Phenolic compound, stabilizer, organic material composition, and method for stabilizing organic material

Abstract

Provided is a phenolic compound represented by formula (I). In formula (I), R1|and R2 each independently represent a hydrogen atom, a C1-C8 alkyl group, or a C5-C8 cycloalkyl group, X represents a C1-C3, linear or branched alkylene group, Y represents *-C(=O)-O-**, *-O-C(=O)-**, *-O-**, or *-O-C(=O)-O-** (* indicates a bond with the X and ** indicates a bond with the Z), and Z represents a group (z1) represented by formula (z1) or a C9-C24, branched, (un)saturated hydrocarbon group (z2), with the proviso that when Y represents *-C(=O)-O-**, the hydrocarbon group (z2) is a group represented by formula (z2'). In formula (z1), A represents a C1-C20, linear or branched alkylene group, with the proviso that when Y represents *-C(=O)-O-**, the number of carbon atoms of the alkylene group is 4-20, B represents a C2 or C3, linear or branched alkylene group, n indicates an integer of 0-5, R3 represents a C1-C20, linear or branched alkyl group, and *** indicates a bond with the Y. In formula (z2'), m indicates an integer of 1-3, D represents -CH2-CH2-CH(-CH3)-, -CH2-CH=C(-CH3)-, -CH2-CH(-CH3)-, or -CH=C(-CH3)-, and *** indicates a bond with the Y.

Description

Phenolic compound, stabilizer, organic material composition, and method for stabilizing organic material

[0001] The present invention relates to a phenolic compound, a stabilizer, an organic material composition, and a method for stabilizing an organic material.

[0002] Resin compositions containing polyolefin resins, particularly polyethylene-based resins and / or polypropylene-based resins, are used, for example, as materials for various industrial parts such as bumpers, instrument panels, door trims, pillars, and other interior and exterior parts in automotive applications, parts for vacuum cleaners, televisions, and the like in home appliance applications, various housing equipment parts, various industrial parts, and various building material parts, or as a wide variety of films such as heavy-duty bags, shrink wrap, general packaging, thin films, protective films (protective films), extrusion laminated films, extrusion-molded films, and foam-molded films. During the production, processing, and use of these parts, the resin compositions constituting the parts deteriorate due to the action of heat, oxygen, and the like, resulting in a decrease in the strength properties of the organic material due to phenomena such as molecular scission and molecular crosslinking, changes in flowability, coloration, and deterioration in surface properties, which can significantly impair the commercial value.

[0003] In order to prevent deterioration of such resin compositions due to the action of heat, oxygen, and the like, phenolic compounds have been added, and various phenolic compounds have been investigated (Patent Documents 1 to 3).

[0004] JP 2013-540195 specification U.S. Pat. No. 4,032,562 specification

[0005] In order to feed a phenolic compound stably into a resin, it is preferable to add it in a liquid state, but when a solid compound has a melting point of 30° C. or higher, for example, adding the phenolic compound in a liquid state may require an operation of heating and melting the phenolic compound itself. Also, when the phenolic compound is added after being mixed with other additives, the additive mixture may become non-uniform, making it difficult to mix the additive uniformly into the resin.

[0006] Therefore, an object of the present invention is to provide a phenolic compound that can be added to a resin without heating the phenolic compound itself and that is easy to handle.

[0007] In order to solve the above problems, the present inventors have conducted extensive research focusing on the types and amounts of components contained in a resin composition, and as a result have found that the above problems can be solved by using a polyolefin resin composition containing specific components, thereby completing the present invention.

[0008] That is, the present invention includes the following preferred embodiments: [1] Formula (I): [In formula (I), R １ and R ２ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a cycloalkyl group having 5 to 8 carbon atoms, X represents a linear or branched alkylene group having 1 to 3 carbon atoms, Y represents *-C(=O)-O-**, *-O-C(=O)-**, *-O-**, or *-O-C(=O)-O-**, * represents a bond to X, and ** represents a bond to Z, and Z is represented by formula (z1): [In formula (z1), A represents a linear or branched alkylene group having 1 to 20 carbon atoms, provided that when Y represents *-C(=O)-O-**, the alkylene group has 4 to 20 carbon atoms, B represents a linear or branched alkylene group having 2 to 3 carbon atoms, n represents an integer of 0 to 5, and R ３ represents a linear or branched alkyl group having 1 to 20 carbon atoms, and *** represents a bond to Y, or a branched, saturated or unsaturated hydrocarbon group (z2) having 9 to 24 carbon atoms, provided that when Y represents *-C(=O)-O-**, the hydrocarbon group (z2) is represented by the formula (z2'): [In formula (z2'), m represents an integer of 1 to 3, and D represents -CH ２ -CH ２ -CH(-CH ３ ) -, -CH ２ -CH=C(-CH ３ ) -, -CH ２ -CH(-CH ３ ) - or -CH=C(-CH ３)-, and *** represents a bond to Y. [2] The phenolic compound according to [1], wherein Y in formula (I) represents *-C(═O)-O-** or *-O-C(═O)-**, and Z is a group represented by formula (z1). [3] The phenolic compound according to [1], wherein Y in formula (I) represents *-O-C(═O)-**, and Z represents a branched, saturated or unsaturated hydrocarbon group having 9 to 24 carbon atoms. [4] The phenolic compound according to [1], wherein Y in formula (I) represents *-C(═O)-O-**, and Z is a group represented by formula (z2'). [5] A stabilizer comprising the phenolic compound according to any one of [1] to [4]. [6] The stabilizer according to [5], which is an antioxidant, an antiaging agent, and / or a processing stabilizer. [7] An organic material composition comprising the phenolic compound according to any one of [1] to [4] and at least one organic material. [8] The organic material composition according to [7], wherein the organic material is a thermoplastic resin. [9] The organic material composition according to [8], wherein the thermoplastic resin is a polyolefin or an engineering plastic.

[10] A method for stabilizing an organic material, comprising adding the phenolic compound according to any one of [1] to [4] or the stabilizer according to [5] or [6] to an organic material.

[11] The stabilization method according to

[10] , wherein the organic material is a thermoplastic resin.

[12] The stabilization method according to

[11] , wherein the thermoplastic resin is a polyolefin or an engineering plastic.

[0009] According to the present invention, it is possible to provide a phenolic compound that can be added to a resin without heating the phenolic compound itself and that is easy to handle.

[0010] Hereinafter, embodiments of the present invention will be described in detail. Note that the scope of the present invention is not limited to the embodiments described herein, and various modifications can be made without departing from the spirit of the present invention. Furthermore, when multiple upper and lower limit values ​​are described for a specific feature, any of these upper and lower limit values ​​can be combined to form a suitable numerical range.

[0011] The present invention relates to a phenolic compound of formula (I): [In formula (I), R １ and R ２ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a cycloalkyl group having 5 to 8 carbon atoms, X represents a linear or branched alkylene group having 1 to 3 carbon atoms, Y represents *-C(=O)-O-**, *-O-C(=O)-**, *-O-**, or *-O-C(=O)-O-**, * represents a bond to X, and ** represents a bond to Z, and Z is represented by formula (z1): [In formula (z1), A represents a linear or branched alkylene group having 1 to 20 carbon atoms, provided that when Y represents *-C(=O)-O-**, the alkylene group has 4 to 20 carbon atoms, B represents a linear or branched alkylene group having 2 to 3 carbon atoms, n represents an integer of 0 to 5, and R ３ represents a linear or branched alkyl group having 1 to 20 carbon atoms, and *** represents a bond to Y, or a branched, saturated or unsaturated hydrocarbon group (z2) having 9 to 24 carbon atoms, provided that when Y represents *-C(=O)-O-**, the hydrocarbon group (z2) is represented by the formula (z2'): [In formula (z2'), m represents an integer of 1 to 3, and D represents -CH ２ -CH ２ -CH(-CH ３ ) -, -CH ２ -CH=C(-CH ３ ) -, -CH ２ -CH(-CH ３ ) - or -CH=C(-CH ３ )-, and *** represents a bond to Y.

[0012] In formula (I), R １ and R ２ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a cycloalkyl group having 5 to 8 carbon atoms.

[0013] Examples of alkyl groups having 1 to 8 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-pentyl, t-pentyl, 2-methylbutyl, 3-methylbutyl, 2-ethylpropyl, n-hexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, 1,1,3,3-tetramethylbutyl, and 2-ethylhexyl. From the viewpoint of easily improving heat resistance and antioxidant performance, the number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 5, and even more preferably 1 to 4.

[0014] Examples of the cycloalkyl group having 5 to 8 carbon atoms include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. From the viewpoint of easily improving antioxidant performance, the number of carbon atoms in the cycloalkyl group is preferably 5 to 8, more preferably 5 to 7, and even more preferably 5 to 6.

[0015] In formula (I), X represents a linear or branched alkylene group having 1 to 3 carbon atoms, Y represents *-C(=O)-O-**, *-O-C(=O)-**, *-O-**, or *-O-C(=O)-O-**, * represents a bond to X, and ** represents a bond to Z.

[0016] Examples of linear or branched alkylene groups having 1 to 3 carbon atoms include methylene, ethylene, methylmethylene, propylene, and isopropylene. The alkylene group is preferably a linear alkylene group having 1 to 3 carbon atoms. The number of carbon atoms in the alkylene group is preferably 2 to 3. Y preferably represents *-C(=O)-O-** or *-O-C(=O)-**.

[0017] Z in formula (I) is a group represented by formula (z1): [In formula (z1), A represents a linear or branched alkylene group having 1 to 20 carbon atoms, provided that when Y represents *-C(=O)-O-**, the alkylene group has 4 to 20 carbon atoms, B represents a linear or branched alkylene group having 2 to 3 carbon atoms, n represents an integer of 0 to 5, and R ３represents a linear or branched alkyl group having 1 to 20 carbon atoms, and *** represents a bond to Y, or a branched, saturated or unsaturated hydrocarbon group (z2) having 9 to 24 carbon atoms, provided that when Y represents *-C(=O)-O-**, the hydrocarbon group (z2) is represented by the formula (z2'): [In formula (z2'), m represents an integer of 1 to 3, and D represents -CH ２ -CH ２ -CH(-CH ３ ) -, -CH ２ -CH=C(-CH ３ ) -, -CH ２ -CH(-CH ３ ) - or -CH=C(-CH ３ )-, and *** represents a bond to Y.

[0018] Z is formula (z1): In the case where the formula (z1) represents a group (z1) represented by the formula (z1), A represents a linear or branched alkylene group having 1 to 20 carbon atoms, provided that when Y represents *-C(=O)-O-**, the alkylene group has 4 to 20 carbon atoms, B represents a linear or branched alkylene group having 2 to 3 carbon atoms, n represents an integer of 0 to 5, and R ３ represents a linear or branched alkyl group having 1 to 20 carbon atoms, and *** represents a bond to Y.

