Composition, organic material composition, and method for stabilizing organic material

Abstract

To provide a composition comprising a phenolic compound and a phosphorus compound, capable of providing an organic material composition having excellent antioxidant properties, especially antioxidant properties in an oxygen atmosphere, even after prolonged storage.SOLUTION: There is provided a composition comprising a phenolic compound represented by formula (I): [R1 and R2 represent H, an alkyl group, or the like; R3 and R4 represent hydrocarbon groups; and X represents an alkylene group], and a phosphorus compound having a molecular weight of 550 or more.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a composition, an organic material composition, and a method for stabilizing an organic material. [Background technology]

[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 interior and exterior parts in automotive applications such as bumpers, instrument panels, door trims, and pillars; parts for home appliances such as vacuum cleaners and televisions; 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 can deteriorate due to the action of heat, oxygen, and the like, resulting in a decrease in the strength properties of the organic material, changes in flowability, coloration, and deterioration in surface properties due to phenomena such as molecular scission and molecular crosslinking, and can significantly impair the commercial value of the products.

[0003] In order to prevent deterioration of such resin compositions due to the effects of heat, oxygen, etc., a phenolic compound and a phosphorus-based compound are added in combination. For example, Patent Document 1 describes a method for stabilizing polyether polyol, polyester polyol, and polyurethane by adding a phenolic compound and a specific phosphorus-based compound. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Patent No. 5042630 specification Summary of the Invention [Problem to be solved by the invention]

[0005] It is known that when a phenolic compound and a phosphorus compound are used in combination, the interaction between the phenolic compound and the phosphorus compound can improve the antioxidant performance depending on the combination, but the antioxidant performance can decrease after long-term storage. Furthermore, when these compounds are added to organic materials, particularly polyolefins, the antioxidant performance can decrease after long-term storage.

[0006] Therefore, an object of the present invention is to provide a composition containing a phenolic compound and a phosphorus-based compound, which can provide an organic material composition that has excellent antioxidant performance, particularly excellent antioxidant performance in the presence of oxygen, even after long-term storage. [Means for solving the problem]

[0007] The present inventors have conducted extensive research to solve the above-mentioned problems, and as a result have found that the above-mentioned problems can be solved when a specific phenolic compound and a phosphorus-based compound are used in combination, thereby completing the present invention.

[0008] That is, the present invention includes the following preferred embodiments. [1] Formula (I): [ka] [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; R 3 and R 4 each independently represents a linear or branched, saturated or unsaturated hydrocarbon group having 2 to 20 carbon atoms, X represents a linear or branched alkylene group having 1 to 3 carbon atoms. and a phosphorus-based compound having a molecular weight of 550 or more. [2] The composition according to [1], wherein the phosphorus-based compound comprises a low-molecular-weight phosphorus-based compound having a molecular weight of 550 or more and 1000 or less, and / or a high-molecular-weight phosphorus-based compound having a molecular weight of 1000 or more. [3] The composition according to [1] or [2], wherein the phosphorus-based compound includes a phosphorus-based compound that is liquid at 30°C. [4] The composition according to any one of [1] to [3], wherein the phosphorus-based compound is solid at 30°C and includes a phosphorus-based compound having a triaryl phosphite structure, a cyclic phosphite ester structure, or a phosphonite structure. [5] The composition according to any one of [1] to [4], wherein the amount of the phenolic compound represented by formula (I) is 0.001 to 90 mass% relative to the total amount of the composition, and the amount of the phosphorus-based compound is 0.001 to 90 mass% relative to the total amount of the composition. [6] The mass W of the phenolic compound represented by formula (I) contained in the composition A The mass W of the phosphorus-based compound B The ratio (W B / W A ) is 10 to 0.1. [7] The composition according to any one of [1] to [6], which is an antioxidant, an antiaging agent, and / or a processing stabilizer. [8] The composition according to any one of [1] to [7], which is a stabilizer for polyolefins. [9] An organic material composition comprising the composition according to any one of [1] to [8] and at least one organic material.

[10] The organic material composition according to [9], wherein the organic material is a thermoplastic resin.

[11] The organic material composition according to

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

[12] A method for stabilizing an organic material, comprising adding the composition according to any one of [1] to [8] to the organic material.

