Composition, resin composition, molded article, method for producing resin composition, method for flame-retardantizing synthetic resin, and additive
Patent Information
- Application Number
- PCT/JP2026/008832
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2025-03-14
- Filing Date
- 2026-03-09
- Publication Date
- 2026-09-17
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Figure JP2026008832_17092026_PF_FP_ABST
Abstract
Description
Composition, resin composition, molded article, method for manufacturing a resin composition, method for flame retarding a synthetic resin, and additives
[0001] The present invention relates to a composition that imparts excellent flame retardancy to a synthetic resin without degrading its color tone, a resin composition having excellent color tone and excellent flame retardancy, and a molded article thereof, a method for producing a resin composition, a method for flame retarding a synthetic resin, and additives.
[0002] One known method for flame retarding synthetic resins involves adding a flame retardant containing an N-alkoxy hindered amine compound and a melamine-based flame retardant. For example, Patent Document 1 discloses a flame-retardant polyolefin article containing an N-alkoxy hindered amine, melamine cyanurate, and a phosphonic acid ester. Patent Document 2 discloses a laminate of flame-retardant olefin resin film using a flame retardant containing a NOR-type light stabilizer, melamine cyanurate, and a phosphate ester compound.
[0003] US2018 / 201838A1 Japanese Patent Publication No. 2004-174869
[0004] However, adding N-alkoxy-type hindered amine compounds to resins can increase the yellowness of the resin, impairing the appearance of molded products. The object of the present invention is to provide a composition that imparts excellent flame retardancy to synthetic resins while suppressing the increase in yellowness of the synthetic resins.
[0005] As a result of diligent research to solve the above problems, the present inventors have found that a composition containing a hindered amine compound having a specific structure and a nitrogen-containing heterocyclic compound solves the above problems, and have completed the present invention.
[0006] The present invention provides a composition containing (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound. In general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R5 and R 6 each independently represent an alkyl group having 1 to 4 carbon atoms. In general formula (2), R 7 and R in general formula (3) 8 each represent a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formula (2), general formula (3) and formula (4), * represents a bonding site.
[0007] Further, according to the present invention, there is provided a resin composition comprising: (A) a hindered amine compound represented by general formula (1); (B) a nitrogen-containing heterocyclic compound; and a synthetic resin. In general formula (1), R 1 represents a group represented by the following general formula (2), a group represented by general formula (3) or a group represented by formula (4), R 2 represents a hydrocarbon group having 1 to 18 carbon atoms, and R 3 , R 4 , R 5 and R 6 each independently represent an alkyl group having 1 to 4 carbon atoms. In general formula (2), R 7 and R in general formula (3) 8 each represent a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formula (2), general formula (3) and formula (4), * represents a bonding site.
[0008] Further, according to the present invention, there is provided a molded article obtained from the above resin composition.
[0009] Further, according to the present invention, there is provided a method for producing a resin composition, comprising a blending step of blending (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound into a synthetic resin. In general formula (1), R 1 represents a group represented by the following general formula (2), a group represented by general formula (3) or a group represented by formula (4), R 2 represents a hydrocarbon group having 1 to 18 carbon atoms, and R 3 , R 4 , R 5 and R 6 each independently represent an alkyl group having 1 to 4 carbon atoms. R in general formula (2) 7 and R in general formula (3) 8 * represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
[0010] Furthermore, the present invention provides a method for making a synthetic resin flame-retardant by blending the synthetic resin with (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound. In general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. R in general formula (2) 7 and R in general formula (3) 8 * represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
[0011] Furthermore, the present invention provides an additive for preparing a composition comprising (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound, wherein the additive contains the above-mentioned (A) hindered amine compound represented by general formula (1). In general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. R in general formula (2) 7 and R in general formula (3) 8* represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
[0012] Embodiments of the present invention will be described in detail below. Only one of the upper and lower limits of the numerical values described herein may be specified. Furthermore, when combining upper and lower limits, any combination may be used. <Composition> The composition of this embodiment contains (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound. (Hereinafter, these will also be referred to as "component (A)" and "component (B)," respectively.)
[0013] In general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. R in general formula (2) 7 and R in general formula (3) 8 * represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
[0014] According to the composition of this embodiment, excellent flame retardancy can be imparted to the synthetic resin without degrading its color tone. Furthermore, as shown in the examples described later, according to the composition of this embodiment, the deterioration of the mechanical properties of the resin composition can also be effectively suppressed.
[0015] Here, the reason why the composition of this embodiment can impart excellent flame retardancy to synthetic resins is not clear, but it is inferred as follows: (A) The hindered amine compound represented by general formula (1) decomposes with the heat of combustion and exhibits a flame retardant effect by capturing hydroxyl radicals and alkyl peroxy radicals generated in the gas phase with the hindered amine structure. (B) The nitrogen-containing heterocyclic compound generates non-combustible gases such as nitrogen molecules and ammonia during combustion and exhibits a flame retardant effect by diluting the flammable gas and oxygen in the gas phase. In the composition of this embodiment, because component (A) has an N-hydrocarbyl type hindered amine structure, the range in which the decomposition temperature of component (A) and the non-combustible gas generation temperature of component (B) overlap matches the decomposition temperature range of the synthetic resin, and as a result of synergistically suppressing the combustion reaction of the resin, flame retardancy is improved.
[0016] In addition, the structure in which the hindered amine portion of general formula (1) is positioned at both ends of the linear molecule allows the hindered amine structure to be appropriately dispersed in the synthetic resin, resulting in even better flame retardancy. Furthermore, in particular, when the nitrogen-containing heterocyclic compound (B) is a salt compound, the combustion reaction is suppressed by the endothermic effect of the dissociation reaction of the salt compound, thereby improving flame retardancy.
[0017] R in general formula (1) 1 Preferably, the group is represented by general formula (2) or general formula (3), and more preferably by general formula (2). By selecting these groups, the flame retardant performance of the composition of this embodiment is further improved.
[0018] R in general formula (1) 2 Examples of hydrocarbon groups having 1 to 18 carbon atoms include aliphatic hydrocarbon groups having 1 to 18 carbon atoms or aromatic hydrocarbon groups having 6 to 18 carbon atoms. Examples of aliphatic hydrocarbon groups having 1 to 18 carbon atoms include alkyl groups having 1 to 18 carbon atoms, alkenyl groups having 2 to 18 carbon atoms, and cycloalkyl groups having 3 to 18 carbon atoms.
[0019] Examples of the alkyl groups having 1 to 18 carbon atoms include linear or branched alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, second butyl group, third butyl group, pentyl group, isopentyl group, neopentyl group, third pentyl group, hexyl group, heptyl group, octyl group, isooctyl group, third octyl group, 2-ethylhexyl group, nonyl group, isononyl group, decyl group, isodecyl group, 2-propylheptyl group, undecyl group, dodecyl group, tetradecyl group, hexadecyl group, and octadecyl group.
[0020] Examples of the above-mentioned alkenyl groups having 2 to 18 carbon atoms include linear and cyclic alkenyl groups such as vinyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-pentenyl group, 2-hexenyl group, 3-hexenyl group, 5-hexenyl group, 2-heptenyl group, 3-heptenyl group, 4-heptenyl group, 3-octenyl group, 3-nonenyl group, 4-decenyl group, 3-undecenyl group, 4-dodecenyl group, 3-cyclohexenyl group, 2,5-cyclohexadienyl-1-methyl group, cyclopentadienyl group, or 4,8,12-tetradecatrienylenylallyl group.
[0021] Examples of cycloalkyl groups having 3 to 18 carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclooctadecyl group, 2-bornyl group, 2-isobornyl group, 1-adamantyl group, methylcyclopentyl group, methylcyclohexyl group, dimethylcyclohexyl group, and methylcycloheptyl group.
[0022] Examples of the above-mentioned aromatic hydrocarbon groups having 6 to 18 carbon atoms include phenyl, tolyl, xylyl, cumenyl, mesityl, benzyl, naphthyl, azulenyl, indenyl, indanyl, tetralinyl, phenanthryl, pyrenyl, and biphenylyl groups.
