O-alkylated highly sterically hindered antioxidants

Abstract

The present invention relates to a composition comprising a compound of general formula (I), wherein R 1 is a linear or branched C1 to C24 alkyl group, R 2 is a C1-C8 alkyl group, R 3 is a C1-C8 alkyl group. The present invention also relates to industrial products such as additive blends, engine oils and polymer compositions comprising this compound of general formula (I) and to the use of compounds of general formula (I) as additives in industrial products such as additive blends, engine oils and polymer compositions. TIFF2024524020000016.tif27170

Description

[Technical field]

[0001] The present invention relates to compositions comprising O-alkylated highly sterically hindered antioxidants. The present invention also relates to processes for the preparation of O-alkylated highly sterically hindered antioxidants, industrial products comprising such compositions, and the use of O-alkylated highly sterically hindered antioxidants as additives in industrial products. [Background technology]

[0002] As major industrial products, lubricants, such as those used in various machines, are susceptible to oxidative degradation during storage, transportation, and use, especially when such lubricants are exposed to high temperatures and iron-catalyzed environments that greatly promote their oxidation. This oxidation, if not controlled, can contribute to the formation of corrosive acidic products, sludge, varnish, resins, and other oil-insoluble products, resulting in the loss of the specified physical and tribological properties of the lubricant. Therefore, in order to extend the useful life of the lubricant, it is common practice to include antioxidants in the lubricant to prevent oxidation at least to some extent.

[0003] Lubricant compositions containing various diarylamine or phenolic compounds as antioxidants are widely known in the art. For example, US Patent No. 5,892,097 discloses the preparation of highly sterically hindered phenolic compounds and their use as antioxidants. These antioxidants are prepared by reacting an alcohol such as isooctanol with methyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate to form isooctyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate in a transesterification reaction. However, the antioxidant performance of the highly sterically hindered phenolic compounds obtained by such a reaction and known from the prior art can still be improved. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] U.S. Pat. No. 5,892,097 Summary of the Invention [Problem to be solved by the invention]

[0005] It is therefore an object of the present invention to overcome the shortcomings of the prior art relating to compositions used to improve the properties of industrial products such as engine oils, particularly with regard to their oxidative stability.

[0006] In particular, it is an object of the present invention to provide compositions which, when added to a lubricant, such as an engine oil, either as a separate additive or as a component in a so-called "additive package", improve the properties of the lubricant, particularly with regard to oxidative stability.

[0007] A contribution to at least partially solving at least one, preferably two or more of the above stated objects is made by the independent claims. The dependent claims provide preferred embodiments which contribute at least partially to solving at least one of the objects. [Means for solving the problem]

[0008] The contribution to solving at least one of the objects of the present invention is i) A compound of general formula (I), [ka] During the ceremony, R 1 is a linear or branched C1-C24 alkyl group, preferably a methyl group or a C7-C9 alkyl group, more preferably a methyl group or a linear or branched C8-alkyl group, most preferably a branched octyl group, most preferably an isooctyl group or a 2-ethylhexyl group or both, R 2 is a C1 to C8 alkyl group, preferably a methyl group or an ethyl group, more preferably a methyl group; R3 is a C1 to C8 alkyl group, preferably a C1 to C4 alkyl group, more preferably a tert-butyl group. This is achieved by a composition comprising the compound.

[0009] Surprisingly, it has been found that O-alkylated highly sterically hindered compounds having the general formula (I) are particularly effective antioxidants compared to their corresponding phenolic derivatives. Not only are the pure or substantially pure O-alkylated highly sterically hindered compounds themselves, preferably the pure O-methylated highly sterically hindered compounds, effective antioxidants, but also mixtures of commercial antioxidants based on, for example, isooctyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate to which a certain amount of the corresponding O-alkylated derivative (i.e. isooctyl-3,5-di-tert-butyl-4-alkoxy-hydrocinnamate, preferably isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate) is added.

[0010] The compound of general formula (I) I) providing a compound of general formula (I), [ka] During the ceremony, R 1 is a linear or branched C1-C24 alkyl group, preferably a methyl group or a C7-C9 alkyl group, more preferably a methyl group or a linear or branched C8-alkyl group, most preferably a branched octyl group, most preferably an isooctyl group or a 2-ethylhexyl group or both, R 3 is a C1 to C8 alkyl group, preferably a C1 to C4 alkyl group, more preferably a tert-butyl group. The process and II) The compound provided in process step I) is reacted with at least one alkyl group R 2 with an alkylating agent comprising R2 is a C1 to C8 alkyl group, preferably a methyl group or an ethyl group, more preferably a methyl group; It can be prepared by a first embodiment of the process according to the invention, which comprises:

[0011] The compound of general formula (I) I) providing a compound of general formula (I), [ka] During the ceremony, R 3 is a C1 to C8 alkyl group, preferably a C1 to C4 alkyl group, more preferably a tert-butyl group; R 4 is a linear or branched C1 to C5 alkyl group, preferably a methyl group; II) The compound provided in process step I) is reacted with at least one alkyl group R 2 with an alkylating agent comprising R 2 is a C1 to C8 alkyl group, preferably a methyl group or an ethyl group, more preferably a methyl group; III) The compound obtained in process step II) is reacted with alcohol R 1 -OH to form the residue R 4 Residue R 1 with a linear or branched C1-C24 alkyl group, preferably a methyl group or a C7-C9 alkyl group, more preferably a methyl group or a linear or branched C8 alkyl group, and most preferably a branched octyl group, with an isooctyl group or a 2-ethylhexyl group or both being most preferred. It can also be prepared by a second embodiment of the process according to the invention, which comprises:

[0012] According to a particularly preferred embodiment of the composition according to the invention, R 1is a C7-C9 alkyl group, more preferably a linear or branched C8 alkyl group, even more preferably a branched octyl group, and most preferably an isooctyl group or a 2-ethylhexyl group or both; R 2 is a methyl group, R 3 is a tert-butyl group.

