Compounds as anti-aging agents, antioxidants and / or colorants, their preparation and use in rubber blends and vehicle tires.

Abstract

The present invention provides a compound, a rubber blend containing the compound, a vehicle tire comprising the rubber blend as at least one component, a method for producing the compound, and the use of the compound as an anti-aging agent and / or antioxidant and / or colorant. [Solution] The following compound (I) is provided. TIFF2026136313000021.tif21170 In the formula, R 1 xii) Aromatic groups having substituents optionally 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-C3 groups. 12 The group is selected from a group consisting of groups, where X is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group), and Y is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group).

Description

[Technical Field]

[0001] The present invention relates to a compound, a rubber mixture containing the compound, a vehicle tire comprising the rubber mixture as at least one component, a method for producing the compound, and the use of the compound as an aging stabilizer and / or antioxidant and / or dye. [Background technology]

[0002] It is well known that polymer materials, particularly rubber, are used in vehicle tires and industrial rubber articles.

[0003] During long-term storage, and especially in applications where high temperatures are frequently encountered, natural rubber and synthetic polymers (IR, BR, SSBR, ESBR, etc.), as well as natural and synthetic oils, fats, and lubricants, are subjected to oxidation reactions that adversely affect their original desired properties. Depending on the type of polymer, the polymer chains may shorten until the material liquefies, or the material may harden thereafter.

[0004] Therefore, aging stabilizers contribute significantly to the service life of vehicle tires and other industrial rubber products.

[0005] Known anti-aging stabilizers include aromatic amines, for example, 6PPD(N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine), IPPD (N-isopropyl-N'-phenyl-p-phenylenediamine) or SPPD (N-(1-phenylethyl)-N'-phenyl-p-phenylenediamine) is included.

[0006] These molecules can react with oxygen or ozone, or with free radicals formed by alkyl, alkoxy, and alkylperoxy groups, and thus remove them, thereby protecting the polymer from further oxidation reactions. [Overview of the project] [Problems that the invention aims to solve]

[0007] However, a drawback of this class of substances is that they may be carcinogenic.

[0008] In particular, aging stabilizers that react with ozone and bring about its scavenging are also called "ozone deterioration inhibitors".

[0009] A further problem associated with aging stabilizers is undesirable blooming. Here, due to the somewhat poor solubility of the molecules of the aging stabilizer in the polymer matrix around the rubber article, they diffuse to the surface of the article to be protected, causing a film to form there that is usually distinguishable in color from the rest of the article. In the case of vehicle tires, this usually appears as a brownish coloring of the sidewalls that are otherwise black. In addition to the aesthetic drawback, this is also related to a drawback in terms of the aging stabilization effect. For this reason, the blooming substance is usually removed. This first reduces the total amount of the aging stabilizer and also affects the further diffusion of the molecules of the aging stabilizer to that location, as a result of which the protection level of the polymer is reduced.

Means for Solving the Problems

[0010] The object of the present invention is to provide novel compounds that can be used as aging stabilizers for vehicle tires or other industrial rubber articles, in particular, which in combination with sufficient solubility in their respective matrix, for example, in particular in polymers, have a lower potential risk. This is intended to continue to provide optimal protection from oxygen and ozone and minimize or prevent the tendency to bloom while reducing harm to health.

[0011] At the same time, the compound is intended to ensure equivalent or even improved aging stabilization compared to aromatic amines such as 6PPD.

[0012] This objective is achieved by the compound according to the present invention as described in claim 1, the rubber mixture according to the present invention containing the compound, and the vehicle tire according to the present invention containing the rubber mixture according to the present invention in at least one component.

[0013] Furthermore, this objective can also be achieved by the process according to the present invention for producing the compounds according to the present invention.

[0014] The compound described in claim 1 is of general formula I): [ka] It has, in the formula, R 1 xii) Aromatic groups having substituents optionally selected from the group consisting of halogen groups, cyano groups, ester groups, ketone groups, ether groups and thioether groups, and linear, branched and cyclic aliphatic C3-C3 groups. 12 Selected from a group consisting of elements, Here, the base R 2 and R 3 These may be independently identical or different from each other, and may optionally have one or more halogen substituents, and are linear, branched, and cyclic, saturated and unsaturated, aliphatic C1-C1. 12 A group selected from the group consisting of a group, an aryl group having one or more halogen substituents optionally, and a halogen group (wherein fluorine, bromine, and chlorine are preferred), a cyano group, an ester group, a ketone group, an ether group, and a thioether group, m can take the value 0, 1, 2, or 3. n can take the value 0, 1, 2, 3, or 4. X is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group), and Y is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group).

[0015] For example, if m is 0 (zero), 1, or 2, then each hydrogen atom is R 2 It will be obvious to those skilled in the art that instead, it is bonded to the corresponding carbon atom of the benzene ring. Of course, this is R 3And the same applies to n less than 4 as well.

[0016] Similarly, the expression of the (R 2 ) m , (R 3 ) n‘ and R 1 HN bonds means that, except for the fact that more than two of them cannot be simultaneously arranged at the same position as already excluded by the tetravalence of the carbon atoms of the benzene ring, these groups can be arranged at any position on their respective benzene rings. This is obvious to those skilled in the art.

[0017] In connection with the present invention, the description of "C3 - C 12 group" is understood to mean a group having 3 to 12 carbon atoms. Independently of this, "C1" is used to represent the position of the most highly oxidized carbon atom / the carbon atom with the highest priority according to the Cahn - Ingold - Prelog rules (CIP). What is meant for each will be obvious to those skilled in the art.

[0018] The compounds according to the present invention are dibenzodiazepinone derivatives and exhibit low potential hazards compared to known aniline - based anti - aging stabilizers (possible cleavage products of 6PPD).

[0019] This is an extremely important advantage, especially in industrial applications such as vehicle tires or other industrial rubber products, because the rubber components can be released by abrasion or other degradation processes. Furthermore, the basic structure dibenzodiazepinone is found in many orally administered pharmaceuticals.

[0020] Compared to the known anti - aging stabilizer 6PPD, the compounds according to the present invention show an improved antioxidant effect especially at relatively high temperatures exceeding 150°C. As a result, the compounds of formula (I) achieve an equivalent or even improved protective effect especially in vehicle tires and other industrial rubber articles, and also in oils and lubricants.

[0021] However, the present invention is not bound by any particular mechanism of action or description.

[0022] Therefore, the compounds according to the present invention are suitable as substitutes for 6PPD, whose degradation products are highly toxic to coho salmon, and therefore possibly to other aquatic organisms as well.