[0019] Examples of the linear or branched alkylene group having 1 to 20 carbon atoms for A include a methylene group, an ethylene group, a propylene group, a methylethylene group, a butylene group, a 1-methylpropylene group, a 2-methylpropylene group, a 1,2-dimethylpropylene group, a 1,3-dimethylpropylene group, a 1-methylbutylene group, a 2-methylbutylene group, a 3-methylbutylene group, a 4-methylbutylene group, a 2,4-dimethylbutylene group, a 1,3-dimethylbutylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a nonylene group, a decylene group, an undecylene group, a dodecylene group, a tridecylene group, a tetradecylene group, a pentadecylene group, a hexadecylene group, a heptadecylene group, an octadecylene group, a nonadecylene group, and an icosylene group. The number of carbon atoms in the alkylene group is preferably 2 to 20, more preferably 5 to 15, and even more preferably 5 to 10. From the viewpoint of improving the handleability of the phenolic compound, the linear or branched alkylene group having 1 to 20 carbon atoms in A is preferably a linear alkylene group having 1 to 20 carbon atoms, more preferably a linear alkylene group having 5 to 15 carbon atoms, and even more preferably a linear alkylene group having 5 to 10 carbon atoms.

[0020] B represents a linear or branched alkylene group having 2 to 3 carbon atoms. Examples of the linear or branched alkylene group having 2 to 3 carbon atoms include an ethylene group, an n-propylene group, and an isopropylene group. From the viewpoint of raw material availability, the alkylene group is preferably an ethylene group or an isopropylene group.

[0021] n represents an integer of 0 to 5. From the viewpoint of the stability of the phenolic compound in the organic material composition and suppression of bleeding, n is preferably 0 to 4, more preferably 0 to 3, even more preferably 0 to 2, and still more preferably 0 to 1.

[0022] R ３In the formula (I), examples of the linear or branched alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a t-butyl group, an n-pentyl group, a t-pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 2-ethylpropyl group, an n-hexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, a 2-ethylhexyl group, a 2,4-dimethylbutyl group, a 1,3-dimethylbutyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an icosyl group. From the viewpoint of improving antioxidant performance, the number of carbon atoms in the alkyl group is preferably 3 to 20, more preferably 5 to 20, and even more preferably 5 to 15. ３ In terms of improving the handleability of the phenolic compound, the linear or branched alkyl group having 1 to 20 carbon atoms is preferably a linear alkyl group having 1 to 20 carbon atoms, more preferably a linear alkyl group having 5 to 20 carbon atoms, and even more preferably a linear alkyl group having 5 to 15 carbon atoms.

[0023] Specific examples of the group (z1) represented by formula (z1) include groups represented by the following formulae (z-1-1) to (z-1-5).

[0024]

[0025] When Z represents a branched, saturated or unsaturated hydrocarbon group (z2) having 9 to 24 carbon atoms, the branched, saturated or unsaturated hydrocarbon group having 9 to 24 carbon atoms may be a hydrocarbon group having a main chain and at least one branch chain, such as Guerbet alcohol. From the viewpoint of achieving both ease of handling of the phenolic compound and antioxidant performance, the branched, saturated or unsaturated hydrocarbon group having 9 to 24 carbon atoms is preferably a hydrocarbon group having at least a saturated or unsaturated main chain having preferably 6 to 12 carbon atoms and at least one saturated or unsaturated branch chain having preferably 1 to 10 carbon atoms. In this case, the main chain preferably has 8 to 14 carbon atoms, more preferably 9 to 14 carbon atoms, and even more preferably 10 to 14 carbon atoms, and the at least one branch chain preferably has 1 to 10 carbon atoms, more preferably 3 to 10 carbon atoms, and even more preferably 6 to 10 carbon atoms. The hydrocarbon group may have a main chain and one branch chain, or a main chain and two or more branch chains. The number of carbon atoms in the main chain and the branched chains may be the same or different.

[0026] Examples of the branched saturated or unsaturated hydrocarbon group (z2) having 9 to 24 carbon atoms include: (z2-a): a hydrocarbon group represented by formula (z2-a): [In formula (z2-a), R ４ and R ５ each independently represent a linear or branched alkyl group having 5 to 22 carbon atoms, more preferably a linear or branched alkyl group having 5 to 12 carbon atoms, and *** represents a bond to Y] (z2-b): a group in which at least two hydrogen atoms of a linear alkyl group having 8 to 16 carbon atoms have been substituted with an alkyl group having 1 to 3 carbon atoms (preferably an alkyl group having 1 or 2 carbon atoms, more preferably a methyl group).

[0027] Specific examples of the hydrocarbon group (z2) having 9 to 24 carbon atoms include groups represented by the following formulas (2-1) to (2-7).

[0028]

[0029] In the compound represented by formula (I), when Y represents *-C(=O)-O-**, the hydrocarbon group (z2) is represented by formula (z2'): [In formula (z2'), m represents an integer of 1 to 3, and D represents -CH ２ -CH ２ -CH(-CH ３ ) -, -CH ２ -CH=C(-CH ３ ) -, -CH ２ -CH(-CH ３ ) - or -CH=C(-CH ３ )-, and *** represents a bond to Y. Even when Y represents a group other than *-C(═O)-O-**, the hydrocarbon group (z2) may be a group represented by formula (z2′).

[0030] In a preferred embodiment of the present invention, Y in formula (I) represents *-C(=O)-O-** or *-O-C(=O)-**, and Z is a group represented by formula (z1). Examples of such phenolic compounds include compounds represented by the following formulae (I-1) to (I-6).

[0031]

[0032] In another preferred embodiment of the present invention, Y in formula (I) represents *-O-C(=O)-**, and Z represents a branched, saturated or unsaturated hydrocarbon group having 9 to 24 carbon atoms. Examples of such phenolic compounds include compounds represented by the following formulae (I-7) to (I-10).

[0033]

[0034] In another preferred embodiment of the present invention, Y in formula (I) represents *-C(=O)-O-**, and Z is a group represented by formula (z2'). Examples of such phenolic compounds include compounds represented by the following formulae (I-11) to (I-15).

[0035]

[0036] The phenolic compound represented by formula (I) is preferably liquid at 30°C, and as a result, it is easy to handle when added to an organic material and can be stably incorporated into an organic material composition. From the viewpoint of ease of handling when added to an organic material composition, the melting point of the phenolic compound represented by formula (I) is preferably 30°C or lower, more preferably 20°C or lower. In a preferred embodiment, the melting point of the phenolic compound represented by formula (I) is preferably -80 to 30°C, more preferably -80 to 25°C, and even more preferably -80 to 20°C.

[0037] Method for Producing Phenolic Compounds There are no particular limitations on the method for producing the phenolic compound represented by formula (I) of the present invention. However, when Y is *-C(=O)-O-** or *-O-C(=O)-**, the compound can be synthesized by reacting a carboxylic acid and / or a derivative thereof with an alcohol. Examples of carboxylic acid derivatives include alkyl esters such as methyl carboxylic acid ester and ethyl carboxylic acid ester, and carboxylic acid halides. When Y is *-O-**, the compound can be synthesized by reacting an alkylating agent such as an alcohol, alkyl halide, or alkyl tosylate with an alcohol. When Y is *-O-C(=O)-O-**, the compound can be synthesized by reacting a carbonate ester such as alkyl carbonate or phenyl carbonate with an alcohol.

[0038] The reaction may be carried out in an organic solvent or without using an organic solvent. The organic solvent is not particularly limited as long as it does not inhibit the reaction, and examples thereof include ether solvents, aromatic hydrocarbon solvents, aliphatic hydrocarbon solvents, and halogenated hydrocarbon solvents. The reaction may be carried out in one type of organic solvent, in a mixed solvent of two or more types of organic solvents, in a mixed solvent of the organic solvent and another solvent, or without using an organic solvent.

[0039] Examples of ether solvents include diethyl ether and dibutyl ether. Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and ethylbenzene. Examples of aliphatic hydrocarbon solvents include n-hexane, n-heptane, and n-octane. Examples of halogenated hydrocarbon solvents include chloroform, carbon tetrachloride, monochlorobenzene, dichloromethane, 1,2-dichloroethane, and dichlorobenzene. Among these, aromatic hydrocarbon solvents such as toluene are preferred from the viewpoints of boiling point and solubility.

[0040] In this method, when Y is *-C(═O)-O-** or *-O-C(═O)-**, the quantitative relationship between the carboxylic acid and / or its derivative used as the raw material and the alcohol is such that the amount of alcohol is 0.5 to 1.5 moles, preferably 0.8 to 1.2 moles, and more preferably 0.9 to 1.1 moles per mole of the carboxylic acid and / or its derivative. The reaction temperature is not particularly limited, but may be, for example, 80 to 160°C, preferably 100 to 140°C. In the case of a transesterification method using an alkyl ester as the carboxylic acid derivative, it is preferable to carry out the reaction while removing the produced alcohol from the reaction system by azeotropy. Furthermore, when an carboxylic acid halide is used as the carboxylic acid derivative, it is preferable to remove the by-product hydrogen halide from the reaction system or add an amine such as triethylamine or pyridine to the reaction system as an acid scavenger. In this case, the amount of the acid scavenger added is about 0.8 to 1.5 times, preferably 0.9 to 1.2 times, and more preferably 1.0 to 1.1 times the amount of the carboxylic acid halide. When Y is *-O-**, the quantitative relationship between the alcohol and the alkylating agent used as the raw material, such as alcohol, alkyl halide, or alkyl tosylate, is such that the amount of alcohol is 0.5 to 1.5 moles, preferably 0.8 to 1.2 moles, and more preferably 0.9 to 1.1 moles per mole of the alkylating agent. The reaction temperature is not particularly limited, but the product can be synthesized by carrying out the reaction at, for example, 80 to 160°C, preferably 100 to 140°C. When Y is *--O--C(.dbd.O)--O--**, the quantitative relationship between the carbonate ester such as alkyl carbonate or phenyl carbonate used as the raw material and each alcohol is such that the amount of alcohol is 0.5 to 1.5 moles, preferably 0.8 to 1.2 moles, and more preferably 0.9 to 1.1 moles per mole of carbonate ester. The reaction temperature is not particularly limited, but the product can be synthesized by reacting at, for example, 80 to 160°C, preferably 100 to 140°C.

[0041] Stabilizer The phenolic compound represented by formula (I) is a compound that can act as a stabilizer for resins. The present invention also provides a stabilizer containing the above-mentioned phenolic compound of the present invention.