[13] The stabilization method according to

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

[14] The stabilization method according to

[13] , wherein the thermoplastic resin is a polyolefin or an engineering plastic. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide a composition containing a phenolic compound and a phosphorus-based compound, which can provide an organic material composition that has excellent antioxidant performance, particularly excellent antioxidant performance in the presence of oxygen, even after long-term storage. DETAILED DESCRIPTION OF THE INVENTION

[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] (phenolic compounds) The present invention relates to a compound of formula (I): [ka] [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; R 3 and R 4 each independently represents a linear or branched, saturated or unsaturated hydrocarbon group having 2 to 20 carbon atoms, X represents a linear or branched alkylene group having 1 to 3 carbon atoms. and a phosphorus-based compound having a molecular weight of 550 or more.

[0012] In the phenolic compound represented by 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 the alkyl group 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. 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, from the viewpoint of easily improving heat resistance and antioxidant performance, particularly antioxidant performance after long-term storage.

[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. 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, from the viewpoint of easily improving antioxidant performance, particularly antioxidant performance after long-term storage.

[0015] In formula (I), R 3 and R 4 each independently represents a linear or branched, saturated or unsaturated hydrocarbon group having 2 to 20 carbon atoms.

[0016] Among the linear or branched, saturated or unsaturated hydrocarbon groups having 2 to 20 carbon atoms, the saturated hydrocarbon groups having 2 to 20 carbon atoms include linear or branched alkyl groups having 2 to 20 carbon atoms, specifically, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-pentyl, t-pentyl, 2-methylbutyl, 3-methylbutyl, 2-ethylpropyl, and n-hexyl groups. , n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, 2-ethylhexyl group, 2,4-dimethylbutyl group, 1,3-dimethylbutyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, and icosyl group.

[0017] Among linear or branched, saturated or unsaturated hydrocarbon groups having 2 to 20 carbon atoms, the unsaturated hydrocarbon group having 2 to 20 carbon atoms includes the saturated hydrocarbon groups described above in which at least one carbon-carbon single bond (-CC-) is replaced with a double bond (-C=C-). In the case of an unsaturated hydrocarbon group, the number of double bonds contained in the hydrocarbon group is preferably 1 to 9, and more preferably 1 to 5.

[0018] The carbon number of the linear or branched, saturated or unsaturated hydrocarbon group having 2 to 20 carbon atoms is preferably 3 to 20, more preferably 5 to 20, and even more preferably 5 to 15, from the viewpoint of easily improving heat resistance and antioxidant performance, particularly antioxidant performance after long-term storage. 3 and / or R 4 In terms of raw material availability and ease of handling of the phenolic compound, the hydrocarbon group 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.

[0019] In formula (I), X represents a linear or branched alkylene group having 1 to 3 carbon atoms. Examples of the linear or branched alkylene group having 1 to 3 carbon atoms include a methylene group, an ethylene group, a methylmethylene group, a propylene group, and an isopropylene group. 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.

[0020] Specific examples of the compound represented by formula (I) include compounds represented by the following formulae (I-1) to (I-6).

[0021] [ka]

[0022] In a preferred embodiment of the present invention, 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 -80 to 30°C, more preferably -80 to 25°C, and even more preferably -80 to 20°C.

[0023] Method for producing phenolic compounds The method for producing the phenolic compound represented by formula (I) of the present invention is not particularly limited, but it can be synthesized by reacting a carboxylic acid and / or its derivative with an alcohol. Examples of the carboxylic acid derivative include alkyl esters such as methyl carboxylic acid esters and ethyl carboxylic acid esters, and carboxylic acid halides.

[0024] The reaction may be carried out in an organic solvent or without the use of 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 the use of an organic solvent.

[0025] 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.

[0026] In this method, the amounts of the carboxylic acid and / or its derivative and the alcohol used as raw materials are 0.5 to 1.5, preferably 0.8 to 1.2, and more preferably 0.9 to 1.1, relative to 1 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, and preferably 100 to 140°C.

[0027] (phosphorus compounds) The composition of the present invention contains the phenolic compound represented by the above-mentioned formula (I) and a phosphorus-based compound having a molecular weight of at least 550. From the viewpoint of heat resistance, the molecular weight of the phosphorus-based compound is preferably at least 600, more preferably at least 620, and even more preferably at least 640.

