JP2023147016A - Hindered amine compound and composition - Google Patents

Abstract

To provide a novel hindered amine compound which is useful as a HALS, has excellent compatibility with polyolefin, and does not volatilize or run off, and a composition containing the hindered amine compound.SOLUTION: The invention provides a hindered amine compound represented by general formula (I) in the figure. (R1 and R2 are each independently a C3-8 alkyl group or a C6-8 aryl group; X is O (oxygen atom), CH2, S (sulfur atom), or NH; R3 is a hydrogen atom, a C1-3 alkyl group, a C1-11 alkoxy group, or a COR4 group; R4 is a C1-4 alkyl group; and Me is a methyl group.)SELECTED DRAWING: None

Description

The present invention relates to hindered amine compounds and compositions containing hindered amine compounds.

Polyolefin resins, represented by polyethylene and polypropylene, are inexpensive and have excellent advantages such as moldability, heat resistance, chemical resistance, mechanical properties, and low specific gravity, and are used for injection molding, extrusion molding, film molding, etc. It is subjected to various molding processes, and its molded products are widely used in various fields. Furthermore, when used, a stabilizer such as an antioxidant is generally added. For example, in the case of outdoor use, weather resistance becomes a problem, so hindered amine light stabilizers (hereinafter referred to as "HALS") are generally blended into the resin.

In recent years, there has been a demand for further improvement in the weather resistance of polyolefins from the viewpoint of material recycling. One of the causes of reduced weather resistance of molded products containing HALS is bleeding of HALS onto the surface, runoff from the surface due to rain, etc., and volatilization. Therefore, a general method for improving the performance of HALS is to increase the molecular weight.

For example, various high molecular weight HALS are described in Non-Patent Document 1. However, since there are many polar atoms in the molecular skeleton, they have low compatibility with polyolefins, are locally unevenly distributed in polyolefins, and cannot exhibit sufficient performance, and have the problem of being susceptible to bleed-out.

In Patent Document 1, HALS having a high molecular weight and being compatible with polyethylene is produced by radical copolymerizing ethylene and a hindered amine having a polymerizable functional group. However, since production requires an ultra-high pressure of 200 MPa, there are problems in that a large amount of energy is consumed and the monomer structures that can be used are limited.
In Non-Patent Document 2, HALS having a high molecular weight and being compatible with polypropylene is produced by coordination polymerizing propylene and a hindered amine having a polymerizable functional group in the presence of a transition metal. However, since the catalyst is poisoned by the polar functional group of the hindered amine, the catalytic activity is extremely low, making this method impractical.

Non-Patent Document 3 describes a method for producing HALS in which a hindered amine is introduced into an ethylene-acrylic acid ester copolymer by a transesterification reaction using a melt-kneading method. However, there is a problem in that a highly toxic tin compound is used as a reaction catalyst.

Non-Patent Document 3 introduces a product in which a nitroxyl group of hindered amine is bonded to polyethylene wax. However, in view of the mechanism of action of hindered amines, the low molecular weight hindered amines dissociate from the polyethylene wax during the development of weather resistance, so they tend to volatilize and flow out of the resin.

Non-Patent Document 4 introduces nitrile oxide as a functional group, and it is reported that it forms a carbon-carbon double bond under mild conditions and forms a stable covalent bond.
Non-Patent Document 5 reports on the production of polyolefins having double bonds in the polymer.

Polymer Additives Handbook, Toru Haruna, CMC Publishing (2010) p59-p64. Macromolecules 2000, 33, 5011-5026 Polymer Degradation and Stability 98 (2013) 2146-2152. Journal of the Society of Organic Synthetic Chemistry, 2016, Vol. 74, No. 9, p866-877. Japan Rubber Association Journal, 2010, Volume 83, Issue 9, p. 289-295

Patent No. 2695971

As described above, in order to further improve the weather resistance of polyolefins from the viewpoint of material recycling, there is a need for HALS that has excellent compatibility with polyolefins and does not volatilize or flow out.
Therefore, an object of the present invention is to provide a novel hindered amine compound that is useful as a HALS, has excellent compatibility with polyolefins, and does not volatilize or flow out, and a composition containing the hindered amine compound.

