Diphosphite-based compound, method for producing same, and uses of same

Abstract

To provide a compound that can be used for processing of an organic material requiring a high processing temperature, and that has high heat resistance.SOLUTION: A diphosphite-based compound represented by formula (I) [wherein R1 and R2 represent an alkyl group having 1-12 carbon atoms, a cycloalkyl group having 5-8 carbon atoms, an alkylcycloalkyl group having 6-12 carbon atoms, or the like; R3 represents H, an alkyl group having 1-12 carbon atoms, a cycloalkyl group having 5-8 carbon atoms, an alkylcycloalkyl group having 6-12 carbon atoms, or an aralkyl group having 7-25 carbon atoms; and X represents a single bond, an alkylidene group having 1-4 carbon atoms, S, or O].SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a novel diphosphite compound, a method for producing the same, and its use as a stabilizer for organic materials. [Background technology]

[0002] Diphosphite compounds are disclosed in Patent Documents 1 and 2. Patent Document 1 describes that the compounds stabilize organic polymers. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 57-122093 [Patent Document 2] Chinese Patent Application Publication No. 111320653 Summary of the Invention [Problem to be solved by the invention]

[0004] Organic materials such as thermoplastic resins, thermosetting resins, natural or synthetic rubber, mineral oil, lubricating oil, adhesives, and paints are subject to deterioration due to the action of heat, oxygen, and the like during production, processing, and even use, resulting in a decrease in the strength properties of the organic materials due to phenomena such as molecular scission and molecular crosslinking, changes in flowability, coloration, and deterioration in surface properties, which can significantly impair their commercial value. Therefore, it is necessary to prevent such deterioration and stabilize the organic materials, and in the case of organic materials such as engineering plastics, which require even higher processing temperatures than general thermoplastic resins, a stabilizer with high heat resistance is required.

[0005] Therefore, an object of the present invention is to provide a compound having high heat resistance that can be used in processing organic materials that require high processing temperatures. [Means for solving the problem]

[0006] The present inventors have conducted extensive research to solve the above problems and have completed the present invention. That is, the present invention includes the following preferred embodiments.

[0007] [1] Formula (I): [ka] [In formula (I), R 1 represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 25 carbon atoms, R 2 represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, R 3 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 25 carbon atoms, X represents a single bond, an alkylidene group having 1 to 4 carbon atoms, a sulfur atom, or an oxygen atom. A diphosphite compound represented by the formula: [2] R 1 is a tertiary alkyl group having 4 to 12 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or a tertiary aralkyl group having 9 to 15 carbon atoms. [3] The compound of formula (I) above is represented by formula (I'): [ka] [In formula (I'), R 1 , R 2 , R 3 and X is as defined above. The compound according to [1] or [2], wherein the compound is a compound represented by the formula: [4] The compound according to any one of [1] to [3], wherein X is a single bond. [5] R 3is a tertiary alkyl group having 4 to 12 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or a tertiary aralkyl group having 9 to 21 carbon atoms. [6] R 3 The compound according to [5], wherein R is a tertiary alkyl group having 5 to 10 carbon atoms. [7] Formula (II): [ka] [In formula (II), R 1 is as defined above] and a phosphorus trihalide, the reaction product of which is a compound represented by the formula (III): [ka] [In formula (III), R 2 , R 3 and X is as defined above. The method for producing the compound according to any one of [1] to [6], further comprising reacting a compound represented by the formula: [8] A stabilizer for organic materials, comprising the compound according to any one of [1] to [6]. [9] The stabilizer according to [8], wherein the organic material is a thermoplastic resin.

[10] The stabilizer according to [9], wherein the thermoplastic resin is a polyolefin or an engineering plastic.

[11] A method for stabilizing an organic material, comprising adding the compound according to any one of [1] to [6] to the organic material.

[12] An organic material composition comprising an organic material and the compound according to any one of [1] to [6].

[13] The composition according to

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

[14] The composition according to

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

[0008] According to the present invention, it is possible to provide a highly heat-resistant compound that can be used in processing organic materials that require high processing temperatures. DETAILED DESCRIPTION OF THE INVENTION

[0009] 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 here, and various modifications can be made without departing from the spirit of the present invention.

[0010] The present invention relates to a compound of formula (I): [ka] The present invention provides a diphosphite compound represented by the formula:

[0011] In the above formula (I), R 1 represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms; R 2 represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms; R 3 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 25 carbon atoms.

[0012] Examples of alkyl groups having 1 to 12 carbon atoms include, but are not limited to, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, a tert-pentyl group, an n-hexyl group, an i-hexyl group, an n-octyl group, an i-octyl group, a tert-octyl group, an i-nonyl group, a tert-nonyl group, a 2-ethylhexyl group, a 1,1-diethylpropyl group, a 1,2-dimethylpropyl group, a 1,2-diethylpropyl group, and a 1-ethyl-1-methylpropyl group.

[0013] Examples of the cycloalkyl group having 5 to 8 carbon atoms include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a norbornyl group.

[0014] Examples of the alkylcycloalkyl group having 6 to 12 carbon atoms include a 1-methylcyclopentyl group, a 1-methylcyclohexyl group, and a 1-methyl-4-i-propylcyclohexyl group.