[0028] In a preferred embodiment of the present invention, from the viewpoint of ease of handling, the phosphorus-based compound having a molecular weight of 550 or more is preferably liquid at 30°C. The melting point of the phosphorus-based compound is preferably -80 to 30°C, more preferably -80 to 25°C, and even more preferably -80 to 20°C.

[0029] In another preferred embodiment of the present invention, the phosphorus-based compound having a molecular weight of 550 or more may be a phosphorus-based compound containing a triaryl phosphite structure, a cyclic phosphite ester structure, or a phosphonite structure.

[0030] In another preferred embodiment of the present invention, the phosphorus-based compound having a molecular weight of 550 or more may be a phosphorus-based compound that is liquid at 30°C (more preferably a phosphorus-based compound having a triaryl phosphite structure, a cyclic phosphite ester structure, or a phosphonite structure), or may be a phosphorus-based compound that is solid at 30°C and has a triaryl phosphite structure, a cyclic phosphite ester structure, or a phosphonite structure.

[0031] Phosphorus compounds with a molecular weight of 550 or more are divided into low-molecular-weight phosphorus compounds with a molecular weight of 550 or more but less than 10,000, and high-molecular-weight phosphorus compounds with a molecular weight of 10,000 or more. Examples of low molecular weight phosphorus compounds with a molecular weight of 550 or more and less than 10,000 include 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)fluoro 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, tetrakis(2,4-di-t-butylphenyl)-4,4'-diphenylene diphosphonite, and the like.

[0032] An example of a high-molecular-weight phosphorus-based compound having a molecular weight of 10,000 or more is DOVERPHOS LGP-12. From the viewpoint of thermal stability, a high-molecular-weight phosphorus-based compound having a molecular weight of 10,000 or more is preferred, and a liquid high-molecular-weight phosphorus-based compound having a molecular weight of 10,000 or more is more preferred. The molecular weight of a high-molecular-weight phosphorus-based compound may be, for example, a weight-average molecular weight measured by GPC. When measuring the weight-average molecular weight by GPC, the measurement may be performed using a GPC / SEC column for low-molecular-weight resins having a molecular weight of 25,000 or less, preferably a PLgel MIXED E column (manufactured by AGILENT TECHNOLOGY), using an organic solvent, preferably tetrahydrofuran, as the solvent.

[0033] Examples of phosphorus compounds containing a triarylphosphite structure include tris(nonylphenyl)phosphite, tris(2,4-di-t-butylphenyl)phosphite, and WESTON 705.

[0034] Examples of phosphorus compounds containing a cyclic phosphite structure include 6-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-t-butyldibenz[d,f][1,3,2]dioxaphosphepine, 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, 2,2'-methylenebis(4,6-di-t-butylphenyl)2-ethylhexyl phosphite, and 2,2'-ethylidenebis(4,6-di-t-butylphenyl)fluorophosphite.

[0035] An example of a phosphorus-based compound containing a phosphonite structure is tetrakis(2,4-di-t-butylphenyl)-4,4'-diphenylenediphosphonite.

[0036] (composition) The composition of the present invention may contain one type of phenolic compound represented by the above formula (I), or may contain two or more types of phenolic compounds represented by the above formula (I). It may also contain one type of phosphorus-based compound having a molecular weight of 550 or more, or may contain two or more types of phosphorus-based compounds having a molecular weight of 550 or more. It may also contain phenolic compounds other than those mentioned above, phosphorus-based compounds other than those mentioned above, and other components.

[0037] The amount of the phenolic compound represented by formula (I) in the composition is preferably 0.001 to 90 mass%, more preferably 0.01 to 30 mass%, and even more preferably 0.01 to 10 mass%, relative to the total amount of the composition, from the viewpoint of antioxidant properties after long-term storage of the composition.

[0038] The amount of the phosphorus-based compound is preferably 0.001 to 90 mass %, more preferably 0.01 to 30 mass %, and even more preferably 0.01 to 10 mass %, relative to the total amount of the composition, from the viewpoint of antioxidant properties after long-term storage of the composition.