[0023] R in general formula (1) 2 Preferably, it is an alkyl group having 1 to 18 carbon atoms or a cycloalkyl group having 3 to 18 carbon atoms.2 When the alkyl group has 1 to 18 carbon atoms, the alkyl group is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group. 2 When the group is a cycloalkyl group having 3 to 18 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms is preferred, a cycloalkyl group having 5 to 7 carbon atoms is more preferred, and a cyclohexyl group is even more preferred. By selecting these groups, the flame retardant performance of the composition of this embodiment is further improved.
[0024] R in general formula (1) 3 ~R 6 Examples of alkyl groups having 1 to 4 carbon atoms that can be formed include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, and tertiary butyl groups. 3 ~R 6 A methyl group or an ethyl group is preferred, and a methyl group is more preferred. By selecting these groups, the flame retardant performance of the composition of this embodiment is further improved.
[0025] R in general formula (2) 7 and R in general formula (3) 8 Examples of divalent hydrocarbon groups having 1 to 18 carbon atoms include alkylene groups having 1 to 18 carbon atoms, alkenylene groups having 2 to 18 carbon atoms, cycloalkylene groups having 4 to 18 carbon atoms, and arylene groups having 6 to 18 carbon atoms.
[0026] Examples of alkylene groups having 1 to 18 carbon atoms include linear or branched alkylene groups such as methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, isobutylene group, n-pentylene group, isopentylene group, n-hexylene group, isohexylene group, n-heptylene group, isoheptylene group, n-octylene group, isooctylene group, n-nonylene group, isononylene group, n-decylene group, isodecylene group, n-undecylene group, isoundecylene group, n-dodecylene group, isododecylene group, tridecylene group, tetradecylene group, pentadecylene group, hexadecylene group, heptadecylene group, and octadecylene group.
[0027] Examples of the above-mentioned alkenylene groups having 2 to 18 carbon atoms include linear or branched alkenylene groups such as vinylene, 1-methylethenylene, 2-methylethenylene, propenylene, butenylene, isobutenylene, pentenylene, hexenylene, heptenylene, octenylene, decenylene, dodecenylene, tetradecenylene, hexadecenylene, and octadecenylene.
[0028] Examples of the above-mentioned cycloalkylene groups having 4 to 18 carbon atoms include cyclobutylene, cyclopentylene, 2-methylcyclopentylene, cyclohexylene, 1,3-dimethylcyclohexylene, cycloheptylene, 1-ethylcyclopentylene, cyclooctylene, cyclononylene, cyclodecylene, cycloundecylene, cyclododecylene, cyclotriderene, cyclotetradecylene, cyclopentadecylene, cyclohexadecylene, cycloheptadecylene, cyclooctadecylene, norbornylene, dicyclopentylene, isopropylidenedicyclohexylene, and cyclohexanedimethylene.
[0029] Examples of the above-mentioned arylene groups having 6 to 18 carbon atoms include phenylene, torylene, xylylene, naphthylene, biphenylene, phenanthrylene, fluorenylene, indenylene, isopropylidenediphenylene, and dimethylenephenylene groups.
[0030] R in general formula (2) 7 and R in general formula (3) 8 As for the group, a direct bond, an alkylene group having 1 to 18 carbon atoms, or an arylene group having 6 to 18 carbon atoms is preferred, and an alkylene group having 1 to 18 carbon atoms is more preferred. 7 or R 8 When the alkylene group has 1 to 18 carbon atoms, the alkylene group is preferably one with 2 to 14 carbon atoms, more preferably one with 2 to 10 carbon atoms, and even more preferably one with 2 to 6 carbon atoms. 7 or R 8 When the group has 6 to 18 carbon atoms, an arylene group having 6 to 12 carbon atoms is preferred, an arylene group having 6 to 10 carbon atoms is more preferred, and a phenylene group is even more preferred. By selecting these groups, the flame retardant performance of the composition of this embodiment is further improved.
[0031] (A) Specific examples of hindered amine compounds represented by general formula (1) include compounds No. 1 to No. 16 listed below. These compounds may be used individually or in combination of two or more.
[0032] Among these, one or more of compounds No. 2 to No. 13 are preferred due to their excellent flame retardancy, more preferably compounds No. 2, No. 3, No. 4, No. 5, No. 6, No. 8, or No. 9, even more preferably one or more of compounds No. 2 to No. 6, even more preferably one or more of compounds No. 3 to No. 5, and particularly preferred compound No. 3 or No. 4. Furthermore, compounds No. 1, No. 2, No. 3, No. 4, No. 6, No. 7, No. 8, No. 9, No. 10, or No. 14 are preferred due to their solid state at room temperature (e.g., 25°C) and excellent handling properties, and more preferably compounds No. 3, No. 4, or No. 6.
[0033] Conventional known methods can be used to produce the compound represented by general formula (1). For example, a method can be used in which a dicarboxylic acid or dicarboxylic acid derivative containing the structure of general formula (2), a diisocyanate containing the structure of general formula (3), or a carbonate precursor containing the structure of general formula (4) is reacted with an alcohol having an N-hydrocarbyl-2,2,6,6-tetraalkylpiperidinol skeleton. Specifically, direct esterification of an acid and an alcohol, reaction of an acid halide and an alcohol, transesterification reaction, urethane bond formation reaction between an isocyanate and an alcohol, etc., are possible. Alternatively, for example, a dicarboxylic acid or dicarboxylic acid derivative containing the structure of general formula (2), a diisocyanate containing the structure of general formula (3), or a carbonate precursor containing the structure of general formula (4) may be reacted with an alcohol having an N-H-2,2,6,6-tetraalkylpiperidinol skeleton, and then N-hydrocarbylation may be performed using halogenated hydrocarbyl or the like. The compounds obtained by the above methods may be further separated and purified, if necessary, by means of separation and purification such as filtration, concentration, distillation, extraction, crystallization, recrystallization, adsorption, and column chromatography, or by means of a combination thereof.
[0034] (A) As the hindered amine compound represented by general formula (1), one compound may be used alone, R 1 ~R 6 Two or more different compounds may be used in combination.
[0035] The content of the hindered amine compound (A) represented by general formula (1) in the composition of this embodiment is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, even more preferably 1 part by mass or more, even more preferably 2 parts by mass or more, and particularly preferably 3 parts by mass or more, based on 100 parts by mass of the total of components (A) and (B). It is also preferably 30 parts by mass or less, more preferably 15 parts by mass or less, even more preferably 10 parts by mass or less, even more preferably 8 parts by mass or less, and particularly preferably 7 parts by mass or less. The range of the content of component (A) based on 100 parts by mass of the total of components (A) and (B) is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 15 parts by mass, even more preferably 1 to 10 parts by mass, even more preferably 2 to 8 parts by mass, and particularly preferably 3 to 7 parts by mass. With these content levels, the flame retardancy improvement effect by using components (A) and (B) in combination can be sufficiently obtained.
[0036] The content of the hindered amine compound (A) represented by general formula (1) in the composition of this embodiment is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, even more preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, and even more preferably 5 parts by mass or more, per 100 parts by mass of the composition of this embodiment. It is also preferably 30 parts by mass or less, more preferably 15 parts by mass or less, even more preferably 10 parts by mass or less, even more preferably 8 parts by mass or less, and particularly preferably 7 parts by mass or less. The range of the content of component (A) per 100 parts by mass is preferably 0.1 to 30 parts by mass, more preferably 1 to 15 parts by mass, even more preferably 2 to 10 parts by mass, even more preferably 3 to 8 parts by mass, and particularly preferably 5 to 7 parts by mass. With these content levels, the flame retardancy improvement effect by using the combination of component (A) and component (B) can be sufficiently obtained.