[0042] The stabilizer of the present invention may be an antioxidant, an antiaging agent, and / or a processing stabilizer. By adding the stabilizer of the present invention to an organic material such as a thermoplastic resin, thermal degradation and oxidative degradation of the organic material can be reduced, and the organic material can be stabilized, making it possible to prevent, for example, a decrease in viscosity and discoloration. Note that an antioxidant is an agent that can prevent oxidative degradation by preventing oxidation, an antiaging agent is an agent that can prevent deterioration of organic materials caused by various factors such as oxidation, and a processing stabilizer is an agent that can prevent deterioration caused by external forces, heat, oxygen, etc. when processing organic materials.

[0043] Adding the stabilizer of the present invention to an organic material such as a thermoplastic resin can reduce thermal and oxidative degradation of the organic material, stabilizing the organic material and preventing, for example, viscosity loss and discoloration during processing. It can also prevent deterioration of the resin over time. The stabilizer may be a material containing only the phenolic compound represented by formula (I) above, or it may be a material containing, in addition to the phenolic compound represented by formula (I), at least one other additive that can be contained in the resin composition described below. The stabilizer of the present invention may also be a material containing, in addition to the phenolic compound represented by formula (I), at least one organic material. Such a material is also referred to as a masterbatch.

[0044] [Organic Material Composition and Method for Stabilizing Organic Material] Adding a compound represented by formula (I) or a stabilizer of the present invention to an organic material reduces thermal and oxidative degradation of the organic material, stabilizing the organic material and preventing, for example, a decrease in viscosity. It is also believed that coloration can be prevented. Furthermore, it can prevent deterioration over time after processing of the resin. Therefore, the compound represented by formula (I) or the stabilizer of the present invention is suitable as a stabilizer for organic materials. In addition to the compound represented by formula (I) and the stabilizers containing the compound, the present invention also provides a method for stabilizing an organic material, in which the compound represented by formula (I) or a stabilizer containing the compound is added to the organic material. Furthermore, the present invention can also provide a stabilized resin composition containing an organic material and the compound represented by formula (I) or the stabilizer of the present invention.

[0045] Examples of organic materials that can be stabilized by the compound represented by formula (I) or the stabilizer of the present invention include, but are not limited to, the following organic materials: The organic material may be one type of organic material or a mixture of two or more types of organic materials.

[0046] (1) polyethylene, such as high density polyethylene (HD-PE), low density polyethylene (LD-PE), linear low density polyethylene (LLDPE), (2) polypropylene, (3) methylpentene polymer, (4) EEA (ethylene / ethyl acrylate copolymer) resin, (5) ethylene / vinyl acetate copolymer resin, (6) polystyrenes, such as polystyrene, poly(p-methylstyrene), poly(α-methylstyrene), (7) AS (acrylonitrile / styrene copolymer) resin, (8) ABS (acrylonitrile / butadiene / styrene copolymer) resin, (9) AAS (special acrylic rubber / acrylonitrile / styrene copolymer) resin, (10) ACS (acrylonitrile / chlorinated polyethylene / styrene copolymer) resin,

[0047] (11) chlorinated polyethylene, polychloroprene, chlorinated rubber, (12) polyvinyl chloride, polyvinylidene chloride, (13) methacrylic resin, (14) ethylene / vinyl alcohol copolymer resin, (15) fluororesin, (16) polyacetal, (17) grafted polyphenylene ether resin and polyphenylene sulfide resin, (18) polyurethane, (19) polyamide resin, for example, aliphatic polyamide, semi-aromatic polyamide, wholly aromatic polyamide, (20) polyester resin, for example, polyethylene terephthalate, polybutylene terephthalate,

[0048] (21) polycarbonate, (22) polyacrylate, (23) polysulfone, polyether ether ketone, polyether sulfone, (24) thermoplastic resin such as aromatic polyester resin, (25) epoxy resin, (26) diallyl phthalate prepolymer, (27) silicone resin, (28) unsaturated polyester resin, (29) acrylic-modified benzoguanamine resin, (30) benzoguanamine / melamine resin, (31) thermosetting resin such as urea resin,

[0049] (32) polybutadiene, (33) 1,2-polybutadiene, (34) polyisoprene, (35) styrene / butadiene copolymer, (36) butadiene / acrylonitrile copolymer, (37) ethylene / propylene copolymer, (38) silicone rubber, (39) epichlorohydrin rubber, (40) acrylic rubber, (41) natural rubber,

[0050] (42) Chlorinated rubber paint, (43) polyester resin paint, (44) urethane resin paint, (45) epoxy resin paint, (46) acrylic resin paint, (47) vinyl resin paint, (48) amino alkyd resin paint, (49) alkyd resin paint, (50) nitrocellulose resin paint, (51) oil-based paint, (52) wax, (53) lubricating oil, etc.

[0051] Among these, thermoplastic resins, particularly polyolefins such as polyethylene, for example, HD-PE, LD-PE, LLDPE and polypropylene, polyamide resins, engineering plastics such as polyethylene terephthalate, polybutylene terephthalate and polycarbonate are preferably used.

[0052] The polyolefin is not particularly limited, and may be, for example, one obtained by radical polymerization or one produced by polymerization using a catalyst containing a metal of Group IVb, Vb, VIb, or VIII of the periodic table. Examples of such metal-containing catalysts include metal complexes having one or more ligands, such as oxides, halides, alcoholates, esters, and aryls, coordinated by π or σ bonds. These complexes may be in the form of metal complexes themselves, or may be supported on a substrate such as magnesium chloride, titanium chloride, alumina, or silicon oxide. Preferred polyolefins are those produced using, for example, Ziegler-Natta catalysts, TNZ catalysts, metallocene catalysts, or Phillips catalysts.

[0053] Engineering plastics are also not particularly limited. Polyamide resins, such as aliphatic polyamides, semi-aromatic polyamides, and fully aromatic polyamides, are sufficient as long as they have an amide bond in the polymer chain and can be heated and melted. Polyamide resins may be produced by any method, including those produced by the condensation reaction of diamines and dicarboxylic acids, the condensation reaction of aminocarboxylic acids, and the ring-opening polymerization of lactams. Examples of polyamide resins include aliphatic polyamides such as nylon 66, nylon 69, nylon 610, nylon 612, poly-bis-(p-aminocyclohexyl)methandodecamide, nylon 46, nylon 6, nylon 12, and copolymers such as nylon 66 / 6 (a copolymer of nylon 66 and nylon 6) and nylon 6 / 12; semi-aromatic polyamides such as copolymers of nylon 6T, nylon 9T, nylon 10T, nylon 11T, nylon M5T, and nylon 6T / 66; and fully aromatic polyamides (aramids) such as para-aramid and meta-aramid. The polyester resin may be any resin having an ester bond in the polymer chain and capable of being melted by heating, such as a polyester obtained by polycondensation of a dicarboxylic acid and a dihydroxy compound. The polyester resin may be either a homopolyester or a copolyester. The polycarbonate resin may be any resin having a carbonate bond in the polymer chain and capable of being melted by heating, such as a polycarbonate obtained by reacting an aromatic hydroxy compound or a small amount of a polyhydroxy compound with a carbonate precursor such as phosgene or diphenyl carbonate in the presence of a solvent, an acid acceptor, and a molecular weight modifier. The polycarbonate resin may be linear or branched, or may be a copolymer.

[0054] By adding the phenolic compound represented by formula (I) to an organic material, the organic material can be stabilized.

[0055] When a phenolic compound represented by formula (I) or a stabilizer containing the compound is added to an organic material to stabilize the organic material, the content of the phenolic compound represented by formula (I) is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, and even more preferably 0.05 parts by mass or more, per 100 parts by mass of the organic material, from the viewpoint of stabilizing the organic material. Furthermore, the content of the phenolic compound represented by formula (I) is usually 5 parts by mass or less, preferably 3 parts by mass or less, and more preferably 1 part by mass or less, per 100 parts by mass of the organic material, from the viewpoint of efficiently stabilizing the organic material and being economical.

[0056] When the phenolic compound represented by formula (I) is added to an organic material, other additives may be added to the organic material as needed, such as a phenolic antioxidant (not included in formula (I)), a sulfur-based antioxidant, a phosphorus-based antioxidant, an ultraviolet absorber, a light stabilizer, a peroxide scavenger, a polyamide stabilizer, a hydroxyamine, a lubricant, a plasticizer, a flame retardant, a nucleating agent, a metal deactivator, an antistatic agent, a pigment, a filler, an antiblocking agent, a surfactant, a processing aid, a foaming agent, an emulsifier, a gloss agent, calcium stearate, hydrochloric acid, etc. It is also possible to add a neutralizing agent such as talcite, a color improver such as 9,10-dihydro-9-oxa-10-phosphophenanthrene-10-oxide, or a co-stabilizer such as benzofurans or indolines described in U.S. Patent Nos. 4,325,853, 4,338,244, 5,175,312, 5,216,053, 5,252,643, and 4,316,611, DE-A-4,316,622 and 4,316,876, EP-A-589,839, and EP-A-591,102. These additives can be added to the organic material simultaneously with the phenolic compound represented by formula (I) contained in the organic material composition of the present invention, or can be added to the organic material at a stage separate from the stage at which the phenolic compound represented by formula (I) contained in the organic material composition of the present invention is added. As the additive, one kind of additive may be used, or two or more kinds of additives may be used in combination.

[0057] Examples of phenolic antioxidants include the following. As the phenolic antioxidant, the following compounds may be used alone or in combination of two or more. (1) Examples of alkylated monophenols: 2,6-di-t-butyl-4-methylphenol, 2,4,6-tri-t-butylphenol, 2,6-di-t-butylphenol, 2-t-butyl-4,6-dimethylphenol, 2,6-di-t-butyl-4-ethylphenol, 2,6-di-t-butyl-4-n-butylphenol, 2,6-di-t-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2 ,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-t-butyl-4-methoxymethylphenol, 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methylundecyl-1'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadecyl-1'-yl)phenol, 2,4-dimethyl-6-(1'-methyltridecyl-1'-yl)phenol and mixtures thereof.

[0058] (2) Examples of alkylthiomethylphenols: 2,4-dioctylthiomethyl-6-t-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol, and mixtures thereof. (3) Examples of hydroquinone and alkylated hydroquinones: 2,6-di-t-butyl-4-methoxyphenol, 2,5-di-t-butylhydroquinone, 2,5-di-t-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-t-butylhydroquinone, 2,5-di-t-butyl-4-hydroxyanisole, 3,5-di-t-butyl-4-hydroxyphenyl stearate, bis(3,5-di-t-butyl-4-hydroxyphenyl)adipate, and mixtures thereof.