[0039] The mass W of the phenolic compound represented by formula (I) contained in the composition A The mass W of the phosphorus-based compound B The ratio (W B / W A ) is preferably 10 to 0.1, more preferably 5 to 0.5, and even more preferably 3 to 0.5, from the viewpoint of antioxidant properties of the composition after long-term storage.

[0040] (stabilizer) The composition of the present invention, which contains a phenolic compound represented by formula (I) and a phosphorus-based compound having a molecular weight of 550 or more, is a compound that can act as a stabilizer (preferably an antioxidant, antiaging agent, and / or processing stabilizer) for resins. The present invention also provides a stabilizer, preferably an antioxidant, antiaging agent, and / or processing stabilizer, which is a composition containing the above-mentioned phenolic compound and a phosphorus-based compound having a molecular weight of 550 or more. Furthermore, the composition of the present invention is more preferably a stabilizer for polyolefins.

[0041] By adding the composition of the present invention to an organic material such as a thermoplastic resin, thermal degradation, oxidative degradation, etc. 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 antioxidant 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.

[0042] Adding the composition of the present invention to an organic material such as a thermoplastic resin can reduce thermal and oxidative degradation of the organic material and stabilize the organic material, preventing, for example, viscosity loss and discoloration during processing. It can also prevent resin deterioration over time. The composition may be a material containing only the phenolic compound represented by formula (I) above and a phosphorus-based compound having a molecular weight of 550 or more, or it may be a material containing these compounds and at least one other additive that can be contained in the resin composition described below. The composition of the present invention may also be a material containing at least one organic material in addition to the above compounds. Such a material is also referred to as a masterbatch, for example.

[0043] [Organic material composition and method for stabilizing organic material] Adding the composition of the present invention to an organic material can reduce thermal degradation, oxidative degradation, and the like of the organic material, thereby stabilizing the organic material. For example, it is believed that viscosity loss and coloration can be prevented. Furthermore, it can also prevent deterioration over time after processing of resins. The composition of the present invention is suitable as a stabilizer for organic materials. In particular, when the organic material is a thermoplastic resin, particularly a polyolefin, it has been found that, compared to conventional stabilizer combinations, the composition of the present invention can suppress the decline in antioxidant performance, particularly the decline in antioxidant performance in the presence of oxygen, even after long-term storage of the organic material to which the stabilizer has been added.

[0044] In addition to the composition containing the phenolic compound represented by formula (I) and a phosphorus-based compound having a molecular weight of 550 or greater, the present invention also provides an organic material composition containing the composition and at least one organic material, and a method for stabilizing an organic material by adding the composition to an organic material. An organic material composition containing the composition of the present invention and at least one organic material can be said to contain the composition of the present invention as long as it contains the phenolic compound represented by formula (I) and the phosphorus-based compound having a molecular weight of 550 or greater. It can be said to be an organic material composition containing the composition of the present invention and at least one organic material, whether these compounds are added separately or simultaneously as a composition. Furthermore, with regard to the method for stabilizing an organic material by adding the composition of the present invention to an organic material, it can be said to have added the composition of the present invention, whether these compounds are added separately or simultaneously as a composition, as long as the phenolic compound and the phosphorus-based compound having a molecular weight of 550 or greater are added to the organic material.

[0045] Examples of organic materials that can be stabilized by the composition 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 polymers, (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) Fluorine resin, (16) Polyacetal, (17) Grafted polyphenylene ether resins and polyphenylene sulfide resins, (18) polyurethane, (19) Polyamide resins, such as aliphatic polyamides, semi-aromatic polyamides, fully aromatic polyamides, (20) Polyester resins, such as polyethylene terephthalate and polybutylene terephthalate;

[0048] (21) polycarbonate, (22) polyacrylate, (23) Polysulfone, polyetheretherketone, polyethersulfone, (24) Thermoplastic resins such as aromatic polyester resins, (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 resins such as urea resins,

[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 paints, (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 paint, (52) wax, (53) Lubricants, etc.

[0051] Among these, it is preferably used for 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, and is particularly preferably used for polyolefins.