As a result of extensive studies to solve the above problems, the present inventors have discovered that the above problems can be solved by using a hindered amine compound with a specific structure, that is, a new hindered amine compound having a nitrile oxide reactive group as a HALS, The present invention has now been completed. In particular, it has been found that the effect is large when the hindered amine compound of the present invention is combined with a polyolefin having a carbon-carbon double bond. That is, the gist of the present invention is as follows.
[1] A hindered amine compound represented by the following general formula (I).

(R ¹ and R ² are each independently an alkyl group having 3 to 8 carbon atoms or an aryl group having 6 to 8 carbon atoms, and X is O (oxygen atom), CH ₂ , S (sulfur atom), or NH , R ³ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, or a COR ⁴ group, R ⁴ is an alkyl group having 1 to 4 carbon atoms, and Me is It is a methyl group.)
[2] The hindered amine compound according to the above [1], wherein X is O (oxygen atom).
[3] The hindered amine compound according to [1] or [2] above, wherein R ¹ and R ² are aryl groups having 6 to 8 carbon atoms.
[4] The hindered amine compound according to any one of [1] to [3] above, wherein R ³ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 11 carbon atoms.
[5] A composition containing the hindered amine compound according to any one of [1] to [4] above and a substance having a double bond.
[6] The composition according to [5] above, wherein the double bond-containing substance is a resin or rubber.
[7] The composition according to the above [6], wherein the resin is a polyolefin.
[8] The composition according to any one of [5] to [7] above, comprising a reactant in which at least a portion of the hindered amine compound and at least a portion of the double bond-containing substance have reacted.

According to the present invention, it is possible to provide a novel hindered amine compound that is useful as a HALS, has excellent compatibility with polyolefins, and suppresses volatilization and outflow, and a composition containing the hindered amine compound.

[Hindered amine compound]
The hindered amine compound of the present invention is represented by the following general formula (I).

In the above formula (I), R ¹ and R ² are each independently an alkyl group having 3 to 8 carbon atoms or an aryl group having 6 to 8 carbon atoms, and X is O (oxygen atom), CH ₂ , S( R ³ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, or a COR ⁴ group, and R ⁴ is an alkyl group having 1 to 4 carbon atoms. group, and Me is a methyl group.

In the above formula (I), R ¹ and R ² are each independently an alkyl group having 3 to 8 carbon atoms or an aryl group having 6 to 8 carbon atoms, and the alkyl group having 3 to 8 carbon atoms is n- Examples include propyl group, i-propyl group, n-butyl group, i-butyl group, t-butyl group, various pentyl groups, various hexyl groups, various heptyl groups, and various octyl groups. Further, examples of the aryl group having 6 to 8 carbon atoms include phenyl group, benzyl group, phenethyl group, various tolyl groups, various xylyl groups, etc. Among them, phenyl group increases the melting point of the molecule and improves handling properties. This is preferable in this respect.
R ¹ and R ² may be the same or different, but are preferably the same in terms of ease of synthesis. Therefore, in the present invention, both R ¹ and R ² are preferably phenyl groups.

X is O (oxygen atom), CH ₂ , S (sulfur atom), or NH, and O (oxygen atom) is preferable in terms of reactivity and ease of synthesis.

R ³ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, or a COR ⁴ group, and R ⁴ is an alkyl group having 1 to 4 carbon atoms.
Among these, an alkyl group having 1 to 3 carbon atoms is preferred, such as a methyl group and an ethyl group, with the methyl group being preferred because it increases the melting point of the molecule and improves handling properties.
Further, an alkoxy group having 1 to 11 carbon atoms is also preferred, and an alkoxy group having 1 to 4 carbon atoms is particularly preferred. Specific examples include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, and butoxy group. In particular, methoxy group or i-propoxy group increases the melting point of the molecule and improves handling properties. preferable.
Regarding R ⁴ of the COR ⁴ group, a methyl group or an ethyl group is preferable, and a methyl group is particularly preferable.

[Method of synthesizing hindered amine compound]
A typical method for synthesizing the hindered amine compound of the present invention uses 1,2,2,6,6-pentamethyl-4-hydroxypiperidine or a derivative thereof represented by the following formula (i) as a raw material.

Here, R ³ and Me are the same as above. This raw material (i) is reacted with a base such as sodium hydroxide, and then reacted with 1-nitro-2,2-diphenylethylene represented by the following formula (ii), resulting in the reaction represented by the following formula (iii). The hindered amine compound of the present invention represented by the following formula (iv) is obtained by using the compound as an intermediate.

