JP6837149B2 - Granular UV absorber and resin composition - Google Patents
Granular UV absorber and resin composition Download PDFInfo
- Publication number
- JP6837149B2 JP6837149B2 JP2019538286A JP2019538286A JP6837149B2 JP 6837149 B2 JP6837149 B2 JP 6837149B2 JP 2019538286 A JP2019538286 A JP 2019538286A JP 2019538286 A JP2019538286 A JP 2019538286A JP 6837149 B2 JP6837149 B2 JP 6837149B2
- Authority
- JP
- Japan
- Prior art keywords
- sieve
- ultraviolet absorber
- granular
- carbon atoms
- tert
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000006096 absorbing agent Substances 0.000 title claims description 35
- 239000011342 resin composition Substances 0.000 title claims description 30
- -1 triazine compound Chemical class 0.000 claims description 217
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 35
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 31
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 14
- 229920003002 synthetic resin Polymers 0.000 claims description 14
- 239000000057 synthetic resin Substances 0.000 claims description 14
- 238000004458 analytical method Methods 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 13
- 238000009826 distribution Methods 0.000 claims description 11
- 238000005259 measurement Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 120
- 125000000217 alkyl group Chemical group 0.000 description 53
- 239000010408 film Substances 0.000 description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 28
- 229920005989 resin Polymers 0.000 description 26
- 239000011347 resin Substances 0.000 description 26
- 239000000463 material Substances 0.000 description 25
- 239000000975 dye Substances 0.000 description 21
- 239000000843 powder Substances 0.000 description 20
- 239000000049 pigment Substances 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 17
- 125000003342 alkenyl group Chemical group 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 16
- 239000003063 flame retardant Substances 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 229910019142 PO4 Inorganic materials 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000003822 epoxy resin Substances 0.000 description 13
- 239000008187 granular material Substances 0.000 description 13
- 235000021317 phosphate Nutrition 0.000 description 13
- 229920000647 polyepoxide Polymers 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 10
- 125000002877 alkyl aryl group Chemical group 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 238000004898 kneading Methods 0.000 description 10
- 238000000465 moulding Methods 0.000 description 10
- 239000010452 phosphate Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 238000002834 transmittance Methods 0.000 description 10
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- 150000002148 esters Chemical group 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 239000000314 lubricant Substances 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 239000002216 antistatic agent Substances 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 229920002725 thermoplastic elastomer Polymers 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 6
- 229910021536 Zeolite Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- 239000012756 surface treatment agent Substances 0.000 description 6
- 150000003918 triazines Chemical class 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000010457 zeolite Substances 0.000 description 6
- 239000006057 Non-nutritive feed additive Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 229920005668 polycarbonate resin Polymers 0.000 description 5
- 239000004431 polycarbonate resin Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 235000010356 sorbitol Nutrition 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 239000003429 antifungal agent Substances 0.000 description 4
- 229940121375 antifungal agent Drugs 0.000 description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000004088 foaming agent Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 4
- 239000012788 optical film Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005033 polyvinylidene chloride Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 238000007873 sieving Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- WMVJWKURWRGJCI-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)phenol Chemical group CCC(C)(C)C1=CC=C(O)C(C(C)(C)CC)=C1 WMVJWKURWRGJCI-UHFFFAOYSA-N 0.000 description 3
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 3
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 239000006081 fluorescent whitening agent Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
- 239000000347 magnesium hydroxide Substances 0.000 description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 3
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
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- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/48—Stabilisers against degradation by oxygen, light or heat
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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Description
本発明は、粒状紫外線吸収剤および樹脂組成物に関する。 The present invention relates to granular UV absorbers and resin compositions.
これまで紫外線吸収剤において様々な開発がなされてきた。この種の技術として、例えば、特許文献1に記載の技術が知られている。特許文献1には、紫外線吸収剤として、晶析により得られたトリアジン系化合物を使用することが記載されている(特許文献1の段落0102等)。 So far, various developments have been made in UV absorbers. As a technique of this kind, for example, the technique described in Patent Document 1 is known. Patent Document 1 describes that a triazine-based compound obtained by crystallization is used as an ultraviolet absorber (paragraph 0102 of Patent Document 1, etc.).
しかしながら、本発明者が検討した結果、上記特許文献1に記載の紫外線吸収剤において、粉体特性の点で改善の余地があることが判明した。 However, as a result of the examination by the present inventor, it has been found that there is room for improvement in the powder characteristics of the ultraviolet absorber described in Patent Document 1.
本発明者はさらに検討したところ、トリアジン系化合物を含有する粒状紫外線吸収剤の粉体特性について、篩分に基づく粒度分布を指針とすることにより適切に制御できることを見出した。このような知見に基づきさらに鋭意研究したところ、目開き4.0mm篩、目開き2.8mm篩、目開き2.0mm篩、及び目開き1.0mm篩の各篩残分量を所定の数値範囲内とすることにより、上記粒状紫外線吸収剤における粉体特性が改善されることを見出し、本発明を完成するに至った。 As a result of further studies, the present inventor has found that the powder characteristics of the granular ultraviolet absorber containing a triazine-based compound can be appropriately controlled by using the particle size distribution based on sieving as a guideline. As a result of further diligent research based on these findings, the residual amount of each sieve of 4.0 mm mesh sieve, 2.8 mm mesh sieve, 2.0 mm mesh sieve, and 1.0 mm mesh sieve is within a predetermined numerical range. It has been found that the powder properties of the above-mentioned granular ultraviolet absorber are improved by setting the content to the inside, and the present invention has been completed.
本発明によれば、
トリアジン系化合物を含む粒状紫外線吸収剤であって、
前記トリアジン系化合物が、下記化合物No.1を含み、
下記篩残分量の測定手順を実施したとき、当該粒状紫外線吸収剤を目開き5.0mm篩に通した際の不通過分量が0wt%であり、
下記篩残分量の測定手順を実施したとき、当該粒状紫外線吸収剤の目開き1.0mm篩の通過分量が1.0wt%以上15.0wt%以下であり、
下記の篩残分量の測定手順に基づいて算出される、
目開き4.0mmの篩上の篩残分量が、0.3wt%以上1.5wt%以下であり、
目開き2.8mmの篩上の篩残分量が、5.0wt%以上25.0wt%以下であり、
目開き2.0mmの篩上の篩残分量が、25.0wt%以上35.0wt%以下であり、
目開き1.0mmの篩上の篩残分量が、35.0wt%以上55.0wt%以下である、という粒度分布を満たす、粒状紫外線吸収剤が提供される。
(篩残分量の測定手順)
当該粒状紫外線吸収剤の所定量(g)を、目開き4.0mm篩、目開き2.8mm篩、目開き2.0mm篩、及び目開き1.0mm篩を用いて、この順で篩分を行い、各篩上に残存した当該粒状紫外線吸収剤の残存重量(g)を測定し、前記所定量に対する前記残存重量の重量割合(wt%)を篩残分量として算出する。
According to the present invention
A granular UV absorber containing a triazine compound.
The triazine-based compound is the following compound No. Including 1
When the following procedure for measuring the residual amount of the sieve was carried out, the amount of non-passing when the granular ultraviolet absorber was passed through a 5.0 mm sieve with a mesh size was 0 wt%.
When the following procedure for measuring the residual amount of the sieve was carried out, the amount of the granular ultraviolet absorber passing through the 1.0 mm mesh sieve was 1.0 wt% or more and 15.0 wt% or less.
Calculated based on the following procedure for measuring the amount of sieve residue,
The residual amount of the sieve on the sieve having a mesh size of 4.0 mm is 0.3 wt% or more and 1.5 wt% or less.
The residual amount of the sieve on the sieve having a mesh size of 2.8 mm is 5.0 wt% or more and 25.0 wt% or less.
The amount of sieve residue on the sieve having a mesh size of 2.0 mm is 25.0 wt% or more and 35.0 wt% or less.
Provided is a granular ultraviolet absorber that satisfies a particle size distribution in which the amount of residual sieve residue on a sieve having a mesh size of 1.0 mm is 35.0 wt% or more and 55.0 wt% or less.
(Measurement procedure for sieve residue)
A predetermined amount (g) of the granular ultraviolet absorber is sieved in this order using a 4.0 mm mesh sieve, a 2.8 mm mesh sieve, a 2.0 mm mesh sieve, and a 1.0 mm mesh sieve. Is performed, the residual weight (g) of the granular ultraviolet absorber remaining on each sieve is measured, and the weight ratio (wt%) of the residual weight to the predetermined amount is calculated as the sieve residual amount.
また本発明によれば、上記粒状紫外線吸収剤を含有する、樹脂組成物が提供される。 Further, according to the present invention, there is provided a resin composition containing the above-mentioned granular ultraviolet absorber.
本発明によれば、粉体特性に優れた粒状紫外線吸収剤およびそれを用いた樹脂組成物が提供される。 According to the present invention, a granular ultraviolet absorber having excellent powder properties and a resin composition using the same are provided.
上述した目的、およびその他の目的、特徴および利点は、以下に述べる好適な実施の形態、およびそれに付随する以下の図面によってさらに明らかになる。 The above-mentioned objectives and other objectives, features and advantages will be further clarified by the preferred embodiments described below and the accompanying drawings below.
本実施形態の粒状紫外線吸収剤は、トリアジン系化合物を含有するものである。
当該トリアジン系化合物は、下記一般式(I)で表される化合物を含有することが好ましい。これらを単独で用いても2種以上を組み合わせて用いてもよい。
なお、粒状紫外線吸収剤は下記トリアジン系化合物のみで構成されていてもよい。The granular ultraviolet absorber of the present embodiment contains a triazine-based compound.
The triazine-based compound preferably contains a compound represented by the following general formula (I). These may be used alone or in combination of two or more.
The granular ultraviolet absorber may be composed only of the following triazine compounds.
上記一般式(I)中、
R1は、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、炭素原子数3〜20のシクロアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアルキルアリール基、炭素原子数7〜20のアリールアルキル基、炭素原子数2〜8のアルケニル基、又は下記一般式(II)で表される置換基を表し、
R2及びR3は、それぞれ独立に、水素原子、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、または−O−Rを表し、このRは、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、炭素原子数3〜20のシクロアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアルキルアリール基、又は炭素原子数7〜20のアリールアルキル基を表し、
R4、R5、R6、R7、R8、R9、R10、R11及びR12は、それぞれ独立に、水素原子、ハロゲン原子、置換又は無置換の、直鎖又は分岐の炭素原子数1〜8のアルキル基又は直鎖又は分岐の炭素原子数2〜8のアルケニル基を表し、
R13及びR14は、それぞれ独立に、水素原子またはヒドロキシ基を表す。In the above general formula (I),
R 1 is a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 carbon atoms. Represents an alkylaryl group of ~ 20, an arylalkyl group having 7 to 20 carbon atoms, an alkenyl group having 2-8 carbon atoms, or a substituent represented by the following general formula (II).
R 2 and R 3 independently represent a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or −OR, and this R is substituted or absent. Substituent linear or branched alkyl groups with 1 to 20 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, alkylaryl groups with 7 to 20 carbon atoms, Alternatively, it represents an arylalkyl group having 7 to 20 carbon atoms.
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are independently hydrogen atoms, halogen atoms, substituted or unsubstituted, linear or branched carbons. Represents an alkyl group with 1 to 8 atoms or a linear or branched alkenyl group with 2 to 8 carbon atoms.
R 13 and R 14 each independently represent a hydrogen atom or a hydroxy group.
ただし、R1、R2、R3及びRで表される置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、R4、R5、R6、R7、R8、R9、R10、R11及びR12で表される置換又は無置換の、直鎖又は分岐の炭素原子数1〜8のアルキル基中のメチレン基は、酸素原子、硫黄原子、炭素−炭素二重結合、−CO−、−CO−O−、−OC−O−、−CO−NH−、−NH−CO−、−CR01=N−および−N=CR02−から選択される少なくとも一以上の構造で置換されていてもよく、前記構造中のR01及びR02は、それぞれ独立に、直鎖又は分岐の炭素原子数1〜8のアルキル基を表す。However, substituted or unsubstituted, linear or branched alkyl groups having 1 to 20 carbon atoms represented by R 1 , R 2 , R 3 and R, R 4 , R 5 , R 6 , R 7 , R. The methylene groups in the substituted or unsubstituted, linear or branched alkyl groups having 1 to 8 carbon atoms represented by 8 , R 9 , R 10 , R 11 and R 12 are oxygen atoms, sulfur atoms, and carbon atoms. -Carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-CO-, -CR 01 = N- and -N = CR 02- It may be substituted with at least one structure, and R 01 and R 02 in the structure each independently represent a linear or branched alkyl group having 1 to 8 carbon atoms.
上記一般式(II)中、
R21及びR22は、それぞれ独立に、水素原子、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、または−O−Rを表し、このRは、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、炭素原子数3〜20のシクロアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアルキルアリール基、又は炭素原子数7〜20のアリールアルキル基を表し、
R23、R24、R25、R26、R27、R28、R29、R30及びR31は、それぞれ独立に、水素原子、ハロゲン原子、置換又は無置換の、直鎖又は分岐の炭素原子数1〜8のアルキル基、又は直鎖または分岐の炭素原子数2〜8のアルケニル基を表し、
R32及びR33は、それぞれ独立に、水素原子またはヒドロキシ基を表し、
X1は、置換又は無置換の、直鎖又は分岐の炭素原子数8以上30以下のアルキレン基を表し、
Y1及びY2は、それぞれ独立に、−CO−O−、−O−CO−、−L1−、−O−L1O−、−O−L1−、−L1−O−CO−、−L1−CO−O−、−CO−CH=CH−、−CH=CH−CO−、−CH=CH−CO−O−、−CH=CH−O−CO−、−CO−O−CH=CH−を表し、
L1は、直鎖又は分岐の炭素原子数1〜8のアルキレン基であり、
m及びnは、それぞれ独立に、0〜8の整数を表し、
*は、式(I)中のR1と連結する酸素原子との結合手を表す。In the above general formula (II),
R 21 and R 22 independently represent a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or −OR, and this R is substituted or absent. Substituent linear or branched alkyl groups with 1 to 20 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, alkylaryl groups with 7 to 20 carbon atoms, Alternatively, it represents an arylalkyl group having 7 to 20 carbon atoms.
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 are independently hydrogen atoms, halogen atoms, substituted or unsubstituted, linear or branched carbons, respectively. Represents an alkyl group with 1 to 8 atoms, or a linear or branched alkenyl group with 2 to 8 carbon atoms.
R 32 and R 33 independently represent a hydrogen atom or a hydroxy group, respectively.
X 1 represents a substituted or unsubstituted, linear or branched alkylene group having 8 or more and 30 or less carbon atoms.
Y 1 and Y 2 each independently, -CO-O -, - O -CO -, - L 1 -, - O-L 1 O -, - O-L 1 -, - L 1 -O-CO -, -L 1- CO-O-, -CO-CH = CH-, -CH = CH-CO-, -CH = CH-CO-O-, -CH = CH-O-CO-, -CO- Represents O-CH = CH-
L 1 is a linear or branched alkylene group having 1 to 8 carbon atoms.
m and n each independently represent an integer from 0 to 8.
* Represents a bond with an oxygen atom connected to R 1 in the formula (I).
