Composition, resin composition, molded article, method for producing resin composition, method for flame-retarding synthetic resin, and additive

Abstract

Provided is a composition containing (A) a hindered amine compound represented by general formula (1), and (B) a phosphoric acid ester compound. Also provided are: a resin composition containing (A) a hindered amine compound represented by general formula (1), (B) a phosphoric acid ester compound, and a synthetic resin; a molded article obtained from the resin composition; and a method for producing a resin composition, the method including a compounding step for compounding (A) a hindered amine compound represented by general formula (1) and (B) a phosphoric acid ester compound into a synthetic resin.

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, a resin composition having excellent flame retardancy and a molded article thereof, a method for producing a resin composition, a method for flame retarding a synthetic resin, and an additive.

[0002] The addition of brominated flame retardants has been widely used as a method for making synthetic resins flame-retardant. However, because brominated flame retardants are persistent and bioaccumulative, concerns have been raised about their adverse effects on the environment and living organisms, and alternative flame retardants have been desired.

[0003] As an alternative to brominated flame retardants, examples of using a combination of hindered amine compounds and phosphorus-based flame retardants are known. For example, Patent Document 1 discloses a resin composition obtained by compounding a phosphate ester-based flame retardant and a hindered amine-based light stabilizer with a styrene-based resin.

[0004] Japanese Patent Publication No. 2007-191618

[0005] However, the technology described in Patent Document 1 may not provide sufficient flame retardancy, and further improvements are desired.

[0006] The problem that this invention aims to solve is to provide a composition that imparts excellent flame retardancy to synthetic resins.

[0007] As a result of diligent research to solve the above problems, the present inventors have found that a composition containing a hindered amine compound and a phosphate ester compound having a specific structure can solve the above problems, and have completed the present invention.

[0008] The present invention provides a composition containing (A) a hindered amine compound represented by general formula (1) and (B) a phosphate ester compound.

[0009] 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 (R ３ to R ６ ) each independently represents an alkyl group having 1 to 4 carbon atoms.

[0010] In the 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 the general formula (2), the general formula (3), and the formula (4), * represents a bond.

[0011] Further, the present invention provides a resin composition containing (A) a hindered amine compound represented by the general formula (1), (B) a phosphate ester compound, and a synthetic resin.

[0012] In the general formula (1), R １ represents a group represented by the following general formula (2), a group represented by the general formula (3), or a group represented by the formula (4), R ２ represents a hydrocarbon group having 1 to 18 carbon atoms, and R ３ to R ６ each independently represents an alkyl group having 1 to 4 carbon atoms.

[0013] In the 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 the general formula (2), the general formula (3), and the formula (4), * represents a bond.

[0014] Further, the present invention provides a molded product obtained from the above resin composition.

[0015] Further, the present invention provides a method for producing a resin composition, which includes a blending step of blending (A) a hindered amine compound represented by the general formula (1) and (B) a phosphate ester compound into a synthetic resin.

[0016] In the general formula (1), R １R 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 ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms.

[0017] 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.

[0018] 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 phosphate ester compound.

[0019] 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 ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms.

[0020] 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.

[0021] Furthermore, the present invention provides an additive for use in preparing a composition containing (A) a hindered amine compound represented by general formula (1) and (B) a phosphate ester compound, wherein the additive contains the following (A) a hindered amine compound represented by general formula (1).

[0022] In the above general formula (1), R １R 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 ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms.

[0023] 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.

[0024] According to the present invention, it is possible to provide a composition that imparts excellent flame retardancy to a synthetic resin. Furthermore, it is possible to provide a resin composition having excellent flame retardancy, a molded article obtained from the resin composition, a method for producing the resin composition, a method for making a synthetic resin flame retardant, and an additive.

[0025] Embodiments of the present invention will be described in detail below.

[0026] <Composition> The composition of this embodiment contains (A) a hindered amine compound represented by general formula (1) and (B) a phosphate ester compound. (Hereinafter, these will also be referred to as "component (A)" and "component (B)," respectively.)

[0027] 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 ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms.

[0028] 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.

[0029] The composition of this embodiment can impart excellent flame retardancy to synthetic resins. Furthermore, the composition of this embodiment can effectively suppress the deterioration of the mechanical properties and color tone of the resin composition.

[0030] The reason why the composition of this embodiment can impart excellent flame retardancy to synthetic resins is not clear, but it can be 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 phosphate ester compound also decomposes with the heat of combustion and has the function of capturing radicals in the gas phase. Since the decomposition temperatures of the two are different, the temperature ranges in which their radical capture functions are different. In the composition of this embodiment, because component (A) has an N-hydrocarbyl type hindered amine structure, the range in which the decomposition temperatures of component (A) and component (B) overlap matches the decomposition temperature range of the synthetic resin, and as a result of improved radical capture efficiency in the gas phase during combustion, flame retardancy is improved. In addition, the structure in which the hindered amine portion of general formula (1) is arranged 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.

[0031] 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.

[0032] 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.

[0033] Examples of the above-mentioned 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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] Examples of aromatic hydrocarbon groups having 6 to 18 carbon atoms include aryl groups having 6 to 18 carbon atoms and arylalkyl groups having 7 to 18 carbon atoms. Examples of aryl groups having 6 to 18 carbon atoms include phenyl, tolyl, xylyl, cumenyl, mesityl, naphthyl, pyrenyl, biphenylyl, azulenyl, indenyl, indanyl, tetralinyl, and phenanthryl groups. Examples of arylalkyl groups having 7 to 18 carbon atoms include benzyl and phenethyl groups.

