Patent Description:
At present, rubber articles, especially tire articles, usually use p-phenylenediamine compounds as anti-degradants. Among them, widely used are derivatives such as dialkyl-p-phenylenediamines, alkylaryl-p-phenylenediamines and diaryl-p-phenylenediamines, including N-(<NUM>,<NUM>-dimethylbutyl)-N'-phenyl-p-phenylenediamine (referred to as 6PPD or <NUM>), N-isopropyl-N'-phenyl-p-phenylenediamine (referred to as IPPD), N,N'-bis-(<NUM>,<NUM>-dimethylamyl)-p-phenylenediamine (referred to as 77PD), diphenyl p-phenylenediamine mixture (referred to as anti-degradant <NUM> or DTPD) and so on.

Although the existing anti-degradant products have a relatively significant effect on anti-aging aspects of tires and other fields, the anti-degradants in rubber articles or tires will quickly migrate to the surface of rubber articles or tires due to their own discoloration during use, which leads to pollution, discoloration and damage on the surface of rubber articles or tires; at the same time, because the anti-degradants migrate to the surface of rubber products such as tires too fast, resulting in a rapid reduction in the content of anti-degradants in the product, its durable protection performance will be relatively poor.

In recent years, with the improvement of green and sustainable economic development requirements, users are paying more and more attention to issues such as aging resistance and surface discoloration of tires. Therefore, there is a more urgent need to develop an anti-degradant product with longer-lasting anti-aging property than existing anti-degradants and discoloration resistance JPS6381145 discloses triazine derivatives used as antiageing agents in rubbers.

Based on the above problems existing in the prior art, the present invention provides a series of compounds with anti-aging and discoloration resistance functions and a preparation method thereof. The compound of the present invention has longer-lasting aging resistance and has discoloration resistance, can be used as an anti-degradant in rubber articles, especially rubber tires, and can prevent the aging and deterioration of rubber articles or rubber tires due to light, heat, oxygen, fatigue and so on during use.

Specifically, the present invention provides a compound represented by the following formula (I):
<CHM>
Wherein:.

In one or more embodiments of the present invention, R is C3~C10 alkyl or C3~C10 cycloalkyl, preferably C3~C10 branched chain alkyl or C3~C10 cycloalkyl, more preferably isopropyl, tert-butyl group, tert-octyl or cyclohexyl.

In one or more embodiments of the present invention, R<NUM> and R<NUM> are identical or different, each independently being C3~C10 alkyl or phenyl, preferably each independently being C3~C10 branched chain alkyl or phenyl, more preferably each independently being isopropyl, <NUM>,<NUM>-dimethylpentyl or phenyl.

In one or more embodiments of the present invention, the compound is selected from:
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
and
<CHM>.

The present invention also provides a method for preparing the compound of any embodiment of the present invention, comprising:.

In one or more embodiments of the present invention, in the reaction of step (<NUM>), alkaline solid powder is added, and the reaction temperature is <NUM> to <NUM>.

In one or more embodiments of the present invention, in the reaction of step (<NUM>), alkaline liquid is added, and the reaction temperature is <NUM> to <NUM>.

In one or more embodiments of the present invention, the reaction temperature of step (<NUM>) is <NUM> to <NUM>.

In one or more embodiments of the present invention, R<NUM> and R<NUM> are identical, and step (<NUM>) and step (<NUM>) are combined into step (<NUM>'): making intermediate A and N-Ri-p-phenylenediamine react to prepare the compound of formula (I).

In one or more embodiments of the present invention, in the reaction of step (<NUM>'), alkali solution is added, and the reaction is first carried out at <NUM> to <NUM>, and then carried out at <NUM> to <NUM>.

The present invention also provides a rubber composition comprising the compound according to any embodiment of the present invention.

The present invention also provides a rubber article, which is prepared by using the rubber composition according to any embodiment of the present invention as a rubber component; preferably, the rubber product is a tire.

The present invention also provides use of the compound according to any embodiment of the present invention in improving anti-aging properties and/or discoloration resistance of a rubber or a rubber product; preferably, the rubber product is a tire.

In order to enable those skilled in the art to understand the characteristics and effects of the present invention, the following only provides general descriptions and definitions on the terms and terms mentioned in the specification and claims. Unless otherwise specified, all technical and scientific terms used herein shall have the usual meanings understood by those skilled in the art for the present invention. In case of conflict, the definition in the specification shall prevail.

The theory or mechanism described and disclosed herein, whether right or wrong, should not limit the scope of the present invention in any way, that is, the content of the present invention can be implemented without being restricted by any specific theory or mechanism.

In the present invention, all features such as numerical value, quantity, content and concentration defined in the form of numerical range or percentage range are only for brevity and convenience. Accordingly, the description of the numerical range or percentage range shall be deemed to have covered and specifically disclosed all possible sub-ranges and individual values (including integers and fractions) within the range.

Here, in order to make the description concise, not all possible combinations of various technical features in each embodiment or embodiment are described. Therefore, as long as there is no contradiction in the combination of these technical features, the various technical features in the various embodiments or examples can be combined arbitrarily, and all possible combinations should be considered within the scope of this specification.

Herein, alkyl refers to a straight-chain or branched monovalent saturated hydrocarbon group, usually containing <NUM> to <NUM> carbon atoms (C1~C16 alkyl), preferably containing <NUM> to <NUM> carbon atoms (C3~C16 alkyl). Examples of alkyl groups include but are not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, <NUM>,<NUM>-dimethylpentyl and tert-octyl. Herein, the alkyl group can be optionally substituted by aryl or cycloalkyl, and usually the number of substituents is one. Examples of substituted alkyl groups include but are not limited to cyclohexylmethyl, benzyl and phenethyl.

Herein, alkylene refers to a straight-chain or branched divalent saturated hydrocarbon group, usually containing <NUM> to <NUM> carbon atoms (C1~C16 alkylene), preferably containing <NUM> to <NUM> carbon atoms (C3~C16 alkylene). Examples of alkylene groups include but are not limited to methylene, ethylene and <NUM>,<NUM>-propylene.