ただし、R21、R22及びRで表される置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、R23、R24、R25、R26、R27、R28、R29、R30及びR31で表される置換又は無置換の、直鎖又は分岐の炭素原子数1〜8のアルキル基およびX1で表される直鎖又は分岐の炭素原子数8以上30以下のアルキレン基中のメチレン基は、酸素原子、硫黄原子、炭素−炭素二重結合、−CO−、−CO−O−、−OC−O−、−CO−NH−、−NH−CO−、−CR03=N−および−N=CR04−から選択される少なくとも一以上の構造で置換されていてもよく、R03及びR04は、それぞれ独立に、直鎖又は分岐の炭素原子数1〜8のアルキル基を表す。However, substituted or unsubstituted, linear or branched alkyl groups having 1 to 20 carbon atoms represented by R 21 , R 22 and R, R 23 , R 24 , R 25 , R 26 , R 27 , R. 28 , R 29 , R 30 and R 31 substituted or unsubstituted, linear or branched alkyl groups having 1 to 8 carbon atoms and linear or branched alkyl groups represented by X 1 having 8 carbon atoms. The methylene groups in the above 30 or less alkylene groups are oxygen atom, sulfur atom, carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-. It may be substituted with at least one structure selected from CO-, -CR 03 = N- and -N = CR 04- , where R 03 and R 04 are independently linear or branched carbons, respectively. Represents an alkyl group having 1 to 8 atoms.
上記一般式(I)中のR1、R2、R3、上記一般式(II)中のR21、R22及びRで表される、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、sec−ブチル、tert−ブチル、アミル、イソアミル、tert−アミル、ヘキシル、ヘプチル、n−オクチル、イソオクチル、tert−オクチル、2−エチルヘキシル、ノニル、イソノニル、デシル、ウンデシル、ドデシル等の直鎖又は分岐のアルキル基が挙げられる。Substituent or unsubstituted, linear or branched carbon atoms represented by R 1 , R 2 , R 3 in the general formula (I) and R 21 , R 22 and R in the general formula (II). Examples of the alkyl group of number 1 to 20 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, heptyl, n-octyl, isooctyl, and the like. Examples thereof include linear or branched alkyl groups such as tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, undecyl and dodecyl.
上記一般式(I)中のR1及びRで表される、炭素原子数3〜20のシクロアルキル基としては、例えば、シクロプロピル、シクロペンチル、シクロヘキシル、シクロヘプチル等が挙げられる。Examples of the cycloalkyl group having 3 to 20 carbon atoms represented by R 1 and R in the general formula (I) include cyclopropyl, cyclopentyl, cyclohexyl, and cycloheptyl.
上記一般式(I)中のR1及びRで表される、炭素原子数6〜20のアリール基としては、例えば、フェニル、ナフチル、2−メチルフェニル、3−メチルフェニル、4−メチルフェニル、4−ビニルフェニル、3−イソプロピルフェニル、4−イソプロピルフェニル、4−ブチルフェニル、4−イソブチルフェニル、4−tert−ブチルフェニル、4−ヘキシルフェニル、4−シクロヘキシルフェニル、4−オクチルフェニル、4−(2−エチルヘキシル)フェニル、2,3−ジメチルフェニル、2,4−ジメチルフェニル、2,5−ジメチルフェニル、2,6−ジメチルフェニル、3,4−ジメチルフェニル、3,5−ジメチルフェニル、2,4−ジ−tert−ブチルフェニル、2,5−ジ−tert−ブチルフェニル、2,6−ジ−tert−ブチルフェニル、2,4−ジ−tert−ペンチルフェニル、2,5−ジ−tert−アミルフェニル、2,5−ジ−tert−オクチルフェニル、ビフェニル、2,4,5−トリメチルフェニル等が挙げられ、The general formula (I) are represented in the R 1 and R, the aryl group having 6 to 20 carbon atoms, e.g., phenyl, naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-Vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4-( 2-Ethylhexyl) phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2, 4-Di-tert-butylphenyl, 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert- Examples thereof include amylphenyl, 2,5-di-tert-octylphenyl, biphenyl, 2,4,5-trimethylphenyl and the like.
上記一般式(I)中のR1及びRで表される、炭素原子数7〜20のアリールアルキル基としては、例えば、ベンジル、フェネチル、2−フェニルプロパン−2−イル、ジフェニルメチル等が挙げられる。The general formula (I) are represented in the R 1 and R, the aryl alkyl group having 7 to 20 carbon atoms, e.g., benzyl, phenethyl, 2-phenylpropan-2-yl, diphenylmethyl and the like can be mentioned Be done.
上記一般式(I)中のR1及びRで表される、炭素原子数7〜20のアルキルアリール基としては、上記アルキル基の一つの水素原子がアリール基で置換された基が挙げられ、アリール基としては、フェニル、クレジル、キシリル、2,6−キシリル、2,4,6−トリメチルフェニル、ブチルフェニル、ノニルフェニル、ビフェニル、ナフチル、アントラセニル等が挙げられる。The general formula (I) are represented in the R 1 and R, examples of the alkyl aryl group having 7 to 20 carbon atoms, groups in which one hydrogen atom is substituted by an aryl group of the above alkyl group, and Examples of the aryl group include phenyl, cresyl, xsilyl, 2,6-xsilyl, 2,4,6-trimethylphenyl, butylphenyl, nonylphenyl, biphenyl, naphthyl, anthracenyl and the like.
上記一般式(I)中のR4、R5、R6、R7、R8、R9、R10、R11及びR12並びに上記一般式(II)中のR23、R24、R25、R26、R27、R28、R29、R30及びR31で表されるハロゲン原子としては、例えば、フッ素、塩素、臭素、ヨウ素等が挙げられる。R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 in the general formula (I) and R 23 , R 24 , R in the general formula (II). Examples of the halogen atom represented by 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 include fluorine, chlorine, bromine and iodine.
上記一般式(I)中のR4、R5、R6、R7、R8、R9、R10、R11及びR12並びに上記一般式(II)中のR23、R24、R25、R26、R27、R28、R29、R30及びR31で表される、置換又は無置換の直鎖又は分岐の炭素原子数1〜8のアルキル基としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、sec−ブチル、tert−ブチル、アミル、イソアミル、tert−アミル、ヘキシル、ヘプチル、n−オクチル、イソオクチル、tert−オクチル、2−エチルヘキシル等が挙げられる。本実施形態の粒状紫外線吸収剤においては、炭素原子数1〜8のアルキル基が好ましい。R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 in the general formula (I) and R 23 , R 24 , R in the general formula (II). Examples of the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms represented by 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 include methyl. Examples thereof include ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, heptyl, n-octyl, isooctyl, tert-octyl and 2-ethylhexyl. In the granular ultraviolet absorber of the present embodiment, an alkyl group having 1 to 8 carbon atoms is preferable.
上記一般式(I)中のR1、R4、R5、R6、R7、R8、R9、R10、R11及びR12並びに上記一般式(II)中のR23、R24、R25、R26、R27、R28、R29、R30及びR31で表される、直鎖又は分岐の炭素原子数2〜8のアルケニル基としては、例えば、直鎖及び分岐のプロペニル、ブテニル、ペンテニル、ヘキセニル、ヘプテニル、オクテニルが不飽和結合の位置によらず挙げられる。R 1 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 in the general formula (I) and R 23 , R in the general formula (II) Examples of linear or branched alkenyl groups having 2 to 8 carbon atoms represented by 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 include linear and branched alkenyl groups. Propenyl, butenyl, pentenyl, hexenyl, heptenyl, and octenyl are listed regardless of the position of the unsaturated bond.
上記一般式(II)中のX1で表される、置換又は無置換の、直鎖又は分岐の炭素原子数8以上30以下のアルキレン基としては、メチレンが8以上30以下で連結したアルキレン基、あるいは、一部のメチレンの水素原子がアルキル基で置換したアルキレン基を表す。本実施形態の粒状紫外線吸収剤においては、炭素原子数8以上20以下のアルキレン基が好ましい。Represented by X 1 in the general formula (II), a substituted or unsubstituted alkylene group as a straight-chain or branched alkylene group having 8 to 30 carbon atoms, and the methylene linked with 8 to 30 Alternatively, it represents an alkylene group in which some methylene hydrogen atoms are substituted with an alkyl group. In the granular ultraviolet absorber of the present embodiment, an alkylene group having 8 to 20 carbon atoms is preferable.
上記一般式(II)において、L1で表される、直鎖又は分岐の炭素原子数1〜8のアルキレン基としては、例えば、メチレン、メチルメチレン、ジメチルメチレン、エチレン、プロピレン、イソプロピレン、ブチレン、イソブチレン、ペンチレン等が挙げられる。In the above general formula (II), examples of the linear or branched alkylene group having 1 to 8 carbon atoms represented by L 1 include methylene, methylmethylene, dimethylmethylene, ethylene, propylene, isopropylene and butylene. , Isobutylene, pentylene and the like.
上記トリアジン系化合物は、上記一般式(I)において、R5、R6、R8、R9、R11及びR12が水素原子である化合物を含有してもよい。
また、上記一般式(I)で表されるトリアジン系化合物の一例として、下記一般式(A)で表される化合物、または下記一般式(B)で表される化合物が挙げられる。The triazine-based compound may contain a compound in which R 5 , R 6 , R 8 , R 9 , R 11 and R 12 are hydrogen atoms in the above general formula (I).
Further, as an example of the triazine-based compound represented by the general formula (I), a compound represented by the following general formula (A) or a compound represented by the following general formula (B) can be mentioned.
また、本実施形態の粒状紫外線吸収剤は、下記一般式(A)で表される化合物を用いることができる。これらを単独で用いても2種以上を組み合わせて用いてもよい。 Further, as the granular ultraviolet absorber of the present embodiment, a compound represented by the following general formula (A) can be used. These may be used alone or in combination of two or more.
上記一般式(A)中、
RA1は、直鎖又は分岐の炭素原子数1〜12のアルキル基、炭素原子数3〜8のシクロアルキル基、直鎖又は分岐の炭素原子数3〜8のアルケニル基、炭素原子数6〜18のアリール基、炭素原子数7〜18のアルキルアリール基または炭素原子数7〜18のアリールアルキル基を表し、
RA2及びRA3は、互いに同一でも異なっていてもよく、水素原子、直鎖又は分岐の炭素原子数1〜12のアルキル基、若しくは、直鎖又は分岐の炭素原子数1〜12のアルコキシ基を表し、
RA4、RA7、RA10は、互いに同一でも異なっていてもよく、水素原子、直鎖又は分岐の炭素原子数1〜8のアルキル基または直鎖又は分岐の炭素原子数3〜8のアルケニル基を表す。
RA13及びRA17は、互いに同一で異なっていてもよく、水素原子またはヒドロキシ基を表す。
ただし、RA1、RA2及びRA3で表される直鎖又は分岐の炭素原子数1〜12のアルキル基、RA2及びRA3で表される直鎖又は分岐の炭素原子数1〜12のアルコキシ基中のメチレン基は、酸素原子、硫黄原子、炭素−炭素二重結合、−CO−、−CO−O−、−OC−O−、−CO−NH−、−NH−CO−、−CR05=N−および−N=CR06−から選択される少なくとも一以上の構造で置換されていてもよく、前記構造中のR05及びR06は、それぞれ独立に、直鎖又は分岐の炭素原子数1〜8のアルキル基を表す。In the above general formula (A),
RA1 is a linear or branched alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a linear or branched alkenyl group having 3 to 8 carbon atoms, and 6 to 6 carbon atoms. Represents an aryl group of 18, an alkylaryl group having 7 to 18 carbon atoms or an arylalkyl group having 7 to 18 carbon atoms.
RA2 and RA3 may be the same or different from each other, and may be a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a linear or branched alkoxy group having 1 to 12 carbon atoms. Represents
RA4 , RA7 , and RA10 may be the same as or different from each other, and may be a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkenyl having 3 to 8 carbon atoms. Represents a group.
RA13 and RA17 may be the same and different from each other and represent a hydrogen atom or a hydroxy group.
However, R A1, R A2 and linear or branched alkyl group having 1 to 12 carbon atoms represented by R A3, a linear or branched carbon atoms having 1 to 12 of the represented by R A2 and R A3 The methylene group in the alkoxy group is an oxygen atom, a sulfur atom, a carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-CO-,-. It may be substituted with at least one structure selected from CR 05 = N − and −N = CR 06 −, and R 05 and R 06 in the structure are independently linear or branched carbons, respectively. Represents an alkyl group having 1 to 8 atoms.
上記一般式(A)のRA1、RA2及びRA3で表される直鎖又は分岐の炭素原子数1〜12のアルキル基としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、sec−ブチル、tert−ブチル、アミル、イソアミル、tert−アミル、ヘキシル、ヘプチル、n−オクチル、イソオクチル、tert−オクチル、2−エチルヘキシル、ノニル、イソノニル、デシル、ウンデシル、ドデシル等の直鎖又は分岐のアルキル基が挙げられる。The linear or branched alkyl group having 1 to 12 carbon atoms represented by R A1, R A2 and R A3 in the general formula (A), for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, Linear or branched such as sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, undecyl, dodecyl, etc. Alkyl groups can be mentioned.
上記一般式(A)のRA2及びRA3で表される直鎖又は分岐の炭素原子数1〜12のアルコキシ基としては、例えば、メチルオキシ、エチルオキシ、イソプロピルオキシ、ブチルオキシ、sec−ブチルオキシ、tert−ブチルオキシ、イソブチルオキシ、アミルオキシ、イソアミルオキシ、tert−アミルオキシ、ヘキシルオキシ、2−ヘキシルオキシ、3−ヘキシルオキシ、シクロヘキシルオキシ、4−メチルシクロヘキシルオキシ、ヘプチルオキシ、2−ヘプチルオキシ、3−ヘプチルオキシ、イソヘプチルオキシ、tert−ヘプチルオキシ、1−オクチルオキシ、イソオクチルオキシ、tert−オクチルオキシ等が挙げられる。The linear or branched alkoxy group having 1 to 12 carbon atoms represented by R A2 and R A3 in the general formula (A), for example, methyloxy, ethyloxy, isopropyloxy, butyloxy, sec- butyloxy, tert -Butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, Examples thereof include isoheptyloxy, tert-heptyloxy, 1-octyloxy, isooctyloxy, tert-octyloxy and the like.
上記一般式(A)のRA1で表される炭素原子数3〜8のシクロアルキル基としては、例えば、シクロプロピル、シクロペンチル、シクロヘキシル、シクロヘプチル等が挙げられる。The cycloalkyl group having 3 to 8 carbon atoms represented by R A1 in general formula (A), for example, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.