[0023] The compounds according to the present invention also have sufficient solubility in rubber mixtures, particularly vehicle tires and other industrial rubber articles. This minimizes blooming of the compounds, which often occurs with many aging stabilizers, and thus provides a favorable aging stabilization effect. Less blooming of an aging stabilizer means less aging stabilizer is removed intentionally or unintentionally from the surface of the article to be protected, and consequently less aging stabilizer diffuses onto the surface.

[0024] The compounds of formula I) according to the present invention are particularly suitable as aging stabilizers and / or ozone degradation inhibitors in vehicle tires and / or other industrial rubber articles, such as air springs, bellows, conveyor belts, straps, drive belts, hoses, rubber bands, profiles, seals, membranes, medical or robotic tactile sensors, or shoe soles or parts thereof, and / or oils and / or lubricants.

[0025] The compound of formula I) according to the present invention is particularly suitable for the manufacture of rubber articles, especially air springs, bellows, conveyor belts, straps, drive belts, hoses, rubber bands, profiles, seals, membranes, medical or robotic tactile sensors, or shoe soles or parts thereof.

[0026] For the use of the compound of formula I) in the cited article or substance, the compound is used in a composition and incorporated into the composition.

[0027] In vehicle tires or other industrial rubber articles, the composition is particularly a rubber mixture.

[0028] The present invention further provides the use of compounds of formula I) according to the present invention, particularly in oils and lubricants such as fuels or fluids for engines. In particular, compounds according to the present invention can be used in engines.

[0029] The present invention further provides the use of compounds according to Formula I) of the present invention as dyes in fibers and / or polymers and / or paper, and / or (decorative) paints and coatings. [Modes for carrying out the invention]

[0030] The present invention includes all advantageous embodiments reflected in the claims, among other things. The present invention also includes embodiments arising from different combinations of features having different priorities over these features, in particular including combinations of first features described as “preferred” or described in the context of an advantageous embodiment with further features described as, for example, “particularly preferred.”

[0031] Furthermore, all information relating to the characteristics of the compounds of the present invention also applies to the method of the present invention for producing the compounds, the rubber mixtures of the present invention containing the compounds, and the uses of the present invention.

[0032] -N(H)R 1 The base is preferably positioned in the meta position relative to X.

[0033] Therefore, the compound according to the present invention is preferably of formula II): [ka] It has a structure, In the formula, R 1 , R 2 , R 3 X and Y, as well as m and n, are defined above.

[0034] This particularly successfully achieves the objectives of the present invention, and especially achieves sufficient solubility of the compound in rubber mixtures, particularly in vehicle tires.

[0035] As is clear from formulas I) and II), X is incorporated into the ring structure and selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group).

[0036] It is obvious to those skilled in the art that when X is NH, the nitrogen atom (N) is bonded to the adjacent carbon atom, and the hydrogen atom (H) is bonded only to the nitrogen atom.

[0037] For example, it is preferable that X is NH in both formulas I) and II). This is particularly good at achieving the objectives of the present invention and achieving a very good antioxidant effect, especially in polymer and / or rubber mixtures, and especially in vehicle tires.

[0038] For example, as is clear from formulas I) and II), Y is terminally bonded to a carbon atom. It is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group).

[0039] It is obvious to those skilled in the art that when Y is NH, the nitrogen atom (N) is bonded to the adjacent carbon atom, and the hydrogen atom (H) is bonded only to the nitrogen atom.

[0040] For example, in formulas I) and II), it is preferable that Y is O, i.e., an oxygen atom, in each case, and therefore yields a carbonyl group (-C=O) next to X.

[0041] This achieves the objectives of the present invention particularly well, and achieves a very good antioxidant effect, especially in polymer and / or rubber mixtures, particularly in vehicle tires.

[0042] base R 2 and R 3 These are linear, branched, and cyclic, saturated and unsaturated, aliphatic C1-C atoms that are independently identical or distinct from one or more halogen substituents and optionally have one or more halogen substituents. 12The group is selected from the group consisting of a group, an aryl group having one or more halogen substituents optionally, and halogen groups (wherein fluorine, bromine, and chlorine are preferred), a cyano group, an ester group, a ketone group, an ether group, and a thioether group.

[0043] Enumerated bases R 2 and R 3 In particular, these may already be bonded to each benzene ring / its precursor by selecting a suitable starting material.

[0044] For example, in particular in formulas I) and II), it is preferable that m is zero (0).

[0045] For example, in particular equations I) and II), it is preferable that n is zero (0).

[0046] This results in formula Ia) or IIa): [ka] A preferred structure as shown can be obtained. In the formula, X, Y and R 1 It is defined as above.

[0047] Here again, it is preferable that X is N(H) and Y is O.

[0048] base R 1 teeth, xi) Aromatic groups having substituents optionally selected from the group consisting of halogen groups, cyano groups, ester groups, ketone groups, ether groups, and thioether groups, xii) Linear, branched and cyclic aliphatic C3-C 12 Selected from a group consisting of elements.

[0049] The aromatic group of subgroup xi) is preferably selected from, for example, a phenyl group (-C6H5) and a benzyl group (-CH2-C6H5), with phenyl being particularly preferred.

[0050] The aromatic group of subgroup xi) may have substituents.

[0051] As described above, these are selected from the group consisting of halogen groups, cyano groups, ester groups, ketone groups, ether groups, and thioether groups.

[0052] It is preferable that the substituent is selected from the group consisting of ester groups, ketone groups, ether groups, and thioether groups.

[0053] In a preferred embodiment, the aromatic group is not substituted on the two carbon atoms adjacent to the C1 atom, i.e., the carbon atom bonded to the N atom. Therefore, in the case of a benzene ring as the basic structure, it is preferable that there is no substituent at the ortho position relative to the N atom.

[0054] In a more preferred embodiment, the aromatic group of subgroup xi) is not substituted.

[0055] R 1 It is preferable that the C1 atom is bonded to the nitrogen atom (N) via a tertiary carbon atom. That is, the C1 atom is preferably a tertiary carbon atom.

[0056] In relation to the present invention, the term "tertiary carbon atom" is understood to mean a carbon atom bonded to only one hydrogen atom.

[0057] This provides a particularly good protective effect compared to secondary and quaternary carbon atoms, due to the presence of the compound in rubber mixtures, especially in vehicle tires and other industrial rubber articles, resulting in optimal reactivity, particularly in relation to mechanisms related to aging stabilization, and avoiding undesirable side reactions.