[0037] Next, component (B) will be described. The nitrogen-containing heterocyclic compound (B) of the present invention does not have a hindered amine structure and is a compound having a heterocyclic structure containing a nitrogen atom as a heteroatom. In general formula (1), the hindered amine structure is R 2 This refers to the portion sandwiched between oxygen atoms (O). Examples of nitrogen-containing heterocyclic compounds (B) in this embodiment include triazine compounds, piperazine compounds, pyridine compounds, uric acid, adenine, guanine, 2,6-diaminopurine, etc. Examples of the above triazine compounds include melamine salt compounds, as well as triazine, melamine, methylguanamine, cyanuric acid, trimethyltriazine, triphenyltriazine, diaminomethyltriazine, diaminophenyltriazine (benzoguanamine), diaminoisopropoxytriazine, etc. Examples of melamine salt compounds include phosphates, polymerized phosphates, or cyanuric acid (isocyanuric acid) salts of melamine or its deammonocyte condensates, specifically melamine cyanurate, melamine phosphate, melamine pyrophosphate, melamine polyphosphate, and salts of melamine, melam and melam with polyphosphate. Examples of the above piperazine compounds include phosphates and polymerized phosphates of piperazine, preferably piperazine pyrophosphate and piperazine polyphosphate. Examples of the pyridine compounds mentioned above include 2,3-diaminopyridine, 2,5-diaminopyridine, 2,6-diaminopyridine, 3,4-diaminopyridine, and 2,4,6-triaminopyridine.
[0038] (B) Among the nitrogen-containing heterocyclic compounds, triazine compounds and piperazine compounds are preferred in terms of their excellent flame retardancy, and triazine compounds are more preferred. Among the triazine compounds, melamine salt compounds are preferred in terms of their excellent flame retardancy and heat resistance, melamine cyanurate, melamine pyrophosphate, and melamine polyphosphate are more preferred, and melamine cyanurate is even more preferred.
[0039] (B) When the nitrogen-containing heterocyclic compound contains a triazine compound, the proportion of the triazine compound in the nitrogen-containing heterocyclic compound is preferably 60% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, and may be 100% by mass. The preferred proportion of the melamine salt compound in the nitrogen-containing heterocyclic compound and the preferred proportion of the melamine cyanurate in the nitrogen-containing heterocyclic compound are the same lower limits as those listed above for the preferred proportion of the triazine compound in the nitrogen-containing heterocyclic compound.
[0040] The content of the nitrogen-containing heterocyclic compound (B) in the composition of this embodiment is preferably 70 parts by mass or more, more preferably 85 parts by mass or more, even more preferably 90 parts by mass or more, even more preferably 92 parts by mass or more, and particularly preferably 93 parts by mass or more, based on 100 parts by mass of the total of components (A) and (B). It is also preferably 99.9 parts by mass or less, more preferably 99 parts by mass or less, even more preferably 98 parts by mass or less, even more preferably 97 parts by mass or less, and particularly preferably 95 parts by mass or less. The range of the content of component (B) relative to 100 parts by mass of the total of components (A) and (B) is preferably 70 to 99.9 parts by mass, more preferably 85 to 99 parts by mass, even more preferably 90 to 98 parts by mass, even more preferably 92 to 97 parts by mass, and particularly preferably 93 to 95 parts by mass. By including component (B) in these amounts, the flame retardancy improvement effect by using components (A) and (B) together can be sufficiently obtained.
[0041] The content of the nitrogen-containing heterocyclic compound (B) in the composition of this embodiment is preferably 70 parts by mass or more, more preferably 85 parts by mass or more, even more preferably 90 parts by mass or more, even more preferably 92 parts by mass or more, and particularly preferably 93 parts by mass or more, per 100 parts by mass of the composition of this embodiment. It is also preferably 99.9 parts by mass or less, more preferably 99 parts by mass or less, even more preferably 98 parts by mass or less, even more preferably 97 parts by mass or less, and particularly preferably 95 parts by mass or less. The range of the content of component (B) per 100 parts by mass is preferably 70 to 99.9 parts by mass, more preferably 85 to 99 parts by mass, even more preferably 90 to 98 parts by mass, even more preferably 92 to 97 parts by mass, and particularly preferably 93 to 95 parts by mass. With these content levels, the flame retardancy improvement effect by using the combination of component (A) and component (B) can be sufficiently obtained.
[0042] The total content of component (A) and component (B) in the composition of this embodiment is preferably 50 to 100 parts by mass, more preferably 80 to 100 parts by mass, and even more preferably 90 to 100 parts by mass, per 100 parts by mass of the composition of this embodiment. By setting the total content of component (A) and component (B) within the above range, flame retardant performance can be stably exhibited.
[0043] As described above, the composition of this embodiment can impart excellent flame retardancy to synthetic resins, and therefore can be used as a flame retardant for synthetic resins. Furthermore, since the composition of this embodiment can impart particularly excellent flame retardancy to polyolefin resins (sometimes referred to as "polyolefin resins") or styrene resins among synthetic resins, the composition of this embodiment can be suitably used as a flame retardant for polyolefin resins or styrene resins, and is even more suitably used as a flame retardant for polyolefin resins.
[0044] The composition of this embodiment may contain optional components other than components (A) and (B), as long as they do not impair the effects of the present invention. The optional components may be those that may be included in the resin composition of this embodiment, as described later.
[0045] <Resin Composition> The resin composition of this embodiment contains (A) a hindered amine compound represented by general formula (1), (B) a nitrogen-containing heterocyclic compound, and a synthetic resin. The resin composition of this embodiment has excellent color tone and excellent flame retardancy.
[0046] Here, (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound are the same as those exemplified as components contained in the composition of this embodiment described above.
[0047] Examples of synthetic resins include thermoplastic resins such as polyolefin resins, styrene resins, polyester resins, polycarbonate resins, polysulfide resins, polyamide resins, polyether resins, and halogen-containing resins. These may be used individually or in combination of two or more types.
[0048] Furthermore, examples of the synthetic resins mentioned above include petroleum resin, coumarone resin, polyvinyl acetate, acrylic resin, polymethyl methacrylate, polyvinyl alcohol, polyvinyl formal, polyvinyl butyral, polyurethane, cellulose resin, polyimide resin, polysulfone, liquid crystal polymer, and blends thereof.
[0049] Furthermore, the synthetic resin may also be a thermoplastic elastomer such as isoprene rubber, butadiene rubber, ethylene-propylene rubber, ethylene-propylene-diene rubber, acrylonitrile-butadiene copolymer rubber, styrene-butadiene copolymer rubber, olefin-based elastomer, styrene-based elastomer, polyester-based elastomer, nitrile-based elastomer, nylon-based elastomer, vinyl chloride-based elastomer, polyamide-based elastomer, or polyurethane-based elastomer, and may be used in combination.
[0050] Examples of the above-mentioned polyolefin resins include polypropylene, high-density polyethylene, low-density polyethylene, linear low-density polyethylene, polybutene-1, poly-3-methylpentene, poly-4-methylpentene, ethylene / propylene block copolymer, ethylene / propylene random copolymer, and other α-olefin polymers.
[0051] Examples of the styrene-based resins mentioned above include polystyrene (PS), high-impact polystyrene (HIPS), acrylonitrile-styrene copolymer (AS resin), acrylonitrile-butadiene-styrene copolymer (ABS resin), methyl methacrylate-butadiene-styrene copolymer (MBS resin), heat-resistant ABS resin, acrylate-styrene-acrylonitrile copolymer (ASA resin), acrylonitrile-acrylic rubber-styrene copolymer (AAS resin), styrene-maleic anhydride copolymer (SMA resin), methacrylate-styrene copolymer (MS resin), styrene-isoprene-styrene copolymer (SIS resin), acrylonitrile-ethylene propylene rubber-styrene copolymer (AES resin), and styrene-butadiene-styrene copolymer (SBS resin). Examples include styrene monomer-containing resins such as methyl methacrylate-acrylonitrile-butadiene-styrene copolymer (MABS resin), methyl methacrylate-acrylonitrile-styrene copolymer (MAS resin), styrene-IPN type rubber copolymer, and hydrogenated styrene-based elastomer resins such as styrene-ethylene-butylene-styrene copolymer (SEBS resin), styrene-ethylene-propylene-styrene copolymer (SEPS resin), styrene-ethylene-propylene copolymer (SEP resin), styrene-ethylene-ethylene-propylene-styrene copolymer (SEEP resin), styrene-butadiene-butylene-styrene copolymer (SBBS resin), or mixtures thereof, in which the double bonds of butadiene or isoprene are hydrogenated. The styrene-based resin may have stereoregularity, such as atactic polystyrene, isotactic polystyrene, or syndiotactic polystyrene.Examples of the polyester resins mentioned above include polyalkylene terephthalates such as polyethylene terephthalate, polybutylene terephthalate, polytetramethylene terephthalate, and polycyclohexanedimethylene terephthalate; polyalkylene naphthalates such as polyethylene naphthalate and polybutylene naphthalate; and biodegradable aliphatic polyesters such as polyhydroxybutyrate, polycaprolactone, polybutylene succinate, polyethylene succinate, polylactic acid, polymalic acid, polyglycolic acid, polydioxane, and poly(2-oxetanone).