[0059] (4) Examples of tocopherols: α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, and mixtures thereof. (5) Examples of hydroxylated thiodiphenyl ethers: 2,2'-thiobis(6-t-butylphenol), 2,2'-thiobis(4-methyl-6-t-butylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol), 4,4'-thiobis(2-methyl-6-t-butylphenol), 4,4'-thiobis(3,6-di-t-amylphenol), 4,4'-(2,6-dimethyl-4-hydroxyphenyl)disulfide, and the like.

[0060] (6) Examples of alkylidene bisphenols and their derivatives: 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2,2'-methylenebis(4-ethyl-6-t-butylphenol), 2,2'-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol)], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylenebis(4-methyl-6-nonylphenol), 2,2'-methylenebis(4,6-di-t-butylphenol), 2,2'-ethylidenebis(4,6-di-t-butylphenol), 2,2'-ethylidenebis(4-isobutyl-6-t-butylphenol), 2,2'-methylenebis[6-(α-methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[4,6-(α,α- dimethylbenzyl)-4-nonylphenol], 4,4'-methylenebis(6-t-butyl-2-methylphenol), 4,4'-methylenebis(2,6-di-t-butylphenol), 4,4'-butylidenebis(3-methyl-6-t-butylphenol), 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(5-t-butyl-4-hydroxy-2-methylphenyl)butane, 2,6-bis(3-t-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-t-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-t-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane, ethylene glycol Bis[3,3-bis-3'-t-butyl-4'-hydroxyphenyl)butyrate], bis(3-t-butyl-4-hydroxy-5-methylphenyl)dicyclopentadiene, bis[2-(3'-t-butyl-2'-hydroxy-5'-methylbenzyl)-6-t-butyl-4-methylphenyl]terephthalate, 1,1-bis(3,5-dimethyl-2-hydroxyphenyl)butane, 2,2-bis(3,5-di-t-butyl-4-hydroxyphenyl)propane, 2,2-bis(5-t-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutane, 1,1,5,5-tetra(5-t-butyl-4-hydroxy-2-methylphenyl)pentane, 2-t-butyl-6-(3'-t-butyl-5'-methyl-2'-hydroxybenzyl)-4-methylphenyl acrylate, 2,4-di-t-pentyl-6-[1-(2-hydroxy-3,5-di-t-pentylphenyl)ethyl]phenyl acrylate, and mixtures thereof.

[0061] (7) Examples of O-, N- and S-benzyl derivatives: 3,5,3',5'-tetra-t-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl mercaptoacetate, tris(3,5-di-t-butyl-4-hydroxybenzyl)amine, bis(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-t-butyl-4-hydroxybenzyl)sulfide, isooctyl-3,5-di-t-butyl-4-hydroxybenzyl mercaptoacetate, and mixtures thereof. (8) Examples of hydroxybenzylated malonate derivatives include dioctadecyl-2,2-bis(3,5-di-t-butyl-2-hydroxybenzyl)malonate, dioctadecyl-2-(3-t-butyl-4-hydroxy-5-methylbenzyl)malonate, didodecylmercaptoethyl-2,2-bis(3,5-di-t-butyl-4-hydroxybenzyl)malonate, bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-t-butyl-4-hydroxybenzyl)malonate, and mixtures thereof. (9) Examples of aromatic hydroxybenzyl derivatives: 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 1,4-bis(3,5-di-t-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-tris(3,5-t-butyl-4-hydroxybenzyl)phenol, and mixtures thereof.

[0062] (10) Examples of triazine derivatives: 2,4-bis(n-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-1,3,5-triazine, 2-n-octylthio-4,6-bis(4-hydroxy-3,5-di-t-butylanilino)-1,3,5-triazine, 2-n-octylthio-4,6-bis(4-hydroxy-3,5-di-t-butylphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-t-butyl-4-phenoxy)-1,3,5-triazine, tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)iso cyanurate, tris(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate, 2,4,6-tris(3,5-di-t-butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 2,4,6-tris(3,5-di-t-butyl-4-hydroxyphenylpropyl)-1,3,5-triazine, tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate, tris[2-(3',5'-di-t-butyl-4'-hydroxycinnamoyloxy)ethyl]isocyanurate, and mixtures thereof.

[0063] (11) Examples of benzylphosphonate derivatives include dimethyl-3,5-di-t-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-t-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-t-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-t-butyl-4-hydroxy-3-methylbenzylphosphonate, calcium salt of 3,5-di-t-butyl-4-hydroxybenzylphosphonic acid monoester, and mixtures thereof. (12) Examples of acylaminophenol derivatives include 4-hydroxylauric acid anilide, 4-hydroxystearic acid anilide, octyl-N-(3,5-di-t-butyl-4-hydroxyphenyl)carbamate, and mixtures thereof. (13) Examples of esters of β-(3,5-di-t-butyl-4-hydroxyphenyl)propionic acid with the following monohydric or polyhydric alcohols: methanol, ethanol, octanol, octadecanol, ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiroglycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2,2,2]octane, and mixtures thereof.

[0064] (14) Examples of esters of β-(5-t-butyl-4-hydroxy-3-methylphenyl)propionic acid with the following monohydric or polyhydric alcohols: methanol, ethanol, octanol, octadecanol, ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiroglycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2,2,2]octane, and mixtures thereof. (15) Examples of esters of β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with the following monohydric or polyhydric alcohols: methanol, ethanol, octanol, octadecanol, ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiroglycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2,2,2]octane, and mixtures thereof.

[0065] (16) Examples of esters of 3,5-di-t-butyl-4-hydroxyphenylacetic acid with the following monohydric or polyhydric alcohols: methanol, ethanol, octanol, octadecanol, ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiroglycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2,2,2]octane, and mixtures thereof. (17) Examples of amides of β-(3,5-di-t-butyl-4-hydroxyphenyl)propionic acid include N,N'-bis[3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionyl]hydrazine, N,N'-bis[3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionyl]hexamethylenediamine, N,N'-bis[3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionyl]trimethylenediamine, and mixtures thereof.

[0066] Examples of sulfur-based antioxidants include dilauryl 3,3'-thiodipropionate, tridecyl 3,3'-thiodipropionate, dimyristyl 3,3'-thiodipropionate, distearyl 3,3'-thiodipropionate, lauryl stearyl 3,3'-thiodipropionate, and neopentanetetrayltetrakis(3-laurylthiopropionate).

[0067] Examples of phosphorus-based antioxidants include the following: As the phosphorus-based antioxidant, the following compounds may be used alone or in combination of two or more: triphenyl phosphite, tris(nonylphenyl) phosphite, tris(2,4-di-t-butylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, diisodecyl pentaerythritol diphosphite, bis(2,4-di-t-butylphenyl)pentaerythritol diphosphite, bis(2,4-di-t-butyl-6-methylphenyl)pentaerythritol diphosphite, bis(2,6-di-t-butyl-4-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-t-butylphenyl)pentaerythritol Diphosphite, tristearyl sorbitol triphosphite, tetrakis(2,4-di-t-butylphenyl)-4,4'-diphenylene diphosphonite, 2,2'-methylenebis(4,6-di-t-butylphenyl) 2-ethylhexyl phosphite, 2,2'-ethylidenebis(4,6-di-t-butylphenyl) fluorophosphite, bis(2,4-di-t-butyl-6-methylphenyl) ethyl phosphite, bis(2,4-di-t-butyl-6-methylphenyl) methyl phosphite, 2-(2,4,6-tri-t-butylphenyl)-5-ethyl-5-butyl-1,3,2-oxaphosphorinane, 2,2',2''-nitrilo[triethyl-tris(3,3',5,5'-tetra-t-butyl-1,1'-biphenyl-2,2'-diyl)] phosphite, 6-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-t-butyldibenz[d,f][1,3,2]dioxaphosphepine, and mixtures thereof.

[0068] Examples of ultraviolet absorbers include the following: As ultraviolet absorbers, the following compounds may be used alone or in combination of two or more. (1) Examples of salicylate derivatives: phenyl salicylate, 4-t-butylphenyl salicylate, 2,4-di-t-butylphenyl 3',5'-di-t-butyl-4'-hydroxybenzoate, 4-t-octylphenyl salicylate, bis(4-t-butylbenzoyl)resorcinol, benzoylresorcinol, hexadecyl 3',5'-di-t-butyl-4'-hydroxybenzoate, octadecyl 3',5'-di-t-butyl-4'-hydroxybenzoate, 2-methyl-4,6-di-t-butylphenyl 3',5'-di-t-butyl-4'-hydroxybenzoate, and mixtures thereof. (2) Examples of 2-hydroxybenzophenone derivatives include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2,2′-dihydroxy-4-methoxybenzophenone, bis(5-benzoyl-4-hydroxy-2-methoxyphenyl)methane, 2,2′,4,4′-tetrahydroxybenzophenone, and mixtures thereof.

[0069] (3) Examples of 2-(2'-hydroxyphenyl)benzotriazole: 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-(3',5'-di-t-butyl-2'-hydroxyphenyl)benzotriazole, 2-(5'-t-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 2-(3-t-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole, 2-(3'-s-butyl-2'-hydroxy-5'-t-butylphenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazole, 2-(3',5'-di-t-amyl-2'-hydroxyphenyl)benzotriazole azole, 2-[2'-hydroxy-3',3'-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, 2-[(3'-t-butyl-2'-hydroxyphenyl)-5'-(2-octyloxycarbonylethyl)phenyl]-5-chlorobenzotriazole, 2-[3'-t-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl]-5-chlorobenzotriazole, 2-[3'-t-butyl-3'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl]-5-chlorobenzotriazole, 2-[3'-t-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl] Benzotriazole, 2-[3'-t-butyl-2'-hydroxy-5-(2-octyloxycarbonylethyl)phenyl]benzotriazole, 2-[3'-t-butyl-2'-hydroxy-5'-[2-(2-ethylhexyloxy)carbonylethyl]phenyl]benzotriazole, 2-[2-hydroxy-3-(3,4,5,6-tetrahydrophthalimidomethyl)-5-methylphenyl]benzotriazole, 2-(3,5-di-t-butyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl)benzotriazole and 2-[3'-t-butyl-2'-hydroxy-5'-(2-isooctyloxycarbonylethyl)phenyl]benzotriazole mixture, 2,2'-Methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol, 2,2'-methylenebis[4-t-butyl-6-(2H-benzotriazol-2-yl)phenol], condensation products of poly(3-11)(ethylene glycol) and 2-[3'-t-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl]benzotriazole, condensation products of poly(3-11)(ethylene glycol) and methyl 3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxyphenyl]propionate, 2-ethylhexyl 3-[3-t-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate, octyl 3-[3-t-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate, methyl 3-[3-t-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate, 3-[3-t-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionic acid, and mixtures thereof.