[0038] R in general formula (1) ２ Preferably, the alkyl group has 1 to 18 carbon atoms, or the cycloalkyl group has 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.

[0039] R in general formula (1) ３ ~R ６ Examples of alkyl groups having 1 to 4 carbon atoms that can be used include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, and tertiary butyl groups.

[0040] R in general formula (1) 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.

[0041] R in general formula (2) ７ and R in general formula (3) ８Examples 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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 In the case of an alkylene group having 1 to 18 carbon atoms, the alkylene group is preferably one with 2 or more carbon atoms, more preferably one with 4 or more carbon atoms, preferably one with 14 or fewer carbon atoms, more preferably one with 10 or fewer carbon atoms, even more preferably one with 8 or fewer carbon atoms, and even more preferably one with 6 or fewer carbon atoms, in terms of excellent flame retardancy. Furthermore, an alkylene group having 2 to 14 carbon atoms is preferred, an alkylene group having 2 to 10 carbon atoms is more preferred, and an alkylene group having 2 to 6 carbon atoms is even more preferred. 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.

[0047] Conventional 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 corresponding to general formula (2), a diisocyanate corresponding to general formula (3), or a carbonate precursor corresponding to formula (4) is reacted with an alcohol having an N-hydrocarbyl-2,2,6,6-tetraalkylpiperidinol skeleton. Specifically, direct esterification of an acid with an alcohol, a reaction between an acid halide and an alcohol, a transesterification reaction, a 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 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.

[0048] (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.

[0049] (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.

[0050]

[0051]

[0052] Among these, one or more of compounds No. 2 to No. 13 are preferred due to their excellent color tone when blended into synthetic resins, with compounds No. 2, No. 3, No. 4, No. 5, No. 6, No. 8 or No. 9 being more preferred, one or more of compounds No. 2 to No. 6 being even more preferred, one or more of compounds No. 3 to No. 5 being even more preferred, compound No. 3 or No. 4 being even more preferred, and compound No. 3 being particularly preferred. 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 and excellent handling properties, with compounds No. 3, No. 4 or No. Compound No. 6 is more preferable. Furthermore, from the viewpoint of exhibiting a good balance between the inherent physical properties and color tone of the resin and flame retardant performance, compounds No. 3 to No. 6 are preferred.

[0053] The content of the hindered amine compound (A) represented by general formula (1) in the composition of this embodiment is preferably 0.1 to 50 parts by mass, more preferably 0.5 to 20 parts by mass, even more preferably 2 to 15 parts by mass, and particularly preferably 5 to 10 parts by mass, based on 100 parts by mass of the total of components (A) and (B). With these content levels, the flame retardancy improvement effect obtained by using components (A) and (B) in combination can be sufficiently obtained.

[0054] The content of the hindered amine compound (A) represented by general formula (1) in the composition of this embodiment is preferably 0.1 to 50 parts by mass, more preferably 0.5 to 20 parts by mass, even more preferably 2 to 15 parts by mass, and particularly preferably 5 to 10 parts by mass, per 100 parts by mass of the composition of this embodiment. With these content levels, the flame retardancy improvement effect obtained by using the combination of component (A) and component (B) can be sufficiently obtained.

[0055] (B) The phosphate ester compound refers to an ester compound obtained by the dehydration condensation of phosphoric acid and an alcohol, and may also be a condensed phosphate ester compound. Here, a condensed phosphate ester compound refers to a phosphate ester compound obtained by the dehydration condensation of phosphoric acid and an alcohol containing a polyhydric alcohol. (B) The phosphate ester compound is preferably a condensed phosphate ester compound because it has excellent heat resistance.

[0056] (B) Among the phosphate ester compounds, examples of condensed phosphate ester compounds include resorcinol bis(diphenyl phosphate), hydroquinone bis(diphenyl phosphate), bisphenol A bis(diphenyl phosphate), bisphenol A bis(dicresyl phosphate), 4,4'-biphenol bis(diphenyl phosphate), resorcinol bis(2,6-xylenyl phosphate), 4,4'-biphenol bis(2,6-xylenyl phosphate), and the like. (B) Among phosphate ester compounds, examples of phosphate ester compounds other than condensed phosphate ester compounds include triphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, cresyl diphenyl phosphate, xylyl diphenyl phosphate, cresylbis(2,6-xylenyl) phosphate, 2-ethylhexyl diphenyl phosphate, tris(chloroethyl) phosphate, tris(chloropropyl) phosphate, tris(dichloropropyl) phosphate, tris(tribromopropyl) phosphate, etc.

[0057] (B) The phosphate ester compound preferably contains a compound represented by the following general formula (5) because of its excellent flame retardancy.

[0058] In the above general formula (5), R ９ and R １０ Each of these independently represents a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 10 carbon atoms, R １１ represents a divalent aromatic hydrocarbon group represented by the following general formula (6) or (7), and n represents an integer from 1 to 30.

[0059] In the above general formulas (6) and (7), R１２ , R １３ , R １４ , R １５ , R １６ and R １７ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, a nitro group, a halogen atom, or a cyano group; X represents a direct bond, a divalent sulfur atom, a sulfonyl group, an alkylene group having 1 to 5 carbon atoms, or an alkylidene group having 2 to 5 carbon atoms; and * represents a bond.

