JPH10101687A - Phosphite esters, production method thereof and use thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new cyclic phosphite ester useful as a deterioration-preventing agent against the thermal and oxidative deteriorations of organic materials, etc., by reacting a diol compound with a phosphorus trihalide and a specific hydroxy compound. SOLUTION: A new phosphite ester of formula I [R<1> -R<4> are each H, a 1-8C alkyl, a 7-12C aralkyl; X is a bonding group; RA is (substituted) phenyl]. This ester of formula I is useful as a deterioration-preventing agent for organic materials such as thermoplastic resins, etc. The compound of formula I is obtained by reacting a diol compound of formula II (e.g. neopentyl glycol) with a phosphorus trihalide (e.g. phosphorus trichloride) and a hydroxy compound of the formula: HO-X-RA [e.g. 2,2'-methylene bis(6-t-butyl-4-methylphenol)] in the presence of triethylamine, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel phosphite, a method for producing the same, and a use thereof as a stabilizer for organic materials.

[0002]

2. Description of the Related Art Organic materials such as thermoplastic resins, thermosetting resins, natural or synthetic rubbers, mineral oils, lubricating oils, adhesives, paints and the like are used during production, processing and further use. Occasionally, it deteriorates due to the action of heat, oxygen, etc., resulting in a decrease in strength physical properties of organic materials due to phenomena such as molecular breakage or molecular cross-linking, a change in flowability, coloring, a decrease in surface physical properties, etc., and significantly impairs commercial value. Is known to be. It has been known to stabilize organic materials by adding various phenolic antioxidants and phosphorus-based antioxidants for the purpose of solving such problems as heat and oxidative deterioration. For example, tris (2,4-di-t-butylphenyl) phosphite, tetrakis (2,4-di-t-butylphenyl)-as a phosphorus-based antioxidant
4,4'-diphenylenephosphonite and the like are used.

[0003] However, these known phosphorus-based antioxidants have a problem in that the effect of stabilizing against thermal deterioration and oxidative deterioration is insufficient.

On the other hand, as a solution to the problem of the phosphorus-based antioxidant, the present inventors have already proposed 2- [2- (4,8-diamine).
-t-Butyl-2,10-dimethyl-12H-dibenzo [d, g] [1,3,2]
Dioxaphosphin-3-t-butyl-5-methylbenzyl]-
A cyclic phosphite derived from bisphenols such as 6-t-butyl-4-methylphenol has been proposed (JP-A-8-412)
No. 45).

Subsequently, the present inventors further produced various phosphorus compounds and made intensive studies. As a result, they obtained cyclic phosphites derived from diols, which are completely different from bispheres. The present inventors have found that the obtained cyclic phosphite exhibits an excellent stabilizing effect equal to or more than that of the cyclic phosphite derived from bisphenols, and completed the present invention.

[0006]

That is, the present invention provides a compound represented by the general formula (I):

[0007]

(Wherein R ¹ , R ² , R ³ and R ₄ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or an aralkyl group having 7 to 12 carbon atoms. X is a linking group. To
^RA represents a phenyl group which may have a substituent. )
The present invention provides a practically excellent phosphite represented by the formula (1), a method for producing the same, and a use thereof.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. In the phosphites represented by the formula (I) of the present invention, the substituents R ₁ , R ₂ , R ₃ and R ₄ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or 7 carbon atoms. Represents an aralkyl group of from 12 to 12, but has 1 to 8 carbon atoms
Representative examples of the alkyl group of, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, se
c-butyl, t-butyl, t-pentyl, i-octyl, t-octyl, 2-ethylhexyl and the like. In addition, carbon number 7
Representative examples of aralkyl groups of to 12 include, for example, benzyl, α-methylbenzyl, α, α-dimethylbenzyl and the like. R ₁ , R ₂ , R ₃ and R ₄ are preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, more preferably a hydrogen atom or a methyl group.

X represents a linking group. Examples of the linking group include a simple bond and a divalent linking group having a total carbon number of about 1 to 20, which may have a hetero atom. Specific examples of the linking group include the following formulas (II) and (II)
And groups represented by (I), (IV), (V), (VI), (VII) or (VIII). * -A- (II) * -BOA- (III) * -C (O) -A- (IV) * -BOC (O) -A- (V) * -D- C (O) -O-A- ( VI) * -G-N (R 6) -A- (VII) * -G-N (R 6) -C (O) -A- (VIII)

(Wherein, * represents a bond to an oxygen atom, A represents a mere bond or an alkylene group having 1 to 8 carbon atoms, B represents a dihydric alcohol residue, and D represents a carbon atom. G represents an alkylene group having 1 to 8 carbon atoms, G represents an alkylene group having 2 to 8 carbon atoms, R ⁶ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or the formula (IX)

[0012] (In the formula, R ¹ , R ² , R ³ , R ⁴ and G have the same meaning as described above.)

Represents a group represented by Here, typical examples of the alkylene group having 1 to 8 carbon atoms include linear alkylene such as methylene, ethylene, propylene, butylene, pentamethylene, hexamethylene, octamethylene, 1-methylethylene, dimethylmethylene, 2 , 2-dimethyl-1,3-propylene and the like. The dihydric alcohol residue is
Indicates a portion of the dihydric alcohol except for two OHs,
Representative examples of the divalent alcohol residue include, for example, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-
Butanediol, 2,3-butanediol, 2-methyl-1,3-
Propanediol, 1,2-pentanediol, 1,5-pentanediol, 2,4-pentanediol, neopentyl glycol, 1,2-hexanediol, 1,5-hexanediol, 1,6-hexanediol, 2 , 5-hexanediol, 2-
Methyl-2,4-pentanediol, 2-methyl-1,5-pentanediol, 3,3-dimethylbutanediol, 2,3-dimethyl-2,3-butanediol, 2-ethyl-2-methyl-1 , 3-propanol, 2,2-diethyl-1,3-propanediol, 2,
4-dimethyl-2,4-pentanediol, 1,2-octanediol, 1,8-octanediol, 2,5-dimethyl-2,5-hexanediol, 2-ethyl-1,3-hexanediol, 2 , 2,
4-trimethyl-1,3-pentanediol, 1,9-nonanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,
2-decanediol, 1,10-decanediol, 1,12-dodecanediol, 1,2-tetradecanediol, 1,14-tetradecanediol, 1,2-hexadecanediol, 1,16-
A residue of an alkylene diol such as hexadecane diol,

2-butene-1,4-diol, 2-methylene-1,3
-Residues of diols having a double bond such as propanediol, 5-hexene-1,2-diol, 7-octene-1,2-diol, 1,2-cyclopentanediol, 1,3-cyclopentanediol , 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, 1,2-
Cyclooctadiol, 1,4-cyclooctanediol,
Cyclic diol residues such as 1,5-cyclooctanediol, p-menthane-3,8-diol, 4,4'-isopropylidenedicyclohexanol, ethylene glycol, diethylene glycol, triethylene glycol, 3,9-bis (1,1-
Dimethyl-2-hydroxyethyl) -2,4,8,10-tetraoxaspiro [5,5] undecane, neopentyl glycol
Examples thereof include diol residues having a hetero atom such as hydroxypivalate, 2,2′-thiodiethanol, 2-methylthio-1,2-propanediol, and diethanolamine. As typical examples of the alkylene group having 2 to 8 carbon atoms, for example, ethylene, propylene, butylene, pentamethylene, hexamethylene, linear alkylene such as octamethylene, 1-methylethylene, 2,2-dimethyl-1, And branched alkylene such as 3-propylene. Carbon number 1
Examples of the alkyl group 8 include the same alkyl groups as described above.

When the linking group X is a group represented by the formula (II), A is preferably a simple bond, alkylene having 2 to 8 carbon atoms, and particularly preferably a simple bond, propylene or the like. preferable. In the case of a group represented by the formula (III), A is preferably methylene, B is preferably ethylene, propylene or the like. When it is a group represented by the formula (IV), A is preferably a mere bond, ethylene, etc., and when it is a group represented by the formula (V), A is a mere bond, ethylene, dimethylmethylene, etc. However, B preferably has an ethylene glycol residue, a 1,2-propanediol residue or the like. In the case of the group represented by (VI), A is preferably a mere bond, methylene or the like, and D is preferably methylene or the like. In the case of a group represented by (VII), A is methylene, ethylene, etc., G is ethylene, propylene, etc., and R ⁶ is hydrogen, methyl, ethyl, formula (IX), etc. Is preferred. Also (VI
In the case of the group represented by II), A may be a mere bond, ethylene, etc., G may be ethylene, propylene, etc., and R ⁶ may be hydrogen, methyl, ethyl, formula (IX), etc. preferable.

^RA in the phosphites of the present invention represents a phenyl group which may have a substituent, and the total number of carbon atoms is usually about 6 to 30. Representative examples of such a phenyl group include, for example, groups represented by formulas (X) and (XI).

[0017]

(Wherein R ⁷ and R ⁸ are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, Represents an aralkyl group or a phenyl group of the formulas 7 to 12, wherein Y and Z each independently represent a hydrogen atom,
An alkyl group, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a phenyl group, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms or a carbon number Represents 7 to 12 aralkyloxy groups. )

[0019]

(Wherein R ⁹ and R ¹⁰ are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, R ¹¹ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, W represents a mere bond, a sulfur atom or an alkyl group having 1 to 8 carbon atoms or 5 carbon atoms; Represents a methylene group which may be substituted with a cycloalkyl group of ~ 8.)

The alkyl group having 1 to 8 carbon atoms and the aralkyl group having 7 to 12 carbon atoms include the same alkyl groups and aralkyl groups as described above. In addition, carbon number 5-8
Examples of the cycloalkyl group include cyclopentyl,
Examples of the alkylcycloalkyl group having 6 to 12 carbon atoms such as cyclohexyl, cycloheptyl and cyclooctyl include 1-methylcyclopentyl, 1-methylcyclohexyl, 1-methyl-4-i-propylcyclohexyl and the like. Examples of the alkoxy group having 1 to 8 carbon atoms include an alkoxy group in which the alkyl portion is the same alkyl as the above-described alkyl having 1 to 8 carbon atoms.
Examples of the 12 aralkyloxy groups include aralkyloxy groups in which the aralkyl moiety is the same aralkyl as the above aralkyl having 7 to 12 carbon atoms.

R ⁷ is methyl, t-butyl, t-pentyl,
To be t-octyl, R ⁸ is hydrogen, methyl,
Preference is given to t-butyl, t-pentyl and t-octyl. One of Y and Z is a hydroxyl group and has 1 to 8 carbon atoms.
Is preferably an alkoxy group or an aralkyloxy group having 7 to 12 carbon atoms, and the other is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and more preferably, one of them is a hydroxyl group or a methoxy group. Is preferred.

R ⁹ is preferably a t-alkyl group such as t-butyl, t-pentyl, t-octyl, 1-methylcyclohexyl and the like. R ¹⁰ is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-
It is preferably an alkyl group having 1 to 5 carbon atoms such as butyl and t-pentyl, and particularly preferably t-butyl. R ¹¹ is preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, particularly preferably a hydrogen atom or a methyl group. W is preferably a simple bond, a methylene group or a methylene group substituted by a methyl group. When R ^A is a group represented by the formula (XI), the linking group X is preferably a simple bond of the formula (II).

The phosphites represented by the above formula (I) are, for example, those represented by the general formula (XII)

(Wherein R ₄ , R ₅ , R ₆ and R ₇ have the same meaning as in claim 1), phosphorus trihalide, and HO-X- ^{RA of the} general formula (XIII) (XIII) (wherein X and R ^A have the same meanings as described above). Examples of the phosphorus trihalide used here include phosphorus trichloride, phosphorus tribromide and the like. In particular, phosphorus trichloride is preferably used.

In the reaction, the reaction is promoted by coexistence of a dehydrohalogenating agent such as amines, pyridines, pyrrolidines and amides, and an alkali metal or alkaline earth metal hydroxide. Can also. Here, the amines include primary amines,
Any of secondary amines and tertiary amines may be used, for example, t-butylamine, t-pentylamine, t-hexylamine, t-octylamine, di-t-butylamine, di-t-pentylamine, di-t-hexylamine , Di-t-octylamine,
Examples thereof include trimethylamine, triethylamine, N, N-dimethylaniline, and N, N-diethylaniline, and preferably triethylamine. As pyridines,
For example, pyridine, picoline and the like can be mentioned, and pyridine is preferable. As pyrrolidines, for example, 1-
Methyl-2-pyrrolidine and the like. Examples of the amide include N, N-dimethylformamide and N, N-dimethylacetamide, and N, N-dimethylformamide is preferably used. Examples of the alkali metal or alkaline earth metal hydroxide include sodium hydroxide and calcium hydroxide, and preferably sodium hydroxide.

The reaction is usually performed 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, oxygen-containing hydrocarbons, and halogenated hydrocarbons. As aromatic hydrocarbons, for example, benzene, toluene, xylene, ethylbenzene, etc., as aliphatic hydrocarbons, for example, n-hexane, n-heptane, n-octane, etc., as oxygen-containing hydrocarbons, for example, diethyl Ether, dibutyl ether, tetrahydrofuran, 1,4-
Examples of halogenated hydrocarbons such as dioxane include, for example, chloroform, carbon tetrachloride, monochlorobenzene, dichloromethane, 1,2-dichloroethane, dichlorobenzene, and the like. Among these, toluene, xylene,
n-Hexane, n-heptane, diethyl ether, tetrahydrofuran, 1,4-dioxane, chloroform, dichloromethane and the like are preferably used.

As a reaction method, a two-step reaction method is usually employed in which a diol (XII) is reacted with phosphorus trihalide to produce an intermediate, and then a hydroxy compound (XIII) is reacted. . In the case of this method, the phosphorus trihalide is preferably used in an amount of about 1 to 1.1 times, more preferably about 1 to 1.05 times, the moles of the diol (XII). When a dehydrohalogenating agent is used, it is preferably used in an amount of about 2 to 2.4 moles, more preferably about 2 to 2.1 moles, per mole of phosphorus trihalide. The reaction between the diol (XII) and the phosphorus trihalide is usually carried out at about 0 to 200 ° C. This reaction is considered to produce an intermediate halogenophosphite, which may be isolated and then used for the next reaction, but is usually subjected to the reaction with the hydroxy compound (XIII) as a reaction mixture.

Next, when reacting the hydroxy compound (XIII), the diol (XII) is usually reacted with 1
It is used up to about 1.1 mole times. Also in this reaction, a dehydrohalogenating agent can be used, and in that case, the amount of the dehydrohalogenating agent is preferably about 1 to 1.2 moles per mol of the hydroxy compound (XIII). When the dehydrohalogenating agent is used in an excessive amount in the first reaction, the amount of the additional dehydrohalogenating agent is usually calculated including the remaining dehydrohalogenating agent. Reaction is usually 0-200
It is carried out at a temperature of about ° C.

After the completion of the reaction, when a dehydrohalogenating agent is used, the hydrohalide salt of the dehydrohalogenating agent generated by the reaction is removed, and the solvent is further removed. By performing an appropriate post-treatment such as column chromatography, the phosphites (I) of the present invention can be obtained.

Here, typical examples of the diols (XII) which are the raw materials of the phosphites (I) include, for example, 1,3-
Propanediol, 2,2-dimethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2-ethyl-2
-Methyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-
Propanediol, 1-phenyl-1,3-propanediol, 2,2-dimethyl-1-phenyl-1,3-propanediol, 2,2-diphenyl-1,3-propanediol, 2-methyl
-2-benzyl-1,3-propanediol, 2,4-pentanediol, 2-methyl-2,4-pentanediol, 2,4-dimethyl-2,4-pentanediol, 2,2,4-trimethyl -1,3-pentanediol, 1,3-butanediol, 2,2-dimethyl-
1,3-butanediol, 3-methyl-1,3-butanediol, 2,4-hexanediol, 2-ethyl-1,3-hexanediol, 3-methyl-2,4-heptanediol, 5-ethyl -3
-Methyl-2,4-heptanediol, 2-butyl-1,3-octanediol, 5-ethyl-3-methyl-2,4-nonanediol, 7-ethyl-2-methyl-4,6-nonanediol And the like. Diols
(XII) can be produced by condensing alkyl aldehydes, for example, according to the method described in J. Am. Chem. Soc., 70 , 1982 (1948). Any commercially available product may be used.