[0070] Examples of light stabilizers include the following: As light stabilizers, the following compounds may be used alone or in combination of two or more. (1) Examples of hindered amine light stabilizers: bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(N-octoxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(N-benzyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(N-cyclohexyloxy-2,2,6,6-tetramethyl-4- piperidyl) sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) 2-(3,5-di-t-butyl-4-hydroxybenzyl)-2-butylmalonate, bis(1-acryloyl-2,2,6,6-tetramethyl-4-piperidyl) 2,2-bis(3,5-di-t-butyl-4-hydroxybenzyl)-2-butylmalonate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) decanedioate, 2,2,6,6-tetramethyl-4-piperidyl Methacrylate, 4-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxy]-1-[2-(3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxy)ethyl]-2,2,6,6-tetramethylpiperidine, 2-methyl-2-(2,2,6,6-tetramethyl-4-piperidyl)amino-N-(2,2,6,6-tetramethyl-4-piperidyl)propionyl Pionamide, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)1,2,3,4-butanetetracarboxylate, tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)1,2,3,4-butanetetracarboxylate, mixed esters of 1,2,3,4-butanetetracarboxylic acid with 1,2,2,6,6-pentamethyl-4-piperidinol and 1-tridecanol,

[0071] Mixed esters of 1,2,3,4-butanetetracarboxylic acid with 2,2,6,6-tetramethyl-4-piperidinol and 1-tridecanol, mixed esters of 1,2,3,4-butanetetracarboxylic acid with 1,2,2,6,6-pentamethyl-4-piperidinol and 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, mixed esters of 1,2,3,4-butanetetracarboxylic acid with 2,2,6,6-tetramethyl-4-piperidinol and 3,9-bis(2-hydroxy-1 ,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane mixed ester, polycondensation product of dimethyl succinate and 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine, poly[(6-morpholino-1,3,5-triazine-2,4-diyl)((2,2,6,6-tetramethyl-4-piperidyl)imino)hexamethylene((2,2,6,6-tetramethyl-4-piperidyl)imino)], poly[(6-(1,1,3,3-tetramethylbutyl)imino-1,3,5-triazine-2,4-diyl)((2,2,6,6-tetramethyl-4-piperidyl)imino)] Triazine-2,4-diyl((2,2,6,6-tetramethyl-4-piperidyl)imino)hexamethylene((2,2,6,6-tetramethyl-4-piperidyl)imino)], polycondensation product of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 1,2-dibromoethane, N,N',4,7-tetrakis[4,6-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-1,3,5-triazin-2-yl]-4,7-diazadecane-1,10-diamine, N,N',4-triazin-2,4-diyl((2,2,6,6-tetramethyl-4-piperidyl)imino)hexamethylenediamine and 1,2-dibromoethane, Tris[4,6-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-1,3,5-triazin-2-yl]-4,7-diazadecane-1,10-diamine, N,N',4,7-tetrakis[4,6-bis(N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino)-1,3,5-triazin-2-yl]-4,7-diazadecane-1,10-diamine, N,N',4-tris[4,6-bis(N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino)-1,3,5-triazin-2-yl]-4,7-diazadecane-1,10-diamine and mixtures thereof.

[0072] (2) Examples of acrylate-based light stabilizers include ethyl α-cyano-β,β-diphenylacrylate, isooctyl α-cyano-β,β-diphenylacrylate, methyl α-carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate, butyl α-cyano-β-methyl-p-methoxycinnamate, methyl α-carbomethoxy-p-methoxycinnamate, N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline, and mixtures thereof. (3) Examples of nickel-based light stabilizers include nickel complexes of 2,2'-thiobis-[4-(1,1,3,3-tetramethylbutyl)phenol], nickel dibutyldithiocarbamate, nickel salts of monoalkyl esters, nickel complexes of ketoximes, and mixtures thereof.

[0073] (4) Examples of oxamide-based light stabilizers: 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-t-butylanilide, 2,2'-didodecyloxy-5,5'-di-t-butylanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-t-butyl-2'-ethoxyanilide, 2-ethoxy-5,4'-di-t-butyl-2'-ethyloxanilide, and mixtures thereof. (5) Examples of 2-(2-hydroxyphenyl)-1,3,5-triazine-based light stabilizers: 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2,4-dihydroxyphenyl-4,6-bis(2,4-dimethylphenyl]-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis (4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, and mixtures thereof.

[0074] Examples of metal deactivators include N,N'-diphenyloxamide, N-salicylal-N'-salicyloylhydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5-di-t-butyl-4-hydroxyphenylpropionyl)hydrazine, 3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyldihydrazide, oxanilide, isophthaloyldihydrazide, sebacoylbisphenylhydrazide, N,N'-bis(salicyloyl)oxalyldihydrazide, N,N'-bis(salicyloyl)thiopropionyldihydrazide, and mixtures thereof.

[0075] Examples of peroxide scavengers include esters of β-thiodipropionic acid, mercaptobenzimidazole, zinc salts of 2-mercaptobenzimidazole, zinc salts of dibutyldithiocarbamic acid, dioctadecyl disulfide, pentaerythritol tetrakis(β-dodecylmercapto)propionate, and mixtures thereof.

[0076] Examples of polyamide stabilizers include copper compounds. Examples of copper compounds include copper (I) chloride, copper (II) chloride, copper (I) bromide, copper (II) bromide, copper (I) iodide, copper acetate, copper propionate, copper benzoate, copper adipate, copper terephthalate, copper isophthalate, copper sulfate, copper phosphate, copper borate, copper nitrate, copper stearate, copper complex salts coordinated with chelating agents, and mixtures thereof. Among these, copper halides are preferred, and copper (I) iodide is more preferred.

[0077] The polyamide stabilizer may be a combination of a copper compound and an alkali metal halide compound, such as potassium iodide, potassium bromide, potassium chloride, sodium iodide, sodium bromide, sodium chloride, or a mixture thereof, with potassium iodide being preferred.

[0078] Examples of hydroxyamines include N,N-dibenzylhydroxyamine, N,N-diethylhydroxyamine, N,N-dioctylhydroxyamine, N,N-dilaurylhydroxyamine, N,N-ditetradecylhydroxyamine, N,N-dihexadecylhydroxyamine, N,N-dioctadecylhydroxyamine, N-hexadecyl-N-octadecylhydroxyamine, N-heptadecyl-N-octadecylhydroxyamine, and mixtures thereof.

[0079] Examples of the neutralizing agent include calcium stearate, zinc stearate, magnesium stearate, hydrotalcite (basic magnesium aluminum hydroxy carbonate hydrate), melamine, amine, polyamide, polyurethane, and mixtures thereof.

[0080] Examples of lubricants include aliphatic hydrocarbons such as paraffin and wax, higher fatty acids having 8 to 22 carbon atoms, metal (Al, Ca, Mg, Zn) salts of higher fatty acids having 8 to 22 carbon atoms, aliphatic alcohols having 8 to 22 carbon atoms, polyglycols, esters of higher fatty acids having 4 to 22 carbon atoms and aliphatic monohydric alcohols having 4 to 18 carbon atoms, higher aliphatic amides having 8 to 22 carbon atoms, silicone oils, and rosin derivatives.

[0081] Examples of nucleating agents include sodium 2,2'-methylenebis(4,6-di-t-butylphenyl)phosphate, [2,2'-methylenebis(4,6-di-t-butylphenyl)phosphate]dihydroxyaluminum, bis[2,2'-methylenebis(4,6-di-t-butylphenyl)phosphate]hydroxyaluminum, tris[2,2'-methylenebis(4,6-di-t-butylphenyl)phosphate]aluminum, sodium Bis(4-t-butylphenyl)phosphate, metal salts of benzoic acid such as sodium benzoate, aluminum p-t-butylbenzoate, 1,3:2,4-bis(O-benzylidene)sorbitol, 1,3:2,4-bis(O-methylbenzylidene)sorbitol, 1,3:2,4-bis(O-ethylbenzylidene)sorbitol, 1,3-O-3,4-dimethylbenzylidene-2,4-O-benzylidene sorbitol, 1,3-O-benzylidene and mixtures thereof.

[0082] Examples of fillers include calcium carbonate, silicates, glass fibers, asbestos, talc, kaolin, mica, barium sulfate, carbon black, carbon fibers, zeolites, and mixtures thereof.

[0083] Among these additives, those preferably used are phenol-based antioxidants, phosphorus-based antioxidants, ultraviolet absorbers, hindered amine-based light stabilizers, peroxide scavengers and neutralizing agents.

[0084] Particularly preferred phenolic antioxidants include the following compounds: 2,6-di-t-butyl-4-methylphenol, 2,4,6-tri-t-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,2'-thiobis(6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2,2'-methylenebis(4-ethyl-6-t-butylphenol), 2,2'-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol)], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2 '-Methylenebis(4,6-di-t-butylphenol), 2,2'-ethylidenebis(4,6-di-t-butylphenol), 4,4'-methylenebis(6-t-butyl-2-methylphenol), 4,4'-methylenebis(2,6-di-t-butylphenol), 4,4'-butylidenebis(3-methyl-6-t-butylphenol), 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(5-t-butyl-4-hydroxy-2-methylphenyl)butane, 1,1,3-tris(5-t-butyl-4-hydroxy-2-methylphenyl)butane, ethylene glycol Bis[3,3-bis-3'-t-butyl-4'-hydroxyphenyl)butyrate], 2-t-butyl-6-(3'-t-butyl-5'-methyl-2'-hydroxybenzyl)-4-methylphenyl acrylate, 2,4-di-t-pentyl-6-[1-(2-hydroxy-3,5-di-t-pentylphenyl)ethyl]phenyl acrylate,

[0085] 2,4,6-tris(3,5-di-t-butyl-4-phenoxy)-1,3,5-triazine, tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, bis(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate, tris[2-(3',5'-di-t-butyl-4'-hydroxycinnamoyloxy)ethyl]isocyanurate, diethyl-3,5-di-t-butyl-4-hydroxybenzylphosphonate, di-n-octadecyl-3,5-di-t-butyl-4-hydroxybenzylphosphonate, calcium salt of 3,5-di-t-butyl-4-hydroxybenzylphosphonic acid monoester, n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, neopentanetetrayltetrakis(3,5-di-t-butyl-4-hydroxycinnamate), thiodiethylene bis(3,5-di-t-butyl-4-hydroxycinnamate), 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 3,6-dioxaoctamethylene bis(3,5-di-t-butyl-4-hydroxycinnamate), hexamethylene bis(3,5-di-t-butyl-4-hydroxycinnamate), triethylene glycol Bis(5-t-butyl-4-hydroxy-3-methylcinnamate), N,N'-bis[3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionyl]hydrazine, N,N'-bis[3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionyl]hexamethylenediamine, and the like.