In the synthesis of intermediate (iii), tetrahydrofuran, toluene, dichloromethane, etc. can be used as a solvent, and among these, tetrahydrofuran (THF) is preferred in terms of solubility. Further, the reaction temperature is preferably in the range of 0 to 30°C, more preferably in the range of 10 to 30°C. The reaction time is preferably in the range of 1 to 30 hours, more preferably 2 to 20 hours, and still more preferably 4 to 18 hours. Further, the reaction is preferably carried out in an inert gas atmosphere such as nitrogen or argon.

Next, the intermediate (iii) is reacted with 4-chlorophenylisocyanate in the presence of a triethylamine catalyst to synthesize the hindered amine compound (iv). Dichloromethane, toluene, etc. can be used as the solvent. Further, the reaction temperature is preferably in the range of 0 to 40°C, more preferably in the range of 10 to 30°C. The reaction time is preferably in the range of 1 to 30 hours, more preferably 2 to 18 hours, even more preferably 4 to 18 hours. Further, in order to remove moisture generated in the reaction system, it is preferable to use molecular sieves, and the reaction is preferably carried out in an inert gas atmosphere such as nitrogen or argon.

[Composition]
The composition of the present invention contains the hindered amine compound of the present invention and a substance having a double bond.
The hindered amine compound of the present invention can improve the heat resistance of the double bond-containing substance in a composition mixed with the double bond-containing substance.
This seems to be because the nitrile oxide group of the hindered amine compound of the present invention is added to the double bond of the double bond-containing substance to form a chemical bond. Therefore, it is thought that the hindered amine compound of the present invention, which has an effect as a HALS, suppresses outflow and volatilization even when heated, and improves the heat resistance of the polymer composition.

The substance having a double bond in the composition of the present invention is not particularly limited as long as it has a double bond, for example, if it has a double bond in either the main chain and/or the side chain. good. Specifically, resins and rubbers are preferably mentioned.
The resin only needs to have a double bond, and can be used as appropriate depending on the purpose. Preferred examples include polyolefins, such as polyethylene, polypropylene, polyisobutylene, and the like.
Further, the rubber is not particularly limited, and examples thereof include natural rubber (NR), polybutadiene rubber (BR), isoprene rubber (IR), styrene-butadiene rubber (SBR), acrylonitrile-butadiene rubber (NBR), etc. .

The composition of the present invention may contain a reactant in which the hindered amine compound of the present invention and the substance having a double bond are at least partially reacted. Hindered amine compounds and substances having double bonds begin to react when they become liquid in the reaction device, so at least a portion of them may have reacted, and compositions containing such reactants are also included in the present invention. This clarifies that it is part of the aspect of

The reaction between the hindered amine compound of the present invention and the above-mentioned double bond-containing substance may be carried out in air or in an inert atmosphere, preferably in an inert atmosphere, under nitrogen gas or argon gas. It is more preferable to carry out under gas.
The reaction may be carried out in the presence of a solvent or in the absence of a solvent, and from the viewpoint of productivity, it is preferably carried out in the absence of a solvent.
The solvent may be any solvent as long as it can dissolve the hindered amine compound of the present invention, and examples thereof include aromatic solvents (toluene, xylene, etc.) and aliphatic hydrocarbon solvents (hexane, etc.).
When the reaction is carried out in the absence of a solvent, it is preferable to use a kneading device.
Examples of the kneading device include extruders (single-screw extruder, twin-screw extruder, multi-screw extruder, etc.), kneading machines (closed kneader, Banbury mixer, etc.), and the like. The kneading device may be a continuous type or a batch type, and a continuous type is preferable from the viewpoint of production efficiency.

The reaction temperature may be any temperature at which the hindered amine compound of the present invention reacts with the substance having a double bond. For example, since it is a chemical reaction, a high temperature accelerates the reaction and increases production efficiency, so a temperature as high as possible is preferred as long as the hindered amine compound of the present invention does not decompose. The reaction temperature is preferably 0 to 400°C, more preferably 50 to 300°C, even more preferably 100 to 250°C, and particularly preferably 120 to 230°C.

(Mechanism of action)
The reason why the resin to which the hindered amine compound of the present invention is added exhibits higher heat resistance than the resin to which the conventional hindered amine additive is added is that the nitrile oxide group in the hindered amine compound of the present invention is It is presumed that this is because it reacts with the unsaturated bonds of the resin, forms stable chemical bonds, and is incorporated into the resin skeleton, thereby suppressing volatilization and outflow.

