JP2006321793A - Polyamine derivative - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a piperidylaminotriazine skeleton-having polyamine derivative or its salt, to provide a method for producing them, to provide a stabilizing agent comprising the compound, and to provide a stabilized polyolefin resin composition. <P>SOLUTION: This compound represented by the general formula (1) [X and Y are each identically or differently N(R<SP>5</SP>) or oxygen atom; R<SP>1</SP>is a 2 to 50C hydrocarbon group selected from linear alkyl groups, branched alkyl groups, and substituted or non-substituted cyclic alkyl groups, provided that one or more oxygen atoms or nitrogen atoms may be contained in each of the carbon chains; R<SP>2</SP>is H or a 1 to 9C alkyl; R<SP>3</SP>and R<SP>4</SP>are each identically or differently H, a 1 to 9C alkyl, a 1 to 9C alkoxy or a 2 to 9C acyl; R<SP>5</SP>is H or a 1 to 9C alkyl; (n) is an integer of 2 or 3] or its salt. The stabilizer for polyolefins, and the polyolefin resin composition. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

The present invention relates to a novel polyamine derivative having a piperidylaminotriazine skeleton and a method for producing them. Furthermore, the present invention relates to a stabilizer for polyolefins comprising the compound and a stabilized polyolefin resin composition.

Polymer materials such as polyolefins, especially hydrocarbon polymers, are lightweight and have a high degree of freedom in shape, and weather resistance is required from automobile-related applications to building material-related applications, agricultural film applications, and household appliance-related applications. Widely used in applications. Light stabilizers provide weather resistance to these polymer materials, and among them, hindered amine light stabilizers (HALS: Hindered Ami)
ne Light Stabilizer) is currently widely used as an essential resin additive.

Existing HALS are roughly classified into low molecular weight types with a molecular weight of less than 1000 and high molecular weight types with a molecular weight of 1000 or more. Depending on the use or combination of both, thin materials (thin layer polymer materials) and thick materials (polymer materials other than thin materials) ) Stabilization against light is achieved in both applications. However, in the low molecular weight type, it is difficult to continuously provide a stabilizing effect in thin applications, and bleeding out, fogging, sick house and the like derived from the low molecular weight type are also problematic. On the other hand, the high molecular weight type generally has low compatibility with the polyolefin resin, and it is difficult to provide a sufficient stabilizing effect.

Examples of the compound having two triazine rings as a polyamine derivative having a piperidylaminotriazine skeleton include those disclosed in Patent Document 1 or 2 with a wide range of structures.
Japanese Patent No. 2799588 Japanese Patent No. 2799589

The problem of the present invention is that the compound having a molecular weight of 1000 or more is highly compatible with polyolefin,
It is to provide a compound as a novel HALS that is easy to produce. It is also an object of the present invention to provide a method for producing the compound, a stabilizer for polyolefin comprising the compound, and a stabilized polyolefin resin composition.

As a result of intensive studies to achieve the above-mentioned problems, the present inventors have found polyamine derivatives having two piperidylaminotriazine skeletons having high compatibility with polyolefins, and further their production methods, stable polyolefins comprising the compounds, The present inventors have found an agent and a stabilized polyolefin resin composition and have completed the present invention.

（式中、Ｘ及びＹは同一または異なっていてもよく、Ｎ（Ｒ^５）または酸素原子を示し、
Ｒ^１は直鎖状、分岐鎖状または置換もしくは無置換の環状のアルキル基から選ばれる炭素数２〜５０の炭化水素基であり、炭素鎖の途中に酸素原子または窒素原子を含有していてもよく、Ｒ^２は水素原子または炭素数１〜９のアルキル基を示し、Ｒ^３及びＲ^４は同一または異なっていてもよく、水素原子、炭素数１〜９のアルキル基、炭素数１〜９のアルコキシ基または炭素数２〜９のアシル基を示し、Ｒ^５は水素原子または炭素数１〜９のアルキル基を示し、ｎは２または３の整数を示す。）で表される化合物またはその塩。 That is, according to the present invention, the general formula (1):

(Wherein X and Y may be the same or different and each represents N (R ⁵ ) or an oxygen atom;
R ¹ is a hydrocarbon group having 2 to 50 carbon atoms selected from a linear, branched, or substituted or unsubstituted cyclic alkyl group, and contains an oxygen atom or a nitrogen atom in the middle of the carbon chain. R ² represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, R ³ and R ⁴ may be the same or different, and a hydrogen atom, an alkyl group having 1 to 9 carbon atoms, 9 represents an alkoxy group having 9 carbon atoms or an acyl group having 2 to 9 carbon atoms, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, and n represents an integer of 2 or 3. Or a salt thereof.

Or, general formula (1):

(Wherein X and Y may be the same or different and each represents N (R ⁵ ) or an oxygen atom;
¹ is a hydrocarbon group having 2 to 50 carbon atoms selected from a linear or branched alkyl group, and may contain an oxygen atom or a nitrogen atom in the middle of the carbon chain, and R ² is a hydrogen atom Or an alkyl group having 1 to 9 carbon atoms, and R ³ and R ⁴ may be the same or different, and may be a hydrogen atom, an alkyl group having 1 to 9 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, or 2 to 2 carbon atoms. 9 represents an acyl group, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, and n represents an integer of 2 or 3. Or a salt thereof.

 According to the invention, the general formula (2):

(Wherein, X, Y, R ³ and R ⁴ are the same as those described in the general formula (1), and Z represents a halogen atom), and the general formula (3 ):

(In the formula, R ¹ is a hydrocarbon group having 2 to 50 carbon atoms selected from a linear, branched, or substituted or unsubstituted cyclic alkyl group, and an oxygen atom or a nitrogen atom is inserted in the middle of the carbon chain. R ² represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, and n represents an integer of 2 or 3). Formula (1):

(Wherein X and Y may be the same or different and each represents N (R ⁵ ) or an oxygen atom;
¹ is a hydrocarbon group having 2 to 50 carbon atoms selected from linear, branched, or substituted or unsubstituted alkyl groups, and contains an oxygen atom or a nitrogen atom in the middle of the carbon chain. R ² represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, and R ³ and R ⁴ may be the same or different from each other, and may be a hydrogen atom, an alkyl group having 1 to 9 carbon atoms, or 1 to 9 carbon atoms. An alkoxy group or an acyl group having 2 to 9 carbon atoms, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, and n represents an integer of 2 or 3. The method of manufacturing the compound represented by this is provided.

Furthermore, according to the present invention, at least one of the compound represented by the general formula (1) or a salt thereof
And a polyolefin resin composition obtained by adding 0.001 to 15 parts by weight of at least one of the compound represented by the general formula (1) or a salt thereof to 100 parts by weight of polyolefin. .

The polyamine derivative having two piperidylaminotriazine skeletons of the present invention has high compatibility with polyolefins despite being HALS having a molecular weight of 1000 or more, and effectively imparts light stability to the polyolefin resin composition. Furthermore, since the amine compound which is a raw material of the compound of the present invention can be easily produced, the production of this compound is also easy.

  Hereinafter, the present invention will be described in detail.

The polyamine derivative having a novel piperidylaminotriazine skeleton of the present invention is represented by the general formula (1).

X and Y may be the same or different and each represents N (R ⁵ ) or an oxygen atom, preferably N (R ⁵ ). When X or Y is N (R ⁵ ), R ⁵ is a hydrogen atom or an alkyl group having 1 to 9 carbon atoms. Examples of the alkyl group of 1 to 9 include linear and branched ones such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group,
An n-heptyl group, an n-octyl group, and an n-nonyl group can be exemplified. 2 to 2 carbon atoms
An alkyl group of 6 is preferred, and an n-butyl group is most preferred.

R ¹ represents a group having an alkyl group terminal having 2 to 50 carbon atoms, and is a hydrocarbon group having 2 to 50 carbon atoms selected from a linear, branched, or substituted or unsubstituted cyclic alkyl group, An oxygen atom or a nitrogen atom may be contained in the middle of the carbon chain. When the oxygen atom is contained in the middle of the carbon chain, R ¹ is represented by the general formula (4):

(In the formula, p represents an integer of 2 to 10, and R ⁶ represents a hydrocarbon group having 2 to 20 carbon atoms selected from a linear, branched, or substituted or unsubstituted cyclic alkyl group.) The group represented by these is shown. When a nitrogen atom is contained in the middle of the carbon chain, R ¹ is represented by the general formula (5):

(In the formula, q represents an integer of 2 to 10, and R ⁷ represents a hydrocarbon group having 2 to 20 carbon atoms selected from a linear, branched, or substituted or unsubstituted cyclic alkyl group.) The group represented by these is shown.

When R ¹ represents a linear or branched alkyl group, for example, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n- Pentyl group, n-hexyl group, n-heptyl group, sec-heptyl group, 1-propylbutyl group, n-octyl group, 2-ethylhexyl group, sec-octyl group, n-nonyl group, 1-butylpentyl group, n-decyl group, n-undecyl group, 1-pentylhexyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, 1-heptyloctyl group, n- Hexadecyl group, n-heptadecyl group, 1-octylnonyl group, n-octadecyl group, n-nonadecyl group, 1-nonyldecyl group, 1-heptadecyl group A tectadecyl group can be exemplified, and when R ¹ represents a substituted or unsubstituted cyclic alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclohexylmethyl group, and a 4-methylcyclohexylmethyl group can be exemplified.

When R ¹ is a group represented by the general formula (4), examples of R ⁶ include an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, and a tert-butyl group. N-pentyl group, n-hexyl group, n-heptyl group, sec-heptyl group, 1-
Propylbutyl group, n-octyl group, 2-ethylhexyl group, sec-octyl group, n-
Nonyl group, 1-butylpentyl group, n-decyl group, n-undecyl group, 1-pentylhexyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group 1-heptyloctyl group, n-hexadecyl group, n-heptadecyl group, 1-octylnonyl group, n-octadecyl group, n-nonadecyl group, 1-nonyldecyl group, 1-heptadecyloctadecyl group, cyclopentyl group, cyclohexyl group , Cycloheptyl group, methylcyclohexane group, 4-methylmethylcyclohexane group.

When R ¹ is a group represented by the general formula (5), examples of R ⁷ include an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, and a tert-butyl group. N-pentyl group, n-hexyl group, n-heptyl group, sec-heptyl group, 1-
Propylbutyl group, n-octyl group, 2-ethylhexyl group, sec-octyl group, n-
Nonyl group, 1-butylpentyl group, n-decyl group, n-undecyl group, 1-pentylhexyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group 1-heptyloctyl group, n-hexadecyl group, n-heptadecyl group, 1-octylnonyl group, n-octadecyl group, n-nonadecyl group, 1-nonyldecyl group, 1-heptadecyloctadecyl group, cyclopentyl group, cyclohexyl group , Cycloheptyl group, methylcyclohexane group, 4-methylmethylcyclohexane group.