Herein, cycloalkyl refers to a monovalent saturated hydrocarbon ring containing <NUM> to <NUM> carbon atoms, preferably containing <NUM> to <NUM> carbon atoms. Examples of cycloalkyl groups include but are not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and adamantyl. Herein, cycloalkyl may be optionally substituted with alkyl. The number of substituents may be one or two. Examples of substituted cycloalkyl include but are not limited to methylcyclohexyl.

Herein, cycloalkylene refers to a divalent saturated hydrocarbon ring containing <NUM> to <NUM> carbon atoms, preferably <NUM> to <NUM> carbon atoms. Examples of cycloalkylene include but are not limited to <NUM>,<NUM>-cyclopentanediyl and <NUM>,<NUM>-cyclohexanediyl.

Herein, aryl group refers to a monovalent group left after removing one hydrogen atom from an aromatic nucleus carbon of an aromatic hydrocarbon molecule. The number of ring carbon atoms of the aryl group is usually <NUM> to <NUM>. Exemplary aryl groups include phenyl and naphthyl. Aryl groups may be optionally substituted with alkyl. The number of substituents is usually one or two. Examples of substituted aryl groups include but are not limited to <NUM>-methylphenyl.

The present invention finds that the compound having the structure shown in formula (I) can provide better weather resistance, durability and discoloration resistance than conventional anti-degradants, and its specific structure is as follows:
<CHM>.

Preferred R is C3~C10 alkyl or C3~C10 cycloalkyl. In certain embodiments, R is a C3~C10 alkyl group, preferably a C3~C10 branched chain alkyl group or a C3~C10 cycloalkyl group, such as isopropyl, tert-butyl, tert-octyl or cyclohexyl.

Preferred R<NUM> and R<NUM> are each independently C3~C10 alkyl or phenyl. In a preferred embodiment, R<NUM> and R<NUM> are each independently C3~C10 branched chain alkyl or phenyl. In certain embodiments, R<NUM> and R<NUM> are each independently isopropyl, <NUM>,<NUM>-dimethylpentyl, or phenyl.

In certain embodiments of the present invention, R is tert-butyl or tert-octyl, and R<NUM> and R<NUM> are each independently <NUM>,<NUM>-dimethylpentyl or phenyl.

The compound of the structure represented by the formula (I) of the present invention can be prepared in three steps:.

In the first step, in order to improve the conversion rate of cyanuric chloride, excess NH<NUM>R can be used. Compared to cyanuric chloride, NH<NUM>R can generally be in excess of <NUM>% or less. In certain embodiments of the present invention, the excess of NH<NUM>R is equal to or less than <NUM>% or equal to or less than <NUM>%. Herein, unless otherwise specified, an excess of a certain substance means that the addition amount of the substance is greater than the addition amount of cyanuric chloride. The excess percentage value herein is based on the amount of substance. For example, when <NUM> mol of cyanuric chloride is used, the excess of NH<NUM>R of equal to or less than <NUM>% means that <NUM> mol to <NUM> mol of NH<NUM>R can be used.

In the reaction of the first step, alkaline solid powder is usually used as an acid binding agent to neutralize HCl generated during the reaction. The alkaline solid powder suitable for the present invention is not particularly limited, for example, it can be one or more of sodium carbonate, magnesium carbonate, calcium carbonate, calcium oxide, magnesium oxide, magnesium hydroxide and so on. Usually, in order to better neutralize HCl, excess basic solid powder can be added in the reaction of the first step. Compared to cyanuric chloride, the excess value of the basic solid powder is not particularly limited, for example, the excess value may be equal to or less than <NUM>%.

The reaction temperature in the first step is usually controlled at <NUM> to <NUM>. The reaction of the first step is usually carried out in a non-polar solvent, such as toluene, xylene, trimethylbenzene, chlorobenzene, methylcyclohexane, dichlorobenzene, trichlorobenzene, dimethylcyclohexane, trimethylbenzene and so on. The reaction time of the first step can be determined by detecting the progress of the reaction. Herein, the method for detecting the progress of the reaction may be known in the art, such as detecting whether the cyanuric chloride is completely reacted by gas chromatography (GC) or high performance liquid chromatography (HPLC). After the reaction, solid is filtered off to obtain a solution of intermediate A.

In the second step, in order to improve the conversion rate of intermediate A, excess N-R<NUM>-p-phenylenediamine can be used. Compared to cyanuric chloride, N-Ri-p-phenylenediamine can generally be in excess of equal to or less than <NUM>%. In certain embodiments of the present invention, the excess of N-R<NUM>-p-phenylenediamine is equal to or less than <NUM>%.

In the reaction of the second step, alkaline liquid is usually used as an acid binding agent. In the second step, an excessive amount of alkaline liquid is usually added, for example, alkali in the alkaline liquid can be in excess of equal to or less than <NUM>% or equal to or less than <NUM>% compared to cyanuric chloride. The alkaline liquid suitable for the present invention is not particularly limited, for example, it can be one or more of sodium hydroxide solution, potassium hydroxide solution, triethylamine, triisopropylamine, N-isopropyldiethylamine, N,N-diisopropyl ethylamine, etc. In the present invention, when the alkaline liquid is an aqueous solution of an inorganic alkali (such as sodium hydroxide solution, potassium hydroxide solution), its concentration is not particularly limited, usually being 10wt% to 50wt%, for example, it can be 25wt%.

The reaction temperature of the second step is usually controlled at <NUM> to <NUM>. The reaction of the second step is usually carried out in a non-polar solvent, such as toluene, xylene, trimethylbenzene, chlorobenzene, methylcyclohexane, dichlorobenzene, trichlorobenzene, dimethylcyclohexane, trimethylcyclohexane and so on. The reaction time of the second step can be determined by detecting the progress of the reaction, for example, using GC or HPLC to detect whether the content of N-Ri-p-phenylenediamine continues to decrease. After the reaction, through purification (for example, standing, removing aqueous phase, or washing with water), a solution of intermediate B is obtained.