上記一般式(A)のRA1で表される、炭素原子数6〜18のアリール基又は炭素原子7〜18のアルキルアリール基としては、例えば、フェニル、ナフチル、2−メチルフェニル、3−メチルフェニル、4−メチルフェニル、4−ビニルフェニル、3−イソプロピルフェニル、4−イソプロピルフェニル、4−ブチルフェニル、4−イソブチルフェニル、4−tert−ブチルフェニル、4−ヘキシルフェニル、4−シクロヘキシルフェニル、4−オクチルフェニル、4−(2−エチルヘキシル)フェニル、2,3−ジメチルフェニル、2,4−ジメチルフェニル、2,5−ジメチルフェニル、2,6−ジメチルフェニル、3,4−ジメチルフェニル、3,5−ジメチルフェニル、2,4−ジ−tert−ブチルフェニル、2,5−ジ−tert−ブチルフェニル、2,6−ジ−tert−ブチルフェニル、2,4−ジ−tert−ペンチルフェニル、2,5−ジ−tert−アミルフェニル、2,5−ジ−tert−オクチルフェニル、ビフェニル、2,4,5−トリメチルフェニル等が挙げられ、炭素数7〜18のアリールアルキル基としては、例えば、ベンジル、フェネチル、2−フェニルプロパン−2−イル、ジフェニルメチル等が挙げられる。The represented by the general formula R A1 of (A), the alkyl aryl aryl group or a carbon atom 7 to 18 6 to 18 carbon atoms, e.g., phenyl, naphthyl, 2-methylphenyl, 3-methyl Phenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4 -Octylphenyl, 4- (2-ethylhexyl) phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3, 5-Dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2 , 5-Di-tert-amylphenyl, 2,5-di-tert-octylphenyl, biphenyl, 2,4,5-trimethylphenyl and the like. Examples of the arylalkyl group having 7 to 18 carbon atoms include, for example. Examples thereof include benzyl, phenethyl, 2-phenylpropan-2-yl, diphenylmethyl and the like.
上記一般式(A)において、RA1、RA4、RA7、及びRA10で表される直鎖又は分岐の炭素原子数3〜8のアルケニル基としては、例えば、直鎖及び分岐のプロペニル、ブテニル、ペンテニル、ヘキセニル、ヘプテニル、オクテニルが不飽和結合の位置によらず挙げられる。The general formula (A), the alkenyl group R A1, R A4, R A7 , and R A10 few straight or branched carbon atoms represented by 3-8, for example, linear and branched propenyl, Butenyl, pentenyl, hexenyl, heptenyl, and octenyl are listed regardless of the position of the unsaturated bond.
上記一般式(A)において、RA4、RA7、RA10で表される直鎖又は分岐の炭素原子数1〜8のアルキル基としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、sec−ブチル、tert−ブチル、イソブチル、アミル、tert−アミル、オクチル、tert−オクチル等が挙げられる。この中でもメチル基が、紫外線吸収能力に優れるため好ましい。The general formula (A), as the R A4, R A7, a linear or branched alkyl group having 1 to 8 carbon atoms represented by R A10, for example, methyl, ethyl, propyl, isopropyl, butyl, sec -Butyl, tert-butyl, isobutyl, amyl, tert-amyl, octyl, tert-octyl and the like can be mentioned. Of these, the methyl group is preferable because it has an excellent ability to absorb ultraviolet rays.
上記一般式(A)で表されるトリアジン系化合物は、以下の化合物No.1Aから化合物No.5Aのいずれかで表される一または二以上のトリアジン系化合物を含むことが好ましい。 The triazine-based compound represented by the general formula (A) has the following compound No. From 1A, compound No. It preferably contains one or more triazine compounds represented by any of 5A.
また、上記一般式(A)で表されるトリアジン系化合物は、以下の化合物No.6A〜化合物No.8Aのいずれかで表される一または二以上のトリアジン系化合物を含むことが好ましい。
また、本実施形態の粒状紫外線吸収剤は、下記一般式(B)で表される化合物を用いることができる。これらを単独で用いても2種以上を組み合わせて用いてもよい。 Further, as the granular ultraviolet absorber of the present embodiment, a compound represented by the following general formula (B) can be used. These may be used alone or in combination of two or more.
上記一般式(B)中、
RB4、RB5、RB7〜RB9、RB10〜RB12、RB23、RB24、RB26〜RB28、RB29〜RB31は、各々独立して、水素原子、ヒドロキシ基、ハロゲン原子、直鎖又は分岐の炭素原子数1〜8のアルキル基、直鎖又は分岐の炭素原子数2〜8のアルケニル基、直鎖又は分岐の炭素原子数1〜20のアルコキシ基、炭素原子数6〜20のアリール基を表し、nは8〜14の整数を表す。ただし、トリアジン環と連結する3つのベンゼン環のうち、2つのベンゼン環のパラ位は、水素原子、直鎖又は分岐の炭素原子数1〜20のアルキル基、若しくは、直鎖又は分岐の炭素原子数1〜20のアルコキシ基を表し、且つ、オルト位の一つは、水素原子またはヒドロキシ基を表す。) In the above general formula (B),
R B4 , R B5 , R B7 to R B9 , R B10 to R B12 , R B23 , R B24 , R B26 to R B28 , and R B29 to R B31 are independent hydrogen atoms, hydroxy groups, and halogen atoms, respectively. , Linear or branched alkyl group with 1 to 8 carbon atoms, linear or branched alkenyl group with 2 to 8 carbon atoms, linear or branched alkoxy group with 1 to 20 carbon atoms, 6 carbon atoms Represents an aryl group of ~ 20, and n represents an integer of 8-14. However, of the three benzene rings connected to the triazine ring, the para-position of the two benzene rings is a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a linear or branched carbon atom. It represents the number 1 to 20 alkoxy groups, and one of the ortho positions represents a hydrogen atom or a hydroxy group. )
上記一般式(B)中、RB4、RB5、RB7〜RB9、RB10〜RB12、RB23、RB24、RB26〜RB28、RB29〜RB31で表されるハロゲン原子としては、例えば、フッ素原子、塩素原子、臭素原子等が挙げられる。In the general formula (B), as the halogen atom represented by R B4, R B5, R B7 ~R B9, R B10 ~R B12, R B23, R B24, R B26 ~R B28, R B29 ~R B31 For example, a fluorine atom, a chlorine atom, a bromine atom and the like can be mentioned.
上記一般式(B)中、RB4、RB5、RB7〜RB9、RB10〜RB12、RB23、RB24、RB26〜RB28、RB29〜RB31で表される直鎖又は分岐の炭素原子数1〜20のアルキル基としては、メチル、エチル、プロピル、2−プロピニル、ブチル、イソブチル、sec−ブチル、tert−ブチル、ペンチル、イソペンチル、ヘキシル、デシル、ドデシル、オクタデシル等が挙げられる。In the general formula (B), R B4, R B5, R B7 ~R B9, R B10 ~R B12, R B23, R B24, R B26 ~R B28, R B29 linear represented by to R B31 or Examples of the branched alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, 2-propynyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, decyl, dodecyl, octadecyl and the like. Be done.
上記一般式(B)中、RB4、RB5、RB7〜RB9、RB10〜RB12、RB23、RB24、RB26〜RB28、RB29〜RB31で表される直鎖又は分岐の炭素原子数2〜8のアルケニル基としては、ビニル、1−プロペニル、イソプロペニル、2−メチル−1−プロペニル、1−ブテニル、2−ブテニル、3−ブテニル、2−エチル−1−ブテニル、1−ペンテニル、2−ペンテニル、3−ペンテニル、4−ペンテニル、4−メチル−3−ペンテニル、1−ヘキセニル、2−ヘキセニル、3−ヘキセニル、4−ヘキセニル、5−ヘキセニル等が挙げられる。In the general formula (B), R B4, R B5, R B7 ~R B9, R B10 ~R B12, R B23, R B24, R B26 ~R B28, R B29 linear represented by to R B31 or Examples of the branched alkenyl group having 2 to 8 carbon atoms include vinyl, 1-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-ethyl-1-butenyl. , 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 4-methyl-3-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and the like.
上記一般式(B)中、RB4、RB5、RB7〜RB9、RB10〜RB12、RB23、RB24、RB26〜RB28、RB29〜RB31で表される直鎖又は分岐の炭素原子数1〜20のアルコキシ基としては、例えば、メチルオキシ、エチルオキシ、イソプロピルオキシ、ブチルオキシ、sec−ブチルオキシ、tert−ブチルオキシ、イソブチルオキシ、アミルオキシ、イソアミルオキシ、tert−アミルオキシ、ヘキシルオキシ、2−ヘキシルオキシ、3−ヘキシルオキシ、シクロヘキシルオキシ、4−メチルシクロヘキシルオキシ、ヘプチルオキシ、2−ヘプチルオキシ、3−ヘプチルオキシ、イソヘプチルオキシ、tert−ヘプチルオキシ、1−オクチルオキシ、イソオクチルオキシ、tert−オクチルオキシ等が挙げられる。In the general formula (B), R B4, R B5, R B7 ~R B9, R B10 ~R B12, R B23, R B24, R B26 ~R B28, R B29 linear represented by to R B31 or Examples of the branched alkoxy group having 1 to 20 carbon atoms include methyloxy, ethyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, and 2 -Hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, isoheptyloxy, tert-heptyloxy, 1-octyloxy, isooctyloxy, tert − Examples include octyloxy.
上記一般式(B)中、RB4、RB5、RB7〜RB9、RB10〜RB12、RB23、RB24、RB26〜RB28、RB29〜RB31で表される炭素原子数6〜20のアリール基としては、フェニル、ナフチル、アントラセニル、フェナントリル、フルオレニル、インデニル、2−メチルフェニル、3−メチルフェニル、4−メチルフェニル、4−ビニルフェニル、3−イソプロピルフェニル、4−イソプロピルフェニル、4−ブチルフェニル、4−イソブチルフェニル、4−tert−ブチルフェニル、4−ヘキシルフェニル、4−シクロヘキシルフェニル、4−オクチルフェニル、4−(2−エチルヘキシル)フェニル、4−ステアリルフェニル、2,3−ジメチルフェニル、2,4−ジメチルフェニル、2,5−ジメチルフェニル、2,6−ジメチルフェニル、3,4−ジメチルフェニル、3,5−ジメチルフェニル、2,4−ジ−tert−ブチルフェニル、2,5−ジ−tert−ブチルフェニル、2,6−ジ−tert−ブチルフェニル、2,4−ジ−tert−ペンチルフェニル、2,5−ジ−tert−アミルフェニル、2,5−ジ−tert−オクチルフェニル、2,4−ジクミルフェニル、4−シクロヘキシルフェニル、(1,1’−ビフェニル)−4−イル、2,4,5−トリメチルフェニル、フェロセニル等が挙げられる。In the general formula (B), R B4, R B5, R B7 ~R B9, R B10 ~R B12, R B23, R B24, R B26 ~R B28, number of carbon atoms represented by R B29 to R B31 Examples of the aryl group of 6 to 20 include phenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, indenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl and 4-isopropylphenyl. , 4-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3 -Dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-Di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert-amylphenyl, 2,5-di- Examples thereof include tert-octylphenyl, 2,4-dicumylphenyl, 4-cyclohexylphenyl, (1,1'-biphenyl) -4-yl, 2,4,5-trimethylphenyl, ferrosenyl and the like.
また、上記一般式(B)で表されるトリアジン系化合物は、以下の化合物No.1Bから化合物No.4Bのいずれかで表される一または二以上のトリアジン系化合物を含むことが好ましい。
上記化合物No.1Bから化合物No.4B中、RA1、RA2、RB1、RB2、RC1、RC2、RD1及びRD2は、互いに同一でも異なってもよく、水素原子、直鎖又は分岐の炭素原子数1〜4のアルキル基または、直鎖または分岐の炭素原子数1〜4のアルコキシ基を表す。The above compound No. From 1B, compound No. In 4B, RA1 , RA2 , RB1 , RB2 , RC1 , RC2 , RD1 and RD2 may be the same or different from each other, and have 1 to 4 hydrogen atoms, linear or branched carbon atoms. Represents an alkyl group of 1 or an alkoxy group having 1 to 4 carbon atoms in a straight chain or branched.
上記のトリアジン系化合物の合成方法は、特に制限を受けることはなく、トリアジン構造を有する化合物の合成に通常用いられる合成方法のいずれでもよい。例えば、塩化シアヌルにフェノール誘導体またはレゾルシノール誘導体を、三塩化アルミニウムを用いて付加反応させる方法が挙げられる。トリアジン環に単結合で連結したベンゼン環が備える置換基は、トリアジン構造を形成した後に導入してもよく、トリアジン構造を形成する前に、フェノール化合物又はレゾルシノール誘導体に導入してもよい。 The above-mentioned method for synthesizing a triazine-based compound is not particularly limited, and may be any of the synthetic methods usually used for synthesizing a compound having a triazine structure. For example, a method of adding a phenol derivative or a resorcinol derivative to cyanuric chloride using aluminum trichloride can be mentioned. The substituent contained in the benzene ring linked to the triazine ring by a single bond may be introduced after forming the triazine structure, or may be introduced into the phenol compound or resorcinol derivative before forming the triazine structure.
上記のトリアジン系化合物の合成方法の一例としては、例えば、2−[2−ヒドロキシ−4−(2−ヒドロキシエチルオキシ)フェニル]−4,6−ジフェニル−1,3,5−トリアジンをアルコール成分として、該当するエステル誘導性化合物(カルボン酸、カルボン酸ハライド、カルボン酸エステル)とのエステル化反応又はエステル交換反応が挙げられ、これらの反応は逐次反応でもよく、一括反応でもよい。
上記アルコール成分としては、一価カルボン酸のエステル誘導性化合物(一価カルボン酸、一価カルボン酸ハライド又は一価カルボン酸エステル)、二価カルボン酸のエステル誘導性化合物(二価カルボン酸、二価カルボン酸ハライド又は二価カルボン酸のエステル等が挙げられるAs an example of the method for synthesizing the above triazine compound, for example, 2- [2-hydroxy-4- (2-hydroxyethyloxy) phenyl] -4,6-diphenyl-1,3,5-triazine is added as an alcohol component. Examples thereof include an esterification reaction or an ester exchange reaction with the corresponding ester-inducible compound (carboxylic acid, carboxylic acid halide, carboxylic acid ester), and these reactions may be sequential reactions or batch reactions.
Examples of the alcohol component include a monovalent carboxylic acid ester-inducible compound (monovalent carboxylic acid, monovalent carboxylic acid halide or monovalent carboxylic acid ester), and a divalent carboxylic acid ester-inducible compound (divalent carboxylic acid, divalent). Examples thereof include valent carboxylic acid halides and esters of divalent carboxylic acids.
上記トリアジン系化合物は合成後に精製され得る。精製方法としては、蒸留、再結晶、再沈、ろ過剤・吸着剤を用いる方法等を適宜使用することができる。これらを単独で用いても2種以上を組み合わせて用いてもよい。 The triazine compound can be purified after synthesis. As a purification method, distillation, recrystallization, reprecipitation, a method using a filter agent / adsorbent, or the like can be appropriately used. These may be used alone or in combination of two or more.
上記トリアジン系化合物は、必要に応じて、精製後に粉砕、造粒、分級、溶融固化などの加工処理を実施することができる。これらを単独で用いても2種以上を組み合わせて用いてもよい。これにより、所望の粒状トリアジン系化合物の粉体特性を得ることができる。 If necessary, the triazine-based compound can be subjected to processing such as pulverization, granulation, classification, and melt solidification after purification. These may be used alone or in combination of two or more. Thereby, the powder properties of the desired granular triazine compound can be obtained.
本実施形態の粒状紫外線吸収剤の粒状は、顆粒状を意味するものとする。この粒状紫外線吸収剤は、顆粒状のまま使用してもよいが、ペレット、ブリケット、タブレット等の一定形状に加工して使用され得る。 The granules of the granular ultraviolet absorber of the present embodiment are meant to be in the form of granules. This granular ultraviolet absorber may be used as it is in the form of granules, but it can also be used after being processed into a fixed shape such as pellets, briquettes, and tablets.