[0013] Thus, a particularly preferred antioxidant is octyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate (=octyl 3-(3,5-di-tert-butyl-4-methoxyphenyl)propanoate), which preferably has one of the following structures: [ka]

[0014] Isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate can be prepared, for example, by catalytic O-methylation of isooctyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate using a methylating agent such as dimethyl carbonate, methyl iodide, methyl bromide, dimethyl sulfate, diazomethane, methanol, trimethylsulfonium salts or tetramethylammonium salts such as tetramethylammonium hydroxide or tetramethylammonium chloride. A process for the O-methylation of phenol or phenol derivatives using tetramethylammonium chloride as a methylating agent is disclosed, for example, by Panahi et al. in "Efficient and selective microwave-assisted O-methylation of phenolic compounds using tetramethylammonium hydroxide (TMAH)", Green Process Synth (Vol. 8, 2019), pp. 584-589. For example, isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate can be prepared by reacting isooctyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate with iodomethane in the presence of a basic compound such as KOH, or by first reacting methyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate with iodomethane in the presence of a basic compound such as KOH to give methyl 3-(3,5-di-tert-butyl-4-methoxyphenyl)propionate, and then reacting methyl 3-(3,5-di-tert-butyl-4-methoxyphenyl)propionate with isooctanol to give isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate in a transesterification reaction.

[0015] According to further preferred embodiments of the composition according to the invention, the composition comprises at least 0.1% by weight, or at least 1% by weight, or at least 5% by weight, or at least 10% by weight, or at least 20% by weight, or at least 30% by weight, or at least 40% by weight, or at least 50% by weight, or at least 60% by weight, or at least 70% by weight, or at least 80% by weight, or at least 90% by weight, or at least 95% by weight, or at least 99% by weight of a compound of general formula (I), preferably isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate, in each case based on the total weight of the composition. According to a particular embodiment of the composition according to the invention, the content of a compound of general formula (I), preferably isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate, in the composition is in the range of 0.1 to 99% by weight, more preferably in the range of 1 to 95% by weight, even more preferably in the range of 5 to 90% by weight, in each case based on the total weight of the composition.

[0016] According to a further particular embodiment of the composition according to the invention, said composition is obtained by supplementing a composition comprising isooctyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate with a particular amount of the corresponding O-alkylated derivative, i.e. a particular amount of isooctyl-3,5-di-tert-butyl-4-alkoxymethoxyhydrocinnamate, preferably isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate.

[0017] Thus, according to a particular embodiment of the composition of the present invention, the composition further comprises: ii) octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate, preferably isooctyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate, having one of the formulae of general structure (II): [ka] Includes.

[0018] In relation to this particular embodiment of the composition of the present invention, the composition comprises: i) at least 0.01% by weight, preferably at least 0.1% by weight, more preferably at least 1% by weight of a component of octyl-3,5-di-tert-butyl-4-methoxyhydrocinnamate, preferably isooctyl-3,5-di-tert-butyl-4-methoxyhydrocinnamate, it is also preferred that the amount of octyl-3,5-di-tert-butyl-4-methoxyhydrocinnamate is less than 35% by weight, preferably less than 25% by weight, more preferably less than 15% by weight, ii) a component of at least 25% by weight, preferably at least 45% by weight, more preferably at least 65% by weight of octyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate, preferably isooctyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate, wherein it is also preferred that the amount of octyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate is less than 99.99% by weight, preferably less than 99.9% by weight, more preferably less than 99% by weight. and in each case the above amounts are based on the total weight of components i) and ii) in the composition.

[0019] In relation to this particular embodiment of the composition of the present invention, the composition comprises: iii) less than 5% by weight, preferably less than 2.5% by weight, more preferably less than 1% by weight; dioctyl-α-(3,5-di-tert-butyl-4-hydroxybenzyl) glutarate, preferably dioctyl-α-(3,5-di-tert-butyl-4-hydroxybenzyl) glutarate having formula (III), in which R x and R y are each independently selected from the group consisting of an isooctyl group and a 2-ethylhexyl group, dioctyl-α-(3,5-di-tert-butyl-4-hydroxybenzyl)glutarate, most preferably diisooctyl-α-(3,5-di-tert-butyl-4-hydroxybenzyl)glutarate; [ka] Di-tert-butylphenol, Methyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate, Dimethyl-α-(3,5-di-tert-butyl-4-hydroxy-benzyl) glutarate, and an alcohol, preferably octanol, more preferably isooctanol and in each case the above amounts are based on the total weight of components i), ii) and iii) in the composition.

[0020] In connection with this particular embodiment of the composition according to the invention, it is further preferred that the composition comprises octyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate and dioctyl-α-(3,5-di-tert-butyl-4-hydroxybenzyl)glutarate, preferably isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate and diisooctyl-α-(3,5-di-tert-butyl-4-hydroxy-benzyl)glutarate, in a weight ratio of at least 2:1, preferably at least 3:1, more preferably at least 4:1, even more preferably at least 6:1, even more preferably at least 8:1, even more preferably at least 10:1, even more preferably at least 15:1 and most preferably at least 20:1.