R ¹ is preferably a linear or branched alkyl group having 2 to 35 carbon atoms, more preferably a linear or branched alkyl group having 4 to 35 carbon atoms, still more preferably carbon. It is a linear or branched alkyl group having 4 to 18 carbon atoms, and most preferably a linear or branched alkyl group having 6 to 18 carbon atoms.

R ² represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, and includes straight-chain and branched-chain ones such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl. Group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group and n-nonyl group. A hydrogen atom and an alkyl group having 1 to 4 carbon atoms are preferable, and a hydrogen atom and a methyl group are most preferable.

R ³ and R ⁴ may be the same or different and may be a hydrogen atom, an alkyl group having 1 to 9 carbon atoms,
An alkoxy group having 1 to 9 carbon atoms or an acyl group having 2 to 9 carbon atoms is shown. Examples of the alkyl group having 1 to 9 carbon atoms include straight-chain and branched-chain alkyl groups such as methyl group, ethyl group, n
-Propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, te
rt-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group,
An n-nonyl group can be mentioned. Examples of the alkoxy group having 1 to 9 carbon atoms include straight-chain and branched-chain groups such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group. Group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group and nonyloxy group. Examples of the acyl group having 2 to 9 carbon atoms include straight-chain and branched-chain groups such as acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, pivaloyl group, acryloyl group, propioroyl group. ,
A methacryloyl group and a crotonoyl group can be mentioned. R ³ and R ⁴ are preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 8 carbon atoms and an acetyl group, and most preferably a hydrogen atom and a methyl group.

As a halogen atom of Z in General formula (2), a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom can be mentioned, for example.

The salt of the compound represented by the general formula (1) of the present invention includes a salt with an inorganic acid or an organic acid. In this case, examples of the inorganic acid include hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, carbonic acid, phosphoric acid and the like. The organic acid may be either an optically active organic acid or a non-optically active organic acid, such as formic acid, acetic acid, propionic acid, benzoic acid,
Examples thereof include carboxylic acids such as trifluoroacetic acid, tartaric acid and mandelic acid; sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid; amino acids and derivatives thereof. The composition ratio of the compound of the present invention and the acid in the salt is
It may be an equivalent value or an arbitrary value.

[Method for producing compound of the present invention]
The compound represented by the general formula (1) of the present invention is represented by the general formula (2):

(Wherein, X, Y, R ³ , R ⁴ and Z are as defined above) and the general formula (3):

(In the formula, R ¹ is a hydrocarbon group having 2 to 50 carbon atoms selected from a linear, branched, or substituted or unsubstituted cyclic alkyl group, and an oxygen atom or a nitrogen atom is inserted in the middle of the carbon chain. R ² represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, n represents an integer of 2 or 3, and can be produced by coupling.

The compound having two amino group ends represented by the general formula (3) used as a raw material for this reaction is a commercially available amine having a linear, branched, or substituted or unsubstituted cyclic alkyl chain end. Can be easily obtained by a known synthesis method. For example, it can be synthesized by the method described in Patent Document 3 (Japanese Patent Publication No. Hei 6-506501) and Patent Document 4 (Japanese Patent Publication No. 9-508170), and coupled with the general formula (2). The compound represented by the general formula (1) can be easily produced.

Hereinafter, a method of obtaining the compound represented by the general formula (1) of the present invention by the reaction of the compound represented by the general formula (2) and the compound represented by the general formula (3) will be described in more detail. To do.

The molar ratio of the compound represented by the general formula (2) and the compound represented by the general formula (3) is most preferably 2: 1, but either one of the compounds may be supplied in an excessive amount. . When an excessive amount is used, the amount is 1.01 to 10.0 times the preferable amount. There are no particular restrictions on how both compounds are charged into the reactor. For example, the entire amount of both compounds may be transferred to the reactor all at once, and the reaction may be started, or the other compound may be reacted in one compound. You may add gradually, making it go.

The reaction may be carried out in the presence of a deoxidizer. Examples of the deoxidizer used include inorganic salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate; triethylamine,
Tributylamine, pyridine, N, N-dimethylaniline, N-methylimidazole, 1
, 8-diazabicyclo [5.4.0] undec-7-ene (DBU).

The solvent used for the reaction is not particularly limited as long as it does not affect the reaction. For example, water; saturated hydrocarbons such as pentane, hexane, heptane, cyclohexane;
Aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, ethylbenzene;
Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, 1,3-
Ethers such as dioxane, 1,4-dioxane, tetrahydrofuran, dimethyl ether, diethyl ether, diisopropyl ether, dibutyl ether; amides such as N, N-dimethylformamide; nitriles such as acetonitrile; acetone, methyl ethyl ketone, methyl isobutyl ketone, etc. Ketones; esters such as methyl acetate and ethyl acetate; sulfur-containing solvents such as dimethyl sulfoxide; N, N-dimethylformamide (DMF), 1,3-dimethyl-2-imidazolidinone (DMI) Can do.

These solvents are used alone or as a mixture, and when used as a mixture, they can be used in any ratio. In addition, the compound represented by the general formula (2) of the raw material and the compound represented by the general formula (3) may be reacted by dissolving in a reaction solvent, or may be reacted in a slurry state. When a mixture of an organic solvent that is incompatible with water and water is selected as a reaction solvent, a phase transfer catalyst such as a tetrabutylammonium salt (for example, tetrabutylammonium hydrogen sulfate) may coexist.

Although the usage-amount of a reaction solvent is not specifically limited, It is 1-1000g with respect to 1g of compounds represented by General formula (2) of a raw material, Preferably it is 1-500g, More preferably, it is the range of 1-100g.

The reaction is carried out in the temperature range from 0 ° C. to the boiling point of the solvent. Preferably, 50 ° C to 15
Performed at 0 ° C. In addition, when reacting in an autoclave, it is not limited to the said temperature range, It is 0-300 degreeC, Preferably it implements in the range of 0-250 degreeC.

The reaction time is not particularly limited and can be appropriately determined according to the raw materials, reaction conditions and the like, but is usually 10 minutes to 72 hours.

The isolation method of the compound represented by the general formula (1) of the present invention is not particularly limited. If the product is precipitated from the reaction solvent, it can be isolated by filtration or centrifugation, and if dissolved in the reaction solvent, the solvent can be distilled off under reduced pressure or an appropriate solvent can be added. It is possible to adopt a method of precipitating and then filtering or centrifuging. Moreover, the said operation may be performed by forming a salt by treating with an appropriate acid, or a combination of these methods.

When purification is required for the compound represented by the general formula (1) of the present invention, a method well known as a conventional method can be employed. For example, a recrystallization method, a column chromatography method,
Examples thereof include washing with solvent (sludge treatment) and activated carbon treatment. These purifications may be performed after the compound represented by the general formula (1) is treated with an appropriate acid to form a salt.

The solvent used for the recrystallization method, column chromatography method, washing with a solvent, and activated carbon treatment is not particularly limited. For example, water, aqueous ammonia; saturated hydrocarbons such as pentane, hexane, heptane, cyclohexane; benzene, toluene Aromatic hydrocarbons such as xylene, ethylbenzene; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; methanol, ethanol, 1-propanol, isopropyl alcohol, tert-butyl alcohol, etc. Lower alcohols; ethylene glycol, diethylene glycol, propylene glycol and other glycols; ethylene glycol dimethyl ether, 1,3-dioxane, 1,4-dioxane, teto Hydrofuran, dimethyl ether, diethyl ether,
Ethers such as diisopropyl ether and dibutyl ether; formamide, N, N-
Amides such as dimethylformamide; Nitriles such as acetonitrile; Ketones such as acetone and methyl ethyl ketone; Carboxylic acids such as formic acid and acetic acid; Esters such as methyl acetate and ethyl acetate; Sulfur-containing solvents such as dimethyl sulfoxide; N, N -Dimethylformamide (DMF), 1,3-dimethyl-2-imidazolidinone and the like can be mentioned.

These solvents are used alone or as a mixture, and when used as a mixture, they can be used in any ratio.

The amount of the solvent used during recrystallization, sludge treatment and activated carbon treatment is in the range of 1 to 1000 g, preferably 1 to 300 g, relative to 1 g of the compound represented by the general formula (1).

In the general formula (1), a compound in which at least one of R ^{3 and} R ⁴ is a methyl group is
Using 1,2,2,6,6-pentamethyl-4-piperidone as a starting material, the compound represented by the general formula (3) is once led to a compound in which at least one of R ^{3 and} R ⁴ is a methyl group in the general formula (2).
It can be made to react with the compound represented by this. In the general formula (1), R ³ and R
It is also possible to produce a compound in which ⁴ is a hydrogen atom by causing an Eschweiler-Clark reaction.

Here, the Eschweiler-Clark reaction is Leuckart-Walla.
A type of ch reaction, which uses formaldehyde for amine methylation.

In general formula (1), a compound in which at least one of R ³ or R ⁴ is a methyl group and R ² is a methyl group is a compound represented by general formula (1) wherein R ³ and R ⁴ are hydrogen atoms and R ² is hydrogen. A compound that is an atom or a compound in which at least one of R ³ or R ⁴ is a methyl group and R ² is a hydrogen atom can be synthesized by an Eschweiler-Clark reaction.

  The compound represented by the general formula (1) of the present invention is represented by the general formula (6):

(Wherein X and R ³ are as defined above.)
Or general formula (7):

(Wherein Y and R ⁴ are as defined above.)
The compound represented by formula (2) is reacted with cyanuric halide such as cyanuric chloride to lead to the compound represented by the general formula (2), and is represented by the general formula (3) in one pot without isolation. It can also be produced by reacting with a compound. These reactions are performed under the same conditions as the reaction of the compound represented by the general formula (2) and the compound represented by the general formula (3) described above.

[Polyolefins that can be stabilized]
The compound represented by the general formula (1) of the present invention is very effective in improving the photostability of polyolefin. The light includes not only visible light but also ultraviolet light and infrared light, and is effective in improving the stability to light having a single wavelength or light having a plurality of wavelengths. Especially 390n
It is also effective for light of m to 420 nm. It can also be used to improve the stability of polyolefin against deterioration by heat and oxygen. Here, oxygen includes not only molecular oxygen but also active oxygen. Examples of active oxygen include singlet oxygen, hydroxyl radical,
An alkoxy radical, a peroxy radical, a hydroperoxide, etc. can be mentioned.

  Examples of polyolefins that can be stabilized are shown below.

1. Monoolefin, diolefin and cycloolefin polymers, specifically
Monoolefin polymers include polypropylene, polyisobutylene, polybutene
1, poly (4-methylpentene-1), high density polyethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HMW), high density and ultra high molecular weight polyethylene (H
DPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE)
), Linear low density polyethylene (LLDPE), branched low density polyethylene (BLDP)
E) In addition, as diolefin polymers, polyisoprene, polybutadiene, and cycloolefin polymers as cyclopentene or norbornene polymers, copolymers of cycloolefin and ethylene (COC), and ring opening of cycloolefins. Examples thereof include a polymer and its hydrogenated product (COP), polystyrene and its hydrogenated product (PCHE), and these polyolefins can be used after being crosslinked by a known method if desired.