As a typical example of the hydroxy compound (XIII) as the other raw material, when the linking group X is represented by the formula (II) and A is a mere bond, for example, 2,2′-methylenebis (4 -Methyl-6-t-butylphenol), 2,2'-methylenebis (4-ethyl-6-t-butylphenol), 2,2 '
-Methylenebis (4-n-propyl-6-t-butylphenol), 2,2'-methylenebis (4-i-propyl-6-t-butylphenol), 2,2'-methylenebis (4-n-butyl-6) -t-
Butylphenol), 2,2'-methylenebis (4-i-butyl
-6-t-butylphenol), 2,2'-methylenebis (4,6-
Di-t-butylphenol), 2,2'-methylenebis (4-t-
Pentyl-6-t-butylphenol), 2,2'-methylenebis (4-nonyl-6-t-butylphenol), 2,2'-methylenebis (4-t-octyl-6-t-butylphenol), 2,2 '
-Methylenebis (4-methyl-6-t-pentylphenol), 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylenebis [4-methyl-6- (α
-Methylcyclohexyl) phenol)], 2,2'-methylenebis (4-methyl-6-nonylphenol), 2,2'-methylenebis (4-methyl-6-t-octylphenol), 2,2 '
-Methylenebis (4,6-di-t-pentylphenol), 2,
2'-methylenebis [4-nonyl-6- (α-methylbenzyl)
Phenol], 2,2'-methylenebis [4-nonyl-6-
(Α, α-dimethylbenzyl) phenol], 2,2′-ethylidenebis (4-methyl-6-butylphenol),

2,2'-ethylidenebis (4-ethyl-6-t-butylphenol), 2,2'-ethylidenebis (4-n-propyl-6-t-butylphenol), 2,2'-ethylidenebis (Four
-i-propyl-6-t-butylphenol), 2,2'-ethylidenebis (4-n-butyl-6-t-butylphenol), 2,2 '
-Ethylidenebis (4-i-butyl-6-t-butylphenol), 2,2'-ethylidenebis (4,6-di-t-butylphenol), 2,2'-ethylidenebis (4-t-pentyl- 6-t-butylphenol), 2,2'-ethylidenebis (4-nonyl-6
-t-butylphenol), 2,2'-ethylidenebis (4-t-
Octyl-6-t-butylphenol), 2,2'-ethylidenebis (4-methyl-6-t-pentylphenol), 2,2'-ethylidenebis (4-methyl-6-cyclohexylphenol), 2,2 '-Ethylidenebis [4-methyl-6- (α-methylcyclohexyl) phenol]], 2,2'-ethylidenebis
(4-methyl-6-nonylphenol), 2,2'-ethylidenebis (4-methyl-6-t-octylphenol), 2,2'-ethylidenebis (4,6-di-t-pentylphenol), 2 , 2 '
-Ethylidenebis [4-nonyl-6- (α-methylbenzyl)
Phenol], 2,2'-ethylidenebis [4-nonyl-6-
(α, α-dimethylbenzyl) phenol], 2,2′-propylidenebis (4-methyl-6-t-butylphenol),
2,2'-propylidenebis (4-ethyl-6-t-butylphenol),

2,2'-propylidenebis (4-n-propyl-6
-t-butylphenol), 2,2'-propylidenebis (4-i
-Propyl-6-t-butylphenol), 2,2'-propylidenebis (4-n-butyl-6-t-butylphenol), 2,2 '
-Propylidenebis (4-i-butyl-6-t-butylphenol), 2,2'-propylidenebis (4,6-di-t-butylphenol), 2,2'-propylidenebis (4-t-pentyl-6-t
-Butylphenol), 2,2'-propylidenebis (4-nonyl-6-t-butylphenol), 2,2'-propylidenebis (4-t-octyl-6-t-butylphenol), 2,2'-propylidenebis (4 -Methyl-6-t-pentylphenol), 2,2'-propylidenebis (4-methyl-6-cyclohexylphenol), 2,2'-propylidenebis [4-methyl-6- (α-methylcyclohexyl) phenol) , 2,2 '
-Propylidenebis (4-methyl-6-nonylphenol), 2,2'-propylidenebis (4-methyl-6-t-octylphenol), 2,2'-propylidenebis (4,6-di-t-
Pentylphenol), 2,2′-propylidenebis [4-nonyl-6- (α-methylbenzyl) phenol], 2,2′-propylidenebis [4-nonyl-6- (α, α-dimethylbenzyl) phenol], 2,2'-butylidenebis (4-methyl-6
-t-butylphenol), 2,2'-butylidenebis (4-ethyl-6-t-butylphenol), 2,2'-butylidenebis
(4,6-di-t-butylphenol), 2,2'-butylidenebis (4-methyl-6-cyclohexylphenol),

2,2'-butylidenebis [4-methyl-6- (α-
Methylcyclohexyl) phenol)], 2,2'-butylidenebis (4,6-di-t-pentylphenol), 2,2'-i-butylidenebis (4-methyl-6-t-butylphenol),
2'-i-butylidenebis (4-ethyl-6-t-butylphenol), 2,2'-i-butylidenebis (4,6-di-t-butylphenol), 2,2'-i-butylidenebis (4-methyl -6-cyclohexylphenol), 2,2'-i-butylidenebis [4-
Methyl-6- (α-methylcyclohexyl) phenol)], 2,2′-i-butylidenebis (4,6-di-t-pentylphenol), 2,2′-pentylidenebis (4-methyl-6- t
-Butylphenol), 2,2'-pentylidenebis (4-ethyl-6-t-butylphenol), 2,2'-pentylidenebis (4,6-di-t-butylphenol), 2,2'-pliers Redidenbis (4-methyl-6-cyclohexylphenol), 2,
2′-pentylidenebis [4-methyl-6- (α-methylcyclohexyl) phenol)], 2,2′-pentylidenebis (4,6
-Di-t-pentylphenol), biphenyl-2,2'-diol, 3,3 ', 5,5'-tetra-t-butylbiphenyl-2,2'-diol, 1,1'-binaphthyl-2 And bisphenols such as 2'-diol. Bisphenols can be prepared by known methods, for example, JP-A-52-122350, U.S. Pat.
It can also be produced by condensing alkylphenols according to the method described in Japanese Patent Publication No. 355 and Japanese Patent Publication No. 2-47451. In addition, any commercially available products can be used.

The linking group X is represented by the formula (II), and A has 1 carbon atom.
In the case where the alkylene group is from 1 to 8, for example, 2- (3-t
-Butyl-4-hydroxyphenyl) ethanol, 2-
(3-t-pentyl-4-hydroxyphenyl) ethanol, 2- (3-t-octyl-4-hydroxyphenyl) ethanol, 2- (3-cyclohexyl-4-hydroxyphenyl) ethanol, 2- [3- ( 1-methylcyclohexyl) -4-hydroxyphenyl] ethanol, 2- (3-tert-butyl-4-hydroxy-5-methylphenyl) ethanol, 2- (3-tert-pentyl-4)
-Hydroxy-5-methylphenyl) ethanol, 2-
(3-t-octyl-4-hydroxy-5-methylphenyl) ethanol, 2- (3-cyclohexyl-4-hydroxy-5-methylphenyl) ethanol, 2- [3
-(1-methylcyclohexyl) -4-hydroxy-5
-Methylphenyl] ethanol, 2- (3-t-butyl-4-hydroxy-5-ethylphenyl) ethanol,
2- (3-t-pentyl-4-hydroxy-5-ethylphenyl) ethanol, 2- (3-t-octyl-4-)
(Hydroxy-5-ethylphenyl) ethanol, 2-
(3-cyclohexyl-4-hydroxy-5-ethylphenyl) ethanol, 2- [3- (1-methylcyclohexyl) -4-hydroxy-5-ethylphenyl] ethanol,

2- (3,5-di-tert-butyl-4-hydroxyphenyl) ethanol, 2- (3-tert-pentyl-4-hydroxy-5-tert-butylphenyl) ethanol, 2- (3- t-octyl-4-hydroxy-5-t
-Butylphenyl) ethanol, 2- (3-cyclohexyl-4-hydroxy-5-t-butylphenyl) ethanol, 2- [3- (1-methylcyclohexyl) -4
-Hydroxy-5-t-butylphenyl] ethanol,
2- (3-t-butyl-4-methoxyphenyl) ethanol, 2- (3-t-pentyl-4-methoxyphenyl) ethanol, 2- (3-t-octyl-4-methoxyphenyl) ethanol, 2- (3-cyclohexyl-
4-methoxyphenyl) ethanol, 2- [3- (1-
Methylcyclohexyl) -4-methoxyphenyl] ethanol, 2- (3-t-butyl-4-methoxy-5-methylphenyl) ethanol, 2- (3-t-pentyl-
4-methoxy-5-methylphenyl) ethanol, 2-
(3-t-octyl-4-methoxy-5-methylphenyl) ethanol, 2- (3-cyclohexyl-4-methoxy-5-methylphenyl) ethanol, 2- [3-
(1-methylcyclohexyl) -4-methoxy-5-methylphenyl] ethanol, 2- (3-t-butyl-4)
-Methoxy-5-ethylphenyl) ethanol, 2-
(3-t-pentyl-4-methoxy-5-ethylphenyl) ethanol, 2- (3-t-octyl-4-methoxy-5-ethylphenyl) ethanol, 2- (3-cyclohexyl-4-methoxy-5) -Ethylphenyl) ethanol,

2- [3- (1-methylcyclohexyl)
-4-methoxy-5-ethylphenyl] ethanol, 2
-(3,5-di-t-butyl-4-methoxyphenyl)
Ethanol, 2- (3-t-pentyl-4-methoxy-
5-t-butylphenyl) ethanol, 2- (3-t-
Octyl-4-methoxy-5-t-butylphenyl) ethanol, 2- (3-cyclohexyl-4-methoxy-5-t-butylphenyl) ethanol, 2- [3-
(1-methylcyclohexyl) -4-methoxy-5-t
-Butylphenyl] ethanol, 3- (3-t-butyl-2-hydroxyphenyl) propanol, 3- (3-
t-butyl-4-hydroxyphenyl) propanol,
3- (5-tert-butyl-2-hydroxyphenyl) propanol, 3- (3-tert-pentyl-4-hydroxyphenyl) propanol, 3- (3-tert-octyl-4-)
(Hydroxyphenyl) propanol, 3- (3-cyclohexyl-4-hydroxyphenyl) propanol, 3
-[3- (1-methylcyclohexyl) -4-hydroxyphenyl] propanol, 3- (3-t-butyl-2)
-Hydroxy-5-methylphenyl) propanol, 3
-(3-t-butyl-4-hydroxy-5-methylphenyl) propanol, 3- (5-t-butyl-2-hydroxy-3-methylphenyl) propanol, 3- (3
-T-pentyl-4-hydroxy-5-methylphenyl) propanol, 3- (3-t-octyl-4-hydroxy-5-methylphenyl) propanol, 3- (3
-Cyclohexyl-4-hydroxy-5-methylphenyl) propanol, 3- [3- (1-methylcyclohexyl) -4-hydroxy-5-methylphenyl] propanol, 3- (3-t-butyl-4-hydroxy- 5
-Ethylphenyl) propanol,

3- (3-t-pentyl-4-hydroxy-5-ethylphenyl) propanol, 3- (3-t-
Octyl-4-hydroxy-5-ethylphenyl) propanol, 3- (3-cyclohexyl-4-hydroxy-5-ethylphenyl) propanol, 3- [3- (1
-Methylcyclohexyl) -4-hydroxy-5-ethylphenyl] propanol, 3- (3,5-di-t-butyl-2-hydroxyphenyl) propanol, 3-
(3,5-di-t-butyl-4-hydroxyphenyl)
Propanol, 3- (3-t-pentyl-4-hydroxy-5-t-butylphenyl) propanol, 3- (3
-Tert-octyl-4-hydroxy-5-tert-butylphenyl) propanol, 3- (3-cyclohexyl-4-)
(Hydroxy-5-t-butylphenyl) propanol,
3- [3- (1-methylcyclohexyl) -4-hydroxy-5-t-butylphenyl] propanol, 3-
(3-t-butyl-2-methoxyphenyl) propanol, 3- (3-t-butyl-4-methoxyphenyl) propanol, 3- (3-t-butyl-5-methoxyphenyl) propanol, 3- ( 3-t-pentyl-4-
Methoxyphenyl) propanol, 3- (3-t-octyl-4-methoxyphenyl) propanol, 3- (3
-Cyclohexyl-4-methoxyphenyl) propanol, 3- [3- (1-methylcyclohexyl) -4-methoxyphenyl] propanol,

3- (3-tert-butyl-2-methoxy-5)
-Methylphenyl) propanol, 3- (3-t-butyl-4-methoxy-5-methylphenyl) propanol, 3- (5-t-butyl-2-methoxy-3-methylphenyl) propanol, 3- (3 -T-pentyl-4
-Methoxy-5-methylphenyl) propanol, 3-
(3-t-octyl-4-methoxy-5-methylphenyl) propanol, 3- (3-cyclohexyl-4-methoxy-5-methylphenyl) propanol, 3- [3
-(1-methylcyclohexyl) -4-methoxy-5-
Methylphenyl] propanol, 3- (3-t-butyl-4-methoxy-5-ethylphenyl) propanol,
3- (3-t-pentyl-4-methoxy-5-ethylphenyl) propanol, 3- (3-t-octyl-4-
Methoxy-5-ethylphenyl) propanol, 3-
(3-cyclohexyl-4-methoxy-5-ethylphenyl) propanol, 3- [3- (1-methylcyclohexyl) -4-methoxy-5-ethylphenyl] propanol, 3- (3,5-di-t-) Butyl-2-methoxyphenyl) propanol, 3- (3,5-di-t-butyl-4-methoxyphenyl) propanol, 3- (3-
t-pentyl-4-methoxy-5-t-butylphenyl) propanol, 3- (3-t-octyl-4-methoxy-5-t-butylphenyl) propanol, 3-
(3-cyclohexyl-4-methoxy-5-t-butylphenyl) propanol,

3- [3- (1-methylcyclohexyl)
-4-methoxy-5-tert-butylphenyl] propanol, 3- (3-tert-butyl-2-ethoxyphenyl) propanol, 3- (3-tert-butyl-4-ethoxyphenyl) propanol, 3- (3 -Tert-butyl-4-ethoxy-5-methylphenyl) propanol, 3- (3-
t-butyl-2-ethoxy-5-methylphenyl) propanol, 3- (5-tert-butyl-2-ethoxy-3-)
Methylphenyl) propanol, 3- (3,5-di-t)
-Butyl-4-ethoxyphenyl) propanol, 3-
(3,5-di-tert-butyl-2-ethoxyphenyl) propanol, 4- (3-tert-butyl-2-hydroxyphenyl) butanol, 4- (3-tert-butyl-4-hydroxyphenyl) butanol, 4- (3-t-butyl-
4-hydroxy-5-methylphenyl) butanol,
-(3-t-butyl-2-hydroxy-5-methylphenyl) butanol, 4- (5-t-butyl-2-hydroxy-3-methylphenyl) butanol, 4- (3,5
-Di-tert-butyl-4-hydroxyphenyl) butanol, 4- (3,5-di-tert-butyl-2-hydroxyphenyl) butanol, 4- (3-tert-butyl-2-methoxyphenyl) butanol, 4- (3-t-butyl-4
-Methoxyphenyl) butanol, 4- (3-t-butyl-4-methoxy-5-methylphenyl) butanol,
4- (3-t-butyl-2-methoxy-5-methylphenyl) butanol, 4- (5-t-butyl-2-methoxy-3-methylphenyl) butanol, 4- (3,5-
Di-tert-butyl-4-methoxyphenyl) butanol,
4- (3,5-di-tert-butyl-2-methoxyphenyl) butanol,

5- (3-tert-butyl-2-hydroxyphenyl) pentanol, 5- (3-tert-butyl-4-hydroxyphenyl) pentanol, 5- (3-tert-butyl-4-hydroxy-phenyl) 5- (5-methylphenyl) pentanol, 5- (3-t-butyl-2-hydroxy-5-methylphenyl) pentanol, 5- (5-t-butyl-2)
-Hydroxy-3-methylphenyl) pentanol, 5
-(3,5-di-t-butyl-4-hydroxyphenyl) pentanol, 6- (3,5-di-t-butyl-2)
-Hydroxyphenyl) hexanol, 6- (3-t-
Butyl-2-hydroxyphenyl) hexanol, 6-
(3-t-butyl-4-hydroxyphenyl) hexanol, 6- (3-t-butyl-4-hydroxy-5-methylphenyl) hexanol, 6- (3-t-butyl-
2-hydroxy-5-methylphenyl) hexanol,
6- (5-tert-butyl-2-hydroxy-3-methylphenyl) hexanol, 6- (3,5-di-tert-butyl-4-hydroxyphenyl) hexanol, 6- (3
5-di-t-butyl-2-hydroxyphenyl) hexanol and the like. These can be produced, for example, by reducing the corresponding phenylcarboxylic acids or their esters, benzaldehydes and the like according to known methods.

