300 m 2 / g and most preferably from 115 to 200 m 2 / g. Such silicas, for example, lead to particularly good physical properties of the vulcanizates in rubber compounds for tire treads. Furthermore, they can offer advantages in compound processing by reducing mixing times while maintaining consistent product properties, leading to improved productivity. Thus, both Ultrasil® VN3 (trade name) from Evonik and highly dispersible silicas, so-called HD silicas (e.g., Zeosil® 1165 MP from Solvay), can be used as silicas.

[0110] According to particularly advantageous embodiments of the invention, the rubber mixture contains at least one silica as filler, preferably in amounts of 30 to 500 phr, particularly preferably 50 to 400 phr, again preferably 80 to 300 phr.

[0111] In these quantities, silica is contained in particular as the sole or main filler (more than 50% by weight based on the total filler quantity).

[0112] According to further advantageous embodiments of the invention, the rubber mixture contains at least one silica as a further filler, preferably in amounts of 5 to 100 phr, particularly preferably 5 to 80 phr, again preferably 10 to 60 phr.

[0113] In these amounts, silica is included in particular as an additional filler in addition to another main filler, such as in particular a carbon black.

[0114] The terms “silicic acid” and “silica” are used synonymously in the present invention.

[0115] According to particularly advantageous embodiments of the invention, the rubber mixture according to the invention contains 0.1 to 60 phr, preferably 3 to 40 phr, more preferably 5 to 30 phr, most preferably 5 to 15 phr, of at least one carbon black. In these amounts, carbon black is present in particular as a further filler in addition to a main filler, such as, in particular, silica.

[0116] According to further advantageous embodiments of the invention, the rubber mixture according to the invention contains 30 to 300 phr, preferably 30 to 200 phr, particularly preferably 40 to 100 phr of at least one carbon black. In these amounts, carbon black is present as the sole or main filler, optionally in combination with silica in the above-mentioned smaller amounts.

[0117] According to a particularly advantageous embodiment of the invention, the rubber mixture contains 5 to 60 phr, particularly preferably 5 to 40 phr, of at least one carbon black and 50 to 300 phr, preferably 80 to 200 phr of at least one silica.

[0118] The rubber mixture may also contain additional fillers that may or may not have a reinforcing effect.

[0119] Other (non-reinforcing) fillers within the scope of the present invention include aluminosilicates, kaolin, chalk, starch, magnesium oxide, titanium dioxide or rubber gels as well as fibers (such as aramid fibers, glass fibers, carbon fibers, cellulose fibers).

[0120] Other potentially reinforcing fillers include carbon nanotubes (CNTs) including discrete CNTs, so-called hollow carbon fibers (HCFs) and modified CNTs containing one or more functional groups such as hydroxyl, carboxy and carbonyl groups), graphite and graphene and so-called “carbon-silica dual-phase fillers”.

[0121] Zinc oxide is not considered a filler in the context of the present invention.

[0122] Furthermore, the rubber mixture may contain conventional additives in the usual parts by weight, which are preferably added in at least one basic mixing stage during its production. These additives include a) anti-aging agents known in the art, such as p-phenylenediamines, such as

[0123] N-Phenyl-N'-(1,3-dimethylbutyl)-p-phenylenediamine (6PPD), N,N'-diphenyl-p-phenylenediamine (DPPD),

[0124] N-(1 -phenylethyl)-N’-phenyl-p-phenylendiamin (SPPD), N,N‘-Ditolyl-p-phenylendiamin (DTPD),

[0125] N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD), N-isopropyl-N'-phenyl-p-phenylenediamine (IPPD), or dihydroquinolines, such as 2,2,4-trimethyl-1,2-dihydroquinoline (TMQ), b) activators, such as 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 the bonding of fillers, in particular carbon black or silica, such as S-(3-aminopropyl)thiosulphuric acid and / or its metal salts (bonding to carbon black) and silane coupling agents (bonding to silicon dioxide, in particular silica), d) ozone protection waxes, e) resins, in particular tackifying resins, f) mastication aids, such as B. 2,2'-Dibenzamidodiphenyl disulfide (DBD) and g) processing aids, such as in particular fatty acid esters and metal soaps, such as zinc soaps and / or calcium soaps h) plasticizers, such as in particular aromatic, naphthenic or paraffinic mineral oil plasticizers, such asMES (mild extraction solvate) or RAE (residual aromatic extract) or TDAE (treated distillate aromatic extract), or rubber-to-liquid oils (RTL) or biomass-to-liquid oils (BTL), preferably with a polycyclic aromatics content of less than 3% by weight according to method IP 346, or triglycerides, such as rapeseed oil, or factices or hydrocarbon resins or liquid polymers whose average molecular weight (determined by GPC = gel permeation chromatography, based on BS ISO 11344:2004) is between 500 and 20,000 g / mol.