In the third step, in order to improve the conversion rate of intermediate B, excess N-R<NUM>-p-phenylenediamine can be used. Compared to cyanuric chloride, N-R<NUM>-p-phenylenediamine can generally be in excess of equal to or less than <NUM>%. In certain embodiments of the present invention, the excess of N-R<NUM>-p-phenylenediamine is equal to or less than <NUM>%.

The reaction temperature of the third step is usually controlled at <NUM> to <NUM>. The third-step reaction is usually carried out in a non-polar solvent, such as toluene, xylene, trimethylbenzene, chlorobenzene, methylcyclohexane, dichlorobenzene, trichlorobenzene, dimethylcyclohexane, trimethylcyclohexane and so on. The time reaction of the third step can be determined by detecting the progress of the reaction, for example, using GC or HPLC to detect whether the content of N-R<NUM>-p-phenylenediamine continues to decrease. After the reaction is completed, alkaline liquid (such as sodium hydroxide solution, potassium hydroxide solution and so on) is added to neutralize and remove HCl. After neutralization, through purification (for example, removing aqueous phase, washing organic phase with water, distilling out solvent from organic substance to obtain a crude product, recrystallizing and purifying the crude product, and drying) to obtain the compound of formula (I).

When R<NUM> and R<NUM> of the compound of formula (I) are identical, the second step and the third step in the above preparation method can be combined into one step, that is, the compound of formula (I) is prepared by reacting intermediate A with N-Ri-p-phenylenediamine.

In the embodiment in which the second step and the third step are combined into one step (hereinafter referred to as the combined reaction), the addition of N-Ri-p-phenylenediamine added in the combined reaction is usually the sum of the additions of N-R<NUM>-p-phenylenediamine in the above-mentioned reactions of the second step and the third step. The combined reaction is usually carried out in the form of staged temperature control, that is, the reaction is carried out at <NUM> to <NUM> first, and then at <NUM> to <NUM>. The timing of switching the reaction temperature can be determined by detecting the reaction progress, for example, when the content of N-Ri-p-phenylenediamine is detected by GC or HPLC to be reduced to half of the added amount, the temperature is switched from <NUM> to <NUM> to <NUM> to <NUM>. The combined reaction is usually carried out in a non-polar solvent, such as toluene, xylene, trimethylbenzene, chlorobenzene, methylcyclohexane, dichlorobenzene, trichlorobenzene, dimethylcyclohexane, trimethylcyclohexane and so on. The total time of the combined reaction can be determined by detecting the progress of the reaction, such as using GC or HPLC to detect whether the content of N-Ri-p-phenylenediamine continues to decrease. In the combined reaction, alkaline liquid (such as a one or more of sodium hydroxide solution, potassium hydroxide solution, triethylamine, triisopropylamine, N-isopropyldiethylamine, N,N-diisopropylethylamine, etc.) is usually used as an acid binding agent. After the reaction is completed, alkaline liquid can be added to neutralize and remove HCl, and after purification (for example, removing aqueous phase, washing organic phase with water, distilling out solvent from organic substance to obtain a crude product, recrystallizing and purifying the crude product, and drying) to obtain the compound of formula (I).

The compounds of the present invention can provide improved aging resistance and discoloration resistance for rubber compositions. Accordingly, the present invention also provides a rubber composition comprising one or more of the compounds of formula I described herein. Typically, the rubber composition also comprises a diene elastomer, a reinforcing filler and a crosslinker.

A diene elastomer refers to an elastomer with its monomers comprising a diene (such as butadiene and isoprene). Diene elastomers suitable for the present invention are known in the field, including but not limited to one or more selected from natural rubber (NR), butadiene rubber (BR), isoprene rubber, styrene butadiene rubber (SBR), chloroprene rubber (CR), nitrile butadiene rubber (NBR), isoprene/butadiene copolymer, isoprene/styrene copolymer and isoprene/butadiene/styrene copolymer. In some embodiments, in the rubber composition of the present invention, the diene elastomer consists of natural rubber (such as SCR5) and butadiene rubber (such as BR9000), and the mass ratio of the natural rubber to the butadiene rubber may be in the ranges of from <NUM>:<NUM> to <NUM>:<NUM>, from <NUM>:<NUM> to <NUM>:<NUM>, from <NUM>:<NUM> to <NUM>:<NUM>, from <NUM>:<NUM> to <NUM>:<NUM>, from <NUM>:<NUM> to <NUM>:<NUM>, or <NUM>: <NUM>.

Usually, based on <NUM> parts by mass of diene elastomer, in the rubber composition, the amount of the compound of formula I is <NUM>-<NUM> parts by mass, such as <NUM>-<NUM> parts by mass, <NUM>-<NUM> parts by mass, or <NUM>-<NUM> parts by mass.

The rubber composition may also comprise other conventionally used components, including but not limited to reinforcing fillers, aids, crosslinkers and promoters, etc. The amounts of reinforcing fillers, aids, crosslinkers and promoters can be conventional amounts in the art.

Reinforcing fillers may be carbon black, titanium oxide, magnesium oxide, calcium carbonate, magnesium carbonate, aluminum hydroxide, magnesium hydroxide, clay, talc and so on. Generally, reinforcing fillers are used in an amount of <NUM> to <NUM> parts by weight per <NUM> parts by weight of diene elastomer.

Aids may include softeners used to improve processability and other properties. Softeners may include petroleum softeners, such as aromatic oil, processing oil, lubricating oil, paraffin, liquid paraffin, petroleum asphalt, and vaseline, etc., and/or fatty oil softeners, such as castor oil, flaxseed oil, rapeseed oil, coconut oil, wax (e.g., beewax, carnauba wax, and lanolin), tall oil, linoleic acid, palmitic acid, stearic acid and lauric acid, etc. Aids may also include activators, such as zinc oxide, which can speed up the vulcanization rate and improve the thermal conductivity, wear resistance, and tear resistance of rubber. Usually, <NUM> to <NUM> parts by mass of aids are used per <NUM> parts by mass of diene elastomer, for example, <NUM> to <NUM> parts by mass of aromatic oil, <NUM> to <NUM> parts by mass of zinc oxide and <NUM> to <NUM> parts by mass of stearic acid are used.