[0060] In general formula (5), R ９ and R １０ Examples of alkyl groups having 1 to 10 carbon atoms that can be adopted include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, second butyl group, third butyl group, pentyl 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, and 2-propylheptyl group.

[0061] In general formula (5), R ９ and R １０ From the standpoint of excellent flame retardancy, it is preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0062] In general formula (5), n represents an integer from 1 to 30. The value of n is preferably 1 to 10, more preferably 1 to 7, and even more preferably 1 to 5, from the viewpoint of improving the heat resistance and handling properties of the compound represented by general formula (5). The compound represented by general formula (5) may be a mixture of multiple compounds with different values ​​of n.

[0063] In general formulas (6) and (7), R １２ , R １３ , R １４ , R １５ , R １６ or R １７ The alkyl group having 1 to 4 carbon atoms that can be formed is R in general formula (5). ９ and R １０Examples of the alkyl group having 1 to 10 carbon atoms which can be taken include those having 1 to 4 carbon atoms among those exemplified above.

[0064] In general formulas (6) and (7), R １２ , R １３ , R １４ , R １５ , R １６ and R １７ Examples of the alkoxy group having 1 to 4 carbon atoms which can be taken include an alkoxy group in which the alkyl group having 1 to 4 carbon atoms exemplified above is bonded to an oxygen atom.

[0065] In general formulas (6) and (7), R １２ , R １３ , R １４ , R １５ , R １６ and R １７ Examples of the cycloalkyl group having 3 to 8 carbon atoms which can be taken include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc. or a group in which these groups are substituted with an alkyl group having 1 to 5 carbon atoms, etc.

[0066] In general formulas (6) and (7), R １２ , R １３ , R １４ , R １５ , R １６ and R １７ Examples of the aryl group having 6 to 10 carbon atoms which can be taken include, for example, a phenyl group, a tolyl group, a xylyl group, a 2,4,6 - trimethylphenyl group, a 2 - tert - butylphenyl group, a 4 - tert - butylphenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, a tetralinyl group, etc.

[0067] R １２ , R １３ , R １４ , R １５ , R １６ and R １７ are preferably a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a cyclohexyl group, an aryl group having 6 to 8 carbon atoms, and more preferably a hydrogen atom.

[0068] Examples of alkylene groups with 1 to 5 carbon atoms that X can take in general formula (7) include methylene, ethylene, propylene, butylene, isobutylene, and pentylene groups.

[0069] Examples of alkylidene groups with 2 to 5 carbon atoms that X can take in general formula (7) include ethylidene, propyridene, isopropylidene, butyridene, and isobutylidene.

[0070] From the standpoint of excellent thermal stability, X in general formula (7) is preferably a directly bonded alkylene group having 1 to 5 carbon atoms, or an alkylidene group having 2 to 5 carbon atoms, more preferably a directly bonded alkylidene group having 2 to 5 carbon atoms, and even more preferably a directly bonded isopropylidene group.

[0071] Specific examples of divalent aromatic hydrocarbon groups represented by general formula (6) include, for example, the 1,4-phenylene group and the 1,3-phenylene group.

[0072] Specific examples of divalent aromatic hydrocarbon groups represented by general formula (7) include, for example, the 4,4'-biphenylene group, the 4,4'-isopropylidenediphenylene group, the 4,4'-thiodiphenylene group, and the 4,4'-sulfonyldiphenylene group.

[0073] Specific examples of compounds represented by general formula (5) include, for example, compounds No. 17 to No. 21 listed below. In compounds No. 17 to No. 21 below, n represents an integer from 1 to 30.

[0074]

[0075] (B) The phosphate ester compound preferably contains one or more of the above compounds No. 17 to No. 21, more preferably contains one or more of the above compounds No. 17 to No. 20, and even more preferably contains one or more of the above compounds No. 17 and No. 18, from the viewpoint of flame retardancy and heat resistance. (B) The phosphate ester compound preferably contains one or more of the above compounds No. 17 to No. 21, with an n value of 1 to 10, more preferably 1 to 7, and even more preferably 1 to 5, from the viewpoint of improving the heat resistance and handling properties of the compound. Furthermore, the (B) phosphate ester compound may be one or more of the above compounds No. 17 to No. 21, and may be a mixture of multiple compounds with different n values. These compounds may be used individually or in combination of two or more.

[0076] In the composition of this embodiment, the content of the compound represented by formula (5) in the (B) phosphate ester compound is preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, particularly preferably 95% by mass or more, and may be 100% by mass.

[0077] The content of the (B) phosphate ester compound in the composition of this embodiment is preferably 50 to 99.9 parts by mass, more preferably 80 to 99.5 parts by mass, even more preferably 85 to 98 parts by mass, even more preferably 90 to 98 parts by mass, and particularly preferably 90 to 95 parts by mass, based on 100 parts by mass of the total of components (A) and (B). With these content levels, the flame retardancy improvement effect from the combined use of components (A) and (B) can be sufficiently obtained.

[0078] The content of the (B) phosphate ester compound in the composition of this embodiment is preferably 50 to 99.9 parts by mass, more preferably 80 to 99.5 parts by mass, even more preferably 85 to 98 parts by mass, even more preferably 90 to 98 parts by mass, and particularly preferably 90 to 95 parts by mass, per 100 parts by mass of the composition of this embodiment. With these content levels, the flame retardancy improvement effect obtained by using the combined effects of component (A) and component (B) can be sufficiently obtained.