[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 substrates such as magnesium chloride, titanium chloride, alumina, and silicon oxide. Preferred polyolefins are those produced using, for example, Ziegler-Natta catalysts, TNZ catalysts, metallocene catalysts, and Phillips catalysts.

[0053] Engineering plastics are also not particularly limited. Polyamide resins, such as aliphatic polyamides, semi-aromatic polyamides, and fully aromatic polyamides, are not limited 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 condensation reactions between diamines and dicarboxylic acids, condensation reactions between aminocarboxylic acids, and 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 composition of the present invention to an organic material, the organic material can be stabilized.

[0055] When the composition of the present invention is added to an organic material to stabilize it, it is preferable to add the composition of the present invention so that the content of the phenolic compound represented by formula (I) per 100 parts by mass of the organic material is within the following range. From the viewpoint of stabilizing 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. Furthermore, from the viewpoint of stabilizing the organic material and economical reasons, 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.

[0056] When the composition of the present invention is added to an organic material, other additives may be added to the organic material as needed, such as phenolic antioxidants (those not included in formula (I)), sulfur-based antioxidants, ultraviolet absorbers, light stabilizers, peroxide scavengers, polyamide stabilizers, hydroxyamines, lubricants, plasticizers, flame retardants, nucleating agents, metal deactivators, antistatic agents, pigments, fillers, pigments, antiblocking agents, surfactants, processing aids, foaming agents, emulsifiers, brighteners, calcium stearate, hydrotalcite, and the like. Other additives may also be added, such as color stabilizers, such as 9,10-dihydro-9-oxa-10-phosphophenanthrene-10-oxide, and color improvers such as benzofurans and indolines, as described in U.S. Patent Nos. 4,325,853, 4,338,244, 5,175,312, 5,216,053, 5,252,643, 4,316,611, DE-A-4,316,622, 4,316,876, EP-A-589,839, and EP-A-591,102. These additives may be added to the organic material simultaneously with the composition of the present invention, or may be added to the organic material at a different stage from the composition of the present invention. A single additive may be used, or two or more 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 hydroquinone 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, etc.

[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 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 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 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 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 the following: Dilauryl 3,3'-thiodipropionate, tridecyl 3,3'-thiodipropionate, dimyristyl 3,3'-thiodipropionate, distearyl 3,3'-thiodipropionate, lauryl stearyl 3,3'-thiodipropionate, neopentanetetrayltetrakis (3-laurylthiopropionate), etc.

[0067] Examples of ultraviolet absorbents include the following: As the ultraviolet absorbent, 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 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.

[0068] (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] Mixture of 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, 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 product of poly(3-11)(ethylene glycol) with 2-[3'-t-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl]benzotriazole, condensation product of poly(3-11)(ethylene glycol) with 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.

[0069] Examples of light stabilizers include the following: As the light stabilizer, 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,

[0070] 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 esters of dimethyl succinate and 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine, 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)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-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 their mixtures, etc.

[0071] (2) Examples of acrylate light stabilizers 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 Nickel complex of 2,2'-thiobis-[4-(1,1,3,3-tetramethylbutyl)phenol], nickel dibutyldithiocarbamate, nickel salts of monoalkyl esters, nickel complex of ketoximes, and mixtures thereof.

[0072] (4) Examples of oxamide 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 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.

[0073] Examples of metal deactivators include the following: 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)oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide, N,N'-bis(salicyloyl)oxalyl dihydrazide, N,N'-bis(salicyloyl)thiopropionyl dihydrazide, and mixtures thereof.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] 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.

[0080] Examples of nucleating agents include sodium 2,2'-methylenebis(4,6-di-t-butylphenyl)phosphate, [2,2'-methylenebis(4,6-di-t-butylphenyl)]dihydroxyaluminum, bis[2,2'-methylenebis(4,6-di-t-butylphenyl)]hydroxyaluminum, tris[2,2'-methylenebis(4,6-di-t-butylphenyl)]aluminum, sodium Bis(4-t-butylphenyl)phosphate, metal salts of benzoates such as sodium benzoate, aluminum pt-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 1,3-Op-chlorobenzylidene-2,4-O-3,4-dimethylbenzylidene sorbitol, 1,3:2,4-bis(O-3,4-dimethylbenzylidene) sorbitol, 1,3-Op-chlorobenzylidene-2,4-O-3,4-dimethylbenzylidene sorbitol, 1,3-O-3,4-dimethylbenzylidene-2,4-Op-chlorobenzylidene sorbitol, 1,3:2,4-bis(Op-chlorobenzylidene) sorbitol and mixtures thereof.