[0052] Examples of the polysulfide resins mentioned above include polyphenylene sulfide. Examples of the polyamide resins mentioned above include polyhexamethylene adipamide. The polycarbonate resins mentioned above are resins having carbonate bonds, and can be obtained, for example, by a polymerization reaction between a divalent hydroxy compound and a carbonate precursor.
[0053] The above divalent hydroxy compounds include dihydroxybenzenes such as resorcinol and hydroquinone; bishydroxyaryl compounds such as 4,4'-dihydroxydiphenyl; bis(hydroxyaryl)alkanes such as bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 1,2-bis(4-hydroxyphenoxy)ethane, and 2,2-bis(4-hydroxyphenyl)propane; dihydroxyaryl ketones such as bis(4-hydroxyphenyl)ketone and bis(4-hydroxy-3-methylphenyl)ketone; dihydroxyaryl ethers such as 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxy-3,3'-dimethylphenyl ether, and 4,4'-dihydroxy-2,5-dihydroxydiphenyl ether; 4 Examples include dihydroxyaryl sulfur compounds such as ,4'-thiodiphenol, bis(4-hydroxyphenyl) sulfide, 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfide, 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfoxide, 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfoxide, 2,2-bis(4-hydroxyphenyl) sulfone, 4,4'-dihydroxydiphenyl sulfone, and 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfone; phenolphthalein; aliphatic diols such as 1,3-propanediol, 1,4-butanediol, and 1,6-hexanediol; and alicyclic diols such as 1,4-cyclohexanedimethanol, 1,4-cyclohexanediol, and hydrogenated bisphenol A. These may be used individually or in combination of two or more, and may also be used in combination with polyvalent hydroxy compounds having three or more hydroxyl groups.
[0054] Suitable specific examples of the above-mentioned carbonate precursor include phosgene, diester carbonate, dihaloformates of divalent phenols, and mixtures thereof.
[0055] From the viewpoint of exhibiting flame retardant performance more effectively, the synthetic resin preferably contains a polyolefin resin or a styrene resin, more preferably contains a polyolefin resin, even more preferably is mainly polyolefin resin (70% by mass or more of the synthetic resin, particularly preferably 90% by mass or more), and even more preferably consists only of polyolefin resin. Among polyolefin resins, from the viewpoint of exhibiting flame retardant performance more effectively, polypropylene, high-density polyethylene, low-density polyethylene, linear low-density polyethylene, ethylene / propylene block copolymer, and ethylene / propylene random copolymer are preferred, polypropylene, high-density polyethylene, low-density polyethylene, and linear low-density polyethylene are more preferred, and low-density polyethylene and linear low-density polyethylene are even more preferred.
[0056] These synthetic resins can be used regardless of molecular weight, degree of polymerization, polymerization method, density, softening point, proportion of insoluble matter in the solvent, degree of stereoregularity, presence or absence of catalyst residue, type and blending ratio of raw material monomers, type of polymerization catalyst, etc. These synthetic resins may be used individually or in combination of two or more types. Furthermore, the synthetic resins may be alloyed.
[0057] The content of the hindered amine compound (A) represented by general formula (1) in the resin composition of this embodiment is preferably 0.1 parts by mass or more, more preferably 0.3 parts by mass or more, even more preferably 0.5 parts by mass or more, even more preferably 0.8 parts by mass or more, and particularly preferably 1 part by mass or more, per 100 parts by mass of synthetic resin. It is also preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, even more preferably 2 parts by mass or less, and particularly preferably 1.4 parts by mass or less. The range of the content of component (A) per 100 parts by mass of synthetic resin is preferably 0.1 to 10 parts by mass, more preferably 0.3 to 5 parts by mass, even more preferably 0.5 to 3 parts by mass, even more preferably 0.8 to 2 parts by mass, and particularly preferably 1 to 1.4 parts by mass. With these content levels, the flame retardant performance of component (A) can be fully exhibited, and the bleeding of component (A) is reduced.
[0058] The content of the nitrogen-containing heterocyclic compound (B) in the resin composition of this embodiment is preferably 5 to 100 parts by mass, more preferably 10 to 50 parts by mass, even more preferably 12 to 30 parts by mass, even more preferably 15 to 26 parts by mass, and particularly preferably 17 to 23 parts by mass, per 100 parts by mass of the synthetic resin. With these content levels, the flame retardant performance of component (B) can be fully exhibited, and the deterioration of the mechanical properties of the resin composition can be suppressed.
[0059] Furthermore, the content of the nitrogen-containing heterocyclic compound (B) in the resin composition of this embodiment is preferably 70 parts by mass or more, more preferably 85 parts by mass or more, even more preferably 90 parts by mass or more, even more preferably 92 parts by mass or more, and particularly preferably 93 parts by mass or more, based on 100 parts by mass of the total of components (A) and (B). Also, it is preferably 99.9 parts by mass or less, more preferably 99 parts by mass or less, even more preferably 98 parts by mass or less, even more preferably 97 parts by mass or less, and particularly preferably 95 parts by mass or less. The range of the content of component (B) in the resin composition based on 100 parts by mass of the total of components (A) and (B) is preferably 70 to 99.9 parts by mass, more preferably 85 to 99 parts by mass, even more preferably 90 to 98 parts by mass, even more preferably 92 to 97 parts by mass, and particularly preferably 93 to 95 parts by mass. With these content levels, the flame retardancy improvement effect by using components (A) and (B) in combination can be sufficiently obtained.
[0060] The total content of (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound in the resin composition of this embodiment is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, even more preferably 14 parts by mass or more, even more preferably 16 parts by mass or more, and particularly preferably 18 parts by mass or more, per 100 parts by mass of synthetic resin. Alternatively, it is preferably 50 parts by mass or less, more preferably 40 parts by mass or less, even more preferably 33 parts by mass or less, even more preferably 28 parts by mass or less, and particularly preferably 24 parts by mass or less. The range of the total content of component (A) and component (B) per 100 parts by mass of synthetic resin is preferably 5 to 50 parts by mass, more preferably 10 to 40 parts by mass, even more preferably 14 to 33 parts by mass, even more preferably 16 to 28 parts by mass, and particularly preferably 18 to 24 parts by mass. These content levels allow for a good balance between the inherent physical properties of the resin and flame retardant performance.
[0061] The total content of (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound in the resin composition of this embodiment is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, even more preferably 12 parts by mass or more, even more preferably 13 parts by mass or more, and particularly preferably 14 parts by mass or more, per 100 parts by mass of the resin composition of this embodiment. It is also preferably 35 parts by mass or less, more preferably 27 parts by mass or less, even more preferably 23 parts by mass or less, even more preferably 19 parts by mass or less, and particularly preferably 17 parts by mass or less. The range of the total content of component (A) and component (B) per 100 parts by mass of the resin composition is preferably 5 to 35 parts by mass, more preferably 10 to 27 parts by mass, even more preferably 12 to 23 parts by mass, even more preferably 13 to 19 parts by mass, and particularly preferably 14 to 17 parts by mass. With these content levels, the inherent physical properties of the resin and flame retardant performance can be exhibited in a well-balanced manner.
[0062] The synthetic resin content in the resin composition of this embodiment is preferably 50 parts by mass or more, more preferably 65 parts by mass or more, even more preferably 70 parts by mass or more, even more preferably 75 parts by mass or more, and particularly preferably 80 parts by mass or more, per 100 parts by mass of the resin composition of this embodiment. It is also preferably 99 parts by mass or less, more preferably 95 parts by mass or less, even more preferably 90 parts by mass or less, even more preferably 88 parts by mass or less, and particularly preferably 85 parts by mass or less. The range of synthetic resin content per 100 parts by mass of the resin composition is preferably 50 to 99 parts by mass, more preferably 65 to 95 parts by mass, even more preferably 70 to 90 parts by mass, even more preferably 75 to 88 parts by mass, and particularly preferably 80 to 85 parts by mass. With these content levels, the mechanical properties and flame retardant performance of the resin composition can be exhibited in a well-balanced manner.
