Flame retardant, composition, and molded article

Abstract

The purpose of the present invention is to provide a flame retardant that uses an N-alkyl type hindered amine compound and imparts excellent flame retardancy to a synthetic resin.　The present invention provides a flame retardant containing a hindered amine compound (A), wherein the hindered amine compound (A) is a compound represented by general formula (1).　In general formula (1), R1 represents a carbonyl group or the like, R2 represents a hydrocarbon group having 1-18 carbon atoms, and R3 to R6 each independently represent an alkyl group having 1-4 carbon atoms.

Description

Flame retardants, compositions, and molded articles

[0001] The present invention relates to a flame retardant containing a hindered amine compound having a specific structure, as well as a composition containing the flame retardant and a molded article thereof.

[0002] Synthetic resins are widely used due to their convenience, but they have the drawback of being highly flammable. Various technologies have been developed to impart flame retardancy to synthetic resins. One such technology is hindered amine compounds, which are known to be effective as flame retardants.

[0003] Patent Document 1 describes a technology in which a NOR-HALS compound having a specific structure is used as a flame retardant for a polymer. Patent Document 2 describes a resin composition for a solar cell encapsulant containing an NOR hindered amine flame retardant for an olefin resin material. Patent Document 3 describes a laminate of multiple layers containing a polypropylene resin and an NOR hindered amine compound. Here, paragraph

[0076] of Patent Document 2 describes that N-methyl hindered amine compounds are thought not to exhibit the same flame retardancy as NOR hindered amine derivatives. Furthermore, paragraph

[0067] of Patent Document 3 describes that when an N-methyl hindered amine stabilizer is used, flame retardancy is reduced compared to when an NOR hindered amine stabilizer is used.

[0004] As an example of using a non-N-alkoxy hindered amine compound, Patent Document 4 proposes a flame-retardant resin composition comprising a base resin containing a polyolefin resin, a flame retardant, and a flame-retardant aid, and including a hindered amine compound as the flame-retardant aid, and in the examples, an N-alkyl hindered amine compound is used. However, Patent Document 4 describes that the hindered amine compound contains an NOR-containing group, which can further improve the flame retardancy of the flame-retardant resin composition, and the examples also describe results showing that hindered amine compounds containing an NOR-containing group have superior flame retardancy to hindered amine compounds not containing an NOR-containing group. Furthermore, the hindered amine compound in Patent Document 4 is used as a flame-retardant aid in combination with a primary flame retardant, and there is no description that it functions as a flame retardant on its own.

[0005] US2015 / 0284535 A1 JP 2012-015402 A JP 2018-039134 A JP 2021-042334 A

[0006] The N-alkoxy hindered amine compound described in Patent Document 1 can impart excellent flame retardant properties to resins, but is liquid at room temperature. When blending a liquid additive with a synthetic resin, special equipment for handling liquid substances is required, making handling more difficult than with solid additives. Furthermore, the N-alkoxy hindered amine compounds described in Patent Documents 1 to 4 have the problem of high production costs due to the expensive raw materials and complex production processes.

[0007] On the other hand, N-alkyl hindered amine compounds have the potential for cost reduction because the raw materials are inexpensive, but as described in Patent Documents 1 to 4, there has been a problem in that no compounds capable of providing excellent flame retardancy have been found.

[0008] Therefore, an object of the present invention is to provide a flame retardant which uses an N-alkyl hindered amine compound and which imparts excellent flame retardancy to synthetic resins.

[0009] As a result of intensive investigations aimed at solving the above-mentioned problems, the present inventors have found that a flame retardant containing an N-alkyl hindered amine compound having a specific structure can solve the above-mentioned problems, and have thus completed the present invention.

[0010] The present invention provides a flame retardant containing (A) a hindered amine compound, wherein the (A) hindered amine compound is a compound represented by the following general formula (1):

[0011] In general formula (1), R １ represents a group represented by the following general formula (2), (3) or (4), and R ２ represents a hydrocarbon group having 1 to 18 carbon atoms, and R ３ ~R ６ each independently represents an alkyl group having 1 to 4 carbon atoms.

[0012] 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.

[0013] The present invention also relates to a composition containing the above flame retardant and a synthetic resin, and a flame retardant obtained from the composition.

[0014] According to the present invention, it is possible to provide a flame retardant that imparts excellent flame retardancy to a synthetic resin, and also to provide a composition containing the flame retardant and a molded article thereof.

[0015] Hereinafter, embodiments of the present invention will be described in detail. <Flame Retardant> The flame retardant of the present invention contains (A) a hindered amine compound. The (A) hindered amine compound is a compound represented by the following general formula (1):

[0016] In general formula (1), R １ represents a group represented by the following general formula (2), (3) or (4), and R ２ represents a hydrocarbon group having 1 to 18 carbon atoms, and R ３ ~R ６each independently represents an alkyl group having 1 to 4 carbon atoms.

[0017] 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.

[0018] The reason why the flame retardant of the present invention has excellent flame retardancy due to the inclusion of a hindered amine compound having the above-mentioned specific structure among hindered amine compounds is not clear, but is presumed as follows. Hindered amine flame retardants exhibit flame retardancy by capturing hydroxyl radicals and alkylperoxy radicals generated in the gas phase during combustion with the hindered amine structure moiety. In the flame retardant of the present invention, the hindered amine structures are located at both ends of the linear molecular chain, which results in the hindered amine structures being appropriately dispersed in the synthetic resin, improving the radical scavenging efficiency in the gas phase during combustion, and as a result, the flame retardant exhibits excellent flame retardancy.

[0019] R in general formula (1) １ As the group represented by the general formula (2), a group represented by the general formula (3) is preferred, and a group represented by the general formula (2) is more preferred. This further improves the flame retardant performance of the flame retardant of the present invention.