本実施形態の粒状紫外線吸収剤は、以下の粒度分布で規定される特性を有するものである。 The granular ultraviolet absorber of the present embodiment has the characteristics defined by the following particle size distribution.
本実施形態の粒状紫外線吸収剤について、各篩上の篩残分量は、以下の測定手順に基づいて算出できる。
当該粒状紫外線吸収剤の所定量(g)を、目開き4.0mm篩、目開き2.8mm篩、目開き2.0mm篩、及び目開き1.0mm篩を用いて、この順で篩分を行い、各篩上に残存した当該粒状紫外線吸収剤の残存重量(g)を測定し、所定量に対する残存重量の重量割合(wt%)を篩残分量として算出する。For the granular ultraviolet absorber of the present embodiment, the sieve residue amount on each sieve can be calculated based on the following measurement procedure.
A predetermined amount (g) of the granular ultraviolet absorber is sieved in this order using a 4.0 mm mesh sieve, a 2.8 mm mesh sieve, a 2.0 mm mesh sieve, and a 1.0 mm mesh sieve. Is performed, the residual weight (g) of the granular ultraviolet absorber remaining on each sieve is measured, and the weight ratio (wt%) of the residual weight to a predetermined amount is calculated as the sieve residual amount.
本発明者の知見によれば、適切な目開きを有する篩を複数個使用した篩分条件を採用することにより、粒子径分布がある程度広く、比較的大きな粒子を含む粉体についても、安定的に粒度分布を測定できることが可能であることが判明した。 According to the findings of the present inventor, by adopting a sieving condition using a plurality of sieves having appropriate openings, the particle size distribution is wide to some extent and stable even for powders containing relatively large particles. It was found that it is possible to measure the particle size distribution.
本実施形態において、目開き4.0mm篩の篩残分量は、例えば、0.3wt%以上1.5wt%以下、好ましくは0.4wt%以上1.4wt%以下、より好ましくは0.4wt%以上1.3wt%以下である。
また、目開き2.8mmの篩上の篩残分量は、例えば、5.0wt%以上25.0wt%以下、好ましくは5.5wt%以上24.5wt%以下、より好ましくは6.0wt%以上24.0wt%以下である。
また、目開き2.0mmの篩上の篩残分量は、例えば、25.0wt%以上35.0wt%以下、好ましくは25.5wt%以上34.0wt%以下、より好ましくは26.0wt%以上33.0wt%以下である。
また、目開き1.0mmの篩上の篩残分量は、例えば、35.0wt%以上55.0wt%以下、好ましくは36.0wt%以上54.0wt%以下、より好ましくは37.0wt%以上53.0wt%以下である。
このような各篩の篩残分量を上記数値範囲内とすることにより、1mm以上の範囲で適切な粒度分布を有するため、粉塵性、流動性および溶融混練性を高めることができる。このため、粉体特性に優れた粒状紫外線吸収剤を実現できる。In the present embodiment, the sieve residue amount of the 4.0 mm mesh sieve is, for example, 0.3 wt% or more and 1.5 wt% or less, preferably 0.4 wt% or more and 1.4 wt% or less, more preferably 0.4 wt%. It is 1.3 wt% or less.
The amount of residual sieve residue on a sieve having an opening of 2.8 mm is, for example, 5.0 wt% or more and 25.0 wt% or less, preferably 5.5 wt% or more and 24.5 wt% or less, and more preferably 6.0 wt% or more. It is 24.0 wt% or less.
The amount of the sieve residue on the sieve having a mesh size of 2.0 mm is, for example, 25.0 wt% or more and 35.0 wt% or less, preferably 25.5 wt% or more and 34.0 wt% or less, more preferably 26.0 wt% or more. It is 33.0 wt% or less.
The amount of the sieve residue on the sieve having a mesh opening of 1.0 mm is, for example, 35.0 wt% or more and 55.0 wt% or less, preferably 36.0 wt% or more and 54.0 wt% or less, more preferably 37.0 wt% or more. It is 53.0 wt% or less.
By setting the amount of the sieve residue of each sieve within the above numerical range, it has an appropriate particle size distribution in the range of 1 mm or more, so that dustiness, fluidity and melt-kneadability can be improved. Therefore, a granular ultraviolet absorber having excellent powder characteristics can be realized.
また、本実施形態の粒状紫外線吸収剤において、目開き5.0mm篩に通した際の不通過分量が0wt%となるように構成できる。このように粗大粒子をカットすることにより、粉体特性および紫外線吸収特性に優れた粒状紫外線吸収剤を実現できる。また、溶融混練性を高めることができる。 Further, in the granular ultraviolet absorber of the present embodiment, the amount of non-passing material when passed through a 5.0 mm mesh sieve can be configured to be 0 wt%. By cutting the coarse particles in this way, it is possible to realize a granular ultraviolet absorber having excellent powder characteristics and ultraviolet absorption characteristics. In addition, the melt-kneadability can be improved.
また、本実施形態の粒状紫外線吸収剤において、目開き1.0mm篩の通過分量は、例えば、1.0wt%以上15.0wt%以下、好ましくは2.0wt%以上14.5wt%以下、より好ましくは3.0wt%以上14.0wt%以下である。上記上限値以下とすることにより、粉塵性および流動性を高めることができる。 Further, in the granular ultraviolet absorber of the present embodiment, the amount of passage through the 1.0 mm mesh sieve is, for example, 1.0 wt% or more and 15.0 wt% or less, preferably 2.0 wt% or more and 14.5 wt% or less. It is preferably 3.0 wt% or more and 14.0 wt% or less. By setting the value to the above upper limit or less, dustiness and fluidity can be enhanced.
本実施形態の粒状紫外線吸収剤において、上記の目開き4.0mm篩、目開き2.8mm篩、目開き2.0mm篩、及び目開き1.0mm篩の篩残分量の合計値は、100wt%以下となるように構成される。また、上記の目開き4.0mm篩、目開き2.8mm篩、目開き2.0mm篩、及び目開き1.0mm篩の篩残分量の合計値および目開き1mm篩の通過分量の合計値は、100wt%となるように構成され得る。 In the granular ultraviolet absorber of the present embodiment, the total value of the sieve residue amount of the above-mentioned 4.0 mm mesh sieve, 2.8 mm mesh sieve, 2.0 mm mesh sieve, and 1.0 mm mesh sieve is 100 wt. It is configured to be less than or equal to%. In addition, the total value of the remaining amount of the sieves of the above-mentioned 4.0 mm mesh sieve, 2.8 mm mesh sieve, 2.0 mm mesh sieve, and 1.0 mm mesh sieve and the total amount of passage of the 1 mm mesh sieve. Can be configured to be 100 wt%.
本実施形態では、たとえばトリアジン系化合物の種類や形状、トリアジン系化合物の調製方法等を適切に選択することにより、上記の各篩の篩残分量を制御することが可能である。これらの中でも、たとえば、溶融固化や粉砕・分級などのトリアジン系化合物の加工処理条件を適切に採用すること等が、上記の各篩の篩残分量を所望の数値範囲とするための要素として挙げられる。 In the present embodiment, it is possible to control the sieve residue amount of each of the above-mentioned sieves by appropriately selecting, for example, the type and shape of the triazine-based compound, the method for preparing the triazine-based compound, and the like. Among these, for example, appropriately adopting processing conditions for triazine compounds such as melt solidification, pulverization, and classification are cited as factors for setting the sieve residue amount of each of the above sieves to a desired numerical range. Be done.
また、本発明者はさらに検討したところ、トリアジン系化合物やそれを用いた粒状紫外線吸収剤の粉体特性について、X線回折分析パターンを指針とすることにより適切に制御できることを見出した。このような知見に基づきさらに鋭意研究したところ、粉末X線回折分析パターンにおける極大ピークが存在する回折角2θを所定の数値範囲内とすることにより、上記のトリアジン系化合物やそれを用いた粒状紫外線吸収剤における粉体特性が改善されることを見出した。 Further, the present inventor has found that the powder characteristics of the triazine compound and the granular ultraviolet absorber using the triazine compound can be appropriately controlled by using the X-ray diffraction analysis pattern as a guideline. As a result of further diligent research based on such findings, by setting the diffraction angle 2θ at which the maximum peak exists in the powder X-ray diffraction analysis pattern within a predetermined numerical range, the above-mentioned triazine-based compound and granular ultraviolet rays using it are set. It has been found that the powder properties of the absorbent are improved.
本実施形態のトリアジン系化合物(粒状紫外線吸収剤)は、以下の粉末X線回折分析パターンで規定される特性を有してもよい。 The triazine-based compound (granular ultraviolet absorber) of the present embodiment may have the characteristics defined by the following powder X-ray diffraction analysis pattern.
本実施形態のトリアジン系化合物は、粉末X線回折分析パターンにおける極大ピークを、回折角2θが5.00°以上6.50°以下の範囲内、好ましくは5.20°以上6.00°以下、より好ましくは5.40°以上5.80°以下としてもよい。これにより、フィード性および圧縮造粒性を高めることができるため、粉体特性に優れたトリアジン系化合物や粒状紫外線吸収剤を実現できる。
ここで、極大ピークとは、粉末X線回折測定における走査範囲内(例えば、回折角2θ=3゜〜60゜または3゜〜90゜)で得られたX線回折パターンにおいて、最大ピーク強度を有するものである。The triazine compound of the present embodiment has a maximum peak in the powder X-ray diffraction analysis pattern within a range of 5.00 ° or more and 6.50 ° or less, preferably 5.20 ° or more and 6.00 ° or less. , More preferably 5.40 ° or more and 5.80 ° or less. As a result, the feedability and the compression granulation property can be improved, so that a triazine-based compound or a granular ultraviolet absorber having excellent powder properties can be realized.
Here, the maximum peak means the maximum peak intensity in the X-ray diffraction pattern obtained within the scanning range (for example, diffraction angle 2θ = 3 ° to 60 ° or 3 ° to 90 °) in the powder X-ray diffraction measurement. Have.
また、上記トリアジン系化合物の粉末X線回折分析パターンにおいて、上記極大ピークにおける半値幅は、例えば、0.05°以上0.20°以下、好ましくは0.10°以上0.19°以下、より好ましくは0.15°以上0.18°以下である。このような数値範囲内となるように極大ピーク(最大ピーク)のピーク幅に適切に設定することで、粉体特性および紫外線吸収特性に優れた粒状紫外線吸収剤を実現できる。 Further, in the powder X-ray diffraction analysis pattern of the triazine compound, the half width at the maximum peak is, for example, 0.05 ° or more and 0.20 ° or less, preferably 0.10 ° or more and 0.19 ° or less. It is preferably 0.15 ° or more and 0.18 ° or less. By appropriately setting the peak width of the maximum peak (maximum peak) so as to be within such a numerical range, a granular ultraviolet absorber having excellent powder characteristics and ultraviolet absorption characteristics can be realized.
また、上記トリアジン系化合物の粉末X線回折分析パターンにおいて、上記極大ピークの相対強度を100としたとき、回折角2θが3.0°以上45.0°以下の範囲内に、例えば、相対強度30以上60以下、好ましくは相対強度25以上60以下、より好ましくは相対強度22以上60以下の回折ピークが存在しないように構成される。すなわち、極大ピーク値のピーク強度が相対的に高くすることにより、粉体特性および紫外線吸収特性に優れた粒状紫外線吸収剤を実現できる。 Further, in the powder X-ray diffraction analysis pattern of the triazine compound, when the relative intensity of the maximum peak is 100, the diffraction angle 2θ is within the range of 3.0 ° or more and 45.0 ° or less, for example, the relative intensity. It is configured so that there are no diffraction peaks having a relative intensity of 30 or more and 60 or less, preferably a relative intensity of 25 or more and 60 or less, and more preferably a relative intensity of 22 or more and 60 or less. That is, by relatively increasing the peak intensity of the maximum peak value, it is possible to realize a granular ultraviolet absorber having excellent powder characteristics and ultraviolet absorption characteristics.
また、上記トリアジン系化合物の粉末X線回折分析パターンにおいて、極大ピークの相対強度を100としたとき、当該相対強度1以上5以下の回折ピークが、例えば、回折角2θが45.0°超60.0°以下、好ましくは45.0°超90.0°以下の範囲内に存在しないように構成される。すなわち、微強度のピークが存在しない領域を適切な数値範囲内とすることにより、粉体特性および紫外線吸収特性に優れた粒状紫外線吸収剤を実現できる。 Further, in the powder X-ray diffraction analysis pattern of the triazine compound, when the relative intensity of the maximum peak is 100, the diffraction peak having a relative intensity of 1 or more and 5 or less is, for example, a diffraction angle 2θ of more than 45.0 ° 60. It is configured so that it does not exist within the range of 0.0 ° or less, preferably more than 45.0 ° and 90.0 ° or less. That is, a granular ultraviolet absorber having excellent powder characteristics and ultraviolet absorption characteristics can be realized by setting a region in which a slight intensity peak does not exist within an appropriate numerical range.
本実施形態では、たとえばトリアジン系化合物の種類や形状、トリアジン系化合物の調製方法等を適切に選択することにより、上記極大ピークの回折角2θ、極大ピークの半値幅等の粉末X線回折分析パターンを制御することが可能である。これらの中でも、たとえば、溶融固化や粉砕・分級などのトリアジン系化合物の加工処理条件を適切に採用すること等が、上記極大ピークの回折角2θ、極大ピークの半値幅等の粉末X線回折分析パターンを所望の数値範囲とするための要素として挙げられる。 In the present embodiment, for example, by appropriately selecting the type and shape of the triazine compound, the method for preparing the triazine compound, etc., the powder X-ray diffraction analysis pattern such as the diffraction angle 2θ of the maximum peak and the half width of the maximum peak It is possible to control. Among these, for example, appropriate adoption of processing conditions for triazine compounds such as melt solidification, pulverization, and classification is a powder X-ray diffraction analysis of the diffraction angle 2θ of the maximum peak, the half width of the maximum peak, and the like. It is mentioned as an element for setting a pattern into a desired numerical range.
本実施形態の樹脂組成物について説明する。 The resin composition of this embodiment will be described.
上記樹脂組成物は、上記粒状紫外線吸収剤を含有するものである。この樹脂組成物は、合成樹脂を含有してもよい。これにより、各種の用途に応じた所望の樹脂特性が得られる。 The resin composition contains the granular ultraviolet absorber. This resin composition may contain a synthetic resin. As a result, desired resin properties according to various uses can be obtained.
上記合成樹脂として、例えば、熱可塑性樹脂、熱硬化性樹脂、エラストマー等を挙げることができる。これらを単独で用いても2種以上を組み合わせて用いてもよい。 Examples of the synthetic resin include thermoplastic resins, thermosetting resins, and elastomers. These may be used alone or in combination of two or more.
