Hindered amine compounds and compositions

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

[Technical Field]

[0001] The present invention relates to hindered amine compounds and compositions containing hindered amine compounds. [Background technology]

[0002] Polyolefin resins, such as polyethylene and polypropylene, are inexpensive and offer excellent advantages such as moldability, heat resistance, chemical resistance, mechanical properties, and low specific gravity. They are used in various molding processes, including injection molding, extrusion molding, and film molding, and their molded products are widely used in various fields. Furthermore, it is common practice to incorporate stabilizers such as antioxidants when using these resins. For example, for outdoor use, weather resistance is a concern, so it is common practice to incorporate hindered amine light stabilizers (HALS) into the resin.

[0003] In recent years, there has been a demand for further improvement in the weather resistance of polyolefins from the perspective of material recycling. One of the reasons for the decrease in weather resistance of molded products containing HALS is the bleeding of HALS onto the surface and its leaching or volatilization from the surface due to rain, etc. Therefore, a common method for improving the performance of HALS is to increase its molecular weight.

[0004] For example, Non-Patent Document 1 describes various high molecular weight HALS. However, because they contain many polar atoms in their molecular framework, they have low compatibility with polyolefins, resulting in localized uneven distribution within the polyolefins and inability to fully exhibit their properties. In addition, they are prone to bleed-out.

[0005] Patent Document 1 describes the production of HALS, which is highly molecular weight and compatible with polyethylene, by radical copolymerization of ethylene with a hindered amine having a polymerization functional group. However, this requires an ultra-high pressure of 200 MPa for production, resulting in significant energy consumption and limitations on the usable monomer structures. Non-patent document 2 describes the production of high molecular weight HALS compatible with polypropylene by coordination polymerization of propylene and a hindered amine having polymerization functional groups in the presence of a transition metal. However, the catalyst is poisoned by the polar functional groups of the hindered amine, resulting in extremely low catalytic activity and making it impractical.

[0006] Non-patent document 3 describes a method for producing HALS by introducing a hindered amine via a transesterification reaction using a melt-kneading method with an ethylene-acrylic acid ester copolymer. However, it has the drawback of using a highly toxic tin compound as a reaction catalyst.

[0007] Non-patent document 3 introduces a product in which the nitroxyl group of a hindered amine is bonded to polyethylene wax. However, considering the mechanism of action of hindered amines, low-molecular-weight hindered amines dissociate from the polyethylene wax during the development of weather resistance, making them prone to volatilization and leakage from the resin.

[0008] Non-patent document 4 introduces nitrile oxides as functional groups and reports that they form carbon-carbon double bonds under mild conditions, thereby creating stable covalent bonds. Non-patent document 5 reports on the production of polyolefins having double bonds in the polymer. [Prior art documents] [Non-patent literature]

[0009] [Non-Patent Document 1] Handbook of Polymer Additives, by Toru Haruna, CMC Publishing (2010), pp. 59-64. [Non-Patent Document 2] Macromolecules 2000, 33, 5011-5026 [Non-Patent Document 3] Polymer Degradation and Stability 98 (2013) 2146-2152. [Non-Patent Document 4] Journal of Organic Synthetic Chemistry, Vol. 74, No. 9, pp. 866-877, 2016

Non-Patent Document 5

Patent Document

[0010]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0011] As described above, from the perspective of material recycling, there is a need for a HALS that has excellent compatibility with polyolefin and does not volatilize or leak out for the purpose of further improving the weather resistance of polyolefin. 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 polyolefin, and does not volatilize or leak out, and a composition containing the hindered amine compound.

Means for Solving the Problems

[0012] As a result of intensive studies to solve the above problems, the present inventor has found that the above problems can be solved by using a hindered amine compound having a specific structure, that is, a novel hindered amine compound having a nitrile oxide reactive group as a HALS, and has completed the present invention. In particular, it has been found that the effect is great by combining the hindered amine compound of the present invention 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).

Chemical Formula

[0013] According to the present invention, it is possible to provide novel hindered amine compounds that are useful as HALS, have excellent compatibility with polyolefins, and have suppressed volatilization and leakage, as well as compositions containing hindered amine compounds. [Modes for carrying out the invention]

[0014] [Hindered amine compounds] The hindered amine compound of the present invention is represented by the following general formula (I).