[0020] R in general formula (1) ２ Examples of the hydrocarbon group having 1 to 18 carbon atoms represented by the formula (I) include an aliphatic hydrocarbon group having 1 to 18 carbon atoms and an aromatic hydrocarbon group having 6 to 18 carbon atoms. Examples of the aliphatic hydrocarbon group having 1 to 18 carbon atoms include an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, and a cycloalkyl group having 3 to 18 carbon atoms.

[0021] Examples of the alkyl group having 1 to 18 carbon atoms include linear or branched alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, heptyl, octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, 2-propylheptyl, undecyl, dodecyl, tetradecyl, hexadecyl, and octadecyl.

[0022] Examples of the alkenyl group having 2 to 18 carbon atoms include linear and cyclic alkenyl groups such as vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 3-pentenyl, 4-pentenyl, 2-hexenyl, 3-hexenyl, 5-hexenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 3-octenyl, 3-nonenyl, 4-decenyl, 3-undecenyl, 4-dodecenyl, 3-cyclohexenyl, 2,5-cyclohexadienyl-1-methyl, and 4,8,12-tetradecatrienyl allyl.

[0023] Examples of the cycloalkyl group having 3 to 18 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclooctadecyl group, a 2-bornyl group, a 2-isobornyl group, a 1-adamantyl group, a methylcyclopentyl group, a methylcyclohexyl group, a dimethylcyclohexyl group, and a methylcycloheptyl group.

[0024] Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms include a phenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a benzyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, a tetralinyl group, a phenanthryl group, a pyrenyl group, and a biphenyl group.

[0025] R in general formula (1) ２ As R, alkyl groups having 1 to 18 carbon atoms and cycloalkyl groups having 3 to 18 carbon atoms are preferred.２ When R is an alkyl group having 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 is a cycloalkyl group having 3 to 18 carbon atoms, it is preferably a cycloalkyl group having 3 to 8 carbon atoms, more preferably a cycloalkyl group having 5 to 7 carbon atoms, and even more preferably a cyclohexyl group. This further improves the flame retardant performance of the flame retardant of the present invention.

[0026] R in general formula (1) ３ ~R ６ Examples of the alkyl group having 1 to 4 carbon atoms represented by the formula (1) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. ３ ~R ６ As the alkyl group, a methyl group and an ethyl group are preferred, and a methyl group is more preferred, which further improves the flame retardancy of the flame retardant of the present invention.

[0027] R in general formula (2) ７ and R in general formula (3) ８ Examples of the divalent hydrocarbon group having 1 to 18 carbon atoms represented by the formula (I) include an alkylene group having 1 to 18 carbon atoms, an alkenylene group having 2 to 18 carbon atoms, a cycloalkylene group having 4 to 18 carbon atoms, and an arylene group having 6 to 18 carbon atoms.

[0028] Examples of the alkylene group having 1 to 18 carbon atoms include linear or branched alkylene groups such as methylene, ethylene, n-propylene, isopropylene, n-butylene, isobutylene, n-pentylene, isopentylene, n-hexylene, isohexylene, n-heptylene, isoheptylene, n-octylene, isooctylene, n-nonylene, isononylene, n-decylene, isodecylene, n-undecylene, isoundecylene, n-dodecylene, isododecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, and octadecylene.

[0029] Examples of the alkenylene group having 2 to 18 carbon atoms include linear or branched alkenylene groups such as vinylene group, 1-methylethenylene group, 2-methylethenylene group, propenylene group, butenylene group, isobutenylene group, pentenylene group, hexenylene group, heptenylene group, octenylene group, decenylene group, dodecenylene group, tetradecenylene group, hexadecenylene group, and octadecenylene group.

[0030] Examples of the cycloalkylene group having 4 to 18 carbon atoms include a cyclobutylene group, a cyclopentylene group, a 2-methylcyclopentylene group, a cyclohexylene group, a 1,3-dimethylcyclohexylene group, a cycloheptylene group, a 1-ethylcyclopentylene group, a cyclooctylene group, a cyclononylene group, a cyclodecylene group, a cycloundecylene group, a cyclododecylene group, a cyclotridene group, a cyclotetradecylene group, a cyclopentadecylene group, a cyclohexadecylene group, a cycloheptadecylene group, a cyclooctadecylene group, a norbornylene group, a dicyclopentylene group, an isopropylidenedicyclohexylene group, and a cyclohexanedimethylene group.

[0031] Examples of the arylene group having 6 to 18 carbon atoms include a phenylene group, a tolylene group, a xylylene group, a naphthylene group, a biphenylene group, a phenanthrylene group, a fluorenylene group, an indenylene group, an isopropylidenediphenylene group, and a dimethylenephenylene group.

[0032] R in general formula (2) ７ and R in general formula (3) ８ R is preferably a direct bond, an alkylene group having 1 to 18 carbon atoms, or an arylene group having 6 to 18 carbon atoms, and more preferably an alkylene group having 1 to 18 carbon atoms. ７ or R ８ When R is an alkylene group having 1 to 18 carbon atoms, the alkylene group is preferably an alkylene group having 2 to 14 carbon atoms, more preferably an alkylene group having 2 to 10 carbon atoms, and even more preferably an alkylene group having 4 to 8 carbon atoms. ７ or R ８is an arylene group having 6 to 18 carbon atoms, the arylene group is preferably an arylene group having 6 to 12 carbon atoms, more preferably an arylene group having 6 to 10 carbon atoms, and even more preferably a phenylene group. This further improves the flame retardant performance of the flame retardant of the present invention.

[0033] A conventionally known method can be used to produce the compound represented by general formula (1). For example, 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 general formula (4) may be combined and reacted with an alcohol having an N-alkyl-2,2,6,6-tetramethylpiperidinol skeleton. Specifically, direct esterification of an acid and an alcohol, a reaction between an acid halide and an alcohol, an ester exchange reaction, a urethane bond formation reaction between an isocyanate and an alcohol, and the like are possible. Alternatively, for example, 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 general formula (4) may be combined and reacted with an alcohol having an N—H-2,2,6,6-tetramethylpiperidinol skeleton, followed by N-alkylation using an alkyl halide or the like. The compounds obtained by the above-mentioned methods may be further separated and purified, if necessary, by separation and purification means such as filtration, concentration, distillation, extraction, crystallization, recrystallization, adsorption, and column chromatography, or a combination of these means.