[0058] In a further advantageous embodiment, in particular in the above-mentioned formulas I), II), Ia), IIa), R 1 R is a branched or cyclic alkyl group having 3 to 12 carbon atoms, preferably 3 to 8 carbon atoms, where R 1The group is particularly preferably selected from a 1,3-dimethylbutyl group and a cyclohexyl group, where R 1 This is very preferably a 1,3-dimethylbutyl group.

[0059] This results in particularly good solubility in rubber mixtures for vehicle tires and other industrial rubber articles.

[0060] In a particularly preferred embodiment, the compound according to the present invention is given by formula III): [ka] It has the structure of [the object].

[0061] The compound of formula III) has sufficient solubility in polymers, particularly in rubber mixtures for vehicle tires and other industrial rubber articles. At the same time, the compound of formula II) can be produced in a particularly simple, energy-efficient, and cost-saving manner, and exhibits an antioxidant effect equivalent to or even better than 6PPD, particularly at temperatures above 150°C, and therefore an equivalent or improved anti-aging stabilization effect.

[0062] According to IUPAC nomenclature, the compound of formula III) may also be called 2-(1,3-dimethylbutylamino)-5,10-dihydro-dibenzo[b,e][1,4]diazepine-11-one.

[0063] As described above, the present invention further relates to a method for producing a compound of formula I), comprising at least the following process steps: i) A step of producing or providing the substance of formula B1): [ka] ii) A step of reacting the compound of formula B1) with hydrogen and a ketone or aldehyde, preferably a ketone, to obtain the compound of formula I): [ka] It includes at least, In the formula, R1 xi) an aromatic group having a substituent optionally selected from the group consisting of halogen groups, cyano groups, ester groups, ketone groups, ether groups and thioether groups, xii) Linear, branched and cyclic aliphatic C3-C 12 Selected from a group consisting of elements, base R 2 and R 3 These may be independently identical or different from each other, and may optionally have one or more halogen substituents, and are linear, branched, and cyclic, saturated and unsaturated, aliphatic C1-C1. 12 A group selected from the group consisting of a group, an aryl group having one or more halogen substituents optionally, and a halogen group (wherein fluorine, bromine, and chlorine are preferred), a cyano group, an ester group, a ketone group, an ether group, and a thioether group, m can take the value 0, 1, 2, or 3. n can take the value 0, 1, 2, 3, or 4. The present invention provides a method in which X is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group), and Y is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group).

[0064] All of the above information provided in connection with the description of the compounds according to the present invention, including preferred embodiments and taking into consideration the possibility of any preferred hierarchy of these features and combinations thereof, is R 1 , R 2 , R 3 This applies to X, Y, m, and n.

[0065] When X is N(H) (a secondary amino group) and Y is O (an oxygen atom), the compound of formula B1) can be prepared according to the following scheme S1), for example, as in U.S. Patent No. 6919328: [ka] In the formula, TEA represents triethylamine and DMSO represents dimethyl sulfoxide.

[0066] Group-N(H)R 1 Furthermore, the group -NO2 in the starting material is preferably positioned at the meta position relative to X, as described above.

[0067] Therefore, the compounds produced according to the present invention preferably have the structure of formula II): [ka] It has.

[0068] For this purpose, the starting material of formula B1) preferably has the structure of formula B1a): [ka] It has, In the formula, R 1 , R 2 , R 3 X and Y, as well as m and n, are as defined above, and include all combinations of embodiments and features. Here again, in a preferred embodiment, X is N(H) and Y is O.

[0069] In step ii), it is preferable to use a suitable catalyst, referred to as a "hydrogenation catalyst" in the context of the present invention, for the reaction with hydrogen.

[0070] The hydrogenation catalyst is preferably a precious metal catalyst, such as palladium (Pd) or platinum (Pt). The precious metal is preferably used on carbon (C), such as palladium on carbon (Pd / C).

[0071] Furthermore, other known catalysts, such as Raney nickel or copper chromite, can also be used.

[0072] In step ii), the reaction with hydrogen It is particularly preferable when this is carried out using a hydrogenation catalyst.

[0073] The reaction in step ii) is preferably carried out at a temperature of 50°C to 130°C, preferably 50°C to 100°C, particularly preferably 50°C to 80°C, and especially preferably 60°C.

[0074] The reaction mixture is then preferably subjected to hydrogen at a pressure of 30-70 bar, particularly preferably 35-45 bar, especially 40 bar, and then stirred for 1-20 hours, preferably 3-13 hours, particularly preferably 5-13 hours, especially 10 hours.

[0075] The reaction with hydrogen in step ii) is preferably carried out in a vessel suitable for relatively high pressure, such as an autoclave or another pressure reactor.

[0076] It is particularly preferable that the reaction in step i) is carried out using hydrogen at a temperature of 50°C to 130°C, preferably 50°C to 100°C, and especially preferably 50°C to 80°C, using a hydrogenation catalyst, and that the reaction mixture is supplied to hydrogen at a pressure of, for example, 30 to 70 bar, especially preferably 35 to 45 bar, and especially preferably 40 bar, and that the reaction is carried out in an autoclave or another pressure reactor.

[0077] The ketone in step ii) is subsequently converted to group R 1 It is a ketone derivative of; in the case of an aldehyde, it is therefore an aldehyde derivative.

[0078] For simplicity, base R 1 This is the part that remains on the nitrogen atom after the reaction with an aldehyde or ketone, hence the abbreviated formula R 1 =O is used for aldehydes or ketones.

[0079] The ketone used here is preferably methyl isobutyl ketone.

[0080] The solvent in step ii) may be either a ketone or aldehyde if it is in liquid form, or an inert solvent such as toluene or xylene if the ketone or aldehyde is in solid form. In the latter case, the ketone or aldehyde is used only as a reactant in stoichiometric amounts.

[0081] As a solvent, a liquid form of ketone or aldehyde R 1 =O, and especially preferably a ketone, is preferred. This makes it possible to omit any additional substances such as toluene or xylene.

[0082] It is preferable that the process following step ii) is followed by purification, for example by filtration and scrubbing with a solvent, particularly ethanol, and / or by column chromatography with silica gel, or by recrystallization from cyclohexane or long-chain aliphatic compounds.

[0083] As described above, the present invention further provides rubber mixtures.