[0021] In connection with this particular embodiment of the composition according to the invention, it is further preferred that the composition comprises from 1 to 50% by weight, preferably from 1.5 to 45% by weight, more preferably from 2 to 40% by weight, more preferably from 2.5 to 35% by weight, more preferably from 3 to 30% by weight, more preferably from 3.5 to 25% by weight and even more preferably from 4 to 20% by weight of a compound of general formula (I), preferably isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate, in each case based on the total weight of the composition.

[0022] It is further preferred in connection with this particular embodiment of the composition according to the invention that at least one of the following conditions (a1) to (a5), preferably all of the following conditions (a1) to (a5) are fulfilled: (a1) The composition has a viscosity of 60 to 300 cSt (6.0 × 10 -5 ~3.00×10 -4 m 2 / s), more preferably 80 to 250 cSt (8.0 × 10 -5 ~2.50×10 -4 m 2 / s, more preferably 100 to 200 cSt (1.00 × 10 -4 ~2.00×10 -4 m 2 / s) (measured at a temperature of 40° C. in accordance with ASTM D 445), (a2) the composition has a Gardner colour (measured according to ASTM D 1544) of less than 10 Gardner, preferably less than 5 Gardner, more preferably less than 3 Gardner; (a3) the composition has a moisture content (measured according to ASTM E 203) of less than 0.5% by weight, preferably less than 0.3% by weight, more preferably less than 0.1% by weight; (a4) the composition has a specific gravity (measured at a temperature of 25° C. according to ASTM D 1298) in the range of 0.900 to 1.020, preferably in the range of 0.925 to 1.010, more preferably in the range of 0.940 to 1.000; (a5) the composition has a total acid number (as determined by ASTM D664) of less than 5.0 mg KOH / g, preferably less than 2.5 mg KOH / g, and more preferably less than 1.0 mg KOH / g.

[0023] In a first variant of the composition according to the invention, the total amount of component i) in the composition (if the composition does not contain component ii)) or the total amount of components i) and ii) (if the composition contains component ii)) is in each case at least 95% by weight, preferably at least 97% by weight, more preferably at least 99% by weight, based on the total weight of the composition. The composition is therefore in the form of a separate additive that can be used to improve the oxidative stability of industrial products such as lubricants, lubricating compositions or polymer compositions.

[0024] In a second variant of the composition according to the invention, the composition is a lubricant or lubricating composition. With regard to this second variant of the composition according to the invention, it is particularly preferred that the composition is an additive blend. An "additive blend" (also called an "additive package") is a blend for the treatment of industrial and automotive lubricants, which comprises a combination of different additives, such as antioxidants, anti-wear additives, dispersants, ashless (metal-free) polymeric materials, detergents, antifoam additives, viscosity index improvers, copper passivators, rust inhibitors, pour point depressants, demulsifiers and friction modifiers. Thus, the composition according to the invention comprising the compound of general formula (I), preferably comprising isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate, may be in the form of such an additive package.

[0025] For this second variant of the composition according to the invention, it is further particularly preferred that the total amount of component i) in said composition (if the composition does not comprise component ii)) or the total amount of components i) and ii) (if the composition comprises component ii)) is in the range from 0.01 to 95% by weight, preferably in the range from 0.1 to 60% by weight and more preferably in the range from 0.5 to 30% by weight, in each case based on the total weight of the additive blend.

[0026] According to a third variant of the composition according to the invention, the composition is an engine oil comprising at least one base oil. With regard to this third variant of the composition according to the invention, it is particularly preferred that the total amount of component i) in the composition (if the composition does not comprise component ii)) or the total amount of components i) and ii) (if the composition comprises component ii)) is in each case in the range of 0.01 to 10% by weight, preferably in the range of 0.05 to 5% by weight, more preferably in the range of 0.1 to 2% by weight, based on the total weight of the engine oil.

[0027] According to a fourth variant of the composition according to the invention, the composition is a polymer composition comprising a polymer, preferably a thermoplastic polymer, a duroplastic (thermosetting) polymer, an elastomer, a polyol, a rubber, such as butadiene rubber (BR), styrene butadiene rubber (SBR), ethylene propylene rubber (EPR), nitrile butadiene rubber (NBR) or a mixture thereof, or a mixture comprising at least two of these polymers. With regard to the fourth variant of the composition according to the invention, it is particularly preferred that the total amount of component i) in the composition (if the composition does not comprise component ii)) or the total amount of components i) and ii) (if the composition comprises component ii)) is in each case in the range of 0.01 to 10% by weight, preferably in the range of 0.05 to 2.0% by weight, more preferably in the range of 0.1 to 1.0% by weight, based on the total weight of the polymer composition.

[0028] With regard to this fourth variant of the composition according to the invention, the thermoplastic polymer may be selected from the group consisting of low density polyethylene (LDPE), linear low density polyethylene (LLDPE), medium density polyethylene (MDPE), high density polyethylene (HDPE), homopolymers derived from monoethylenically and diethylenically unsaturated hydrocarbon monomers of C3 or higher, such as polypropylene, polyisobutylene, polymethylbutene-1, polymethylpentene-1, polybutene-1, polyisobutylene, etc.; copolymers derived from two or more monomers, such as ethylene-propylene copolymers, preferably at least predominantly propylene. More particularly preferred are selected from the group consisting of ethylene-propylene copolymers, propylene-butene-1 copolymers, propylene-isobutylene copolymers, etc., and blends thereof, polystyrenes, polyvinyl halides, and engineering thermoplastics such as polyamides, polyesters, polyphenylene oxides, polyphenylene sulfides, polyacetals, aliphatic polyketone copolymers or terpolymers, poly(ether sulfones), polycarbonates, liquid crystal polymers, poly(ether ether ketones), polyurethanes, and poly(arylates). The thermoplastic resin protected by the composition according to the invention is preferably polyurethane or polypropylene.