A crosslinker can be sulfur. Generally, crosslinkers are used in an amount of <NUM> to <NUM> parts by weight per <NUM> parts by weight of diene elastomer.

Promoters are generally vulcanization accelerators, which may be selected from at least one of sulfonamide, thiazole, thiuram, thiourea, guanidine, dithiocarbamate, aldimine, aldehyde ammonia, imidazoline, and xanthic acid vulcanization accelerators. For example, the promoter may be N-tert-butylbenzothiazole-<NUM>-sulphenamide (NS). Generally, promoters are used in an amount of <NUM> to <NUM> parts by weight per <NUM> parts by weight of diene elastomer.

In addition, when necessary, a plasticizer may be used in the rubber composition of the present invention, which includes, but not limited to, dimethyl phthalate (DMP), diethyl phthalate (DEP), dibutyl phthalate (DBP), diheptyl phthalate (DHP), dioctyl phthalate (DOP), di-isononyl phthalate (DINP), di-isodecyl phthalate (DIDP), butyl benzyl phthalate (BBP), dilauryl phthalate (DWP), and dicyclohexyl phthalate (DCHP), etc. The plasticizer may be used in a conventional amount that is known in the art.

The rubber product of the present invention can be prepared by conventional methods. For example, it can be prepared by a two-stage mixing method as follows: in the first stage, an internal mixer is used to mix diene elastomers, reinforcing fillers, aids and anti-degradants, and the rubber discharge temperature is <NUM> or higher; in the second stage, an open mill is used to mix the rubber with sulfur and promoters.

Generally, a diene elastomer is added into a thermo-mechanical mixer, such as an internal mixer at first. After kneading for a while, a reinforcing filler, an aid, and an anti-degradant are added and the mixture is kept on being kneaded until the mixture is homogeneous. The reinforcing filler, the aid, and the anti-degradant may be added in batches. The temperature during kneading is controlled to between <NUM> and <NUM>, preferably between <NUM> and <NUM>. Then, the mixture is cooled to <NUM> or lower. A crosslinker and a promoter are added to the mixture and a second kneading is performed during which the temperature is controlled to <NUM> or lower, e.g. <NUM>, and an unvulcanized rubber is obtained. Tablet pressing can be carried out on the kneaded rubber composition before vulcanization. The unvulcanized rubber of the present invention can be vulcanized by a conventional vulcanization method to obtain a vulcanized rubber. The vulcanization (curing) temperature is generally <NUM> to <NUM>, such as <NUM>. The vulcanization time depends on the vulcanization temperature, vulcanization system, and vulcanization kinetics, and is generally from <NUM> minutes to <NUM> minutes, such as <NUM> minutes.

When the compound of the present invention is used in rubber articles, especially rubber tires, it can render the rubber articles or rubber tires more excellent anti-aging properties; in addition, compared with the existing anti-degradant products, the rubber articles or rubber tires comprising the compound of the present invention is not easy to cause surface pollution and discoloration, and has excellent discoloration resistance. Therefore, the present invention also provides a rubber article prepared by using the rubber composition described herein as a rubber component. The rubber article may be a tire, a rubber overshoe, a sealing strip, an acoustic panel, or a crash pad. In some embodiments, the rubber article is a tire, such as tread, a belt ply, and a sidewall of a tire. As a belt ply of a tire, the rubber article may further comprise a reinforcing material conventionally used in the art in addition to the rubber composition of the present invention. The present invention also provides the use of the rubber compositions described herein in improving the aging resistance and/or discoloration resistance of a rubber or a rubber article.

The present invention is illustrated by way of specific examples below. It should be understood that these examples are merely explanatory and is not intended to limit the scope of the present invention. Unless otherwise specified, the methods, reagents, and materials used in the examples are conventional in the art. The formulations used in the examples are commercially available.

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> toluene, <NUM> sodium carbonate solid powder is added, <NUM> toluene solution of isopropylamine (<NUM>. 67mol isopropylamine+<NUM> toluene) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. The solid is filtered out, and a colorless and transparent solution of intermediate A1 is obtained.

<NUM> N-phenyl-p-phenylenediamine (<NUM>. 77mol) is dissolved in <NUM> toluene, the solution is heated to <NUM>, the toluene solution of the intermediate A1 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> sodium hydroxide solution (25wt%) is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when the content of N-phenyl-p-phenylenediamine is no longer decreased, the reaction is stopped and left standing. The aqueous phase is removed to obtain a toluene solution containing intermediate B <NUM>.

<NUM> N-phenyl-p-phenylenediamine (<NUM>. 72mol) is added to the toluene solution of intermediate B11 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of N-phenyl-p-phenylenediamine is no longer decreased, the temperature is lowered, and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization, the aqueous phase is removed, the organic phase is washed with water, and then toluene is distilled out to obtain a crude product. Then the crude product is recrystallized with petroleum ether, and dried to obtain <NUM> (yield <NUM>%) <NUM>-isopropylamine-<NUM>,<NUM>-bis(<NUM>-anilinoaniline)-<NUM>,<NUM>,<NUM>-triazine (compound I-<NUM>).

<NUM>H-HMR (<NUM>, DMSO-D<NUM>, δ ppm): <NUM>(s, <NUM>), <NUM>(s, <NUM>), <NUM>(br, <NUM>), <NUM>(t, <NUM>), <NUM>( q, <NUM>), <NUM>(t, <NUM>), <NUM>(s, <NUM>), <NUM>(s, <NUM>), <NUM>(s, <NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> xylene, <NUM> ultrafine calcium carbonate solid powder is added, <NUM> xylene solution of isopropylamine (<NUM>. 65mol isopropylamine+<NUM> xylene) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out, and a colorless and transparent intermediate A1 solution is obtained.