[0084] The rubber mixture according to the present invention contains, for example, a compound of formula I), preferably a compound of formula III). In principle, the rubber mixture according to the present invention may be any rubber mixture in which the novel compound of formula I) or III) according to the present invention is low in toxicity and acts as an aging stabilizer and / or an ozone degradation inhibitor.

[0085] The rubber mixture according to the present invention contains at least one rubber.

[0086] The rubber mixture according to the present invention preferably contains a compound of formula I), for example, preferably a compound of formula III), in an amount of 0.1 to 10 phr, particularly preferably 0.1 to 7 phr, very preferably 1 to 6 phr, and second preferably 1 to 3 phr.

[0087] The rubber mixture may also contain a mixture of two or more compounds conforming to formula I).

[0088] The unit "phr" (parts per 100 parts by weight of rubber) used in this document is a conventional expression of quantity in the rubber industry for mixture formulations. The dosage of individual substances in parts by weight, as specified herein, refers to all high molecular weight (M) substances present in the mixture. w The standard is based on a total mass of 100 parts by weight of rubber (exceeding 20,000 g / mol).

[0089] In an advantageous embodiment of the present invention, the rubber mixture of the present invention contains at least one diene rubber.

[0090] Therefore, the rubber mixture may contain diene rubber or a mixture of two or more different diene rubbers.

[0091] Diene rubber is formed by polymerization or copolymerization of dienes and / or cycloalkenes, and is therefore a rubber having a C=C double bond in either the main chain or the side groups.

[0092] Diene rubber is preferably 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, molecular weight M w The selected material is from the group consisting of liquid rubber with a concentration exceeding 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 copolymer, hydrogenated acrylonitrile butadiene rubber, and hydrogenated styrene-butadiene rubber.

[0093] Nitrile rubber, hydrogenated acrylonitrile-butadiene rubber, chloroprene rubber, butyl rubber, halobutyl rubber, and / or ethylene-propylene-diene rubber are used, in particular, in the manufacture of industrial rubber articles such as straps, drive belts, and hoses, and / or shoe soles. It is preferable to use mixed compositions known to those skilled in the art for these rubbers, which are specific in terms of fillers, plasticizers, vulcanization systems, and additives.

[0094] The natural and / or synthetic polyisoprene in all embodiments may be cis-1,4-polyisoprene or 3,4-polyisoprene. However, it is preferable to use cis-1,4-polyisoprene having a cis-1,4 ratio of more than 90% by weight. Firstly, such polyisoprene can be obtained by stereospecific polymerization in solution with a Ziegler-Natta catalyst or by fine lithium alkyl. Secondly, natural rubber (NR) is such cis-1,4-polyisoprene having a cis-1,4 content of more than 99% by weight in natural rubber.

[0095] A mixture of one or more natural polyisoprenes and one or more synthetic polyisoprenes is also to be considered.

[0096] In the context of this invention, the term “natural rubber” should be understood to mean natural rubber that can be obtained from Hevea rubber trees and from “non-Hevea” sources. Examples of non-Hevea sources include guayule shrubs and dandelions such as TKS (Taraxacum kok-saghyz).

[0097] If the rubber mixture of the present invention contains butadiene rubber (i.e., BR, polybutadiene), this may be any type known to those skilled in the art. These include what are called high-cis and low-cis types, where polybutadiene with a cis content of 90% by weight or more is referred to as the high-cis type, and polybutadiene with a cis content of less than 90% by weight is referred to as the low-cis type. An example of low-cis polybutadiene is Li-BR (lithium-catalyzed butadiene rubber) with a cis content of 20% to 50% by weight. In high-cis BR, particularly good properties and low hysteresis are achieved in the rubber mixture.

[0098] The polybutadiene(s) used may be end-group modified and / or functionalized by modification and / or functionalization along the polymer chain. Modification can be selected from modification with hydroxyl groups and / or ethoxy groups and / or epoxy groups and / or siloxane groups and / or amino groups and / or aminosiloxanes and / or carboxyl groups and / or phthalocyanine groups and / or silane sulfide groups. However, further modifications known to those skilled in the art, also called functionalization, are also useful. Metal atoms may be components of such functionalization.

[0099] When at least one styrene-butadiene rubber (styrene-butadiene copolymer) is present in the rubber mixture, this may be solution-polymerized styrene-butadiene rubber (SSBR) or emulsion-polymerized styrene-butadiene rubber (ESBR), and 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 relation to the present invention.

[0100] The styrene-butadiene copolymer used may be end-group modified and / or functionalized along the polymer chain by the modification and functionalization of polybutadiene as described above.

[0101] Preferably, 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 (IIR), and halobutyl rubber.

[0102] In a particularly preferred embodiment of the present invention, 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).

[0103] In a particularly advantageous embodiment of the present invention, the rubber mixture contains at least one natural polyisoprene (NR) preferably in an amount of 50 to 100 phr, and in one particularly advantageous embodiment of the present invention, in an amount of 80 to 100 phr, more preferably 95 to 100 phr, and second preferably 100 phr. Such rubber mixtures exhibit optimized tear and abrasion properties, coupled with particularly good processability and recovery stability.

[0104] If the rubber mixture contains less than 100 phr of NR, it preferably contains 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).

[0105] In a particularly advantageous embodiment of the present invention, the rubber mixture contains at least one natural polyisoprene (NR) in an amount preferably 5 to 55 phr, and in one particularly advantageous embodiment of the present invention, in an amount of 5 to 25 phr, more preferably 5 to 20 phr. Such rubber mixtures exhibit particularly good processability and recovery stability, as well as optimized tear properties and optimal rolling resistance properties.

[0106] In a particularly advantageous embodiment of the present invention, the rubber mixture contains at least one polybutadiene (BR, butadiene rubber) in an amount of preferably 10 to 80 phr, more preferably 10 to 50 phr, and in a particularly advantageous embodiment of the present invention, in an amount of 15 to 40 phr. This achieves particularly good tear and abrasion properties, as well as optimal braking properties, of the rubber mixture of the present invention.

[0107] In a further particular advantageous embodiment of the present invention, the rubber mixture comprises at least one solution-polymerized styrene-butadiene rubber (SSBR) in an amount preferably 10 to 80 phr, more preferably 30 to 80 phr, and in a particular advantageous embodiment of the present invention, in an amount of 50 to 70 phr. This achieves the particularly good rolling resistance characteristics of the rubber mixture of the present invention. In a particularly advantageous embodiment of the present invention, the SSBR is used in combination with at least one further rubber to achieve an optimal and balanced characteristic profile.