[0015] Examples of the aralkyl group having 7 to 25 carbon atoms include a benzyl group, an α-methylbenzyl group, a cumyl group (α,α-dimethylbenzyl group), a phenylethyl group, a phenylpropyl group, an α,α-dimethyl-4-phenylbenzyl group, and an α,α-dimethyl-2,4-di-tert-butylphenylbenzyl group.

[0016] In a preferred embodiment of the invention, the compound of formula (I) has the formula (I'): [ka] [In formula (I'), R 1 , R 2 , R 3 and X is as defined above. That is, one R 1 The other R 1 The meta position relative to the group is preferred from the viewpoint of improving the heat resistance of the diphosphite compound represented by formula (I).

[0017] In one preferred embodiment of the present invention, R 1 From the viewpoint of improving the heat resistance of the diphosphite compound represented by formula (I), is preferably a tertiary alkyl group having 4 to 12 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or a tertiary aralkyl group having 9 to 15 carbon atoms, more preferably a tertiary alkyl group having 4 to 12 carbon atoms, and even more preferably a tert-butyl group or a tert-pentyl group.

[0018] R 2From the viewpoint of improving the heat resistance of the diphosphite compound represented by formula (I), is preferably an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an alkylcycloalkyl group having 6 to 12 carbon atoms; since the diphosphite compound represented by formula (I) is less susceptible to the effects of hydrolysis, a tertiary alkyl group having 4 to 10 carbon atoms or a tertiary aralkyl group having 9 to 12 carbon atoms is more preferred, and a methyl group, a tert-butyl group, a tert-pentyl group, or a cumyl group is even more preferred.

[0019] R 3 From the viewpoint of improving the heat resistance of the diphosphite compound represented by formula (I), is preferably an alkyl group having 1 to 10 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 25 carbon atoms, more preferably a tertiary alkyl group having 4 to 12 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or a tertiary aralkyl group having 9 to 21 carbon atoms, even more preferably a tertiary alkyl group having 5 to 10 carbon atoms or a tertiary aralkyl group having 9 to 15 carbon atoms, and still more preferably a tert-butyl group, a tert-pentyl group, or a cumyl group.

[0020] In the above formula (I), X represents a single bond, an alkylidene group having 1 to 4 carbon atoms, a sulfur atom, or an oxygen atom. Examples of the alkylidene group having 1 to 4 carbon atoms include a methylene group (-CH2-), an ethylene group (-CH2-CH2-), a 1-methylethylene group (-CH2-CH(CH3)-), a propylidene group (-CH(CH2-CH3)-), an isopropylidene group (-C(CH3)2-), and a butylidene group (-CH(CH2-CH2-CH3)-). From the viewpoint of improving the heat resistance of the diphosphite compound represented by formula (I), X is preferably a single bond, a methylene group, an ethylene group, or a sulfur atom, and more preferably a single bond.

[0021] The diphosphite compound represented by the above formula (I) is, for example, a compound represented by the formula (II): [ka] [In formula (II), R1 is as defined above] and a phosphorus trihalide, the reaction product of which is a compound represented by the formula (III): [ka] [In formula (III), R 2 , R 3 and X is as defined above. The compound can be produced by further reacting a compound represented by the following formula:

[0022] Examples of phosphorus trihalides include phosphorus trichloride, phosphorus tribromide, etc. From the viewpoint of ease of handling, phosphorus trichloride is preferably used.

[0023] The reaction can be accelerated by the coexistence of a dehydrohalogenating agent such as an amine, pyridine, pyrrolidine, or amide, or a hydroxide of an alkali metal or alkaline earth metal. To accelerate the reaction, one type of dehydrohalogenating agent or hydroxide of an alkali metal or alkaline earth metal may be used, or two or more types of these may be used in combination.

[0024] As the amines, any of primary amines, secondary amines, and tertiary amines may be used. Examples of amines include t-butylamine, t-pentylamine, t-hexylamine, t-octylamine, di-t-butylamine, di-t-pentylamine, di-t-hexylamine, di-t-octylamine, trimethylamine, triethylamine, N,N-diisopropylethylamine, N,N-dimethylaniline, and N,N-diethylaniline. As the amines, triethylamine and / or N,N-diisopropylethylamine are preferably used from the viewpoint of facilitating the reaction. Examples of pyridines include pyridine and picoline, with pyridine being preferred. Examples of pyrrolidines include 1-methyl-2-pyrrolidine. Examples of amides include N,N-dimethylformamide and N,N-dimethylacetamide, with N,N-dimethylformamide being preferred.

[0025] Examples of the hydroxide of an alkali metal or alkaline earth metal include sodium hydroxide and calcium hydroxide, with sodium hydroxide being preferred.

[0026] The reaction is usually carried out in an organic solvent. The organic solvent is not particularly limited as long as it does not inhibit the reaction, and examples thereof include aromatic hydrocarbons, aliphatic hydrocarbons, oxygenated hydrocarbons, and halogenated hydrocarbons. The reaction may be carried out in one type of organic solvent, a mixed solvent of two or more types of organic solvents, or a mixed solvent of the organic solvent and another solvent.