[0034] The hindered amine compound (A) may be used alone, and R １ ~R ６ Two or more compounds having different groups may be used in combination.

[0035] Specific examples of the compound represented by general formula (1) include the following compounds No. 1 to No. 16. These compounds may be used alone or in combination of two or more.

[0036]

[0037]

[0038] In the present invention, from the viewpoint of excellent flame retardancy, Compounds No. 2 to No. 13 are preferred, Compounds No. 2, No. 3, No. 4, No. 5, No. 6, No. 8, and No. 9 are more preferred, and Compounds No. 3, No. 4, and No. 5 are even more preferred.

[0039] When the flame retardant of the present invention does not contain a phosphorus-based flame retardant (B) described below, the content of the hindered amine compound (A) in the flame retardant of the present invention is preferably 50 parts by mass or more, more preferably 80 parts by mass or more, and even more preferably 90 parts by mass or more, per 100 parts by mass of the flame retardant, which allows the flame retardant performance of the hindered amine compound (A) to be stably exhibited.

[0040] When the flame retardant of the present invention contains a phosphorus-based flame retardant (B) described below, the content of the hindered amine compound (A) in the flame retardant of the present invention is preferably 2 parts by mass or more, 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 flame retardant. This allows the flame retardant performance of the hindered amine compound (A) to be stably exhibited. On the other hand, when the flame retardant of the present invention contains a phosphorus-based flame retardant (B), the content of the hindered amine compound (A) is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less, per 100 parts by mass of the flame retardant. This allows the flame retardancy-improving effect achieved by using the hindered amine compound (A) and the phosphorus-based flame retardant (B) in combination to be fully obtained.

[0041] The flame retardant of the present invention preferably contains (B) a phosphorus-based flame retardant. This further improves the flame retardancy of the flame retardant of the present invention. The (B) phosphorus-based flame retardant is not particularly limited as long as it is a flame retardant containing phosphorus, and those obtained by conventionally known methods or commercially available products can be used.

[0042] Examples of (B) phosphorus-based flame retardants include phosphate ester-based flame retardants, phosphonate ester-based flame retardants, phosphinate ester-based flame retardants, metal phosphinate salt-based flame retardants, phosphazene-based flame retardants, phosphate-based flame retardants, and red phosphorus.

[0043] Examples of the phosphate ester-based flame retardant include triaryl phosphate esters such as triphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, cresyl diphenyl phosphate, xylyl diphenyl phosphate, cresyl bis(2,6-xylenyl)phosphate, and 2-ethylhexyl diphenyl phosphate; aromatic phosphate esters or polycondensates thereof such as 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), and 4,4'-biphenol bis(2,6-xylenyl phosphate); and haloalkyl phosphate esters such as tris(chloroethyl)phosphate, tris(chloropropyl)phosphate, tris(dichloropropyl)phosphate, and tris(tribromopropyl)phosphate.

[0044] Examples of the phosphonate ester-based flame retardant include divinyl phenylphosphonate, diallyl phenylphosphonate, 1-butenyl phenylphosphonate, pentaerythritol bis(methyl phosphonate), pentaerythritol bis(benzyl phosphonate), 10-phenoxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, and 6,6'-(1,3-phenylenebis(oxy))bis(6H-dibenz[c,e][1,2]oxaphosphorine)-6,6'-dioxide.

[0045] Examples of the phosphinate ester flame retardant include phenyl diphenylphosphinate, methyl diphenylphosphinate, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (hereinafter also referred to as DOPO), DOPO derivatives, and the like. Examples of the DOPO derivatives include 10-benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(2,5-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(2,7-dihydroxynaphthyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, and 6,6'-(1,2-ethanediyl)bis(6H-dibenz[c,e][1,2]oxaphosphorine)-6,6'-dioxide.

[0046] Examples of the metal phosphinate flame retardant include aluminum diethylphosphinate, calcium diethylphosphinate, and zinc diethylphosphinate.

[0047] Examples of the phosphazene flame retardant include bis(2-allylphenoxy)phosphazene, dicresylphosphazene, propoxyphosphazene, phenoxyphosphazene, aminophosphazene, poly(fluoroalkylphosphazene), and dipropoxyphosphazene.

[0048] Examples of the phosphate-based flame retardant include melamine phosphate, melamine pyrophosphate, melamine polyphosphate, melam polyphosphate, ammonium phosphate, ammonium pyrophosphate, ammonium polyphosphate, piperazine phosphate, piperazine pyrophosphate, and piperazine polyphosphate.

[0049] As the (B) phosphorus-based flame retardant, from the viewpoint of improving flame retardancy, a phosphate ester-based flame retardant, a phosphonate ester-based flame retardant, a phosphinate ester-based flame retardant, and a metal phosphinate-based flame retardant are preferred, and a phosphonate ester-based flame retardant and a phosphinate ester-based flame retardant are more preferred.

[0050] When a phosphonate ester flame retardant is used as the (B) phosphorus-based flame retardant, pentaerythritol bis(methyl phosphonate), pentaerythritol bis(benzyl phosphonate), and 10-phenoxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide are preferred from the viewpoint of improving flame retardancy.

[0051] When a phosphinic acid ester flame retardant is used as the (B) phosphorus-based flame retardant, DOPO and DOPO derivatives are preferred from the viewpoint of improving flame retardancy, and 6,6'-(1,2-ethanediyl)bis(6H-dibenz[c,e][1,2]oxaphosphorine)-6,6'-dioxide is more preferred.

[0052] The phosphorus-based flame retardant (B) may be used alone or in combination of two or more different compounds. When two or more different phosphorus-based flame retardants are combined, from the viewpoint of improving flame retardancy, it is preferable to use two or more different phosphonate ester-based flame retardants in combination, a phosphonate ester-based flame retardant and a phosphate ester-based flame retardant in combination, or a phosphonate ester-based flame retardant and a metal phosphinate salt-based flame retardant in combination.