Representative examples of the hydroxy compound (XIII) when the linking group X is a group represented by the formula (III) include, for example,
2- (3-t-butyl-2-hydroxyphenylmethyloxy)
Ethanol, 2- (3-t-butyl-4-hydroxyphenylmethyloxy) ethanol, 2- (3-t-butyl-2-hydroxy-5-methylphenylmethyloxy) ethanol, 2-
(3,5-di-t-butyl-2-hydroxyphenylmethyloxy) ethanol, 2- (3-t-butyl-4-hydroxy-5-methylphenylmethyloxy) ethanol, 2- (3,5-diphenyl -t
-Butyl-4-hydroxyphenylmethyloxy) ethanol, 2- (2-methyl-3,5-di-t-butyl-4-hydroxyphenylmethyloxy) ethanol, 2- (3-t-butyl-2)
-Methoxyphenylmethyloxy) ethanol, 2- (3-
t-butyl-4-methoxyphenylmethyloxy) ethanol, 2- (3-t-butyl-2-methoxy-5-methylphenylmethyloxy) ethanol,

2- (3,5-di-t-butyl-2-methoxyphenylmethyloxy) ethanol, 2- (3-t-butyl-4-methoxy-5-methylphenylmethyloxy) ethanol,
(3,5-di-t-butyl-4-methoxyphenylmethyloxy)
Ethanol, 2- (2-methyl-3,5-di-t-butyl-4-methoxyphenylmethyloxy) ethanol, 3- (3-t-butyl-2-hydroxyphenylmethyloxy) propanol, 3- (3 -t-butyl-4-hydroxyphenylmethyloxy) propanol, 3- (3-t-butyl-2-hydroxy-5-
Methylphenylmethyloxy) propanol, 3- (3,5-
Di-t-butyl-2-hydroxyphenylmethyloxy) propanol, 3- (3-t-butyl-4-hydroxy-5-methylphenylmethyloxy) propanol, 3- (3,5-di-t-
Butyl-4-hydroxyphenylmethyloxy) propanol,

3- (2-methyl-3,5-di-t-butyl-4-hydroxyphenylmethyloxy) propanol, 3- (3-t-
Butyl-2-methoxyphenylmethyloxy) propanol, 2- (3-t-butyl-4-methoxyphenylmethyloxy)
Propanol, 2- (3-t-butyl-2-methoxy-5-methylphenylmethyloxy) propanol, 2- (3,5-di-t
-Butyl-2-methoxyphenylmethyloxy) propanol, 2- (3-t-butyl-4-methoxy-5-methylphenylmethyloxy) propanol, 3- (3,5-di-t-butyl-4)
-Methoxyphenylmethyloxy) propanol, 3- (2
-Methyl-3,5-di-t-butyl-4-methoxyphenylmethyloxy) propanol, 4- (3-t-butyl-2-hydroxyphenylmethyloxy) butanol, 4- (3-t-butyl
-4-hydroxyphenylmethyloxy) butanol,

4- (3-t-butyl-2-hydroxy-5-methylphenylmethyloxy) butanol, 4- (3,5-di-t-butyl-2-hydroxyphenylmethyloxy) butanol, 4- ( 3-t-butyl-4-hydroxy-5-methylphenylmethyloxy) butanol, 4- (3,5-di-t-butyl-4-
(Hydroxyphenylmethyloxy) butanol, 4- (2-
Methyl-3,5-di-t-butyl-4-hydroxyphenylmethyloxy) butanol, 4- (3-t-butyl-2-methoxyphenylmethyloxy) butanol, 2- (3-t-butyl-4-
Methoxyphenylmethyloxy) butanol, 2- (3-t-
Butyl-2-methoxy-5-methylphenylmethyloxy)
Butanol, 2- (3,5-di-t-butyl-2-methoxyphenylmethyloxy) butanol, 2- (3-t-butyl-4-methoxy-5-methylphenylmethyloxy) butanol, 4-
(3,5-di-t-butyl-4-methoxyphenylmethyloxy) butanol, 4- (2-methyl-3,5-di-t-butyl-4-
Methoxyphenylmethyloxy) butanol. When A is methylene, for example, by reacting the corresponding diol with the corresponding phenol compound and formaldehyde, or when A is an alkylene other than methylene Can be produced, for example, by reacting a corresponding diol with a corresponding halide compound.

When the linking group X is a group represented by the formula (IV), typical examples of the hydroxy compound (XIII) include, for example, 3-tert-butyl-2-hydroxybenzoic acid, 3-tert-butyl-4 -Hydroxybenzoic acid, 5-t-butyl-2-
Hydroxybenzoic acid, 3-t-pentyl-4-hydroxybenzoic acid, 3-t-octyl-4-hydroxybenzoic acid, 3-cyclohexyl-4-hydroxybenzoic acid, 3
-(1-methylcyclohexyl) -4-hydroxybenzoic acid, 3-t-butyl-2-hydroxy-5-methylbenzoic acid, 3-t-butyl-4-hydroxy-5-methylbenzoic acid, 5-t- Butyl-2-hydroxy-3-methylbenzoic acid, 3-t-pentyl-4-hydroxy-5
Methylbenzoic acid, 3-t-octyl-4-hydroxy-
5-methylbenzoic acid, 3-cyclohexyl-4-hydroxy-5-methylbenzoic acid, 3- (1-methylcyclohexyl) -4-hydroxy-5-methylbenzoic acid, 3-
t-butyl-4-hydroxy-5-ethylbenzoic acid, 3
-T-pentyl-4-hydroxy-5-ethylbenzoic acid, 3-t-octyl-4-hydroxy-5-ethylbenzoic acid, 3-cyclohexyl-4-hydroxy-5-ethylbenzoic acid,

3- (1-methylcyclohexyl) -4-
Hydroxy-5-ethylbenzoic acid, 3,5-di-t-butyl-2-hydroxybenzoic acid, 3,5-di-t-butyl-4-hydroxybenzoic acid, 3-t-pentyl-4-
Hydroxy-5-t-butylbenzoic acid, 3-t-octyl-4-hydroxy-5-t-butylbenzoic acid, 3-
Cyclohexyl-4-hydroxy-5-t-butylbenzoic acid, 3- (1-methylcyclohexyl) -4-hydroxy-5-t-butylbenzoic acid, 3-t-butyl-2-
Methoxybenzoic acid, 3-tert-butyl-4-methoxybenzoic acid, 3-tert-butyl-5-methoxybenzoic acid, 3-
t-pentyl-4-methoxybenzoic acid, 3-t-octyl-4-methoxybenzoic acid, 3-cyclohexyl-4-
Methoxybenzoic acid, 3- (1-methylcyclohexyl)
-4-methoxybenzoic acid, 3-tert-butyl-2-methoxy-5-methylbenzoic acid, 3-tert-butyl-4-methoxy-5-methylbenzoic acid, 5-tert-butyl-2-methoxy-3 -Methylbenzoic acid, 3-t-pentyl-4-methoxy-5-methylbenzoic acid, 3-t-octyl-4-methoxy-5-methylbenzoic acid, 3-cyclohexyl-
4-methoxy-5-methylbenzoic acid, 3- (1-methylcyclohexyl) -4-methoxy-5-methylbenzoic acid, 3-t-butyl-4-methoxy-5-ethylbenzoic acid, 3-t-pentyl -4-methoxy-5-ethylbenzoic acid, 3-t-octyl-4-methoxy-5-ethylbenzoic acid, 3-cyclohexyl-4-methoxy-5-ethylbenzoic acid,

3- (1-methylcyclohexyl) -4-
Methoxy-5-ethylbenzoic acid, 3,5-di-t-butyl-2-methoxybenzoic acid, 3,5-di-t-butyl-
4-methoxybenzoic acid, 3-tert-pentyl-4-methoxy-5-tert-butylbenzoic acid, 3-tert-octyl-4-
Methoxy-5-t-butylbenzoic acid, 3-cyclohexyl-4-methoxy-5-t-butylbenzoic acid, 3-
(3- (1-methylcyclohexyl) -4-methoxy-
5-tert-butylbenzoic acid, 3-tert-butyl-2-ethoxybenzoic acid, 3-tert-butyl-4-ethoxybenzoic acid,
3-tert-butyl-4-ethoxy-5-methylbenzoic acid,
3-tert-butyl-2-ethoxy-5-methylbenzoic acid,
5-tert-butyl-2-ethoxy-3-methylbenzoic acid,
3,5-di-t-butyl-4-ethoxybenzoic acid, 3,
5-di-t-butyl-2-ethoxybenzoic acid, (3-t
-Butyl-2-hydroxyphenyl) acetic acid, (3-t-
(Butyl-4-hydroxyphenyl) acetic acid, (5-t-butyl-2-hydroxyphenyl) acetic acid, (3-t-pentyl-4-hydroxyphenyl) acetic acid, (3-t-octyl-4-hydroxyphenyl) acetic acid , (3-cyclohexyl-4-hydroxyphenyl) acetic acid, [3- (1-
Methylcyclohexyl) -4-hydroxyphenyl] acetic acid, (3-t-butyl-2-hydroxy-5-methylphenyl) acetic acid, (3-t-butyl-4-hydroxy-5)
-Methylphenyl) acetic acid,

(5-t-butyl-2-hydroxy-3-
(Methylphenyl) acetic acid, (3-t-pentyl-4-hydroxy-5-methylphenyl) acetic acid, (3-t-octyl-4-hydroxy-5-methylphenyl) acetic acid, (3
-Cyclohexyl-4-hydroxy-5-methylphenyl) acetic acid, [3- (1-methylcyclohexyl) -4-
[Hydroxy-5-methylphenyl] acetic acid, (3-t-butyl-4-hydroxy-5-ethylphenyl) acetic acid,
(3-t-pentyl-4-hydroxy-5-ethylphenyl) acetic acid, (3-t-octyl-4-hydroxy-5)
-Ethylphenyl) acetic acid, (3-cyclohexyl-4-
Hydroxy-5-ethylphenyl) acetic acid, [3- (1-
Methylcyclohexyl) -4-hydroxy-5-ethylphenyl] acetic acid, (3,5-di-t-butyl-2-hydroxyphenyl) acetic acid, (3,5-di-t-butyl-4)
-Hydroxyphenyl) acetic acid, (3-t-pentyl-4)
-Hydroxy-5-t-butylphenyl) acetic acid, (3-
t-octyl-4-hydroxy-5-t-butylphenyl) acetic acid, (3-cyclohexyl-4-hydroxy-5)
-T-butylphenyl) acetic acid,

[3- (1-methylcyclohexyl) -4
-Hydroxy-5-t-butylphenyl] acetic acid, (3-
t-butyl-2-methoxyphenyl) acetic acid, (3-t-
(Butyl-4-methoxyphenyl) acetic acid, (3-t-butyl-5-methoxyphenyl) acetic acid, (3-t-pentyl-4-methoxyphenyl) acetic acid, (3-t-octyl-4-methoxyphenyl) Acetic acid, (3-cyclohexyl-4-methoxyphenyl) acetic acid, [3- (1-methylcyclohexyl) -4-methoxyphenyl] acetic acid, (3-
t-butyl-2-methoxy-5-methylphenyl) acetic acid, (3-t-butyl-4-methoxy-5-methylphenyl) acetic acid, (5-t-butyl-2-methoxy-3-methylphenyl) acetic acid , (3-t-pentyl-4-methoxy-5-methylphenyl) acetic acid, (3-t-octyl-
4-methoxy-5-methylphenyl) acetic acid, (3-cyclohexyl-4-methoxy-5-methylphenyl) acetic acid, [3- (1-methylcyclohexyl) -4-methoxy-5-methylphenyl] acetic acid, (3 -T-butyl-4
-Methoxy-5-ethylphenyl) acetic acid, (3-t-pentyl-4-methoxy-5-ethylphenyl) acetic acid,
(3-t-octyl-4-methoxy-5-ethylphenyl) acetic acid, (3-cyclohexyl-4-methoxy-5-
Ethylphenyl) acetic acid, [3- (1-methylcyclohexyl) -4-methoxy-5-ethylphenyl] acetic acid,
(3,5-di-t-butyl-2-methoxyphenyl) acetic acid,

(3,5-di-tert-butyl-4-methoxyphenyl) acetic acid, (3-tert-pentyl-4-methoxy-)
5-t-butylphenyl) acetic acid, (3-t-octyl-
4-methoxy-5-t-butylphenyl) acetic acid, (3-
Cyclohexyl-4-methoxy-5-t-butylphenyl) acetic acid, [3- (1-methylcyclohexyl) -4-
[Methoxy-5-t-butylphenyl] acetic acid, (3-t-
Butyl-2-ethoxyphenyl) acetic acid, (3-t-butyl-4-ethoxyphenyl) acetic acid, (3-t-butyl-acetic acid)
4-ethoxy-5-methylphenyl) acetic acid, (3-t-
Butyl-2-ethoxy-5-methylphenyl) acetic acid,
(5-tert-butyl-2-ethoxy-3-methylphenyl) acetic acid, (3,5-di-tert-butyl-4-ethoxyphenyl) acetic acid, (3,5-di-tert-butyl-2-ethoxy) Phenyl) acetic acid, 3- (3-t-butyl-2-hydroxyphenyl) propionic acid, 3- (3-t-butyl-
4-hydroxyphenyl) propionic acid, 3- (5-t
-Butyl-2-hydroxyphenyl) propionic acid, 3
-(3-t-pentyl-4-hydroxyphenyl) propionic acid, 3- (3-t-octyl-4-hydroxyphenyl) propionic acid, 3- (3-cyclohexyl-4)
-Hydroxyphenyl) propionic acid, 3- [3- (1
-Methylcyclohexyl) -4-hydroxyphenyl]
Propionic acid, 3- (3-t-butyl-2-hydroxy-5-methylphenyl) propionic acid, 3- (3-t-
Butyl-4-hydroxy-5-methylphenyl) propionic acid, 3- (5-tert-butyl-2-hydroxy-3-
Methylphenyl) propionic acid,

3- (3-t-pentyl-4-hydroxy-5-methylphenyl) propionic acid;
Octyl-4-hydroxy-5-methylphenyl) propionic acid, 3- (3-cyclohexyl-4-hydroxy-5-methylphenyl) propionic acid, 3- [3- (1
-Methylcyclohexyl) -4-hydroxy-5-methylphenyl] propionic acid, 3- (3-tert-butyl-
4-hydroxy-5-ethylphenyl) propionic acid,
3- (3-t-pentyl-4-hydroxy-5-ethylphenyl) propionic acid, 3- (3-t-octyl-4
-Hydroxy-5-ethylphenyl) propionic acid, 3
-(3-cyclohexyl-4-hydroxy-5-ethylphenyl) propionic acid, 3- [3- (1-methylcyclohexyl) -4-hydroxy-5-ethylphenyl]
Propionic acid, 3- (3,5-di-t-butyl-2-hydroxyphenyl) propionic acid, 3- (3,5-di-
t-butyl-4-hydroxyphenyl) propionic acid,
3- (3-t-pentyl-4-hydroxy-5-t-butylphenyl) propionic acid, 3- (3-t-octyl-4-hydroxy-5-t-butylphenyl) propionic acid, 3- (3 -Cyclohexyl-4-hydroxy-5
-T-butylphenyl) propionic acid, 3- [3- (1
-Methylcyclohexyl) -4-hydroxy-5-t-
Butylphenyl] propionic acid, 3- (3-t-butyl-2-methoxyphenyl) propionic acid,