上記合成樹脂の具体例として以下のものが挙げられる。
上記熱可塑性樹脂として、例えば、ポリプロピレン、高密度ポリエチレン、低密度ポリエチレン、直鎖低密度ポリエチレン、架橋ポリエチレン、超高分子量ポリエチレン、ポリブテン−1、ポリ−3−メチルペンテン等のα−オレフィン重合体又はエチレン−酢酸ビニル共重合体、エチレン−エチルアクリレート共重合体、エチレン−プロピレン共重合体等のポリオレフィン及びこれらの共重合体、ポリ塩化ビニル、ポリ塩化ビニリデン、塩素化ポリエチレン、塩素化ポリプロピレン、ポリフッ化ビニリデン、塩化ゴム、塩化ビニル−酢酸ビニル共重合体、塩化ビニル−エチレン共重合体、塩化ビニル−塩化ビニリデン共重合体、塩化ビニル−塩化ビニリデン−酢酸ビニル三元共重合体、塩化ビニル−アクリル酸エステル共重合体、塩化ビニル−マレイン酸エステル共重合体、塩化ビニル−シクロヘキシルマレイミド共重合体等の含ハロゲン樹脂;石油樹脂、クマロン樹脂、ポリスチレン、ポリ酢酸ビニル、アクリル樹脂、ポリメチルメタクリレート、ポリビニルアルコール、ポリビニルホルマール、ポリビニルブチラール;ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリシクロヘキサンジメチレンテレフタレート等のポリアルキレンテレフタレート、ポリエチレンナフタレート、ポリブチレンナフタレート等のポリアルキレンナフタレート等の芳香族ポリエステル及びポリテトラメチレンテレフタレート等の直鎖ポリエステル;ポリヒドロキシブチレート、ポリカプロラクトン、ポリブチレンサクシネート、ポリエチレンサクシネート、ポリ乳酸樹脂、ポリリンゴ酸、ポリグリコール酸、ポリジオキサン、ポリ(2−オキセタノン)等の分解性脂肪族ポリエステル;ポリフェニレンオキサイド、ポリカプロラクタム及びポリヘキサメチレンアジパミド等のポリアミド、ポリカーボネート、分岐ポリカーボネート、ポリアセタール、ポリフェニレンサルファイド、ポリウレタン、繊維素系樹脂等が挙げられる。Specific examples of the synthetic resin include the following.
Examples of the thermoplastic resin include α-olefin polymers such as polypropylene, high-density polyethylene, low-density polyethylene, linear low-density polyethylene, crosslinked polyethylene, ultrahigh-molecular-weight polyethylene, polybutene-1, poly-3-methylpentene, and the like. Polyethylenes such as ethylene-vinyl acetate copolymers, ethylene-ethyl acrylate copolymers, and ethylene-propylene copolymers and their copolymers, polyvinyl chloride, polyvinylidene chloride, chlorinated polyethylene, chlorinated polypropylene, and polyfluoride. Vinylidene, rubber chloride, vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene copolymer, vinyl chloride-vinylidene chloride copolymer, vinyl chloride-vinylidene chloride-vinyl acetate ternary copolymer, vinyl chloride-acrylic acid Halogen-containing resins such as ester copolymers, vinyl chloride-maleic acid ester copolymers, vinyl chloride-cyclohexylmaleimide copolymers; petroleum resin, kumaron resin, polystyrene, polyvinyl acetate, acrylic resin, polymethylmethacrylate, polyvinyl alcohol , Polyvinylformal, Polyvinylbutyral; Aromatic polyesters such as polyethylene terephthalates, polybutylene terephthalates, polyalkylene terephthalates such as polycyclohexanedimethylene terephthalates, polyalkylene naphthalates such as polyethylene naphthalates and polybutylene naphthalates, and polytetramethylene terephthalates, etc. Straight chain polyesters; degradable aliphatic polyesters such as polyhydroxybutyrate, polycaprolactone, polybutylene succinate, polyethylene succinate, polylactic acid resin, polyapple acid, polyglycolic acid, polydioxane, poly (2-oxetanone); Examples thereof include polyamides such as polyphenylene oxide, polycaprolactam and polyhexamethylene adipamide, polycarbonates, branched polycarbonates, polyacetals, polyphenylene sulfides, polyurethanes, and fibrous resins.
上記熱硬化性樹脂として、例えば、フェノール樹脂、ユリア樹脂、メラミン樹脂、エポキシ樹脂、不飽和ポリエステル樹脂等が挙げられる。 Examples of the thermosetting resin include phenol resin, urea resin, melamine resin, epoxy resin, unsaturated polyester resin and the like.
また、上記エラストマーとして、例えば、フッ素系樹脂、シリコーン樹脂、シリコーンゴムポリエーテルスルホン、ポリサルフォン、ポリフェニレンエーテル、ポリエーテルケトン、ポリエーテルエーテルケトン、液晶ポリマー等を挙げることができる。更に、イソプレンゴム、ブタジエンゴム、アクリロニトリル−ブタジエン共重合ゴム、スチレン−ブタジエン共重合ゴム、フッ素ゴム、シリコーンゴム等が挙げられる。
より具体的なエラストマーとしては、例えば、オレフィン系熱可塑性エラストマー、スチレン系熱可塑性エラストマー、ポリエステル系熱可塑性エラストマー、ニトリル系熱可塑性エラストマー、ナイロン系熱可塑性エラストマー、塩化ビニル系熱可塑性エラストマー、ポリアミド系熱可塑性エラストマー、ポリウレタン系熱可塑性エラストマー等が挙げられる。Examples of the elastomer include fluororesins, silicone resins, silicone rubber polyether sulfones, polysulfones, polyphenylene ethers, polyetherketones, polyetheretherketones, liquid crystal polymers, and the like. Further, isoprene rubber, butadiene rubber, acrylonitrile-butadiene copolymer rubber, styrene-butadiene copolymer rubber, fluororubber, silicone rubber and the like can be mentioned.
More specific elastomers include, for example, olefin-based thermoplastic elastomers, styrene-based thermoplastic elastomers, polyester-based thermoplastic elastomers, nitrile-based thermoplastic elastomers, nylon-based thermoplastic elastomers, vinyl chloride-based thermoplastic elastomers, and polyamide-based thermals. Examples thereof include plastic elastomers and polyurethane-based thermoplastic elastomers.
また、透明性に優れた合成樹脂としては、例えば、ポリエチレン、ポリプロピレン、ポリスチレン、ポリエチレンとノルボルネン等のシクロオレフィンとの共重合体、ポリアクリル酸、ポリアクリル酸エステル、ポリ酢酸ビニル、ポリアクリロニトリル、ポリ塩化ビニル、ポリフッ化ビニル等ビニル化合物およびビニル化合物の付加重合体、ポリメタクリル酸、ポリメタクリル酸エステル、ポリ塩化ビニリデン、ポリフッ化ビニリデン、ポリシアン化ビニリデン、フッ化ビニリデン/トリフルオロエチレン共重合体、フッ化ビニリデン/テトラフルオロエチレン共重合体、シアン化ビニリデン/酢酸ビニル共重合体等のビニル化合物またはフッ素系化合物の共重合体、ポリトリフルオロエチレン、ポリテトラフルオロエチレン、ポリヘキサフルオロプロピレン等のフッ素を含む化合物、ナイロン6、ナイロン66等のポリアミド、ポリイミド、ポリウレタン、ポリペプチド、ポリブチレンテレフタレート、ポリエチレンテレフタレート等のポリエステル、ポリカーボネート、ポリオキシメチレン、ポリエチレンオキシド、ポリプロピレンオキシド等のポリエーテル、エポキシ樹脂、ポリビニルアルコール、ポリビニルブチラール等が挙げられる。 Examples of synthetic resins having excellent transparency include polyethylene, polypropylene, polystyrene, copolymers of polyethylene and cycloolefins such as norbornene, polyvinylidene acid, polyvinylidene ester, vinyl acetate, polyacrylonitrile, and poly. Vinyl compounds such as vinyl chloride and polyvinyl chloride and addition polymers of vinyl compounds, polymethacrylic acid, polymethacrylic acid ester, polyvinylidene chloride, polyvinylidene fluoride, polyvinylidene chloride, vinylidene fluoride / trifluoroethylene copolymer, foot Vinyl compounds such as vinylidene chloride / tetrafluoroethylene copolymer, vinylidene cyanide / vinyl acetate copolymer, or copolymers of fluorine-based compounds, and fluorine such as polytrifluoroethylene, polytetrafluoroethylene, and polyhexafluoropropylene. Containing compounds, polyamides such as nylon 6 and nylon 66, polyimides, polyurethanes, polypeptides, polyvinylidene terephthalates, polyesters such as polyethylene terephthalates, polyethers such as polycarbonate, polyoxymethylene, polyethylene oxide and polypropylene oxide, epoxy resins and polyvinyl alcohols. , Polyvinylidene chloride and the like.
また、相溶性および透明性の観点から、合成樹脂としては、例えば、ポリカーボネート樹脂、ポリエステル樹脂、アクリル樹脂、ABS樹脂等が挙げられる。 Further, from the viewpoint of compatibility and transparency, examples of the synthetic resin include polycarbonate resin, polyester resin, acrylic resin, ABS resin and the like.
以上の合成樹脂は、単独で用いても2種以上を組み合わせて用いてもよく、また、アロイ化されていてもよい。 The above synthetic resins may be used alone, in combination of two or more, or may be alloyed.
上記樹脂組成物における粒状紫外線吸収剤の配合量は、合成樹脂100質量部に対して、例えば、0.001質量部〜20質量部が好ましく、0.01〜10質量部がより好ましく、0.1〜5質量部がさらにより好ましい。上記下限値以上とすることにより、粒状紫外線吸収剤の十分な効果が得られる。また、上記上限値以下とすることにより、粒状紫外線吸収剤の添加効果の向上を得つつも、所望の樹脂物性を実現できる。
本明細書中、「〜」は、特に明示しない限り、上限値と下限値を含むことを表す。The blending amount of the granular ultraviolet absorber in the above resin composition is, for example, preferably 0.001 part by mass to 20 parts by mass, more preferably 0.01 to 10 parts by mass, and 0. 1 to 5 parts by mass is even more preferable. By setting it to the above lower limit value or more, a sufficient effect of the granular ultraviolet absorber can be obtained. Further, by setting the value to the upper limit or less, the desired resin physical properties can be realized while improving the effect of adding the granular ultraviolet absorber.
In the present specification, "~" means that an upper limit value and a lower limit value are included unless otherwise specified.
本実施形態の樹脂組成物は、必要に応じて、上述した成分以外の他の添加成分を含むことができる。この他の添加成分としては、例えば、酸化防止剤、本実施形態に係るトリアジン系化合物以外の紫外線吸収剤、ヒンダードアミン系光安定剤、近赤外線吸収剤、核剤(透明化剤)、帯電防止剤、滑剤、可塑剤、光吸収性色素、充填剤(フィラー)、顔料、染料、金属石鹸、加工助剤、難燃剤、難燃助剤、ゼオライト化合物、発泡剤、(重)金属不活性化剤、架橋剤、エポキシ系安定化剤、マット剤、防曇剤、プレートアウト防止剤、表面処理剤、蛍光増白剤、防黴剤、抗菌剤、離型剤等が挙げられる。 The resin composition of the present embodiment may contain additive components other than the above-mentioned components, if necessary. Other additive components include, for example, an antioxidant, an ultraviolet absorber other than the triazine compound according to the present embodiment, a hindered amine-based light stabilizer, a near-infrared absorber, a nucleating agent (clearing agent), and an antioxidant. , Lubricants, plasticizers, light-absorbing dyes, fillers, pigments, dyes, metal soaps, processing aids, flame retardants, flame retardant aids, zeolite compounds, foaming agents, (heavy) metal inactivating agents , Cross-linking agent, epoxy-based stabilizer, matting agent, antifogging agent, plate-out inhibitor, surface treatment agent, fluorescent whitening agent, antifungal agent, antibacterial agent, mold release agent and the like.
上記酸化防止剤として、例えば、フェノール系酸化防止剤、リン系酸化防止剤、硫黄系酸化防止剤等が挙げられる。 Examples of the antioxidant include phenol-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, and the like.
上記フェノール系酸化防止剤としては、例えば、2,6−ジ−tert−ブチル−p−クレゾール、2,6−ジフェニル−4−オクタデシロキシフェノール、ジステアリル(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)ホスホネート、1,6−ヘキサメチレンビス〔(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオン酸アミド〕、4,4’−チオビス(6−tert−ブチル−m−クレゾール)、2,2’−メチレンビス(4−メチル−6−tert−ブチルフェノール)、2,2’−メチレンビス(4−エチル−6−tert−ブチルフェノール)、4,4’−ブチリデンビス(6−tert−ブチル−m−クレゾール)、2,2’−エチリデンビス(4,6−ジ−tert−ブチルフェノール)、2,2’−エチリデンビス(4−sec−ブチル−6−tert−ブチルフェノール)、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−tert−ブチルフェニル)ブタン、1,3,5−トリス(2,6−ジメチル−3−ヒドロキシ−4−tert−ブチルベンジル)イソシアヌレート、1,3,5−トリス(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)イソシアヌレート、1,3,5−トリス(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)−2,4,6−トリメチルベンゼン、2−tert−ブチル−4−メチル−6−(2−アクリロイルオキシ−3−tert−ブチル−5−メチルベンジル)フェノール、ステアリル(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート、テトラキス〔3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオン酸メチル〕メタン、チオジエチレングリコールビス〔(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート〕、1,6−ヘキサメチレンビス〔(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート〕、ビス〔3,3−ビス(4−ヒドロキシ−3−tert−ブチルフェニル)ブチリックアシッド〕グリコールエステル、ビス〔2−tert−ブチル−4−メチル−6−(2−ヒドロキシ−3−tert−ブチル−5−メチルベンジル)フェニル〕テレフタレート、1,3,5−トリス〔(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオニルオキシエチル〕イソシアヌレート、3,9−ビス〔1,1−ジメチル−2−{(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオニルオキシ}エチル〕−2,4,8,10−テトラオキサスピロ〔5,5〕ウンデカン、トリエチレングリコールビス〔(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオネート〕等が挙げられる。 Examples of the phenolic antioxidant include 2,6-di-tert-butyl-p-cresol, 2,6-diphenyl-4-octadecyloxyphenol, and 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) isocia Nurate, 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) methyl propionate] methane, thiodiethylene glycolbis [(3,5-di-tert-) Butyl-4-hydroxyphenyl) propionate], 1,6-hexamethylenebis [(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], bis [3,3-bis (4-hydroxy-3) -Tert-Butylphenyl) Butyric 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] Examples thereof include undecane and triethylene glycol bis [(3-tert-butyl-4-hydroxy-5-methylphenyl) propionate].