[0027] Examples of aromatic hydrocarbons include benzene, toluene, xylene, and ethylbenzene. Examples of aliphatic hydrocarbons include n-hexane, n-heptane, and n-octane. Examples of oxygen-containing hydrocarbons include diethyl ether, dibutyl ether, tetrahydrofuran, and 1,4-dioxane. Examples of halogenated hydrocarbons include chloroform, carbon tetrachloride, monochlorobenzene, dichloromethane, 1,2-dichloroethane, and dichlorobenzene. From the viewpoint of improving the yield, it is preferable to use toluene, xylene, n-hexane, n-heptane, diethyl ether, tetrahydrofuran, 1,4-dioxane, chloroform, or dichloromethane as the organic solvent.

[0028] The reaction method employed is a two-step reaction method in which a compound represented by formula (II) is reacted with phosphorus trihalide, and the resulting reaction product is then reacted with a compound represented by formula (III). In this method, the phosphorus trihalide is preferably used in an amount of about 1.6 to 2.6 times by mole, more preferably about 1.8 to 2.4 times by mole, and even more preferably about 2.0 to 2.2 times by mole, relative to the compound represented by formula (II) in the first reaction step. When a dehydrohalogenating agent is used, the dehydrohalogenating agent is preferably used in an amount of about 0.05 to 5.0 times by mole, more preferably about 1.5 to 4.5 times by mole, and even more preferably about 2.0 to 4.0 times by mole, relative to the compound represented by formula (II).

[0029] The reaction of the compound represented by formula (II) with phosphorus trihalide is typically carried out at a temperature of about -60 to 100°C. The reaction time may typically be about 0.5 to 12 hours. The reaction may be carried out in air or in an inert gas atmosphere such as nitrogen gas or argon gas. However, from the viewpoint of easily suppressing decomposition of the phosphorus trihalide and intermediates, it is preferable to carry out the reaction in an inert gas atmosphere. The reaction may be carried out under normal pressure, elevated pressure, or reduced pressure. It is believed that this reaction produces an intermediate halogenophosphite. The resulting reaction product may be isolated and subjected to the next reaction, but the reaction mixture is typically subjected to the reaction with the compound represented by formula (III) as is.

[0030] The reaction method between the compound represented by formula (II) and the phosphorus trihalide is not particularly limited as long as it allows the two to be mixed uniformly. However, from the viewpoint of easy control of the reaction heat, it is preferable to carry out the reaction by a method in which the phosphorus trihalide is added dropwise to a mixture containing the compound represented by formula (II) and, optionally, a dehydrohalogenating agent, or a method in which the compound represented by formula (II) is added dropwise to a mixture containing the phosphorus trihalide and, optionally, a dehydrohalogenating agent. Furthermore, when a dehydrohalogenating agent is used, the reaction may be carried out by adding the dehydrohalogenating agent dropwise to a mixture containing the compound represented by formula (II) and the phosphorus trihalide. The dropwise addition time is also not particularly limited, and may be, for example, about 0.5 to 3 hours.

[0031] In the subsequent second-stage reaction, the compound represented by formula (III) is typically used in an amount of about 1.5 to 3.5 times by mole relative to the compound represented by formula (II), preferably about 1.7 to 2.8 times by mole, and even more preferably about 1.9 to 2.3 times by mole. A dehydrohalogenating agent can also be used in this reaction. In this case, the amount of dehydrohalogenating agent is preferably about 0.1 to 15 times by mole relative to the compound represented by formula (II) used in the first-stage reaction, more preferably about 4.0 to 13.5 times by mole, and even more preferably about 6.0 to 12.0 times by mole. The amount of dehydrohalogenating agent used in the second-stage reaction is typically calculated as the sum of the amount of dehydrohalogenating agent used in the initial reaction and the amount of additional dehydrohalogenating agent. The reaction with the compound represented by formula (III) is typically carried out at a temperature of about -60 to 100°C. The reaction time may typically be about 1 to 30 hours. The reaction may be carried out in air or in an inert gas atmosphere such as nitrogen gas or argon gas, but is preferably carried out in an inert gas atmosphere from the viewpoint of easily suppressing the generation of by-products. The reaction may be carried out under normal pressure, elevated pressure, or reduced pressure.

[0032] The method for reacting the compound represented by formula (II) with the compound represented by formula (III) is not particularly limited as long as the two can be mixed uniformly, but from the viewpoint of easy control of the reaction heat, it is preferable to carry out the reaction by adding the compound represented by formula (III) dropwise to the reaction product obtained by reacting the compound represented by formula (II) with phosphorus trihalide. The dropwise addition time is also not particularly limited, and may be carried out for, for example, about 10 minutes to 2 hours.

[0033] After the reaction is completed, if a dehydrohalogenating agent has been used, the hydrohalide salt of the dehydrohalogenating agent produced by the reaction is removed, and the solvent is then removed. Thereafter, an appropriate post-treatment such as crystallization or column chromatography is carried out, thereby obtaining the diphosphite compound of the present invention represented by formula (I).

[0034] The compounds represented by formulas (II) and (III) that can be used in the production method of the present invention can be produced by known methods. For example, the compound represented by formula (II) can be produced according to the method described in Chinese Patent Application Publication No. 112341494. The compound represented by formula (III) can be produced according to the method described in Japanese Patent Application Laid-Open No. 2003-171325. If the compounds represented by formulas (II) and (III) are commercially available, they can also be used.