3- (3-tert-butyl-4-methoxyphenyl) propionic acid, 3- (3-tert-butyl-5-methoxyphenyl) propionic acid, 3- (3-tert-pentyl-4-methoxyphenyl) ) Propionic acid, 3- (3-t
-Octyl-4-methoxyphenyl) propionic acid, 3
-(3-cyclohexyl-4-methoxyphenyl) propionic acid, 3- [3- (1-methylcyclohexyl)-
4-methoxyphenyl] propionic acid, 3- (3-t-
Butyl-2-methoxy-5-methylphenyl) propionic acid, 3- (3-t-butyl-4-methoxy-5-methylphenyl) propionic acid, 3- (5-t-butyl-2)
-Methoxy-3-methylphenyl) propionic acid, 3-
(3-t-pentyl-4-methoxy-5-methylphenyl) propionic acid, 3- (3-t-octyl-4-methoxy-5-methylphenyl) propionic acid, 3- (3-
Cyclohexyl-4-methoxy-5-methylphenyl)
Propionic acid, 3- [3- (1-methylcyclohexyl) -4-methoxy-5-methylphenyl] propionic acid, 3- (3-t-butyl-4-methoxy-5-ethylphenyl) propionic acid, 3- (3-t-pentyl-4
-Methoxy-5-ethylphenyl) propionic acid, 3-
(3-t-octyl-4-methoxy-5-ethylphenyl) propionic acid, 3- (3-cyclohexyl-4-methoxy-5-ethylphenyl) propionic acid, 3- [3
-(1-methylcyclohexyl) -4-methoxy-5-
Ethylphenyl] propionic acid,

3- (3,5-di-tert-butyl-2-methoxyphenyl) propionic acid, 3- (3,5-di-tert-propionate)
Butyl-4-methoxyphenyl) propionic acid, 3-
(3-t-pentyl-4-methoxy-5-t-butylphenyl) propionic acid, 3- (3-t-octyl-4-)
Methoxy-5-t-butylphenyl) propionic acid, 3
-(3-cyclohexyl-4-methoxy-5-t-butylphenyl) propionic acid, 3- [3- (1-methylcyclohexyl) -4-methoxy-5-t-butylphenyl] propionic acid, 3- (3 -Tert-butyl-2-ethoxyphenyl) propionic acid, 3- (3-tert-butyl-4)
-Ethoxyphenyl) propionic acid, 3- (3-t-butyl-4-ethoxy-5-methylphenyl) propionic acid, 3- (3-t-butyl-2-ethoxy-5-methylphenyl) propionic acid, 3 -(5-t-butyl-2-
Ethoxy-3-methylphenyl) propionic acid, 3-
(3,5-di-t-butyl-4-ethoxyphenyl) propionic acid, 3- (3,5-di-t-butyl-2-ethoxyphenyl) propionic acid, 3- (3-t-butyl-
2-hydroxyphenyl) butanoic acid, 3-
(3-t-butyl-4-hydroxyphenyl) butanoic acid, 3- (3-t-butyl-4-hydroxy-5-methylphenyl) butanoic acid, 3-
(3-t-butyl-2-hydroxy-5-methylphenyl) butanoic acid,

3- (5-tert-butyl-2-hydroxy-
3-methylphenyl) butanoic acid, 3-
(3,5-di-t-butyl-4-hydroxyphenyl)
Butanoic acid, 3- (3,5-di-t-butyl-2-hydroxyphenyl) butanoic acid, 3
-(3-t-butyl-2-methoxyphenyl) butanoic acid, 3- (3-t-butyl-4-methoxyphenyl) butanoic acid, 3- (3-t-butyl-4-methoxy-) 5- (methylphenyl) butanoic acid, 3- (3-t-butyl-2-methoxy-5-methylphenyl) butanoic acid, 3- (5-t-acid)
Butyl-2-methoxy-3-methylphenyl) butanoic acid, 3- (3,5-di-t-butyl-4-methoxyphenyl) butanoic acid, 3- (3,5
Carboxyls such as -di-t-butyl-2-methoxyphenyl) butanoic acid.

In the case where A is a mere bond, for example, the corresponding carboxylic acids are prepared by converting the corresponding hydroxybenzoic acid, alkoxybenzoic acid, aralkyloxybenzoic acid or the like to Friedel using a catalyst such as aluminum chloride or zinc chloride. When Z is a hydroxy group, an alkoxy group, or an aralkyloxy group, a corresponding phenol, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, and carbon dioxide can be produced. It can be produced by a Kolbe-Schmidt reaction according to the methods described in JP-A-62-61949 and JP-A-63-165341. When A is an alkylene having 1 to 8 carbon atoms, the corresponding phenol is converted to a free phenol such as aluminum chloride or zinc chloride in accordance with the method described in Rubber Chemistry and Technology 46 , 96 (1973). After acylation using a Del-Crafts catalyst and a carboalkoxyalkanoyl halogenoid, the carbonyl group at the benzyl position is reduced to alkylene with a hydrogenation catalyst such as palladium charcoal or platinum charcoal, and then the ester is hydrolyzed with an acid or alkali. It can be produced by decomposition.

Representative examples of the hydroxy compound (XIII) when the linking group X is a group represented by the formula (V) include, for example, 2-hydroxyethyl benzoate and 3-t-butyl-2-hydroxybenzoic acid 2 -Hydroxyethyl, 3-t-butyl-4-hydroxybenzoic acid 2-hydroxyethyl, 3-t-butyl-5-
2-hydroxyethyl hydroxybenzoate, 3-t-pentyl-4-hydroxybenzoate 2-hydroxyethyl, 3-t-
2-hydroxyethyl octyl-4-hydroxybenzoate, 2-hydroxyethyl 3-cyclohexyl-4-hydroxybenzoate, 2-hydroxyethyl 3- (1-methylcyclohexyl) -4-hydroxybenzoate, 3-t-butyl -2-
2-hydroxyethyl hydroxy-5-methylbenzoate, 3-t-butyl-4-hydroxy-5-methylbenzoic acid 2-
Hydroxyethyl, 3-t-butyl-4-hydroxy-5-methylbenzoic acid 3-hydroxypropyl, 3-t-butyl-4-hydroxy-5-methylbenzoic acid 4-hydroxybutyl, 5-
2-hydroxyethyl t-butyl-2-hydroxy-3-methylbenzoate, 3t-pentyl-4-hydroxy-5-methylbenzoic acid 2-hydroxyethyl, 3-t-octyl-4-hydroxy-5-methylbenzoic acid 2-hydroxyethyl, 3-cyclohexyl-4-hydroxy-5-methylbenzoic acid 2-hydroxyethyl, 3- (1-methylcyclohexyl) -4-hydroxy-5-methylbenzoic acid 2-hydroxyethyl, 3-t
-2-hydroxyethyl butyl-4-hydroxy-5-ethylbenzoate, 2-hydroxyethyl 3-tert-pentyl-4-hydroxy-5-ethylbenzoate, 3-t-octyl-4-hydroxy-5-ethyl 2-hydroxyethyl benzoate,

2-hydroxyethyl 3-cyclohexyl-4-hydroxy-5-ethylbenzoate, 2-hydroxyethyl 3- (1-methylcyclohexyl) -4-hydroxy-5-ethylbenzoate, 3,5-di- 2-hydroxyethyl t-butyl-2-hydroxybenzoate, 3,5-di-t-butyl-4-
2-hydroxyethyl hydroxybenzoate, 3,5-di-t
-Butyl-4-hydroxybenzoic acid 3-hydroxypropyl, 3,5-di-t-butyl-4-hydroxybenzoic acid 4-hydroxybutyl, 3-t-pentyl-4-hydroxy-5-t-butylbenzoic acid 2 -Hydroxyethyl, 3-t-octyl-4-
2-hydroxyethyl hydroxy-5-t-butylbenzoate, 3-cyclohexyl-4-hydroxy-5-t-butylbenzoic acid 2-hydroxyethyl, 3- (3- (1-methylcyclohexyl) -4-hydroxy- 2-hydroxyethyl 5-t-butylbenzoate (3-t-butyl-4-hydroxyphenyl) acetic acid 2-hydroxyethyl, (3-t-butyl-5-hydroxyphenyl) acetic acid 2-hydroxyethyl, (3 -t-pentyl-4-hydroxyphenyl) acetic acid 2-hydroxyethyl, (3t-octyl-4-hydroxyphenyl) acetic acid 2-hydroxyethyl, (3-cyclohexyl-4-hydroxyphenyl) acetic acid
2-hydroxyethyl, [3- (1-methylcyclohexyl)
-4-hydroxyphenyl] 2-hydroxyethyl acetate,
(3-t-butyl-2-hydroxy-5-methylphenyl) acetic acid
2-hydroxyethyl,

2-Hydroxyethyl (3-t-butyl-4-hydroxy-5-methylphenyl) acetic acid, (3-t-butyl-4-methyl-4-methylphenyl) acetate
3-hydroxypropyl hydroxy-5-methylphenyl) acetate, 4-hydroxybutyl (3-t-butyl-4-hydroxy-5-methylphenyl) acetate, (5-t-butyl-2-hydroxy-3-methylphenyl) ) 2-Hydroxyethyl acetate, (3-t-pentyl-4-hydroxy-5-methylphenyl) acetic acid 2-hydroxyethyl, (3-t-octyl-4-hydroxy-5-methylphenyl) acetic acid 2-hydroxyethyl 2-hydroxyethyl (3-cyclohexyl-4-hydroxy-5-methylphenyl) acetic acid, [3- (1-methylcyclohexyl) -4-hydroxy-5-methylphenyl] acetic acid 2
-Hydroxyethyl, (3-t-butyl-4-hydroxy-5-
Ethylphenyl) acetic acid 2-hydroxyethyl, (3-t-pentyl-4-hydroxy-5-ethylphenyl) acetic acid 2-hydroxyethyl, (3-t-octyl-4-hydroxy-5-ethylphenyl) acetic acid 2- Hydroxyethyl, (3-cyclohexyl-4-hydroxy-5-ethylphenyl) acetic acid 2-
Hydroxyethyl, [3- (1-methylcyclohexyl) -4-
[Hydroxy-5-ethylphenyl] 2-hydroxyethyl acetate, (3,5-di-t-butyl-2-hydroxyphenyl) acetic acid 2-hydroxyethyl, (3,5-di-t-butyl-4-hydroxyphenyl) ) 2-Hydroxyethyl acetate, (3,5-di
3-hydroxypropyl (3-t-butyl-4-hydroxyphenyl) acetic acid, 4-hydroxybutyl (3,5-di-t-butyl-4-hydroxyphenyl) acetate,

2-hydroxyethyl (3-t-pentyl-4-hydroxy-5-t-butylphenyl) acetate, (3-t-octyl)
4-hydroxy-5-t-butylphenyl) acetic acid 2-hydroxyethyl, (3-cyclohexyl-4-hydroxy-5-t-
2-hydroxyethyl butylphenyl) acetate, [3- (1-methylcyclohexyl) -4-hydroxy-5-t-butylphenyl] acetic acid 2-hydroxyethyl 3- (3-t-butyl-2-hydroxyphenyl) propion 2-hydroxyethyl 3-, 3- (3-t-butyl-4-hydroxyphenyl) propionate 2-hydroxyethyl 3- (3-t-butyl-5-hydroxyphenyl) propionate, 2
2-hydroxyethyl 3- (3-t-pentyl-4-hydroxyphenyl) propionate, 2-hydroxyethyl 3- (3-t-octyl-4-hydroxyphenyl) propionate,
2-hydroxyethyl 3- (3-cyclohexyl-4-hydroxyphenyl) propionate, 2-hydroxyethyl 3- [3- (1-methylcyclohexyl) -4-hydroxyphenyl] propionate, 3- (3-t- Butyl-2-hydroxy-5-methylphenyl) 2-hydroxyethyl propionate, 3-hydroxyethyl
2-hydroxyethyl (3-t-butyl-4-hydroxy-5-methylphenyl) propionate, 3-hydroxybutyl 3- (3-t-butyl-4-hydroxy-5-methylphenyl) propionate 4-hydroxybutyl (3-t-butyl-4-hydroxy-5-methylphenyl) propionate,

3- (5-t-butyl-2-hydroxy-3-methylphenyl) propionic acid 2-hydroxyethyl, 3- (3-t
-2-hydroxyethyl pentyl-4-hydroxy-5-methylphenyl) propionate, 2-hydroxyethyl 3- (3-t-octyl-4-hydroxy-5-methylphenyl) propionate, 3- (3-cyclohexyl- 4-hydroxy-5-methylphenyl) 2-hydroxyethyl propionate, 3-hydroxyethyl
[3- (1-methylcyclohexyl) -4-hydroxy-5-methylphenyl] 2-hydroxyethyl propionate, 3- (3
2-hydroxyethyl 3-t-butyl-4-hydroxy-5-ethylphenyl) propionate, 2-hydroxyethyl 3- (3-t-pentyl-4-hydroxy-5-ethylphenyl) propionate, 3- (3 -t-octyl-4-hydroxy-5-ethylphenyl) propionic acid 2-hydroxyethyl, 3- (3
-Cyclohexyl-4-hydroxy-5-ethylphenyl)
2-hydroxyethyl propionate, 3- [3- (1-methylcyclohexyl) -4-hydroxy-5-ethylphenyl] 2-hydroxyethyl propionate, 3- (3,5-di-t-butyl-2- 2-hydroxyethyl) hydroxyphenyl) propionate, 2-hydroxyethyl 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate, 3- (3,5-di-t-
3-hydroxypropyl butyl-4-hydroxyphenyl) propionate, 4-hydroxybutyl 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate,

2-hydroxyethyl 3- (3-t-pentyl-4-hydroxy-5-t-butylphenyl) propionate
(3-t-octyl-4-hydroxy-5-t-butylphenyl)
2-hydroxyethyl propionate, 3- (3-cyclohexyl-4-hydroxy-5-t-butylphenyl) propionate, 2-hydroxyethyl propionate, 3- [3- (1-methylcyclohexyl) -4-hydroxy-5- t-butylphenyl] 2-hydroxyethyl propionate, 2-hydroxyethyl 4- (3-t-butyl-2-hydroxyphenyl) butyrate, 4- (3tbutyl-
4-hydroxyphenyl) butyric acid 2-hydroxyethyl, 4
2-hydroxyethyl 4- (3-t-butyl-4-hydroxy-5-methylphenyl) butyrate, 3-hydroxypropyl 4- (3-t-butyl-4-hydroxy-5-methylphenyl) butyrate,
4- (3-t-butyl-4-hydroxy-5-methylphenyl) butyric acid 4-hydroxybutyl, 4- (3-t-butyl-2-hydroxy-5-methylphenyl) butyric acid 2-hydroxyethyl,
(5-t-butyl-2-hydroxy-3-methylphenyl) butyric acid
2-hydroxyethyl, 4- (3,5-di-t-butyl-4-hydroxyphenyl) butyrate 2-hydroxyethyl, 4- (3,5-
3-hydroxypropyl di-t-butyl-4-hydroxyphenyl) butyrate, 4-hydroxybutyl 4- (3,5-di-t-butyl-4-hydroxyphenyl) butyrate, 4- (3,5-di- 2-hydroxyethyl t-butyl-2-hydroxyphenyl) butyrate,