[0079] 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. By setting the total content of component (A) and component (B) within the above range, flame retardant performance can be stably exhibited.

[0080] 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 or styrene-based resins among synthetic resins, the composition of this embodiment can be suitably used as a flame retardant for polyolefin resins or styrene-based resins, and even more suitably used as a flame retardant for styrene-based resins.

[0081] When adding the composition of the present invention to a resin, components (A) and (B) may be mixed beforehand and then added to the resin, or components (A) and (B) may be added to the resin separately.

[0082] <Resin Composition> The resin composition of this embodiment contains (A) a hindered amine compound represented by general formula (1), (B) a phosphate ester compound, and a synthetic resin. The resin composition of this embodiment has excellent flame retardancy. Regarding the hindered amine compound represented by general formula (1) and (B) phosphate ester compound in the resin composition of this embodiment, the descriptions of them in the above-mentioned composition of this embodiment can be applied as appropriate.

[0083] Here, (A) the hindered amine compound represented by general formula (1) and (B) the phosphate ester compound are the same as those exemplified as components contained in the composition of this embodiment described above.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] Examples of the polyolefin resins mentioned above include polypropylene, high-density polyethylene, low-density polyethylene, linear low-density polyethylene, polybutene-1, poly-3-methylpentene, poly-4-methylpentene, α-olefin polymers such as ethylene / propylene blocks or random copolymers.

[0088] 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).

[0089] Examples of the above-mentioned polysulfide resins include polyphenylene sulfide. Examples of the above-mentioned polyamide resins include polyhexamethylene adipamide.

[0090] The polycarbonate resin mentioned above is a resin having carbonate bonds, and can be obtained, for example, by a polymerization reaction between a divalent hydroxyaromatic compound and a carbonate precursor.

[0091] The above-mentioned divalent hydroxyaromatic 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; and 4,4'-dihydroxydiphenyl ether and 4,4'-dihydroxy-3,3'-dimethylphenyl ether. Examples include dihydroxyaryl ethers such as tel, 4,4'-dihydroxy-2,5-dihydroxydiphenyl ether; dihydroxyaryl sulfur compounds such as 4,4'-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, 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfone, and phenolphthalein. These may be used individually or in combination of two or more, and may also be used in combination with polyhydric hydroxyaromatic compounds having three or more hydroxyl groups.

[0092] Suitable specific examples of the above-mentioned carbonate precursors include phosgene, diester carbonate, diphenyl carbonate, dihaloformates of divalent phenols, and mixtures thereof.

[0093] From the standpoint of exhibiting more effective flame-retardant properties, the synthetic resin preferably contains a polyolefin resin or a styrene-based resin, more preferably contains a styrene-based resin, and even more preferably consists solely of a styrene-based resin.

[0094] The styrene-based resins mentioned above are polymers containing vinyl group-containing aromatic hydrocarbons as monomers. Examples include polymers of vinyl group-containing aromatic hydrocarbons alone, and copolymers of vinyl group-containing aromatic hydrocarbons with other monomers. Examples of other monomers include maleic anhydride, phenylmaleimide, acrylic acid esters, methacrylic acid esters, butadiene, isoprene, acrylonitrile, and methacrylonitrile.

[0095] Specific examples of the above styrene-based resins include, for example, 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 lipids, 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.

[0096] Among these styrene-based resins, polystyrene, high-impact polystyrene, acrylonitrile-butadiene-styrene copolymer, heat-resistant ABS resin, acrylonitrile-styrene copolymer, acrylate-styrene-acrylonitrile copolymer, acrylonitrile-ethylene propylene rubber-styrene copolymer, methyl methacrylate-acrylonitrile-butadiene-styrene copolymer, and hydrogenated styrene-based elastomer resin are preferred due to their excellent flame-retardant properties. Polystyrene, high-impact polystyrene, acrylonitrile-butadiene-styrene copolymer, heat-resistant ABS resin, and acrylate-styrene-acrylonitrile copolymer are more preferred, and high-impact polystyrene, acrylonitrile-butadiene-styrene copolymer, and heat-resistant ABS resin are even more preferred.

[0097] 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.

[0098] The content of the hindered amine compound (A) represented by general formula (1) in the resin composition of this embodiment is preferably 0.1 to 10 parts by mass, more preferably 0.2 to 5 parts by mass, even more preferably 0.3 to 3.5 parts by mass, and particularly preferably 0.5 to 2.5 parts by mass, per 100 parts by mass of synthetic resin. With these content levels, the flame retardant performance of component (A) can be fully exhibited, and the bleeding of component (A) is minimized.

[0099] The content of the (B) phosphate ester compound in the resin composition of this embodiment is preferably 1 to 40 parts by mass, more preferably 5 to 30 parts by mass, even more preferably 10 to 25 parts by mass, even more preferably 12 to 22 parts by mass, and particularly preferably 14 to 18 parts by mass, per 100 parts by mass of synthetic resin. With these content levels, the flame retardant properties of component (B) can be fully exhibited, and the bleeding of component (B) is minimized.