[0126] When using mineral oil, it is preferably selected from the group consisting of DAE (Distilled Aromatic Extracts), RAE (Residual Aromatic Extracts), TDAE (Treated Distilled Aromatic Extracts), MES (Mild Extracted Solvents), and naphthenic oils. According to particularly advantageous embodiments, the rubber mixture according to the invention contains, in addition to the compound according to the invention according to formula I), for example according to formula III), no anti-aging agents from the group of p-phenylenediamines, in particular those under list a) above.In particular, according to a particularly preferred embodiment, the rubber mixture according to the invention contains 0 to 0.1 phr, in particular 0 phr, of further ageing inhibitors based on p-phenylenediamines, which are selected from the group containing, preferably consisting of, N-phenyl-N'-(1,3-dimethylbutyl)-p-phenylenediamine (6PPD), N-(1-phenylethyl)-N'-phenyl-p-phenylenediamine (SPPD), N,N'-diphenyl-p-phenylenediamine (DPPD), N,N'-ditolyl-p-phenylenediamine (DTPD), N-isopropyl-N'-phenyl-p-phenylenediamine (IPPD), N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD).

[0127] With the preferably very small amounts of 0 to 0.1 phr, or particularly preferably 0 phr, of p-phenylenediamines, and the compound according to formula I), for example according to formula III), contained according to the invention, it is possible to achieve a comparable protective effect with lower toxicity. The compound according to formula I), for example according to formula III), according to the invention replaces the aforementioned p-phenylenediamines known in the prior art.

[0128] According to further advantageous embodiments of the invention, at least one further of the aforementioned p-phenylenediamine antioxidants is also present, so that the compound according to the invention only partially replaces the p-phenylenediamines known in the prior art. This also achieves the advantage of the invention, but not to an optimal extent.

[0129] According to advantageous embodiments, antiaging agents based on dihydroquinoline, such as TMQ, are present in the rubber mixture in addition to the compound of formula I) according to the invention. The amount of dihydroquinolines present, such as TMQ in particular, is preferably 0.1 to 3, in particular 0.5 to 1.5 phr. Ozone protection waxes (group d above) are considered separately and are present in the rubber mixture according to preferred embodiments of the invention, regardless of whether additional antiaging agents a) are present.

[0130] The silane coupling agents can be any type known to the person skilled in the art.

[0131] Furthermore, one or more different silane coupling agents can be used in combination. The rubber compound can thus contain a mixture of different silanes.

[0132] The silane coupling agents react with the surface silanol groups of the silicon dioxide, in particular the silica, or other polar groups during the mixing of the rubber or the rubber mixture (in situ) or even before the addition of the filler to the rubber in the sense of a pretreatment (premodification).

[0133] Coupling agents known from the prior art are bifunctional organosilanes that have at least one alkoxy, cycloalkoxy, or phenoxy group as a leaving group on the silicon atom and that have, as another functionality, a group that, if necessary after cleavage, can enter into a chemical reaction with the double bonds of the polymer. The latter group can be, for example, the following chemical groups: -SCN, -SH, -NH2, or -S x - (with x = 2 to 8).

[0134] For example, 3-mercaptopropyltriethoxysilane, 3-thiocyanatopropyltrimethoxysilane, or 3,3'-bis(triethoxysilylpropyl)polysulfides with 2 to 8 sulfur atoms, such as 3,3'-bis(triethoxysilylpropyl)tetrasulfide (TESPT), the corresponding disulfide (TESPD), or mixtures of sulfides with 1 to 8 sulfur atoms with varying contents of the various sulfides, can be used as silane coupling agents. TESPT can also be added, for example, as a mixture with carbon black (trade name X50S® from Evonik).