2. 1. Mixtures of the polymers described in e.g. polypropylene and polyisobutylene, polypropylene and polyethylene (e.g. PP / HDPE, PP / L
DPE) and various types of mixtures of polyethylene (eg LDPE / HDPE, L
LDPE / LDPE).

3. Copolymers of monoolefins and diolefins with each other or with other vinyl monomers, such as ethylene / propylene copolymers, propylene / butene-1 copolymers, propylene / isobutylene copolymers, ethylene / butene-1 copolymers, ethylene /
Hexene copolymer, ethylene / methylpentene copolymer, ethylene / heptene
Copolymer, ethylene / octene copolymer, propylene / butadiene copolymer,
Isobutylene / isoprene copolymer, ethylene / alkyl acrylate copolymer, ethylene / alkyl methacrylate copolymer, ethylene / vinyl acetate copolymer and copolymers of these with carbon monoxide or ethylene / acrylic acid
Copolymers and their salts (ionomers), and terpolymers of ethylene and propylene with dienes such as hexadiene, dicyclopentadiene or ethylidene-norbornene; Mixtures with the polymers described in e.g. polypropylene / ethylene-propylene-copolymer, LDPE /
Ethylene-vinyl acetate (EVA) copolymer, LDPE / ethylene acrylic acid (E
AA) copolymers, LLDPE / EVA, LLDPE / EAA and random or alternating polyalkylene / carbon monoxide copolymers; and mixtures of these copolymers with other polymers such as polyamides.

The compound represented by the general formula (1) is particularly preferable for improving the light stability of polyethylene and polypropylene among the polyolefins.

[Method for stabilizing polyolefin]
A method for stabilizing a polyolefin against deterioration due to light, oxygen and the like is to mix at least one compound represented by the general formula (1) or a salt thereof, or a mixture thereof in the polyolefin. is there. The compound of general formula (1) or a salt thereof, or a mixture thereof can be used in various proportions depending on the nature of the material to be stabilized, the end use and depending on the presence of other additives. .

In general, for example, 0.001-15 with respect to 100 parts by weight of the polyolefin to be stabilized
It is appropriate to use parts by weight, preferably 0.01 to 5 parts by weight, more preferably 0.05 to 3 parts by weight of the compound of the general formula (1) or a salt thereof, or a mixture thereof.

The compound of the general formula (1) or a salt thereof, or a mixture thereof can be introduced into the polyolefin at various convenient steps of the material before producing the molding material, for example before, during or after polymerization or crosslinking. Can be added. Furthermore, they are miscible in the polyolefin in pure form or in the form of waxes, oils or polymers encapsulated.

The compound of general formula (1) or a salt thereof, or a mixture thereof can be obtained by various methods, for example by dry mixing in the form of a powder or by wet mixing in the form of a solution or suspension or in the form of a masterbatch Can also be incorporated into the polyolefin; and in such operations, the polyolefin can be used in the form of powders, granules, solutions, suspensions or in the form of latex.

The material stabilized with the compound of the general formula (1) or a salt thereof, or a mixture thereof can be used, for example, for the production of molded articles, films, tapes, monofilaments, fibers, surface coatings, coating compositions and the like. . In addition, the stabilized material can be used for manufacturing an optical element, and the optical element can also be used for an optical pickup device. Further, the optical element is used in a pickup device having at least one wavelength of 390 nm to 420 nm. It can be used also for what is used.

[Additives that can be used in combination]
The polyolefin containing the compound of the general formula (1) or a salt thereof, or a mixture thereof may optionally contain other conventional additives for polyolefins such as antioxidants, ultraviolet absorbers, light stabilizers, pigments, Fillers, plasticizers, antistatic agents, flame retardants, lubricants, corrosion inhibitors and metal deactivators can be added in combination.

  Examples of the additive include the following.

1. Antioxidants (1.1) Alkylated monophenols such as 2,6-di-tert-butyl-4-
Methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-
tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-
Di-cyclopentyl-4-methylphenol, 2- (α-methylcyclohexyl) -4,
6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6
-Tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenol with linear or branched side chains, for example 2,6-dinonyl-4-methylphenol, 2,4-dimethyl -6- (1'-methylundec-1'-yl) phenol, 2,4-dimethyl-6- (1'-methylheptadec-1'-yl) phenol, 2,4-dimethyl-6- (1'-methyltridecyl) -1'-yl) phenol and mixtures thereof.

(1.2) Alkylthiomethylphenol, for example 2,4-di-octylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl -6-ethylphenol and 2,6-di-dodecylthiomethyl-4-nonylphenol.

(1.3) Hydroquinone and alkylated hydroquinone, such as 2,6-di-tert-
Butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5
-Di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5- Di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis (3
5-Di-tert-butyl-4-hydroxyphenyl) adipate.

(1.4) Tocopherols, for example α-tocopherol, β-tocopherol, γ-
Tocopherol, δ-tocopherol and mixtures thereof (vitamin E).

(1.5) Hydroxylated thiodiphenyl ether such as 2,2′-thiobis (6
-Tert-butyl-4-methylphenol), 2,2'-thiobis (4-octylphenol), 4,4'-thiobis (6-tert-butyl-3-methylphenol), 4,
4'-thiobis (6-tert-butyl-2-methylphenol), 4,4'-thio-bis (3,6-di-sec-amylphenol), 4,4'-bis (2,6-dimethyl) -4
-Hydroxyphenyl) disulfide.

(1.6) alkylidene bisphenols such as 2,2′-methylene-bis (6-t
ert-butyl-4-methylphenol), 2,2′-methylene-bis (6-tert-
Butyl-4-ethylphenol), 2,2′-methylene-bis [4-methyl-6- (α-
Methylcyclohexyl) phenol], 2,2'-methylene-bis (4-methyl-6-cyclohexylphenol), 2,2'-methylene-bis (6-nonyl-4-methylphenol), 2,2'-methylene -Bis (4,6-di-tert-butylphenol), 2,
2′-ethylidene-bis (4,6-di-tert-butylphenol), 2,2′-ethylidene-bis (6-tert-butyl-4-isobutylphenol), 2,2′-methylene-bis [6- (Α-methylbenzyl) -4-nonylphenol], 2,2′-methylene-bis [6- (α, α-dimethylbenzyl) -4-nonylphenol], 4,4′-methylene-bis (2,6- Di-tert-butylphenol), 4,4′-methylene-bis (
6-tert-butyl-2-methylphenol), 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 2,6-bis (3-tert-butyl-5-methyl) -2-hydroxybenzyl) -4-methylphenol, 1,1,3-tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 1,1-bis (5-tert-butyl-4) -Hydroxy-2-methylphenyl) -3-n-dodecyl mercaptobutane, ethylene glycol bis [3,3-bis (3'-tert-butyl-4
'-Hydroxyphenyl) butyrate], bis (3-tert-butyl-4-hydroxy-5-methylphenyl) dicyclopentadiene, bis [2- (3'-tert-butyl-
2′-hydroxy-5′-methylbenzyl) -6-tert-butyl-4-methylphenyl] terephthalate, 1,1-bis (3,5-dimethyl-2-hydroxyphenyl) butane, 2,2-bis ( 3,5-di-tert-butyl-4-hydroxyphenyl) propane, 2,2-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) -4-
n-dodecyl mercaptobutane and 1,1,5,5-tetrakis (5-tert-butyl-4-hydroxy-2-methylphenyl) pentane.

(1.7) O-, N- and S-benzyl compounds, such as 3,5,3 ', 5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4
-Hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate, tris (3,5
-Di-tert-butyl-4-hydroxybenzyl) amine, bis (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) -dithioterephthalate, bis (3
5-di-tert-butyl-4-hydroxybenzyl) sulfide and isooctyl-
3,5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate.

(1.8) Hydroxybenzylated malonate, such as dioctadecyl-2,2-bis (3,5-di-tert-butyl-2-hydroxybenzyl) -malonate, di-octadecyl-2- (3-tert-butyl -4-hydroxy-5-methylbenzyl) -malonate, di-dodecyl mercaptoethyl-2,2-bis (3,5-di-tert-butyl-
4-hydroxybenzyl) -malonate and bis [4- (1,1,3,3-tetramethylbutyl) phenyl] -2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl) -Malonate.

(1.9) Hydroxybenzyl aromatic compounds such as 1,3,5-tris (3,5-
Di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene,
1,4-bis (3,5-di-tert-butyl-4-hydroxybenzyl) -2,3,5
, 6-tetramethylbenzene and 2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) phenol.

(1.10) Triazine compounds such as 2,4-bis (octyl mercapto) -6
-(3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4- Hydroxyanilino) -1,3,5-triazine, 2-octylmercapto-4,6-bis (
3,5-di-tert-butyl-4-hydroxyphenoxy) -1,3,5-triazine, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenoxy)-
1,2,3-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tert-butyl-3)
-Hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6-tris (3
, 5-Di-tert-butyl-4-hydroxyphenylethyl) -1,3,5-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro 1,3,5-triazine, 1,3,5-tris (3,5-dicyclohexyl-4-hydroxybenzyl) isocyanurate.

(1.11) Benzylphosphonates such as dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-
4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-
Hydroxy-3-methylbenzylphosphonate and 3,5-di-tert-butyl-4
-Ca salt of hydroxybenzylphosphonic acid monoethyl ester.

(1.12) acylaminophenol, such as lauric acid 4-hydroxyanilide,
Stearic acid 4-hydroxyanilide, carbamic acid N- (3,5-di-tert-butyl-4-hydroxyphenyl) octyl ester.

(1.13) Esters of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with the following mono- or polyhydric alcohols such as methanol, ethanol, n-octanol, i- Octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) ) Isocyanurate, N
, N′-bis (hydroxyethyl) oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7- Trioxabicyclo [2.2.2] octane.

(1.14) β- (5-tert-butyl-4-hydroxy-3-methylphenyl)
Esters of propionic acid with the following mono- or polyhydric alcohols such as methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol,
Neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N′-bis (hydroxyethyl) oxalic acid diamide, 3-thiaundecanol, 3
-Thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-
Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane.

(1.15) Esters of β- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid with the following mono- or polyhydric alcohols such as methanol, ethanol,
Octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (
Hydroxyethyl) isocyanurate, N, N′-bis (hydroxyethyl) oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha -2,6,7-trioxabicyclo [2.2.2] octane.

(1.16) Esters of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid with the following mono- or polyhydric alcohols such as methanol, ethanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1
, 2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N′-bis (hydroxyethyl) oxalic acid diamide, 3
-Thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane.