[0081] Examples of fillers include calcium carbonate, silicates, glass fibers, asbestos, talc, kaolin, mica, barium sulfate, carbon black, carbon fibers, zeolites, and mixtures thereof.

[0082] Among these additives, those preferably used are phenolic antioxidants (those not included in formula (I)), ultraviolet absorbers, hindered amine light stabilizers, peroxide scavengers and neutralizing agents.

[0083] 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,

[0084] 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.

[0085] 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, 2-(5'-t-butyl-2'-hydroxyphenyl)benzotriazo 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, 2-[2'-hydroxy-3',5'-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, and the like.

[0086] 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, 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,

[0087] 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 polymer 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)], etc.

[0088] The composition of the present invention and other optional additives can be added to an organic material using any known method and apparatus for obtaining a homogeneous mixture. For example, in the case of adding a phenolic compound represented by formula (I) and a phosphorus-based compound having a molecular weight of 550 or greater, if the organic material is a solid polymer, these compounds and / or other optional additives can be dry-blended directly with the solid polymer. Alternatively, the phenolic compound represented by formula (I), the phosphorus-based compound having a molecular weight of 550 or greater, and 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 addition methods, the phenolic compound represented by formula (I), the phosphorus-based compound having a molecular weight of 550 or greater, and 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), the phosphorus-based compound having a molecular weight of 550 or more, and other additives added as needed can be added directly to the organic material to dissolve them, or they can be added in a dissolved or suspended state in a liquid medium.

[0089] The composition of the present invention has excellent properties as a stabilizer for various organic materials, including thermoplastic resins such as polyolefins. Organic materials to which the composition of the present invention is added are stable against thermal and oxidative degradation during production, processing, and use, resulting in high-quality products. [Example]

[0090] 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.

[0091] <Ingredients> The components used in the examples and comparative examples are listed below. (thermoplastic resin) 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: 1g / 10min)) (processing stabilizer) ·Compound A-1~4 Compound B-1: Bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite (molecular weight 514, melting point 89-92°C) Compound B-2: TNPP (trisnonylphenyl phosphite, manufactured by Dover Chemical, molecular weight 688, melting point 6°C) Compound B-3: A phosphite compound (liquid, weight-average molecular weight 13,957) synthesized with reference to Example 2 of U.S. Pat. No. 8,981,042. Compound B-4: WESTON 705 (manufactured by SI GROUP, melting point 2°C) Compound B-5: IRGAFOS 168 (tris(2,4-di-tert-butylphenyl)phosphite, manufactured by BASF, molecular weight 647, melting point 183-186°C)

[0092] <Production of Compounds> [Synthesis Example 1] 19.2 g (57.9 mmol) of 2-n-octyl-1-dodecanol, 14.0 g (56.7 mmol) of methyl 3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate, 3.03 g (11.6 mmol) of dibutyltin oxide, and 16.2 mL of toluene were placed in 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 removed each time it accumulated in the Dean-Stark apparatus, and an equal amount of toluene was added to the reaction solution. After the reaction, the toluene was removed by vacuum distillation, and the resulting liquid was purified by silica gel chromatography to obtain 25.0 g of phenolic compound A-1 represented by formula (A-1) in a yield of 85.3% and a purity of 98.6%.

[0093] [ka]

[0094] 1 H-NMR (CDCl3, 400 MHz): δ: 6.99 (2H, s), 5.07 (1H, s), 3.98 (2H, d, J=5.9Hz), 2.87 (2H, t, J=8.1Hz), 2.61-2.59(2H, m), 1.43(18H, s), 1.27-1.25(33H, brm), 0.89-0.87(6H, m)

[0095] [Synthesis Example 2] Phenol compound A-2 represented by formula (A-2) was obtained in an amount of 14.8 g in a yield of 89.3% and a purity of 99.1%, in the same manner as in Synthesis Example 1, except that methyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate was used as the raw material instead of methyl 3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate.