[0035] Examples of the compound represented by formula (II) include resorcinol, 4,6-di-tert-butylresorcinol, 4,6-di-tert-pentylresorcinol, 4,6-di-α-cumylresorcinol, 4,6-dimethylresorcinol, 4,6-diethylresorcinol, and 4,6-di-tert-octylresorcinol.

[0036] Examples of the compound represented by formula (III) include 3,3',5,5'-tetra-tert-butyl-2,2'-dihydroxybiphenyl, 3,3',5,5'-tetra-tert-pentyl-2,2'-dihydroxybiphenyl, 3,3',5,5'-tetra-α-cumyl-2,2'-dihydroxybiphenyl, 3,3',5,5'-tert-pentyl-2,2'-dihydroxybiphenyl, 6,6'-methylenebis(2,4-tert-dibutylphenol), 3,3',5,5'-tetramethyl-2,2'-dihydroxybiphenyl, 6,6 '-thiobis(2,2'-di-tert-butyl-4,4'-dimethylphenol), 6,6'-methylenebis(2,2',4,4'-tetra-tert-butylphenol), 6,6'-oxybis(2,2',4,4'-tetra-tert-butylphenol), 6,6'-thiobis(2,2',4,4'-tetra-tert-butylphenol), 6,6'-methylenebis(2,2',4,4'-tetra-tert-pentylphenol), 6,6'-oxybis(2,2',4,4'-tetra-tert-pentylphenol), 6,6'- Thiobis(2,2',4,4'-tetra-tert-pentylphenol), 6,6'-methylenebis(2,2'-di-tert-butyl-4,4'-dimethylphenol), 6,6'-oxybis(2,2'-di-tert-butyl-4,4'-dimethylphenol), 3,3'-di-tert-butyl-5,5'-dimethyl-2,2'-dihydroxybiphenyl, 6,6'-thiobis(2,2',4,4'-tetramethylphenol), 6,6'-methylenebis(2,2',4,4'-tetramethylphenol), 6,6'-oxybis(2, 2',4,4'-tetramethylphenol), 6,6'-methylenebis(2,2',4,4'-tetra-α-cumylphenol), 6,6'-thiobis(2,2',4,4'-tetra-α-cumylphenol), 6,6'-oxybis(2,2',4,4'-tetra-α-cumylphenol), 3,3'-di-tert-butyl-5,5'-di-tert-pentyl-2,2'-dihydroxybiphenyl, 3,3'-di-tert-butyl-5,5'-di-α-cumyl-2,2'-dihydroxybiphenyl, 3,3'-di-tert-pentyl-5,5'-Di-tert-butyl-2,2'-dihydroxybiphenyl, 3,3'-di-tert-pentyl-5,5'-dimethyl-2,2'-dihydroxybiphenyl, 3,3'-di-tert-pentyl-5,5'-α-cumyl-2,2'-dihydroxybiphenyl, 3,3'-dimethyl-5,5'-di-tert-butyl-2,2'-dihydroxybiphenyl, 3,3'-dimethyl-5,5'-di-tert-pentyl-2,2 '-dihydroxybiphenyl, 3,3'-dimethyl-5,5'-di-α-cumyl-2,2'-dihydroxybiphenyl, 3,3'-di-α-cumyl-5,5'-di-tert-butyl-2,2'-dihydroxybiphenyl, 3,3'-di-α-cumyl-5,5'-di-tert-pentyl-2,2'-dihydroxybiphenyl, 3,3'-di-α-cumyl-5,5'-dimethyl-2,2'-dihydroxybiphenyl, etc.

[0037] By adding the diphosphite compound of the present invention represented by formula (I) to an organic material, thermal degradation, oxidative degradation, etc. of the organic material can be reduced, and the organic material can be stabilized. Furthermore, the diphosphite compound of the present invention has high heat resistance. Therefore, the diphosphite compound of the present invention is particularly suitable as an active ingredient of a stabilizer for organic materials that require high processing temperatures.

[0038] Therefore, the present invention also provides a stabilizer for organic materials containing the diphosphite compound of the present invention represented by formula (I), a method for stabilizing organic materials by adding the diphosphite compound of the present invention represented by formula (I) to an organic material, and an organic material composition containing an organic material and the diphosphite compound of the present invention represented by formula (I). In these embodiments, as the diphosphite compound of the present invention represented by formula (I), one type of diphosphite compound represented by formula (I) may be used, or two or more types of diphosphite compounds represented by formula (I) may be used in combination.

[0039] Examples of organic materials that can be stabilized by the diphosphite compound of the present invention include, but are not limited to, the following: The organic material may be one type of organic material or a mixture of two or more types of organic materials.

[0040] (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,

[0041] (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, (20) Polyester resins, such as polyethylene terephthalate and polybutylene terephthalate;

[0042] (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,

[0043] (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,

[0044] (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.

[0045] Among these, thermoplastic resins, particularly polyolefins such as polyethylene, for example, HD-PE, LD-PE, LLDPE and polypropylene, polyamides, engineering plastics such as polyethylene terephthalate, polybutylene terephthalate and polycarbonate are preferably used.

[0046] 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.