[0100] Furthermore, the content of the (B) phosphate ester compound in the resin composition of this embodiment is preferably 50 to 99.9 parts by mass, more preferably 80 to 99.5 parts by mass, even more preferably 85 to 98 parts by mass, and particularly preferably 90 to 95 parts by mass, based on 100 parts by mass of the total of components (A) and (B). With these content levels, the flame retardancy improvement effect from the combined use of components (A) and (B) can be sufficiently obtained.

[0101] The total content of component (A) and component (B) in the resin composition of this embodiment is preferably 2 to 50 parts by mass, more preferably 5 to 30 parts by mass, even more preferably 10 to 23 parts by mass, even more preferably 12 to 20 parts by mass, and particularly preferably 15 to 18 parts by mass, per 100 parts by mass of synthetic resin. By setting the total content of component (A) and component (B) within the above range, the inherent physical properties of the resin and flame retardant properties can be exhibited in a well-balanced manner.

[0102] The total content of component (A) and component (B) in the resin composition of this embodiment is preferably 2 to 35 parts by mass, more preferably 5 to 25 parts by mass, even more preferably 9 to 22 parts by mass, even more preferably 11 to 19 parts by mass, and particularly preferably 14 to 17 parts by mass, per 100 parts by mass of the resin composition of this embodiment. By setting the total content of component (A) and component (B) within the above range, the inherent physical properties of the resin and flame retardant performance can be exhibited in a well-balanced manner.

[0103] The content of the styrene-based resin in the resin composition of this embodiment is preferably 60 to 99 parts by mass, more preferably 75 to 95 parts by mass, even more preferably 80 to 90 parts by mass, and even more preferably 80 to 88 parts by mass, per 100 parts by mass of the resin composition of this embodiment. With these content levels, the inherent physical properties of the resin and flame retardant properties can be exhibited in a well-balanced manner.

[0104] The resin composition of this embodiment may contain (A) a hindered amine compound represented by general formula (1), (B) a phosphate ester compound, and any other components besides the synthetic resin. The following describes the optional components that the resin composition of this embodiment may contain.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] 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.

[0111] 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 TINUVINNOR 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.

[0112] The form of the resin composition in 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.

[0113] 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.

[0114] <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 phosphate ester compound.

[0115] According to the method for producing the resin composition of this embodiment, a resin composition having excellent flame retardancy can be produced.

[0116] 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.

[0117] 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 phosphate ester compound, and any optional components. For example, two or more components selected from (A) a hindered amine compound represented by general formula (1), (B) a phosphate ester compound, and any optional components may be mixed in advance and then 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.

[0118] Furthermore, as a method for blending (A) a hindered amine compound represented by general formula (1), (B) a phosphate ester 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 phosphate ester compound, and an optional component, and then blending the masterbatch into the remaining synthetic resin.

[0119] <Molded Articles> The molded articles of this embodiment are obtained from the resin composition of this embodiment. The molded articles of this embodiment have excellent flame retardancy.

[0120] The molding method for the molded product is not particularly limited, and examples of molding methods include extrusion molding, calendering, injection molding, roll molding, compression molding, and blow molding. These molding methods allow for the production of molded products of various shapes, such as resin plates, sheets, films, pellets, and irregularly shaped products.

[0121] Furthermore, the molded products of this embodiment can be used in a wide range of industrial fields, including electrical / electronic / communications, 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, they can be 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 kotatsu (heated tables); AV equipment such as TVs, VTRs, video cameras, radio cassette players, tape recorders, MiniDiscs, CD players, speakers, and liquid crystal displays; electrical and electronic components such as connectors, relays, capacitors, switches, printed circuit boards, coil bobbins, semiconductor encapsulating materials, LED encapsulating materials, electric wires, cables, transformers, deflection yokes, distribution boards, and clocks, as well as communication equipment.

[0122] 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.

[0123] 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.

[0124] <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 phosphate ester 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.

[0125] <Additives> The additive of this embodiment is an additive for use in preparing a composition containing (A) a hindered amine compound represented by general formula (1) and (B) a phosphate ester compound, wherein (A) contains the hindered amine compound represented by general formula (1). The additive of this embodiment does not contain (B) the phosphate ester compound. The content of the hindered amine compound in the additive is preferably 10% by mass or more, more preferably 50% by mass or more, and even more preferably 70% by mass or more. A composition using the additive of this embodiment can impart excellent flame retardancy to synthetic resins.

[0126] <Other> The present invention includes the following embodiments.

[0127] [1] A composition comprising (A) a hindered amine compound represented by general formula (1) and (B) a phosphate ester compound.

[0128] 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 ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms.

[0129] 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.

[0130] [2] R in general formula (1) １The composition according to [1], wherein is a group represented by general formula (2).

[0131] [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.

[0132] [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.

[0133] [5] (A) The composition according to [1], wherein the hindered amine compound represented by general formula (1) is one or more of the following compounds No. 2 to No. 13.

[0134]

[0135] [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. 3 to No. 5, even more preferably compound No. 3 or No. 4, and particularly preferably compound No. 3.

[0136] [7] The composition according to any one of [1] to [6], wherein (B) the phosphate ester compound is a condensed phosphate ester compound.

[0137] [8] (B) The composition according to any one of items [1] to [6], wherein the phosphate ester compound comprises a compound represented by the following general formula (5).

[0138] In the above general formula (5), R ９ and R １０ Each of these independently represents a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 10 carbon atoms, R １１ represents a divalent aromatic hydrocarbon group represented by the following general formula (6) or (7), and n represents an integer from 1 to 30.