[0135] Blocked mercaptosilanes, such as those known from WO 99 / 09036, can also be used as silane coupling agents. Silanes such as those described in WO 2008 / 083241 A1, WO 2008 / 083242 A1, WO 2008 / 083243 A1, and WO 2008 / 083244 A1 can also be used. Examples of suitable silanes include those sold under the name NXT in various variants by Momentive, USA, such as 3-octanoylthio-1-propyltriethoxysilane, or those sold under the name VP Si 363® by Evonik Industries.

[0136] The proportion of the total amount of further additives is preferably 3 to 150 phr, particularly preferably 3 to 100 phr and most preferably 5 to 80 phr.

[0137] The total amount of other additives may contain zinc oxide (ZnO) in the amounts stated above.

[0138] This can be any type of zinc oxide known to the person skilled in the art, such as ZnO granules or powder. The zinc oxide commonly used usually has a BET surface area of ​​less than 10 m 2 / g. However, it can also be a zinc oxide with a BET surface area of ​​10 to 100 m 2 / g, such as so-called “nano-zinc oxides”, can be used.

[0139] The rubber mixture according to the invention is preferably used in vulcanized form, in particular in vehicle tires or other vulcanized technical rubber articles.

[0140] The terms “vulcanized” and “crosslinked” are used synonymously in the context of the present invention.

[0141] The vulcanization of the rubber mixture according to the invention is preferably carried out in the presence of sulfur and / or sulfur donors using vulcanization accelerators, whereby some vulcanization accelerators can also act as sulfur donors. The accelerator is selected from the group consisting of thiazole accelerators, mercapto accelerators, sulfenamide accelerators, thiocarbamate accelerators, thiuram accelerators, thiophosphate accelerators, thiourea accelerators, xanthate accelerators, and guanidine accelerators. Preferred is the use of a sulfenamide accelerator selected from the group consisting of N-cyclohexyl-2-benzothiazolesufenamide (CBS), N,N-dicyclohexylbenzothiazole-2-sulfenamide (DCBS), benzothiazyl-2-sulfenemorpholide (MBS), N-tert-butyl-2-benzothiazylsulfenamide (TBBS) and guanidine accelerators such as diphenylguanidine (DPG).

[0142] All sulfur-donating substances known to the person skilled in the art can be used as sulfur-donating substances.

[0143] In addition, vulcanization retarders may be present in the rubber compound.

[0144] The rubber compound is preferably produced using the process commonly used in the rubber industry, in which a base compound containing all components except the vulcanization system (e.g., sulfur and vulcanization-influencing substances) is first prepared in one or more mixing stages. The finished compound is created by adding the vulcanization system in a final mixing stage.

[0145] The finished mixture is further processed, for example, by an extrusion process or calendering and brought into the appropriate shape.

[0146] The rubber mixture according to the invention is particularly suitable for use in vehicle tires, especially pneumatic vehicle tires. Application is conceivable in principle in all tire components, especially in an outer component, particularly and preferably in the flange profile, tread, and / or sidewall. In the case of a tread with a cap / base construction, the rubber mixture according to the invention is preferably used at least in the cap.

[0147] For use in vehicle tires, the mixture is molded into the appropriate shape, preferably an outer component, as a ready-mixed product prior to vulcanization and applied during the production of the green vehicle tire as known. The rubber mixture according to the invention for use as a body compound in vehicle tires is produced as already described. The difference lies in the shaping after the extrusion process or calendering of the mixture. The resulting shapes of the still unvulcanized rubber mixture for one or more different body compounds are then used to construct a green tire.

[0148] The term body compound refers to the rubber compounds for the inner components of a tire, such as the squeegee, inner liner (inner layer), core tread, belt, shoulder, belt tread, carcass, bead reinforcement, bead tread, horn tread and bandage.

[0149] The unvulcanized tire blank is then vulcanized.

[0150] For use of the rubber mixture according to the invention in belts and straps, particularly conveyor belts, the extruded, still unvulcanized mixture is molded into the appropriate shape and, during or afterward, often provided with reinforcements, e.g., synthetic fibers or steel cords. This usually results in a multi-layer structure consisting of one or more layers of rubber mixture, one or more layers of the same and / or different reinforcements, and one or more additional layers of the same and / or a different rubber mixture.