[0108] It is preferable that the rubber mixture contains at least one filler in an amount of preferably 30 to 500 phr, more preferably 50 to 400 phr, and then preferably 80 to 300 phr.

[0109] In an advantageous embodiment of the present invention, the filler is preferably a reinforcing filler selected from the group consisting of carbon black and silicon dioxide.

[0110] Suitable carbon black includes all types of carbon black known to those skilled in the art. Preferably, the carbon black is selected from industrial carbon black and pyrolysis carbon black, with industrial carbon black being more preferred.

[0111] The carbon black preferably has an iodine value in accordance with ASTM D1510, also known as an iodine adsorption capacity of 30-250 g / kg, preferably 30-180 g / kg, more preferably 40-180 g / kg, and even more preferably 40-130 g / kg, and a DBP value in accordance with ASTM D2414 of 30-200 ml / 100 g, preferably 70-200 ml / 100 g, and more preferably 90-200 ml / 100 g.

[0112] The DBP value, in accordance with ASTM D2414, determines the specific absorption volume related to dibutyl phthalate in carbon black or light-colored fillers.

[0113] The use of this type of carbon black in rubber mixtures, particularly for vehicle tires, ensures an optimal compromise between wear resistance and heat retention, which in turn affects ecologically relevant rolling resistance.

[0114] Particularly suitable and preferred carbon blacks are those having an iodine adsorption number of 80-110 g / kg and a DBP number of 100-130 ml / 100 g, such as N339 type carbon black.

[0115] The silicon dioxide is preferably amorphous silicon dioxide, such as precipitated silica, also known as precipitated silicon dioxide. However, alternatively, for example, fine particle silicon dioxide can also be used.

[0116] However, it is particularly preferable to use finely ground precipitated silica having a nitrogen surface area (BET surface area) of 35-400 m² / g, preferably 35-350 m² / g, more preferably 85-320 m² / g, and even more preferably 120-235 m² / g (according to DIN ISO 9277 and DIN 66132) and a CTAB surface area of ​​30-400 m² / g, preferably 30-330 m² / g, more preferably 80-300 m² / g, and even more preferably 115-200 m² / g (according to ASTM D 3765). Such silica provides particularly good physical properties of vulcanized rubber, for example, in rubber mixtures for tire treads. The advantages in processing the mixture due to reduced mixing time can also be provided while maintaining the same product properties, resulting in improved productivity. The silica used may therefore be, for example, Ultrasil® VN3 type (trade name) from Evonik, or highly dispersed silica known as HD silica (for example, Zeosil® 1165 MP from Solvay).

[0117] In a particularly advantageous embodiment of the present invention, the rubber mixture contains at least one silica as a filler, preferably in an amount of 30 to 500 phr, more preferably 50 to 400 phr, and then preferably 80 to 300 phr.

[0118] In these quantities, silica is present either alone or as the main filler (more than 50% by weight based on the total amount of filler).

[0119] In a further advantageous embodiment of the present invention, the rubber mixture contains at least one silica as a further filler, preferably in an amount of 5 to 100 phr, more preferably 5 to 80 phr, and then preferably 10 to 60 phr.

[0120] In these quantities, silica is present as an additional filler, particularly in addition to other main fillers such as carbon black.

[0121] The terms "silicic acid" and "silica" are used synonymously in relation to the present invention.

[0122] In a particularly advantageous embodiment of the present invention, the rubber mixture according to the present invention contains at least one carbon black in an amount of 0.1 to 60 phr, preferably 3 to 40 phr, particularly preferably 5 to 30 phr, and most particularly preferably 5 to 15 phr. In these amounts, the carbon black is present as an additional filler, particularly in addition to a main filler such as silica.

[0123] In a further advantageous embodiment of the present invention, the rubber mixture of the present invention contains at least one carbon black in an amount of 30 to 300 phr, preferably 30 to 200 phr, and more preferably 40 to 100 phr. In these amounts, the carbon black is present alone or as a main filler, and optionally in combination with silica in the lower end of the above amounts.

[0124] In certain advantageous embodiments of the present invention, the rubber mixture contains at least one carbon black in an amount of 5 to 60 phr, more preferably 5 to 40 phr, and at least one silica in an amount of 50 to 300 phr, preferably 80 to 200 phr.

[0125] The rubber mixture may further contain additional reinforcing or non-reinforcing fillers.

[0126] Further (non-reinforcement) fillers in connection with the present invention include aluminosilicates, kaolin, chalk, starch, magnesium oxide, titanium dioxide, or rubber gels and fibers (e.g., aramid fibers, glass fibers, carbon fibers, cellulose fibers).

[0127] Furthermore, optionally reinforcing fillers include, for example, carbon nanotubes (CNTs) such as discrete CNTs, hollow carbon fibers (HCFs), and modified CNTs containing one or more functional groups, such as hydroxy, carboxy, and carbonyl groups, graphite and graphene, as well as what is known as "carbon-silica two-phase fillers."

[0128] In relation to the present invention, zinc oxide is not included in the filler.

[0129] The rubber mixture may further contain conventional additives in conventional parts by weight, which are preferably added during at least one primary mixing stage in the production of the mixture. These additives include: a) Anti-aging stabilizers known in conventional technology, For example, p-phenylenediamine, for example, N-phenyl-N'-(1,3-dimethylbutyl)-p-phenylenediamine (6PPD), N,N'-diphenyl-p-phenylenediamine (DPPD), N-(1-phenylethyl)-N'-phenyl-p-phenylenediamine (SPPD), N,N'-ditolyl-p-phenylenediamine (DTPD), N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7 PPD), N-isopropyl-N'-phenyl-p-phenylenediamine (IPPD), Or dihydroquinoline, for example, 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) Fillers, particularly activators and / or agents for binding carbon black or silica, such as S-(3-aminopropyl)thiosulfate and / or its metal salt (for binding carbon black) and silane coupling agents (for binding silica), d) Ozone degradation inhibitor wax, e) Resins, especially tackifying resins, f) For example, a mixing aid such as 2,2'-dibenzamide diphenyl disulfide (DBD), and g) Processing aids, especially fatty acid esters and metal soaps, such as zinc soap and / or calcium soap, h) Plasticizers, such as particularly aromatic, naphthenic, or paraffinic mineral oil plasticizers, such as MES (Mild Extract Solvates), RAE (Residual Aromatic Extracts), or TDAE (Treatment Distillate Aromatic Extracts) preferably having a polycyclic aromatic compound content of less than 3% by weight according to Method IP 346, or rubber liquefaction (RTL) oil or biomass liquefaction (BTL) oil, or triglycerides, such as rapeseed oil or Factis, or hydrocarbon resins, or liquid polymers having an average molecular weight (measured by GPC = gel permeation chromatography in accordance with BS ISO 11344:2004) of 500 to 20000 g / mol.