[0029] If the polymer to be stabilized by the composition according to the invention is a polyurethane, for example for the production of flexible or rigid foams, the composition according to the invention can be added to a polyol which subsequently reacts with an isocyanate to form a polyurethane.

[0030] The contribution to solving at least one of the objects according to the invention is also made by the use of a compound of general formula (I) as an additive in a lubricant of a lubricating composition, preferably an engine oil, or in a polymer composition, or both, [ka] During the ceremony, R 1is a linear or branched C1-C24 alkyl group, preferably a methyl group or a C7-C9 alkyl group, more preferably a methyl group or a linear or branched C8-alkyl group, most preferably a branched octyl group, most preferably an isooctyl group or a 2-ethylhexyl group or both, R 2 is a C1 to C8 alkyl group, preferably a methyl group or an ethyl group, more preferably a methyl group; R 3 is a C1 to C8 alkyl group, preferably a C1 to C4 alkyl group, more preferably a tert-butyl group; The compound of general formula (I) is preferably isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0031] Additives in the additive blend according to the present invention The additive blends (or additive packages) according to the invention are blends for the treatment of industrial and automotive lubricants, which in addition to base oils contain a combination of different additives such as antioxidants, anti-wear additives, dispersants, ashless (metal-free) polymeric materials, detergents, anti-foam additives, viscosity index improvers, copper passivators, rust inhibitors, pour point depressants, demulsifiers and friction modifiers. Thus, the composition comprising the compound of general formula (I), preferably the composition comprising isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate, may be part of such an additive package.

[0032] Suitable antioxidants in the additive blend that may be present in addition to the composition comprising the compound of general formula (I), preferably in addition to the composition comprising isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate, are: 1) Alkylated monophenols, such as 2,6-di-tert-butyl-4-methylphenol, 2-butyl-4,6-di-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(α-methyl-cyclohexyl)-4,6-dimethylphenol, 2,6-di-octadecyl 4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, linear or branched nonylphenols such as 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methyl-undec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methyltridec-1'-yl)-phenol or mixtures thereof, 2) Alkylthiomethylphenols, such as 2,4-di-octylthiomethyl-6-tert-butylphenol, 2,4-di-octylthiomethyl-6-methylphenol, 2,4-di-octylthiomethyl-6-ethylphenol or 2,6-di-dodecylthiomethyl-4-nonylphenol, 3) Hydroquinone and alkylated hydroquinones, such as 2,6-di-tert-butyl-4-methoxy-phenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butyl-hydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate or bis(3,5-di-tert-butyl-4-hydroxyphenyl)adipate, 4) Tocopherols, such as α-, β-, γ- or δ-tocopherol or mixtures thereof (vitamin E); 5) Hydroxylated thiodiphenyl ethers, such as 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis-(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol) or 4,4'-bis(2,6-di-methyl-4-hydroxyphenyl) disulfide, 6) Alkylidene bisphenols, such as 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis(4-methyl-6-(α-methyl-cyclohexyl)-phenol), 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylene-bis-(6-nonyl-4-methylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidene-bisphenols, bis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2'-methylenebis(6-(α-methylbenzyl)-4-nonylphenol), 2,2'-methylenebis(6-(α,α-dimethylbenzyl)-4-nonylphenol), 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-methylenebis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl) 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane, ethylene glycol bis(3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate), bis(3-tert-butyl-4-hydroxy-5-methylphenyl)dicyclopentadiene ene, bis(2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tert-butyl-4-methylphenyl)terephthalate, 1,1-bis(3,5-dimethyl-2-hydroxyphenyl)butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 2,2-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutane or 1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)-pentane, 7) O-, N- and S-benzyl compounds, such as 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxy-dibenzyl ether, octadecyl 4-hydroxy-3,5-dimethylbenzyl mercaptoacetate, tridecyl 4-hydroxy-3,5-di-tert-butylbenzyl mercaptoacetate, tris(3,5-di-tert-butyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxy-benzyl)sulfide or isooctyl 3,5-di-tert-butyl-4-hydroxy-benzyl mercaptoacetate, 8) Hydroxybenzylated malonates, such as dioctadecyl 2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate, dioctadecyl 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate, d-dodecyl mercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, or di(4-(1,1,3,3-tetramethylbutyl)phenyl)-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate; 9) Aromatic hydroxybenzyl compounds, such as 1,3,5-tris(3,5-di-tert-butyl-4-hydroxy-benzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene or 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol; 10) Triazine compounds, such as 2,4-bisoctylmercapto-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-triazine, Tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexahydro-1,3,5-triazine or 1,3,5-tris-(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate, 11) Benzylphosphonates, such as dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl 5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, or calcium salts of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid, 12) Acylaminophenols, such as 4-hydroxylauranilide, 4-hydroxystearanilide, or octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate; 13) Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, β-(5-tert-butyl)-4-hydroxy-3-methylphenyl)propionic acid, β-(3,5-dicyclohexyl-4-hydroxyphenyl)-propionic acid, 3,5-di-tert-butyl-4-hydroxyphenylacetic acid, or β-(5-tert-butyl)-4-hydroxyphenyl)-3-thiabutyric acid with monohydric or polyhydric alcohols, such as methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonyl alcohol, diols, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethyl-hexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo(2.2.2)octane, esters with glycerol or transesterification products based on natural triglycerides, for example of coconut oil, rapeseed oil, sunflower oil or rapeseed (colza) oil, 14) Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, such as N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine, or N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine, 15) Ascorbic acid (vitamin C), 16) Amine-type antioxidants, such as N,N'-diisopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N'-bis(1-ethyl-3-methyl-pentyl)-p-phenylenediamine, N,N'-bis(1-methyl-heptyl)-p-phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, Amines, N,N'-di-(naphth-2-yl)-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylene-diamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N-(1-methylheptyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4-(p-toluenesulfonamido)diphenylamine, N,N'-dimethyl-N,N'-di-sec-butyl-p-furan Phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxy-diphenylamine, N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamines such as p,p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-Octadecanoylaminophenol, Di-(4-Methoxyphenyl)-amine, 2,6-Di-tert-butyl-4-dimethylamino-methylphenol, 2,4'-Diamino-diphenylmethane, 4,4'-Diamino-diphenylmethane, N,N,N',N'-Tetramethyl-4,4'-Diamino-diphenylmethane, 1,2-Di-((2-methyl-phenyl)-amino)ethane, 1,2-Di-(phenylamino)propane, (o-Tolyl)biguanide, Di(4-(1',3'-Dimethyl-butyl)-phenyl)amine, tert-octylated N-phenyl-1-naphthylamine, mixtures of mono- and di-alkylated tert-butyl / tert-octyldiphenylamines, mixtures of mono- and di-alkylated nonyldiphenylamines, mixtures of mono- and di-alkylated dodecyldiphenylamines, mixtures of mono- and di-alkylated isopropyl / isohexyldiphenylamines, mixtures of mono- and di-alkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenanthroline, nothiazine, mixtures of mono- and di-alkylated tert-butyl / tert-octylphenothiazines, mixtures of mono- and di-alkylated tert-octyl-phenothiazines, N-allylphenothiazine, N,N,N',N"-tetraphenyl-1,4-diaminobut-2-ene, N,N-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine, bis-(2,2,6,6-tetramethylpiperidin-4-yl)sebacate, 2,2,6,6-tetramethylpiperidin-4-one, or 2,2,6,6-tetramethylpiperidin-4-ol, and 17) Aliphatic or aromatic phosphites, esters of thiodipropionic acid or thiodiacetic acid, or salts of dithiocarbamic acid or dithiophosphoric acid, 2,2,12,12-tetramethyl-5,9-dihydroxy-3,7,1-trithiatridecane, or 2,2,15,15-tetramethyl-5,12-dihydroxy-3,7,10,14-tetrathiahexadecane is selected from.