[0151] A further subject of the present invention is a vehicle tire which comprises the rubber mixture according to the invention containing the compound according to the invention in at least one component.

[0152] The vulcanized vehicle tire comprises, at least in one component, a vulcanizate of at least one rubber mixture according to the invention. Those skilled in the art are aware that most substances, such as the rubbers contained therein, are or can be present in a chemically altered form either after mixing or only after vulcanization. For the purposes of the present invention, vehicle tires are understood to mean pneumatic vehicle tires and solid rubber tires, including tires for industrial and construction vehicles, truck tires, passenger car tires, and two-wheeled tires.

[0153] The vehicle tire according to the invention preferably comprises the rubber mixture according to the invention in at least one outer component, wherein the outer component is preferably a tread, a sidewall and / or a horn profile.

[0154] The vehicle tire according to the invention can thus also comprise the rubber mixture according to the invention containing the compound according to the invention according to formula I) in several components in an optionally adapted composition.

[0155] In the following, the invention will be explained in more detail using exemplary embodiments.

[0156] The compound according to formula III) as an exemplary embodiment of the compound according to formula I) was prepared in the following manner as shown in Schemes S1a) and S2):

[0157] S1a) the synthesis according to S1 a) was carried out according to US 6919328.

[0158] Synthesis of

[0159] 2-(1,3-Dimethylbutylamino)-5,10-dihvdro-dibenzo[b,e][1,4]diazepin-11-one

[0160] (Compound according to formula III):

[0161] In a stainless steel autoclave equipped with a Teflon liner, 0.30 g (1.12 mmol, 1 equivalent (eq))

[0162] 2-Nitro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one, 0.10 g of platinum on carbon (Pt / C) (5%) (0.4 g per 4.67 mmol of substrate), and 20.0 mL of methyl isobutyl ketone (MIBK) were weighed in. The mixture was then pressurized to 40 bar of hydrogen (H2) and stirred at 60°C for 10 hours. After the reaction was complete, the excess hydrogen was vented, and the suspension was filtered through Celite® and rinsed with ethanol. The filtrate was evaporated to dryness and dried under vacuum. The product was purified by column chromatography (cyclohexane / ethyl acetate). Brownish solid; yield 0.18 g (50% of theory).

[0163] 1H-NMR (nuclear magnetic resonance) (500 MHz, DMSO-c / 6) Ö = 9.72 (s, 1 H), 7.20 (s, 1 H), 6.97 - 6.82 (m, 5H), 6.77 (d, J = 8.5 Hz, 1 H), 6.63 (dd, J = 8.6, 2.9 Hz, 1 H), 5.00 (d, J = 8.3 Hz, 1 H), 3.31 (s, 1 H), 1 .71 (ie, J = 13.4, 6.5 Hz, 1 H), 1 .44 - 1 .32 (m, 5H), 1.18 (dt, J = 13.8, 6.9 Hz, 1 H), 1 .03 (d, J = 6.2 Hz, 3H), 0.89 (d, J = 6.6 Hz, 3H), 0.85 (d, J = 6.6 Hz, 3H).

[0164] ESI-MS (electrospray ionization mass spectrometry) [M+H] + = 310.

[0165] Measurement of the oxidation induction time (PIT)

[0166] The compound according to formula III) was investigated for its potential protective effect as an anti-aging agent by measuring the oxidation induction time under laboratory conditions.

[0167] For this purpose, the compounds according to formula III) and 6PPD were each combined with a polymer (liquid synthetic polyisoprene (IR), LIR-50, Kuraray, weight average molecular weight distribution M w = 54,000 g / mol, glass transition temperature T g = -63°C) was heated at three different temperatures (180°C; 165°C; 150°C) at constant temperature until oxidation occurred. Heating to 180°C was carried out as follows:

[0168] Starting temperature 35 °C, heating to 170 °C at a heating rate of 20 K / min (Kelvin per minute), heating to 180 °C at a heating rate of 1 K / min; purge gas: nitrogen (N2) with a volume flow of 50 mL / min).