[0015]

Chem.

[0016] 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, X is O (oxygen atom), CH2, S (sulfur atom), or NH, and 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 a methyl group.

[0017] 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. Examples of the alkyl group having 3 to 8 carbon atoms include an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a t-butyl group, various pentyl groups, various hexyl groups, various heptyl groups, and various octyl groups. Examples of the aryl group having 6 to 8 carbon atoms include a phenyl group, a benzyl group, a phenethyl group, various tolyl groups, and various xylyl groups. Among them, the phenyl group is preferable in terms of increasing the melting point of the molecule and improving the handling property. 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, it is preferable that both R 1 and R 2 are phenyl groups.

[0018] X is O (oxygen atom), CH2, S (sulfur atom), or NH, and O (oxygen atom) is preferable in terms of reactivity and ease of synthesis.

[0019] 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 4It is a base, R 4 These are alkyl groups with 1 to 4 carbon atoms. Among these, alkyl groups having 1 to 3 carbon atoms are preferred, for example, methyl groups and ethyl groups are preferred, with methyl groups being preferred because they increase the melting point of the molecule and improve handling properties. Furthermore, alkoxy groups having 1 to 11 carbon atoms are also preferred, and among them, alkoxy groups having 1 to 4 carbon atoms are preferred. Specifically, examples include methoxy groups, ethoxy groups, n-propoxy groups, i-propoxy groups, and butoxy groups, with methoxy groups or i-propoxy groups being particularly preferred in that they increase the melting point of the molecule and improve handling properties. COR 4 Base R 4 Regarding this, a methyl group is preferred, an ethyl group is preferred, and a methyl group is particularly preferred.

[0020] [Method for synthesizing hindered amine compounds] A typical synthesis method for the hindered amine compounds 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 starting material.

[0021] [ka]

[0022] Here, R 3 And Me are as described above. After reacting this raw material (i) with a base such as sodium hydroxide, the mixture is reacted with 1-nitro-2,2-diphenylethylene represented by the following formula (ii), and the compound represented by the following formula (iii) is obtained as an intermediate, and the hindered amine compound of the present invention represented by the following formula (iv) is obtained.

[0023] [ka]

[0024] [ka]

[0025] [ka]

[0026] In the synthesis of intermediate (iii), tetrahydrofuran, toluene, dichloromethane, etc., can be used as the solvent, with tetrahydrofuran (THF) being preferred in terms of solubility. The reaction temperature is preferably in the range of 0 to 30°C, and 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 even more preferably 4 to 18 hours. The reaction is preferably carried out in an inert gas atmosphere such as nitrogen or argon.

[0027] Next, the above intermediate (iii) is reacted with 4-chlorophenyl isocyanate in the presence of a triethylamine catalyst to synthesize a hindered amine compound (iv). Dichloromethane, toluene, etc., can be used as the solvent. The reaction temperature is preferably in the range of 0 to 40°C, and 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, and even more preferably 4 to 18 hours. Molecular sieves are preferably used to remove water generated in the reaction system, and the reaction is preferably carried out in an inert gas atmosphere such as nitrogen or argon.

[0028] [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 a substance having a double bond in a composition in which it is mixed with the substance having a double bond. This is thought to be because the nitrile oxide group of the hindered amine compound of the present invention is added to the double bond of a substance having a double bond, forming a chemical bond. Therefore, it is believed that the hindered amine compound of the present invention, which has the effect of HALS, suppresses leaching and volatilization even when heated, and improves the heat resistance of the polymer composition.

[0029] 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, it may have a double bond in either the main chain and / or the side chain. Specifically, resins or rubbers are preferred examples. The resin can have any double bond and can be used as appropriate depending on the application. Polyolefins are preferred, such as polyethylene, polypropylene, and polyisobutylene. Furthermore, there are no particular restrictions on the type of rubber used; examples include natural rubber (NR), polybutadiene rubber (BR), isoprene rubber (IR), styrene-butadiene rubber (SBR), and acrylonitrile-butadiene rubber (NBR).

[0030] The composition in the present invention may include a reaction product in which at least a portion of the hindered amine compound of the present invention and the substance having the double bond have reacted. Since the reaction begins when the hindered amine compound and the substance having the double bond become liquid in the reaction apparatus, at least a portion of them may have reacted, and it is important to clarify that compositions containing such reaction products are also part of the embodiments of the present invention.