[0139] In the above general formulas (6) and (7), R１２ , R １３ , R １４ , R １５ , R １６ and R １７ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, a nitro group, a halogen atom, or a cyano group; X represents a direct bond, a divalent sulfur atom, a sulfonyl group, an alkylene group having 1 to 5 carbon atoms, or an alkylidene group having 2 to 5 carbon atoms; and * represents a bond.

[0140] [9] The composition according to any one of [1] to [6], wherein (B) the phosphate ester compound is one or more of the compounds No. 17 to No. 20 listed below.

[0141] In compounds No. 17 to No. 20, n represents an integer from 1 to 30.

[0142]

[10] The composition according to [8] or [9], wherein the value of n is 1 to 10, preferably 1 to 7, and more preferably 1 to 5.

[0143]

[11] The composition according to any one of [1] to

[10] , wherein the content of (B) the phosphate ester compound is 50 to 99.9 parts by mass with respect to 100 parts by mass of the total of (A) the hindered amine compound represented by general formula (1) and (B) the phosphate ester compound.

[0144]

[12] A composition according to any one of [1] to

[11] , which is a flame retardant.

[0145]

[13] A composition according to any one of [1] to

[11] , which is a flame retardant for synthetic resins.

[0146]

[14] A composition according to any one of [1] to

[11] , which is a flame retardant for polyolefin resins or a flame retardant for styrene resins, more preferably a flame retardant for styrene resins.

[0147]

[15] A resin composition comprising (A) a hindered amine compound represented by general formula (1), (B) a phosphate ester compound, and a synthetic resin.

[0148] 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 ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms.

[0149] 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.

[0150]

[16] R in general formula (1) １ The resin composition according to

[15] , wherein is a group represented by general formula (2).

[0151]

[17] R in general formula (2) ７ The resin composition according to

[15] or

[16] , wherein is an alkylene group having 2 to 14 carbon atoms.

[0152]

[18] R in general formula (2) ７ The resin composition according to

[15] or

[16] , wherein is an alkylene group having 2 to 6 carbon atoms.

[0153]

[19] (A) The resin composition according to

[15] , wherein the hindered amine compound represented by general formula (1) is one or more selected from the following compounds No. 2 to No. 13.

[0154]

[0155]

[20] (A) The resin composition according to

[15] , wherein the hindered amine compound represented by general formula (1) is one or more selected from compounds No. 2 to No. 13, preferably one or more selected from compounds No. 2 to No. 6, even more preferably one or more selected from compounds No. 3 to No. 5, even more preferably compound No. 3 or No. 4, and particularly preferably compound No. 3.

[0156]

[21] The resin composition according to any one of

[15] to

[20] , wherein (B) the phosphate ester compound is a condensed phosphate ester compound.

[0157]

[22] (B) The resin composition according to any one of the items

[15] to

[20] , wherein the phosphate ester compound is one or more compounds represented by the following general formula (5).

[0158] In the above general formula (5), R ９ and R １０ Each of these independently represents a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 10 carbon atoms, R １１ represents a divalent aromatic hydrocarbon group represented by the following general formula (6) or (7), and n represents an integer from 1 to 30.

[0159] In the above general formulas (6) and (7), R １２ , R １３ , R １４ , R １５ , R １６ and R １７ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, a nitro group, a halogen atom, or a cyano group; X represents a direct bond, a divalent sulfur atom, a sulfonyl group, an alkylene group having 1 to 5 carbon atoms, or an alkylidene group having 2 to 5 carbon atoms; and * represents a bond.

[0160]

[23] (B) The resin composition according to any one of the following compounds No. 17 to No. 20, wherein the phosphate ester compound is one or more of the compounds No. 17 to No. 20.

[0161] In compounds No. 17 to No. 20, n represents an integer from 1 to 30.

[0162]

[24] The resin composition according to

[22] or

[23] , wherein the value of n is 1 to 10, preferably 1 to 7, more preferably 1 to 5.

[0163]

[25] The resin composition according to any one of

[15] to

[24] , wherein the synthetic resin comprises a polyolefin resin or a styrene resin, more preferably a styrene resin.

[0164]

[26] A resin composition according to any one of

[15] to

[24] , wherein the synthetic resin consists solely of a styrene-based resin.

[0165]

[27] The resin composition according to

[25] or

[26] , wherein the styrene resin is one or more selected from the group consisting of polystyrene, high-impact polystyrene, acrylonitrile-butadiene-styrene copolymer, heat-resistant ABS resin, acrylonitrile-styrene copolymer, acrylate-styrene-acrylonitrile copolymer, acrylonitrile-ethylenepropylene rubber-styrene copolymer, methyl methacrylate-acrylonitrile-butadiene-styrene copolymer and hydrogenated styrene elastomer resin, preferably one or more selected from the group consisting of polystyrene, high-impact polystyrene, acrylonitrile-butadiene-styrene copolymer, heat-resistant ABS resin and acrylate-styrene-acrylonitrile copolymer, and more preferably one or more selected from the group consisting of high-impact polystyrene, acrylonitrile-butadiene-styrene copolymer and heat-resistant ABS resin.