[0169] The sample was kept isothermally under N2 atmosphere at 180°C for 5 minutes and then switched to O2 atmosphere (with a flow rate of 50 mL / min).

[0170] Heating to 165 °C was carried out analogously, with heating first to 155 °C at a heating rate of 20 K / min (Kelvin per minute) and then to 165 °C at a heating rate of 1 K / min.

[0171] Heating to 150 °C was carried out analogously, with heating first to 140 °C at a heating rate of 20 K / min (Kelvin per minute) and then to 150 °C at a heating rate of 1 K / min.

[0172] Oxidation was determined via a peak in each case using DSC (differential scanning calorimetry).

[0173] The time until oxidation was measured in minutes.

[0174] The results are summarized in Table 1 in comparison to the known anti-aging agent 6PPD.

[0175] Table 1

[0176] Taking into account the measurement accuracy of ± (plus or minus) 10 minutes, it can be seen that the compound according to formula III) achieves an improved protective effect compared to 6PPD at temperatures above 150 °C, since it takes significantly longer for oxidation to occur.

[0177] At 150 °C, oxidation takes too long, so the experiments were terminated after 900 minutes. Therefore, no experimental difference has been determined between 6PPD and the compound according to formula III).

[0178] Thus, the compound according to the invention according to formula III) as a representative of the compound according to the invention according to formula I) is more environmentally and health-friendly than 6PPD or other representatives of the substance class, as stated at the beginning, and is also a comparable or even better anti-aging agent.

[0179] At the same time, the compound according to formula III), as a representative of the compound according to formula I), exhibits sufficient solubility in rubber mixtures. This minimizes blooming, which in turn has a beneficial effect on the protective effect.

[0180] With the compound according to formula I), an overall improved protective effect can be achieved in the applications mentioned.

[0181] For use in a rubber mixture for vehicle tires, the compound according to the invention according to formula I), for example according to formula III), is added, for example instead of the anti-aging agents known in the prior art, such as 6PPD, 7PPD or IPPD, etc., in a manner known to the person skilled in the art in one of the mixing stages during the preparation of the rubber mixture.

[0182] For this purpose, the compound according to formula III) is mixed in various amounts, as shown in Table 2. The resulting examples according to the invention are marked E1 and E2.

[0183] For comparison, rubber compounds containing 6PPD instead of the compound according to formula III) as an antioxidant are used, with otherwise identical compositions, whereby an equal molar exchange occurs between V1 and E1 and between V2 and E2. The amounts in Table 2 are given in phr. A reference (Ref.) without antioxidant is also given. For all compounds, the sum of the amounts of antioxidant (6PPD or formula III) and plasticizer oil MES is 10 phr.

[0184] Table 2

[0185] The examples according to the invention show a comparable or even improved anti-aging effect compared to rubber mixtures with 6PPD.

Claims

Patent claims 1. Compound according to formula I): where R 1 selected from the group consisting of xi) aromatic residues, wherein the aromatic residues optionally bear substituents selected from the group consisting of halogen residues, cyano residues, ester residues, ketone residues, ether residues and thioether residues, and xii) linear, branched and cyclic aliphatic C3 to C12 residues, wherein the residues R 2 and R 3can be the same or different independently of one another and are selected from the group consisting of linear, branched and cyclic, saturated and unsaturated, aliphatic Ci to C-12 residues, which optionally bear one or more halogen substituents, aryl residues which optionally bear one or more halogen substituents, and halogen residues, wherein fluorine, bromine and chlorine are preferred, cyano residues, ester residues, ketone residues, ether residues and thioether residues; and wherein m takes the value 0 or 1 or 2 or 3, and wherein n takes the value 0 or 1 or 2 or 3 or 4, wherein X is selected from 0 (oxygen atom), S (sulfur atom) and N(H) (secondary amino group), and wherein Y is selected from 0 (oxygen atom), S (sulfur atom) and N(H) (secondary amino group).

2. Compound according to claim 1, characterized in that it has the structure according to formula II): where R 1 , R 2 , R 3, X and Y as well as m and n as defined for claim 1.

3. Compound according to one of claims 1 or 2, characterized in that X is equal to NH.

4. Compound according to one of the preceding claims, characterized in that Y is equal to 0.

5. Compound according to one of the preceding claims, characterized in that m is equal to zero (0) and / or n is equal to zero (0).