[0086] Particularly preferred phosphorus-based antioxidants include the following compounds: tris(nonylphenyl)phosphite, tris(2,4-di-t-butylphenyl)phosphite, distearyl pentaerythritol diphosphite, bis(2,4-di-t-butylphenyl)pentaerythritol diphosphite, bis(2,4-di-t-butyl-6-methylphenyl)pentaerythritol diphosphite, bis(2,6-di-t-butyl-4-methylphenyl)pentaerythritol diphosphite, tetrakis(2,4-di-t-butylphenyl)-4,4'-diphenylenediphosphonite, 2,2'-methylenebis(4,6-di-t-butylphenyl)2-ethylhexyl phosphite, 2,2'-ethylidenebis(4,6-di-t-butylphenyl)fluorophosphite, and bis(2,4-di-t-butyl-6-methylphenyl). ethyl phosphite, 2-(2,4,6-tri-t-butylphenyl)-5-ethyl-5-butyl-1,3,2-oxaphosphorinane, 2,2',2''-nitrilo[triethyl-tris(3,3',5,5'-tetra-t-butyl-1,1'-biphenyl-2,2'-diyl)phosphite, 6-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-t-butyldibenz[d,f][1,3,2]dioxaphosphepine, and the like.

[0087] Particularly preferred ultraviolet absorbers include the following compounds: phenyl salicylate, 4-t-butylphenyl salicylate, 2,4-di-t-butylphenyl 3',5'-di-t-butyl-4'-hydroxybenzoate, 4-t-octylphenyl salicylate, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, bis(5-benzoyl-4-hydroxy-2-methoxyphenyl)methane, 2,2',4,4'-tetrahydroxybenzophenone, 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-(3',5'-di-t-butyl-2'-hydroxyphenyl)benzotriazole, and 2-(5'-t-butyl-2'-hydroxyphenyl)benzotriazo. 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 2-(3-t-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole, 2-(3'-s-butyl-2'-hydroxy-5'-t-butylphenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazole, 2-(3',5'-di-t-amyl-2'-hydroxyphenyl)benzotriazole, 2-[2'-hydroxy-3',5'-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, and the like.

[0088] Particularly preferred light stabilizers include the following compounds: bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(N-octoxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(N-benzyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(N-cyclohexyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) 2-(3,5-di-t-butyl-4-hydroxybenzyl)-2-butylmalonate, and bis(1-acroyl-2,2,6,6-tetramethyl-4-piperidyl). 2,2-bis(3,5-di-t-butyl-4-hydroxybenzyl)-2-butylmalonate, bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, 4-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxy]-1-[2-(3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxy)ethyl]-2,2,6,6-tetramethylpiperidine, 2-methyl-2-(2,2,6,6-tetramethyl-4-piperidyl)amino-N-(2,2,6,6-tetramethyl-4-piperidyl)propionamide, tetrakis(2,2,6,6-tetramethyl-4-piperidyl) 1,2,3,4-butanetetracarboxylate,

[0089] Tetrakis(1,2,6,6-pentamethyl-4-piperidyl) 1,2,3,4-butanetetracarboxylate, mixed esters of 1,2,3,4-butanetetracarboxylic acid with 1,2,2,6,6-pentamethyl-4-piperidinol and 1-tridecanol, mixed esters of 1,2,3,4-butanetetracarboxylic acid with 2,2,6,6-tetramethyl-4-piperidinol and 1-tridecanol, mixed esters of 1,2,3,4-butanetetracarboxylic acid with 1,2,2,6,6-pentamethyl- Mixed esters of 4-piperidinol and 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, mixed esters of 1,2,3,4-butanetetracarboxylic acid with 2,2,6,6-tetramethyl-4-piperidinol and 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, dimethyl Polycondensation products of succinate and 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine, poly[(6-morpholino-1,3,5-triazine-2,4-diyl)((2,2,6,6-tetramethyl-4-piperidyl)imino)hexamethylene((2,2,6,6-tetramethyl-4-piperidyl)imino)], poly[(6-(1,1,3,3-tetramethylbutyl)-1,3,5-triazine-2,4-diyl)((2,2,6,6-tetramethyl-4-piperidyl)imino)hexamethylene((2,2,6,6-tetramethyl-4-piperidyl)imino)], and the like.

[0090] The phenolic compound represented by formula (I) or the stabilizer of the present invention, together with other optional additives, can be added to an organic material using any known method and apparatus for obtaining a homogeneous mixture. For example, when adding a phenolic compound represented by formula (I), if the organic material is a solid polymer, the compound and / or other optional additives can be dry-blended directly with the solid polymer, or the phenolic compound represented by formula (I) and / or other optional additives can be added to the solid polymer in the form of a masterbatch. If the organic material is a liquid polymer, in addition to the above-mentioned addition methods, the phenolic compound represented by formula (I) and / or other optional additives can be blended in the form of a solution or dispersion into the polymer solution during or immediately after polymerization. On the other hand, when the organic material is a liquid other than a solid polymer (for example, oil), in addition to the above-mentioned addition method, the phenolic compound represented by formula (I) and / or other additives added as needed can be directly added to the organic material to dissolve it, or the phenolic compound represented by formula (I) and / or other additives added as needed can be added in a dissolved or suspended state in a liquid medium.

[0091] The phenolic compound represented by formula (I) and the stabilizer of the present invention have excellent properties as stabilizers for various organic materials, including thermoplastic resins such as polyolefins. Organic materials to which the phenolic compound represented by formula (I) and / or the stabilizer of the present invention have been added are stable against thermal and oxidative degradation during production, processing, and use, resulting in high-quality products.

[0092] The present invention will be described in more detail below based on examples and comparative examples, but the present invention is not limited to the following examples.

[0093] [Synthesis of 2,6-di-tert-butyl-4-(3-hydroxypropyl)phenol] A stirrer, 5.12 g (135 mmol) of sodium borohydride, 6.14 g (145 mmol) of aluminum chloride, and 99 ml of tetrahydrofuran were added to a four-neck flask under ice cooling and stirred for 1 hour. To this was added a solution of 22.00 g (75.2 mmol) of methyl 3-(4-hydroxy-3,5-di-tert-butyl-phenyl)propionate dissolved in 50 ml of tetrahydrofuran, and the mixture was allowed to react for 6 hours while heating under reflux in an 80°C oil bath. After the reaction, 132 ml of 1N aqueous HCl was added under ice cooling to terminate the reaction. The mixture was then separated from the aqueous layer using ethyl acetate as an extraction solvent and washed once with saturated saline. The organic layer was concentrated and dried, and the resulting crude product was purified by silica gel column chromatography to obtain 18.1 g of 2,6-tert-butyl-4-(3-hydroxypropyl)phenol in a 91% yield.

[0094] [Synthesis of 2-methyl-6-tert-butyl-4-(3-hydroxypropyl)phenol] 2,6-tert-butyl-4-(3-hydroxypropyl)phenol was obtained in the same synthetic method as for 2,6-di-tert-butyl-4-(3-hydroxypropyl)phenol, except that methyl 3-(4-hydroxy-3-methyl-5-tert-butyl-phenyl)propionate was used as the raw material.

[0095] [Synthesis of 8-(dodecyloxy)octanol] A four-neck flask was charged with a stirrer, 22.1 g (150.2 mmol) of 1,8-octanediol, 62 ml of dimethyl sulfoxide, and 125 ml of tetrahydrofuran. Then, 2.2 g (55.1 mmol) of sodium hydride was added under ice cooling and stirred for 2 hours. 1.89 g (5.0 mmol) of tetrabutylammonium iodide was added to the reaction solution, and a solution prepared from 12.4 g (50.1 mmol) of 1-bromododecane and 31 ml of tetrahydrofuran was added dropwise. The mixture was stirred overnight at room temperature. 270 ml of ion-exchanged water and 270 ml of ethyl acetate were added under ice cooling, and separation and extraction were performed twice. The ethyl acetate layers were combined and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 8.2 g of 8-(dodecyloxy)octanol in a yield of 52.2%.

[0096] [Synthesis of 8-(2-(nonyloxy)ethoxy)octan-1-ol] The intermediate 2-(nonyloxy)ethan-1-ol was obtained in a yield of 68.8% by the same synthetic method as for 8-(dodecyloxy)octanol, except that ethylene glycol and 1-bromononane were used as raw materials. A stirrer, 9.19 g (48.8 mmol) of 2-(nonyloxy)ethan-1-ol, 7.53 mL (53.6 mmol) of triethylamine, 0.60 g (4.88 mmol) of 4-dimethylaminopyridine, and 128 mL of dichloromethane were placed in a four-neck flask, and then 9.87 g (51.2 mmol) of p-toluenesulfonyl chloride was added under ice cooling and the mixture was stirred at room temperature for 3 hours. The mixture was extracted with 190 ml of ion-exchanged water and 120 ml of chloroform, and the chloroform layer was washed with 1 N aqueous HCl and saturated saline, followed by concentration under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain the alkylating agent 2-(nonyloxy)ethyl-4-methylbenzenesulfonate in a yield of 95.2%. Next, 12.0 g of 8-(2-(nonyloxy)ethoxy)octan-1-ol was obtained in a yield of 81.6% by the same synthetic method as for 8-(dodecyloxy)octanol, except that 2-(nonyloxy)ethyl-4-methylbenzenesulfonate was used as the starting material.

[0097] [Synthesis of 6-(2-(2-(octyloxy)ethoxy)ethoxy)hexan-1-ol] 3.9 g of 6-(2-(2-(octyloxy)ethoxy)ethoxy)hexan-1-ol was obtained in a yield of 74.4% in the same manner as for 8-(2-(nonyloxy)ethoxy)octan-1-ol, except that diethylene glycol, 1-bromooctane, and 1,6-hexanediol were used as raw materials.

[0098] [Synthesis of 2-octyldodecanoic acid] A four-neck flask was charged with a stirrer, 10.0 g (30.4 mmol) of 2-octyldodecanol, 0.3 g (2.1 mmol) of 2,2,6,6-tetramethylpiperidine-1-oxyl free radical, 145 ml of acetonitrile, and 109 ml of 0.67 M phosphate buffer solution, and the mixture was stirred at 35°C for 30 minutes. A solution of sodium chlorite (5.5 g, 60.8 mmol) in water (72 ml) and bleach (5.0 ml, 6 wt%) were added. The reaction mixture was left overnight at room temperature. Additional bleach (5.0 mL) was added, and the resulting mixture was stirred for an additional 2 hours at 35°C. After confirming the disappearance of the raw materials, 145 ml of 1N aqueous HCl solution was added under ice cooling, and the mixture was separated from the aqueous layer using ethyl acetate as an extraction solvent. The ethyl acetate layer was concentrated under reduced pressure to obtain crude 2-octyldodecanoic acid.