[0053] When the flame retardant of the present invention contains a (B) phosphorus-based flame retardant, the content of the (B) phosphorus-based flame retardant is preferably 10 parts by mass or more, more preferably 200 parts by mass or more, and even more preferably 300 parts by mass or more, relative to 100 parts by mass of the (A) hindered amine compound. This allows the flame retardancy improvement effect of the combined use of the (A) hindered amine compound and the (B) phosphorus-based flame retardant to be fully obtained. On the other hand, when the flame retardant of the present invention contains a (B) phosphorus-based flame retardant, the content of the (B) phosphorus-based flame retardant is preferably 5,000 parts by mass or less, more preferably 3,000 parts by mass or less, and even more preferably 1,500 parts by mass or less, relative to 100 parts by mass of the (A) hindered amine compound. This allows the flame retardant performance of the (A) hindered amine compound to be stably exhibited, and also reduces bleeding when blended into a resin.

[0054] The flame retardant of the present invention preferably contains (C) a nitrogen-based flame retardant in addition to (B) a phosphorus-based flame retardant. This further improves the flame retardancy of the flame retardant of the present invention. The (C) nitrogen-based flame retardant is not particularly limited as long as it is a flame retardant containing a nitrogen element, and those obtained by conventionally known methods and commercially available products can be used. However, those contained in (B) a phosphorus-based flame retardant are excluded.

[0055] Examples of the (C) nitrogen-based flame retardant include melamine, melamine cyanurate, poly-[2,4-(piperazin-1,4-yl)-6-(morpholino-4-yl)-1,3,5-triazine], melamine sulfate, guanidine sulfate, guanidine sulfamate, etc. As the (C) nitrogen-based flame retardant, one type of compound may be used alone, or two or more different types of compounds may be used in combination.

[0056] When the flame retardant of the present invention contains a nitrogen-based flame retardant (C), the content of the nitrogen-based flame retardant (C) is preferably 10 parts by mass or more, more preferably 200 parts by mass or more, and even more preferably 300 parts by mass or more, relative to 100 parts by mass of the hindered amine compound (A). This allows the flame retardancy improvement effect achieved by the combined use of the hindered amine compound (A), the phosphorus-based flame retardant (B), and the nitrogen-based flame retardant (C) to be fully obtained. On the other hand, when the flame retardant of the present invention contains a nitrogen-based flame retardant (C), the content of the nitrogen-based flame retardant (C) is preferably 4,000 parts by mass or less, more preferably 2,000 parts by mass or less, and even more preferably 1,000 parts by mass or less, relative to 100 parts by mass of the hindered amine compound (A). This allows the flame retardant performance of the hindered amine compound (A) to be stably exhibited, and also reduces bleeding when blended into a resin.

[0057] When the flame retardant of the present invention contains a nitrogen-based flame retardant (C), the content of the nitrogen-based flame retardant (C) is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, and even more preferably 30 parts by mass or more, per 100 parts by mass of the phosphorus-based flame retardant (B). This allows the flame retardancy improvement effect achieved by the combined use of the hindered amine compound (A), the phosphorus-based flame retardant (B), and the nitrogen-based flame retardant (C) to be fully obtained. On the other hand, when the flame retardant of the present invention contains a nitrogen-based flame retardant (C), the content of the nitrogen-based flame retardant (C) is preferably 700 parts by mass or less, more preferably 300 parts by mass or less, and even more preferably 200 parts by mass or less, per 100 parts by mass of the phosphorus-based flame retardant (B). This allows the flame retardant performance of the hindered amine compound (A) to be stably exhibited.

[0058] <Composition> The composition of the present invention contains the flame retardant and a synthetic resin. The flame retardant of the present invention can be blended with a synthetic resin, particularly preferably a thermoplastic resin, and used as a composition.

[0059] The content of the flame retardant in the composition of the present invention 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, and particularly preferably 1 part by mass or more, per 100 parts by mass of the composition. This allows the performance of the flame retardant to be fully exhibited. On the other hand, the content of the flame retardant is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of the composition. This reduces bleeding of the flame retardant component.

[0060] The content of the flame retardant in the composition of the present invention 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, and particularly preferably 0.1 parts by mass or more, per 100 parts by mass of synthetic resin. This allows the flame retardant to fully exhibit its performance. On the other hand, the content of the flame retardant is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of synthetic resin. This reduces bleeding of the flame retardant component.

[0061] Examples of the synthetic resin include thermoplastic resins such as polyolefin resins, styrene-based resins, polyester resins, polycarbonate resins, polysulfide resins, polyamide resins, polyether resins, and halogen-containing resins.

[0062] Examples of the polyolefin resin include polyethylene-based resins such as low-density polyethylene, linear low-density polyethylene, high-density polyethylene, cross-linked polyethylene, and ultra-high molecular weight polyethylene; polypropylene-based resins such as homopolypropylene, random copolymer polypropylene, block copolymer polypropylene, impact copolymer polypropylene, high-impact copolymer polypropylene, and maleic anhydride-modified polypropylene; α-olefin polymers such as polybutene-1, cycloolefin polymer, poly-3-methyl-1-butene, poly-3-methyl-1-pentene, and poly-4-methyl-1-pentene; and α-olefin copolymers such as ethylene-methyl methacrylate copolymer and ethylene-vinyl acetate copolymer.

[0063] The melt flow rate (hereinafter also referred to as MFR) of these polyolefin resins is preferably 0.05 g / 10 min or more, more preferably 0.5 g / 10 min or more, and even more preferably 0.8 g / 10 min or more, from the viewpoint of improving flame retardancy. Furthermore, the MFR of these polyolefin resins is preferably 30 g / 10 min or less, more preferably 20 g / 10 min or less, and even more preferably 15 g / 10 min or less, from the viewpoint of improving flame retardancy. The MFR here is a value measured in accordance with JIS K 7210.