[0033] Suitable anti-wear additives include: 1) Dihydrocarbyl dithiophosphate metal salts in which the metal is aluminum, lead, tin, manganese, cobalt, nickel, zinc or copper, most often zinc; the zinc salts (zinc dialkyldithiophosphates) are [ka] wherein R and R' are independently selected from C1 to C20 Alkyl, C3-C 20 Alkenyl, C5-C 12 Cycloalkenyl, C7-C 13 Aralkyl or C6~C 10 aryl, for example, R and R' are independently C1-C 12 dihydrocarbyl dithiophosphate metal salts, 2) Sulfur- and / or phosphorus- and / or halogen-containing compounds, such as sulfurized olefins and vegetable oils, tritolyl phosphate, tricresyl phosphate, chlorinated paraffins, alkyl and aryl disulfides and alkyl and aryl trisulfides, amine salts of mono- and dialkyl phosphates, amine salts of methylphosphonic acid, diethanolaminomethyltolyltriazole, di(2-ethylhexyl)aminomethyltolyltriazole, derivatives of 2,5-dimercapto-1,3,4-thiadiazole, ethylenediamine ... tris((bisisopropyloxyphosphinothioyl)thio)propionate, triphenyl thiophosphate (triphenyl phosphorothioate), tris(alkylphenyl) phosphorothioates and mixtures thereof (e.g. tris(isononylphenyl) phosphorothioate), diphenyl monononylphenyl phosphorothioate, isobutylphenyl diphenyl phosphorothioate, dodecylamine salt of 3-hydroxy-1,3-thiaphosphetan-3-oxide, trithiophosphate 5,5,5-tris(isooctyl 2-acetate), derivatives of 2-mercaptobenzothiazole such as 1-(N,N-bis(2-ethylhexyl)aminomethyl)-2-mercapto-1H-1,3-benzothiazole or ethoxycarbonyl 5-octyldithiocarbamate is selected from.

[0034] Suitable dispersants are 1) Mannich bases, which are condensation reaction products of high molecular weight phenols, arylene polyamines, and aldehydes such as formaldehyde; 2) succinic acid-based dispersants which are reaction products of olefin polymers with succinic acylating agents (acids, anhydrides, esters or halides) which are further reacted with organic hydroxy compounds and / or amines; and 3) High molecular weight amides and esters, such as the reaction products of hydrocarbyl acylating agents with polyhydric aliphatic alcohols, such as glycerol, pentaerythritol or sorbitol. is selected from.

[0035] Ashless (metal-free) polymeric materials, which usually contain an oil-soluble high molecular weight backbone linked to polar functional groups that associate with the particles to be dispersed, are typically used as dispersants. Commonly used hydrocarbon backbone materials are olefin polymers and copolymers, i.e., ethylene, propylene, butylene, isobutylene, styrene, with or without additional functional groups incorporated into the polymer backbone. Polar materials such as amines, alcohols, amides, or esters are attached to the backbone via crosslinks.

[0036] Suitable detergents are selected from calcium, magnesium, barium, sodium or lithium salts of organic acids, such as sulfonic acids, alkyl phenols, sulfurized alkyl phenols, carboxylic acids, salicylic acids, phosphonic acids, thiophosphonic acids, and phosphinic acids. The salts may be neutral or overbased, for example by metal hydroxides or carbonates.