[0031] The reaction between the hindered amine compound of the present invention and the substance having the double bond may be carried out under air or under an inert atmosphere, preferably under an inert atmosphere, and more preferably under nitrogen gas or argon gas. The reaction may be carried out in the presence or absence of a solvent, but from the viewpoint of productivity, it is preferable to carry it out in the absence of a solvent. Any solvent capable of dissolving the hindered amine compound of the present invention is acceptable, and examples 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 apparatus. Examples of mixing equipment include extruders (single-screw extruders, twin-screw extruders, multi-screw extruders, etc.) and kneaders (closed-type kneaders, Banbury mixers, etc.). The mixing equipment may be continuous or batch type, but from the viewpoint of production efficiency, the continuous type is preferred.

[0032] The reaction temperature should be such that the hindered amine compound of the present invention reacts with the substance having the double bond. For example, since it is a chemical reaction, a higher temperature will accelerate the reaction and increase production efficiency, so a temperature as high as possible is preferable, 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.

[0033] (Mechanism of action) The reason why resins to which the hindered amine compound of the present invention is added exhibit higher heat resistance compared to resins to which conventional hindered amine additives are added is presumed to be because the nitrile oxide group in the hindered amine compound of the present invention reacts with unsaturated bonds in the resin, forming stable chemical bonds that are incorporated into the resin skeleton, thereby suppressing volatilization and leakage. [Examples]

[0034] The present invention will be described in more detail below based on examples, but the present invention is not limited to the following examples as long as it does not exceed the gist of the invention.

[0035] <Measurement and analysis of polymer properties, 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 a Waters Alliance GPCV2000. A differential refractometer was used as the detector, and four TSKgel GMH6-HT columns manufactured by Tosoh Corporation were used. Orthodichlorobenzene was used as the mobile phase solvent and eluted at 135°C and 1.0 mL / min. Monodisperse polystyrene from Polymer Laboratories was used as the standard sample. Calibration curves relating retention time and molecular weight were created from the viscosity formulas of the polystyrene standard sample and polyolefin, and the molecular weight was calculated based on the calibration curves. Ten polystyrene standard samples were used, 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. The viscosity formula used is [η] = K × Mα, and for polystyrene, K = 1.38 × 10 -4 We adopted α=0.70, and for polyethylene, K=4.77×10 -4 For polypropylene, α=0.70 was adopted, and K=1.03×10 -4 We adopted α = 0.78.

[0036] (DSC measurement) The melting point (Tm) of the polymer was determined by DSC measurement. A DiamondDSC from PerkinElmer was used for DSC measurement. For each sample, the melting point was determined by isothermal heating at 20°C for 1 minute, heating from 20°C to 210°C at a rate of 10°C / min, isothermal heating at 210°C for 5 minutes, cooling from 210°C to -70°C at a rate of 10°C / min, isothermal heating at -70°C for 5 minutes, and then heating from -70°C to 210°C at a rate of 10°C / min.

[0037] (Melt Flow Rate (MFR)) For polyethylene, the measured values ​​were shown as MFR (Metal Fiber Rate) according to JIS K 7210:2004, Annex A, Table 1 - Condition D, at a test temperature of 190°C and a nominal load of 2.16 kg (21.17 N). For polypropylene, the measured values ​​were shown as MFR (Metal Frame Rate) at a test temperature of 230°C and a nominal load of 2.16 kg (21.17 N), in accordance with Annex A, Table 1 - Condition M of JIS K 7210:2004.

[0038] <Raw materials used> Polyethylene: Ethylene-propylene copolymer Mw=68,500, Mn=23,900, Mw / Mn=2.87, Tm=90℃, MFR(190℃)=11g / 10min, Density=0.911g / cm 3 , Property of propylene units: 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 groups / tube Number of trisubstituted olefins = 33 μmol / g, 0.45 cells / string.

[0039] [Synthesis Example 1] (Synthesis of 1-nitro-2,2-diphenylethylene) 1-nitro-2,2-diphenylethylene was synthesized according to the method described in Chemical Communications, Vol. 49, 2013, pp. 7723-7725.