[0047] Engineering plastics are not particularly limited. Polyamide resins may be any resins that have amide bonds in the polymer chain and can be melted by heating. 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 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 and nylon 6 / 12, which are copolymers of nylon 66 and nylon 6. Polyester resins may be any resins that have ester bonds in the polymer chain and can be melted by heating, including polyesters obtained by polycondensation of dicarboxylic acids and dihydroxy compounds. Polyester resins may be either homopolyesters or copolyesters. 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.

[0048] When the diphosphite compound of the present invention represented by formula (I) is added to an organic material to stabilize it, the content of the diphosphite compound of the present invention is usually 0.0001 part by mass or more, preferably 0.001 part by mass or more, more preferably 0.01 part by mass or more, and even more preferably 0.05 part 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 diphosphite compound of the present invention 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.

[0049] When the diphosphite compound of the present invention represented by formula (I) is added to an organic material, other additives may be added to the organic material as needed, such as phenolic antioxidants, sulfur-based antioxidants, phosphite-based antioxidants other than the diphosphite compound of the present invention, 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, gloss agents, calcium stearate, etc. Neutralizing agents such as sodium or hydrotalcite, color improvers such as 9,10-dihydro-9-oxa-10-phosphophenanthrene-10-oxide, and co-stabilizers such as benzofurans and indolines 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 can also be added. These additives can be added to the organic material simultaneously with the diphosphite compound of the present invention, or can be added to the organic material at a different stage from the diphosphite compound of the present invention. A single additive can be used, or two or more additives can be used in combination. The amount of these additives to be added is not particularly limited as long as it does not affect the desired properties of the organic material, but it may usually be about 0.001 to 5 parts by mass, preferably about 0.005 to 3 parts by mass, and more preferably about 0.01 to 1 part by mass, per 100 parts by mass of the organic material.

[0050] 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.

[0051] (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.

[0052] (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.

[0053] (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.

[0054] (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.

[0055] (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.

[0056] (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.

[0057] (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.

[0058] (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.

[0059] (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.

[0060] 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.

[0061] Examples of phosphite-based antioxidants other than the diphosphite-based compounds of the present invention include the following: As the phosphite-based antioxidants other than the diphosphite-based compounds of the present invention, 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] phosphites, 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.

[0062] 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.

[0063] (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'-octylphenyl)benzotriazole 2-(3',5'-di-t-amyl-2'-hydroxyphenyl)benzotriazole, 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 triazole, 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.

[0064] 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,

[0065] 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.5] undecane, mixed esters with 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, 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-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,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, 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.

[0066] (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.

[0067] (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.

[0068] 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.

[0069] 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. Polyamide stabilizers include, for example, copper or divalent manganese salts of iodides or phosphorus compounds, and mixtures thereof.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] Examples of fillers include calcium carbonate, silicates, glass fibers, asbestos, talc, kaolin, mica, barium sulfate, carbon black, carbon fibers, zeolites, and mixtures thereof.

[0075] Among these additives, those that are preferably used are phenol-based antioxidants, phosphite-based antioxidants other than the diphosphite-based compounds of the present invention, ultraviolet absorbers, hindered amine-based light stabilizers, peroxide scavengers and neutralizing agents.

[0076] 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,

[0077] 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), 3,9-bis[2-(3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl]-2,4,4,10-tetraoxaspiro[5 5]undecane, 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, etc.

[0078] Particularly preferred phosphite-based antioxidants other than the diphosphite-based compounds of the present invention 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, 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.

[0079] 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.

[0080] 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,

[0081] 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.

[0082] The diphosphite compound of the present invention represented by formula (I) and / or other optional additives can be added to an organic material using any known method and apparatus for obtaining a homogeneous mixture. For example, when the organic material is a solid polymer, the diphosphite compound of the present invention and / or other optional additives can be dry-blended directly with the solid polymer, or the diphosphite compound and / or other optional additives can be added to the solid polymer in the form of a masterbatch. When the organic material is a liquid polymer, in addition to the above-mentioned addition method, the diphosphite compound of the present invention 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 (e.g., oil), in addition to the above-mentioned addition method, the diphosphite compound of the present invention and / or other optional additives can be directly added to the organic material to dissolve it, or the diphosphite compound of the present invention and / or other optional additives can be added in a dissolved or suspended state in a liquid medium.

[0083] The diphosphite compound of the present invention represented by formula (I) has excellent performance as a stabilizer for various organic materials, including thermoplastic resins such as polyolefins. Organic materials to which the diphosphite compound of the present invention has been added are stable against thermal and oxidative degradation during production, processing, and use, resulting in high-quality products. Furthermore, because the diphosphite compound of the present invention has high heat resistance, it can be suitably used in the processing of organic materials that require high processing temperatures. [Example]

[0084] 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.