[0037] Suitable antifoam additives are selected from silicone oils, polysiloxanes, and polyethylene glycol ethers.

[0038] Suitable viscosity index improvers are selected from polyisobutylene, copolymers of ethylene and propylene, polyacrylates, polymethacrylates, vinylpyrrolidone / methacrylate copolymers, polyvinylpyrrolidone, polybutenes, olefin copolymers, styrene / acrylate copolymers, styrene / isoprene copolymers, styrene / isobutadiene copolymers, isoprene / butadiene copolymers and polyethers.

[0039] Suitable copper passivators are: 1) Benzotriazole and its derivatives, such as 4- or 5-alkylbenzotriazoles (e.g. tolutriazole) and its derivatives, 4,5,6,7-tetrahydrobenzotriazole, 5,5'-methylenebisbenzotriazole, Mannich bases of benzotriazole or tolutriazole, such as 1-(di(2-ethylhexyl)aminomethyl)tolutriazole and 1-(di-(2-ethylhexyl)aminomethyl)-benzotriazole, alkoxyalkylbenzotriazoles, such as 1-(nonyloxymethyl)-benzotriazole, 1-(1-butoxyethyl)-benzotriazole, or 1-(1-cyclohexyloxybutyl)-tolutriazole; 2) Imidazole derivatives, such as 4,4'-methylenebis(2-undecyl-5-methyl-imidazole), bis((N-methyl)imidazol-2-yl)carbinol octyl ether, 3) Sulfur-containing heterocyclic compounds, such as 2-mercaptobenzothiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercaptobenzothiadiazole and their derivatives, or 3,5-bis(di(2-ethylhexyl)aminomethyl)-1,3,4-thiadiazolin-2-one, and 4) Amino compounds, such as salicylidene propylene diamine, salicylamino guanidine or salts thereof is selected from.

[0040] Suitable rust inhibitors are: 1) nonionic polyoxyalkylene polyols and esters thereof, polyoxyalkylene phenols, organic acids, esters thereof, metal salts, amine salts and anhydrides thereof, such as alkyl and alkenyl succinic acids and their partial esters with alcohols, diols or hydroxycarboxylic acids, partial amides of alkyl and alkenyl succinic acids, 4-nonylphenoxyacetic acid, alkoxyethoxy and alkoxyethoxycarboxylic acids, such as dodecyloxyacetic acid, dodecyloxy(ethoxy)acetic acid and their amine salts, or N-oleoyl sarcosine, sorbitan monooleate, lead naphthenate and alkenyl succinic anhydrides, such as dodecenyl succinic anhydride, 2-(2-carboxyethyl)-1-dodecyl-3-methyl glycerol and its salts, such as the sodium and triethanolamine salts; 2) i) nitrogen-containing compounds selected from primary, secondary or tertiary aliphatic or primary, secondary or tertiary cycloaliphatic amines and amine salts of organic and inorganic acids, such as oil-soluble alkylammonium carboxylates, and also 1-(N,N-bis(2-hydroxyethyl)amino)-3-(4-nonylphenoxy)propan-2-ol, or ii) heterocyclic compounds, such as substituted imidazolines or oxazolines, for example 2-heptadecenyl-1-(2-hydroxyethyl)-imidazoline, 3) phosphorus-containing compounds, such as amine salts of phosphoric acid, phosphoric acid partial esters or phosphonic acid partial esters, or zinc dialkyldithiophosphates; 4) Sulfur-containing compounds, such as barium dinonylnaphthalene-sulfonate, calcium petroleum sulfonate, alkylthio-substituted aliphatic carboxylic acids, esters of aliphatic 2-sulfocarboxylic acids, or salts thereof; 5) Glycerol derivatives, such as glycerol monooleate, 1-(alkylphenoxy)-3-(2-hydroxyethyl)glycerol, 1-(alkylphenoxy)-3-(2,3-dihydroxypropyl)glycerol, or 2-carboxyalkyl-1,3-dialkylglycerol. is selected from.

[0041] Suitable pour point depressants are selected from polymethacrylates and alkylated naphthalene derivatives.

[0042] Suitable demulsifiers are selected from polyether polyols and dinonyl naphthalene sulfonates.

[0043] Suitable friction modifiers are selected from fatty acids and their derivatives, e.g., natural esters of fatty acids such as glycerol monooleate, amides, imides and amines, e.g., oleylamine, sulfur-containing organomolybdenum dithiocarbamates, sulfur-phosphorus-containing organomolybdenum dithiophosphates, sulfur-nitrogen-containing organomolybdenum compounds based dispersants, molybdenum carboxylates, molybdenum-amine complexes, molybdenum amine / alcohol / amide complexes, and molybdenum cluster compounds, Teflon® and molybdenum disulfide.

[0044] Base oil in the lubricant according to the present invention A lubricant, preferably an engine oil, according to the present invention comprises at least one base oil (i.e. a lubricant of lubricating viscosity) and a composition comprising a compound of general formula (I) according to the present invention, preferably a composition comprising isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate.

[0045] Suitable base oils are mineral and synthetic base oils selected from Groups I to V. These base oils are broadly specified in the American Petroleum Institute (API) Base Oil Interchangeability Guidelines.

[0046] The base oil may be, for example, oils and greases based on mineral oils or vegetable and animal oils, fats, tallows and waxes or mixtures thereof.Vegetable and animal oils, fats, tallows and waxes are, for example, palm kernel oil, palm oil, olive oil, colza oil, rapeseed oil, linseed oil, soybean oil, cottonseed oil, sunflower oil, coconut oil, corn oil, castor oil, walnut oil and mixtures thereof, fish oils, and chemically modified, for example epoxidized or sulfoxidized, or genetically engineered, for example genetically engineered soybean oil.