[0063] The resin composition of this embodiment may contain (A) a hindered amine compound represented by general formula (1), (B) a nitrogen-containing heterocyclic compound, and any other components besides the synthetic resin. The following describes the optional components that the resin composition of this embodiment may contain.
[0064] Optional components that may be included in the resin composition of this embodiment include phenolic antioxidants, phosphorus antioxidants, thioether antioxidants, ultraviolet absorbers, hindered amine light stabilizers other than component (A) of this embodiment, crosslinking agents, antistatic agents, antifogging agents, plate-out inhibitors, surface treatment agents, plasticizers, lubricants, reinforcing agents, nucleating agents, flame retardants, flame retardant aids, fluorescent agents, antifungal agents, bactericides, foaming agents, metal deactivators, mold release agents, silicone oils, silane coupling agents, fillers, hydrotalcites, metal soaps, pigments, dyes, and other additives commonly used in synthetic resins, provided they do not contain component (A) or component (B). The content of these optional components can be within a range that does not impair the effects of this embodiment.
[0065] The resin composition of this embodiment preferably contains, if necessary, one or more selected from the group consisting of phenolic antioxidants, phosphorus-based antioxidants, thioether-based antioxidants, ultraviolet absorbers, and hindered amine-based light stabilizers other than component (A) of this embodiment. Here, the content of these components can be, for example, an amount that does not impair the effects of this embodiment.
[0066] Examples of phenolic antioxidants include 2,6-di-tert-butyl p-cresol, 2,6-diphenyl-4-octadecyloxyphenol, distearyl(3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 1,6-hexamethylenebis[(3,5-di-tert-butyl-4-hydroxyphenyl)propionamide], 4,4'-thiobis(6-tert-butyl-m-cresol), 2,2'-methylenebis(4-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-ethyl-6-tert-butylphenol), 4,4 '-Butylidenebis(6-tertiary butyl-m-cresol), 2,2'-Ethylidenebis(4,6-di-tertiary butylphenol), 2,2'-Ethylidenebis(4-secondary butyl-6-tertiary butylphenol), 1,1,3-Tris(2-methyl-4-hydroxy-5-tertiary butylphenyl)butane, 1,3,5-Tris(2,6-dimethyl-3-hydroxy-4-tertiary butylbenzyl) isocyanurate, 1,3,5-Tris(3,5-di-tertiary butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-Tris(3,5-di-tertiary butyl-4- Hydroxybenzyl)-2,4,6-trimethylbenzene, 2-tert-butyl-4-methyl-6-(2-acryloyloxy-3-tert-butyl-5-methylbenzyl)phenol, stearyl(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate methyl]methane, thiodiethylene glycol bis[(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 1,6-hexamethylene bis[(3,5-di-tert-butyl-4-hydroxyphenyl) [Ciphenyl)propionate], bis[3,3-bis(4-hydroxy-3-tertiary butylphenyl)butyric acid] glycol ester, bis[2-tertiary butyl-4-methyl-6-(2-hydroxy-3-tertiary butyl-5-methylbenzyl)phenyl] terephthalate, 1,3,5-tris[(3,5-di-tertiary butyl-4-hydroxyphenyl)propionyloxyethyl] isocyanurate, 3,9-bis[1,1-dimethyl-2-{(3-tertiary butyl-4-hydroxy-5-methylphenyl)propionyloxy}ethyl]-2,4,8,Examples include 10-tetraoxaspiro[5,5]undecane and triethylene glycol bis[(3-tertiary butyl-4-hydroxy-5-methylphenyl)propionate]. These phenolic antioxidants may be used individually or in combination of two or more. The content of the phenolic antioxidant is preferably 0.001 to 10 parts by mass, and more preferably 0.05 to 5 parts by mass, per 100 parts by mass of synthetic resin, from the viewpoint of excellent antioxidant effect.
[0067] Examples of phosphorus-based antioxidants include tris(2,4-di-tert-butylphenyl) phosphite, trisnonylphenyl phosphite, tris[2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenylthio)-5-methylphenyl] phosphite, tridecyl phosphite, octyldiphenyl phosphite, didecylmonophenyl phosphite, bis(tridecyl)pentaerythritol diphosphite, and bis(nonylphenyl)pentaerythritol Diphosphate, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphate, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphate, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphate, bis(2,4-dicumylphenyl)pentaerythritol diphosphate, tetrakis(tridecyl)isopropylidene diphenol diphosphate, tetrakis(tridecyl)-4,4 '-n-butylidenebis(2-tertiary butyl-5-methylphenol) diphosphite, hexakis(tridecyl)-1,1,3-tris(2-methyl-4-hydroxy-5-tertiary butylphenyl)butane triphosphite, tetrakis(2,4-di-tertiary butylphenyl) biphenylenediphosphonite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 2,2'-methylenebis(4,6-tertiary butylphenyl)-2-ethylhexyl phosphate Examples include sphite, 2,2'-methylenebis(4,6-tertiary butylphenyl)-octadecyl phosphite, 2,2'-ethylidenebis(4,6-di-tertiary butylphenyl) fluorophosphite, tris(2-[(2,4,8,10-tetrakis-tertiary butyldibenzo[d,f][1,3,2]dioxaphosphine-6-yl)oxy]ethyl)amine, and phosphites of 2-ethyl-2-butylpropylene glycol and 2,4,6-tri-tertiary butylphenol. These phosphorus-based antioxidants may be used individually or in combination of two or more. The amount of phosphorus-based antioxidant is preferably 0.001 to 10 parts by mass, and more preferably 0.05 to 5 parts by mass, per 100 parts by mass of synthetic resin, from the viewpoint of excellent antioxidant effect.
[0068] Examples of thioether-based antioxidants include dialkylthiodipropionates such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate, and pentaerythritol tetrakis (β-alkyl mercaptopropionates). These thioether-based antioxidants may be used individually or in combination of two or more. The content of the thioether-based antioxidant is preferably 0.001 to 10 parts by mass, and more preferably 0.05 to 5 parts by mass, per 100 parts by mass of the synthetic resin, in order to obtain excellent antioxidant effects.
[0069] Examples of UV absorbers include 2-hydroxybenzophenones such as 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, and 5,5'-methylenebis(2-hydroxy-4-methoxybenzophenone); 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-di-tertiary butylphenyl)-5-chlorobenzotriazole, and 2-(2'-hydroxy-3'-di-tertiary butylphenyl). 2-(2'-hydroxyphenyl)benzotriazoles such as tributyl-5'-methylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-tertiary octylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-dicumylphenyl)benzotriazole, 2,2'-methylenebis(4-tertiary octyl-6-(benzotriazolyl)phenol), and 2-(2'-hydroxy-3'-tertiary butyl-5'-carboxyphenyl)benzotriazole; phenyl salicylate Benzoates such as resorcinol monobenzoate, 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, 2,4-di-tert-amylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate; substituted oxanilides such as 2-ethyl-2'-ethoxyoxanilide and 2-ethoxy-4'-dodecyloxanilide; ethyl-α-cyano-β,β-diphenyl acrylate, methyl Examples include cyanoacrylates such as 2-2-cyano-3-methyl-3-(p-methoxyphenyl)acrylate; and triaryltriazines such as 2-(2-hydroxy-4-octoxyphenyl)-4,6-bis(2,4-di-tert-butylphenyl)-s-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-s-triazine, and 2-(2-hydroxy-4-propoxy-5-methylphenyl)-4,6-bis(2,4-di-tert-butylphenyl)-s-triazine. These ultraviolet absorbers may be used individually or in combination of two or more.The amount of ultraviolet absorber is preferably 0.001 to 30 parts by mass, and more preferably 0.05 to 10 parts by mass, per 100 parts by mass of synthetic resin, in order to obtain an excellent ultraviolet absorption effect.