6. Compound according to one of the preceding claims, characterized in that R 1 is bonded to the nitrogen atom (N) via a tertiary carbon atom.

7. Compound according to one of the preceding claims, characterized in that R 1 a branched or cyclic alkyl group with 3 to 12 carbon atoms, preferably 3 to 8 carbon atoms.

8. Compound according to one of the preceding claims, characterized in that R 1 selected from 1,3-dimethylbutyl and cyclohexyl residues, where R1 preferably a 1,3-dimethylbutyl residue.

9. Compound according to one of the preceding claims, characterized in that it has the structure according to formula III):

10. Rubber mixture comprising the compound according to any one of claims 1 to 9, wherein the rubber mixture preferably comprises at least one diene rubber, which is particularly preferably selected from the group consisting of natural polyisoprene (NR), synthetic polyisoprene (IR), butadiene rubber (BR), solution polymerized styrene-butadiene rubber (SSBR), emulsion polymerized styrene-butadiene rubber (ESBR), butyl rubber (HR) and halobutyl rubber.

11. Vehicle tire comprising the rubber compound according to claim 10 in at least one component, preferably in at least one outer component, wherein the outer component is preferably a tread, a sidewall and / or a horn profile.

12. Use of the compound according to any one of claims 1 to 9 as an anti-aging agent and / or ozone protection agent, particularly in vehicle tires and / or other technical rubber articles, such as, in particular, an air spring, a bellows, a conveyor belt, a belt, a hose, a rubber band, a profile, a seal, a membrane, tactile sensors for medical applications or robotic applications, or a shoe sole or parts thereof, and / or oils and / or lubricants.

13. Use of the compound according to any one of claims 1 to 9 for the manufacture of a rubber article, in particular an air spring, a bellows, a conveyor belt, a belt, a hose, a rubber band, a profile, a seal, a membrane, tactile sensors for medical applications or robotic applications, or a shoe sole or parts thereof.

14. Use of the compound according to any one of claims 1 to 9 as a dye in fibers and / or polymers and / or paper and / or in (coating) paints and varnishes.

15. Method for producing the compound according to Formula I), comprising at least the following process steps: i) Producing or providing the substance according to Formula B1): ii) Reaction of the compound according to formula B1 ) with hydrogen and a ketone or aldehyde, preferably ketone, to give the compound according to formula I): where R 1 selected from the group consisting of xi) aromatic residues, wherein the aromatic residues optionally bear substituents selected from the group consisting of halogen residues, cyano residues, ester residues, ketone residues, ether residues and thioether residues, and xii) linear, branched and cyclic aliphatic C3 to C12 residues, wherein the residues R 2 and R 3which can be identical or different independently of one another and are selected from the group consisting of linear, branched and cyclic, saturated and unsaturated, aliphatic Ci to C-12 residues, which optionally bear one or more halogen substituents, aryl residues, which optionally bear one or more halogen substituents, and halogen residues, wherein fluorine, bromine and chlorine are preferred, cyano residues, ester residues, ketone residues, ether residues and thioether residues; and wherein m takes the value 0 or 1 or 2 or 3, and wherein n takes the value 0 or 1 or 2 or 3 or 4, wherein X is selected from 0 (oxygen atom), S (sulfur atom) and N(H) (secondary amino group), and wherein Y is selected from 0 (oxygen atom), S (sulfur atom) and N(H) (secondary amino group).

16. The method of claim 15, wherein the reaction in step ii) is carried out with hydrogen using a hydrogenation catalyst and / or at a temperature of 50 to 130 °C, preferably 50 to 100 °C, particularly preferably 50 to 80 °C, and / or hydrogen is forced in at a pressure of 30 to 70 bar, particularly preferably 35 to 45 bar, in particular for example 40 bar, and the reaction takes place in an autoclave or in another pressure reactor.

17. Method according to one of claims 15 or 16, characterized in that the compound according to formula I) has the structure according to formula II): and wherein the substance according to formula B1 ) has the structure according to formula B1 a): where R 1 , R 2 , R 3 , X and Y as well as m and n as defined for claim 15.

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