<NUM> N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine (<NUM>. 74mol) is dissolved in <NUM> xylene, the solution is heated to <NUM>, xylene solution of the intermediate A1 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> potassium hydroxide solution (25wt%) is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when the content of N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine is no longer reduced, the reaction is stopped and left standing. The aqueous phase is removed to obtain a xylene solution containing intermediate B12.

<NUM> N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine (<NUM>. 74mol) is added to the xylene solution of the intermediate B12 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine is no longer decreased, the temperature is lowered, and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization, the organic phase is washed with water, and then xylene is distilled out to obtain a crude product. Then the crude product is recrystallized with petroleum ether and dried to obtain <NUM> (yield <NUM>%) <NUM>-isopropylamine-<NUM>,<NUM>-bis(<NUM>-(<NUM>,<NUM>-dimethylpentylamino)aniline)-<NUM>,<NUM>,<NUM>-triazine (compound I-<NUM>).

<NUM>H-HMR (<NUM>, DMSO-D6, δ ppm): <NUM>(s, <NUM>), <NUM>(d, <NUM>), <NUM>(d, <NUM>), <NUM>(S, <NUM>), <NUM>(t, <NUM>), <NUM>-<NUM>(m, <NUM>), <NUM>-<NUM>(m, <NUM>), <NUM>-<NUM>(m, <NUM>), <NUM>(d, <NUM>), <NUM>(q, <NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> trimethylbenzene, <NUM> ultrafine magnesium carbonate solid powder is added, <NUM> trimethylbenzene solution of tert-butylamine (<NUM>. 67mol tert-butylamine+<NUM> toluene) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out, and a colorless and transparent solution of intermediate A2 is obtained.

<NUM> N-phenyl-p-phenylenediamine (<NUM>. 71mol) is dissolved in <NUM> trimethylbenzene, the solution is heated to <NUM>, the trimethylbenzene solution of the intermediate A2 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> triethylamine is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when the content of N-phenyl-p-phenylenediamine is no longer decreased, the reaction is stopped. After washing with water, a trimethylbenzene solution containing intermediate B21 is obtained.

<NUM> N-phenyl-p-phenylenediamine (<NUM>. 67mol) is added to the trimethylbenzene solution of intermediate B21 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of N-phenyl-p-phenylenediamine is no longer decreased, the temperature is lowered and the reaction is stopped. <NUM> triethylamine is added for neutralization, and after washing with water, trimethylbenzene is distilled out to obtain a crude product. Then the crude product is recrystallized with petroleum ether, and dried to obtain <NUM> (yield <NUM>%) <NUM>-tert-butylamine-<NUM>,<NUM>-bis(<NUM>-anilinoaniline)-<NUM>,<NUM>,<NUM>-triazine (compound I-<NUM>).

<NUM>H-NMR (<NUM>, DMSO-D6, δ PPm): <NUM>(s, <NUM>), <NUM>(s, <NUM>), <NUM>(br, <NUM>), <NUM>(t, <NUM>), <NUM>(q, <NUM>), <NUM>(t, <NUM>), <NUM>(s, <NUM>), <NUM>(s, <NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> chlorobenzene, <NUM> calcium oxide solid powder is added, <NUM> toluene solution of tert-butylamine (<NUM>. 67mol tert-butylamine+<NUM> chlorobenzene) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out, and a colorless and transparent solution of intermediate A2 is obtained.

<NUM> N-isopropyl-p-phenylenediamine (<NUM>. 7mol) is dissolved in <NUM> chlorobenzene, the solution is heated to <NUM>, the chlorobenzene solution of the intermediate A2 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> triisopropylamine is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when the content of N-isopropyl-p-phenylenediamine is no longer decreased, the reaction is stopped and left standing. The aqueous phase is removed to obtain a chlorobenzene solution containing intermediate B22.

<NUM> N-isopropyl-p-phenylenediamine (<NUM>. 76mol) is added to the chlorobenzene solution of intermediate B22 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of N-isopropyl-p-phenylenediamine is no longer decreased, the temperature is lowered and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization, the organic phase is washed with water, and then chlorobenzene is distilled out to obtain a crude product. Then the crude product is recrystallized with petroleum ether and dried to obtain <NUM> (yield <NUM>%) <NUM>-tert-butylamine-<NUM>,<NUM>-bis(<NUM>-isopropylaminoaniline)-<NUM>,<NUM>,<NUM>-triazine (compound <NUM>-<NUM>).

<NUM>H-HMR (<NUM>, DMSO- D6, δ ppm): <NUM>(s, <NUM>), <NUM>(d, <NUM>), <NUM>(d, <NUM>), <NUM>(S, <NUM>), <NUM>(d, <NUM>), <NUM>(d, <NUM>), <NUM>-<NUM>(m, <NUM>), <NUM>(q, <NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> dichlorobenzene, <NUM> ultrafine magnesium oxide solid powder is added, <NUM> dichlorobenzene solution of tert-butylamine (<NUM>. 7mol tert-butylamine+<NUM> dichlorobenzene) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out, and a colorless and transparent solution of intermediate A2 is obtained.

<NUM> N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine (<NUM>. 7mol) is dissolved in <NUM> dichlorobenzene, the solution is heated to <NUM>, dichlorobenzene solution of the intermediate A2 obtained in step (<NUM>) is added with vigorous stirring, at the same time <NUM> potassium hydroxide solution (25wt%) is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when the content of N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine is no longer decreased, the reaction is stopped and left standing. The aqueous phase is removed to obtain a dichlorobenzene solution containing intermediate B23. (<NUM>) Synthesis of Compound I-<NUM>.