[0085] [Example 1] 15.0 g (67.5 mmol) of 4,6-di-tert-butylresorcinol, 19.5 g (141.7 mmol, 2.1 equivalents relative to 4,6-di-tert-butylresorcinol (hereinafter the same)) of phosphorus trichloride, and 150 mL of toluene were placed in a four-neck flask and cooled to -40°C under a nitrogen atmosphere. A mixture of 20.5 g (202.4 mmol, 3.0 equivalents) of triethylamine and 150 mL of toluene was added dropwise over 1 hour and 30 minutes. The mixture was then heated to room temperature and maintained at this temperature for 1 hour, and then further heated to 60°C and maintained at this temperature for 2.5 hours. After confirming by LC analysis that no raw materials remained, the mixture was cooled to -40°C, and a mixture of 55.4 g (135.0 mmol, 2.0 equivalents) of 3,3',5,5'-tetra-tert-butyl-2,2'-dihydroxybiphenyl, 41.0 g (404.8 mmol, 6.0 equivalents, a total of 9.0 equivalents including the amount used in the first reaction step), and 150 mL of toluene was added dropwise over 30 minutes. The mixture was then stirred at room temperature for 15 hours, then heated to 80°C and stirred for an additional 4 hours. After completion of the reaction, the reaction mixture was returned to room temperature and quenched with water. The organic layer obtained by separation using toluene was washed twice with saturated brine. The resulting organic layer was dried over magnesium sulfate, filtered, and concentrated to obtain a crude product, which was purified by silica gel chromatography (ethyl acetate:hexane = 1:30 (volume ratio)) and reverse-phase silica gel chromatography (acetonitrile:ethyl acetate = 4:1 to 2:1 (volume ratio)), and then repulped and washed with an ethyl acetate / acetonitrile mixed solvent to obtain 47.2 g of diphosphite compound A-1 represented by formula (A-1) in a yield of 63.7% and a purity of 99.6%.

[0086] [ka]

[0087] 1 H-NMR (CD2Cl2, 400 MHz): δ1.23(s, 18H), δ1.36(s,36H), δ1.40(s, 36H), δ7.24-7.26(m, 5H), δ7.28(s, 1H), δ7.45-7.46(m, 4H)

[0088] [Example 2] In the method shown in Example 1, 15.0 g of 4,6-di-tert-pentylresorcinol was used instead of 4,6-di-tert-butylresorcinol to obtain 44.8 g of diphosphite compound A-2 represented by formula (A-2), in a yield of 66.3% and a purity of 99.0%.

[0089] [ka]

[0090] 1 H-NMR (CDCl3, 400 MHz): δ0.61(t, J=7.2Hz, 6H), δ1.30(s,12H), δ1.76(q, J=7.6Hz, 4H), δ2.33(s, 12H), δ2.34(s, 1 2H), δ7.01(d, J=1.6Hz, 4H), δ7.10(d, J=1.6Hz, 4H), δ7.19(s, 1H), δ7.37(t, J=1.2Hz, 1H)

[0091] [Example 3] In the method shown in Example 1, 168 g of 3,3',5,5'-tetra-tert-pentyl-2,2'-dihydroxybiphenyl was used instead of 3,3',5,5'-tetra-tert-butyl-2,2'-dihydroxybiphenyl, to obtain 118.4 g of diphosphite compound A-3 represented by formula (A-3), with a yield of 54.3% and a purity of 99.3%.

[0092] [ka]

[0093] 1 H-NMR (CD2Cl2, 400 MHz): δ0.65(t, J=7.4Hz, 12H), δ0.75(t, J=7.4Hz, 12H), δ1.26(s, 18H), δ1.32(s, 24H), δ1.36(s, 12H), δ1.40(s, 12H), δ1.65- 1.79(m, 12H), δ1.88-1.91(m, 4H), δ7.18(d, J=2.2Hz, 4H), δ7.27(t, J=2.5Hz, 1H), δ7.29(s, 1H), δ7.32(d, J=2.2Hz, 4H)

[0094] [Example 4] In the method shown in Example 1, 2.10 g of 4,6-di-tert-pentylresorcinol was used instead of 4,6-di-tert-butylresorcinol, and 8.03 g of 3,3',5,5'-tert-pentyl-2,2'-dihydroxybiphenyl was used instead of 3,3',5,5'-tetra-tert-butyl-2,2'-dihydroxybiphenyl, to obtain 6.96 g of diphosphite compound A-4 represented by formula (A-4) in a yield of 66.9% and a purity of 99.9%.

[0095] [ka]

[0096] 1 H-NMR (CD2Cl2, 400 MHz): δ0.53(t, J=7.5Hz, 6H), δ0.64(t, J=7.4Hz, 12H), δ0.75(t, J=7.4Hz, 12H), δ1.22(s, 12H), δ1.31(s, 24H), δ1.36(s, 12H), δ1.39(s, 1 2H), δ1.61-1.77(m, 16H), δ1.88-1.92(m, 4H), δ7.12(s, 1H), δ7.17(d, J=2.5Hz, 4H), δ7.24(t, J=2.7Hz, 1H), δ7.31(d, J=2.5Hz, 4H)

[0097] [Example 5] In the method shown in Example 1, 1.50 g of 4,6-di-tert-pentylresorcinol was used instead of 4,6-di-tert-butylresorcinol, and 4.34 g of 6,6'-thiobis(2,2'-di-tert-butyl-4,4'-dimethylphenol) was used instead of 3,3',5,5'-tetra-tert-butyl-2,2'-dihydroxybiphenyl, to obtain 2.57 g of diphosphite compound A-5 represented by formula (A-5), with a yield of 33.0% and a purity of 97.4%.