[0064] Examples of the styrene resin include syndiotactic polystyrene and acrylonitrile-butadiene-styrene terpolymer. Examples of the polysulfide resin include polyphenylene sulfide. Examples of the polyamide resin include polyhexamethylene adipamide.

[0065] Examples of the polyester resin include polyalkylene terephthalates such as polyethylene terephthalate, polybutylene terephthalate, polytetramethylene terephthalate, and polycyclohexanedimethylene terephthalate; polyalkylene naphthalates such as polyethylene naphthalate and polybutylene naphthalate; and degradable aliphatic polyesters such as polyhydroxybutyrate, polycaprolactone, polybutylene succinate, polyethylene succinate, polylactic acid, polymalic acid, polyglycolic acid, polydioxane, and poly(2-oxetanone).

[0066] The polycarbonate resin is a resin having a carbonate bond, and is obtained, for example, by a polymerization reaction between a divalent hydroxy aromatic compound and a carbonate precursor. Examples of the divalent hydroxy aromatic compound include dihydroxybenzenes such as resorcinol and hydroquinone; bishydroxyaryls 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; dihydroxyarylketones such as bis(4-hydroxyphenyl)ketone and bis(4-hydroxy-3-methylphenyl)ketone; 4,4'-dihydroxydiphenyl ether and 4,4'-dihydroxy-3,3'-dimethylphenyl ether. Examples of suitable carbonate precursors include dihydroxyaryl ethers such as 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, and 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfone; and phenolphthalein. These divalent hydroxy aromatic compounds may be used alone or in combination with two or more. Furthermore, they may be used in combination with a polyvalent hydroxy aromatic compound having three or more hydroxy groups. Specific examples of suitable carbonate precursors include phosgene, carbonic acid diesters, diphenyl carbonate, dihaloformates of dihydric phenols, and mixtures thereof.

[0067] Further examples of the synthetic resin 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.

[0068] 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.

[0069] Among these synthetic resins, from the viewpoint of enabling the flame retardant to exhibit its flame retardant properties more effectively, one or more selected from the group consisting of polyolefin resins, styrene-based resins, and copolymers thereof are preferred, polyolefin resins are more preferred, high-density polyethylene, low-density polyethylene, and linear low-density polyethylene are even more preferred, and it is also preferred to use any of these synthetic resins in combination with a thermoplastic elastomer.

[0070] These synthetic resins can be used regardless of molecular weight, degree of polymerization, polymerization method, density, softening point, proportion of insoluble matter in solvent, degree of stereoregularity, presence or absence of catalyst residue, types and blending ratios of raw material monomers, type of polymerization catalyst, etc. These synthetic resins may be used alone or in combination of two or more. Furthermore, the synthetic resins may be alloyed.

[0071] The content of the synthetic resin in the composition of the present invention is preferably 80 parts by mass or more, more preferably 85 parts by mass or more, and even more preferably 90 parts by mass or more, per 100 parts by mass of the composition. This allows the inherent physical properties of the synthetic resin to be fully exhibited. On the other hand, the content of the synthetic resin in the composition of the present invention is preferably 99.9 parts by mass or less, more preferably 99.7 parts by mass or less, even more preferably 99.5 parts by mass or less, and particularly preferably 99 parts by mass or less, per 100 parts by mass of the composition. This allows the composition of the present invention to contain the flame retardant in an amount necessary to exhibit flame retardant performance.

[0072] The composition of the present invention may contain other optional components in addition to the flame retardant, such as phenolic antioxidants, phosphorus-based antioxidants, thioether-based antioxidants, ultraviolet absorbers, and hindered amine-based light stabilizers, to stabilize the composition.

[0073] Examples of the phenolic antioxidant 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)propionic acid amide], 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-tert-butyl-m-cresol), 2,2'-ethylidenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(4-sec-butyl-6-tert-butylphenol), 1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane, 1,3,5-tris(2,6-dimethyl-3-hydroxy-4-tert-butylbenzyl)isocyanurate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(3,5-di-tert-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-hexamethylenebis[(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] diphenyl) propionate], bis[3,3-bis(4-hydroxy-3-tert-butylphenyl) butylic acid] glycol ester, bis[2-tert-butyl-4-methyl-6-(2-hydroxy-3-tert-butyl-5-methylbenzyl)phenyl] terephthalate, 1,3,5-tris[(3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxyethyl] isocyanurate, 3,9-bis[1,1-dimethyl-2-{(3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy}ethyl]-2,4,8,10-tetraoxaspiro[5,5]undecane, triethylene glycol bis[(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate], etc. These phenolic antioxidants may be used alone or in combination of two or more. From the viewpoint of antioxidant effect, the amount of the phenolic antioxidant added is preferably 0.001 to 10 parts by mass, more preferably 0.05 to 5 parts by mass, per 100 parts by mass of the synthetic resin.

[0074] Examples of the phosphorus-based antioxidants include trisnonylphenyl phosphite, tris(2,4-di-tert-butylphenyl)phosphite, tris[2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenylthio)-5-methylphenyl]phosphite, tridecyl phosphite, octyldiphenyl phosphite, didecyl monophenyl phosphite, bis(tridecyl)pentaerythritol diphosphite, bis(nonylphenyl)pentaerythritol diphosphite, tetritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4-dicumylphenyl)pentaerythritol diphosphite, tetrakis(tridecyl)isopropylidenediphenol diphosphite, tetrakis(tridecyl)-4, 4'-n-butylidenebis(2-tert-butyl-5-methylphenol) diphosphite, hexakis(tridecyl)-1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane triphosphite, tetrakis(2,4-di-tert-butylphenyl)biphenylene diphosphonite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 2,2'-methylenebis(4,6-tert-butylphenyl)-2-ethylhexyl phosphite Examples of phosphorus-based antioxidants include 2,2'-methylenebis(4,6-tert-butylphenyl)octadecylphosphite, 2,2'-ethylidenebis(4,6-di-tert-butylphenyl)fluorophosphite, tris(2-[(2,4,8,10-tetrakis-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-6-yl)oxy]ethyl)amine, and phosphite of 2-ethyl-2-butylpropylene glycol and 2,4,6-tri-tert-butylphenol. These phosphorus-based antioxidants may be used alone or in combination of two or more. From the viewpoint of antioxidant effect, the amount of phosphorus-based antioxidant added 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.