(1.17) Amides of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid, such as N, N′-bis (3,5-di-tert-butyl-4-hydroxyphenyl) Propionyl) hexamethylenediamine, N, N′-bis (3,5-di-t
ert-butyl-4-hydroxyphenylpropionyl) trimethylenediamine, N, N
'-Bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazine.

  (1.18) Ascorbic acid (vitamin C)

(1.19) Amine-based antioxidants such as N, N′-diisopropyl-p-phenylenediamine, N, N′-sec-butyl-p-phenylenediamine, N, N′-bis (1
, 4-Dimethylpentyl) -p-phenylenediamine, N, N′-bis (1-ethyl-3)
-Methylpentyl) -p-phenylenediamine, N, N'-bis (1-methylheptyl)
-P-phenylenediamine, N, N'-dicyclohexyl-p-phenylenediamine, N
, N'-diphenyl-p-phenylenediamine, N, N'-di (2-naphthyl) -p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-
(1,3-dimethylbutyl) -N′-phenyl-p-phenylenediamine, N- (1-methylheptyl) -N′-phenyl-p-phenylenediamine, N-cyclohexyl-N ′
-Phenyl-p-phenylenediamine, 4- (p-toluenesulfonamido) diphenylamine, N, N'-dimethyl-N, N'-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-iso Propoxydiphenylamine,
N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, p, p'-di-tert-butyl-octyldiphenylamine, 4-n
-Butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylaminophenol,
Bis (4-methoxyphenyl) amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, N, N, N ′, N '-Tetramethyl-4,4'-diaminodiphenylmethane, 1,2-bis [(2-methylphenyl) amino] ethane, 1,2-bis (phenylamino) propane, (o-tolyl) biguanide, bis [4 -(1 ', 3'-dimethylbutyl) phenyl] amine, tert-octylated N-phenyl-1-naphthylamine, mono-
And mixtures of dialkylated tert-butyl / tert-octyldiphenylamine,
Mono- and dialkylated isopropyl / isohexyldiphenylamine mixtures, mono- and dialkylated tert-butyldiphenylamine mixtures, 2,3-dihydro-
3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, N-allylphenothiazine, N, N, N ′, N′-tetraphenyl-1,4-diaminobut-2-ene, N
, N-bis (2,2,6,6-tetramethylpiperidi-4-yl-hexamethylenediamine, bis (2,2,6,6-tetramethylpiperidi-4-yl) sebacate, 2,2 , 6
, 6-Tetramethylpiperidin-4-one and 2,2,6,6-tetramethylpiperidin-4-ol.

2. UV absorbers and light stabilizers (2.1) 2- (2′-hydroxyphenyl) benzotriazole, such as 2- (
2'-hydroxy-5'-methylphenyl) benzotriazole, 2- (3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (5'-t
ert-butyl-2′-hydroxyphenyl) benzotriazole, 2- (2′-hydroxy-5 ′-(1,1,3,3-tetramethylbutyl) phenyl) benzotriazole,
2- (3 ′, 5′-di-tert-butyl-2′-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3′-tert-butyl-2′-hydroxy-5′-methylphenyl)- 5-chlorobenzotriazole, 2- (3′-sec-butyl-5′-ter
t-butyl-2′-hydroxyphenyl) benzotriazole, 2- (2′-hydroxy-4′-octoxyphenyl) benzotriazole, 2- (3 ′, 5′-di-tert-
Amyl-2′-hydroxyphenyl) benzotriazole, 2- (3 ′, 5′-bis (α
, Α-dimethylbenzyl) -2′-hydroxyphenyl) benzotriazole, 2- (3
'-Tert-butyl-2'-hydroxy-5'-(2'-octyloxycarbonylethyl) phenyl) -5-chlorobenzotriazole, 2- (3'-tert-butyl-5
'-[2- (2-Ethylhexyloxy) carbonylethyl] -2'-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5'-(2-methoxy) Carbonylethyl) phenyl) -5-chlorobenzotriazole, 2- (3′-tert-butyl-2′-hydroxy-5 ′-(2-methoxycarbonylethyl) phenyl) benzotriazole, 2- (3′-tert- Butyl-2′-hydroxy-5 ′-(2-octoxycarbonylethyl) phenyl) benzotriazole, 2
-(3'-tert-butyl-5 '-[2- (2-ethylhexyloxy) carbonylethyl] -2'-hydroxyphenyl) benzotriazole, 2- (3'-dodecyl-2'
-Hydroxy-5'-methylphenyl) benzotriazole, and 2- (3'-ter
A mixture of t-butyl-2′-hydroxy-5 ′-(2-isooctyloxycarbonylethyl) phenylbenzotriazole, 2,2′-methylene-bis [4- (1,1,3,3
-Tetramethylbutyl) -6-benzotriazol-2-ylphenol], 2- [3 '
A transesterification product of tert-butyl-5 ′-(2-methoxycarbonylethyl) -2′-hydroxyphenyl] benzotriazole with polyethylene glycol 300, [
R ²¹ —CH ₂ CH ₂ —COO (CH ₂ ) ₃ —] ₂ — (wherein R ²¹ represents 3′-tert-
Butyl-4′-hydroxy-5′-2H-benzotriazol-2-ylphenyl. ).

(2.2) 2-hydroxybenzophenones, for example 4-hydroxy-, 4-methoxy-, 4-octoxy-, 4-decyloxy-, 4-dodecyloxy-, 4-benzyloxy-, 4,2 ', 4 '-Trihydroxy- or 2'-hydroxy-4,4'-dimethoxy derivatives.

(2.3) Substituted or unsubstituted esters of benzoic acid, such as 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis (4-tert-butylbenzoyl) resorcinol, Benzoyl resorcinol, 2,4-di-tert-butylphenyl = 3,5-di-
tert-Butyl-4-hydroxybenzoate, hexadecyl = 3,5-di-tert
-Butyl-4-hydroxybenzoate, octadecyl = 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl =
3,5-di-tert-butyl-4-hydroxybenzoate.

(2.4) acrylates such as 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.

(2.5) Nickel compounds, for example nickel complexes of 2,2′-thiobis [4- (1,1,3,3-tetramethylbutyl) phenol], for example 1: 1 or 1: 2 complexes, N-butylamine, triethanolamine or N-cyclohexyl- if desired
With other ligands such as di-ethanolamine, nickel dibutyldithiocarbamate, 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid monoalkyl ester, for example nickel salt of methyl or ethyl ester, ketoxime For example, 2-hydroxy-4-methyl-phenylundecyl ketoxime nickel complex, 1-phenyl-
Nickel complex of 4-lauroyl-5-hydroxypyrazole, optionally with other ligands.

(2.6) Sterically hindered amines such as bis (2,2,6,6-tetramethylpiperidyl) sebacate, bis (2,2,6,6-tetramethylpiperidyl) succinate, bis (1,2,2) , 6,6-pentamethylpiperidyl) sebacate, bis (1,2,2,6,
6-pentamethylpiperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl-4-hydroxy A condensation product of piperidine and succinic acid, N, N′-bis (2,2,6
, 6-Tetramethyl-4-piperidyl) hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-s-triazine, tris (2
, 2,6,6-tetramethyl-4-piperidyl) nitrilotriacetate, tetrakis (
2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate, 1,1 ′-(1,2-ethanediyl) -bis (3,3,5, 5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-
Stearyloxy-2,2,6,6-tetramethylpiperidine, bis (1,2,2,6,
6-Pentamethylpiperidyl) -2-n-butyl-2- (2-hydroxy-3,5-di-
tert-butylbenzyl) malonate, 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5] decane-2,4-dione, bis (1-octyloxy) -2,2,6,6-tetramethylpiperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethylpiperidyl) succinate, N, N'-bis (
2,2,6,6-tetramethyl-4-piperidyl) -hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine condensation product, 2-chloro-4,
6-bis (4-n-butylamino-2,2,6,6-tetramethylpiperidyl) -1,3
, 5-Triazine and 1,2-bis (3-aminopropylamino) ethane condensation product, 2
-Chloro-4,6-di (4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl) -1,3,5-triazine and 1,2-bis (3-aminopropylamino) ) Condensation product with ethane, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3
, 8-triazaspiro [4.5] decane-2,4-dione, 3-dodecyl-1- (2,2
, 6,6-tetramethyl-4-piperidyl) pyrrolidine-2,5-dione, 3-dodecyl-1- (1,2,2,6,6-pentamethyl-4-piperidyl) -pyrrolidine-2,5-
Dione, a mixture of 4-hexadecyloxy and 4-stearoyloxy-2,2,6,6-tetramethylpiperidine, N, N′-bis (2,2,6,6-tetramethyl-4-piperidyl) Hexamethylenediamine and 4-cyclohexylano-2,6-dichloro-1,3
1,5-triazine condensation product, 1,2-bis (3-aminopropylamino) ethane and 2
, 4,6-dichloro-1,3,5-triazine condensation product and 4-butylamino-2
, 2,6,6-tetramethylpiperidine (CAS Reg. No [136504-96-
6]), N- (2,2,6,6-tetramethyl-4-piperidyl) -n-dodecylsuccinimide, N- (1,2,2,6,6-pentamethyl-4-piperidyl)- n-dodecylsuccinimide, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro [4.5] decane, 7,7,9, Reaction product of 9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro [4.5] decane and epichlorohydrin.

(2.7) Oxamides such as 4,4′-dioctyloxyoxanilide, 2,2
'-Diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-
Butoxanilide, 2,2′-didodecyloxy-5,5′-di-tert-butoxanilide, 2-ethoxy-2′-ethoxanilide, N, N′-bis (3-dimethylaminopropyl) oxamide, 2-ethoxy- 5-tert-butyl-2'-ethyloxanilide and mixtures of said compound with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, o- and p-methoxy-disubstituted oxanilide And o- and p-
Mixture of ethoxy-disubstituted oxanilides.

(2.8) 2- (2-hydroxyphenyl) -1,3,5-triazine, for example 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-dimethyl) -1,3,5-triazine,
2- (2-hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-tridecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2
-[2-hydroxy-4- (2-hydroxy-3-octyloxypropyloxy) phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [
4- (dodecyloxy / tridecyloxy-2-hydroxypropoxy) -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine,
2- [2-hydroxy-4- (2-hydroxy-3-dodecyloxypropoxy) phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2
-Hydroxy-4-hexyloxy) phenyl-4,6-diphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-methoxyphenyl-4,6-diphenyl-1,3)
, 5-triazine, 2,4,6-tris [2-hydroxy-4- (3-butoxy-2-hydroxypropoxy) phenyl] -1,3,5-triazine, 2- (2-hydroxyphenyl) -4 -(4-Methoxyphenyl) -6-phenyl-1,3,5-triazine.