[0070] Examples of hindered amine-based light stabilizers other than component (A) of this embodiment include 2,2,6,6-tetramethyl-4-piperidyl stearate, 1,2,2,6,6-pentamethyl-4-piperidyl stearate, 2,2,6,6-tetramethyl-4-piperidyl benzoate, bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, and tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)-1,2,3,4 -Butanetetracarboxylate, bis(2,2,6,6-tetramethyl-4-piperidyl)・bis(tridecyl)-1,2,3,4-butanetetracarboxylate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)・bis(tridecyl)-1,2,3,4-butanetetracarboxylate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)-2-butyl-2-(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol / sucrose Diethyl acid polycondensate, 1,6-bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane / 2,4-dichloro-6-morpholino-s-triazine polycondensate, 1,6-bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane / 2,4-dichloro-6-tertioctylamino-s-triazine polycondensate, 1,5,8,12-tetrakis[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-s-triazine-6-yl]-1,5,8,12-tetraazadodecane, 1,5,8,12- Tetrakis[2,4-bis(N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino)-s-triazine-6-yl]-1,5,8-12-tetraazadodecane, 1,6,11-tris[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-s-triazine-6-yl]aminoundecane, 1,6,11-tris[2,4-bis(N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino)-s-triazine-6-yl]aminoundecane, bis(2,2,6,Examples include 6-tetramethyl-1-octyloxy-4-piperidyl)decandioate, bis(2,2,6,6-tetramethyl-1-undecyloxypiperidine-4-yl) carbonate, and BASF's TINUVIN NOR 371. These hindered amine light stabilizers may be used individually or in combination of two or more. The content of the hindered amine light stabilizer is preferably 0.001 to 30 parts by mass, and more preferably 0.05 to 10 parts by mass, per 100 parts by mass of synthetic resin, from the standpoint of excellent light stabilization effect.
[0071] Since the phosphonic acid ester represented by the following formula (5) may be hygroscopic, the fluidity of the composition containing the phosphonic acid ester may deteriorate, and bridging may occur in the hopper or feeder of a processing machine such as an extruder. For this reason, it is preferable that the composition of this embodiment is substantially free of the phosphonic acid ester represented by the following formula (5). Substantially free means that it is less than 10% by mass in the composition of this embodiment, and may be less than 5% by mass, less than 2% by mass, less than 1% by mass, less than 0.1% by mass, or 0% by mass. From the same viewpoint as above, it is preferable that the resin composition of this embodiment is substantially free of the phosphonic acid ester. Substantially free means that it is less than 0.1% by mass in the resin composition of this embodiment, and may be less than 0.09% by mass, less than 0.09% by mass, or 0% by mass. In the formula, R1 and R2 are independently selected from the group consisting of alkyl groups, benzyl groups, phenyl groups, naphthyl groups, and naphthyl groups. The alkyl groups, benzyl groups, phenyl groups, and naphthyl groups may be substituted. Examples of substituents on the benzyl groups, phenyl groups, and naphthyl groups include halogen atoms (fluorine, bromine, chlorine, iodine), nitro groups, cyano groups, hydroxyl groups, amino groups, carboxyl groups, alkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms. Examples of substituents on substituted alkyl groups include halogen atoms (fluorine, bromine, chlorine, iodine), nitro groups, cyano groups, hydroxyl groups, amino groups, and carboxyl groups. The number of carbon atoms in the alkyl groups represented by R1 and R2 may be 1 to 30 or 1 to 10.
[0072] The form of the resin composition of this embodiment is not particularly limited, but from the viewpoint of handling the resin composition, it is preferably in the form of pellets, powder, granules, or flakes, and more preferably in the form of pellets. Furthermore, the resin composition of this embodiment can be used as a masterbatch to be blended into resin compositions other than the resin composition of this embodiment.
[0073] <Method for producing the resin composition> The method for producing the resin composition of this embodiment includes a compounding step of blending a synthetic resin with (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound. According to the method for producing the resin composition of this embodiment, a resin composition having excellent flame retardancy can be produced.
[0074] In the compounding process, any of the above-mentioned optional components may be added as components that may be contained in the resin composition of this embodiment.
[0075] There are no particular limitations on the method of compounding a synthetic resin with (A) a hindered amine compound represented by general formula (1), (B) a nitrogen-containing heterocyclic compound, and any other component. For example, two or more components selected from (A) a hindered amine compound represented by general formula (1), (B) a nitrogen-containing heterocyclic compound, and any other component may be mixed in advance before being compounded into the synthetic resin, or each component other than the synthetic resin may be compounded sequentially into the synthetic resin. When multiple components are mixed in advance, each component may be pulverized before mixing, or mixed first and then pulverized. If the synthetic resin is an alloy, each component other than the synthetic resin may be added to a compound that is already an alloy, or it may be added during the alloying process of the synthetic resin.
[0076] Furthermore, as a method for blending (A) a hindered amine compound represented by general formula (1), (B) a nitrogen-containing heterocyclic compound, and an optional component into a synthetic resin, a masterbatch may be prepared by first blending a portion of the synthetic resin with (A) a hindered amine compound represented by general formula (1), (B) a nitrogen-containing heterocyclic compound, and an optional component, and then blending the masterbatch into the remaining synthetic resin.
[0077] <Molded Articles> These molded articles are obtained from the resin composition of this embodiment. The molded articles of this embodiment have excellent color tone and excellent flame retardancy.
[0078] The molding method for the molded product is not particularly limited, and examples include extrusion molding, calendering, injection molding, roll molding, compression molding, and blow molding. These molding methods can be used to manufacture molded products of various shapes, such as resin plates, sheets, films, pellets, and irregularly shaped products. Furthermore, the molded products of this embodiment can be used in a wide range of industrial fields, including electrical / electronic / telecommunications, agriculture / forestry / fisheries, mining, construction, food, textiles, clothing, medical, coal, petroleum, rubber, leather, automobiles, precision instruments, timber, building materials, civil engineering, furniture, printing, and musical instruments. More specifically, it is used in office automation equipment such as printers, personal computers, word processors, keyboards, PDAs (Personal Digital Assistants), telephones, photocopiers, facsimile machines, ECRs (Electronic Cash Registers), calculators, electronic organizers, cards, holders, and stationery; home appliances such as washing machines, refrigerators, vacuum cleaners, microwave ovens, lighting fixtures, game consoles, irons, and heated tables; AV equipment such as TVs, VTRs, video cameras, boomboxes, tape recorders, MiniDiscs, CD players, speakers, and LCD displays; electrical and electronic components such as connectors, relays, capacitors, switches, printed circuit boards, coil bobbins, semiconductor encapsulation materials, LED encapsulation materials, electric wires, cables, transformers, deflection yokes, distribution boards, and clocks, as well as communication equipment.
[0079] Furthermore, the molded product of this embodiment can be used in optical material applications such as optical discs, CD discs, DVD discs, and lenses, as well as in glass substitute applications. Furthermore, the molded products of this embodiment can be used in a variety of applications, including seats (filling, upholstery, etc.), belts, headliners, convertible tops, armrests, door trims, rear package trays, carpets, mats, sun visors, wheel covers, mattress covers, airbags, insulating materials, handrails, handrail straps, wire insulation materials, electrical insulating materials, paints, coatings, upholstery materials, flooring materials, bulkheads, carpets, wallpaper, wall coverings, exterior materials, interior materials, roofing materials, decking materials, wall materials, column materials, baseboards, fence materials, frameworks and moldings, window and door profiles, shingles, paneling, terraces, balconies, soundproofing boards, heat insulating boards, window materials, etc., as well as civil engineering materials, clothing, curtains, sheets, plywood, synthetic fiberboards, carpets, doormats, sheets, buckets, hoses, containers, eyeglasses, bags, cases, goggles, skis, rackets, tents, musical instruments, and other everyday goods and sports equipment.
[0080] <Method for making synthetic resins flame-retardant> The method for making synthetic resins flame-retardant according to this embodiment involves blending the synthetic resin with (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound. According to the method for making synthetic resins flame-retardant according to this embodiment, excellent flame retardancy can be imparted to the synthetic resin without degrading its color.