[0099] [Synthesis of 3,7,11,15-tetramethylhexadecanoic acid] A crude product of 3,7,11,15-tetramethylhexadecanoic acid was obtained in the same synthesis method as for 2-octyldodecanoic acid, except that dihydrophytol was used as the raw material.

[0100] [Synthesis of 8-(dodecyloxy)octanoic acid] A crude product of 8-(dodecyloxy)octanoic acid was obtained in the same manner as in the synthesis of 2-octyldodecanoic acid, except that 8-(dodecyloxy)octanol was used as the raw material.

[0101] Example 1 5.75 g (23.2 mmol) of methyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate, 7.45 g (23.6 mmol) of 8-(dodecyloxy)octanol, 1.24 g (4.74 mmol) of dibutyltin oxide, and 6.6 ml of toluene were charged into a four-neck flask and stirred under reflux for 2 hours under a nitrogen atmosphere. A Dean-Stark apparatus was used for the reaction, and toluene was extracted each time it accumulated in the Dean-Stark apparatus, and the same amount of toluene was added to the reaction solution. After completion of the reaction, toluene was removed by distillation under reduced pressure, and the resulting solid was washed with ethyl acetate and then purified by silica gel chromatography to obtain 10.8 g of phenolic compound A-1 represented by formula (A-1) in a yield of 87.5% and a purity of 98.2%.

[0102] １ H-NMR (CDCl ３ , 400MHz): δ: 6.95 (1H, s), 6.84 (1H, s), 4.68 (1H, s), 4.05 (2H, t, J = 6.7Hz), 3.39 (4H, t, J = 6.7Hz), 2.84 (2H, t, J = 7.8Hz) , 2.57 (2H, t, J=7.8Hz), 2.22 (3H, s), 1.57 (21H, s), 1.40 (9H, s), 1.30-1.26 (25H, brm), 0.88 (3H, t, J=7.0Hz)

[0103] Example 2 The same procedure as in Example 1 was conducted except that 8-(2-(nonyloxy)ethoxy)octan-1-ol was used as the raw material, to obtain 15.8 g of a phenolic compound A-2 represented by formula (A-2) in a yield of 79.7% and a purity of 98.1%.

[0104] １ H-NMR (CDCl ３, 400MHz): δ: 6.95 (1H, d, J = 2.2Hz), 6.85-6.82 (1H, brm), 4.70 (1H, s), 4.05 (2H, t, J = 6.7Hz), 3.57, (4H, s ), 3.45 (4H, t, J = 6.7Hz), 2.84 (2H, t, J = 7.9Hz), 2.59-2.56 (2H, m), 2.22 (3H, s ), 1.58-1.57 (7H, m), 1.40 (9H, s), 1.30-1.26 (20H, brm), 0.88 (3H, t, J=6.8Hz)

[0105] Example 3 The same procedure as in Example 1 was conducted except that 6-(2-(2-(octyloxy)ethoxy)ethoxy)hexan-1-ol was used as the raw material, to obtain 13.7 g of phenolic compound A-3 represented by formula (A-3) in a yield of 87.6% and a purity of 97.9%.

[0106] １ H-NMR (CDCl ３ , 400MHz): δ: 6.95 (1H, d, J = 2.0Hz), 6.83 (1H, d, J = 2.0Hz), 4.83 (1H, s), 4.05 ( 2H, t, J=6.6Hz), 3.66-3.64 (4H, m), 3.59-3.58 (4H, m), 3.45-3.43 (4 H, m), 2.84 (2H, t, J=7.8Hz), 2.60-2.56 (2H, m), 2.22 (3H, s), 1.61- 1.53 (6H, m), 1.40 (9H, s), 1.31-1.26 (15H, m), 0.87 (3H, t, J=6.8Hz)

[0107] Example 4 The same procedure as in Example 1 was conducted except that methyl 3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate was used as the raw material, to obtain 9.54 g of a phenolic compound A-4 represented by formula (A-4) in a yield of 67.9% and a purity of 99.0%.

[0108] １ H-NMR (CDCl ３, 400MHz): δ: 6.99 (2H, s), 5.06 (1H, s), 4.07 (2H, t, J=6.7 Hz), 3.39 (4H, t, J=6.7Hz), 2.88-2.85 (2H, m), 2.60-2.58 (2H, m), 1.61 -1.54 (6H, m), 1.43 (18H, s), 1.31-1.26 (26H, m), 0.88 (3H, t, J=7.9Hz)

[0109] Example 5 The same procedure as in Example 2 was conducted except that methyl 3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate was used as the raw material, to obtain 6.72 g of a phenolic compound A-5 represented by formula (A-5) in a yield of 80.2% and a purity of 99.1%.

[0110] １ H-NMR (CDCl ３ , 400MHz): δ: 6.97 (2H, s), 5.05 (1H, s), 4.05 (2H, t, J = 6.8Hz), 3.55 (4H, s), 3.43 (4H, t, J = 6.8Hz), 2.86-2.84 ( 2H, m), 2.58-2.56 (2H, m), 1.60-1.53 ​​(6H, m), 1.41 (18H, s), 1.28-1.26 (20H, brm), 0.87-0.85 (3H, m)

[0111] Example 6 The same procedure as in Example 1 was conducted except that methyl 3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate and dihydrophytol were used as raw materials, to obtain 5.82 g of phenolic compound A-6 represented by formula (A-6) in a yield of 81.2% and a purity of 99.6%.

[0112] １ H-NMR (CDCl ３ , 400MHz): δ: 6.99 (2H, s), 5.06 (1H, s), 4.13-4.09 (2H, m), 2.88-2.85 (2H, m), 2.60-2.58 (2H, m), 1.66-1.03 (42H, m), 0.88-0.85 (15H, m)

[0113] Example 7 The same procedure as in Example 6 was conducted except that phytol was used as the raw material, to obtain 3.59 g of a phenolic compound A-7 represented by formula (A-7) in a yield of 75.7% and a purity of 97.4%.

[0114] １ H-NMR (CDCl ３ , 400MHz): δ: 6.99 (2H, s), 5.35-5.32 (1H, m), 5.07 (1H, s), 4.61 (2H, d, J = 7.1Hz), 2.88-2.86 (2H, m), 2.61 -2.59 (2H, m), 2.01-1.99 (2H, m), 1.69 (3H, d, J = 1.2Hz), 1.58-1.03 (39H, m), 0.87-0.85 (12H, m)

[0115] Example 8: 4.00 g of crude 8-(dodecyloxy)octanoic acid synthesized from 8-(dodecyloxy)octanol, 23 ml of dichloromethane solvent, and 0.09 ml (1.2 mmol) of dimethylformamide were placed in a four-neck flask, and 4.36 ml (60.8 mmol) of thionyl chloride was added dropwise under ice cooling in a nitrogen atmosphere. The mixture was then heated to 40°C and stirred under reflux for 2 hours. Excess thionyl chloride was removed by vacuum distillation, and 5 ml of tetrahydrofuran was added to obtain an acid chloride intermediate solution. 2.71 g (12.2 mmol) of 2-methyl-6-tert-butyl-4-(3-hydroxypropyl)phenol, 2.03 ml (14.6 mmol) of triethylamine, and 24 ml of tetrahydrofuran were placed in a four-neck flask, and the acid chloride intermediate solution was added dropwise under ice cooling. The mixture was stirred at room temperature for 2 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was separated and washed with ethyl acetate and ion-exchanged water, and then the ethyl acetate layer was concentrated under reduced pressure to obtain a crude product, which was purified by silica gel chromatography to obtain 4.1 g of phenolic compound A-8 represented by formula (A-8) in a yield of 63.3% and a purity of 99.4%.

[0116] １ H-NMR (CDCl ３, 400MHz): δ: 6.93 (1H, d, J = 2.2Hz), 6.81 (1H, d, J = 1.7Hz), 4.66 (1H, s), 4.08 ( 2H, t, J = 6.6Hz), 3.39-3.37 (4H, m), 2.58-2.56 (2H, m), 2.30 (2H, t, J =7.6Hz), 2.22 (3H, s), 1.94-1.87 (2H, m), 1.64-1.60 (2H, m), 1.57- 1.52 (4H, m), 1.40 (9H, s), 1.31-1.27 (24H, m), 0.88 (3H, t, J=7.0Hz)

[0117] Example 9 The same procedure as in Example 8 was conducted except that 2,6-di-tert-butyl-4-(3-hydroxypropyl)phenol was used as the raw material, to obtain 4.67 g of a phenolic compound A-9 represented by formula (A-9) in a yield of 66.7% and a purity of 91.6%.

[0118] １ H-NMR (CDCl ３ , 400MHz): δ: 6.97 (2H, s), 5.05 (1H, s), 4.10 (2H, t, J = 6.6Hz), 3.38 (4H, t, J = 6.7Hz), 2.60-2.58 (2H, m), 2.31 (2H, t, J=7.6Hz), 1.93-1.91 (2H, m), 1.63-1.57 (7H, m), 1.43 (18H, s), 1.34-1.28 (23H, m), 0.88 (3H, t, J=6.8Hz)

[0119] Example 10 The same procedure as in Example 8 was conducted except that a crude product of 3,7,11,15-tetramethylhexadecanoic acid was used as the raw material, to obtain 3.17 g of a phenolic compound A-10 represented by formula (A-10) in a yield of 73.7% and a purity of 99.1%.

[0120] １ H-NMR (CDCl ３, 400MHz): δ: 6.93 (1H, d, J = 2.1Hz), 6.81 (1H, d, J = 2.0Hz), 4.63 (1H, s), 4.09 (2H, t, J = 6.5Hz), 2.57 (2H, t, J = 7.6Hz), 2.34-2.29 (1H , m), 2.22 (3H, s), 2.14-2.09 (1H, m), 1.93-1.90 (2H, m), 1.40-1.05 (31H, m), 0.95 (3H, d, J = 6.6Hz), 0.85 (12H, t, J = 7.0Hz)

[0121] Example 11 The same procedure as in Example 10 was conducted except that 2,6-di-tert-butyl-4-(3-hydroxypropyl)phenol was used as the raw material, to obtain 4.24 g of a phenolic compound A-11 represented by formula (A-11) in a yield of 90.5% and a purity of 99.2%.