3. Metal deactivators such as N, N′-diphenyloxalic acid diamide, N-salicyl-N′-salicyloylhydrazine, N, N′-bis (salicyloyl) hydrazine, N,
N′-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-1,2,4-triazole, bis (benzylidene)
Oxalic acid dihydrazide, oxanilide, isophthalic acid dihydrazide, sebacic acid-bis-
Phenylhydrazide, N, N′-diacetal-adipic acid dihydrazide, N, N′-bis-salicyloyl-oxalic acid dihydrazide, N, N′-bis-salicyloyl-thiopropionic acid dihydrazide.

4). Phosphites (phosphites) and phosphonites such as triphenyl phosphite, diphenylalkyl phosphite, phenyl dialkyl phosphite, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol di Phosphite, Tris (2,4-di-te
rt-butylphenyl) phosphite, diisodecylpentaerythritol diphosphite, bis (2,4-di-tert-butylphenyl) -pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methyl) Phenyl) -pentaerythritol diphosphite, di-isodecyloxy-pentaerythritol diphosphite, bis (2,4-di-tert-butyl-6-methylphenyl) -pentaerythritol diphosphite, bis (2,4 , 6-Tris-tert-butylphenyl) -pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2
, 4-Di-tert-butylphenyl) 4,4′-biphenylenediphosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz [
d, g] -1,3,2-dioxaphosphocin, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz [d, g] -1,3,2 -Dioxaphosphocin, bis (2,4-di-tert-butyl-6-methylphenyl) methyl phosphite, bis (2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite.

5. Hydroxylamines such as N, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N-dioctylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-ditetradecylhydroxylamine, N, N, N-Dialkyl derived from N-dihexadecylhydroxylamine, N, N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, hydrogenated tallowamine Hydroxylamine.

6). Nitrones such as N-benzyl-α-phenylnitrone, N-ethyl-α-methylnitrone, N-octyl-α-heptylnitrone, N-lauryl-α-undecylnitrone, N-tetradecyl-α-tridecylnitrone N-hexadecyl-α-pentadecyl nitrone, N-octadecyl-α-heptadecyl nitrone, N-hexadecyl-α-heptadecyl nitrone, N-octadecyl-α-pentadecyl nitrone, N-heptadecyl-α-heptadecyl nitrone N-octadecyl-α-hexadecylnitrone, a nitrone derived from N, N-dialkylhydroxylamine derived from hydrogenated tallowamine.

7). Thio synergists such as dilauryl thiodipropionate or distearyl thiodipropionate.

8). Peroxide scavengers such as esters of β-thiodipropionic acid, such as lauryl, stearyl, myristyl or tridecyl esters, mercaptobenzimidazole, or zinc salts of 2-mercaptobenzimidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, Pentaerythritol tetrakis (β-dodecylmercapto) propionate.

9. Basic co-stabilizers such as melamine, polyvinylpyrrolidone, dicyandiamide,
Triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids such as stearic acid C
a salt, Zn stearate, Mg behenate, Mg stearate, sodium ricinoleate and palmitic acid K salt, catechol antimony salt and catechol tin salt.

10. Nucleating agents such as inorganic substances such as metal oxides such as talc, titanium dioxide or magnesium oxide, preferably alkaline earth metal phosphates, carbonates or sulfates; organic compounds such as mono- or polycarboxylic acids And its salts, for example, 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymerizable compounds such as ionic copolymers (ionomers).

11. Fillers and reinforcing agents such as calcium carbonate, silicates, glass fibers, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite.

12 Other additives such as plasticizers, lubricants, emulsifiers, pigments, rheology additives
(Rheology additives), catalysts, flow control agents, brighteners, flame retardants, antistatic agents and foaming agents.

The weight ratio of the compound represented by the general formula (1) or a salt thereof, or a mixture thereof to a conventional additive may be 1: 0.001 to 1: 200.

The compound of the general formula (1) or a salt thereof, or a mixture thereof is useful for polyethylene or polypropylene to which a pigment is added.

EXAMPLES Hereinafter, although this invention is demonstrated further more concretely based on an Example, this invention is not limited to these Examples. All percentages represent percentages by weight unless otherwise specified. The melting point indicates the temperature at the end of melting when a sample is collected in a capillary to a thickness of about 2 to 3 mm and heated in a bath solution.

Example 1
Production of compound represented by formula (8)

(1) Synthesis of N, N-bis (2-cyanoethyl) hexylamine Acrylonitrile 20 was added to an aqueous solution (150 ml) of 15.5 g of hexylamine at room temperature.
. 1 g was added dropwise over 0.5 hours, and then stirred at 70 ° C. for 3 hours. After allowing to cool to room temperature, 150 ml of ethyl acetate was added for extraction. The organic layer obtained by liquid separation was dried over anhydrous magnesium sulfate, and then the solvent was distilled off to obtain 31.4 g of the title compound as a colorless oil.
¹ H NMR (CDCl ₃ ): δ = 0.89 (3H, t, J = 6.5 Hz), 1.23-
1.35 (6H, m), 1.35-1.50 (2H, m), 2.38-2.55 (6H,
m) 2.86 (4H, t, 6.8 Hz)

(2) Synthesis of N, N-bis (3-aminopropyl) hexylamine 31.0 g of N, N-bis (2-cyanoethyl) hexylamine, Ran
charged with 4.65 g of eyCo and 150 ml of 1,4-dioxane, and hydrogen initial pressure of 9.1 MPa
The hydrogenation reaction was performed at 110 ° C. for 2 hours. After removing the catalyst by filtration, the obtained filtrate was concentrated under reduced pressure to give 32.4 g of the title compound as a pale red oil.

¹ H NMR (CDCl ₃ ): δ = 0.88 (3H, t, J = 6.6 Hz), 1.26
-1.34 (6H, m), 1.34-1.50 (2H, m), 1.50-1.69 (4H
M), 2.35-2.47 (6H, m), 2.67-2.79 (4H, m)
GC-MS (m / z): 215.

(3) Synthesis of compound represented by formula (8) N, N-bis (3-aminopropyl) hexylamine 21.5 g, 2-chloro-4,6
-Bis (N- (2,2,6,6-tetramethylpiperidin-4-yl) butylamino)-
1,3-dimethyl-2 of 105.6 g of 1,3,5-triazine and 30.4 g of potassium carbonate
A solution of 1000 ml of imidazolidinone (DMI) was stirred at 100 ° C. for 14 hours. Further, 3.2 g of N, N-bis (3-aminopropyl) hexylamine was added to the solution.
For 11 hours. After allowing to cool to room temperature, 500 ml of water was added, and the mixture was extracted with 700 ml of ethyl acetate. The organic layer obtained by liquid separation was washed twice with 500 ml of water and once with 30 ml of saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the concentrated residue was purified by silica gel column chromatography to obtain 57.0 g of the title compound as a white solid.

¹ H NMR (CDCl ₃ ): δ = 0.84-0.94 (15H, m), 1.05-1
. 28 (70H, m), 1.28-1.73 (22H, m), 2.35 (2H, t, J =
7.6 Hz), 2.46 (4H, t, J = 6.4 Hz), 3.29-3.41 (12H,
m), 5.15 (4H, br)
MS (FD, m / z): 1214.
Melting point: 72 ° C.

(Example 2)
Production of compound represented by formula (9)

(1) Synthesis of N, N-bis (2-cyanoethyl) dodecylamine To an ethanol solution (150 ml) of 1-aminododecane 27.8 g, acrylonitrile 39.8 g was added dropwise at room temperature over 0.5 hours, and then 22.5 g of acetic acid was added dropwise over 0.5 hours, and the mixture was stirred at 77 ° C. for 10 hours. After allowing to cool to room temperature, 150 ml of water and 22.8 g of 28% aqueous ammonia were added, and the mixture was extracted with 330 ml of ethyl acetate. The organic layer obtained by liquid separation was washed twice with 100 ml of water and 50 ml of saturated brine. Dried over anhydrous magnesium sulfate,
After distilling off the solvent, the concentrated residue was purified by silica gel column chromatography to obtain 39.7 g of the title compound as a white solid.

¹ H NMR (CDCl ₃ ): δ = 0.90 (3H, t, J = 6.5 Hz), 1.21
-1.32 (18H, m), 1.32-1.51 (2H, m), 2.52-2.59 (6
H, m), 2.82 (4H, t, 6.5 Hz)
(2) Synthesis of N, N-bis (3-aminopropyl) dodecylamine In an autoclave, 19.7 g of N, N-bis (2-cyanoethyl) dodecylamine, Ra
1.97 g of neyCo and 80 ml of 1,4-dioxane were charged, and the initial hydrogen pressure was 8.2 MPa.
The hydrogenation reaction was performed at 120 ° C. for 2 hours. After removing the catalyst by filtration, the obtained filtrate was concentrated under reduced pressure to obtain 21.0 g of the title compound as a pale red oil. This operation was repeated once to obtain a total of 40.8 g of the title compound as a pale red oil.

¹ H NMR (CDCl ₃ ): δ = 0.88 (3H, t, J = 6.5 Hz), 1.26
-1.37 (18H, m), 1.37-1.47 (2H, m), 1.53-1.68 (4
H, m), 2.35-2.47 (6H, m), 2.72-2.85 (4H, m)
GC-MS (m / z): 299.

(3) Synthesis of compound represented by formula (9) N, N-bis (3-aminopropyl) dodecylamine 30.0 g, 2-chloro-4,6
-Bis (N- (2,2,6,6-tetramethylpiperidin-4-yl) butylamino)-
1,3,5-triazine 107.7 g, potassium carbonate 30.4 g 1,3-dimethyl-2
A solution of 700 ml of imidazolidinone (DMI) was stirred at 100 ° C. for 16 hours. After allowing to cool to room temperature, 500 ml of water was added, and the mixture was extracted with 700 ml of ethyl acetate. The organic layer obtained by liquid separation was washed twice with 500 ml of water and once with 50 ml of saturated brine, and dried over anhydrous magnesium sulfate. After evaporating the solvent, the concentrated residue was purified by silica gel column chromatography to obtain 60.7 g of the title compound as a white solid.

¹ H NMR (CDCl ₃ ): δ = 0.83-0.89 (15H, m), 1.11-1
. 25 (82H, m), 1.25-1.69 (22H, m), 2.32 (2H, t, J =
7.6 Hz), 2.43 (4H, t, J = 6.4 Hz), 3.27-3.37 (12H,
m), 5.24 (4H, br)
MS (FD, m / z): 1298.
Melting point: 60 ° C.

(Example 3)
Production of compound represented by formula (10)

(1) Synthesis of N, N-bis (2-cyanoethyl) octadecylamine 40.2 g of acrylonitrile at room temperature was added dropwise to an ethanol solution (150 ml) of 41.7 g of stearylamine over 0.5 hour, and then acetic acid 22 0.5 g was added dropwise over 0.5 hours and stirred at 77 ° C. for 10 hours. After cooling to room temperature, 200 ml of water and 22.8 g of 28% aqueous ammonia were added, and the mixture was extracted with 500 ml of ethyl acetate. The organic layer obtained by liquid separation was washed with 100 ml of water and 50 ml of saturated brine. After drying over anhydrous magnesium sulfate and distilling off the solvent, the concentrated residue is recrystallized using isopropyl alcohol as a solvent to give the title compound 42.
4 g was obtained as a white solid.