EXAMPLES Hereinafter, the present invention will be described in more detail based on Examples, but the present invention is not limited to the following Examples unless it exceeds the gist thereof.

<Polymer physical property measurement, analysis, etc.>
(GPC measurement)
The mass average molecular weight (Mw), number average molecular weight (Mn), and molecular weight distribution (Mw/Mn) of the polymer were determined by GPC measurement. GPC measurements were performed using Alliance GPCV2000 manufactured by Waters.
A differential refractometer was used as a detector, and four columns, TSKgel GMH6-HT manufactured by Tosoh Corporation, were used. Orthodichlorobenzene was used as a mobile phase solvent, and the flow rate was 135° C. and 1.0 mL/min.
Monodisperse polystyrene manufactured by Polymer Laboratories was used as the standard sample, a calibration curve regarding retention time and molecular weight was created from the polystyrene standard sample and the polyolefin viscosity formula, and the molecular weight was calculated based on the calibration curve. Polystyrene standard samples include those with molecular weights of 2,783,000, 1,412,000, 590,500, 164,500, 72,450, 29,510, 10,730, 3,950, 1,530, and 580. Ten points were used.
[η]=K×Mα is used as the viscosity formula, and for polystyrene K=1.38×10 ⁻⁴ and α=0.70 are used, and for polyethylene K=4.77×10 ⁻⁴ and α =0.70 was adopted, and for polypropylene, K=1.03×10 ⁻⁴ and α=0.78 were adopted.

(DSC measurement)
The melting point (Tm) of the polymer was determined by DSC measurement. For the DSC measurement, Diamond DSC manufactured by PerkinElmer was used. For the sample, isothermal at 20°C for 1 minute, heated at 10°C/min from 20°C to 210°C, isothermal at 210°C for 5 minutes, cooled from 210°C to -70°C at 10°C/min, and heated at -70°C for 5 minutes. The melting point was determined by measurement when the temperature was raised from -70°C to 210°C at a rate of 10°C/min after isothermal heating for 10 minutes.

(Melt flow rate (MFR))
Regarding polyethylene, the MFR was measured at a test temperature of 190° C. and a nominal load of 2.16 kg (21.17 N) in accordance with JIS K 7210:2004 Annex A Table 1-Condition D.
For polypropylene, the MFR was measured at a test temperature of 230° C. and a nominal load of 2.16 kg (21.17 N) in accordance with JIS K 7210:2004 Annex A Table 1-Condition M.

<Raw materials used>
Polyethylene: ethylene-propylene copolymer Mw=68,500, Mn=23,900, Mw/Mn=2.87,
Tm=90°C, MFR (190°C)=11g/10min,
Density = 0.911g/cm ³ ,
Propylene unit ratio: 7.5 mol%,
Number of vinyl groups = 18.9 μmol/g
Number of vinylidene groups = 19.7 μmol/g
Number of vinylene groups = 11.4 μmol/g, 0.47 pieces/piece,
Number of trisubstituted olefins = 33 μmol/g, 0.45 pieces/piece.

[Synthesis example 1]
(Synthesis of 1-nitro-2,2-diphenylethylene)
Chemical Communications, Volume 49, 2013, p. 1-nitro-2,2-diphenylethylene was synthesized according to the method described in No. 7723-7725.

As shown in the reaction formula below, 1,2,2,6,6-pentamethyl-4-hydroxypiperidine, a commercially available product (Wako Chemical Co.), is reacted with 1-nitro-2,2-diphenylethylene synthesized above. Thus, hindered amine compound A was obtained.

The detailed synthesis method is as follows.
(Synthesis of compound A-1)
19.0 g (111 mmol) of 1,2,2,6,6-pentamethyl-4-hydroxypiperidine was dissolved in 150 mL of dehydrated tetrahydrofuran (THF) and cooled to 0°C. To this solution, 2.93 g (122 mmol) of sodium hydride was added under nitrogen gas, and the mixture was stirred at 0° C. for 1 hour. To this liquid, 10 g (44 mmol) of 1-nitro-2,2-diphenylethylene was added, and the mixture was stirred at 20° C. for 16 hours. After the solution was cooled to 0° C., it was neutralized with a 2 mol/L aqueous hydrogen chloride solution until the pH became 6 to 7.
The solution after neutralization was extracted using dichloromethane. The dichloromethane solution was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified. The obtained solid was washed with a 1/1 solution of ethyl acetate/petroleum ether to obtain 17 g of compound A-1 as a yellow solid (yield 97%).