[0047] Examples of synthetic base oils include lubricants based on aliphatic or aromatic carboxylic acid esters, polymeric esters, polyalkylene oxides, phosphate esters, poly-α-olefins, silicones, alkylated benzenes, alkylated naphthalenes, or diesters of dibasic acids and monohydric alcohols, such as dioctyl sebacate or dinonyl adipate, triesters of trimethylolpropane and monobasic acids or mixtures of such acids, such as trimethylolpropane tripelargonate, trimethylolpropane tricaprylate, or mixtures thereof, tetraesters of pentaerythritol and monobasic acids or mixtures of such acids, such as pentaerythrityl tetracaprylate, or complex esters of monobasic and dibasic acids and polyhydric alcohols, such as complex esters of trimethylolpropane with caprylic acid and sebacic acid, or mixtures thereof. Particularly suitable in addition to mineral oils are, for example, poly-α-olefins, ester-based lubricants, phosphate esters, glycols, polyglycols, and polyalkylene glycols, and mixtures thereof with water.

[0048] When other additives are used in addition to the composition comprising the compound of general formula (I) according to the present invention, preferably in addition to the composition comprising isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate, it may be desirable, but not necessary, to prepare an additive concentrate in the form of the above-mentioned additive blend (or additive package) comprising a concentrated solution or dispersion of the composition comprising the compound of general formula (I) according to the present invention and one or more of the above-mentioned other additives, preferably a concentrated solution or dispersion of isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate and one or more of the above-mentioned other additives, by which several additives can be added simultaneously to a base oil to form a lubricating oil composition. The dissolution of the additive concentrate in the lubricating oil can be promoted by a solvent and by mixing accompanied by gentle heating, but this action is not essential. The concentrate or additive blend is typically formulated to contain the appropriate amount of additive to provide the desired concentration in the final formulation when the additive blend is combined with a given amount of base oil. Thus, the composition containing the compound of general formula (I) according to the present invention can be added to a small amount of base oil or other compatible solvent together with other desired additives to form an additive blend containing an appropriate proportion of active ingredient, typically in a total amount of about 2.5 to about 90% by weight, preferably about 15 to about 75% by weight, more preferably about 25 to about 60% by weight of additive, the remainder being base oil. The final formulation can typically use about 1 to 20% by weight of the additive blend, the remainder being base oil.

[0049] Polymers in the polymer composition according to the present invention The polymer composition according to the present invention comprises a composition comprising a compound of general formula (I) according to the present invention, preferably a composition comprising isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate, as well as a polymer, preferably a thermoplastic polymer, a duroplastic polymer, an elastomer, a polyol, a rubber, such as butadiene rubber (BR), styrene butadiene rubber (SBR), ethylene propylene rubber (EPR), nitrile butadiene rubber (NBR) or a mixture thereof, or a mixture comprising at least two of these polymers.

[0050] Thermoplastic polymers that can be stabilized against oxidative degradation using the compositions containing the compounds of general formula (I) according to the invention include low density polyethylene (LDPE), linear low density polyethylene (LLDPE), medium density polyethylene (MDPE), high density polyethylene (HDPE), or polyethylene having a density of 0.85 to 1.4 gm / cm 3 Resins derived from ethylene, including other ethylene-derived resins having a density of 0.1 to 0.5; homopolymers derived from monoethylenically and diethylenically unsaturated hydrocarbon monomers of C3 or higher, such as polypropylene, polyisobutylene, polymethylbutene-1, polymethylpentene-1, polybutene-1, polyisobutylene, etc.; copolymers derived from two or more monomers, such as ethylene-propylene copolymers, preferably at least predominantly propylene, propylene-butene-1 copolymers, propylene-isobutylene copolymers, etc., and blends thereof, polystyrene; polyvinyl halides; and engineering thermoplastics, such as polyamides, polyesters, polyphenylene oxides, polyphenylene sulfides, polyacetals, aliphatic polyketone copolymers or terpolymers, poly(ether sulfones), polycarbonates, liquid crystal polymers, poly(ether ether ketones), polyurethanes, and poly(arylates). The thermoplastic resin protected by the composition of the present invention is preferably polyurethane or polypropylene.

[0051] The invention will now be described in more detail by reference to test methods and non-limiting examples. EXAMPLES

[0052] Test Method Determination of oxidative stability The oxidative stability was evaluated using a pressurized differential scanning calorimetry (PDSC) instrument.

[0053] PDSC examines the oxidative stability of oils under thin film oxidation conditions. In an isothermal mode where the PDSC temperature is maintained at a given value, the oxidative stability of the test oils is ranked according to their Oxidative Induction Time (OIT), which corresponds to the exothermic release of heat caused by the onset of oil oxidation. Oils that give a longer OIT are generally considered to be more resistant to oxidation. Each blend was tested in duplicate using the following instrument conditions and the average OIT was determined. The PDSC test temperature was 180°C.

[0054] The following measurement conditions were selected: Temperature gradient: 40℃ / min Pressure: 500 psi (approx. 3.45 MPa) O2 flow rate: 100ml / min Sample size: approx. 1.5 mg Pan: Aluminum, open

[0055] Working Example Synthesis Example 1 [ka] 3,5-Bis(1,1-dimethylethyl)-4-hydroxy-benzenepropanoic acid-C7-9-branched alkyl ester, KOH and iodomethane were stirred in acetone at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and H2O. The aqueous phase was extracted three times with ethyl acetate and the organics were combined, dried (MgSO4) and concentrated in vacuo. The product was obtained by distillation of the crude product.