<NUM> N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine (<NUM>. 72mol) is added to the dichlorobenzene solution of intermediate B23 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine is no longer decreased, the temperature is lowered and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization to obtain a crude product. Then the crude product is recrystallized with petroleum ether, and dried to obtain <NUM> (yield <NUM>%) <NUM>-tert-butylamine-<NUM>,<NUM>-bis(<NUM>-(<NUM>,<NUM>-dimethylpentylamino)aniline)-<NUM>,<NUM>,<NUM>-triazine (compound <NUM>-<NUM>).

<NUM>H-NMR(<NUM>, DMSO-D6, δ ppm): <NUM>(s, <NUM>), <NUM>(d, <NUM>), <NUM>(d, <NUM>), <NUM>(S, <NUM>), <NUM>(d, <NUM>), <NUM>-<NUM>(m, <NUM>), <NUM>-<NUM>(m, <NUM>), <NUM>-<NUM>(m, <NUM>), <NUM>(d, <NUM>), <NUM>(q, <NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> methylcyclohexane, <NUM> ultrafine magnesium hydroxide solid powder is added, <NUM> methylcyclohexane solution of tert-butylamine (<NUM>. 67mol tert-butylamine+<NUM> methylcyclohexane) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out, and a colorless and transparent solution of intermediate A2 is obtained.

<NUM> N-phenyl-p-phenylenediamine (<NUM>. 67mol) is dissolved in <NUM> methylcyclohexane, the solution is heated to <NUM>, the methylcyclohexane solution of the intermediate A2 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> potassium hydroxide solution (25wt%) is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when the content of N-phenyl-p-phenylenediamine remains unchanged, the reaction is stopped. After washing with water, a methylcyclohexane solution containing intermediate B21 is obtained.

<NUM> N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine (<NUM>. 64mol) is added to the methylcyclohexane solution of the intermediate B21 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine is no longer reduced, the temperature is lowered and the reaction is stopped. <NUM> of sodium hydroxide (25wt%) is added for neutralization. After washing with water, methylcyclohexane is distilled out to obtain a crude product. Then the crude product is recrystallized with petroleum ether and dried to obtain <NUM> (yield <NUM>%) <NUM>-tert-butylamine-<NUM>-(<NUM>-anilinoaniline)-<NUM>-(<NUM>-(<NUM>,<NUM>-dimethylpentylamino)aniline)-<NUM>,<NUM>,<NUM>-triazine (compound <NUM>-<NUM>).

<NUM>H-NMR(<NUM>, DMSO-D6, δPPm): <NUM>(d, <NUM>), <NUM>(s, <NUM>), <NUM>(d, <NUM>), <NUM>(d, <NUM>), <NUM>(t, <NUM>), <NUM>(t, <NUM>), <NUM>(t, <NUM>), <NUM>( d, <NUM>), <NUM>(s, <NUM>), <NUM> (d, <NUM>), <NUM>(m, <NUM>), <NUM>-<NUM>(m, <NUM>), <NUM>(s, <NUM>), <NUM>-<NUM>(m, <NUM>), <NUM>(d, <NUM>), <NUM>(q, <NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> trichlorobenzene, <NUM> sodium carbonate solid powder is added, <NUM> trichlorobenzene solution of tert-octylamine (<NUM>. 67mol tert-octylamine+<NUM> trichlorobenzene) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dripping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out, and a colorless and transparent solution of intermediate A3 is obtained.

<NUM> N-phenyl-p-phenylenediamine (<NUM>. 7mol) is dissolved in <NUM> trichlorobenzene, the mixture is heated to <NUM>, the trichlorobenzene solution of the intermediate A3 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> potassium hydroxide (25wt%) is add dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when the content of N-phenyl-p-phenylenediamine is no longer decreased, the reaction is stopped and left standing. The aqueous phase is removed to obtain a trichlorobenzene solution containing intermediate B31.

<NUM> N-phenyl-p-phenylenediamine (<NUM> mol) is added to the trichlorobenzene solution of the intermediate B31 obtained in step (<NUM>), the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of N-phenyl-p-phenylene is no longer decreased, the temperature is lowered and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization, the aqueous phase is removed, the organic phase is distilled to remove trichlorobenzene, and a crude product is obtained. Then the crude product is recrystallized with petroleum ether and dried to obtain <NUM> (yield <NUM>%) <NUM>-tert-octylamine-<NUM>,<NUM>-bis(<NUM>-anilinoaniline)-<NUM>,<NUM>,<NUM>-triazine (compound I-<NUM>).

<NUM>H-NMR(<NUM>, DMSO-D6, δ ppm): <NUM>(d,<NUM>), <NUM>(s,<NUM>), <NUM>(s,<NUM>), <NUM>(t,<NUM>), <NUM>(q,<NUM>), <NUM>(t,<NUM>), <NUM>(br,<NUM>), <NUM>(s,<NUM>), <NUM>(s,<NUM>), <NUM>(s,<NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> dimethylcyclohexane, <NUM> ultrafine sodium carbonate solid powder is added, <NUM> dimethylcyclohexane solution of tert-octylamine (<NUM>. 67mol tert-octylamine+<NUM> dimethylcyclohexane) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued to react for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out, and a colorless transparent solution of intermediate A3 is obtained.

<NUM> N-isopropyl-p-phenylenediamine (<NUM>. 7mol) is dissolved in <NUM> dimethylcyclohexane, the solution is heated to <NUM>, the dimethylcyclohexane solution of the intermediate A3 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> sodium hydroxide solution (25wt%) is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when the content of N-isopropyl-p-phenylenediamine is no longer decreased, the reaction is stopped and left standing. The aqueous phase is removed to obtain a dimethylcyclohexane solution containing intermediate B32.

<NUM> N-isopropyl-p-phenylenediamine (<NUM>. 72mol) is added to the dimethylcyclohexane solution of the intermediate B32 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of propyl-p-phenylenediamine is no longer decreased, the temperature is lowered and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization, the organic phase is washed with water, and then dimethylcyclohexane is distilled out to obtain a crude product. Then the crude product is recrystallized with petroleum ether and dried to obtain <NUM> (yield <NUM>%) <NUM>-tert-octylamine-<NUM>,<NUM>-bis(<NUM>-isopropylaminoaniline)-<NUM>,<NUM>,<NUM>-triazine (Compound I- <NUM>).