(Synthesis of hindered amine compound A)
17 g (42.9 mmol) of Compound A-1 was dissolved in 900 mL of dehydrated dichloromethane. To this solution were added 23 g (150 mmol) of 4-chlorophenylisocyanate, 11.2 g (110 mmol) of triethylamine, and 30 g of Molecular Sieves 4A, and the mixture was stirred at 20° C. for 16 hours under nitrogen gas. The solution was filtered, the filtrate was concentrated, and then purified by column chromatography (acidic silica gel, solvent: n-hexane/ethyl acetate 1/0, 1/1). 11.3 g of yellow solid nitrile oxide compound A was obtained (yield 70%).
The NMR spectrum of hindered amine compound A is shown below, and it was confirmed that it is hindered amine compound A.
¹ H-NMR (400 MHz, CDCl ₃ ): δ7.48-7.30 (m, 10H), 3.86 (m, 1H), 2.17 (s, 3H), 1.7-1.63 ( m, 2H), 1.55 (m, 2H), 1.11 (s, 6H), 0.84 (s, 6H) ppm.

[Synthesis example 2]
(Synthesis of 1-methoxy-2,2,6,6-pentamethyl-4-hydroxypiperidine)
1-methoxy-2,2,6,6-pentamethyl-4-hydroxypiperidine was synthesized according to the method described in J. Org. Chem. 2009, 74, 1567-1573.

As shown in the reaction formula below, 1-methoxy-2,2,6,6-pentamethyl-4-hydroxypiperidine is reacted with 1-nitro-2,2-diphenylethylene synthesized in Example 1 to form a hindered amine. Compound B was obtained.

The detailed synthesis method is as follows.
(Synthesis of compound B-1)
5.0 g (12.6 mmol) of 1-methoxy-2,2,6,6-pentamethyl-4-hydroxypiperidine was dissolved in 100 mL of dehydrated tetrahydrofuran (THF) and cooled to 0°C. To this solution, 0.33 g (13.9 mmol) of sodium hydride was added under nitrogen gas, and the mixture was stirred at 0° C. for 1 hour. 3.41 g (15.1 mmol) of 1-nitro-2,2-diphenylethylene was added to this liquid, and the mixture was stirred at 20° C. for 16 hours. After the solution was cooled to 0° C., it was neutralized with a 2 mol/L aqueous hydrogen chloride solution until the pH became 6 to 7.
The solution after neutralization was extracted using dichloromethane. The dichloromethane solution was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified. The obtained solid was washed with a 1/1 solution of ethyl acetate/petroleum ether to obtain 4.57 g of compound B-1 as a yellow solid (yield: 88%).

23.4 g (56.7 mmol) of Compound B-1 was dissolved in 900 mL of dehydrated toluene. To this solution were added 30.7 g (200 mmol) of 4-chlorophenylisocyanate, 30.6 g (199 mmol) of triethylamine, and 30 g of Molecular Sieves 4A, and the mixture was stirred at 20° C. for 16 hours under nitrogen gas. The solution was filtered, the filtrate was concentrated, and then purified by column chromatography (acidic silica gel, solvent: n-hexane/ethyl acetate 1/0, 1/1). 10.3 g of nitrile oxide compound B as a pale yellow solid was obtained (yield: 46 g%).
The NMR spectrum of hindered amine compound B is shown below, and it was confirmed that it is hindered amine compound B.
^1H -NMR (400MHz, CDCl ₃ ): δ7.45-7.30 (m, 10H), 3.83 (m, 1H), 3.57 (s, 3H), 1.62 (d, 4H) , 1.15 (s, 6H), 0.94 (s, 6H) ppm.

[Example 1]
(Mixture of polymer and hindered amine compound A)
For mixing the above-mentioned polymer and hindered amine compound A, a "Laboplasto Mill C model" manufactured by Toyo Seiki Seisakusho, Ltd., equipped with a segment mixer R60 (inner volume 60 cc) and a roller type blade was used.
After pouring the entire amount of polyethylene into the mixer of Laboplasto Mill, which had been preheated to 130° C. while rotating the blade at low speed, 42 mg of an antioxidant (manufactured by BASF, IRGANOX (registered trademark) 1010) and 42 mg of hindered amine compound A were added. , and the blade rotation speed was increased to 50 rpm to start mixing. After 5 minutes, rotation was stopped and the bulk sample was collected.