[0075] Examples of the thioether-based antioxidant include dialkyl thiodipropionates such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate, and pentaerythritol tetrakis(β-alkylmercaptopropionates). These thioether-based antioxidants may be used alone or in combination of two or more. From the viewpoint of antioxidant effect, the amount of the thioether-based antioxidant added 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.

[0076] Examples of the ultraviolet absorber 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-tert-butylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-3',5'- 2-(2'-hydroxyphenyl)benzotriazoles such as 2-(2'-hydroxy-5'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-dicumylphenyl)benzotriazole, 2,2'-methylenebis(4-tert-octyl-6-(benzotriazolyl)phenol), and 2-(2'-hydroxy-3'-tert-butyl-5'-carboxyphenyl)benzotriazole; phenyl salicylate benzoates such as 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, 2,4-di-tert-amylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, and 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-diphenylacrylate, methyl 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 alone or in combination of two or more.The amount of the ultraviolet absorber added is preferably 0.001 to 30 parts by mass, more preferably 0.05 to 10 parts by mass, per 100 parts by mass of the synthetic resin, from the viewpoint of ultraviolet absorption effect.

[0077] Examples of the hindered amine light stabilizer 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, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, 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-hydroxybenzyl)- polycondensation product of 1,6-bis(2,2,6,6-tetramethyl-4-piperidinol) / diethyl succinate, polycondensation product of 1,6-bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane / 2,4-dichloro-6-morpholino-s-triazine, polycondensation product of 1,6-bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane / 2,4-dichloro-6-tert-octylamino-s-triazine, polycondensation product of 1,5,8,12-tetrakis[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]hexane / 2,4-dichloro-6-tert-octylamino-s-triazine, 1,6,11-tris[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-s-triazin-6-yl]aminoundecane, 1,6,11-tris[2,4-bis(N-butyl-N-(1,2,2,6,6-tetramethyl-4-piperidyl)amino)-s-triazin-6-yl]aminoundecane, 1,6,11-tris[2,4-bis(N-butyl-N-(1,2,2,6,Examples of suitable hindered amine light stabilizers include bis(2,2,6,6-tetramethyl-1-octyloxy-4-piperidyl)amino)-s-triazin-6-yl)aminoundecane, bis(2,2,6,6-tetramethyl-1-octyloxy-4-piperidyl)decanedioate, bis(2,2,6,6-tetramethyl-1-undecyloxypiperidin-4-yl)carbonate, and TINUVINNOR 371 manufactured by BASF. These hindered amine light stabilizers may be used alone or in combination of two or more. From the viewpoint of light stabilization effect, the amount of the hindered amine light stabilizer added 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 the synthetic resin.

[0078] The composition of the present invention may further contain additives that are commonly used in synthetic resins, such as crosslinking agents, antistatic agents, antifogging agents, anti-plate-out agents, surface treatment agents, plasticizers, lubricants, reinforcing agents, nucleating agents, flame retardants other than those of the present invention, flame retardant assistants, fluorescent agents, antifungal agents, bactericides, foaming agents, metal deactivators, mold release agents, silicone oils, silane coupling agents, fillers, hydrotalcites, metal soaps, pigments, dyes, etc., as needed, provided that the effects of the present invention are not impaired.

[0079] The timing of mixing the flame retardant and other optional components with the synthetic resin is not particularly limited. For example, two or more selected from the compounding components other than the synthetic resin may be mixed in advance and then compounded with the synthetic resin, or each component other than the synthetic resin may be compounded sequentially with the synthetic resin. When multiple components are mixed in advance, each component may be crushed and then mixed, or mixed and then crushed. When the synthetic resin is an alloy, each component other than the synthetic resin may be added to a compound that has already been alloyed, or may be added during the alloying process.

[0080] The flame retardant and synthetic resin may be mixed by mixing the entire amount of the synthetic resin to be mixed with the flame retardant, or by pre-mixing a portion of the synthetic resin with the flame retardant to prepare a masterbatch, and then mixing the masterbatch with the remaining synthetic resin. The masterbatch may also contain the other optional components. The content of the flame retardant in the masterbatch may be 1 part by mass or more, and may be 10 to 90 parts by mass, per 100 parts by mass of the masterbatch.

[0081] The form of the composition of the present invention is not particularly limited, but from the viewpoint of the handleability of the composition, it is preferably in the form of pellets, powder, granules, or flakes, and more preferably in the form of pellets. The composition of the present invention can be used for molding, etc., alone or in combination with compositions other than the present invention, additive components, or mixtures thereof. The composition of the present invention can also be used as a masterbatch.

[0082] <Molded Article> The molded article of the present invention can be obtained by molding the composition of the present invention by a known method. The molding method is not particularly limited, and examples thereof include extrusion molding, calendar molding, injection molding, roll molding, compression molding, and blow molding. These molding methods can be used to produce molded articles of various shapes, such as resin plates, sheets, films, pellets, and irregularly shaped articles.

[0083] The composition of the present invention and molded articles thereof can be used in a wide range of industrial fields, including electricity, electronics, and communications, agriculture, forestry, and fisheries, mining, construction, food, textiles, clothing, medicine, coal, petroleum, rubber, leather, automobiles, precision instruments, wood, building materials, civil engineering, furniture, printing, and musical instruments. More specifically, the composition can be used in office automation equipment such as printers, personal computers, word processors, keyboards, PDAs (personal digital assistants), telephones, copiers, facsimiles, 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 tables; audio-visual equipment such as TVs, VTRs, video cameras, radio cassette players, tape recorders, minidiscs, CD players, speakers, and liquid crystal displays; and electrical and electronic components and communication equipment 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.