[0130] When mineral oil is used, it is preferably selected from the group consisting of DAE (distillate aromatic extract), RAE (residual aromatic extract), TDAE (treated distillate aromatic extract), MES (mildly extracted solvate), and naphthenic oils.

[0131] In particularly advantageous embodiments, the rubber mixture according to the present invention does not contain, in addition to the compounds of the present invention of formula I), for example formula III), aging stabilizers from the group of p-phenylenediamines, particularly those listed above in a). In particularly preferred embodiments, the rubber mixture according to the present invention contains a further aging stabilizer of 0 to 0.1 phr, particularly 0 phr, based on p-phenylenediamine, which is selected from the group including, preferably from the group 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'-ditril-p-phenylenediamine (DTPD), N-isopropyl-N'-phenyl-p-phenylenediamine (IPPD), and N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD).

[0132] The p-phenylenediamines present in accordance with the present invention, preferably in very small amounts of 0 to 0.1 phr, particularly preferably 0 phr, and the compounds of formula I), e.g., formula III), enable the achievement of equivalent protective effects with lower toxicity. The compounds of the present invention of formula I), e.g., formula III), replace the listed p-phenylenediamines known in the prior art.

[0133] In a further advantageous embodiment of the present invention, since there is at least one further representative of the p-phenylenediamine aging stabilizers mentioned, the compounds of the present invention partially replace p-phenylenediamine known in the prior art. This also achieves the advantages of the present invention, but only to a lesser extent.

[0134] In advantageous embodiments, a dihydroquinoline-based aging stabilizer, such as TMQ, is present in the rubber mixture in addition to the compound of formula I) of the present invention. The amount of dihydroquinoline present, particularly TMQ, is preferably 0.1 to 3, and especially 0.5 to 1.5 phr.

[0135] The ozone degradation inhibitor waxes (group d above) are considered separately and, in preferred embodiments of the present invention, are present in the rubber mixture with or without the presence of additional aging stabilizers a).

[0136] The silane coupling agent is any type known to those skilled in the art.

[0137] Furthermore, one or more different silane coupling agents can be used in combination with each other. Therefore, the rubber mixture may contain a mixture of different silanes.

[0138] Silane coupling agents react with silicon dioxide, particularly silica, surface silanol groups, or other polar groups, even before the addition of fillers to the rubber, during the mixing of the rubber / rubber mixture (in situ) or during pretreatment (pre-modification).

[0139] The coupling agents known from the prior art are bifunctional organosilanes having at least one alkoxy, cycloalkoxy, or phenoxy group as a leaving group on a silicon atom, and possibly other functional groups that can proceed to chemical reactions with the polymer's double bond after cleavage. The groups in the latter may include, for example, the following chemical groups: -SCN, -SH, -NH2, or -S x -(Here, x = 2 to 8).

[0140] Available silane coupling agents therefore include, for example, 3-mercaptopropyltriethoxysilane, 3-thiocyanatopropyltrimethoxysilane, or 3,3'-bis(triethoxysilylpropyl) polysulfides having 2 to 8 sulfur atoms, such as 3,3'-bis(triethoxysilylpropyl) tetrasulfide (TESPT), the corresponding disulfide (TESPD), or other mixtures of sulfides having 1 to 8 sulfur atoms and various sulfides of different composition. TESPT can also be added as a mixture with industrial carbon black, for example (trade name X50S®, manufactured by Evonik).

[0141] For example, blocked mercaptosilanes, such as those publicly known from International Publication No. 99 / 09036, can also be used as silane coupling agents. Silanes described in International Publication Nos. 2008 / 083241, 2008 / 083242, 2008 / 083243, and 2008 / 083244 can also be used. Usable silanes include, for example, 3-octanoylthio-1-propyltriethoxysilane, which is sold in numerous varieties under the name NXT by Momentive in the United States, or VPSi363 (registered trademark) sold by Evonik Industries.

[0142] The total proportion of further additives is preferably 3 to 150 phr, more preferably 3 to 100 phr, and most preferably 5 to 80 phr.

[0143] Zinc oxide (ZnO) may be included in the overall proportion of further additives in the amounts mentioned above.

[0144] This may be any type of zinc oxide known to those skilled in the art, such as ZnO granules or powder. Commonly used zinc oxide generally has a BET surface area of ​​less than 10 m² / g. However, it is also possible to use zinc oxide with a BET surface area of ​​10 to 100 m² / g, such as "nano zinc oxide."

[0145] The rubber mixture of the present invention is preferably used in a vulcanized form, particularly in vehicle tires or other rubber articles using vulcanization technology.

[0146] The terms "vulcanization" and "crosslinking" are used synonymously in the context of this invention.

[0147] The vulcanization of the rubber mixture of the present invention is preferably carried out in the presence of sulfur and / or a sulfur donor with the assistance of a vulcanization accelerator, and some vulcanization accelerators can act as sulfur donors simultaneously. The vulcanization accelerator is selected from the group consisting of thiazole vulcanization accelerators, mercapto vulcanization accelerators, sulfenamide vulcanization accelerators, thiocarbamate vulcanization accelerators, thiram vulcanization accelerators, thiophosphate vulcanization accelerators, thiourea vulcanization accelerators, xanthogenet vulcanization accelerators, and guanidine vulcanization accelerators.

[0148] It is preferable to use a sulfenamide accelerator selected from guanidine accelerators such as N-cyclohexyl-2-benzothiazolyl sulfenamide (CBS), N,N-dicyclohexylbenzothiazole-2-sulfenamide (DCBS), benzothiadyl-2-sulfenmorpholide (MBS), N-tert-butyl-2-benzothiadylsulfenamide (TBBS), and diphenylguanidine (DPG).

[0149] The sulfur donor substance used may be selected from any sulfur donor substances known to those skilled in the art.

[0150] A vulcanization retarder may be present in the rubber mixture.

[0151] The production of rubber mixtures is preferably carried out by a process conventional in the rubber industry, in which a primary mixture containing all components except the vulcanizing system (e.g., sulfur and vulcanizing-inducing substances) is first produced in one or more mixing steps. The final mixture is produced by adding the vulcanizing system in the final mixing step.