2-hydroxyethyl 3-tert-butyl-2-methoxybenzoate, 2-hydroxyethyl 3-tert-butyl-4-methoxybenzoate, 2-hydroxyethyl 3-tert-butyl-5-methoxybenzoate
Hydroxyethyl, 3-t-pentyl-4-methoxybenzoic acid
2-hydroxyethyl, 3-t-octyl-4-methoxybenzoic acid 2-hydroxyethyl, 3-cyclohexyl-4-methoxybenzoic acid 2-hydroxyethyl, 3- (1-methylcyclohexyl) -4-methoxybenzoic acid 2 -Hydroxyethyl, 3-t-butyl-2-methoxy-5-methylbenzoic acid 2-
Hydroxyethyl, 3-t-butyl-4-methoxy-5-methylbenzoic acid 2-hydroxyethyl, 3-t-butyl-4-methoxy-5-methylbenzoic acid 3-hydroxypropyl, 3-t-butyl-4 -Methoxy-5-methylbenzoic acid 4-hydroxybutyl, 5-t-butyl-2-methoxy-3-methylbenzoic acid 2-
2-hydroxyethyl, 3-t-pentyl-4-methoxy-5-methylbenzoic acid 2-hydroxyethyl, 3-t-octyl-4-methoxy-5-methylbenzoic acid
2-hydroxyethyl cyclohexyl-4-methoxy-5-methylbenzoate, 2-hydroxyethyl 3- (1-methylcyclohexyl) -4-methoxy-5-methylbenzoate, 3-t
-Butyl-4-methoxy-5-ethylbenzoic acid 2-hydroxyethyl,

2-hydroxyethyl 3-t-pentyl-4-methoxy-5-ethylbenzoate, 3-t-octyl-4-methoxy
2-hydroxyethyl-5-ethylbenzoate, 3-hydroxyhexyl-4-methoxy-5-hydroxyethyl-2-ethylbenzoate, 3- (1-methylcyclohexyl) -4-methoxy
-5-Ethylbenzoic acid 2-hydroxyethyl, 3,5-di-t
-2-hydroxyethyl butyl-2-methoxybenzoate,
3,5-di-t-butyl-4-methoxybenzoic acid 2-hydroxyethyl, 3,5-di-t-butyl-4-methoxybenzoic acid 3
-Hydroxypropyl, 4-hydroxybutyl 3,5-di-t-butyl-4-methoxybenzoate, 2-hydroxyethyl 3-tert-pentyl-4-methoxy-5-t-butylbenzoate,
2-Hydroxyethyl t-octyl-4-methoxy-5-t-butylbenzoate, 3-cyclohexyl-4-methoxy-5-t-
2-hydroxyethyl butylbenzoate, 3- (3- (1-methylcyclohexyl) -4-methoxy-5-t-butylbenzoic acid 2
-Hydroxyethyl, 3-t-butyl-2-ethoxybenzoic acid
2-hydroxyethyl, 3-t-butyl-4-ethoxybenzoic acid 2-hydroxyethyl, 3-t-butyl-4-ethoxy-5-
2-hydroxyethyl methylbenzoate, 3-t-butyl-4-
3-hydroxypropyl ethoxy-5-methylbenzoate,
4-hydroxybutyl 3-t-butyl-4-ethoxy-5-methylbenzoate,

2-hydroxyethyl 3-tert-butyl-2-ethoxy-5-methylbenzoate, 5-tert-butyl-2-ethoxy-3-
2-hydroxyethyl methylbenzoate, 2-hydroxyethyl 3,5-di-t-butyl-4-ethoxybenzoate,
2-hydroxyethyl 5-di-t-butyl-2-ethoxybenzoate, 2-hydroxyethyl (3-t-butyl-4-methoxyphenyl) acetate, (3-t-butyl-5-methoxyphenyl)
2-hydroxyethyl acetate, 2-hydroxyethyl (3-t-pentyl-4-methoxyphenyl) acetate, 2-hydroxyethyl (3t-octyl-4-methoxyphenyl) acetate,
2-hydroxyethyl (3-cyclohexyl-4-methoxyphenyl) acetate, 2-hydroxyethyl [3- (1-methylcyclohexyl) -4-methoxyphenyl] acetate, (3-t-butyl-2-methoxy-5- Methylphenyl) acetic acid 2-hydroxyethyl, (3-t-butyl-4-methoxy-5-methylphenyl) acetic acid 2-hydroxyethyl, (3-t-butyl-4-methoxy-5-methylphenyl) acetic acid 3- Hydroxypropyl, 4-hydroxybutyl (3-t-butyl-4-methoxy-5-methylphenyl) acetate, (5-t-butyl-2-methoxy-3)
-Methylphenyl) acetic acid 2-hydroxyethyl, (3-t-
Pentyl-4-methoxy-5-methylphenyl) acetic acid 2-hydroxyethyl, (3-t-octyl-4-methoxy-5-methylphenyl) acetic acid 2-hydroxyethyl, (3-cyclohexyl-4-methoxy-5-methyl) Methylphenyl) 2-hydroxyethyl acetate,

[3- (1-methylcyclohexyl) -4-methoxy-5-methylphenyl] 2-hydroxyethyl acetate,
(3-t-butyl-4-methoxy-5-ethylphenyl) acetic acid 2-
Hydroxyethyl, (3-t-pentyl-4-methoxy-5-
Ethylphenyl) acetic acid 2-hydroxyethyl, (3-t-octyl-4-methoxy-5-ethylphenyl) acetic acid 2-hydroxyethyl, (3-cyclohexyl-4-methoxy-5-ethylphenyl) acetic acid 2-hydroxyethyl , [3- (1-methylcyclohexyl) -4-methoxy-5-ethylphenyl]
2-hydroxyethyl acetate, (3,5-di-t-butyl-2-methoxyphenyl) acetic acid 2-hydroxyethyl, (3,5-diethyl
2-hydroxyethyl (3-t-butyl-4-methoxyphenyl) acetate, 3-hydroxypropyl (3,5-di-t-butyl-4-methoxyphenyl) acetate, (3,5-di-t-butyl-4) -Methoxyphenyl) acetic acid 4-hydroxybutyl, (3-t-pentyl-4-methoxy-5-t-butylphenyl) acetic acid 2-hydroxyethyl, (3-t-octyl-4-methoxy-5-t-butylphenyl) ) 2-Hydroxyethyl acetate, (3-cyclohexyl-4-methoxy-5-t-butylphenyl) acetic acid 2-hydroxyethyl, [3- (1-methylcyclohexyl) -4-methoxy-5-t-butylphenyl] 2-hydroxyethyl acetate, 2-hydroxyethyl (3-t-butyl-2-ethoxyphenyl) acetate,

(3-t-butyl-4-ethoxyphenyl) acetic acid
2-hydroxyethyl, (3-t-butyl-4-ethoxy-5-
Methylphenyl) acetic acid 2-hydroxyethyl, (3-t-butyl-4-ethoxy-5-methylphenyl) acetic acid 3-hydroxypropyl, (3-t-butyl-4-ethoxy-5-methylphenyl) acetic acid 4- Hydroxybutyl, (3-t-butyl-2-
2-hydroxyethyl ethoxy-5-methylphenyl) acetate, 2-hydroxyethyl (3-t-butyl-2-ethoxy-5-methylphenyl) acetate, (5-t-butyl-2-ethoxy-3)
-Methylphenyl) acetic acid 2-hydroxyethyl, (3,5-
2-hydroxyethyl di-t-butyl-4-ethoxyphenyl) acetate, (3,5-di-t-butyl-4-ethoxyphenyl)
3-hydroxypropyl acetate, (3,5-di-t-butyl-4-
4-hydroxybutyl ethoxyphenyl) acetate, (3,5-
2-hydroxyethyl di-t-butyl-2-ethoxyphenyl) acetate, 2-hydroxyethyl 3- (3-t-butyl-2-methoxyphenyl) propionate, 3- (3-t-butyl-4-methoxy) 2-hydroxyethyl phenyl) propionate,
3- (3-t-butyl-5-methoxyphenyl) propionic acid 2-
Hydroxyethyl, 2-hydroxyethyl 2-, (3-t-pentyl-4-methoxyphenyl) propionate, 3- (3-t
-2-hydroxyethyl octyl-4-methoxyphenyl) propionate, 2-hydroxyethyl 3- (3-cyclohexyl-4-methoxyphenyl) propionate,

2-hydroxyethyl 3- [3- (1-methylcyclohexyl) -4-methoxyphenyl] propionate
2-hydroxyethyl (3-t-butyl-2-methoxy-5-methylphenyl) propionate, 2-hydroxyethyl 3- (3-t-butyl-4-methoxy-5-methylphenyl) propionate, 3-hydroxybutyl 3- (3-t-butyl-4-methoxy-5-methylphenyl) propionate, 4- (3- (3-t-butyl-4-methoxy-5-methylphenyl) propionic acid
Hydroxybutyl, 3- (5-t-butyl-2-methoxy-3-methylphenyl) propionic acid 2-hydroxyethyl,
2-hydroxyethyl (3-t-pentyl-4-methoxy-5-methylphenyl) propionate, 3- (3-t-octyl-4-
2-hydroxyethyl methoxy-5-methylphenyl) propionate, 2-hydroxyethyl 3- (3-cyclohexyl-4-methoxy-5-methylphenyl) propionate
[3- (1-methylcyclohexyl) -4-methoxy-5-methylphenyl] 2-hydroxyethyl propionate, 3- (3-t
-2-hydroxyethyl butyl-4-methoxy-5-ethylphenyl) propionate, 2-hydroxyethyl 3- (3-t-pentyl-4-methoxy-5-ethylphenyl) propionate, 3- (3-t -2-hydroxyethyl octyl-4-methoxy-5-ethylphenyl) propionate, 2-hydroxyethyl 3- (3-cyclohexyl-4-methoxy-5-ethylphenyl) propionate, 3- [3- (1- Methylcyclohexyl) -4-methoxy-5-ethylphenyl] propionic acid 2-
Hydroxyethyl, 3- (3,5-di-t-butyl-2-methoxyphenyl) propionic acid 2-hydroxyethyl,
2-hydroxyethyl (3,5-di-t-butyl-4-methoxyphenyl) propionate,

3-hydroxypropyl 3- (3,5-di-t-butyl-4-methoxyphenyl) propionate
4-t-butyl-4-methoxyphenyl) propionate 4-hydroxybutyl, 3- (3-t-pentyl-4-methoxy-5-t-
Butylphenyl) 2-hydroxyethyl propionate, 3
-(3-t-octyl-4-methoxy-5-t-butylphenyl)
2-hydroxyethyl propionate, 3- (3-cyclohexyl-4-methoxy-5-t-butylphenyl) propionic acid
2-hydroxyethyl, 3- [3- (1-methylcyclohexyl) -4-methoxy-5-t-butylphenyl] propionic acid
2-hydroxyethyl, 3- (3-t-butyl-2-ethoxyphenyl) propionate 2-hydroxyethyl, 3- (3-t-
2-hydroxyethyl butyl-4-ethoxyphenyl) propionate, 2-hydroxyethyl 3- (3-t-butyl-4-ethoxy-5-methylphenyl) propionate, 3- (3-t-
Butyl-4-ethoxy-5-methylphenyl) propionic acid
3-hydroxypropyl, 3- (3-t-butyl-2-ethoxy)
-5-methylphenyl) 4-hydroxybutyl propionate, 3- (5-t-butyl-2-ethoxy-3-methylphenyl)
2-hydroxyethyl propionate, 3- (3,5-di-t-butyl-4-ethoxyphenyl) propionate, 2-hydroxyethyl propionate, 3- (3,5-di-t-butyl-4-ethoxyphenyl) 3-hydroxypropyl propionate, 3- (3,5-di
4-hydroxybutyl 3-t-butyl-4-ethoxyphenyl) propionate, 2-hydroxyethyl 3- (3,5-di-t-butyl-2-ethoxyphenyl) propionate,

2-hydroxyethyl 4- (3-t-butyl-2-methoxyphenyl) butyrate, 2-hydroxyethyl 4- (3t-butyl-4-methoxyphenyl) butyrate, 4- (3-t-butyl-4)
-2-hydroxyethyl methoxy-5-methylphenyl) butyrate, 3-hydroxypropyl 4- (3-t-butyl-4-methoxy-5-methylphenyl) butyrate, 4- (3-t-butyl-4-
4-Hydroxybutyl methoxy-5-methylphenyl) butyrate, 4- (3-t-butyl-2-methoxy-5-methylphenyl)
2-hydroxyethyl butyrate, 2-hydroxyethyl 4- (5-t-butyl-2-methoxy-3-methylphenyl) butyrate
2-hydroxyethyl (3,5-di-t-butyl-4-methoxyphenyl) butyrate, 3-hydroxypropyl 4- (3,5-di-t-butyl-4-methoxyphenyl) butyrate, 4- (3 , 5-di-t-
Butyl-4-methoxyphenyl) butyric acid 4-hydroxybutyl, 4- (3,5-di-t-butyl-2-methoxyphenyl) butyric acid
2-hydroxyethyl, 4- (3-t-butyl-4-ethoxy-5
-Methylphenyl) butyric acid 2-hydroxyethyl, 4- (3-t
-3-hydroxypropyl butyl-4-ethoxy-5-methylphenyl) butyrate, 4-hydroxybutyl 4- (3-t-butyl-4-ethoxy-5-methylphenyl) butyrate, 4- (3,5-di
2-Hydroxyethyl butyrate, 4- (3,5-di-t-butyl-4-ethoxyphenyl) -t-butyl-4-ethoxyphenyl) butyrate
3-hydroxypropyl butyrate, 4- (3,5-di-t-butyl-4)
-4-hydroxybutyl ethoxyphenyl) butyrate. These can be produced, for example, by reacting the corresponding diol with the corresponding carboxylic acid, carboxylic acid ester, carboxylic acid halide or the like.

When the linking group X is a group represented by the formula (VI), typical examples of the hydroxy compound (XIII) include phenyl hydroxyacetate, benzyl hydroxyacetate, 2-hydroxyacetate and the like.
Phenyl hydroxypropionate, benzyl 2-hydroxypropionate, phenyl 3-hydroxypropionate,
Benzyl 3-hydroxypropionate, 2-hydroxy-2
-Phenyl methyl-propionate, benzyl 2-hydroxy-2-methylpropionate, phenyl 3-hydroxy-2-methylpropionate, benzyl 3-hydroxy-2-methylpropionate, phenyl 2-hydroxybutyrate, benzyl 2-hydroxybutyrate Phenyl 2-hydroxy-2-methylbutyrate,
Benzyl 2-hydroxy-2-methylbutyrate, 2-hydroxy-3
-Phenyl methyl butyrate, benzyl 2-hydroxy-3-methylbutyrate, phenyl 2-ethyl-2-hydroxybutyrate, benzyl 2-ethyl-2-hydroxybutyrate, phenyl 3-hydroxybutyrate, benzyl 3-hydroxybutyrate, 4-hydroxy Phenyl butyrate, benzyl 4-hydroxybutyrate, 2-hydroxy-4-
Phenyl methylpentanoate, benzyl 2-hydroxy-4-methylpentanoate, phenyl 2-hydroxyhexanoate,
Benzyl 2-hydroxyhexanoate and the like.