[0040] As shown in the following reaction equation, hindered amine compound A was obtained by reacting commercially available 1,2,2,6,6-pentamethyl-4-hydroxypiperidine (Wako Chemical Co.) with 1-nitro-2,2-diphenylethylene synthesized above.

[0041] [ka]

[0042] 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 anhydrous tetrahydrofuran (THF) and cooled to 0°C. 2.93 g (122 mmol) of sodium hydride was added to this solution under nitrogen gas, and the mixture was stirred at 0°C for 1 hour. 10 g (44 mmol) of 1-nitro-2,2-diphenylethylene was added to this solution, and the mixture was stirred at 20°C for 16 hours. After cooling the solution to 0°C, it was neutralized with a 2 mol / L aqueous hydrogen chloride solution until the pH reached 6-7. The neutralized solution was extracted using dichloromethane. The dichloromethane solution was washed with saturated saline solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified. The resulting solid was washed with ethyl acetate / petroleum ether = 1 / 1 solution to obtain 17 g of compound A-1 as a yellow solid (yield 97%).

[0043] (Synthesis of hindered amine compound A) 17 g (42.9 mmol) of compound A-1 was dissolved in 900 mL of anhydrous dichloromethane. To this solution, 23 g (150 mmol) of 4-chlorophenyl isocyanate, 11.2 g (110 mmol) of triethylamine, and 30 g of molecular sieves 4A were added, and the mixture was stirred under nitrogen gas at 20°C for 16 hours. The solution was filtered, and the filtrate was concentrated and purified by column chromatography (acidic silica gel, solvent: n-hexane / ethyl acetate 1 / 0, 1 / 1). 11.3 g of nitrile oxide compound A was obtained as a yellow solid (yield 70%). The NMR spectrum of hindered amine compound A is shown below, confirming that it is indeed hindered amine compound A. 1 H-NMR (400MHz, CDCl3): 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.

[0044] [Synthesis Example 2] (1-Methoxy-2,2,6,6-pentamethyl-4-hydroxypiperidine synthesis) 1-Methoxy-2,2,6,6-pentamethyl-4-hydroxypiperidine was synthesized according to the method described in J. Org. Chem. 2009, 74, 1567-1573.

[0045] As shown in the following reaction equation, 1-methoxy-2,2,6,6-pentamethyl-4-hydroxypiperidine was reacted with 1-nitro-2,2-diphenylethylene synthesized in Example 1 to obtain hindered amine compound B.

[0046] [ka]

[0047] 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 anhydrous 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. To this solution, 3.41 g (15.1 mmol) of 1-nitro-2,2-diphenylethylene was added and the mixture was stirred at 20°C for 16 hours. After cooling the solution to 0°C, it was neutralized with 2 mol / L aqueous hydrogen chloride solution until the pH was 6-7. The neutralized solution was extracted using dichloromethane. The dichloromethane solution was washed with saturated saline solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified. The resulting solid was washed with ethyl acetate / petroleum ether = 1 / 1 solution to obtain 4.57 g of compound B-1 as a yellow solid (yield 88%).

[0048] 23.4 g (56.7 mmol) of compound B-1 was dissolved in 900 mL of anhydrous toluene. To this solution, 30.7 g (200 mmol) of 4-chlorophenyl isocyanate, 30.6 g (199 mmol) of triethylamine, and 30 g of molecular sieves 4A were added, and the mixture was stirred at 20°C for 16 hours under nitrogen gas. The solution was filtered, and the filtrate was concentrated and purified by column chromatography (acidic silica gel, solvent: n-hexane / ethyl acetate 1 / 0, 1 / 1). 10.3 g of nitrile oxide compound B was obtained as a pale yellow solid (yield 46 g%). The NMR spectrum of hindered amine compound B is shown below, confirming that it is indeed hindered amine compound B. 1 H-NMR (400MHz, CDCl3): 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.

[0049] [Example 1] (Mixture of polymer and hindered amine compound A) For mixing the aforementioned polymer and hindered amine compound A, a segment mixer R60 (internal volume 60cc) and a "Laboplast Mill C model" manufactured by Toyo Seiki Seisakusho, equipped with roller-type blades, were used. The entire amount of polyethylene was added to a Laboplast Mill mixer preheated to 130°C while the blades were rotated at a low speed. Then, 42 mg of antioxidant (BASF, IRGANOX® 1010) and 42 mg of hindered amine compound A were added in succession, and the blade rotation speed was increased to 50 rpm to start mixing. After 5 minutes, the rotation was stopped and the lumpy sample was collected.