¹ H NMR (CDCl ₃ ): δ = 0.88 (3H, t, J = 6.6 Hz), 1.20
-1.38 (30H, m), 1.38-1.47 (2H, m), 2.43-2.55 (6
H, m), 2.86 (4H, t, 6.9 Hz)

(2) Synthesis of N, N-bis (3-aminopropyl) octadecylamine 42.1 g of N, N-bis (2-cyanoethyl) octadecylamine in an autoclave,
RaneyCo 3.26g, 1,4-dioxane 150ml was charged, hydrogen initial pressure 8.0
Hydrogenation reaction was performed at 110 ° C. for 2 hours. After removing the catalyst by filtration, the obtained filtrate was concentrated under reduced pressure to obtain 42.3 g of the title compound as a white solid.

¹ H NMR (CDCl ₃ ): δ = 0.88 (3H, t, J = 6.6 Hz), 1.26
-1.36 (30H, m), 1.36-1.47 (2H, m), 1.53-1.66 (4
H, m), 2.35-2.50 (6H, m), 2.72-2.79 (4H, m)
GC-MS (m / z): 383.
(3) Synthesis of compound represented by formula (10) N, N-bis (3-aminopropyl) octadecylamine 38.4 g, 2-chloro-4
, 6-Bis (N- (2,2,6,6-tetramethylpiperidin-4-yl) butylamino) -1,3,5-triazine 107.7 g, potassium carbonate 30.4 g 1,3-dimethyl A solution of 900 ml of 2-imidazolidinone (DMI) was stirred at 100 ° C. for 16 hours. Further, 1.5 g of N, N-bis (3-aminopropyl) octadecylamine was added to the solution.
The mixture was stirred at 00 ° C. for 11.5 hours. After cooling to room temperature, 500 ml of water was added, and ethyl acetate 7
Extracted with 00 ml. The organic layer obtained by liquid separation was washed twice with 500 ml of water and saturated brine 50
The extract was washed once with ml and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the concentrated residue was purified by silica gel column chromatography to obtain 74.2 g of the title compound as a white solid.

¹ H NMR (CDCl ₃ ): δ = 0.85-0.94 (15H, m), 1.05-1
. 33 (94H, m), 1.33-1.73 (22H, m), 2.35 (2H, t, J =
7.3 Hz), 2.46 (4H, t, J = 6.4 Hz), 3.29-3.43 (12H,
m), 5.26 (4H, br)
MS (FD, m / z): 1382.
Melting point: 46 ° C.

Ｎ，Ｎ−ビス（３−アミノプロピル）ブチルアミン１２．４ｇ、２−クロロ−４，６−ビス（Ｎ−（２，２，６，６−テトラメチルピペリジン−４−イル）ブチルアミノ）−１，３，５−トリアジン６４．４ｇ、炭酸カリウム１０．０ｇのＮ，Ｎ−ジメチルホルムアミド（ＤＭＦ）１５０ｍｌ溶液を１２０℃で８時間攪拌した。室温まで放冷後に水４５０ｍｌを加え、酢酸エチル６００ｍｌで抽出した。分液により得られた有機層を水４５０ｍｌで２回、飽和食塩水３０ｍｌで１回洗浄し、無水硫酸マグネシウムで乾燥した。溶媒を留去後、濃縮残渣をシリカゲルカラムクロマトグラフィーにより精製し、標題化合物６２．１ｇを白色固体として得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）：δ＝０．８０−０．９４（１５Ｈ、ｍ）、１．１２（２４Ｈ、ｓ）、１．２７（２４Ｈ、ｓ）、１．１６−１．７８（３６Ｈ、ｍ）、１．７０（４Ｈ、ｔ、Ｊ＝６．６Ｈｚ）、２．２９−２．４０（２Ｈ、ｍ）、２．４５（４Ｈ、ｔ、Ｊ＝６．６Ｈｚ）、３．１６−３．３８（８Ｈ、ｍ）、３．３９（４Ｈ、ｄｄ、Ｊ＝５．９、１１．９Ｈｚ）、５．０６−５．４０（４Ｈ、ｍ）
ＭＳ（ＦＤ，ｍ／ｚ）：１１８６．
融点：７８℃． Example 4
Production of compound represented by formula (11)

12.4 g of N, N-bis (3-aminopropyl) butylamine, 2-chloro-4,6-bis (N- (2,2,6,6-tetramethylpiperidin-4-yl) butylamino) -1 , 3,5-triazine and 10.0 ml of potassium carbonate in 150 ml of N, N-dimethylformamide (DMF) were stirred at 120 ° C. for 8 hours. After cooling to room temperature, 450 ml of water was added, and the mixture was extracted with 600 ml of ethyl acetate. The organic layer obtained by liquid separation was washed twice with 450 ml of water and once with 30 ml of saturated brine, and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the concentrated residue was purified by silica gel column chromatography to obtain 62.1 g of the title compound as a white solid.
¹ H NMR (CDCl ₃ ): δ = 0.80-0.94 (15H, m), 1.12 (24H, s), 1.27 (24H, s), 1.16-1.78 (36H) M) 1.70 (4H, t, J = 6.6 Hz), 2.29-2.40 (2H, m), 2.45 (4H, t, J = 6.6 Hz), 3.16 −3.38 (8H, m), 3.39 (4H, dd, J = 5.9, 11.9 Hz), 5.06 to 5.40 (4H, m)
MS (FD, m / z): 1186.
Melting point: 78 ° C.

（１）Ｎ，Ｎ−ビス（２−シアノエチル）シクロヘキサンメチルアミンの合成
シクロヘキサンメチルアミン２２．０ｇのエタノール溶液（１００ｍｌ）に、室温下アクリロニトリル３０．０ｇを０．５時間かけて滴下し、その後７５℃で５時間撹拌した。室温まで放冷後、酢酸エチル１５０ｍｌを加えて抽出した。分液により得た有機層を無水硫酸マグネシウムにて乾燥した後、溶媒を留去して標題化合物４７．７ｇを無色油状物として得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）：δ＝０．７３−０．９２（１２Ｈ、ｍ）、１．１０−１．３２（３Ｈ、ｍ）、１．５８−１．８８（６Ｈ、ｍ）、２．２８（２Ｈ、ｄ、Ｊ＝７．３Ｈｚ）、２．４４（４Ｈ、ｔ、Ｊ＝６．９Ｈｚ）、２．８２（４Ｈ、ｄ、Ｊ＝６．９Ｈｚ）
（２）Ｎ，Ｎ−ビス（３−アミノプロピル）シクロヘキサンメチルアミンの合成
オートクレーブにＮ，Ｎ−ビス（２−シアノエチル）シクロヘキサンメチルアミン４７．７ｇ、ＲａｎｅｙＣｏ２．３５ｇ、１，４−ジオキサン１００ｍｌを装入し、水素初気圧９．３ＭＰａ、１２０℃で１時間水素添加反応を行った。触媒を濾去後、得られた濾液を減圧濃縮することにより、標題化合物４５．５ｇを淡赤色油状物として得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）：δ＝０．６７−０．８８（２Ｈ、ｍ）、１．０２−１．３６（３Ｈ、ｍ）、１．３６−１．７７（１０Ｈ、ｍ）、２．０６（２Ｈ、ｄ、Ｊ＝６．９Ｈｚ）、２．３４（４Ｈ、ｔ、Ｊ＝６．９Ｈｚ）、２．６６（４Ｈ、ｄ、Ｊ＝６．９Ｈｚ）
（３）式（１２）で表される化合物の合成
Ｎ，Ｎ−ビス（３−アミノプロピル）シクロヘキサンメチルアミン３０．９ｇ、２−クロロ−４，６−ビス（Ｎ−（２，２，６，６−テトラメチルピペリジン−４−イル）ブチルアミノ）−１，３，５−トリアジン１２９．０ｇ、炭酸カリウム８０．４ｇの１，３−ジメチル−２−イミダゾリジノン（ＤＭＩ）５００ｍｌ溶液を１００℃で１４時間攪拌した。室温まで放冷後に水５００ｍｌを加え、酢酸エチル７００ｍｌで抽出した。分液により得られた有機層を水５００ｍｌで２回、飽和食塩水３０ｍｌで１回洗浄し、無水硫酸マグネシウムで乾燥した。溶媒を留去後、濃縮残渣をシリカゲルカラムクロマトグラフィーにより精製し、標題化合物６２．３gを白色固体として得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）：δ＝０．９１（１２Ｈ、ｔ、Ｊ＝６．９Ｈｚ）、１．１３（２４Ｈ、ｓ）、１．２７（２４Ｈ、ｓ）、１．１０−１．８８（４７Ｈ、ｍ）、２．１１（２Ｈ、ｄ、Ｊ＝６．６Ｈｚ）、２．４１（４Ｈ、ｔ、Ｊ＝６．６Ｈｚ）、３．１８−３．４０（８Ｈ、ｍ）、３．３８（４Ｈ、ｄｄ、Ｊ＝６．６、１２．５Ｈｚ）、５．００−５．３５（４Ｈ、ｍ）ＭＳ（ＦＤ，ｍ／ｚ）：１２２６．融点：７７℃． (Example 5)
Production of compound represented by formula (12)

(1) Synthesis of N, N-bis (2-cyanoethyl) cyclohexanemethylamine
To an ethanol solution (100 ml) of 22.0 g of cyclohexanemethylamine, 30.0 g of acrylonitrile was added dropwise at room temperature over 0.5 hours, and then stirred at 75 ° C. for 5 hours. After cooling to room temperature, 150 ml of ethyl acetate was added for extraction. The organic layer obtained by liquid separation was dried over anhydrous magnesium sulfate, and then the solvent was distilled off to obtain 47.7 g of the title compound as a colorless oil.
¹ H NMR (CDCl ₃ ): δ = 0.73-0.92 (12H, m), 1.10-1.32 (3H, m), 1.58-1.88 (6H, m), 2 .28 (2H, d, J = 7.3 Hz), 2.44 (4H, t, J = 6.9 Hz), 2.82 (4H, d, J = 6.9 Hz)
(2) Synthesis of N, N-bis (3-aminopropyl) cyclohexanemethylamine An autoclave was charged with 47.7 g of N, N-bis (2-cyanoethyl) cyclohexanemethylamine, 2.35 g of RaneyCo, and 100 ml of 1,4-dioxane. The hydrogenation reaction was performed at 120 ° C. for 1 hour at an initial hydrogen pressure of 9.3 MPa. After removing the catalyst by filtration, the obtained filtrate was concentrated under reduced pressure to obtain 45.5 g of the title compound as a pale red oil.
¹ H NMR (CDCl ₃ ): δ = 0.67-0.88 (2H, m), 1.02-1.36 (3H, m), 1.36-1.77 (10H, m), 2 .06 (2H, d, J = 6.9 Hz), 2.34 (4H, t, J = 6.9 Hz), 2.66 (4H, d, J = 6.9 Hz)
(3) Synthesis of Compound Represented by Formula (12) 30.9 g of N, N-bis (3-aminopropyl) cyclohexanemethylamine, 2-chloro-4,6-bis (N- (2,2,6) , 6-Tetramethylpiperidin-4-yl) butylamino) -1,3,5-triazine 129.0 g, potassium carbonate 80.4 g in 1,3-dimethyl-2-imidazolidinone (DMI) 500 ml Stir at 14 ° C. for 14 hours. After cooling to room temperature, 500 ml of water was added, and the mixture was extracted with 700 ml of ethyl acetate. The organic layer obtained by liquid separation was washed twice with 500 ml of water and once with 30 ml of saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the concentrated residue was purified by silica gel column chromatography to obtain 62.3 g of the title compound as a white solid.
¹ H NMR (CDCl ₃ ): δ = 0.91 (12H, t, J = 6.9 Hz), 1.13 (24H, s), 1.27 (24H, s), 1.10-1.88 (47H, m), 2.11 (2H, d, J = 6.6 Hz), 2.41 (4H, t, J = 6.6 Hz), 3.18-3.40 (8H, m), 3 .38 (4H, dd, J = 6.6, 12.5 Hz), 5.00-5.35 (4H, m) MS (FD, m / z): 1226. Melting point: 77 ° C.