[0056] Synthesis Example 2 [ka] Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, KOH, and iodomethane were stirred in acetone at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and H2O. The aqueous phase was extracted three times with ethyl acetate and the organics were combined, dried (MgSO4), and concentrated in vacuo to give a composition containing methyl 3-(3,5-di-tert-butyl-4-methoxyphenyl)propionate.

[0057] Methyl 3-(3,5-di-tert-butyl-4-methoxyphenyl)propionate, isooctanol and aluminum were stirred at 190° C. for 18 hours. The reaction mixture was concentrated in vacuum. The product was obtained by distilling the crude product.

[0058] Example 1 The isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate prepared in Synthesis Example 1 above was used in the form of a mixture with SONGNOX® L135 (an antioxidant based on isooctyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate) (Compositions A, B, C and D).

[0059] [Table 1]

[0060] Using the above composition, a test oil was prepared to investigate the antioxidant properties of the above composition. For this purpose, 0.5 wt. % of the composition was added to a 50:50 mixture of Yubase 4 and Yubase 6 (Group III oil mixture) obtained from SK Lubricants Co. Ltd., Seoul, Korea. From the lubricants thus obtained, the oxidation stability was determined by PDSC (performed at 180°C according to ASTM D6186). The following results were obtained:

[0061] [Table 2]

[0062] As can be seen from the results shown in Table 1, O-alkylated highly sterically hindered compounds such as isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate are particularly effective antioxidants compared to their corresponding phenolic derivatives.

Claims

1. i) A compound of general formula (I), 【Chemical 1】 During the ceremony, R １ is a linear or branched C1 to C24 alkyl group, R ２ is a C1 to C8 alkyl group, R ３ is a C1-C8 alkyl group A composition comprising a compound.

2. R １ is a C7-C9-alkyl group, preferably an isooctyl group or a 2-ethylhexyl group or both, R ２ is a methyl group, R ３ is a tert-butyl group The composition of claim 1.

3. 3. The composition of claim 1 or claim 2, wherein the composition comprises at least 0.1% by weight of the compound of general formula (I) based on the total weight of the composition.

4. 4. The composition of claim 3, wherein the composition comprises at least 50% by weight of the compound of general formula (I) based on the total weight of the composition.

5. 5. The composition of claim 4, wherein the composition comprises at least 90% by weight of the compound of general formula (I) based on the total weight of the composition.

6. ii) Isooctyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate The composition of claim 2 further comprising:

7. The composition comprises: i) at least 0.01% by weight of isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate; ii) at least 25% by weight of isooctyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate 7. The composition of claim 6, comprising:

8. The composition comprises: iii) less than 5% by weight of a compound selected from the group consisting of diisooctyl-α-(3,5-di-tert-butyl-4-hydroxybenzyl)glutarate, di-tert-butylphenol, methyl-3,5-di-tert-butyl-4-hydroxyhydrocinnamate, and isooctanol 8. The composition of claim 7, comprising:

9. 9. The composition of claim 8, wherein the composition comprises isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate and diisooctyl-α-(3,5-di-tert-butyl-4-hydroxybenzyl) glutarate in a weight ratio of at least 2:

1.

10. The composition according to claim 6 or 7, wherein the composition comprises 1 to 50% by weight of the compound of general formula (I) based on the total weight of the composition.

11. The composition according to claim 10, wherein the composition comprises 2.5 to 35% by weight of the compound of general formula (I) based on the total weight of the composition.

12. The following conditions (a1) to (a5): (a1) The composition has a viscosity of 60 to 300 cSt (6.0 × 10 －５ ~3.00 x 10 －４ m ２ / s) (measured at a temperature of 40°C according to ASTM D 445), (a2) the composition has a Gardner color number (measured in accordance with ASTM D 1544) of less than 10 Gardner; (a3) the composition has a moisture content of less than 0.5 wt. % (measured in accordance with ASTM E 203); (a4) the composition has a specific gravity in the range of 0.900 to 1.020 (measured at a temperature of 25°C according to ASTM D 1298); (a5) the composition has a total acid number (as determined by ASTM D664) of less than 5.0 mg KOH / g The composition according to claim 6 or claim 7, wherein at least one of the following is satisfied:

13. 7. The composition of claim 1, claim 2 or claim 6, wherein the total amount of component i) or the total amount of components i) and ii) in the composition is at least 95 wt. %, based on the total weight of the composition.

14. The composition of claim 1, claim 2 or claim 6, wherein the composition is an additive blend.

15. 15. The composition of claim 14, wherein the total amount of component i) or the total amount of components i) and ii) in the composition is in the range of 0.01 to 50 wt. %, based on the total weight of the additive blend.

16. The composition of claim 1, claim 2 or claim 6, wherein the composition is an engine oil comprising at least one base oil.

17. 17. The composition of claim 16, wherein the total amount of component i) or the total amount of components i) and ii) in the composition is in the range of 0.01 to 5 wt. %, based on the total weight of the engine oil.

18. The composition according to claim 1, claim 2 or claim 6, wherein the composition is a polymer composition comprising a polymer.

19. 19. The composition of claim 18, wherein the total amount of component i) or the total amount of components i) and ii) in the composition is in the range of 0.01 to 5 wt. %, based on the total weight of the polymer composition.

20. 3. Use of a composition according to claim 1 or claim 2 as an additive in an additive blend, engine oil or polymer composition.

21. Use of a compound of general formula (I) as an additive in an additive blend, engine oil or polymer composition, 【Chemistry 2】 During the ceremony, R １ is a linear or branched C1 to C24 alkyl group, R ２ is a C1 to C8 alkyl group, R ３ is a C1-C8 alkyl group use.

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