[0152] The final mixture is further processed, for example, and given a suitable shape by extrusion molding or calendering.

[0153] The rubber mixture of the present invention is particularly suitable for use in vehicle tires, especially pneumatic vehicle tires. In principle, it can be used in all tire components, especially outer components, particularly preferably flange profiles, treads and / or sidewall treads. In the case of treads with a cap / base structure, the rubber mixture of the present invention is preferably used at least within the cap.

[0154] For use in vehicle tires, the mixture, as a finished mixture before vulcanization, is preferably formed into the corresponding shapes of the outer components and applied in known ways during the manufacture of green vehicle tires.

[0155] The production of the rubber mixture of the present invention for use as any other body mixture in vehicle tires is carried out as described above. Differences exist in the extrusion molding operation / formation after calendering of the mixture. The shapes of the unvulcanized rubber mixtures thus obtained for one or more different body mixtures are then used in the production of green tires.

[0156] Here, "main mixture" basically refers to the rubber mixture for the inner components of the tire, such as the squeegee, inner liner (inner layer), core profile, belt, shoulder, belt profile, carcass, bead reinforcement, bead profile, flange profile, and bandage.

[0157] The green tires, which have not yet been vulcanized, will then be vulcanized.

[0158] For the use of the rubber mixture of the present invention in drive belts and other belts, particularly conveyor belts, the extruded, unvulcanized mixture is given a suitable shape, and often, simultaneously or subsequently, reinforcing members, such as synthetic fibers or steel cords, are provided. This typically results in a multiply structure consisting of one and / or more plies of the rubber mixture, one and / or more plies of equivalent and / or different reinforcing members, and one and / or more further plies of the same and / or other rubber mixtures.

[0159] The present invention further provides a vehicle tire comprising a rubber mixture according to the present invention, which contains a compound according to the present invention in at least one component.

[0160] A vulcanized vehicle tire comprising at least one component comprises a vulcanized product of at least one rubber mixture of the present invention. It is known to those skilled in the art that most substances present, such as rubber, may already be present after mixing or may only be present in a chemically modified form after vulcanization.

[0161] In relation to the present invention, "vehicle tires" means industrial tires, as well as pneumatic vehicle tires and solid rubber tires, including tires for construction site vehicles, trucks, cars, and motorcycles.

[0162] The vehicle tire of the present invention comprises the rubber mixture of the present invention in at least one external component, wherein the external component is preferably a tread, sidewall, and / or flange profile.

[0163] Therefore, the vehicle tire of the present invention may also optionally contain, in two or more components, a rubber mixture according to the present invention containing the compound of formula I), together with a suitable composition. [Examples]

[0164] Here, the present invention will be described more specifically with respect to exemplary embodiments.

[0165] Compound III) as an exemplary embodiment of compound I) is prepared in the manner shown in schemes S1a) and S2) below: [ka] The synthesis was carried out in accordance with S1a) of U.S. Patent No. 6919328.

[0166] Synthesis of 2-(1,3-dimethylbutylamino)-5,10-dihydro-dibenzo[b,e][1,4]diazepine-11-one (compound of formula III): [ka] 0.30 g (1.12 mmol, 1 equivalent) of 2-nitro-5,10-dihydro-dibenzo[b,e][1,4]diazepine-11-one, 0.10 g of activated carbon-supported platinum (Pt / C) (5%) (on a substrate of 0.4 g, 4.67 mmol), and 20.0 ml of methyl isobutyl ketone (MIBK) were weighed into a stainless steel autoclave fitted with a Teflon liner. The reaction mixture was then subjected to 40 bar of hydrogen (H2), and the mixture was stirred at 60°C for 10 hours. After the reaction was complete, excess hydrogen was released, the suspension was filtered through Celite®, and washed with ethanol. The filtrate was concentrated until dry and dried under reduced pressure. The product was purified by column chromatography (cyclohexane / acetic acid). Brown solid; yield 0.18 g (50% of theoretical value). 1H-NMR (Nuclear Magnetic Resonance) (500MHz, DMSO-d6) δ=9.72(s,1H),7.20(s,1H),6.97-6.82(m,5H ),6.77(d,J=8.5Hz,1H),6.63(dd,J=8.6,2.9Hz,1H),5.00(d,J=8.3Hz,1H),3. 31(s,1H),1.71(dh,J=13.4,6.5Hz,1H),1.44-1.32(m,5H),1.18(dt,J=13.8,6 .9Hz,1H),1.03(d,J=6.2Hz,3H),0.89(d,J=6.6Hz,3H),0.85(d,J=6.6Hz,3H). ESI-MS (Electrospray Ionization Mass Spectrometry) [M+H] + =310.

[0167] Measurement of Oxidation Induction Time (OIT) The compound of formula III) was studied under laboratory conditions for its potential protective effect as an anti-aging stabilizer by measuring the oxidation induction time.

[0168] For this purpose, the compounds of formula III) and 6PPD are used in both cases as polymers (liquid synthetic polyisoprene (IR), LIR-50, Kuraray, weight-average molecular weight distribution M w = 54,000 g / mol, glass transition temperature T g Along with -63°C, the samples were heated at three different temperatures (180°C; 165°C; 150°C) until oxidation began.

[0169] Heating to 180°C was performed as follows: The process starts at a temperature of 35°C, heating at a rate of 20 K / min (Kelvin / min) to 170°C, then heating at a rate of 1 K / min to 180°C; purge gas: nitrogen (N2), volume flow rate 50 ml / min).

[0170] The test specimen was held under an N2 atmosphere at an isothermal temperature of 180°C for 5 minutes, and then the atmosphere was switched to an O2 atmosphere (volume flow rate 50 ml / min).

[0171] Heating to 165°C was similarly performed by first heating to 155°C at a heating rate of 20 K / min (Kelvin / min), and then heating to 165°C at a heating rate of 1 K / min.

[0172] Heating to 150°C was similarly performed by first heating to 140°C at a heating rate of 20 K / min (Kelvin / min), and then heating to 150°C at a heating rate of 1 K / min.

[0173] Oxidation was determined across a single peak using DSC (Differential Scanning Calorimetry).

[0174] The time (in minutes) until oxidation was measured for each sample.

[0175] Table 1 summarizes the results of a comparison with the known anti-aging stabilizer 6PPD.

[0176] [Table 1]

[0177] Considering a measurement accuracy of ±10 minutes, it is clear that the compound of formula III) achieves a significantly longer time to the onset of oxidation, thus providing improved protection than 6PPD at temperatures above 150°C.