Ｎ，Ｎ−ビス（３−アミノプロピル）ブチルアミン８．４４ｇ、２−クロロ−４，６−ビス（Ｎ−（１，２，２，６，６−ペンタメチルピペリジン−４−イル）ブチルアミノ）−１，３，５−トリアジン５０．８ｇ、炭酸カリウム１２．４ｇのＮ，Ｎ−ジメチルホルムアミド（ＤＭＦ）１００ｍｌ溶液を１２０℃で７時間攪拌した。室温まで放冷後に水４００ｍｌを加え、酢酸エチル５００ｍｌで抽出した。分液により得られた有機層を水４００ｍｌで２回、飽和食塩水３０ｍｌで１回洗浄し、無水硫酸マグネシウムで乾燥した。溶媒を留去後、濃縮残渣をシリカゲルカラムクロマトグラフィーにより精製し、標題化合物３５．４ｇを白色固体として得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）：δ＝０．８２−０．９６（１５Ｈ、ｍ）、１．０９（２４Ｈ、ｓ）、１．１５（２４Ｈ、ｓ）、１．１６−１．７０（３６Ｈ、ｍ）、１．７０（４Ｈ、ｔ、Ｊ＝６．６Ｈｚ）、２．２４（１２Ｈ、ｓ）、２．３１−２．４０（２Ｈ、ｍ）、２．４５（４Ｈ、ｔ、Ｊ＝６．６Ｈｚ）、３．１８−３．３８（８Ｈ、ｍ）、３．３８（４Ｈ、ｄｄ、Ｊ＝６．６、１２．５Ｈｚ）、４．９５−５．３５（４Ｈ、ｍ）
ＭＳ（ＦＤ，ｍ／ｚ）：１２４２．融点：８６℃． (Example 6)
Production of compound represented by formula (13)

N, N-bis (3-aminopropyl) butylamine 8.44 g, 2-chloro-4,6-bis (N- (1,2,2,6,6-pentamethylpiperidin-4-yl) butylamino) A solution of 50.8 g of -1,3,5-triazine and 12.4 g of potassium carbonate in 100 ml of N, N-dimethylformamide (DMF) was stirred at 120 ° C. for 7 hours. After allowing to cool to room temperature, 400 ml of water was added, and the mixture was extracted with 500 ml of ethyl acetate. The organic layer obtained by liquid separation was washed twice with 400 ml of water and once with 30 ml of saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the concentrated residue was purified by silica gel column chromatography to obtain 35.4 g of the title compound as a white solid.
¹ H NMR (CDCl ₃ ): δ = 0.82-0.96 (15H, m), 1.09 (24H, s), 1.15 (24H, s), 1.16-1.70 (36H) M) 1.70 (4H, t, J = 6.6 Hz), 2.24 (12H, s), 2.31-2.40 (2H, m), 2.45 (4H, t, J = 6.6 Hz), 3.18-3.38 (8H, m), 3.38 (4H, dd, J = 6.6, 12.5 Hz), 4.95-5.35 (4H, m)
MS (FD, m / z): 1242. Melting point: 86 ° C.

Ｎ，Ｎ−ビス（３−アミノプロピル）ヘキシルメチルアミン２８．８ｇ、２−クロロ−４，６−ビス（Ｎ−（１，２，２，６，６−ペンタメチルピペリジン−４−イル）ブチルアミノ）−１，３，５−トリアジン１２０．１ｇ、炭酸カリウム７６．５ｇの１，３−ジメチル−２−イミダゾリジノン（ＤＭＩ）５００ｍｌ溶液を１００℃で１２時間攪拌した。室温まで放冷後に水５００ｍｌを加え、酢酸エチル７００ｍｌで抽出した。分液により得られた有機層を水５００ｍｌで２回、飽和食塩水３０ｍｌで１回洗浄し、無水硫酸マグネシウムで乾燥した。溶媒を留去後、濃縮残渣をシリカゲルカラムクロマトグラフィーにより精製し、標題化合物６８．４gを白色固体として得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）：δ＝０．７８−０．９６（１５Ｈ、ｍ）、１．０９（２４Ｈ、ｓ）、１．１５（２４Ｈ、ｓ）、１．１０−１．７６（４０Ｈ、ｍ）、１．７０（４Ｈ、ｔ、Ｊ＝６．６Ｈｚ）、２．２４（１２Ｈ、ｓ）、２．２８−２．４０（２Ｈ、ｍ）、２．４５（４Ｈ、ｔ、Ｊ＝６．６Ｈｚ）、３．２０−３．４０（８Ｈ、ｍ）、３．３８（４Ｈ、ｄｄ、Ｊ＝６．６、１２．５Ｈｚ）、５．００−５．２８（４Ｈ、ｍ）
ＭＳ（ＦＤ，ｍ／ｚ）：１２７０．融点：８１℃． (Example 7)
Production of synthesis of compound represented by formula (14)

28.8 g of N, N-bis (3-aminopropyl) hexylmethylamine, 2-chloro-4,6-bis (N- (1,2,2,6,6-pentamethylpiperidin-4-yl) butyl A solution of 120.1 g of amino) -1,3,5-triazine and 76.5 g of potassium carbonate in 500 ml of 1,3-dimethyl-2-imidazolidinone (DMI) was stirred at 100 ° C. for 12 hours. After cooling to room temperature, 500 ml of water was added, and the mixture was extracted with 700 ml of ethyl acetate. The organic layer obtained by liquid separation was washed twice with 500 ml of water and once with 30 ml of saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the concentrated residue was purified by silica gel column chromatography to obtain 68.4 g of the title compound as a white solid.
¹ H NMR (CDCl ₃ ): δ = 0.78-0.96 (15H, m), 1.09 (24H, s), 1.15 (24H, s), 1.10-1.76 (40H) M), 1.70 (4H, t, J = 6.6 Hz), 2.24 (12H, s), 2.28-2.40 (2H, m), 2.45 (4H, t, J = 6.6 Hz), 3.20-3.40 (8 H, m), 3.38 (4 H, dd, J = 6.6, 12.5 Hz), 5.00-5.28 (4 H, m)
MS (FD, m / z): 1270. Melting point: 81 ° C.

Ｎ，Ｎ−ビス（３−アミノプロピル）ドデシルアミン１２．２ｇ、２−クロロ−４，６−ビス（Ｎ−（１，２，２，６，６−ペンタメチルピペリジン−４−イル）ブチルアミノ）−１，３，５−トリアジン４５．１ｇ、炭酸カリウム１１．１ｇのＮ，Ｎ−ジメチルホルムアミド（ＤＭＦ）１００ｍｌ溶液を１２０℃で７時間攪拌した。室温まで放冷後に水３５０ｍｌを加え、酢酸エチル４００ｍｌで抽出した。分液により得られた有機層を水３５０ｍｌで２回、飽和食塩水３０ｍｌで１回洗浄し、無水硫酸マグネシウムで乾燥した。溶媒を留去後、濃縮残渣をシリカゲルカラムクロマトグラフィーにより精製し、標題化合物２３．３ｇを白色固体として得た。
^１Ｈ ＮＭＲ（ＣＤＣｌ_３）：δ＝０．８０−０．９６（１５Ｈ、ｍ）、１．０９（２４Ｈ、ｓ）、１．１５（２４Ｈ、ｓ）、１．１０−１．７０（５２Ｈ、ｍ）、１．７０（４Ｈ、ｔ、Ｊ＝６．６Ｈｚ）、２．２４（１２Ｈ、ｓ）、２．２９−２．３９（２Ｈ、ｍ）、２．４５（４Ｈ、ｔ、Ｊ＝６．６Ｈｚ）、３．１８−３．４０（８Ｈ、ｍ）、３．３８（４Ｈ、ｄｄ、Ｊ＝６．６、１２．５Ｈｚ）、５．００−５．３２（４Ｈ、ｍ）
ＭＳ（ＦＤ，ｍ／ｚ）：１３５４． 融点：６７℃． (Example 8)
Production of compound represented by formula (15)

N, N-bis (3-aminopropyl) dodecylamine 12.2 g, 2-chloro-4,6-bis (N- (1,2,2,6,6-pentamethylpiperidin-4-yl) butylamino ) A solution of 45.1 g of 1,3,5-triazine and 11.1 g of potassium carbonate in 100 ml of N, N-dimethylformamide (DMF) was stirred at 120 ° C. for 7 hours. After cooling to room temperature, 350 ml of water was added, and the mixture was extracted with 400 ml of ethyl acetate. The organic layer obtained by liquid separation was washed twice with 350 ml of water and once with 30 ml of saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the concentrated residue was purified by silica gel column chromatography to obtain 23.3 g of the title compound as a white solid.
¹ H NMR (CDCl ₃ ): δ = 0.80-0.96 (15H, m), 1.09 (24H, s), 1.15 (24H, s), 1.10-1.70 (52H) M), 1.70 (4H, t, J = 6.6 Hz), 2.24 (12H, s), 2.29-2.39 (2H, m), 2.45 (4H, t, J = 6.6 Hz), 3.18-3.40 (8H, m), 3.38 (4H, dd, J = 6.6, 12.5 Hz), 5.00-5.32 (4H, m)
MS (FD, m / z): 1354. Melting point: 67 ° C.