[0096] [ka]

[0097] 1 H-NMR (CDCl3, 400 MHz): δ: 6.95 (1H, d, J=2.2Hz), 6.83 (1H, d, J=1.7Hz), 4.65 (1H, s), 3.97 (2H, d, J=5.9Hz), 2.84 (2H, t, J=7 .8Hz), 2.58(2H, m), 2.21(3H, s), 1.61(1H, brs), 1.40(9H, s), 1.26(32H, brs), 0.88(6H, t, J=6.8Hz)

[0098] [Synthesis Example 3] The same procedure as in Synthesis Example 1 was carried out except that 2-hexyl-1-decanol was used as the raw material instead of 2-n-octyl-1-dodecanol, to obtain 5.06 g of phenol compound A-3 represented by formula (A-3) in a yield of 85.5% and a purity of 99.3%.

[0099] [ka]

[0100] 1 H-NMR (CDCl3, 400 MHz): δ: 6.99(2H, s), 5.06(1H, s), 3.98(2H, d, J=5.9Hz), 2.88-2.86(2H, m), 2.61-2.59(2H, m), 1.43(18H, brs), 1.26(25H, brs), 0.88-0.87(6H, m)

[0101] [Synthesis Example 4] The same procedure as in Synthesis Example 1 was carried out except that 2-decyl-1-tetradecanol was used as the raw material instead of 2-n-octyl-1-dodecanol, to obtain 5.88 g of phenol compound A-4 represented by formula (A-4) in a yield of 86.2% and a purity of 99.5%.

[0102] [ka]

[0103] 1 H-NMR (CDCl3, 400 MHz): δ:6.99(2H, s), 5.06(1H, s), 3.98(2H, d, J=5.9Hz), 2.88-2.86(2H, m), 2.6 1-2.59(2H, m), 1.44-1.43(18H, m), 1.30-1.27(41H, m), 0.89-0.86(6H, m)

[0104] [Synthesis Example 5] 13.7 g (62.2 mmol) of 2,4-di-tert-butyl-6-methylphenol, 0.07 g of dimethylformamide, and 3 mL of toluene were placed in a four-neck flask and heated to 55 °C under a nitrogen atmosphere. 4.71 g (34.3 mmol) of phosphorus trichloride was added dropwise, heated to 120 °C, and stirred for 1 hour. The system was then reduced in pressure to 500 hPa to remove excess phosphorus trichloride. 30 mL of toluene was added, and 4.09 g (40.4 mmol) of triethylamine and 2.15 g (46.6 mmol) of ethanol were added dropwise under ice cooling. The mixture was then warmed to room temperature and stirred overnight. The precipitated salt was filtered to obtain a toluene solution. The toluene was then removed by vacuum distillation, and the resulting crude product was purified by silica gel chromatography to obtain 10.1 g of compound B-1 represented by formula (B-1) in a 63.1% yield and 99.3% purity.

[0105] [ka]

[0106] 1 H-NMR (CDCl3, 400 MHz): δ:7.23(2H, d, J=13.0Hz), 7.02(2H, d, J=25.9Hz), 3.95-3.66(2H, m), 2.39(6H , d, J=98.8Hz), 1.49-1.43(18H, m), 1.34-1.27(18H, m), 0.94(3H, t, J=22.3Hz)

[0107] [Conditions for analyzing the purity of phenolic compounds] The purity of the phenol compounds obtained in the synthesis examples was measured under the following conditions. Purity (LC) Model: LC-20A Column: SUMIPAX ODS A-212 (5 μm, 6 mm diameter, 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 concentration (%) 80% → (20 min) → 100% → (30 min) → 100% Flow rate: 1.0mL / min Column temperature: 40℃ Measurement wavelength: UV, 280nm

[0108] Structural analysis of the phenolic compounds obtained in the synthesis examples ( 1 H-NMR measurement was carried out under the following conditions. Equipment: Varian 400MR (Agilent)

[0109] Example 1 100 parts of LLDPE, 0.05 parts of calcium stearate (manufactured by Nitto Kasei Kogyo Co., Ltd.), 0.05 parts of compound A-1, and 0.05 parts of compound B-2 were dry-blended, and the resulting mixture was kneaded in a twin-screw extruder (BTN-32, PLABOR Corporation) with a cylinder diameter of 32 mm under conditions of a temperature of 190°C and a screw rotation speed of 80 rpm in a nitrogen atmosphere to obtain pellets.