[0084] The composition of the present invention and molded articles thereof can also be used for optical materials such as optical disks, CD disks, DVD disks, and lenses, or as a replacement for glass.

[0085] Furthermore, the composition of the present invention and molded articles thereof are used in a variety of applications, including materials for automobiles, vehicles, ships, aircraft, buildings, houses, and construction, such as seats (padding, outer surface, etc.), belts, ceiling coverings, convertible tops, armrests, door trims, rear package trays, carpets, mats, sun visors, wheel covers, mattress covers, airbags, insulation materials, hand straps, hand straps, wire covering materials, electrical insulating materials, paints, coating materials, upholstery materials, flooring materials, partition walls, carpets, wallpaper, wall coverings, exterior materials, interior materials, roofing materials, deck materials, wall materials, pillar materials, flooring boards, fence materials, frames and moldings, window and door profiles, shingles, paneling, terraces, balconies, soundproofing boards, heat insulating boards, and window materials; civil engineering materials, clothing, daily necessities and sporting goods, such as curtains, sheets, plywood, synthetic fiberboards, carpets, entrance mats, sheets, buckets, hoses, containers, eyeglasses, bags, cases, goggles, skis, rackets, tents, and musical instruments.

[0086] <Others> The present invention includes the following aspects: [1] A flame retardant containing (A) a hindered amine compound, wherein the (A) hindered amine compound is a compound represented by the following general formula (1):

[0087] In general formula (1), R １ represents a group represented by the following general formula (2), (3) or (4), and R ２ represents a hydrocarbon group having 1 to 18 carbon atoms, and R ３ ~R ６ each independently represents an alkyl group having 1 to 4 carbon atoms.

[0088] 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.

[0089] [2] R in general formula (1) １ is a group represented by general formula (2). [3] The flame retardant according to [1], ７ is an alkylene group having 2 to 14 carbon atoms. [4] The flame retardant according to any one of [1] to [3], further comprising (B) a phosphorus-based flame retardant. [5] The flame retardant according to [4], wherein the (B) phosphorus-based flame retardant is one or more selected from the group consisting of phosphate ester-based flame retardants, phosphonate ester-based flame retardants, phosphinate ester-based flame retardants, and metal phosphinate-based flame retardants. [6] The flame retardant according to [4] or [5], wherein the content of the (B) phosphorus-based flame retardant is 10 parts by mass or more and 5,000 parts by mass or less per 100 parts by mass of the (A) hindered amine compound. [7] The flame retardant according to any one of [4] to [6], wherein the (B) phosphorus-based flame retardant comprises two or more different compounds. [8] The flame retardant according to any one of [4] to [7], further comprising (C) a nitrogen-based flame retardant.

[0090] [9] A composition comprising the flame retardant according to any one of [1] to [8] and a synthetic resin.

[10] A molded article obtained from the composition according to [9].

[0091] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0092] [Examples 1 to 30, Comparative Examples 1 to 15] The components were mixed in the amounts shown in Tables 1 to 3, and melt-kneaded using a Toyo Seiki Seisakusho Co., Ltd. Laboplastomill μ connected to a twin-screw extruder (product name: 2D15W) at a melt temperature of 200°C and a screw speed of 25 rpm to obtain resin strands. The obtained resin strands were cut using a pelletizer to obtain pelletized compositions. Note that the amounts shown in Tables 1 and 2 are all based on parts by mass.

[0093] Details of the components in Tables 1 and 2 are shown below. LLDPE resin-1: Linear low-density polyethylene resin (manufactured by Japan Polyethylene Corporation, product name: UR952G, MFR (based on JIS K 7210, load 2.16 kg, temperature 190°C) = 5.0 g / 10 min) LLDPE resin-2: Linear low-density polyethylene resin (manufactured by Japan Polyethylene Corporation, product name: F30FG, MFR (based on JIS K 7210, load 2.16 kg, temperature 190°C) = 1.0 g / 10 min) (A)-1: Compound No. 2 (A)-2: Compound No. 3 (A)-3: Compound No. 5 (A)-4: Compound No. 6 (A)-5: Compound No. 7 (A)-6: Compound No. 8 (A)-7: Compound No. 9 (A)-8: The above compound No. 10 (A)-9: The above compound No. 12 (A)-10: The above compound No. 13 (A)-X1: tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate (A)-X2: polycondensate of dimethyl succinate and 4-hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine (A)-X3: N,N',4,7-tetrakis{4,6-bis[N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino]-1,3,5-triazin-2-yl}-4,7-diazadecane-1,10-diamine (A)-X4: bis(2,2,6,6-tetramethylpiperidyl)sebacate (B)-1: pentaerythritol bis(methylphosphonate) (B)-2: pentaerythritol bis(benzylphosphonate) (B)-3: 10-phenoxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (B)-4: 6,6'-(1,2-ethanediyl)bis(6H-dibenz[c,e][1,2]oxaphosphorine)-6,6'-dioxide (B)-5: Polycondensation product of hydroquinone bis(diphenyl phosphate) (B)-6: Polycondensation product of bisphenol A bis(diphenyl phosphate) (B)-7: Polycondensation product of 4,4'-biphenol bis(diphenyl phosphate) (B)-8: Resorcinol bis(2,6-xylenyl phosphate), (B)-9: aluminum diethylphosphinate (C)-1: melamine cyanurate, antioxidant 1: stearyl (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, antioxidant 2: tris(2,4-di-tert-butylphenyl) phosphite,

[0094]

[0095]

[0096]

[0097]

[0098] <Production of Test Pieces> A 200 μm thick cast film was produced using the pellet-shaped composition obtained above. The film was produced using a device consisting of a Laboplastomill μ manufactured by Toyo Seiki Seisakusho Co., Ltd., connected to a single-screw extruder (product name: D1220B) and a T-die (product name: MT60B), under conditions of a melt temperature of 200°C, a screw speed of 30 rpm, a T-die extrusion temperature of 200°C, a chill roll temperature of 60°C, and a roll rotation speed of 0.40 to 0.45 rpm. 25 cm x 5 cm test pieces and 20 cm x 5 cm test pieces were cut from the obtained film and left to stand at 23±2°C and 50±5% RH for 48 hours, after which the flame retardancy was evaluated as follows.