Representative examples of the hydroxy compound (XIII) when the linking group X is a group represented by the formula (VII) include, for example,
2- [N- (3-t-butyl-2-hydroxyphenylmethyl) amino] ethanol, 2- [N- (3-t-butyl-4-hydroxyphenylmethyl) amino] ethanol, 2- [N- ( 3-t-butyl-2
-Hydroxy-5-methylphenylmethyl) amino] ethanol, 2- [N- (3,5-di-t-butyl-2-hydroxyphenylmethyl) amino] ethanol, 2- [N- (3-t-butyl) -Four-
Hydroxy-5-methylphenylmethyl) amino] ethanol, 2- [N- (3,5-di-t-butyl-4-hydroxyphenylmethyl) amino] ethanol, 2- [N- (2-methyl-3, 5-di
-t-butyl-4-hydroxyphenylmethyl) amino] ethanol, 2- [N- (3-t-butyl-2-methoxyphenylmethyl) amino] ethanol, 2- [N- (3-t-butyl-4) -Methoxyphenylmethyl) amino] ethanol, 2- [N- (3-t-butyl-2-methoxy-5-methylphenylmethyl) amino]
Ethanol, 2- [N- (3,5-di-t-butyl-2-methoxyphenylmethyl) amino] ethanol, 2- [N- (3-t-butyl-4
-Methoxy-5-methylphenylmethyl) amino] ethanol, 2- [N- (3,5-di-t-butyl-4-methoxyphenylmethyl) amino] ethanol, 2- [N- (2-methyl-3 , 5-di-t
-Butyl-4-methoxyphenylmethyl) amino] ethanol, 2- [N- (3-t-butyl-2-hydroxyphenylmethyl) -N-methylamino] ethanol, 2- [N- (3-t-butyl)
-4-hydroxyphenylmethyl) -N-methylamino] ethanol,

2- [N- (3-t-butyl-2-hydroxy-5-methylphenylmethyl) -N-methylamino] ethanol, 2-
[N- (3,5-di-t-butyl-2-hydroxyphenylmethyl)
-N-methylamino] ethanol, 2- [N- (3-t-butyl-4-
Hydroxy-5-methylphenylmethyl) -N-methylamino] ethanol, 2- [N- (3,5-di-t-butyl-4-hydroxyphenylmethyl) -N-methylamino] ethanol, 2-
[N- (2-methyl-3,5-di-t-butyl-4-hydroxyphenylmethyl) -N-methylamino] ethanol, 2- [N- (3-t-
Butyl-2-hydroxyphenylmethyl) -N-ethylamino] ethanol, 2- [N- (3-t-butyl-4-hydroxyphenylmethyl) -N-ethylamino] ethanol, 2- [N- (3-
t-butyl-2-hydroxy-5-methylphenylmethyl) -N
-Ethylamino] ethanol, 2- [N- (3,5-di-t-butyl)
2-hydroxyphenylmethyl) -N-ethylamino] ethanol, 2- [N- (3-t-butyl-4-hydroxy-5-methylphenylmethyl) -N-ethylamino] ethanol, 2- [N
-(3,5-Di-t-butyl-4-hydroxyphenylmethyl) -N
-Ethylamino] ethanol, 2- [N- (2-methyl-3,5-di-
t-butyl-4-hydroxyphenylmethyl) -N-ethylamino] ethanol, 2- [N- (3-t-butyl-2-hydroxyphenylmethyl) -Nt-butylamino] ethanol,

2- [N- (3-t-butyl-4-hydroxyphenylmethyl) -Nt-butylamino] ethanol, 2- [N- (3-t-
Butyl-2-hydroxy-5-methylphenylmethyl) -Nt
-Butylamino] ethanol, 2- [N- (3,5-di-t-butyl)
-2-hydroxyphenylmethyl) -Nt-butylamino]
Ethanol, 2- [N- (3-t-butyl-4-hydroxy-5-methylphenylmethyl) -Nt-butylamino] ethanol,
2- [N- (3,5-di-t-butyl-4-hydroxyphenylmethyl) -Nt-butylamino] ethanol, 2- [N- (2-methyl
-3,5-di-t-butyl-4-hydroxyphenylmethyl) -N
-t-butylamino] ethanol, 3- [N- (3-t-butyl-2-
Hydroxyphenylmethyl) amino] propanol, 3-
[N- (3-t-butyl-4-hydroxyphenylmethyl) amino] propanol, 3- [N- (3-t-butyl-2-hydroxy-5)
-Methylphenylmethyl) amino] propanol, 3- [N
-(3,5-di-t-butyl-2-hydroxyphenylmethyl) amino] propanol, 3- [N- (3-t-butyl-4-hydroxy)
-5-methylphenylmethyl) amino] propanol, 3-
[N- (3,5-di-t-butyl-4-hydroxyphenylmethyl)
Amino] propanol, 3- [N- (2-methyl-3,5-di-t-butyl-4-hydroxyphenylmethyl) amino] propanol, 3- [N- (3-t-butyl-2-hydroxy- 5-methylphenylmethyl) -N-methylamino] propanol, 3- [N-
(3,5-di-t-butyl-2-hydroxyphenylmethyl) -N-
Methylamino] propanol,

3- [N- (3-t-butyl-4-hydroxy-5-methylphenylmethyl) -N-methylamino] propanol,
3- [N- (3,5-di-t-butyl-4-hydroxyphenylmethyl) -N-methylamino] propanol, 4- [N- (3-t-butyl-2-hydroxyphenylmethyl) amino] Butanol, 4- [N- (3-t-butyl-4-hydroxyphenylmethyl)
Amino] butanol, 4- [N- (3-t-butyl-2-hydroxy
-5-methylphenylmethyl) amino] butanol, 4- [N
-(3,5-di-t-butyl-2-hydroxyphenylmethyl) amino] butanol, 4- [N- (3-t-butyl-4-hydroxy-5)
-Methylphenylmethyl) amino] butanol, 4- [N-
(3,5-di-t-butyl-4-hydroxyphenylmethyl) amino] butanol, 4- [N- (2-methyl-3,5-di-t-butyl)
-4-hydroxyphenylmethyl) amino] butanol,
4- [N- (3-t-butyl-2-hydroxy-5-methylphenylmethyl) -N-methylamino] butanol, 4- [N- (3,5-di-t
-Butyl-2-hydroxyphenylmethyl) -N-methylamino] butanol, 4- [N- (3-t-butyl-4-hydroxy-5)
-Methylphenylmethyl) -N-methylamino] butanol, 4- [N- (3,5-di-t-butyl-4-hydroxyphenylmethyl) -N-methylamino] butanol and the like.
When A is methylene, for example, by reacting the corresponding alkanolamine with the corresponding phenol and formaldehyde, or when A is an alkylene other than methylene, the corresponding alkanolamine is reacted with the corresponding alkanolamine. By reacting with a halide.

When the linking group X is a group represented by the formula (VIII), typical examples of the hydroxy compound (XIII) include, for example, N- (2-hydroxyethyl) -2-hydroxy-3-t-butylbenzoic acid Acid amide, N- (2-hydroxyethyl) -4-hydroxy-3-t-butylbenzoic acid amide, N- (2-hydroxyethyl) -2-hydroxy-3-t-butyl-5-methylbenzoic acid amide , N- (2-hydroxyethyl) -4-hydroxy-3-t-butyl-5-methylbenzoic acid amide, N- (2-hydroxyethyl) -2-hydroxy-3,5-di-t-butylbenzoic acid Acid amide,
N- (2-hydroxyethyl) -4-hydroxy-3,5-di-t-butylbenzoic acid amide, N- (2-hydroxyethyl) -3- (2-
(Hydroxy-3-t-butylphenyl) propionamide,
N- (2-hydroxyethyl) -3- (4-hydroxy-3-t-butylphenyl) propionamide, N- (2-hydroxyethyl) -3- (2-hydroxy-3-t-butyl-5- Methylphenyl) propionamide, N- (2-hydroxyethyl) -3- (4
-Hydroxy-3-t-butyl-5-methylphenyl) propionamide, N- (2-hydroxyethyl) -3- (2-hydroxy-3,5-di-t-butylphenyl) propionamide, N-
(2-hydroxyethyl) -3- (4-hydroxy-3,5-di-t-
Butylphenyl) propionamide, N-methyl-N- (2-hydroxyethyl) -3- (2-hydroxy-3-t-butylphenyl) propionamide,

N-methyl-N- (2-hydroxyethyl) -3- (4-
(Hydroxy-3-t-butylphenyl) propionamide,
N-methyl-N- (2-hydroxyethyl) -3- (2-hydroxy-3
-t-butyl-5-methylphenyl) propionamide, N-
Methyl-N- (2-hydroxyethyl) -3- (4-hydroxy-3-t
-Butyl-5-methylphenyl) propionamide, N-methyl-N- (2-hydroxyethyl) -3- (2-hydroxy-3,5-
Di-t-butylphenyl) propionamide, N-methyl-N-
(2-hydroxyethyl) -3- (4-hydroxy-3,5-di-t-butylphenyl) propionamide, N-ethyl-N- (2-hydroxyethyl) -3- (2-hydroxy-3- (t-butylphenyl) propionamide, N-ethyl-N- (2-hydroxyethyl) -3- (4-hydroxy-3-t-butylphenyl) propionamide, N-ethyl-N- (2-hydroxyethyl) -3- (2-hydroxy-3-t-butyl-5-methylphenyl) propionamide, N-ethyl-N- (2-hydroxyethyl) -3- (4-hydroxy-3-t-butyl-5- Methylphenyl) propionamide, N-ethyl-N- (2-hydroxyethyl) -3- (2-hydroxy-3,5-di-t-butylphenyl) propionamide,
N-ethyl-N- (2-hydroxyethyl) -3- (4-hydroxy-
3,5-di-t-butylphenyl) propionamide,

Nt-butyl-N- (2-hydroxyethyl) -3- (2
-Hydroxy-3-t-butylphenyl) propionamide, Nt-butyl-N- (2-hydroxyethyl) -3- (4-hydroxy-3-t-butylphenyl) propionamide, Nt-butyl-N- ( 2-hydroxyethyl) -3- (2-hydroxy-3-t-
Butyl-5-methylphenyl) propionamide, Nt-butyl-N- (2-hydroxyethyl) -3- (4-hydroxy-3-t-
Butyl-5-methylphenyl) propionamide, Nt-butyl-N- (2-hydroxyethyl) -3- (2-hydroxy-3,5-
Di-t-butylphenyl) propionamide, Nt-butyl
-N- (2-hydroxyethyl) -3- (4-hydroxy-3,5-di-t
-Butylphenyl) propionamide, N- (3-hydroxypropyl) -3- (2-hydroxy-3-t-butylphenyl)
Propionamide, N- (3-hydroxypropyl) -3- (4-
(Hydroxy-3-t-butylphenyl) propionamide,
N- (3-hydroxypropyl) -3- (2-hydroxy-3-t-butyl-5-methylphenyl) propionamide, N- (3-hydroxypropyl) -3- (4-hydroxy-3-t- Butyl-5-
Methylphenyl) propionamide, N- (3-hydroxypropyl) -3- (2-hydroxy-3,5-di-t-butylphenyl) propionamide, N- (3-hydroxypropyl) -3-
(4-hydroxy-3,5-di-t-butylphenyl) propionamide,

N- (4-hydroxybutyl) -3- (2-hydroxy-3-t-butylphenyl) propionamide, N- (4-hydroxybutyl) -3- (4-hydroxy-3-t-butyl Phenyl) propionamide, N- (4-hydroxybutyl) -3- (2
-Hydroxy-3-t-butyl-5-methylphenyl) propionamide, N- (4-hydroxybutyl) -3- (4-hydroxy-3-t-butyl-5-methylphenyl) propionamide, N- ( 4-hydroxybutyl) -3- (2-hydroxy-3,5-
Di-t-butylphenyl) propionamide, N- (4-hydroxybutyl) -3- (4-hydroxy-3,5-di-t-butylphenyl) propionamide, N- (6-hydroxyhexyl) -3 -(2-hydroxy-3-t-butylphenyl) propionamide, N- (6-hydroxyhexyl) -3- (4-hydroxy-3-t-butylphenyl) propionamide, N- (6-hydroxyhexyl) -3- (2-hydroxy-3-t-butyl-5-
Methylphenyl) propionamide, N- (6-hydroxyhexyl) -3- (4-hydroxy-3-t-butyl-5-methylphenyl) propionamide, N- (6-hydroxyhexyl) -3- (2- (Hydroxy-3,5-di-t-butylphenyl) propionamide, N- (6-hydroxyhexyl) -3- (4-hydroxy-3,5-di-t-butylphenyl) propionamide,

N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -2-hydroxy-3-t-butylbenzoic acid amide, N- [1- (hydroxymethyl) -1-methyl- 2-hydroxyethyl] -4-hydroxy-3-t-butylbenzoic acid amide,
N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -2-hydroxy-3-t-butyl-5-methylbenzoic acid amide, N- [1- (hydroxymethyl) -1-methyl 2-hydroxyethyl] -4-hydroxy-3-t-butyl-5-methylbenzoic acid amide, N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -2-hydroxy-3, 5-di-t-butylbenzoic acid amide, N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -4-hydroxy-3,5-di-t-butylbenzoic acid amide, N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (2-hydroxy-3-t-butylphenyl)
Propionamide, N- [1- (hydroxymethyl) -1-methyl
-2-hydroxyethyl] -3- (4-hydroxy-3-t-butylphenyl) propionamide, N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (2-hydroxy
-3-t-butyl-5-methylphenyl) propionamide,
N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (4-hydroxy-3-t-butyl-5-methylphenyl) propionamide,

N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (2-hydroxy-3,5-di-t-butylphenyl) propionamide, N- [1- ( Hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (4-hydroxy
-3,5-di-t-butylphenyl) propionamide, N-methyl-N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (2-hydroxy-3-t- Butylphenyl) propionamide, N-methyl-N- [1- (hydroxymethyl)-
1-methyl-2-hydroxyethyl] -3- (4-hydroxy-3-t
-Butylphenyl) propionamide, N-methyl-N- [1-
(Hydroxymethyl) -1-methyl-2-hydroxyethyl]-
3- (2-hydroxy-3-t-butyl-5-methylphenyl) propionamide, N-methyl-N- [1- (hydroxymethyl)-
1-methyl-2-hydroxyethyl] -3- (4-hydroxy-3-t-
Butyl-5-methylphenyl) propionamide, N-methyl-N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (2-hydroxy-3,5-di-t-butyl Phenyl) propionamide, N-methyl-N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (4-hydroxy-3,5-di-t-butylphenyl) propionamide,

N-ethyl-N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (2-hydroxy-3-t-butylphenyl) propionamide, N-ethyl-N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (4
-Hydroxy-3-t-butylphenyl) propionamide, N-ethyl-N- [1- (hydroxymethyl) -1-methyl-2-
Hydroxyethyl] -3- (2-hydroxy-3-t-butyl-5-
Methylphenyl) propionamide, N-ethyl-N- [1- (
Hydroxymethyl) -1-methyl-2-hydroxyethyl] -3-
(4-hydroxy-3-t-butyl-5-methylphenyl) propionamide, N-ethyl-N- [1- (hydroxymethyl) -1-
Methyl-2-hydroxyethyl] -3- (2-hydroxy-3,5-
Di-t-butylphenyl) propionamide, N-ethyl-N
-[1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (4-hydroxy-3,5-di-t-butylphenyl) propionamide, Nt-butyl-N- [1- ( Hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (2-hydroxy
-3-t-butylphenyl) propionamide, Nt-butyl
-N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (4-hydroxy-3-t-butylphenyl) propionamide, Nt-butyl-N- [1- (hydroxymethyl ) -1-
Methyl-2-hydroxyethyl] -3- (2-hydroxy-3-t-
Butyl-5-methylphenyl) propionamide,

Nt-butyl-N- [1- (hydroxymethyl) -1-
Methyl-2-hydroxyethyl] -3- (4-hydroxy-3-t-
Butyl-5-methylphenyl) propionamide, Nt-butyl-N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (2-hydroxy-3,5-di-t-butyl Phenyl) propionamide, Nt-butyl-N- [1- (hydroxymethyl) -1-methyl-2-hydroxyethyl] -3- (4-hydroxy-3,5-di-t-butylphenyl) propionamide,
N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -2-hydroxy-3-t-butylbenzoic acid amide, N- [1-
(Hydroxymethyl) -1-ethyl-2-hydroxyethyl] -4
-Hydroxy-3-t-butylbenzoic acid amide, N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -2-hydroxy-3-t-butyl-5-methylbenzoic acid amide, N -[1-
(Hydroxymethyl) -1-ethyl-2-hydroxyethyl] -4
-Hydroxy-3-t-butyl-5-methylbenzoic acid amide, N
-[1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -2-hydroxy-3,5-di-t-butylbenzoic acid amide,
N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -4-hydroxy-3,5-di-t-butylbenzoic acid amide;