(Polymer purification/analysis)
500 mg of the above lump sample cut into several mm squares with scissors and 10 mL of dehydrated xylene were put into a flask, and then stirred in an oil bath at 120° C. for 20 minutes under nitrogen gas to completely dissolve. 50 mL of acetone was added to this solution to precipitate the polymer. The precipitated polymer was collected by filtration and dried under reduced pressure at 60° C. for 4 hours or more.

30 mg of the obtained polymer was dissolved in 0.7 mL of o-dichlorobenzene-d2, and ¹ H-NMR was measured at 120°C. A signal (2H) derived from the vinyl group at 4.9 ppm and a signal (1H) derived from the isoxazoline ring at approximately 4.5 ppm were observed, confirming that the nitrile oxide group of hindered amine compound A was added to the double bond. did.

(Creation of film sample)
A film sample with a thickness of about 0.5 mm was obtained by heat pressing the unpurified mixed sample at 190° C. for 2 minutes using two ferro plates and a 0.5 mm spacer in a heat press machine.

(Heat resistance evaluation of film sample)
Heat resistance was evaluated by TG-DTA measurement. For the TG-DTA measurement, a differential thermal balance "TG-DTA8122" manufactured by Rigaku Corporation was used, and "Thermo plus EVO2" manufactured by Rigaku Corporation was used as the measurement and analysis software.
As the sample pan, an aluminum pan with a diameter of 5 mm and a height of 2.5 mm was used. The measurement sample used was a film sample of 1.9 to 2.1 mg cut into a square. The measurement was performed at 30°C for 30 minutes under a nitrogen flow of 300 mL/min, then the temperature was raised to 220°C at a rate of 10°C/min, and at the same time, the atmosphere was changed to an air flow of 300 mL/min and held at 220°C. The retention time when the weight decreased by 10% was evaluated. The evaluation results are shown in Table 1.

[Example 2]
In Example 1, a film sample was prepared in the same manner as in Example 1 except that hindered amine compound B was used instead of hindered amine compound A, and evaluated in the same manner. The evaluation results are shown in Table 1.

[Comparative example 1]
In Example 1, a film sample was prepared in the same manner as in Example 1, except that a commercially available HALS, "ADEKA STAB LA-63P" manufactured by ADEKA, was used in place of hindered amine compound A. evaluated. The evaluation results are shown in Table 1.

As shown in Table 1, the polyethylene to which the hindered amine compound of the present invention was added had a longer 10% weight loss time than the polyethylene to which the commercially available HALS shown in the comparative example was added. That is, it can be seen that polyethylene using the hindered amine compound of the present invention has improved heat resistance.
This is presumably because the nitrile oxide group of the hindered amine compound of the present invention is added to the double bond of polyethylene to form a chemical bond. Therefore, it is thought that the hindered amine compound of the present invention, which has an effect as a HALS, suppresses outflow and volatilization and improves the heat resistance of the polymer composition.

Since the resin to which the hindered amine compound of the present invention is added can exhibit higher heat resistance than the resin to which the conventional hindered amine additive is added, the hindered amine compound of the present invention has extremely high industrial value. .

Claims (8)

A hindered amine compound represented by the following general formula (I).

(R ¹ and R ² are each independently an alkyl group having 3 to 8 carbon atoms or an aryl group having 6 to 8 carbon atoms, and X is O (oxygen atom), CH ₂ , S (sulfur atom), or NH , R ³ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, or a COR ⁴ group, R ⁴ is an alkyl group having 1 to 4 carbon atoms, and Me is It is a methyl group.) The hindered amine compound according to claim 1, wherein X is O (oxygen atom). The hindered amine compound according to claim 1 or 2, wherein R ¹ and R ² are aryl groups having 6 to 8 carbon atoms. The hindered amine compound according to any one of claims 1 to 3, wherein R ³ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 11 carbon atoms. A composition comprising the hindered amine compound according to any one of claims 1 to 4 and a substance having a double bond. 6. The composition according to claim 5, wherein the double bond-containing substance is a resin or a rubber. 7. The composition of claim 6, wherein the resin is a polyolefin. The composition according to any one of claims 5 to 7, comprising a reactant in which at least a portion of the hindered amine compound and at least a portion of the double bond-containing substance have reacted.