[0081] <Additives> The additive of this embodiment is an additive for preparing a composition containing (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound, wherein (A) contains the hindered amine compound represented by general formula (1). The additive of this embodiment may consist of (A) the hindered amine compound represented by general formula (1), or it may consist of (A) the hindered amine compound represented by general formula (1), or it may contain components other than the hindered amine compound represented by general formula (1). The proportion of the hindered amine compound represented by general formula (1) in the additive is preferably 70% by mass or more, and more preferably 90% by mass or more. Component other than the hindered amine compound represented by general formula (1) in the additive is an optional component that may be contained in the resin composition of this embodiment as described above. A composition using the additive of this embodiment can impart excellent flame retardancy to a synthetic resin without degrading the color tone of the synthetic resin.
[0082] The following embodiments are included in this disclosure: [1] A composition comprising (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound. In general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. R in general formula (2) 7 and R in general formula (3) 8 * represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
[0083] [2] R in general formula (1) 1 The composition according to [1], wherein is a group represented by general formula (2).
[0084] [3] R in general formula (2) 7 The composition according to [1] or [2], wherein is an alkylene group having 2 to 14 carbon atoms.
[0085] [4] R in general formula (2) 7 The composition according to [1] or [2], wherein is an alkylene group having 2 to 6 carbon atoms.
[0086] [5] (A) The composition according to [1], wherein the hindered amine compound represented by general formula (1) is one or more selected from the following compounds No. 2 to No. 13.
[0087] [6] (A) The composition according to [1], wherein the hindered amine compound represented by general formula (1) is one or more selected from compounds No. 2 to No. 13, preferably compounds No. 2, No. 3, No. 4, No. 5, No. 6, No. 8 or No. 9, more preferably one or more selected from compounds No. 2 to No. 6, even more preferably one or more selected from compounds No. 2 to No. 5, even more preferably one or more selected from compounds No. 3 to No. 5, even more preferably one or more selected from compounds No. 3 or No. 4, and particularly preferably compound No. 3.
[0088] [7] (B) The composition according to any one of [1] to [6], wherein the nitrogen-containing heterocyclic compound is one or more selected from triazine compounds and piperazine compounds, preferably triazine compounds.
[0089] [8] (B) The composition according to any one of [1] to [6], wherein the nitrogen-containing heterocyclic compound is one or more selected from melamine cyanurate, piperazine pyrophosphate, and piperazine polyphosphate, preferably melamine cyanurate.
[0090] [9] The composition according to any one of [1] to [8], wherein the content of (B) nitrogen-containing heterocyclic compound is 70 to 99.9 parts by mass, preferably 85 to 99 parts by mass, more preferably 90 to 98 parts by mass, even more preferably 92 to 97 parts by mass, and even more preferably 93 to 95 parts by mass, based on 100 parts by mass of the total of (A) hindered amine compound represented by general formula (1) and (B) nitrogen-containing heterocyclic compound.
[0091]
[10] A flame retardant, the composition according to any one of items [1] to [9].
[0092]
[11] A composition according to any one of [1] to [9], which is a flame retardant for synthetic resins.
[0093]
[12] A composition according to any one of [1] to [9], which is a flame retardant for polyolefin resins or a flame retardant for styrene resins, preferably a flame retardant for polyolefin resins.
[0094]
[13] A resin composition comprising (A) a hindered amine compound represented by general formula (1), (B) a nitrogen-containing heterocyclic compound, and a synthetic resin. In general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. R in general formula (2) 7 and R in general formula (3) 8 * represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
[0095]
[14] R in general formula (1) 1 The resin composition according to
[13] , wherein is a group represented by general formula (2).
[0096]
[15] R in general formula (2) 7is an alkylene group having 2 to 14 carbon atoms, the resin composition according to
[13] or
[14] .
[0097]
[16] R in general formula (2) 7 is an alkylene group having 2 to 6 carbon atoms, the resin composition according to
[13] or
[14] .
[0098]
[17] The resin composition according to
[13] , wherein (A) the hindered amine compound represented by general formula (1) is one or more selected from Compound No. 2 to Compound No. 13 below.
[0099]
[18] The resin composition according to
[13] , wherein (A) the hindered amine compound represented by general formula (1) is one or more selected from Compound No. 2 to Compound No. 13, preferably one or more selected from Compound No. 2, Compound No. 3, Compound No. 4, Compound No. 5, Compound No. 6, Compound No. 8 or Compound No. 9, more preferably one or more selected from Compound No. 2 to Compound No. 6, still more preferably one or more selected from Compound No. 2 to Compound No. 5, even still more preferably one or more selected from Compound No. 3 to Compound No. 5, further even still more preferably one or more selected from Compound No. 3 or Compound No. 4, and particularly preferably Compound No. 3.
[0100]
[19] The resin composition according to any one of
[13] to
[18] , wherein (B) the nitrogen-containing heterocyclic compound is one or more selected from a triazine compound and a piperazine compound, and is preferably a triazine compound.
[0101]
[20] The resin composition according to any one of
[13] to
[18] , wherein (B) the nitrogen-containing heterocyclic compound is one or more selected from melamine cyanurate, piperazine pyrophosphate, and piperazine polyphosphate, and is preferably melamine cyanurate.
[0102]
[21] The resin composition according to any one of
[13] to
[20] , wherein the synthetic resin comprises a polyolefin resin or a styrene resin, and preferably comprises a polyolefin resin.
[0103]
[22] The resin composition according to any one of
[13] to
[20] , wherein the synthetic resin consists only of a polyolefin resin.
[0104]
[23] The resin composition according to either one of
[21] or
[22] , wherein the polyolefin resin is one or more selected from the group consisting of polypropylene, high-density polyethylene, low-density polyethylene, linear low-density polyethylene, ethylene / propylene block copolymer and ethylene / propylene random copolymer, preferably one or more selected from the group consisting of polypropylene, high-density polyethylene, low-density polyethylene and linear low-density polyethylene, more preferably one or more selected from low-density polyethylene and linear low-density polyethylene.
[0105]
[24] (A) The resin composition according to any one of
[13] to
[23] , wherein the content of the hindered amine compound represented by general formula (1) is 0.1 to 10 parts by mass, preferably 0.3 to 5 parts by mass, more preferably 0.5 to 3 parts by mass, even more preferably 0.8 to 2 parts by mass, and even more preferably 1 to 1.4 parts by mass, per 100 parts by mass of the synthetic resin.
[0106]
[25] (B) The resin composition according to any one of
[13] to
[24] , wherein the content of the nitrogen-containing heterocyclic compound is 5 to 100 parts by mass, preferably 10 to 50 parts by mass, more preferably 12 to 30 parts by mass, even more preferably 15 to 26 parts by mass, and even more preferably 17 to 23 parts by mass, per 100 parts by mass of the synthetic resin.
[0107]
[26] The resin composition according to any one of
[13] to
[25] , wherein the content of (B) nitrogen-containing heterocyclic compound is 70 to 99.9 parts by mass, preferably 85 to 99 parts by mass, more preferably 90 to 98 parts by mass, even more preferably 92 to 97 parts by mass, and even more preferably 93 to 95 parts by mass, based on 100 parts by mass of the total of (A) hindered amine compound represented by general formula (1) and (B) nitrogen-containing heterocyclic compound.
[0108]
[27] The resin composition according to any one of
[13] to
[26] , wherein the total content of (A) the hindered amine compound represented by general formula (1) and (B) the nitrogen-containing heterocyclic compound is 5 to 50 parts by mass, preferably 10 to 40 parts by mass, more preferably 14 to 33 parts by mass, still more preferably 16 to 28 parts by mass, and even more preferably 18 to 24 parts by mass, relative to 100 parts by mass of the synthetic resin.
[0109]
[28] A molded article obtained from the resin composition according to any one of
[13] to
[27] .
[0110]
[29] A method for producing a resin composition, comprising a blending step of blending (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound into a synthetic resin. In general formula (1), R 1 represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), and R 2 represents a hydrocarbon group having 1 to 18 carbon atoms, and R 3 , R 4 , R 5 and R 6 each independently represent an alkyl group having 1 to 4 carbon atoms. In general formula (2), R 7 and R in general formula (3) 8 represent a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formula (2), general formula (3), and formula (4), * represents a bonding site.