[0166]

[28] (A) The resin composition according to any one of

[15] to

[27] , wherein the content of the hindered amine compound represented by general formula (1) is preferably 0.1 to 10 parts by mass, more preferably 0.2 to 5 parts by mass, even more preferably 0.3 to 3.5 parts by mass, and even more preferably 0.5 to 2.5 parts by mass, per 100 parts by mass of the synthetic resin.

[0167]

[29] (B) The resin composition according to any one of

[15] to

[28] , wherein the content of the phosphate ester compound is preferably 1 to 40 parts by mass, more preferably 5 to 30 parts by mass, even more preferably 10 to 25 parts by mass, even more preferably 12 to 22 parts by mass, and even more preferably 14 to 18 parts by mass, per 100 parts by mass of the synthetic resin.

[0168]

[30] The resin composition according to any one of

[15] to

[29] , wherein the content of (B) the phosphate ester compound is 50 to 99.9 parts by mass, preferably 80 to 99.5 parts by mass, more preferably 85 to 98 parts by mass, even more preferably 90 to 98 parts by mass, and particularly preferably 90 to 95 parts by mass, based on 100 parts by mass of the total of (A) the hindered amine compound represented by general formula (1) and (B) the phosphate ester compound.

[0169]

[31] A molded article obtained from any one of the resin compositions described in

[15] to

[30] .

[0170]

[32] 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 phosphate ester compound.

[0171] 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 ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms.

[0172] In the above general formula (2), R ７and 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.

[0173]

[33] 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 phosphate ester compound.

[0174] 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 ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms.

[0175] 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.

[0176]

[34] An additive for use in preparing a composition comprising (A) a hindered amine compound represented by general formula (1) and (B) a phosphate ester compound, wherein the additive comprises (A) a hindered amine compound represented by general formula (1).

[0177] 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 ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms.

[0178] In the above general formula (2), R ７ and R in the general formula (3) ８represents a direct bond or a divalent hydrocarbon group having 1 to 18 carbon atoms. In general formulas (2), (3), and (4), * represents a bond.

[0179]

[35] Use of an additive containing (A) a hindered amine compound represented by general formula (1) for preparing a composition containing (A) a hindered amine compound represented by general formula (1) and (B) a phosphate ester compound.

[0180] 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 ６ Each of these independently represents an alkyl group having 1 to 4 carbon atoms.

[0181] 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.

[0182] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto.

[0183] The details of the components in Tables 1-4 are shown below. HIPS: High Impact Polystyrene (Manufactured by PS Japan, Product Name: H9152, MFR = 5.5 g / 10 min (JIS K 7210, 200℃ / 5.0 kg)) ABS: Acrylonitrile-Butadiene-Styrene Copolymer (Manufactured by Nippon A&L, Product Name: GA-101, MVR = 26 cm) ３ / 10 min (JIS K 7210, 220℃ / 10kg) (A)-1: Compound No. 3 (A)-2: Compound No. 5 (A)-3: Compound No. 6 (A)-X1: Tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate

[0184] (A)-X2: Polycondensate of dimethyl succinate and 4-hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine

[0185] (A)-X3: N,N',4,7-Tetrakis{4,6-bis[N-butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine-4-yl)amino]-1,3,5-triazine-2-yl}-4,7-diazadecane-1,4,10-triamine

[0186] (A)-X4: Bis(2,2,6,6-tetramethylpiperidyl)sebacate

[0187] (A)-X5: 2,4-dichloro-6-(1,1,3,3-tetramethylbutylamino)-1,3,5-triazine / N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine polycondensate

[0188] (B)-1: Compound No. 17 (a mixture of compounds where n is 1 to 7) (B)-2: Compound No. 18 (a mixture of compounds where n is 1 to 7) (B)-3: Compound No. 20 (a mixture of compounds where n is 1 to 3) (B)-4: Compound No. 21 (a compound where n is 1)

[0189] <Preparation of Test Specimens for Evaluation Tests (HIPS, Examples 1-16, Comparative Examples 1-16)> The components were mixed in the amounts listed in Tables 1-3, and melt-kneaded in a twin-screw extruder (TEX25αIII, manufactured by Japan Steel Works) at a cylinder temperature of 190°C and a screw speed of 150 rpm to obtain resin strands. The obtained resin strands were cut with a pelletizer to obtain pelletized resin compositions. The pelletized resin compositions obtained above were injection-molded in an injection molding machine (EC60NII-1.5A, manufactured by Toshiba Machine) at a resin temperature of 190°C and a mold temperature of 40°C to obtain rectangular plate-shaped test specimens (127 mm × 12.7 mm × 1.6 mm) for evaluating flame retardancy and colorability, and rod-shaped test specimens (80 mm × 10 mm × 4.0 mm) for evaluating mechanical properties.

[0190] <Preparation of Test Specimens for Evaluation Tests (ABS, Example 17, Comparative Examples 17-20)> The components were mixed in the amounts listed in Table 4, and melt-kneaded in a twin-screw extruder (TEX25αIII, manufactured by Japan Steel Works) at a cylinder temperature of 190°C and a screw speed of 150 rpm to obtain resin strands. The obtained resin strands were cut with a pelletizer to obtain pelletized resin compositions. The pelletized resin compositions obtained above were injection-molded in an injection molding machine (EC60NII-1.5A, manufactured by Toshiba Machine) at a resin temperature of 210°C and a mold temperature of 40°C to obtain rectangular plate-shaped test specimens (127 mm × 12.7 mm × 1.6 mm) for evaluating flame retardancy and colorability, and rod-shaped test specimens (80 mm × 10 mm × 4.0 mm) for evaluating mechanical properties.