[0110] (Examples 2 to 9, Comparative Examples 1 and 2) Pellets were obtained in the same manner as in Example 1, except that compound A or compound B shown in Table 1 was dry blended.

[0111] (antioxidant performance) The oxidation induction time (OIT) of the pellets obtained in the examples and comparative examples was measured using a Hitachi High-Tech Science DSC7020. A 2 mg pellet sample was heated to 200°C at a rate of 50°C / min in a nitrogen atmosphere, and then switched to an oxygen atmosphere while maintained at 200°C. The OIT [minutes] was the time from switching to the oxygen atmosphere until the rise of the exothermic peak. The results are shown in Table 1.

[0112] (Anti-oxidation performance after aging treatment) The pellets obtained in the examples and comparative examples were stored in a thermo-hygrostat chamber at a temperature of 50°C and a humidity of 80%, and then aged for the period (2 weeks or 3 weeks) listed in Table 1. Approximately 0.3 g of pellets were removed from the thermo-hygrostat chamber and weighed, and allowed to stand in a glass container containing 10 mL of toluene for 30 minutes. The pellets were removed from the solvent and dried in a vacuum dryer for 1 hour, after which the OIT [min] was measured using the method described above. Based on the obtained OIT, the initial value and the retention rate after aging were calculated using the following formula. (Retention rate)[%]=(OIT after aging) / (Initial OIT)×100 A larger retention rate indicates better antioxidant performance after long-term storage. The antioxidant performance was evaluated according to the following criteria, and the results are shown in Table 1.

[0113] (Evaluation criteria for antioxidant performance after aging treatment) ○: Retention rate 45% or more ×: retention rate less than 45%

[0114] [Table 1]

Claims

1. Formula (I): 【Chemistry 1】 [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, R ３ and R ４ each independently represents a linear or branched, saturated or unsaturated hydrocarbon group having 2 to 20 carbon atoms, X represents a linear or branched alkylene group having 1 to 3 carbon atoms. and a phosphorus-based compound having a molecular weight of 550 or more.

2. The composition according to claim 1 , wherein the phosphorus-based compound comprises a low-molecular-weight phosphorus-based compound having a molecular weight of 550 or more but less than 10,000, and / or a high-molecular-weight phosphorus-based compound having a molecular weight of 10,000 or more.

3. The composition according to claim 1 , wherein the phosphorus-based compound comprises a phosphorus-based compound that is liquid at 30° C.

4. The composition according to claim 1 , wherein the phosphorus-based compound is a phosphorus-based compound that is solid at 30° C. and has a triaryl phosphite structure, a cyclic phosphite ester structure, or a phosphonite structure.

5. The composition according to claim 1, wherein the amount of the phenolic compound represented by formula (I) is 0.001 to 90% by mass, based on the total amount of the composition, and the amount of the phosphorus-based compound is 0.001 to 90% by mass, based on the total amount of the composition.

6. The mass W of the phenolic compound represented by formula (I) contained in the composition Ａ The mass W of the phosphorus-based compound relative to Ｂ The ratio (W Ｂ / W Ａ 2. The composition of claim 1, wherein β is 10 to 0.

1.

7. The composition of claim 1 which is an antioxidant, anti-aging agent, and / or processing stabilizer.

8. 10. The composition of claim 1 which is a stabilizer for polyolefins.

9. An organic material composition comprising the composition according to any one of claims 1 to 8 and at least one organic material.

10. The organic material composition according to claim 9 , wherein the organic material is a thermoplastic resin.

11. The organic material composition according to claim 10, wherein the thermoplastic resin is a polyolefin or an engineering plastic.

12. A method for stabilizing an organic material, comprising adding the composition according to any one of claims 1 to 8 to the organic material.

13. 13. The stabilization method according to claim 12, wherein the organic material is a thermoplastic resin.

14. 14. The stabilization method of claim 13, wherein the thermoplastic resin is a polyolefin or an engineering plastic.

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