(Comparative Example 1)
Production of compound represented by formula (16)

14.5 g of N, N-bis (3-aminopropyl) methylamine, 2-chloro-4,6-
Bis (N- (2,2,6,6-tetramethylpiperidin-4-yl) butylamino) -1
, 3,5-triazine 105.1 g, potassium carbonate 30.4 g 1,3-dimethyl-2-
A 600 ml solution of imidazolidinone (DMI) was stirred at 100 ° C. for 17 hours. N,
Add 1.7 g of N-bis (3-aminopropyl) methylamine to the solution and add 12 at 100 ° C.
Stir for hours. After allowing to cool to room temperature, 500 ml of water was added, and the mixture was extracted with 700 ml of ethyl acetate. The organic layer obtained by liquid separation was washed twice with 500 ml of water and once with 50 ml of saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the concentrated residue was purified by silica gel column chromatography to obtain 75.2 g of the title compound as a white solid.

¹ H NMR (CDCl ₃ ): δ = 0.89-0.98 (12H, m), 1.05-1
. 43 (62H, m), 1.43-1.76 (22H, m), 2.19 (3H, s), 2
. 40 (4H, t, J = 6.8 Hz), 3.30-3.44 (12H, m), 5.18 (
4H, br) MS (FD, m / z): 1144. Melting point: 85 ° C.

(Examples 9 to 13)
Next, the Example in the case of using as a polypropylene resin composition is shown.

Raw materials The additives used in the production of the resin composition are as follows.
◇ Heat resistant stabilizer (additive A) Tris (2,4-di-t-butylphenyl) phosphite Ciba Geigy Co., Ltd., Irgafos 168
(Additive B) Tetrakis [methylene-3 (3,5-di-t-butyl-4-hydroxyphenyl) propionate] Methane Ciba Geigy Co., Ltd., Irganox 1010
◇ Dispersant (Additive C) Calcium stearate made by Sakai Chemical Industry Co., Ltd.
Light stabilizer (additive D) bis (2,2 ′, 6,6′-tetramethyl-4-piperidyl) sebacate. Made by Ciba Geigy. Product name TINUVIN770.
(Additive E) Compound obtained in Comparative Example 1.
(Additive F) Compound obtained in Example 1.
(Additive G) Compound obtained in Example 2.
(Additive H) Compound obtained in Example 3.
(Additive K) The compound obtained in Example 4.
(Additive M) Compound obtained in Example 6.

Production of resin composition 65 parts by weight of a crystalline propylene / ethylene block copolymer (ethylene content = 3 wt%, MFR = 50 (g / 10 min)) is used as an olefin-based elastomer. -15 parts by weight of octene copolymer (1-octene content: 7.3 mol%, MFR (190 ° C) = 5 (g / 10 min)), talc (manufactured by Fuji Talc Kogyo Co., Ltd., trade name K-1) The average particle size 2 μm) is added to 20 parts by weight of the raw material, the raw materials listed in Table 1 are mixed in a predetermined amount in a tumbler mixer, and then melt-kneaded using a twin-screw kneading extruder to obtain a resin composition A pellet consisting of

The physical property measuring method MFR of the resin composition was measured under a load of 2.16 kg according to ASTM D1238.

Evaluation method of resin composition The light resistance of the resin composition obtained by the above method was evaluated by the following method.
◇ Light resistance evaluation The resin composition was supplied to an injection molding machine (AN100 manufactured by Niigata Iron Works), and a flat plate (120 mm × 130 mm × 3 mmt) was molded to obtain a test piece for a light resistance test. The light resistance test was conducted using a Suga Test Instruments Co., Ltd. product (FAL-5H-B type UV fade meter) under a black panel temperature of 83 ° C. and no rain. The case where surface cracks did not occur even after 1000 hours was judged as good (◯), and the case where surface cracks occurred within 1000 hours was judged as poor (x).

Evaluation results of resin composition Table 2 shows the evaluation results of light resistance.

(Examples 14 to 20)
Next, the Example in the case of using as a norbornene-type resin composition is shown.
Raw materials The additives used in the production of the resin composition are as follows.
Light stabilizer (additive D) bis (2,2 ′, 6,6′-tetramethyl-4-piperidyl) sebacate. Made by Ciba Geigy. Product name TINUVIN770.
(Additive E) Compound obtained in Comparative Example 1.
(Additive F) Compound obtained in Example 1.
(Additive G) Compound obtained in Example 2.
(Additive H) Compound obtained in Example 3.
(Additive L) Compound obtained in Example 5.
(Additive N) Compound obtained in Example 7.
(Additive P) Compound obtained in Example 8.
◇ Phosphorus stabilizer (additive J) 6- [3- (3-t-butyl-4-hydroxy-5-methylphenyl) propoxy] -2,4,8,10-tetrakis-t-butyldibenzo [d , F] [1.3.2] dioxaphosphine. Made by Sumitomo Chemical Co., Ltd. Product name Sumilyzer GP.

Production of resin composition An ethylene-tetracyclo [4.4.0.12,5.17,10] dodecene-3 copolymer was polymerized using a Ziegler catalyst. Cyclic olefin random copolymer which was flash-dried by the method described in Example of JP-A-3-220211 after adding one kind of additive (1) shown in Table 1 to the cyclohexane solution of this polymer as required This was directly charged into the extruder in the molten state.
A biaxial kneading extruder with a vent is used as the extruder, and the cyclic olefin random copolymer obtained by the above method is charged from the resin charging part and then trapped for the purpose of removing volatiles from the vent part. Then, one kind of additive (1) shown in Table 1 was added from the downstream part of the vent part while sucking with a vacuum pump, and kneaded and mixed in the latter half of the extruder.
Pellets were obtained with an underwater pelletizer attached to the exit of the extruder and dried with hot air at 100 ° C. for 4 hours.
Table 3 shows the additives used as the additives (1) and (2) and the physical properties of the obtained resin composition.

Method for measuring physical properties of resin composition The physical properties shown in Table 3 were measured by the following methods.
◇ Melting flow index (MFR)
Measured with a load of 2.16 kg according to ASTM D1238. The measurement temperature was 260 ° C.
◇ Softening temperature (TMA)
Using a Thermal Mechanical Analyzer manufactured by DuPont, the thermal deformation behavior of a sheet having a thickness of 1 mm was measured. A quartz needle was placed on the sheet, a load of 49 g was applied, the temperature was raised at a rate of 5 ° C./min, and the temperature at which the needle penetrated into the sheet by 0.635 mm was defined as TMA.

Evaluation method of resin composition The evaluation method is as follows.
◇ Haze
The resin composition was supplied to an injection molding machine (AN100 manufactured by Niigata Iron Works), a flat plate (120 mm × 130 mm × 3 mmt) was molded, and measured based on ASTM D1003.
◇ Blue-violet laser reliability evaluation 45mmφ × 3mm (thickness) optical injection molded by injection molding machine (IS-50 manufactured by Toshiba Machine Co., Ltd.) set at 260 ° C cylinder temperature and 125 ° C mold temperature A test piece having a surface is used, and a laser diode (TC4030S-F405ASU manufactured by Neoarc) is used, and a blue-violet laser beam of 405 ± 10 nm, 200 mW / cm ² is placed in the center of the test piece at 1000 ° C. Irradiated for hours. The wavefront RMS value of the center 3 mmφ of the test piece was measured before irradiation and every 250 hours of irradiation, and the change with time was evaluated. The measurement of the RMS value was performed using a laser interferometer (PTI 250RS (linear polarization specification) manufactured by Zygo Corporation). Moreover, the test piece irradiation site | part was observed with the stereoscopic microscope, and the presence or absence of white turbidity and a foreign material adhesion was confirmed. The results are represented by the following symbols.
○: No change in RMS value
Δ: RMS value change rate was observed at less than 0.01λ.
X: RMS value is changed by 0.01λ or more. Or it became impossible to measure.
◆: The cloudiness was remarkably observed.

Evaluation results of resin composition Table 4 shows the evaluation results of optical properties (haze) and blue-violet laser reliability.

The compounds of the present invention are effective for stabilizing polyolefins against deterioration by light, heat and oxygen.

Claims (9)

General formula (1):

(Wherein X and Y may be the same or different and each represents N (R ⁵ ) or an oxygen atom;
R ¹ is a hydrocarbon group having 2 to 50 carbon atoms selected from a linear, branched, or substituted or unsubstituted cyclic alkyl group, and contains an oxygen atom or a nitrogen atom in the middle of the carbon chain. R ² represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, R ³ and R ⁴ may be the same or different, and a hydrogen atom, an alkyl group having 1 to 9 carbon atoms, 9 represents an alkoxy group having 9 carbon atoms or an acyl group having 2 to 9 carbon atoms, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, and n represents an integer of 2 or 3. Or a salt thereof. General formula (1):

(Wherein X and Y may be the same or different and each represents N (R ⁵ ) or an oxygen atom;
R ¹ is a hydrocarbon group having 2 to 50 carbon atoms selected from a linear or branched alkyl group, may contain an oxygen atom or a nitrogen atom in the middle of the carbon chain, and R ² is hydrogen Represents an atom or an alkyl group having 1 to 9 carbon atoms, and R ³ and R ⁴ may be the same or different, and are a hydrogen atom, an alkyl group having 1 to 9 carbon atoms, an alkoxy group having 1 to 9 carbon atoms or a carbon number; R 2 represents an acyl group having 2 to 9, R ⁵ represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, and n represents an integer of 2 or 3. Or a salt thereof. The compound or a salt thereof according to claim 1 or 2, wherein, in the general formula (1), X and Y are N (R ⁵ ) and n is 3. The compound or a salt thereof according to claim 3, wherein, in the general formula (1), R ¹ is a hydrocarbon group having 4 to 35 carbon atoms. The compound or salt thereof according to claim 4, wherein, in the general formula (1), R ¹ is a linear or branched alkyl group having 4 to 35 carbon atoms. The compound or a salt thereof according to claim 5, wherein, in the general formula (1), R ¹ is a linear or branched alkyl group having 4 to 18 carbon atoms. General formula (2):

(In the formula, X, Y, R ³ and R ⁴ are the same as those described in the general formula (1), and Z represents a halogen atom.)
A compound represented by formula (3):

(In the formula, R ¹ is a hydrocarbon group having 2 to 50 carbon atoms selected from a linear, branched, or substituted or unsubstituted cyclic alkyl group, and an oxygen atom or a nitrogen atom is inserted in the middle of the carbon chain. R ² represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, n represents an integer of 2 or 3, and is coupled with a compound represented by The manufacturing method of the compound represented by General formula (1) of Claim 1 or Claim 2.   The stabilizer for polyolefin containing at least 1 among the compounds or its salt represented by General formula (1) of Claim 1 or Claim 2. A polyolefin resin composition comprising 0.001 to 15 parts by weight of the compound represented by the general formula (1) according to claim 1 or 2 or a salt thereof with respect to 100 parts by weight of the polyolefin.