[0098] [ka]

[0099] 1 H-NMR (CDCl3, 400 MHz): δ0.68(t, J=7.5Hz, 6H), δ1.30(s, 36H), δ1.44(s, 12H), δ1.99(m, 4H), δ2.21(s, 12H), δ6.97(d, J=2.2Hz, 4H), δ7.16(t, J=2.1Hz, 1H), δ7.19(d, J=1.7Hz, 4H), δ7.21(s, 1H)

[0100] [Example 6] In the method shown in Example 1, 3.0 g of 4,6-di-tert-pentylresorcinol was used instead of 4,6-di-tert-butylresorcinol, and 5.99 g of 3,3',5,5'-tetramethyl-2,2'-dihydroxybiphenyl was used instead of 3,3',5,5'-tetra-tert-butyl-2,2'-dihydroxybiphenyl, to obtain 4.99 g of diphosphite compound A-5 represented by formula (A-6), in a yield of 52.7% and with a purity of 99.8%.

[0101] [ka]

[0102] 1 H-NMR (CDCl3, 400 MHz): δ0.61(t, J=7.5Hz, 6H), δ1.30(s, 12H), δ1.75-1.77(m, 4H), δ2.33(s, 12H), δ2.34(s, 12 H), δ7.01(d, J=1.7Hz, 4H), δ7.10(d, J=1.7Hz, 4H), δ7.19(s, 1H), δ7.37(t, J=1.2Hz, 1H)

[0103] [Example 7] In the method shown in Example 1, 2.7 g of 4,6-di-tert-pentylresorcinol was used instead of 4,6-di-tert-butylresorcinol, and 13.9 g of 3,3',5,5'-tetra-α-cumyl-2,2'-dihydroxybiphenyl was used instead of 3,3',5,5'-tetra-tert-butyl-2,2'-dihydroxybiphenyl, to obtain 6.38 g of diphosphite compound A-7 represented by formula (A-7), in a yield of 36.4% and a purity of 98.6%.

[0104] [ka]

[0105] 1 H-NMR (CD2Cl2, 400 MHz): δ0.57(t, J=7.4Hz, 6H), δ1.12(s, 12H), δ1.56(s, 16H), δ1.68(s, 36H), δ6.79(t, J=2.7Hz, 1H), δ6.99-7.03(m, 24H), δ7.14-7.33(m, 25H)

[0106] [Comparative Example 1] A three-neck flask was charged with 4.66 g (11.4 mmol) of 3,3',5,5'-tetra-tert-butyl-2,2'-dihydroxybiphenyl and 12 mL of toluene, and the mixture was heated to 60 °C under a nitrogen atmosphere. 1.80 g (13.1 mmol) of phosphorus trichloride was added, followed by dropwise addition of 7.34 g (56.8 mmol) of N,N-diisopropylethylamine over 1 hour and 30 minutes. After maintaining the temperature for 2 hours, 0.5 g (4.54 mmol) of resorcinol was added and the mixture was maintained for an additional 6 hours. After confirming no change in the reaction by LC analysis, the reaction mixture was returned to room temperature and quenched with 10 mL of water. The organic layer was separated using toluene, and the resulting mixture was washed twice with saturated brine. The obtained organic layer was dried over magnesium sulfate, filtered, and concentrated to obtain a crude product, which was purified by silica gel chromatography (ethyl acetate:hexane=1:30 (volume ratio)) to obtain 1.50 g of diphosphite compound B-1 represented by formula (B-1) in a yield of 33.5% and a purity of 98.6%.

[0107] [ka]

[0108] 1 H-NMR (CDCl3, 400 MHz): δ1.35(s, 36H), δ1.47(s, 36H), δ6.80(dd, J=8.2, 2.2Hz, 2H), δ6.91(m, 1H), δ7.15(t, J=8.3Hz, 1H), δ7.19(d, J=2.4Hz, 4H), δ7.45(d, J=2.4Hz, 4H)

[0109] Comparative Example 2 In the method shown in Example 1, 18.0 g of 2,4-tert-butylphenol was used instead of 3,3',5,5'-tetra-tert-butyl-2,2'-dihydroxybiphenyl, to obtain 45.3 g of diphosphite compound B-2 represented by formula (B-2), in a yield of 46.9% and a purity of 97.8%.

[0110] [ka]

[0111] 1 H-NMR (CD2Cl2, 400 MHz): δ1.26(s, 36H), δ1.31(s, 54H), δ7.04(dd, J=8.4, 2.5Hz, 4H), δ7.16(dd, J=8 .4, 2.0Hz, 4H), δ7.31(s, 1H), δ7.33(d, J=2.5Hz, 4H), δ7.51(t, J=3.3Hz, 1H)

[0112] [Reference example 1] In the method shown in Comparative Example 1, A-1 was synthesized using 0.21 g of 4,6-di-tert-butylresorcinol instead of resorcinol, and 0.15 g of A-1 was obtained in a yield of 14.3%, and 0.17 g of compound A-1' represented by formula (A-1') was obtained in a yield of 20.4%. [ka]

[0113] 1 H-NMR (CDCl3, 400 MHz): δ1.33(s, 72H), δ7.14(d, J=2.5Hz, 4H), δ7.36(m4H)