N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (2-hydroxy-3-t-butylphenyl) propionamide, N- [1- (hydroxymethyl)- 1-ethyl-2-hydroxyethyl] -3- (4-hydroxy-3-t-butylphenyl) propionamide, N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- ( 2-hydroxy-3-t-butyl-5-methylphenyl) propionamide, N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (4-hydroxy-3-t-butyl -5-methylphenyl) propionamide, N- [1- (hydroxymethyl) -1-
Ethyl-2-hydroxyethyl] -3- (2-hydroxy-3,5-
Di-t-butylphenyl) propionamide, N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (4-
(Hydroxy-3,5-di-t-butylphenyl) propionamide, N-methyl-N- [1- (hydroxymethyl) -1-ethyl-2
-Hydroxyethyl] -3- (2-hydroxy-3-t-butylphenyl) propionamide, N-methyl-N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (4 -Hydroxy-3-t-butylphenyl) propionamide, N-methyl-N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (2-hydroxy-3-t-butyl- 5-methylphenyl) propionamide,

N-methyl-N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (4-hydroxy-3-t-butyl-5-methylphenyl) propionamide, N- Methyl
-N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (2-hydroxy-3,5-di-t-butylphenyl)
Propionamide, N-methyl-N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (4-hydroxy
-3,5-di-t-butylphenyl) propionamide, N-ethyl-N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (2-hydroxy-3-t- Butylphenyl) propionamide, N-ethyl-N- [1- (hydroxymethyl)-
1-ethyl-2-hydroxyethyl] -3- (4-hydroxy-3-t
-Butylphenyl) propionamide, N-ethyl-N- [1-
(Hydroxymethyl) -1-ethyl-2-hydroxyethyl]-
3- (2-hydroxy-3-t-butyl-5-methylphenyl) propionamide, N-ethyl-N- [1- (hydroxymethyl)-
1-ethyl-2-hydroxyethyl] -3- (4-hydroxy-3-t
-Butyl-5-methylphenyl) propionamide, N-ethyl-N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (2-hydroxy-3,5-di-t- Butylphenyl) propionamide, N-ethyl-N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (4-hydroxy-3,5-di-t-butylphenyl) propionamide ,

Nt-butyl-N- [1- (hydroxymethyl) -1-
Ethyl-2-hydroxyethyl] -3- (2-hydroxy-3-t-
Butylphenyl) propionamide, Nt-butyl-N- [1-
(Hydroxymethyl) -1-ethyl-2-hydroxyethyl]-
3- (4-hydroxy-3-tbutylphenyl) propionamide, Nt-butyl-N- [1- (hydroxymethyl) -1-ethyl
-2-hydroxyethyl] -3- (2-hydroxy-3-t-butyl
-5-methylphenyl) propionamide, Nt-butyl-N
-[1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (4-hydroxy-3-t-butyl-5-methylphenyl) propionamide, Nt-butyl-N- [1- ( Hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (2-hydroxy-3,5-di-t-butylphenyl) propionamide,
Nt-butyl-N- [1- (hydroxymethyl) -1-ethyl-2-hydroxyethyl] -3- (4-hydroxy-3,5-di-t-butylphenyl) propionamide. These are described, for example, in Soviet patent 1203083 and French patent 257724.
It can be produced by reacting a corresponding amino alcohol with a corresponding carboxylic acid, carboxylic acid ester, or carboxylic acid halide according to a known method such as No. 2.

Thus, the phosphites (I) of the present invention can be obtained. Degradability can be improved. Representative examples of such amines include, for example, trialkanolamines such as triethanolamine, tripropanolamine, and tri-i-propanolamine, diethanolamine, dipropanolamine, di-i-propanolamine, tetraethanolethylenediamine, and tetra-ethanolamine. i-
Dialkanolamines such as propanolethylenediamine, monoalkanolamines such as dibutylethanolamine and dibutyl-i-propanolamine, aromatic amines such as 1,3,5-trimethyl-2,4,6-triazine, dibutylamine , Piperidine, alkylamines such as 2,2,6,6-tetramethylpiperidine, 4-hydroxy-2,2,6,6-tetramethylpiperidine, hexamethylenetetramine, triethylenediamine, triethylenetetramine, tetraethylenepentamine Polyalkylene polyamines such as min,
The following hindered amine light stabilizers are mentioned.
Further, long-chain aliphatic amines described in JP-A-61-63686, compounds containing a sterically hindered amine group described in JP-A-6-329830, hindered amines described in JP-A-7-90270 are disclosed. Peridinyl-based light stabilizers, organic amines described in JP-A-7-278164, and the like can also be used. The use ratio of amines to phosphites (I) is usually 0.01 to 25% by weight.
It is about.

Representative examples of the acid-bonded metal salt include hydrotalcites. Examples of hydrotalcites include a double salt compound represented by the following formula. M ²⁺ _1-x・ M ³⁺ _x・ (OH ⁻ ) ₂・ (A ⁿ⁻ ) _{x / n}・ pH ₂ O (where M ²⁺ is Mg, Ca, Sr, Ba, Zn, Pb , Sn and / or
Or Ni, M ³⁺ represents Al, B or Bi, n
Is a numerical value from 1 to 4, x is a numerical value from 0 to 0.5, and p is a numerical value from 0 to
2 represents a numerical value. A ^n- represents an anion having a valence of n. Here, specific examples of the anion having a valence of ^{n represented} by A ⁿ⁻ include, for example, OH ⁻ , Cl ⁻ , Br ⁻ , I ⁻ , ClO ₄ ⁻ , HC
_{^{O 3 -, C 6 H 5}} COO -, CO 3 2-, SO 2-, - OOCCOO -, (CHO
_{^{HCO0) 2 2-, C 2 H}} 4 (COO) 2 2-, (CH 2 COO) 2 2-, CH 3 CHOHCO
_{^{O -, SiO 3 2-, SiO}} 4 4-, Fe (CN) 6 4-, BO 3-, PO 3 3-, HPO
Among _{the 4} ^2- or the like is represented by the general formula mentioned, those particularly preferred include, for example, hydrotalcites represented by the following formula. Mg _1-x Al _x (OH) ₂ (CO ₃ ) _{x / 2} · pH ₂ O (where x and p represent the same meaning as described above) Even if the hydrotalcites are natural products, It may be a synthetic product, and it can be used irrespective of its crystal structure, crystal particle diameter and the like. Further, ultrafine zinc oxide described in JP-A-6-329830 and inorganic compounds described in JP-A-7-278164 can also be used. The ratio of the acid-bonded metal salt to the phosphite (I) is usually about 0.01 to 25% by weight.

The phosphites (I) of the present invention are effective for stabilizing organic materials against thermal degradation and oxidative degradation. Examples of the organic materials that can be stabilized by the present invention include the following, each of which can stabilize a single material or a mixture of two or more, but is limited to these organic materials. It is not something to be done.

(1) Polyethylene, for example, high density polyethylene (HD-PE), low density polyethylene (LD-P)
E), linear low density polyethylene (LLDPE), (2)
Polypropylene, (3) methylpentene polymer, (4) E
EA (ethylene / ethyl acrylate copolymer) resin, (5)
Ethylene / vinyl acetate copolymer resin, (6) polystyrenes, for example, 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,

(11) chlorinated polyethylene, polychloroprene, chlorinated rubber, (12) polyvinyl chloride, polyvinylidene chloride, (13) methacrylic resin, (14) ethylene / vinyl alcohol copolymer resin, (15) fluororesin , (16) polyacetal, (17) grafted polyphenylene ether resin and polyphenylene sulfide resin, (18) polyurethane, (19) polyamide, (20) polyester resin, such as polyethylene terephthalate, polybutylene terephthalate,

(21) Polycarbonate, (22) Polyacrylate, (23) Polysulfone, polyetheretherketone, polyethersulfone, (24) Thermoplastic resin such as aromatic polyester resin, (25) Epoxy resin, (26) Diallyl phthalate prepolymer, (27) silicone resin, (28) unsaturated polyester resin, (29) acryl-modified benzoguanamine resin, (30) benzoguanamine / melamine resin, (31) thermosetting resin such as urea resin,

(32) polybutadiene, (33) 1,2-polybutadiene, (34) polyisoprene, (35) styrene / butadiene copolymer, (36) butadiene / acrylonitrile copolymer, (37) ethylene / propylene copolymer Polymer, (3
8) Silicone rubber, (39) Epichlorohydrin rubber, (4
0) acrylic rubber, (41) natural rubber,

(42) Chlorine rubber paint, (43) Polyester resin paint, (44) Urethane resin paint, (45) Epoxy resin paint, (46) Acrylic resin paint, (47) Vinyl resin paint,
(48) amino alkyd resin paint, (49) alkyd resin paint, (50) nitrocellulose resin paint, (51) oil paint,
(52) Wax, (53) Lubricating oil, etc.

Among them, thermoplastic resins, especially polyethylene, for example, polyolefins such as HD-PE, LD-PE, LLDPE and polypropylene, and engineering resins such as polyamide, polyethylene terephthalate, polybutylene terephthalate and polycarbonate are preferably used. These polyolefins are not particularly limited, and may be, for example, those obtained by radical polymerization or those produced by polymerization using a catalyst containing a metal belonging to Group IVb, Vb, VIb or VIII of the periodic table. The metal-containing catalyst may be a metal complex having one or more ligands, for example, oxides, halogen compounds, alcoholates, esters, aryls, etc., which are coordinated by π or σ bonds. Magnesium chloride, titanium chloride,
It may be supported on a substrate such as alumina or silicon oxide. As the polyolefin, those produced using, for example, a Ziegler-Natta catalyst, a TNZ catalyst, a metallocene catalyst, a Phillips catalyst or the like are preferably used. The engineering resin is not particularly limited. For example, a polyamide resin having an amide bond in a polymer chain and capable of being heated and melted may be used. For example, those produced by any method such as condensation reaction of diamines and dicarboxylic acids, condensation reaction of aminocarboxylic acids, ring-opening polymerization of lactams, and the like, typical examples of which are nylon 66, nylon 69, nylon 610,
Nylon 612, poly-bis- (p-aminocyclohexyl) methandodecamide, nylon 46, nylon 6,
Nylon 12, nylon 66/6, which is a copolymer of nylon 66 and nylon 6, and copolymers such as nylon 6/12. As the polyester resin, any resin having an ester bond in the polymer chain and capable of being heated and melted may be used, and examples thereof include polyesters obtained by polycondensation of dicarboxylic acids and dihydroxy compounds, and the like. Homopolyesters, copolyesters Any of these may be used. Further, as the polycarbonate resin, any resin having a carbonate bond in the polymer chain and any material that can be heated and melted may be used.
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 an acid acceptor and a molecular weight modifier is exemplified. The polycarbonate resin may be linear or branched, and may be a copolymer.

When the phosphites (I) of the present invention are added to stabilize an organic material, the phosphites (I) are usually added in an amount of 0.0
About 1 to 5 parts by weight, preferably about 0.03 to 3 parts by weight, more preferably about 0.05 to 1 part by weight. If the amount used is less than 0.01 part by weight, the stabilizing effect is not always sufficient, and if it exceeds 5 parts by weight, the effect corresponding to the improvement cannot be obtained, which is economically disadvantageous.

In incorporating the phosphites (I) of the present invention into an organic material, if necessary, other additives such as a phenolic antioxidant, a sulfuric antioxidant, and a phosphorus-based antioxidant may be used. Agent, ultraviolet absorber, light stabilizer, peroxide scavenger, polyamide stabilizer, hydroxylamine, lubricant, plasticizer, flame retardant, nucleating agent, metal deactivator, antistatic agent, pigment, filler, pigment , Antiblocking agents, surfactants, processing aids, foaming agents, emulsifiers, brighteners, calcium stearate, neutralizing agents such as hydrotalcite, and even 9,10-dihydro-9-oxa-10-
Coloring improvers such as phosphophenanthrene-10-oxide,
U.S. Pat.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,
Co-stabilizers such as benzofurans and indolines described in JP-A-591,102 and the like can also be contained. Of course, these additives can be blended simultaneously with the phosphites (I), or can be blended at a different stage from the phosphites (I).

Here, examples of the phenolic antioxidant include the following. (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.

(2) Examples of alkylthiomethylphenol 2,4-dioctylthiomethyl-6-t-butylphenol, 2,2
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) adipates and mixtures thereof.

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

(6) Examples of alkylidene bisphenols and derivatives thereof 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 [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.

(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-dimethylbenzylmercaptoacetate, 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-hydroxy Benzyl mercapto acetate 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.

(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-dimethyl Benzyl) isocyanurate,
Tris (3,5-di-t-butyl-4-hydroxybenzyl) isocyanurate, 2,4,6-tris (3,5-di-t-butyl-4-hydroxy-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.

(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-
Calcium salts of butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-t-butyl-4-hydroxy-3-methylbenzylphosphonate, 3,5-di-t-butyl-4-hydroxybenzylphosphonic acid monoester and their salts Mixtures and the like. (12) Examples of acylaminophenol derivatives: 4-hydroxylauric anilide, 4-hydroxystearic anilide, octyl-N- (3,5-di-t-butyl-4-hydroxyphenyl) carbanate and mixtures thereof. (13) β- (3,5-di-t-butyl-4-hydroxyphenyl)
Examples of esters of propionic acid with the following monohydric or polyhydric alcohols: methanol, ethanol, octanol, octadecanol, ethylene glycol, 1,3-propanediol, 1,3
4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiro glycol, 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.

(14) β- (5-t-butyl-4-hydroxy-3-
Examples of esters of methylphenyl) propionic acid with the following monohydric or polyhydric alcohols: methanol, ethanol, octanol, octadecanol, ethylene glycol, 1,3-propanediol,
4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiro glycol, 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, spiro glycol, 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.

(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, 3-propanediol, 1,
4-butanediol, 1,6-hexanediol, 1,9-nonanediol, neopentyl glycol, diethylene glycol, thioethylene glycol, spiro glycol, 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) β- (3,5-di-t-butyl-4-hydroxyphenyl)
Examples of amides of 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.

Examples of the 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) and the like. Further, examples of the phosphorus-based antioxidant include the following. 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-triphenyl
-t-butylphenyl) pentaerythritol diphosphite, tristearylsorbitol triphosphite, 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, bis
(2,4-di-t-butyl-6-methylphenyl) methyl phosphite, 2- (2,4,6-tri-t-butylphenyl) -5-ethyl-5-butyl-1,3,2 -Oxaphospholinane, 2,2 ', 2''
-Nitrilo [triethyl-tris (3,3 ', 5,5'-tetra-t
-Butyl-1,1'-biphenyl-2,2'-diyl) phosphites and mixtures thereof.

Examples of the ultraviolet absorber include the following. (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, hesisadecyl
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.

(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, 2- [2'-hydroxy-3 ', 5'-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-2'-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-octyloxy Carbonylethyl) 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-benzotriazole
2-yl) phenol], poly (3-11) (ethylene glycol) and 2- [3'-t-butyl-2'-hydroxy-5 '-(2-methoxycarbonylethyl) phenyl] benzotriazole Condensate, 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-2
H-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.

Examples of the light stabilizer include the following. (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 decandioate,
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, tetrakis (1,2,2,6,6
-Pentamethyl-4-piperidyl) 1,2,3,4-butanetetracarboxylate, 1,2,3,4-butanetetracarboxylic acid and 1,2,2,6,6-pentamethyl-4-piperidinol and 1 -
Mixed esterified product with tridecanol,

Mixed esterified product of 1,2,3,4-butanetetrabonic acid with 2,2,6,6-tetramethyl-4-piperidinol and 1-tridecanol, 1,2,3,4-butanetetra Carboxylic acid and 1,2,2,6,6-pentamethyl-4-piperidinol and
3, 9-bis (2-hydroxy-1,1-dimethylethyl) -2,4,
Mixed esterified product with 8,10-tetraoxaspiro [5.5] undecane, 1,2,3,4-butanetetracarboxylic acid and 2,2,6,
6-tetramethyl-4-piperidinol and 3,9-bis (2-
Mixed esterified product with hydroxy-1,1-dimethylethyl) -2,4,8,10-tetraoxaspiro [5.5] undecane, dimethyl succinate and 1- (2-hydroxyethyl) -4-hydroxy-2 Polycondensation product with 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)],
Polycondensate of N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine with 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-triazine-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-triazine-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.