[0050] (Purification and analysis of polymers) The above-mentioned lumpy sample was cut into several-millimeter squares with scissors, and 500 mg of each piece, along with 10 mL of anhydrous xylene, were placed in a flask. The flask was then stirred in an oil bath under nitrogen gas at 120°C for 20 minutes to completely dissolve the sample. 50 mL of acetone was added to this solution to precipitate the polymer. The precipitated polymer was recovered by filtration and dried under reduced pressure at 60°C for at least 4 hours.

[0051] Dissolve 30 mg of the obtained polymer in 0.7 mL of o-dichlorobenzene-d2 and heat at 120°C. 1 1H-NMR was measured. A signal originating from the vinyl group (2H) at 4.9 ppm and a signal originating from the isoxazoline ring (1H) at approximately 4.5 ppm were observed, confirming that the nitrile oxide group of hindered amine compound A is attached to the double bond.

[0052] (Creating film samples) An unrefined mixed sample was heated and pressed at 190°C for 2 minutes using a hot press machine with two ferroplates and a 0.5 mm spacer to obtain a film sample with a thickness of approximately 0.5 mm.

[0053] (Evaluation of heat resistance of film samples) The heat resistance was evaluated by TG-DTA measurement. A Rigaku TG-DTA8122 differential thermal balance was used for the TG-DTA measurement, and Rigaku Thermo plus EVO2 was used as the measurement and analysis software. A sample pan measuring φ5 mm × height 2.5 mm was used. The measurement samples were 1.9–2.1 mg of film sample cut into squares. The measurement was performed by isothermal heating at 30°C for 30 minutes under a 300 mL / min nitrogen stream, then increasing the temperature to 220°C at 10°C / min. Simultaneously, the atmosphere was switched to 300 mL / min air, and the temperature was maintained at 220°C. The holding time at which the sample decreased by 10% by weight was evaluated. The evaluation results are shown in Table 1.

[0054] [Example 2] In Example 1, film samples were prepared and evaluated in the same manner as in Example 1, except that hindered amine compound B was used instead of hindered amine compound A. The evaluation results are shown in Table 1.

[0055] [Comparative Example 1] In Example 1, film samples were prepared and evaluated in the same manner as in Example 1, except that a commercially available HALS, "ADEKA STAB LA-63P" manufactured by ADEKA Corporation, was used instead of hindered amine compound A. The evaluation results are shown in Table 1.

[0056] [Table 1]

[0057] As shown in Table 1, polyethylene to which the hindered amine compound of the present invention was added had a 10% weight reduction time longer than commercially available polyethylene to which HALS was added, as shown in the comparative example. In other words, it can be seen that polyethylene using the hindered amine compound of the present invention has improved heat resistance. This is thought to be because the nitrile oxide group of the hindered amine compound of the present invention is added to the double bond of polyethylene, forming a chemical bond. Therefore, the hindered amine compound of the present invention, which has the effect of HALS, is thought to suppress leaching and volatilization, and improve the heat resistance of the polymer composition. [Industrial applicability]

[0058] Since resins to which the hindered amine compound of the present invention is added exhibit higher heat resistance compared to resins to which conventional hindered amine additives are added, the hindered amine compound of the present invention has extremely high industrial value.

Claims

1. A hindered amine compound represented by the following general formula (I). 【Chemistry 1】 (R １ and R ２ Each of these is an aryl group having 6 to 8 carbon atoms, X is O (oxygen atom), and 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 COR ４ It is a base, R ４ (where is an alkyl group having 1 to 4 carbon atoms, and Me is a methyl group.)

2. R ３ The hindered amine compound according to claim 1, wherein is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 11 carbon atoms.

3. A composition containing the hindered amine compound described in claim 1 or 2 and a substance having a double bond.

4. The composition according to claim 3, wherein the substance having the double bond is a resin or rubber.

5. The composition according to claim 4, wherein the resin is a polyolefin.

6. The composition according to any one of claims 3 to 5, comprising a reactant obtained by the reaction of at least a portion of the hindered amine compound with at least a portion of the substance having a double bond.

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