[0111]
[30] A method for flame-retarding a synthetic resin, comprising blending (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound into the synthetic resin. In general formula (1), R 1 represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), and R 2 represents a hydrocarbon group having 1 to 18 carbon atoms, and R 3 , R 4 , R 5 and R 6 each independently represent an alkyl group having 1 to 4 carbon atoms. In general formula (2), R7 and R in general formula (3) 8 * represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
[0112]
[31] An additive for preparing a composition comprising (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound, wherein the additive comprises (A) a hindered amine compound represented by general formula (1). In general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. R in general formula (2) 7 and R in general formula (3) 8 * represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
[0113]
[32] Use of an additive containing (A) a hindered amine compound represented by general formula (1) in a composition containing (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound. In general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. R in general formula (2) 7 and R in general formula (3) 8* represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
[0114] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto.
[0115] The details of the components in Tables 1 and 2 are shown below. LLDPE: Linear low-density polyethylene resin (product name: UR952G, manufactured by Nippon Polyethylene Co., Ltd., MFR = 5 g / 10 min (JIS K 6922-1, 190℃ / 2.16 kg)) (A)-1: Compound No. 2 (A)-2: Compound No. 3 (A)-3: Compound No. 5 (A)-X1: Bis(2,2,6,6-tetramethylpiperidyl)sebacate (B)-1: Melamine cyanurate antioxidant 1: Stearyl (3,5-di-tert-butyl-4-hydroxyphenyl)propionate antioxidant 2: Tris(2,4-di-tert-butylphenyl) phosphite
[0116] <Preparation of Test Specimens> Based on the mixing amounts listed in Tables 1 and 2, components (A) and (B) were uniformly mixed to obtain a composition. The composition thus obtained was mixed with each component other than components (A) and (B), and the mixture was melt-kneaded at a melting temperature of 200°C and a screw speed of 30 rpm using a device consisting of a Laboplast Mill μ manufactured by Toyo Seiki Seisakusho connected to a twin-screw extruder (product name: 2D15W) to obtain a resin strand. The obtained resin strand was cut with a pelletizer to obtain a pelletized composition. A cast film with a thickness of 200 μm was prepared using the pelletized composition obtained above. Film preparation was carried out using a device consisting of a Lab Plast Mill μ manufactured by Toyo Seiki Seisakusho Co., Ltd., connected to a single-screw extruder (product name: D1220B) and a T-die (product name: MT60B). The conditions were: melting temperature 200°C, screw speed 30 rpm, T-die extrusion temperature 200°C, chill roll temperature 60°C, and roll rotation speed 0.40–0.45 rpm. From the obtained film, 20 cm × 5 cm test pieces for flame retardancy evaluation and dumbbell-shaped test pieces (type 5) conforming to JIS K7127 for mechanical property evaluation were cut out and left to stand for 48 hours at 23±2°C and 50±5% RH.
[0117] <Flame Retardancy Evaluation: UL-94VTM> The test specimen prepared above was rolled into a cylindrical shape so that the lower ends did not overlap, and the lower end of the sample was held vertically 10 mm above the burner. A Bunsen burner with an inner diameter of 9.5 mm and a flame length of 20 mm was used as the heat source, and the lower end of the test specimen was exposed to the flame for 3 seconds, after which the burning time was measured. After the flame extinguished, the flame was exposed again for 3 seconds, and the burning time was measured again. Flame retardancy was evaluated according to the evaluation criteria of VTM-0, VTM-1, and VTM-2, and the rank of the test specimen that met the lowest criterion out of n=5 measurements was taken as the evaluation rank of the resin composition. Those that did not fall into any of the ranks from VTM-0 to VTM-2 were marked as "Not VTM". The results are shown in Table 1.
[0118] <Color Tone Evaluation: Yellowness> The cast film obtained above was cut to a size of 50 mm x 50 mm, and the yellowness (Y.I.) was measured using a multi-light source spectrophotometer (X-rite ColorEye 7000A). A higher yellowness value indicates a stronger yellow tint and inferior color tone. The evaluation results are shown in Table 1.
[0119] <Mechanical Properties Evaluation: Tensile Elongation> The dumbbell-shaped test specimens (Type 5) obtained above in accordance with JIS K7127 were subjected to tensile testing using a tensile testing machine (Shimadzu Autograph AGS-X) under the condition of a tensile speed of 100 mm / min in accordance with JIS K7127, and the tensile elongation value (%) was measured. The evaluation results are shown in Table 2.
[0120]
[0121]
[0122] Table 1 shows the evaluation results for flame retardancy. For compositions containing components (A) and (B) (Examples 1-8), the UL-94V flammability rank was VTM-2. This was an improvement in the UL-94V flammability rank compared to compositions without components (A) and (B) (Comparative Example 1), compositions containing only one of components (A) or (B) (Comparative Examples 2-8), and compositions using a hindered amine compound with a different structure from component (A) in combination with component (B) (Comparative Examples 9-11). This indicates that incorporating components (A) and (B) into the synthetic resin imparts excellent flame retardancy to the resin. Furthermore, the resin compositions of Examples 1-8 had low yellowness (Y.I.) values. Therefore, it was demonstrated that compositions containing components (A) and (B) can impart excellent flame retardancy to synthetic resins without increasing their yellowness.
[0123] Table 2 shows the evaluation results for tensile elongation as an evaluation of mechanical properties. From the evaluation results shown in Table 2, it can be seen that the tensile elongation tends to decrease as the amount of component (B) added increases. However, the compositions containing both component (A) and component (B) (Examples 2, 4, and 6) had higher tensile elongation values compared to compositions containing only component (B) (Comparative Examples 2 to 4). Therefore, it was shown that compositions containing both component (A) and component (B) can effectively suppress the deterioration of the mechanical properties of the synthetic resin.
[0124] From the above results, it was confirmed that the composition of this embodiment can impart excellent flame retardancy to synthetic resins without increasing their yellowness.
[0125] According to the present invention, it is possible to provide a composition that imparts excellent flame retardancy to a synthetic resin without degrading its color tone. Furthermore, it is possible to provide a resin composition having excellent color tone and excellent flame retardancy, a molded article obtained from the resin composition, a method for producing the resin composition, a method for flame retarding a synthetic resin, and an additive.
Claims
1. A composition comprising (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound. In the above general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. In the above general formula (2), R 7 and R in the general formula (3) 8 represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
2. R in the general formula (1) 1 is a group represented by general formula (2), the composition according to claim 1.
3. R in the general formula (2) 7 The composition according to claim 1, wherein is an alkylene group having 2 to 6 carbon atoms.
4. The composition according to claim 1, wherein the (B) nitrogen-containing heterocyclic compound comprises one or more triazine compounds.
5. The composition according to claim 1, wherein the (B) nitrogen-containing heterocyclic compound comprises melamine cyanurate.
6. The composition according to claim 1, wherein the content of the nitrogen-containing heterocyclic compound (B) is 70 to 99.9 parts by mass with respect to 100 parts by mass of the total of the hindered amine compound represented by general formula (1) (A) and the nitrogen-containing heterocyclic compound (B).
7. A resin composition comprising (A) a hindered amine compound represented by general formula (1), (B) a nitrogen-containing heterocyclic compound, and a synthetic resin. In the above general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. In the above general formula (2), R 7 and R in the general formula (3) 8 represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
8. The resin composition according to claim 7, wherein the synthetic resin includes a polyolefin resin.
9. A molded article obtained from the resin composition described in claim 7.
10. A method for producing a resin composition, comprising a compounding step of blending a synthetic resin with (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound. In the above general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. In the above general formula (2), R 7 and R in the general formula (3) 8 represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
11. A method for making a synthetic resin flame-retardant, comprising blending the synthetic resin with (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound. In the above general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. In the above general formula (2), R 7 and R in the general formula (3) 8 represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.
12. An additive for preparing a composition comprising (A) a hindered amine compound represented by general formula (1) and (B) a nitrogen-containing heterocyclic compound, wherein the additive comprises (A) the hindered amine compound represented by general formula (1). In the above general formula (1), R 1 R represents a group represented by the following general formula (2), a group represented by general formula (3), or a group represented by formula (4), 2 R represents a hydrocarbon group with 1 to 18 carbon atoms. 3 , R 4 , R 5 and R 6 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. In the above general formula (2), R 7 and R in the general formula (3) 8 represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.