[0099] <Flame Retardancy Evaluation: Horizontal Burning Test> The 25 cm x 5 cm test specimen obtained above was held horizontally, and a Bunsen burner with an inner diameter of 9.5 mm and a flame length of 38 mm was used as the heat source. A flame was applied to the center of the short side of the test specimen for 15 seconds, and the burning distance in the long side direction and the burning time until the flame went out were measured. The burning rate was calculated from the burning distance and the burning time. Measurements were made for each test specimen (n = 3), and the average value was calculated. The better the flame retardancy, the shorter the burning distance and the slower the burning rate. The results are shown in Tables 1 and 2.

[0100] <Flame Retardancy Evaluation: UL-94VTM> The test specimen prepared above was rolled into a cylindrical shape so that the bottom ends did not overlap, and the bottom 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 flame was applied to the bottom end of the test specimen for 3 seconds, and the number of seconds it took to burn was measured. After the flame was extinguished, the flame was applied again for 3 seconds, and the number of seconds it took to burn was measured. Flame retardancy was evaluated according to the evaluation criteria of VTM-0, VTM-1, and VTM-2, and the test specimen that met the lowest standard out of the five measurements (n = 5) was used as the evaluation rank for the resin composition. Test specimens that did not meet any of the VTM-0 to VTM-2 ranks were rated Not V. The results are shown in Tables 1 and 2.

[0101] <Evaluation of Bleeding Resistance> The film obtained above was cut into a size of 30 mm x 40 mm and left to stand at 23±2°C and 50±5% RH for 240 hours. Thereafter, the film surface was visually observed, and the bleed resistance was evaluated according to the following evaluation criteria. If the evaluation result was A or B, it was determined that there was no problem in practical use. The results are shown in Tables 1 and 2. A: No bleeding was observed. B: Slight bleeding was observed, but there was no problem in practical use. C: Bleeding was clearly observed, and the film was not suitable for practical use.

[0102]

[0103] Table 1 shows the evaluation results of the combustion test of test pieces containing LLDPE resin and a hindered amine compound. In the horizontal combustion test, the flame did not go out until the test piece was completely burned out for the test piece not containing a flame retardant (Comparative Example 1) and the test piece containing a compound of the present invention having a structure different from that of general formula (1). On the other hand, the test pieces containing the compound of the present invention represented by general formula (1) (Examples 1 to 16) had a shorter burning distance and a slower burning rate than the test pieces of Comparative Examples 1 to 5.

[0104]

[0105] Table 2 shows the evaluation results of the combustion test of test pieces containing LLDPE resin, a hindered amine compound, and a phosphorus-based flame retardant. When used in combination with a phosphorus-based flame retardant, the test pieces containing the compound represented by general formula (1) of the present invention (Examples 17 to 30) were superior in burning distance and burning rate in the horizontal burning test, and in the UL-94VTM evaluation rank, compared to the test pieces containing compounds having a structure different from that of general formula (1) of the present invention (Comparative Examples 6 to 15).

[0106]

[0107] Table 3 shows the results of the combustion test of test specimens containing an LLDPE resin with a different MFR from the LLDPE resin used in Tables 1 and 2, a hindered amine compound, a phosphorus-based flame retardant, and a nitrogen-based flame retardant. Test specimens containing the compound represented by general formula (1) of the present invention and a phosphorus-based flame retardant (Examples 31, 43, and 44) ​​had superior burning distances, burning rates, and UL-94 VTM evaluation ranks in the horizontal burning test compared to test specimens containing only a phosphorus-based flame retardant (Comparative Examples 17 to 27). Furthermore, test specimens containing the compound represented by general formula (1) of the present invention and two phosphorus-based flame retardants with different structures (Examples 32 to 39 and 45 to 47), as well as test specimens containing the compound represented by general formula (1) of the present invention, a phosphorus-based flame retardant, and a nitrogen-based flame retardant (Examples 40 to 42 and 48), had even superior burning distances, burning rates, and UL-94 VTM evaluation ranks in the horizontal burning test.

[0108] The above results demonstrate that the flame retardant of the present invention imparts excellent flame retardancy to resins.

Claims

1. A flame retardant comprising (A) a hindered amine compound, wherein the (A) hindered amine compound is a compound represented by the following general formula (1): In general formula (1), R １ represents a group represented by the following general formula (2), (3) or (4), R ２ represents a hydrocarbon group having 1 to 18 carbon atoms; R ３ ~R ６ each 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 formulae (2), (3) and (4), * represents a bond.

2. R in general formula (1) １ The flame retardant according to claim 1 , wherein 3. R ​​in general formula (2) ７ The flame retardant according to claim 2, wherein is an alkylene group having 2 to 14 carbon atoms.

4. The flame retardant according to claim 1, further comprising (B) a phosphorus-based flame retardant.

5. The flame retardant according to claim 4, wherein (B) the phosphorus-based flame retardant is one or more selected from the group consisting of phosphate ester-based flame retardants, phosphonate ester-based flame retardants, phosphinate ester-based flame retardants, and metal phosphinate-based flame retardants.

6. The flame retardant according to claim 4, wherein the content of the phosphorus-based flame retardant (B) is 10 parts by mass or more and 5,000 parts by mass or less per 100 parts by mass of the hindered amine compound (A).

7. The flame retardant according to claim 4, wherein (B) the phosphorus-based flame retardant comprises two or more different compounds.

8. The flame retardant according to claim 4, further comprising (C) a nitrogen-based flame retardant.

9. A composition comprising the flame retardant according to any one of claims 1 to 8 and a synthetic resin.

10. A molded article obtained from the composition according to claim 9.

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