上記リン系酸化防止剤としては、例えば、トリスノニルフェニルホスファイト、トリス〔2−tert−ブチル−4−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニルチオ)−5−メチルフェニル〕ホスファイト、トリデシルホスファイト、トリイソデシルホスファイト、トリラウリルホスファイト、オクチルジフェニルホスファイト、ジ(デシル)モノフェニルホスファイト、ジ(トリデシル)ペンタエリスリトールジホスファイト、ジ(ノニルフェニル)ペンタエリスリトールジホスファイト、ビス(2,4−ジ−tert−ブチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,6−ジ−tert−ブチル−4−メチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,4,6−トリ−tert−ブチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,4−ジクミルフェニル)ペンタエリスリトールジホスファイト、テトラ(トリデシル)イソプロピリデンジフェノールジホスファイト、テトラ(トリデシル)−4,4’−n−ブチリデンビス(2−tert−ブチル−5−メチルフェノール)ジホスファイト、ヘキサ(トリデシル)−1,1,3−トリス(2−メチル−4−ヒドロキシ−5−tert−ブチルフェニル)ブタントリホスファイト、テトラキス(2,4−ジ−tert−ブチルフェニル)ビフェニレンジホスホナイト、9,10−ジハイドロ−9−オキサ−10−ホスファフェナンスレン−10−オキサイド、2,2’−メチレンビス(4,6−tert−ブチルフェニル)−2−エチルヘキシルホスファイト、2,2’−メチレンビス(4,6−tert−ブチルフェニル)−オクタデシルホスファイト、2,2’−エチリデンビス(4,6−ジ−tert−ブチルフェニル)フルオロホスファイト、トリス(2−〔(2,4,8,10−テトラキス−tert−ブチルジベンゾ〔d,f〕〔1,3,2〕ジオキサホスフェピン−6−イル)オキシ〕エチル)アミン、2−エチル−2−ブチルプロピレングリコールと2,4,6−トリ−tert−ブチルフェノールのホスファイト等が挙げられる。 Examples of the phosphorus-based antioxidant include trisnonylphenyl phosphite and tris [2-tert-butyl-4- (3-tert-butyl-4-hydroxy-5-methylphenylthio) -5-methylphenyl]. Phosphite, tridecylphosphite, triisodecylphosphite, trilaurylphosphite, octyldiphenylphosphite, di (decyl) monophenylphosphite, di (tridecyl) pentaerythritol diphosphite, di (nonylphenyl) pentaerythritol 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, tetra (tridecyl) isopropyridendiphenol diphosphite, tetra (tridecyl)- 4,4'-n-butylidenebis (2-tert-butyl-5-methylphenol) diphosphite, hexa (tridecyl) -1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) Butantriphosphite, tetrakis (2,4-di-tert-butylphenyl) biphenylenediphosphonite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 2,2'-methylenebis (4,6-tert-butylphenyl) -2-ethylhexyl phosphite, 2,2'-methylenebis (4,6-tert-butylphenyl) -octadecylphosphite, 2,2'-ethylidenebis (4,6--) Di-tert-butylphenyl) fluorophosphite, tris (2-[(2,4,8,10-tetrakiss-tert-butyldibenzo [d, f] [1,3,2] dioxaphosfepine-6) Examples thereof include phosphite of −yl) oxy] ethyl) amine, 2-ethyl-2-butylpropylene glycol and 2,4,6-tri-tert-butylphenol.
上記硫黄系酸化防止剤としては、例えば、チオジプロピオン酸ジラウリル、チオジプロピオン酸ジミリスチル、チオジプロピオン酸ジステアリル等のジアルキルチオジプロピオネート類、及び、ペンタエリスリトールテトラ(β−アルキルチオプロピオン酸)エステル類が挙げられる。 Examples of the sulfur-based antioxidant include dialkylthiodipropionates such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate, and pentaerythritol tetra (β-alkylthiopropionic acid). Esters can be mentioned.
上記本実施形態に係るトリアジン系化合物以外の他の紫外線吸収剤としては、例えば、2,4−ジヒドロキシベンゾフェノン、2−ヒドロキシ−4−メトキシベンゾフェノン、2−ヒドロキシ−4−オクトキシベンゾフェノン、5,5’−メチレンビス(2−ヒドロキシ−4−メトキシベンゾフェノン)等の2−ヒドロキシベンゾフェノン類;2−(2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジ−tert−ブチルフェニル)−5−クロロベンゾトリアゾ−ル、2−(2’−ヒドロキシ−3’−tert−ブチル−5’−メチルフェニル)−5−クロロベンゾトリアゾ−ル、2−(2’−ヒドロキシ−5’−tert−オクチルフェニル)ベンゾトリアゾ−ル、2−(2’−ヒドロキシ−3’,5’−ジクミルフェニル)ベンゾトリアゾ−ル、2,2’−メチレンビス(4−tert−オクチル−6−(ベンゾトリアゾリル)フェノール)、2−(2’−ヒドロキシ−3’−tert−ブチル−5’−カルボキシフェニル)ベンゾトリアゾール等の2−(2’−ヒドロキシフェニル)ベンゾトリアゾール類;フェニルサリシレート、レゾルシノールモノベンゾエート、2,4−ジ−tert−ブチルフェニル−3,5−ジ−tert−ブチル−4−ヒドロキシベンゾエート、2,4−ジ−tert−アミルフェニル−3,5−ジ−tert−ブチル−4−ヒドロキシベンゾエート、ヘキサデシル−3,5−ジ−tert−ブチル−4−ヒドロキシベンゾエート等のベンゾエート類;2−エチル−2’−エトキシオキザニリド、2−エトキシ−4’−ドデシルオキザニリド等の置換オキザニリド類;エチル−α−シアノ−β、β−ジフェニルアクリレート、メチル−2−シアノ−3−メチル−3−(p−メトキシフェニル)アクリレート等のシアノアクリレート類が挙げられる。 Examples of the ultraviolet absorber other than the triazine compound according to the present embodiment include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 5,5. 2-Hydroxybenzophenones such as'-methylenebis (2-hydroxy-4-methoxybenzophenone); 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 2- (2'-hydroxy-3', 5 '-Di-tert-butylphenyl) -5-chlorobenzotriazol, 2- (2'-hydroxy-3'-tert-butyl-5'-methylphenyl) -5-chlorobenzotriazol, 2- (2'-Hydroxy-5'-tert-octylphenyl) benzotriazol, 2- (2'-hydroxy-3', 5'-dicumylphenyl) benzotriazol, 2,2'-methylenebis (4) 2-(2'-Hydroxyphenyl) such as -tert-octyl-6- (benzotriazolyl) phenol), 2- (2'-hydroxy-3'-tert-butyl-5'-carboxyphenyl) benzotriazole, etc. Bentotriazoles; phenylsalicylate, resorcinol monobenzoate, 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, 2,4-di-tert-amylphenyl-3, Benzoates such as 5-di-tert-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate; 2-ethyl-2'-ethoxyoxanilide, 2-ethoxy- Substituted oxanilides such as 4'-dodecyloxanilide; cyanoacrylates such as ethyl-α-cyano-β, β-diphenyl acrylate, methyl-2-cyano-3-methyl-3- (p-methoxyphenyl) acrylate Can be mentioned.
上記ヒンダードアミン系光安定剤としては、例えば、2,2,6,6−テトラメチル−4−ピペリジルステアレート、1,2,2,6,6−ペンタメチル−4−ピペリジルステアレート、2,2,6,6−テトラメチル−4−ピペリジルベンゾエート、ビス(2,2,6,6−テトラメチル−4−ピペリジル)セバケート、ビス(1,2,2,6,6−テトラメチル−4−ピペリジル)セバケート、ビス(1−オクトキシ−2,2,6,6−テトラメチル−4−ピペリジル)セバケート、テトラキス(2,2,6,6−テトラメチル−4−ピペリジル)−1,2,3,4−ブタンテトラカルボキシレート、テトラキス(1,2,2,6,6−ペンタメチル−4−ピペリジル)−1,2,3,4−ブタンテトラカルボキシレート、ビス(2,2,6,6−テトラメチル−4−ピペリジル)・ジ(トリデシル)−1,2,3,4−ブタンテトラカルボキシレート、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)・ジ(トリデシル)−1,2,3,4−ブタンテトラカルボキシレート、ビス(1,2,2,4,4−ペンタメチル−4−ピペリジル)−2−ブチル−2−(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)マロネート、1−(2−ヒドロキシエチル)−2,2,6,6−テトラメチル−4−ピペリジノ−ル/コハク酸ジエチル重縮合物、1,6−ビス(2,2,6,6−テトラメチル−4−ピペリジルアミノ)ヘキサン/2,4−ジクロロ−6−モルホリノ−s−トリアジン重縮合物、1,6−ビス(2,2,6,6−テトラメチル−4−ピペリジルアミノ)ヘキサン/2,4−ジクロロ−6−tert−オクチルアミノ−s−トリアジン重縮合物、1,5,8,12−テトラキス〔2,4−ビス(N−ブチル−N−(2,2,6,6−テトラメチル−4−ピペリジル)アミノ)−s−トリアジン−6−イル〕−1,5,8,12−テトラアザドデカン、1,5,8,12−テトラキス〔2,4−ビス(N−ブチル−N−(1,2,2,6,6−ペンタメチル−4−ピペリジル)アミノ)−s−トリアジン−6−イル〕−1,5,8−12−テトラアザドデカン、1,6,11−トリス〔2,4−ビス(N−ブチル−N−(2,2,6,6−テトラメチル−4−ピペリジル)アミノ)−s−トリアジン−6−イル〕アミノウンデカン、1,6,11−トリス〔2,4−ビス(N−ブチル−N−(1,2,2,6,6−ペンタメチル−4−ピペリジル)アミノ)−s−トリアジン−6−イル〕アミノウンデカン等のヒンダードアミン化合物が挙げられる。 Examples of the hindered amine-based 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-piperidylbenzoate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-tetramethyl-4-piperidyl) Sevacate, Bis (1-octoxy-2,2,6,6-tetramethyl-4-piperidyl) Sevacate, Tetrax (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4 -Butan tetracarboxylate, tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) -1,2,3,4-butane tetracarboxylate, bis (2,2,6,6-tetramethyl) -4-piperidyl) di (tridecyl) -1,2,3,4-butanetetracarboxylate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) di (tridecyl) -1, 2,3,4-butanetetracarboxylate, bis (1,2,2,4,4-pentamethyl-4-piperidyl) -2-butyl-2- (3,5-di-tert-butyl-4-hydroxy) Benzyl) malonate, 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl-4-piperidinol / diethyl polycondensate succinate, 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-tert-octylamino-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 (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] Hindered amine compounds such as aminoundecane can be mentioned.
上記近赤外線吸収剤としては、例えば、ポリメチン系色素(シアニン色素)、インドリノシアニン系色素、フタロシアニン系色素、ナフタロシアニン系色素、ナフトール金属錯体系色素、スクアリリウム色素、トリアゾ色素、ジチオール金属錯塩系色素、ピリリウム色素、チアピリリウム色素、インドアニリン色素、アゾアントラキノン色素、ナフトキノン色素、アントロキノン色素、ビス(ジチオレン)色素、トリフェニルメタン系色素、アミニウム(アルミニウム)系色素、ジイモニウム系色素等の色素が挙げられ、さらに、無機系の近赤外線吸収剤を使用してもよく、例えばカーボンブラック、酸化アンチモンまたは酸化インジウムをドープした酸化錫、周期表4A,5Aまたは6A族に属する金属の酸化物、炭化物またはホウ化物が挙げられる。 Examples of the near-infrared absorber include polymethine dyes (cyanine dyes), indrinosyanine dyes, phthalocyanine dyes, naphthalocyanine dyes, naphthol metal complex dyes, squarylium dyes, triazo dyes, and dithiol metal complex salt dyes. , Pyrylium pigments, thiapyrylium pigments, indian aniline pigments, azoanthraquinone pigments, naphthoquinone pigments, anthraquinone pigments, bis (dithiolene) pigments, triphenylmethane pigments, aminium (aluminum) pigments, diimonium pigments, etc. Further, an inorganic near-infrared absorber may be used, for example, carbon black, antimony oxide or indium oxide-doped tin oxide, oxides of metals belonging to Group 4A, 5A or 6A of the periodic table, carbides or hoe. Examples include isomers.
上記核剤としては、例えば、p−tert−ブチル安息香酸アルミニウム、安息香酸ナトリウム等の安息香酸類の金属塩、ビス(2,4−ジ−tert−ブチルフェニル)リン酸エステルナトリウム、メチレンビス(2,4−ジ−tert−ブチルフェニル)リン酸エステルナトリウム、ビス〔メチレンビス(2,4−ジ−tert−ブチルフェニル)リン酸エステル〕ヒドロキシアルミニウム等の芳香族リン酸エステル金属塩および芳香族リン酸エステル金属塩とアルカリ金属化合物の混合物、ジベンジリデンソルビトール、ビス(メチルベンジリデン)ソルビトール、ビス(p−エチルベンジリデン)ソルビトール、ビス(ジメチルベンジリデンソルビトール)等のジベンジリデンソルビトール類、アミノ酸金属塩、ロジン酸金属塩、N,N’,N”−トリス[2−メチルシクロヘキシル]−1,2,3−プロパントリカルボキサミド、N,N’,N”−トリシクロヘキシル−1,3,5−ベンゼントリカルボキサミド、N,N’−ジシクロヘキシルナフタレンジカルボキサミド、1,3,5−トリ(ジメチルイソプロポイルアミノ)ベンゼン等のアミド化合物等が挙げられる。 Examples of the nucleating agent include metal salts of benzoic acids such as p-tert-aluminum benzoate and sodium benzoate, sodium bis (2,4-di-tert-butylphenyl) phosphate, and methylenebis (2,). 4-Di-tert-butylphenyl) sodium phosphate, bis [methylenebis (2,4-di-tert-butylphenyl) phosphate] Aromatic phosphate metal salts such as hydroxyaluminum and aromatic phosphates Mixtures of metal salts and alkali metal compounds, dibenzylene sorbitols such as dibenzylene sorbitol, bis (methylbenzylene) sorbitol, bis (p-ethylbenzylene) sorbitol, bis (dimethylbenzylene sorbitol), amino acid metal salts, loginate metal salts , N, N', N "-tris [2-methylcyclohexyl] -1,2,3-propanetricarboxamide, N, N', N" -tricyclohexyl-1,3,5-benzenetricarboxamide, N, Examples thereof include amide compounds such as N'-dicyclohexylnaphthalenedicarboxamide and 1,3,5-tri (dimethylisopropoylamino) benzene.
上記帯電防止剤としては、例えば、脂肪酸第四級アンモニウムイオン塩、ポリアミン四級塩等のカチオン系帯電防止剤;高級アルコールリン酸エステル塩、高級アルコールEO付加物、ポリエチレングリコール脂肪酸エステル、アニオン型のアルキルスルホン酸塩、高級アルコール硫酸エステル塩、高級アルコールエチレンオキシド付加物硫酸エステル塩、高級アルコールエチレンオキシド付加物リン酸エステル塩等のアニオン系帯電防止剤;多価アルコール脂肪酸エステル、ポリグリコールリン酸エステル、ポリオキシエチレンアルキルアリルエーテル等のノニオン系帯電防止剤;アルキルジメチルアミノ酢酸ベタイン等の両性型アルキルベタイン、イミダゾリン型両性活性剤等の両性帯電防止剤、アイオノマーやポリエチレングリコールを親水部とするブロックポリマーを含有する高分子型帯電防止剤が挙げられる。 Examples of the antistatic agent include cationic antistatic agents such as fatty acid quaternary ammonium ion salt and polyamine quaternary salt; higher alcohol phosphate ester salt, higher alcohol EO adduct, polyethylene glycol fatty acid ester, and anionic type. Anionic antistatic agents such as alkyl sulfonates, higher alcohol sulfates, higher alcohol ethylene oxide adducts sulfates, higher alcohol ethylene oxide adduct phosphates; polyhydric alcohol fatty acid esters, polyglycol phosphates, poly Nonionic antistatic agent such as oxyethylene alkylallyl ether; contains amphoteric alkyl betaine such as alkyldimethylaminoacetic acid betaine, amphoteric antistatic agent such as imidazoline amphoteric agent, and block polymer having ionomer or polyethylene glycol as a hydrophilic part. Examples include high molecular weight antistatic agents.