[0114] [Analysis conditions for diphosphite compounds] The purity of the compounds in the Examples and Comparative Examples was measured under the following conditions. Purity (LC) Model: LC-20A (Shimadzu Corporation) Column: SUMIPAX ODS A-212 (5 μm, 6 mm diameter, 150 mm) (manufactured by Sumika Chemical Analysis Center, Ltd.) Injection volume: 1 μL (each methanol / chloroform = 1 / 1 (v / v) solution) Mobile phase: A solution acetonitrile Solution B: 2-propanol Gradient: B concentration (%) 80% → (20 min) → 100% → (30 min) → 100% Flow rate: 1.0mL / min Column temperature: 40℃ Measurement wavelength: UV, 280nm

[0115] Structural analysis of the compounds of Examples and Comparative Examples ( 1 H-NMR measurements were carried out using the following equipment. Equipment: Varian 400MR (Agilent)

[0116] [Evaluation of heat resistance (TG-DTA)] The diphosphite compounds A-1 to A-7 and B-1 to B-2 obtained in Examples 1 to 7 and Comparative Examples 1 and 2 were measured using a thermogravimetric differential thermal analyzer (Shimadzu Corporation, "DTG-60H") in a nitrogen atmosphere by heating from 23-25°C to 200°C at a rate of 20°C / min, holding for 10 minutes, then cooling to 100°C, and then heating to 600°C at a rate of 20°C / min, and the temperature at which the mass loss reached 1% was measured. The results are shown in Table 1. A higher temperature indicates better heat resistance. Based on the obtained results, evaluation was performed according to the following evaluation criteria. A: 340℃ or higher, B: less than 340℃

[0117] [Evaluation of processing stability (MFR)] Using the diphosphite compounds A-1 to A-7 and B-1 to B-2 obtained in Examples 1 to 7 and Comparative Examples 1 and 2, respectively, pellets were prepared according to the following procedure. 100 parts by mass of homopolypropylene (Sumitomo Chemical, MFR = 17 to 21) was dry-blended with 0.05 parts by mass of calcium stearate (Nitto Kasei Kogyo Co., Ltd.), 0.05 parts by mass of Irganox 1010 (BASF Japan Ltd.), and 0.1 parts by mass of a diphosphite compound, and the resulting mixture was kneaded in a twin-screw extruder (BTN-32, PLABOR) with a cylinder diameter of 32 mm under nitrogen atmosphere at a temperature of 230 ° C and a screw rotation speed of 50 rpm to obtain pellets. The MFR of the resulting pellets was measured according to the following method.

[0118] The MFR was measured using a melt flow index tester (Model No. 120-LABOT-50, manufactured by Yasuda Seiki Seisakusho Co., Ltd.) at a temperature of 230°C and a load of 21.18 N according to the method specified in JIS K7210-2014. Resin compositions containing thermoplastic resins primarily composed of polypropylene resins undergo thermal processing, resulting in an increase in their MFR. Therefore, the smaller the MFR, the better the processing stability. The MFR of the homopolypropylene used in this evaluation before processing was approximately 17 to 21. The MFR of pellets containing the compound of Example 2 was 17.2, and the MFR of pellets containing the compound of Comparative Example 2 was 17.6. Furthermore, the compounds of Examples 1 and 3 to 7 all exhibited good processing stability.

[0119] [Table 1]

[0120] It was confirmed that the diphosphite compounds of the examples had high heat resistance. [Industrial Applicability]

[0121] The diphosphite compound of the present invention has high heat resistance and can therefore be suitably used in the processing of organic materials which require high processing temperatures.

Claims

1. Formula (I): 【Chemical 1】 [In formula (I), R １ represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 25 carbon atoms, R ２ represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, R ３ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 25 carbon atoms, X represents a single bond, an alkylidene group having 1 to 4 carbon atoms, a sulfur atom, or an oxygen atom. A diphosphite compound represented by the formula:

2. R １ is a tertiary alkyl group having 4 to 12 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or a tertiary aralkyl group having 9 to 15 carbon atoms.

3. The compound of formula (I) above has the formula (I'): 【Chemistry 2】 [In formula (I'), R １ , R ２ , R ３ and X is as defined above.

2. The compound of claim 1, wherein

4. 2. The compound of claim 1, wherein X is a single bond.

5. R ３ is a tertiary alkyl group having 4 to 12 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, or a tertiary aralkyl group having 9 to 21 carbon atoms.

6. R ３ is a tertiary alkyl group having 5 to 10 carbon atoms.

7. Formula (II): 【Chemistry 3】 [In formula (II), R １ is as defined above] and a phosphorus trihalide, the reaction product of which is a compound represented by formula (III): 【Chemistry 4】 [In formula (III), R ２ , R ３ and X is as defined above. The method for producing the compound according to claim 1, further comprising reacting a compound represented by the formula:

8. A stabilizer for organic materials comprising the compound of claim 1.

9. The stabilizer of claim 8 , wherein the organic material is a thermoplastic resin.

10. The stabilizer according to claim 9, wherein the thermoplastic resin is a polyolefin or an engineering plastic.

11. A method for stabilizing an organic material, comprising adding the compound according to claim 1 to the organic material.

12. An organic material composition comprising an organic material and the compound of claim 1.

13. The composition of claim 12 wherein the organic material is a thermoplastic resin.

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

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