<NUM>H-HMR(<NUM>, DMSO-D6, δ ppm): <NUM>(s,<NUM>), <NUM>(d,<NUM>), <NUM>(d,<NUM>), <NUM>(S,<NUM>), <NUM>(d,<NUM>), <NUM>(d,<NUM>), <NUM>(s,<NUM>), <NUM>-<NUM> (m,<NUM>), <NUM>(s,<NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> trimethylcyclohexane, <NUM> sodium carbonate solid powder is added, <NUM> trimethylcyclohexane solution of tert-octylamine (<NUM>. 67mol tert-octylamine+<NUM> trimethylcyclohexane) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out, and a colorless and transparent solution of intermediate A3 is obtained.

<NUM> N-phenyl-p-phenylenediamine (<NUM>. 7mol) is dissolved in <NUM> trimethylcyclohexane, the solution is heated to <NUM>, the trimethylcyclohexane solution of the intermediate A3 obtained in step (<NUM>) is added dropwise under vigorous stirring, at the same time <NUM> potassium hydroxide (25wt%) is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when the content of N-phenyl-p-phenylenediamine is no longer decreased, the reaction is stopped and left standing. The aqueous phase is removed to obtain a trimethylcyclohexane solution containing intermediate B31.

<NUM> N-isopropyl-p-phenylenediamine (<NUM>. 7mol) is added to the trimethylcyclohexane solution of the intermediate B31 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of propyl-p-phenylenediamine is no longer decreased, the temperature is lowered and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization, and after washing with water, trimethylcyclohexane is distilled out to obtain a crude product. Then the crude product is recrystallized with petroleum ether and dried to obtain <NUM> (yield <NUM>%) <NUM>-tert-octylamine-<NUM>-(<NUM>-anilinoaniline)-<NUM>-(<NUM>-isopropylaminoaniline)-<NUM>,<NUM>,<NUM>-triazine (compound I-<NUM>).

<NUM>H-HMR(<NUM>, DMSO-D6, δ ppm): <NUM>(q,<NUM>), <NUM>(s,<NUM>), <NUM> (s,<NUM>), <NUM>(s,<NUM>), <NUM>(t,<NUM>), <NUM> (t,<NUM>), <NUM>(t,<NUM>), <NUM>(d,<NUM>), <NUM>(d, <NUM>), <NUM>(d,<NUM>), <NUM>(m,<NUM>), <NUM>(m,<NUM>), <NUM>-<NUM>(m,<NUM>), <NUM>(s,<NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> xylene, <NUM> sodium carbonate solid powder is added, <NUM> xylene solution of tert-octylamine (<NUM>. 67mol of tert-octylamine + <NUM> of xylene) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out the solid, and a colorless and transparent solution of intermediate A3 is obtained.

<NUM> N-phenyl-p-phenylenediamine (<NUM> mol) is dissolve in <NUM> xylene, the solution is heated to <NUM>, the xylene solution of the intermediate A3 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> potassium hydroxide (25wt%) is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for HPLC detection, and when intermediate A3 can not be detected, the reaction is stopped. After washing with water, a xylene solution containing intermediate B31 is obtained.

<NUM> N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine (<NUM>. 64mol) is added to the xylene solution of the intermediate B31 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine is no longer decreased, the temperature is lowered and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization. After washing with water, xylene is distilled out to obtain a crude product Then the crude product is recrystallized with petroleum ether and dried to obtain <NUM> (yield <NUM>%) <NUM>-tert-octylamine-<NUM>-(<NUM>-anilinoaniline)-<NUM>-(<NUM>-(<NUM>,<NUM>-dimethylpentylamino)aniline)-<NUM>,<NUM>,<NUM>-triazine (compound I-<NUM>).

<NUM>H-NMR(<NUM>, DMSO-D6, δ ppm): <NUM>(q,<NUM>), <NUM>(s,<NUM>), <NUM>(s,<NUM>), <NUM>(s,<NUM>), <NUM>(t,<NUM>), <NUM>(t,<NUM>), <NUM>(t,<NUM>), <NUM>(d,<NUM>), <NUM>(d, <NUM>), <NUM>(d,<NUM>), <NUM>(m,<NUM>), <NUM>(s,<NUM>), <NUM>(m,<NUM>), <NUM>(s,<NUM>), <NUM>-<NUM>(m,<NUM>), <NUM>(d,<NUM>), <NUM>(s,<NUM>), <NUM>(q,<NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> xylene, <NUM> sodium carbonate solid powder is added, <NUM> xylene solution of tert-octyl amine (<NUM>. 67mol tert-octyl amine+<NUM> xylene) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out, and a colorless and transparent solution of intermediate A3 is obtained.

<NUM> N-isopropyl-p-phenylenediamine (<NUM> mol) is dissolved in <NUM> xylene, the solution is heated to <NUM>, the xylene solution of the intermediate A3 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> sodium hydroxide solution (25wt%) is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when intermediate A3 can not be detected, the reaction is stopped and left standing. The aqueous phase is removed to obtain a xylene solution containing intermediate B32.

<NUM> N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine (<NUM>. 7mol) is added to the xylene solution of the intermediate B32 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine is no longer decreased, the temperature is lowered and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization, the organic phase is washed with water, and xylene is distilled out to obtain a crude product. Then the crude product is recrystallized with petroleum ether and dried to obtain <NUM> (yield <NUM>%) <NUM>-tert-octylamine-<NUM>-(<NUM>-isopropylaminoaniline)-<NUM>-(<NUM>-(<NUM>,<NUM>-dimethylpentylamino)aniline)-<NUM>,<NUM>,<NUM>-triazine (compound <NUM>-<NUM>).