[0178] At 150°C, the time until oxidation began was too long, so the experiment was terminated after 900 minutes in all cases. Therefore, the difference between 6PPD and the compound of formula III) has not been experimentally determined to date.

[0179] Therefore, the compound of the present invention represented by formula III) as a representative of the compound of the present invention represented by formula I) is more environmentally friendly, less harmful to health, and is an equivalent or even superior anti-aging stabilizer than further representatives of the substance class such as 6PPD / as described above.

[0180] At the same time, the compound of the present invention represented by formula III), as representative of the compound of the present invention represented by formula I), exhibits sufficient solubility in rubber mixtures. This minimizes blooming and, consequently, has a favorable effect on the protective effect.

[0181] Therefore, the compound of formula I) as a whole makes it possible to achieve improved protective effects for the listed possible applications.

[0182] For use in rubber mixtures for vehicle tires, the compounds of the present invention, such as Formula I, and for example Formula III, are added in a manner known to those skilled in the art during one of the mixing stages in the production of the rubber mixture, instead of conventional aging stabilizers known in the prior art, such as 6PPD, 7PPD, or IPPD.

[0183] For this purpose, the compound of formula III) is incorporated in various amounts, as shown in Table 2, for example. The resulting examples of the present invention are identified as E1 and E2.

[0184] For comparison, a rubber mixture containing 6PPD instead of the compound in formula III) is used as an aging stabilizer with the same composition in all other respects, and in both cases, substitutions are made on a molar basis between V1 and E1 and between V2 and E2. The amounts in Table 2 are reported in phr units. A reference (Ref.) without an aging stabilizer is also reported.

[0185] In all mixtures, the total amount of aging stabilizer (6PPD or formula III) and plasticizer oil MES is 10 phr.

[0186] [Table 2]

[0187] The embodiments of the present invention exhibit aging stabilization effects equivalent to or even better than those of rubber mixtures containing 6PPD.

Claims

1. Equation I): 【Chemistry 1】 A compound of which, in the formula, R １ xi) an aromatic group having a substituent optionally selected from the group consisting of halogen groups, cyano groups, ester groups, ketone groups, ether groups and thioether groups, Furthermore, xi) linear, branched and cyclic aliphatic C ３ ~C １２ Selected from a group consisting of elements, group R ２ and R ３ These may be independently identical or different from each other, and may optionally have one or more halogen substituents, and are linear, branched, and cyclic, saturated and unsaturated, aliphatic C １ ~C １２ A group selected from the group consisting of a halogen group, an aryl group having one or more halogen substituents optionally, and preferably a halogen group consisting of fluorine, bromine, and chlorine, a cyano group, an ester group, a ketone group, an ether group, and a thioether group. m can take the value of 0, 1, 2, or 3. n can take the value 0, 1, 2, 3, or 4. A compound in which X is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group), and Y is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group).

2. Formula II): 【Chemistry 2】 having the structure, wherein R １ , R ２ , R ３ , X and Y and m and n are as defined in claim 1, a compound according to claim 1.

3. The compound according to claim 1 or 2, characterized in that X is NH.

4. A compound according to any one of claims 1 to 3, characterized in that Y is O.

5. The compound according to any one of claims 1 to 4, characterized in that m is zero (0) and / or n is zero (0).

6. R １ The compound according to any one of claims 1 to 5, characterized in that it is bonded to a nitrogen atom (N) via a tertiary carbon atom.

7. R １ The compound according to any one of claims 1 to 6, characterized in that is a branched or cyclic alkyl group having 3 to 12 carbon atoms, preferably 3 to 8 carbon atoms.

8. R １ However, R is selected from the 1,3-dimethylbutyl group and the cyclohexyl group. １ The compound according to any one of claims 1 to 7, characterized in that the group is preferably a 1,3-dimethylbutyl group.

9. Formula III): 【Transformation 3】 A compound according to any one of claims 1 to 8, characterized by having the structure described above.

10. A rubber mixture containing the compound described in any one of claims 1 to 9, Preferably, a rubber mixture comprising at least one diene rubber 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 (IIR), and halobutyl rubber.

11. A vehicle tire comprising the rubber mixture according to claim 10 in at least one component, preferably at least one outer component, wherein the outer component is preferably a tread, sidewall and / or flange profile.

12. Use of the compound according to any one of claims 1 to 9 as an aging stabilizer and / or ozone degradation inhibitor, particularly in vehicle tires and / or other industrial rubber articles, for example, particularly air springs, bellows, conveyor belts, straps, drive belts, hoses, rubber bands, profiles, seals, membranes, tactile sensors for medical or robotic applications, or soles or parts thereof, and / or oils and / or lubricants.

13. Use of the compound according to any one of claims 1 to 9 for manufacturing rubber articles, in particular air springs, bellows, conveyor belts, straps, drive belts, hoses, rubber bands, profiles, seals, membranes, tactile sensors for medical or robotic applications, or soles 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 (decorative) paints and coatings.

15. A process for producing the compound of formula I), comprising the following process steps: i) A step of producing or providing the substance of formula B1): 【Chemistry 4】 ii) A step of reacting the compound of formula B1) with hydrogen and a ketone or aldehyde, preferably a ketone, to obtain the compound of formula I): 【Transformation 5】 It includes at least, In the formula, R １ xi) an aromatic group having a substituent optionally selected from the group consisting of halogen groups, cyano groups, ester groups, ketone groups, ether groups and thioether groups, Furthermore, xi) linear, branched and cyclic aliphatic C ３ ~C １２ Selected from a group consisting of elements, group R ２ and R ３ These may be independently identical or different from each other, and may optionally have one or more halogen substituents, and are linear, branched, and cyclic, saturated and unsaturated, aliphatic C １ ~C １２ A group selected from the group consisting of a halogen group, an aryl group having one or more halogen substituents optionally, and preferably a halogen group consisting of fluorine, bromine, and chlorine, a cyano group, an ester group, a ketone group, an ether group, and a thioether group. m can take the value of 0, 1, 2, or 3. n can take the value 0, 1, 2, 3, or 4. A process in which X is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group), and Y is selected from O (oxygen atom), S (sulfur atom), and N(H) (secondary amino group).

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

17. The compound of formula I) above, formula II): 【Transformation 6】 It has a structure, The substance in formula B1) is, formula B1a): 【Transformation 7】 It has a structure, In the formula, R １ , R ２ , R ３ The process according to claim 15 or 16, characterized in that X and Y and m and n are as defined in claim 15.

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