[0191] <Flame Retardancy Evaluation: UL-94V> A rectangular plate-shaped test piece measuring 127 mm x 12.7 mm x 1.6 mm, prepared as described above, was held vertically, and a burner flame was applied to the lower end for 10 seconds. After removing the flame, the burning time t1 was measured until the flame that ignited the test piece went out. Next, as soon as the flame went out, a second application of the flame was started for 10 seconds, and the burning time t2 was measured in the same manner as the first time until the ignited flame went out. At the same time, it was also evaluated whether the cotton beneath the test piece ignited due to the falling ember. A combustion rank was assigned according to the UL-94 standard based on t1, t2, and whether the cotton ignited. V-0 is the highest combustion rank, and the flame retardancy decreases as the rank decreases to V-1, V-2, etc. However, those that do not fall into any rank from V-0 to V-2 are indicated as "Not V". The evaluation results are shown in Tables 1 to 4.

[0192] <Coloring Evaluation: Yellowness> Using the rectangular plate-shaped test piece measuring 127 mm × 12.7 mm × 1.6 mm obtained above, the yellowness (Y.I.) was measured using a multi-light source spectrophotometer (X-rite ColorEye 7000A). A higher yellowness number indicates a stronger yellow tint and inferior color tone. The evaluation results are shown in Tables 1 to 4. Note that a low yellowness number, including negative values, has advantages such as suppressing the yellowing effect and providing a margin to tolerate yellowing over time with use.

[0193] <Mechanical Properties Evaluation: Charpy Impact Strength> The Charpy impact strength of the rod-shaped test specimens obtained above was measured using a Charpy impact tester manufactured by Toyo Seiki Seisakusho Co., Ltd., under conditions of 23°C in accordance with ISO 179. The impact strength was also measured by making a notch in the test specimen. The evaluation results are shown in Tables 1 to 3.

[0194] <Mechanical Properties Evaluation: Thermal Distortion Temperature> The thermal distortion temperature (HDT) of the rod-shaped test specimens obtained above was measured using an HDT testing machine manufactured by Toyo Seiki Seisakusho under a load of 1.8 MPa, in accordance with ISO 75. The evaluation results are shown in Table 4.

[0195]

[0196]

[0197]

[0198]

[0199] Tables 1-3 show the evaluation results for flame retardancy and colorability of high-impact polystyrene (HIPS). For compositions containing components (A) and (B) (Examples 1-16), the UL-94V flammability rank was V-2. On the other hand, for compositions without components (A) and (B) (Comparative Example 1), compositions containing only component (A) (Comparative Examples 2-4), compositions containing only component (B), and compositions containing a comparative compound to component (A) and component (B) (Comparative Examples 5-16), the UL-94V flammability rank was Not V.

[0200] These findings demonstrate that by incorporating components (A) and (B) into HIPS, HIPS can be imparted with excellent flame retardant properties. Therefore, it has been shown that a composition containing components (A) and (B) can impart excellent flame retardant properties to HIPS.

[0201] Table 4 shows the evaluation results for flame retardancy in acrylonitrile-butadiene-styrene copolymer (ABS). The evaluation results shown in Table 4 indicate that by incorporating components (A) and (B) into ABS, excellent flame retardancy can be imparted to the ABS. Therefore, it is shown that a composition containing components (A) and (B) can impart excellent flame retardancy to ABS.

[0202] From the above results, it was confirmed that the composition of this embodiment can impart excellent flame retardancy to synthetic resins.

Claims

1. A composition containing (A) a hindered amine compound represented by general formula (1) and (B) a phosphate ester 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 The composition according to claim 1, wherein is a group represented by the general formula (2).

3. R ​​in the general formula (2) ７ The composition according to claim 1, wherein the alkylene group has 2 to 14 carbon atoms.

4. R in the general formula (2) ７ The composition according to claim 1, wherein the alkylene group has 2 to 6 carbon atoms.

5. The composition according to claim 1, wherein the (B) phosphate ester compound comprises a compound represented by the following general formula (5). In the above general formula (5), R ９ and R １０ Each of these independently represents a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 10 carbon atoms, R １１ represents a divalent aromatic hydrocarbon group represented by the following general formula (6) or (7), and n represents an integer from 1 to 30. In the above general formulas (6) and (7), R １２ , R １３ , R １４ , R １５ , R １６ and R １７ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, a nitro group, a halogen atom, or a cyano group; X represents a direct bond, a divalent sulfur atom, a sulfonyl group, an alkylene group having 1 to 5 carbon atoms, or an alkylidene group having 2 to 5 carbon atoms; and * represents a bond.

6. The composition according to claim 1, wherein the content of the (B) phosphate ester compound is 50 to 99.9 parts by mass with respect to 100 parts by mass of the total of the (A) hindered amine compound represented by general formula (1) and the (B) phosphate ester compound.

7. A resin composition comprising (A) a hindered amine compound represented by general formula (1), (B) a phosphate ester 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. A molded article obtained from the resin composition described in claim 7.

9. 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 phosphate ester 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.

10. 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 phosphate ester 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. An additive for use in preparing a composition comprising (A) a hindered amine compound represented by general formula (1) and (B) a phosphate ester compound, wherein the additive comprises the following (A) a 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 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.

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