上記滑剤としては、例えば、流動パラフィン、パラフィンワックス、ポリエチレンワックス等の炭化水素系滑剤;ステアリルアルコール、ステアリン酸、12−ヒドロキシステアリン酸等の脂肪族系滑剤;ステアリン酸アミド、オレイン酸アミド、エルカ酸アミド、メチレンビスステアリン酸アミド、エチレンステアリン酸アミド等のアミド系滑剤;ステアリン酸カルシウム、ステアリン酸亜鉛、ステアリン酸マグネシウム、ステアリン酸鉛、ステアリン酸アルミニウム、ステアリン酸バリウム、ステアリン酸バリウム/ステアリン酸亜鉛複合体、ステアリン酸亜鉛/ステアリン酸カルシウム複合体等の金属石鹸系滑剤;硬化油脂、グリセリンモノステアレート、ステアリン酸ブチル、ペンタエリスリトールステアレート、ステアリン酸ステアリル等のエステル系滑剤が挙げられる。 Examples of the lubricant include hydrocarbon-based lubricants such as liquid paraffin, paraffin wax, and polyethylene wax; aliphatic lubricants such as stearyl alcohol, stearic acid, and 12-hydroxystearic acid; stearic acid amide, oleic acid amide, and erucic acid. Amido-based lubricants such as amide, methylenebisstearate amide, ethylene stearic acid amide; calcium stearate, zinc stearate, magnesium stearate, lead stearate, aluminum stearate, barium stearate, barium stearate / zinc stearate complex , Metal soap-based lubricants such as zinc stearate / calcium stearate complex; and ester-based lubricants such as hardened fats and oils, glycerin monostearate, butyl stearate, pentaerythritol stearate, and stearyl stearate.
上記可塑剤としては、例えば、フタル酸エステル、二塩基酸エステル、塩素化パラフィン、ポリエステル、エポキシ化エステル、リン酸エステル、トリメリット酸エステル等が挙げられる。 Examples of the plasticizer include phthalates, dibasic acids, chlorinated paraffins, polyesters, epoxidized esters, phosphoric acids, trimellitic acids and the like.
上記光吸収性色素としては、例えば、シアニン系、キノリン系、クマリン系、チアゾール系、オキソノール系、アズレン系、スクアリリウム系、アゾメチン系、アゾ系、ベンジリデン系、キサンテン系、フタロシアニン系、ジチオール金属錯体系化合物等が挙げられる。 Examples of the light-absorbing dye include cyanine-based, quinoline-based, coumarin-based, thiazole-based, oxonor-based, azulene-based, squarylium-based, azomethine-based, azo-based, benzylidene-based, xanthene-based, phthalocyanine-based, and dithiol metal complex-based. Examples include compounds.
上記充填剤としては、例えば、炭酸カルシウム、酸化カルシウム、水酸化カルシウム、水酸化亜鉛、炭酸亜鉛、硫化亜鉛、酸化マグネシウム、水酸化マグネシウム、炭酸マグネシウム、酸化アルミニウム、水酸化アルミニウム、アルミナケイ酸ナトリウム、ハイドロカルマイト、ケイ酸アルミニウム、ケイ酸マグネシウム、ケイ酸カルシウム、ゼオライト等のケイ酸金属塩、活性白土、タルク、クレイ、ベンガラ、アスベスト、三酸化アンチモン、シリカ、ガラスビーズ、マイカ、セリサイト、ガラスフレーク、アスベスト、ウオラストナイト、チタン酸カリウム、PMF(鉱物繊維)、石膏繊維、ゾノライト、MOS(Magnesium Hydroxide Sulfate Hydrate,繊維状マグネシウム化合物),ホスフェートファイバー、ガラス繊維、炭素繊維、アラミド繊維、セルロースナノファイバー等が挙げられる。 Examples of the filler include calcium carbonate, calcium oxide, calcium hydroxide, zinc hydroxide, zinc carbonate, zinc sulfide, magnesium oxide, magnesium hydroxide, magnesium carbonate, aluminum oxide, aluminum hydroxide, sodium alumina silicate, and the like. Hydrocarbamite, aluminum silicate, magnesium silicate, calcium silicate, metal silicates such as zeolite, active white clay, talc, clay, red iron oxide, asbestos, antimony trioxide, silica, glass beads, mica, sericite, glass Flake, asbestos, wolastonite, potassium titanate, PMF (mineral fiber), gypsum fiber, zonolite, MOS (Magnesium Hydroxide Sulfate Hydrate, fibrous magnesium compound), phosphate fiber, glass fiber, carbon fiber, aramid fiber, cellulose nano Examples include fiber.
上記顔料としては、例えば、市販の顔料を用いることもでき、例えば、ピグメントレッド1、2、3、9、10、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、228、240、254;ピグメントオレンジ13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65、71;ピグメントイエロー1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180、185;ピグメントグリーン7、10、36;ピグメントブルー15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62、64;ピグメントバイオレット1、19、23、27、29、30、32、37、40、50等が挙げられる。 As the pigment, for example, a commercially available pigment can be used, and for example, Pigment Red 1, 2, 3, 9, 10, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185; Pigment Green 7, 10, 36; Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 22, 24, 56, 60, 61, 62, 64; Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50 and the like can be mentioned.
上記染料としては、例えば、アゾ染料、アントラキノン染料、インジゴイド染料、トリアリールメタン染料、キサンテン染料、アリザリン染料、アクリジン染料、スチルベン染料、チアゾール染料、ナフトール染料、キノリン染料、ニトロ染料、インダミン染料、オキサジン染料、フタロシアニン染料、シアニン染料等の染料等が挙げられる。 Examples of the above dyes include azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acrydin dyes, stillben dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, and oxazine dyes. , Dyes such as phthalocyanine dyes and cyanine dyes.
上記金属石鹸としては、例えば、リチウム、ナトリウム、カリウム、マグネシウム、カルシウム、アルミニウム、ヒドロキシアルミニウム、バリウム、亜鉛等の金属と、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ベヘン酸、オレイン酸等の飽和または不飽和脂肪酸の塩が用いられる。 Examples of the metal soap include metals such as lithium, sodium, potassium, magnesium, calcium, aluminum, hydroxyaluminum, barium and zinc, and lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid and oleic acid. Salts of saturated or unsaturated fatty acids are used.
上記加工助剤としては、公知の加工助剤の中から適宜選択することができるが、アクリル酸系加工助剤が好ましい。加工助剤の例を挙げると、例えばメチルメタクリレート、エチルメタクリレート、ブチルメタクリレート等のアルキルメタクリレートの単独重合体又は共重合体;前記アルキルメタクリレートと、メチルアクリレート、エチルアクリレート、ブチルアクリレート等のアルキルアクリレートとの共重合体;前記アルキルメタクリレートと、スチレン、α−メチルスチレン、ビニルトルエン等の芳香族ビニル化合物との共重合体;前記アルキルメタクリレートと、アクリロニトリル、メタクリロニトリル等のビニルシアン化合物等との共重合体等を挙げることができる。 The processing aid can be appropriately selected from known processing aids, but acrylic acid-based processing aids are preferable. Examples of processing aids include homopolymers or copolymers of alkyl methacrylates such as methyl methacrylate, ethyl methacrylate and butyl methacrylate; the alkyl methacrylate and alkyl acrylates such as methyl acrylate, ethyl acrylate and butyl acrylate. Copolymer; Copolymer of the alkyl methacrylate and an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene; the copolymerization of the alkyl methacrylate and a vinyl cyan compound such as acrylonitrile and methacrylonitrile. Coalescence etc. can be mentioned.
上記難燃剤や上記難燃助剤の例としては、下記のトリアジン環含有化合物、金属水酸化物、その他無機リン、ハロゲン系難燃剤、シリコーン系難燃剤、リン酸エステル系難燃剤、縮合リン酸エステル系難燃剤、イントメッセント系難燃剤、三酸化アンチモン等の酸化アンチモン、その他の無機系難燃助剤、有機系難燃助剤等が挙げられる。 Examples of the flame retardant and the flame retardant aid include the following triazine ring-containing compound, metal hydroxide, other inorganic phosphorus, halogen-based flame retardant, silicone-based flame retardant, phosphoric acid ester-based flame retardant, condensed phosphoric acid. Examples thereof include ester-based flame retardants, intomescent-based flame retardants, antimony oxides such as antimony trioxide, other inorganic flame retardants, and organic flame retardants.
上記トリアジン環含有化合物としては、例えば、メラミン、アンメリン、ベンズグアナミン、アセトグアナミン、フタロジグアナミン、メラミンシアヌレート、ピロリン酸メラミン、ブチレンジグアナミン、ノルボルネンジグアナミン、メチレンジグアナミン、エチレンジメラミン、トリメチレンジメラミン、テトラメチレンジメラミン、ヘキサメチレンジメラミン、1,3−ヘキシレンジメランミン等が挙げられる。 Examples of the triazine ring-containing compound include melamine, ammeline, benzguanamine, acetoguanamine, phthalodiguanamine, melamine cyanurate, melamine pyrophosphate, butylene guanamine, norbornene diguanamine, methylene diguanamine, ethylene dimeramine, and trimethylene. Examples thereof include dimelamine, tetramethylene dimelamine, hexamethylene dimelamine, and 1,3-hexylene melamine.
上記金属水酸化物としては、水酸化マグネシウム、水酸化アルミニウム、水酸化カルシウム、水酸化バリウム、水酸化亜鉛、キスマー5A(水酸化マグネシウム:協和化学工業(株)製)等が挙げられる。 Examples of the metal hydroxide include magnesium hydroxide, aluminum hydroxide, calcium hydroxide, barium hydroxide, zinc hydroxide, Kismer 5A (magnesium hydroxide: manufactured by Kyowa Chemical Industry Co., Ltd.) and the like.
上記リン酸エステル系難燃剤の例としては、例えば、トリメチルホスフェート、トリエチルホスフェート、トリブチルホスフェート、トリブトキシエチルホスフェート、トリスクロロエチルホスフェート、トリスジクロロプロピルホスフェート、トリフェニルホスフェート、トリクレジルホスフェート、クレジルジフェニルホスフェート、トリキシレニルホスフェート、オクチルジフェニルホスフェート、キシレニルジフェニルホスフェート、トリスイソプロピルフェニルホスフェート、2−エチルヘキシルジフェニルホスフェート、tert−ブチルフェニルジフェニルホスフェート、ビス−(tert−ブチルフェニル)フェニルホスフェート、トリス−(tert−ブチルフェニル)ホスフェート、イソプロピルフェニルジフェニルホスフェート、ビス−(イソプロピルフェニル)ジフェニルホスフェート、トリス−(イソプロピルフェニル)ホスフェート等が挙げられる。 Examples of the above-mentioned phosphoric acid ester flame retardants include trimethyl phosphate, triethyl phosphate, tributyl phosphate, tributoxyethyl phosphate, trischloroethyl phosphate, trisdichloropropyl phosphate, triphenyl phosphate, tricresyl phosphate, and cresyldiphenyl. Phenyl phosphate, trixylenyl phosphate, octyldiphenyl phosphate, xylenyldiphenyl phosphate, trisisopropylphenyl phosphate, 2-ethylhexyldiphenyl phosphate, tert-butylphenyldiphenyl phosphate, bis- (tert-butylphenyl) phenyl phosphate, tris- (tert) -Butylphenyl) phosphate, isopropylphenyldiphenyl phosphate, bis- (isopropylphenyl) diphenyl phosphate, tris- (isopropylphenyl) phosphate and the like can be mentioned.
上記縮合リン酸エステル系難燃剤の例としては、1,3−フェニレンビス(ジフェニルホスフェート)、1,3−フェニレンビス(ジキシレニルホスフェート)、ビスフェノールAビス(ジフェニルホスフェート)等が挙げられ、イントメッセント系難燃剤としては、ポリリン酸アンモニウム、ポリリン酸メラミン、ポリリン酸ピペラジン、ピロリン酸アンモニウム、ピロリン酸メラミン、ピロリン酸ピペラジン等の、(ポリ)リン酸のアンモニウム塩やアミン塩が挙げられる。 Examples of the condensed phosphoric acid ester flame retardant include 1,3-phenylene bis (diphenyl phosphate), 1,3-phenylene bis (dixylenyl phosphate), bisphenol A bis (diphenyl phosphate), and the like. Examples of the mescent flame retardant include ammonium salts and amine salts of (poly) phosphoric acid such as ammonium polyphosphate, melamine polyphosphate, piperazine polyphosphate, ammonium pyrophosphate, melamine pyrophosphate, and piperazine pyrophosphate.
上記その他の無機系難燃助剤としては、例えば、酸化チタン、酸化アルミニウム、酸化マグネシウム、タルク等の無機化合物、及びその表面処理品が挙げられ、例えば、TIPAQUE R−680(酸化チタン:石原産業(株)製)、キョーワマグ150(酸化マグネシウム:協和化学工業(株)製)、等の種々の市販品を用いることができる。 Examples of the other inorganic flame retardant aid include inorganic compounds such as titanium oxide, aluminum oxide, magnesium oxide, and talc, and surface-treated products thereof. For example, TIPAQUE R-680 (titanium oxide: Ishihara Sangyo). Various commercially available products such as Kyowa Mug 150 (magnesium oxide: manufactured by Kyowa Chemical Industry Co., Ltd.) can be used.
また、その他の有機系難燃助剤としては、例えば、ペンタエリスリトール、ジペンタエリスリトール等が挙げられる。 Examples of other organic flame retardant aids include pentaerythritol and dipentaerythritol.
上記ゼオライト化合物は、独特の三次元のゼオライト結晶構造を有するアルカリ又はアルカリ土類金属のアルミノケイ酸塩であり、その代表例としては、A型、X型、Y型及びP型ゼオライト、モノデナイト、アナルサイト、ソーダライト族アルミノケイ酸塩、クリノブチロライト、エリオナイト及びチャバサイト等を挙げることができ、これらのゼオライト化合物の結晶水(いわゆるゼオライト水)を有する含水物又は結晶水を除去した無水物の何れでもよく、またその粒径が0.1〜50μmのものを用いることができ、特に、0.5〜10μmのものが好ましい。 The above-mentioned zeolite compound is an alkali or alkaline earth metal aluminosilicate having a unique three-dimensional zeolite crystal structure, and typical examples thereof are A-type, X-type, Y-type and P-type zeolite, monodenite, and anal. Sights, sodalite aluminosilicates, clinobtyrolites, erionites, chavasites, etc. can be mentioned, and hydrates having crystalline water (so-called zeolite water) of these zeolite compounds or anhydrides from which crystalline water has been removed. Any of these may be used, and those having a particle size of 0.1 to 50 μm can be used, and those having a particle size of 0.5 to 10 μm are particularly preferable.