[0122] １ H-NMR (CDCl ３ , 400MHz): δ: 6.97 (2H, s), 5.04 (1H, s), 4.11 (2H, t, J = 6.5Hz), 2.61-2.58 (2H, m), 2.35-2.30 (1H, m), 2.14-2 .09 (1H, m), 1.95-1.88 (2H, m), 1.34-1.17 (40H, m), 0.95 (3H, d, J = 6.6Hz), 0.85 (12H, t, J = 7.1Hz)

[0123] Example 12 The same procedure as in Example 8 was conducted except that a crude product of 2-octyldodecanoic acid was used as the raw material, to obtain 6.52 g of a phenolic compound A-12 represented by formula (A-12) in a yield of 78.8% and a purity of 99.0%.

[0124] １ H-NMR (CDCl ３, 400MHz): δ: 6.93 (1H, d, J = 2.2Hz), 6.81 (1H, d, J = 2.0Hz), 4.65 (1H, s), 4.10 (2H, t, J = 6.6Hz), 2.57 (2H, t, J = 7.8Hz), 2 .36-2.32 (1H, m), 2.22 (3H, s), 1.92-1.89 (2H, m), 1.64-1.56 (2H, m), 1.46-1.41 (11H, m), 1.27-1.25 (28H, br m), 0.88-0.86 (6H, m)

[0125] Example 13 The same procedure as in Example 12 was conducted except that 2,6-di-tert-butyl-4-(3-hydroxypropyl)phenol was used as the raw material, to obtain 3.81 g of a phenolic compound A-13 represented by formula (A-13), in a yield of 76.1% and with a purity of 99.6%.

[0126] １ H-NMR (CDCl ３ , 400MHz): δ: 6.97 (2H, s), 5.04 (1H, s), 4.12 (2H, t, J = 6.5Hz), 2.61-2.58 (2H, m), 2.36-2 .33 (1H, m), 1.94-1.90 (2H, m), 1.65-1.58 (2H, m), 1.40 (18H, s), 1.31 (30H, br s), 0.89-0.84 (6H, m)

[0127] Comparative Example 1 As the phenolic compound A-14, a commercially available product, Irganox 1076 (manufactured by BASF) having a structure represented by formula (A-14), was used.

[0128] [Conditions for analyzing the purity of phenolic compounds] The purity of the phenolic compounds obtained in the examples was measured under the following conditions. Purity (LC) Model: LC-20A Column: SUMIPAX ODS A-212 (5 μm, 6 mmφ, 150 mm) Injection volume: 5 μL (each methanol / chloroform = 1 / 1 (v / v) solution) Mobile phase: Solution A water / ammonium acetate = 1000 / 1 (v / v) Solution B methanol / ammonium acetate = 1000 / 1 (v / v) Gradient: B conc. (%) 80% → (20 min) → 100% → (30 min) → 100% Flow rate: 1.0 mL / min Column temperature: 40°C Measurement wavelength: UV, 280 nm

[0129] Structural analysis of the phenolic compounds obtained in the examples ( １ H-NMR measurement was carried out under the following conditions: Apparatus: Varian 400MR (Agilent)

[0130] [Properties at 30°C] The phenolic compounds of the Examples and Comparative Examples were allowed to stand overnight in a glass container in an environment at a temperature of 25 to 30°C. Thereafter, the properties of each compound were visually confirmed and evaluated according to the following criteria. As a result, phenolic compounds A-1 to A-13 were liquid, and phenolic compound A-14 was solid. Evaluation criteria for properties: ◯: liquid, ×: solid

[0131] [Evaluation of stability over time of composition] 1 part by mass of the phenolic compound of Examples 1 to 13 or Comparative Example 1 and 2 parts by mass of a phosphite compound (WESTON (registered trademark) 705, manufactured by SI GROUP) were mixed in a glass container, immersed in a water bath heated to 60°C, and stirred until a uniform liquid was formed. The resulting liquid mixture was left to stand overnight in an environment with an air temperature of 25 to 30°C. Thereafter, the uniformity of the liquid mixture was visually confirmed and evaluated according to the following criteria. The results are shown in Table 1. Evaluation criteria for uniformity ◯: Liquid that maintained uniformity ×: Liquid with precipitates XX: Solidified

[0132] Example 14 100 parts by mass of low-density polyethylene resin (LLDPE) (linear low-density polyethylene manufactured by Sumitomo Chemical Co., Ltd. (melt flow rate (MFR) at a temperature of 190°C and a load of 21.18N: 1 g / 10 min)), 0.05 parts by mass of calcium stearate (manufactured by Nitto Kasei Kogyo Co., Ltd.), and 1 part by mass of the phenolic compound A-1 obtained in Example 1 were dry-blended, and the resulting mixture was kneaded using a small kneader (MC15HT, Xplore Instruments) at a temperature of 190°C and a screw rotation speed of 30 rpm to obtain pellets of organic material composition 1.

[0133] [Examples 15 to 26, Comparative Example 1] Pellets of organic material compositions 2 to 14 were obtained in the same manner as in Example 14, except that phenolic compounds A-2 to A-13 obtained in Examples 2 to 13 or phenolic compound A-14 of Comparative Example 1 were used instead of phenolic compound A-1 obtained in Example 1.

[0134] [Evaluation of Bleeding Resistance] <Preparation of Test Pieces> The pellets of the organic material compositions obtained in Examples 15 to 26 and Comparative Example 1 were pressed using a press ("PEW-5040" manufactured by Kansai Roll Co., Ltd.) at a temperature of 190°C to obtain a sheet having a thickness of 1 mm. The obtained sheet was cut into a length of 4 cm and a width of 6 cm using a lever-type sample cutter ("SDL-200" manufactured by Dumbbell Co., Ltd.) to obtain test pieces.

[0135] <Test Method> Low-density polyethylene resin (LLDPE) was pressed using a press ("PEW-5040" manufactured by Kansai Roll Co., Ltd.) at a temperature of 190°C to obtain a sheet with a thickness of 0.1 mm. The obtained sheet was cut into a length of 12 cm and a width of 12 cm using a lever-type sample cutter ("SDL-200" manufactured by Dumbbell Co., Ltd.) to obtain an additive-free film strip. Two test pieces of each were lined up, sandwiched between the two additive-free film strips from above and below, and pressed together using a roll. This was then sandwiched between two aluminum plates, a 2 kg weight was placed on top, and the strip was aged in a 60°C oven for two weeks. The test piece was then peeled off, and the aged additive-free film strip was removed.

[0136] <Analysis Method> The removed additive-free film pieces were cut into approximately 5 mm squares, and the entire amount (approximately 4 g) of additive-free film pieces was precisely weighed and subjected to Soxhlet extraction using 110 mL of chloroform for 10 hours. The extract was concentrated using an evaporator, and the concentrate was adjusted to a constant volume of 10 mL with chloroform and methanol to prepare a sample solution. LC measurement was performed on the sample solution under the following conditions, and the amount of each phenolic compound component that had migrated from each test piece to the additive-free film was quantified.

[0137] <LC analysis conditions> Column: SUMIPAX ODS A-212 6 mmφ×150 mm (5 μm) Mobile phase: Solution A; 0.1% ammonium acetate added / distilled water Solution B: 0.1% ammonium acetate added / methanol Elution conditions: Solution B concentration; 80% → (1% / min) → 100% (30 min) Flow rate: 1.0 mL / min Column temperature: 40°C Detection wavelength: 280 nm Injection volume: 5 μL

[0138] <Method for evaluating bleeding resistance> The quantitative value of each phenolic compound component that migrated from each test piece to the additive-free film was converted into a percentage (%) based on the quantitative value of Comparative Example 1. A lower value means better bleeding resistance. The obtained results were evaluated according to the following criteria. The obtained results are shown in Table 1. ◯: Less than 110% ×: 110% or more

[0139] [Overall Evaluation] Based on the above-mentioned evaluation results of properties, uniformity evaluation, and bleeding resistance, each phenolic compound was evaluated according to the following criteria. The results are shown in Table 1. ⊚: Properties and uniformity evaluation at 30°C are rated as ◯, and bleeding resistance is ◯. ◯: Properties and uniformity evaluation at 30°C are ◯, but bleeding resistance is ×. ×: At least one of the properties and uniformity evaluation at 30°C is ×.

[0140]

Claims

1. Formula (I): [In formula (I), R １ and R ２ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a cycloalkyl group having 5 to 8 carbon atoms, X represents a linear or branched alkylene group having 1 to 3 carbon atoms, Y represents *-C(=O)-O-**, *-O-C(=O)-**, *-O-**, or *-O-C(=O)-O-**, * represents a bond to X, and ** represents a bond to Z, and Z is represented by formula (z1): [In formula (z1), A represents a linear or branched alkylene group having 1 to 20 carbon atoms, provided that when Y represents *-C(=O)-O-**, the alkylene group has 4 to 20 carbon atoms, B represents a linear or branched alkylene group having 2 to 3 carbon atoms, n represents an integer of 0 to 5, and R ３ represents a linear or branched alkyl group having 1 to 20 carbon atoms, and *** represents a bond to Y, or a branched, saturated or unsaturated hydrocarbon group (z2) having 9 to 24 carbon atoms, provided that when Y represents *-C(=O)-O-**, the hydrocarbon group (z2) is represented by the formula (z2'): [In formula (z2'), m represents an integer of 1 to 3, and D represents -CH ２ -CH ２ -CH(-CH ３ ) -, -CH ２ -CH=C(-CH ３ ) -, -CH ２ -CH(-CH ３ ) - or -CH=C(-CH ３ )-, and *** represents a bond to Y.

2. The phenolic compound according to claim 1, wherein Y in formula (I) represents *-C(=O)-O-** or *-O-C(=O)-**, and Z is a group represented by formula (z1).

3. The phenolic compound according to claim 1, wherein Y in formula (I) represents *-O-C(=O)-**, and Z represents a branched, saturated or unsaturated hydrocarbon group having 9 to 24 carbon atoms.

4. The phenolic compound according to claim 1, wherein Y in formula (I) represents *-C(=O)-O-**, and Z is a group represented by formula (z2').

5. A stabilizer comprising the phenolic compound according to any one of claims 1 to 4.

6. The stabilizer according to claim 5, which is an antioxidant, anti-aging agent, and / or processing stabilizer.

7. An organic material composition comprising the phenolic compound according to any one of claims 1 to 4 or the stabilizer according to claim 5 or 6, and at least one organic material.

8. The organic material composition according to claim 7, wherein the organic material is a thermoplastic resin.

9. The organic material composition according to claim 8, wherein the thermoplastic resin is a polyolefin or an engineering plastic.

10. A method for stabilizing an organic material, which comprises adding a phenolic compound according to any one of claims 1 to 4 or a stabilizer according to claim 5 or 6 to the organic material.

11. The stabilization method according to claim 10, wherein the organic material is a thermoplastic resin.

12. The stabilization method according to claim 11, wherein the thermoplastic resin is a polyolefin or an engineering plastic.

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