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

(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.

Examples of the metal deactivator include the following. N, N'-diphenyloxamide, N-salicyral-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 bisphenyl hydrazide, N, N'-bis (salicyloyl) oxalyl dihydrazide, N, N'-bis (salicyloyl) thiopropionyl dihydrazide and mixtures thereof.

Examples of peroxide scavengers include esters of β-thiodipropionic acid, mercaptobenzimidazole, zinc salts of 2-mercaptobenzimidazole, zinc salts of dibutyldithiocarbamic acid, dioctadecyl disulfide, and pentaerythritol tetrakis (β -Dodecylmercapto) propionate and mixtures thereof. Examples of the polyamide stabilizer include copper or divalent manganese salts of iodides or phosphorus compounds, and mixtures thereof. Examples of the hydroxyamine include, for example, N, N-dibenzylhydroxyamine, N, N-diethylhydroxyamine, N, N-
Dioctylhydroxyamine, N, N-dilaurylhydroxyamine, N, N-ditetradecylhydroxyamine, N, N-
Examples include dihexadecylhydroxyamine, N, N-dioctadecylhydroxyamine, N-hexadecyl-N-octadecylhydroxyamine, N-heptadecyl-N-octadecylhydroxyamine, and mixtures thereof. 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. Can be Examples of the lubricant include aliphatic hydrocarbons such as paraffin and wax, higher aliphatic acids having 8 to 22 carbon atoms, and higher aliphatic acid metals having 8 to 22 carbon atoms (Al, Ca, M
g, Zn) salt, aliphatic alcohol having 8 to 22 carbon atoms, polyglycol, higher fatty acid having 4 to 22 carbon atoms and 4 to 18 carbon atoms
Esters with aliphatic monohydric alcohols, higher aliphatic amides having 8 to 22 carbon atoms, silicone oils, rosin derivatives and the like.

Examples of the nucleating agent include the following. Sodium 2,2'-methylenebis
(4,6-di-t-butylphenyl) phosphate, [phosphoric acid
-2,2'-Methylenebis (4,6-di-t-butylphenyl)]
Dihydroxyaluminum, bis [2,2'-methylenebis (4,6-di-t-butylphenyl) phosphate] hydroxyaluminum, tris [-2,2'-methylenebisphosphate
(4,6-di-t-butylphenyl)] aluminum, metal salts of benzoic acid such as sodium bis (4-t-butylphenyl) phosphate and sodium benzoate, aluminum p-t-butylbenzoate, 1,3: 2,4-bis (O-benzylidene) sorbitol, 1,3: 2,4-bis (O-methylbenzylidene) sorbitol, 1,3: 2,4-bis (O-ethylbenzylidene) sorbitol, 1,3- O-3,4-dimethylbenzylidene-
2,4-O-benzylidene sorbitol, 1,3-O-benzylidene-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-dimethylbenzylidenesorbitol, 1,3-O-3, 4-dimethylbenzylidene-2,4-Op-chlorobenzylidene sorbitol, 1,
3: 2,4-bis (Op-chlorobenzylidene) sorbitol and mixtures thereof. Examples of the filler include calcium carbonate, silicate, glass fiber, asbestos, talc, kaolin, mica, barium sulfate, carbon black, carbon fiber, zeolite, and mixtures thereof.

Among these additives, those preferably used are phenolic antioxidants, phosphorus antioxidants,
UV absorbers, hindered amine light stabilizers, peroxide scavengers and neutralizers. Particularly preferred phenolic antioxidants include the following compounds, which may be used in combination of two or more. 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,

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,
Tris (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, 3,5-di-t-butyl- Calcium salt of 4-hydroxybenzylphosphonic acid monoester, n-octadecyl 3- (3,5-di-t-butyl
-4-hydroxyphenyl) propionate, neopentanetetrayltetrakis (3,5-di-t-butyl-4-hydroxycinnamate), thiodiethylenebis (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 Screw
(3,5-di-t-butyl-4-hydroxycinnamate), hexamethylenebis (3,5-di-t-butyl-4-hydroxycinnamate), triethylene glycol bis (5-t-tyl- 4-hydroxy-3-methylcinnamate), 3,9-bis
[2- (3- (3-t-butyl-4-hydroxy-5-methylphenyl) propionyloxy) -1,1-dimethylethyl] -2,4,8,
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 and the like.

Further, particularly preferred phosphorus-based antioxidants include the following, and two or more of these can be used. 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'-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 and the like.

Particularly preferred ultraviolet absorbers include:
The following are mentioned, and these can be used in combination of two or more.
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) benzotriazole, 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole, 2- (3-t-butyl-2-hydroxy -Five-
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.

Further, particularly preferred light stabilizers include the following, and two or more of these can be used. Screw
(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,

Tetrakis (1,2,6,6-pentamethyl-4-piperidyl) 1,2,3,4-butanetetracarboxylate,
Mixed esterified product of 1,2,3,4-butanetetracarboxylic acid and 1,2,2,6,6-pentamethyl-4-piperidinol and 1-tridecanol, 1,2,3,4-butanetetracarboxylic acid And two,
Mixed esterified product of 2,6,6-tetramethyl-4-piperidinol and 1-tridecanol, 1,2,3,4-butanetetracarboxylic acid and 1,2,2,6,6-pentamethyl-4-piperidinol And a mixed esterified product with 3,9-bis (2-hydroxy-1,1-dimethylethyl) -2,4,8,10-tetraoxaspiro [5.5] undecane, 1,2,3,4- Butanetetracarboxylic acid and 2,2,6,6-tetramethyl-4-piperidinol and 3,9-
Bis (2-hydroxy-1,1-dimethylethyl) -2,4,8,10-
Mixed esterified product with tetraoxaspiro [5.5] undecane, polycondensate 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) -1,3,5-triazine-2,4-diyl) ((2,2,
6,6-tetramethyl-4-piperidyl) imino) hexamethylene ((2,2,6,6-tetramethyl-4-piperidyl) imino)] and the like.

In blending the phosphites (I) or other additives used as necessary with the organic material, any known method and apparatus for obtaining a homogeneous mixture may be used. it can. For example, when the organic material is a solid polymer, the phosphites (I) or other additives can be directly dry-blended with the solid polymer, or the phosphite compound or another Additives can also be incorporated into the solid polymer in the form of a masterbatch. If the organic material is a liquid polymer,
The phosphites (I) or other additives may be added to the polymer solution during or immediately after the polymerization in the form of a solution or dispersion. On the other hand, when the organic material is a liquid such as oil, phosphites (I) or other additives can be directly added and dissolved, or phosphites (I) or Further, other additives may be added in a state of being dissolved or suspended in a liquid medium.

[0125]

The phosphites (I) of the present invention are:
Despite being a cyclic phosphite derived from a diol, it has excellent performance as a stabilizer for various organic materials such as thermoplastic resins such as polyolefins. It is stable against thermal degradation and oxidative degradation during use, and becomes a high quality product.

[0126]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the invention is limited thereto.

Example 1 2- [2- [5,5'-dimethyl- [1,3,2]
Dioxaphospholinan-2-yl] oxy-3-t-butyl-5
-Methylbenzyl] -6-t-butyl-4-methylphenol (Compound 1) (1) Preparation of intermediate halogenophosphite Tetrahydrofuran was placed in a flask equipped with a thermometer, a stirrer and a condenser under a nitrogen stream. (THF) 150ml, phosphorus trichloride
34.3g, cooled to 0-5 ° C, then a mixture of 150ml THF and 24.5g neopentyl glycol, pyridine
After adding 37.9 g, the mixture was stirred at room temperature for 12 hours. After filtering off the generated pyridine hydrochloride, the filtrate was concentrated and distilled under reduced pressure to obtain 24.8 g of an intermediate halogenophosphite. Boiling point 68-70 ° C (12mmHg)

(2) 2- [2- [5,5'-dimethyl- [1,3,2] dioxaphospholinan-2-yl] oxy-3-t-butyl-5-methylbenzyl] -6 Production of -t-butyl-4-methylphenol 8 g of the above intermediate and 50 ml of toluene were placed in a flask equipped with a thermometer, a stirrer and a condenser, and 100 ml of toluene and 2,2′-methylenebis (6- (t-butyl-4-methylphenol) 16.2 g mixture, triethylamine
After adding 5.3 g, the mixture was stirred at 80 ° C. for 5 hours. After cooling to room temperature, the generated triethylamine hydrochloride was separated by filtration, the filtrate was concentrated, and the residue was washed with toluene to obtain 23.1 g of white crystals. Mass spectrometry (FD-MS): m / z 472 Melting point: 113 ° C

¹ H-NMR (CDCl ₃ ) 0.79 (s.3H), 1.30 (s, 3H), 1.37 (s, 18H), 1.43 (s, 18H), 2.20
(s, 3H), 2.25 (s, 3H), 3.50 (t, 2H), 4.01 (s, 2H), 4.33 (dd, 2
H), 5.28 (s, 1H), 6.73 (d, 1H), 6.76 (d, 1H), 6.98 (d, 1H), 7.0
7 (d, 1H) ³¹ P-NMR (CDCl ₃ ) 119.8 ppm

Example 2: 2- [2- [5,5'-dimethyl- [1,3,2]
Preparation of dioxaphospholinan-2-yl] oxy-3,5-di-t-butylphenyl] -4,6-di-t-butylphenol (compound 2) In Example 1- (2), the intermediate halogeno Phosphite 7.
A mixture consisting of 9 g and 100 ml of toluene, toluene and 2,2'-
Methylene bis (6-t-butyl-4-methylphenol) 16.2
g, replace 100 ml of toluene with 3,3 ',
A mixture consisting of 19 g of 5,5'-tetra-t-butylbisenyl-2,2'-diol and 6.1 g of triethylamine was used,
The procedure was carried out in accordance with Example 1- (2) except for stirring for 1 hour. After cooling to room temperature, the generated triethylamine hydrochloride was separated by filtration, the filtrate was concentrated, and the residue was crystallized from ethyl acetate-hexane to obtain 7.1 g of white crystals. Mass spectrum (FD-MS): m / z 542 Melting point: 72.0 ° C

¹ H-NMR (CDCl ₃ ) 0.69 (s.3H), 1.11 (s, 3H), 1.31 (s, 9H), 1.32 (s, 9H), 1.43
(s, 9H), 1.49 (s, 9H), 3.01 to 3.21 (m, 2H), 3.94 to 4.04 (m,
2H), 5.03 (s, 1H), 7.07 (d, 1H), 7.13 (d, 1H), 7.33 (d, 1H),
7.46 (d, 1H) ³¹ P-NMR (CDCl ₃ ) 116.5 ppm

Example 3 Thermal Stabilization Test of Polypropylene [Compound] Polypropylene (block) 100 parts by weight Calcium stearate 0.05 part by weight Test compound 0.05 part by weight 1: Compound 2 (prepared in Example 2) P-1: 2- [2- (4,8-di-t-butyl-2,10-dimethyl-12H)
-Dibenzo [d, g] [1,3,2] dioxaphosphosine-3-t-butyl-5-methylbenzyl] -6-t-butyl-4-methylphenol

Using a 30 mmφ single screw extruder, the above composition was melt-kneaded at 250 ° C. and pelletized. The obtained pellets were melted at 250 ° C. under a load of 2160 using a melt indexer.
g, and MFR (g / min) were measured at a residence time of 5 minutes, and the results are shown in Table 1. The smaller the MFR, the better the processing stability.

[0134]

[Table 1] Example Comparative Example 1 1 2 1 2 Test compound Chemical 1 Chemical 2-P-1 Processing stability 19.1 19.0 29.4 19.2

Example 4: Thermal stabilization test of linear low-density polyethylene [Compound] Unstabilized linear low-density polyethylene 100 parts by weight Hydrotalcite 0.1 part by weight Test compound 0.05 part by weight Chemical-1: Compound 1 (Manufactured in Example 1) Compound-2: Compound 2 (Manufactured in Example 2) P-1: 2- [2- (4,8-di-t-butyl-2,10-dimethyl-12H)
-Dibenzo [d, g] [1,3,2] dioxaphosphosine-3-t-butyl-5-methylbenzyl] -6-t-butyl-4-methylphenol

Using a 30 mmφ single screw extruder, the above compound was melt-kneaded at 250 ° C. and pelletized. Using a melt indexer, the obtained pellets were heated at 250 ° C and a load of 5k.
g, MFR (g / min) was measured at a residence time of 5 minutes, and the results are shown in Table 2. The higher the MFR, the better the processing stability.

[0137]

[Table 2] Examples Comparative Examples 1 2 1 2 Test compounds Chemical compound 1 Chemical compound 2-P-1 Processing stability 12.7 12.8 8.6 12.5

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C09K 15/32 C09K 15/32 D

Claims (15)

[Claims] 1. The compound of the general formula (I) (In the formula, R ¹ , R ² , R ³ and R ₄ are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a group having 7 to 7 carbon atoms.
Represents 12 aralkyl groups. X represents a linking group, and ^RA represents a phenyl group which may have a substituent. Phosphites represented by). 2. The phosphite according to claim 1, wherein the linking group X is a divalent group having 1 to 20 carbon atoms, which may have a mere bond or a hetero atom. 3. The linking group X is represented by the following formula (II), (III), (IV),
The phosphite according to claim 1, wherein the phosphite is represented by (V), (VI), (VII) or (VIII). * -A- (II) * -BOA- (III) * -C (O) -A- (IV) * -BOC (O) -A- (V) * -D- C (O) -O-A- ( VI) * -G-N (R 6) -A- (VII) * -G-N (R 6) -C (O) -A- (VIII) ( wherein , * Represents a bond to an oxygen atom, A represents a mere bond or an alkylene group having 1 to 8 carbon atoms,
Represents a dihydric alcohol residue. D represents an alkylene group having 1 to 8 carbon atoms, G represents an alkylene group having 2 to 8 carbon atoms, R ⁶ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a compound represented by the formula (IX) (Wherein R ¹ , R ² , R ³ , R ⁴ and G have the same meaning as described above). ) 4. The method according to claim 1, wherein R ^A is a phenyl group which may have a substituent having 6 to 30 carbon atoms in total.
The phosphites according to any one of claims 1 to 3. 5. The phosphite according to claim 1, wherein R ^A is a group represented by the following formula (X) or (XI). (Wherein, R ⁷ and R ⁸ are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, 12 represents an aralkyl group or a phenyl group, Y and Z
Each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a phenyl group, a hydroxyl group; Represents an alkoxy group having 1 to 8 carbon atoms or an aralkyloxy group having 7 to 12 carbon atoms. ) (Wherein R ⁹ and R ¹⁰ are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkylcycloalkyl group having 6 to 12 carbon atoms, Represents an aralkyl group or a phenyl group of 12, R ¹¹ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, W is a mere bond, a sulfur atom or an alkyl group having 1 to 8 carbon atoms or 5 to 8 carbon atoms; Represents a methylene group which may be substituted by a cycloalkyl group.) 6. A compound of the formula (XII) (Wherein, R ¹ , R ² , R ³ and R ⁴ have the same meanings as defined in claim 1), phosphorus trihalide, and HO-X- ^RA (XIII). (Wherein X and ^RA represent the same meaning as in claim 1). The method for producing phosphites according to claims 1 to 5, wherein the reaction is carried out with a hydroxy compound represented by the following formula. 7. A stabilizer for an organic material comprising the phosphite according to claim 1 as an active ingredient. 8. The stabilizer according to claim 7, wherein the organic material is a thermoplastic resin. 9. The stabilizer according to claim 8, wherein the thermoplastic resin is a polyolefin. 10. A method for stabilizing an organic material, comprising incorporating the phosphites according to claim 1 into the organic material. 11. The method according to claim 1, wherein the organic material is a thermoplastic resin.
0 stabilization method. 12. The method according to claim 11, wherein the thermoplastic resin is a polyolefin. 13. A stabilized organic material composition comprising an organic material containing the phosphite according to claim 1. 14. The method according to claim 1, wherein the organic material is a thermoplastic resin.
3. The composition according to 3. 15. The composition according to claim 14, wherein the thermoplastic resin is a polyolefin.