<NUM>H-HMR(<NUM>, DMSO-D6, δ ppm): <NUM>(d,<NUM>), <NUM>(s,<NUM>), <NUM>(d,<NUM>), <NUM>(br,<NUM>), <NUM>(t,<NUM>), <NUM>-<NUM>(m,<NUM>), <NUM>-<NUM>(m,<NUM>), <NUM>-<NUM>(d,<NUM>), <NUM>(s,<NUM>), <NUM>(q, <NUM>).

<NUM> N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine (<NUM>. 7mol) is dissolved in <NUM> xylene, the solution is heated to <NUM>, the xylene solution of the intermediate A3 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> sodium hydroxide solution (25wt%) is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. Samples are took for GC detection, and when intermediate A3 can not be detected, the reaction is stopped and left standing. The aqueous phase is removed to obtain a xylene solution containing intermediate B33.

<NUM> N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine (<NUM>. 74mol) is added to the xylene solution of the intermediate B33 obtained in step (<NUM>), and the mixture is heated to <NUM> for reaction. GC detection is performed, and when the content of N-<NUM>,<NUM>-dimethylpentyl-p-phenylenediamine is no longer decreased, the temperature is lowered and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization, the organic phase is washed with water, and xylene is distilled out to obtain a crude product. Then the crude product is recrystallized with petroleum ether and dried to obtain <NUM> (yield <NUM>%) <NUM>-tert-octylamine-<NUM>,<NUM>-bis(<NUM>-(<NUM>,<NUM>-dimethylpentylamino)aniline)-<NUM>,<NUM>,<NUM>-triazine (compound I-<NUM>).

<NUM>H-NMR(<NUM>, DMSO-D6, δ ppm): <NUM>(d,<NUM>), <NUM>(s,<NUM>), <NUM>(d,<NUM>), <NUM>(br,<NUM>), <NUM>(d, <NUM>), <NUM>-<NUM>(m, <NUM>), <NUM>(s,<NUM>), <NUM>-<NUM>(m,<NUM>), <NUM>(s,<NUM>), <NUM>-<NUM>(m,<NUM>), <NUM>-<NUM>(d,<NUM>), <NUM>(s,<NUM>), <NUM>(q, <NUM>).

<NUM> cyanuric chloride (<NUM>. 64mol) is dissolved in <NUM> toluene, <NUM> sodium carbonate solid powder is added, <NUM> toluene solution of cyclohexylamine (<NUM>. 67mol cyclohexylamine+<NUM> toluene) is added dropwise under vigorous stirring at <NUM> for <NUM>, and the reaction is continued for <NUM> after dropping. Samples are took for GC detection, and when cyanuric chloride can not be detected, the reaction is stopped. Solid is filtered out, and a colorless and transparent solution of intermediate A4 is obtained.

<NUM> N-phenyl-p-phenylenediamine (<NUM>. 7mol) is dissolved in <NUM> toluene, the solution is heated to <NUM>, the toluene solution of the intermediate A4 obtained in step (<NUM>) is added dropwise with vigorous stirring, at the same time <NUM> sodium hydroxide solution (25wt%) is added dropwise for <NUM>~<NUM>, and the temperature is kept for <NUM>. sSample are took for GC detection, and when intermediate A4 can not be detected, the reaction is stopped and left standing. The aqueous phase is removed to obtain a toluene solution containing intermediate B43.

<NUM> N-phenyl-p-phenylenediamine (<NUM>. 72mol) is added to the toluene solution of the intermediate B43 obtained in step (<NUM>), and the mixture is heated to <NUM> for the reaction. GC detection is performed, and when the content of N-phenyl-p-phenylenediamine is no longer decreased, the temperature is lowered and the reaction is stopped. <NUM> sodium hydroxide solution (25wt%) is added for neutralization, the organic phase is washed with water and then toluene is distilled out to obtain a crude product. Then the crude product is recrystallized with petroleum ether, and dried to obtain <NUM> (yield <NUM>%) <NUM>-cyclohexylamine-<NUM>,<NUM>-bis(<NUM>-anilinoaniline)-<NUM>,<NUM>,<NUM>-triazine (compound <NUM>-<NUM>).

<NUM>H-NMR(<NUM>, DMSO-D6, δ ppm): <NUM>(s,<NUM>), <NUM>(s,<NUM>), <NUM>(br, <NUM>), <NUM>(t,<NUM>), <NUM>( q, <NUM>), <NUM>(t,<NUM>), <NUM>(s,<NUM>), <NUM>-<NUM>(m,<NUM>), <NUM>(br,<NUM>).

The rubber compositions of testing examples <NUM>-<NUM> are prepared according to the formula shown in Table <NUM> by a method specifically comprising the following steps:.

The sources of the materials in Table <NUM> are as follows:.

The ozone resistance and discoloration resistance of the vulcanized rubber sheets of testing examples <NUM> to <NUM> are evaluated according to the following methods, and the results are shown in Table <NUM>.

Under the conditions of temperature of <NUM>, ozone concentration of <NUM> pphm, and elongation of <NUM>%, the test sheets of various rubber compositions are subjected to ozone deterioration test. After <NUM> hours, the deterioration state of the test sheet is examined. The ozone resistance grade is based on the density of cracks formed and is judged by:.

The vulcanized rubber sheet is packed into a ziplock bag, the rubber sheet is pressed against the bag, and the color change of the bag is observed after two weeks of exposure to outdoor. The evaluation criteria of the discoloration resistance grade are shown in Table <NUM>.

Claim 1:
A compound represented by the following formula (I):
<CHM>
Wherein:
R is C3~C16 alkyl, C3~C16 alkyl substituted by C3~C10 cycloalkyl, C3~C10 cycloalkyl or C3~C10 cycloalkyl substituted by C3~C16 alkyl;
R<NUM> and R<NUM> are identical or different, each being independently selected from C3~C10 alkyl, C3~C10 alkyl substituted by C3~C10 cycloalkyl or C6~C14 aryl, C3~C10 cycloalkyl, C3~C10 cycloalkyl substituted by C3~C10 alkyl, C6~C14 aryl and C6~C14 aryl substituted by C3~C10 alkyl.