上記発泡剤としては、例えば、アゾジカルボンアミド、アゾビスイソブチロニトリル、p,p’−オキシビスベンゼンスルホニルヒドラジド、n,n’−ジニトロソペンタメチレンテトラミン、p−トルエンスルホニルセミカルバジド、トリヒドラゾトリアジン等の分解型有機発泡剤及び重炭酸ナトリウム、炭酸アンモニウム、重炭酸アンモニウム、亜硝酸アンモニウム、アジド化合物、ホウ水素化ナトリウム等の分解型無機発泡剤が挙げられる。 Examples of the foaming agent include azodicarboxylic amide, azobisisobutyronitrile, p, p'-oxybisbenzenesulfonyl hydrazide, n, n'-dinitrosopentamethylenetetramine, p-toluenesulfonyl semicarbazide, and trihydrazo. Examples thereof include decomposition-type organic foaming agents such as triazine and decomposition-type inorganic foaming agents such as sodium bicarbonate, ammonium carbonate, ammonium bicarbonate, ammonium nitrite, azide compounds, and sodium borohydride.
上記(重)金属不活性化剤としては、サリチルアミド−1,2,4−トリアゾール−3−イル、ビスサリチル酸ヒドラジド、ドデカンジオイルビス(2−(2−ヒドロキシベンゾイル)ヒドラジド)、ビス(3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオン酸)ヒドラジド等が挙げられる。 Examples of the (heavy) metal inactivating agent include salicylamide-1,2,4-triazole-3-yl, bissalicylic acid hydrazide, dodecandioil bis (2- (2-hydroxybenzoyl) hydrazide), and bis (3). -(3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid) hydrazide and the like.
上記架橋剤としては、ベンゾイルペルオキシド、ジ−tert−ブチルペルオキシド、ジクミルペルオキシド、2,5−ジメチル−2,5−ジ(tert−ブチルペルオキシ)ヘキサン、2,5−ジメチル−2,5−ジ(tert−ブチルペルオキシ)ヘキシン、1,3−ビス(tert−ブチルペルオキシイソプロピル)ベンゼン−tert−ブチル−ヒドロペルオキシド、クメンヒドロペルオキシド、ポリスルホンアジド、アジドホルメート、テトラメチルイソフタリルジ−tert−ブチルビスペルオキシド、テトラメチルイソフタリルジクミルビスペルオキシド、ジエタノールアミン、トリエタノールアミン等のアルカノールアミン、ヘキサメチレンジアミン、4,4’−ジアミノジフェニルメタン等を挙げることができる。 Examples of the cross-linking agent include benzoyl peroxide, di-tert-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di (tert-butylperoxy) hexane, and 2,5-dimethyl-2,5-di. (Tart-butylperoxy) hexin, 1,3-bis (tert-butylperoxyisopropyl) benzene-tert-butyl-hydroperoxide, cumene hydroperoxide, polysulfone azide, azidoformate, tetramethylisophthalyldi-tert-butyl bisperoxide, Examples thereof include alkanolamines such as tetramethylisophthalyl dicumyl bisperoxide, diethanolamine and triethanolamine, hexamethylenediamine, and 4,4'-diaminodiphenylmethane.
上記エポキシ系安定剤としては、脂肪族、芳香族、脂環族、芳香族脂肪族又はヘテロ環式構造を有し、側鎖としてエポキシ基を有する化合物が挙げられる。エポキシ基は好ましくは、グリシジル基としてエーテル又はエステル結合により分子の残基に結合するか、あるいはヘテロ環式アミン、アミド又はイミドのN−グリシジル誘導体であってもよい。具体的には、エポキシ化大豆油、エポキシ化亜麻仁油、エポキシ化モノエステルなどが挙げられる。エポキシ系安定剤の市販品としては、例えば、株式会社ADEKA製品名「アデカサイザーO−130P」、「アデカサイザーO−180A」、「アデカサイザーD−32」、「アデカサイザーEP−13」、「アデカサイザーFEP−13」等が挙げられる。 Examples of the epoxy-based stabilizer include compounds having an aliphatic, aromatic, alicyclic, aromatic aliphatic or heterocyclic structure and having an epoxy group as a side chain. The epoxy group is preferably attached as a glycidyl group to a residue of the molecule by an ether or ester bond, or may be an N-glycidyl derivative of a heterocyclic amine, amide or imide. Specific examples include epoxidized soybean oil, epoxidized linseed oil, and epoxidized monoester. Examples of commercially available epoxy stabilizers include ADEKA Corporation product names "ADEKA CORPORATION O-130P", "ADEKA CORPORATION O-180A", "ADEKA CORPORATION D-32", "ADEKA CORPORATION EP-13", and "ADEKA CORPORATION". ADEKA Sizer FEP-13 ”and the like.
上記マット剤としては、二酸化ケイ素の微粒子が好ましい。二酸化ケイ素の微粒子の例には、アエロジルR972、R972V、R974、R812、200、200V、300、R202、OX50、TT600(以上日本アエロジル(株)製)が挙げられ、フィルムのヘイズを低く保ちながら摩擦係数を下げる効果が大きいことから、好ましくはアエロジル200V、アエロジルR972V、アエロジルR812である。 As the matting agent, fine particles of silicon dioxide are preferable. Examples of fine particles of silicon dioxide include Aerosil R972, R972V, R974, R812, 200, 200V, 300, R202, OX50, and TT600 (all manufactured by Nippon Aerosil Co., Ltd.), which are rubbed while keeping the haze of the film low. Aerosil 200V, Aerosil R972V, and Aerosil R812 are preferable because they have a large effect of lowering the coefficient.
上記防曇剤としては、例えば、グリセリン脂肪酸エステル、アルキルジエタノールアミン、アルキルジエタノールアミン脂肪酸エステルなどが挙げられる。
上記プレートアウト防止剤としては、例えば、二酸化ケイ素、エチレン−飽和カルボン酸ビニルエステル共重合体けん化物のアルキレンオキサイド付加物を有効成分にしたものが挙げられる。Examples of the antifogging agent include glycerin fatty acid ester, alkyldiethanolamine, and alkyldiethanolamine fatty acid ester.
Examples of the plate-out inhibitor include those containing silicon dioxide and an alkylene oxide adduct of an ethylene-saturated vinyl ester copolymer saponified product as an active ingredient.
上記表面処理剤としては、例えば、アミノシラン化合物、エポキシ樹脂の一種以上を含む表面処理剤が好ましく用いられる。 As the surface treatment agent, for example, a surface treatment agent containing one or more of an aminosilane compound and an epoxy resin is preferably used.
上記アミノシラン化合物としては、例えば、γ−アミノプロピルトリエトキシシラン、γ−アミノプロピルトリメトキシシラン及びγ−(2−アミノエチル)アミノプロピルトリメトキシシラン等が挙げられる。 Examples of the aminosilane compound include γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, and γ- (2-aminoethyl) aminopropyltrimethoxysilane.
上記表面処理剤に含まれるエポキシ樹脂としては、例えば、ノボラック型エポキシ樹脂、ビスフェノール型エポキシ樹脂等が挙げられ、ノボラック型エポキシ樹脂が好ましく用いられる。ノボラック型エポキシ樹脂としては、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂等の多官能型エポキシ樹脂が挙げられる。 Examples of the epoxy resin contained in the surface treatment agent include novolac type epoxy resin and bisphenol type epoxy resin, and novolak type epoxy resin is preferably used. Examples of the novolak type epoxy resin include polyfunctional epoxy resins such as phenol novolac type epoxy resin and cresol novolak type epoxy resin.
また表面処理剤には、上記アミノシラン化合物、エポキシ樹脂の他に、性質を阻害しない範囲で、ウレタン樹脂、アクリル樹脂、耐電防止剤、潤滑剤、及び撥水剤等の成分を配合してもよい。さらに、他の表面処理剤として、ノボラック型及びビスフェノール型以外のエポキシ樹脂、カップリング剤等が挙げられる。 In addition to the aminosilane compound and epoxy resin, the surface treatment agent may contain components such as urethane resin, acrylic resin, antistatic agent, lubricant, and water repellent as long as the properties are not impaired. .. Further, as other surface treatment agents, epoxy resins other than novolak type and bisphenol type, coupling agents and the like can be mentioned.
上記蛍光増白剤とは、太陽光や人工光の紫外線を吸収し、これを紫〜青色の可視光線に変えて輻射する蛍光作用によって、成形体の白色度や青味を助長させる化合物である。蛍光増白剤としては、ベンゾオキサゾール系化合物C.I.Fluorescent Brightner184;クマリン系化合物C.I.Fluorescent Brightner52;ジアミノスチルベンジスルフォン酸系化合物C.I.Fluorescent Brightner24、85、71等が挙げられる。 The fluorescent whitening agent is a compound that absorbs ultraviolet rays of sunlight or artificial light, converts them into purple to blue visible light, and radiates the ultraviolet rays to promote the whiteness and bluish tint of the molded product. .. Examples of the fluorescent whitening agent include benzoxazole compounds C.I. I. Fluorescent Fluorescent 184; Coumarin-based compound C.I. I. Fluorescent Fluorescent 52; diaminostilbene disulphonic acid-based compound C.I. I. Fluorescent Fluorescenter 24, 85, 71 and the like can be mentioned.
上記防黴剤としては、例えば、含窒素含硫黄系、有機臭素系、含窒素系、砒素系等の有機系防黴剤、銀化合物等の無機系防黴剤等が挙げられる。 Examples of the antifungal agent include organic antifungal agents such as nitrogen-containing sulfur-containing, organic bromine-based, nitrogen-containing, and arsenic-based agents, and inorganic antifungal agents such as silver compounds.
上記抗菌剤としては、例えば、塩素系、フェノール系、イミダゾール系またはチアゾール系の化合物や第四級アンモニウム化合物等などの有機系抗菌剤、銀、亜鉛等の金属を保持含有させたゼオライト系、アパタイト系、シリカアルミナ系、セラミック系、リン酸ジルコニウム系、シリカゲル系、ヒドロキシアパタイト系または珪酸カルシウム系などの無機系抗菌剤が挙げられる。 Examples of the antibacterial agent include organic antibacterial agents such as chlorine-based, phenol-based, imidazole-based or thiazole-based compounds and quaternary ammonium compounds, zeolite-based agents containing metals such as silver and zinc, and apatite. Examples thereof include inorganic antibacterial agents such as based, silica-alumina-based, ceramic-based, zirconium phosphate-based, silica gel-based, hydroxyapatite-based, and calcium silicate-based.
上記離型剤としては、例えば、モンタン酸ナトリウム、モンタン酸カリウム、モンタン酸カルシウム、モンタン酸マグネシウムなどが挙げられる。 Examples of the release agent include sodium montanate, potassium montanate, calcium montanate, magnesium montanate and the like.
本実施形態の樹脂組成物の製造方法は特に制限はなく、従来公知の任意の手法を採用することが出来る。 The method for producing the resin composition of the present embodiment is not particularly limited, and any conventionally known method can be adopted.
上記樹脂組成物の製造方法の一例としては、本実施形態の粒状紫外線吸収剤、上述の合成樹脂、必要に応じて他の添加成分等の各成分を、タンブラーやヘンシェルミキサ−等の各種混合機を用い予め混合した後、バンバリーミキサー、ロール、ブラベンダー、単軸混練押出機、二軸混練押出機、ニーダー等で溶融混練する方法が挙げられる。
また各成分を予め混合せずに、又は一部の成分のみ予め混合して、フィーダーを用いて押出機に供給し溶融混練して、樹脂組成物を製造してもよい。更には、一部の成分を予め混合し押出機に供給して溶融混練することで得られる樹脂組成物をマスターバッチとし、再度、他の成分と混合し溶融混練することによって樹脂組成物を製造することもできる。
また、上記の混合・混練工程に用いる合成樹脂は、粉状、ペレット状等の所定形状、または繊維状を有するものであってもよい。As an example of the method for producing the above resin composition, each component such as the granular ultraviolet absorber of the present embodiment, the above-mentioned synthetic resin, and other additive components as required is mixed with various mixers such as a tumbler and a Henschel mixer. A method of melt-kneading with a Banbury mixer, a roll, a brabender, a single-screw kneading extruder, a twin-screw kneading extruder, a kneader or the like can be mentioned.
Further, each component may not be mixed in advance, or only a part of the components may be mixed in advance, supplied to an extruder using a feeder, and melt-kneaded to produce a resin composition. Further, a resin composition obtained by mixing some components in advance, supplying them to an extruder, and melt-kneading them into a masterbatch is used as a masterbatch, and the resin composition is manufactured by mixing with other components and melt-kneading again. You can also do it.
Further, the synthetic resin used in the above mixing / kneading step may have a predetermined shape such as powder or pellet, or a fibrous shape.
本実施形態の樹脂組成物は、室温で固形状でもよく、形状として、粉末状、顆粒状、ペレット、ブリケット、タブレット等の一定形状、またはシート状を有していてもよい。 The resin composition of the present embodiment may be solid at room temperature, and may have a fixed shape such as powder, granules, pellets, briquettes, tablets, or a sheet.
本実施形態の樹脂組成物を成形することにより成形体を得ることができる。
成形方法としては、特に限定されるものではなく、射出成形法、押出成形法、ブロー成形法、回転成形、真空成形法、インフレーション成形法、カレンダー成形法、スラッシュ成形法、ディップ成形法、発泡成形法等が挙げられる。A molded product can be obtained by molding the resin composition of the present embodiment.
The molding method is not particularly limited, and is an injection molding method, an extrusion molding method, a blow molding method, a rotary molding, a vacuum molding method, an inflation molding method, a calendar molding method, a slash molding method, a dip molding method, and a foam molding method. Law etc. can be mentioned.
上記成形体は、用途に応じて各種の形態を有することができるが、例えば、樹脂板、シート、フィルム、容器(ボトル、トレイ、袋)、繊維、各種成形品等の種々の形状を有し得る。 The molded product can have various forms depending on the intended use, and has various shapes such as a resin plate, a sheet, a film, a container (bottle, tray, bag), a fiber, and various molded products. obtain.
また、本実施形態の樹脂組成物は、本実施形態の粒状紫外線吸収剤、バインダー樹脂として用いる上述の合成樹脂、必要に応じて他の添加成分等の各成分を、溶媒に溶解させてワニス樹脂(室温で液状であるワニス状樹脂組成物)としてもよい。溶剤として、有機系溶剤や水系溶媒を用いることができる。必要に応じて乳化剤を用いて、粉末状の紫外線吸収剤を分散させたエマルジョンとして樹脂ワニスを使用してもよい。 Further, in the resin composition of the present embodiment, each component such as the granular ultraviolet absorber of the present embodiment, the above-mentioned synthetic resin used as a binder resin, and if necessary, other additive components are dissolved in a solvent to make a varnish resin. (A varnish-like resin composition that is liquid at room temperature) may be used. As the solvent, an organic solvent or an aqueous solvent can be used. If necessary, a resin varnish may be used as an emulsion in which a powdered UV absorber is dispersed using an emulsifier.
上記樹脂ワニスを調製する方法としては、各成分の混合の順序は特に制限されず、全ての成分を同時に混合してもよいし、予め本実施形態の粒状紫外線吸収剤および他の添加成分を混合して得られた混合物に合成樹脂を混合してしてもよいし、予め調製しておいた複数の成分を他の成分と混合してもよいし、或いは予め調製しておいた複数の成分同士をさらに混合してもよい。
上記樹脂ワニスは、例えば、キャストフィルム法を用いて、フィルムやシートに加工することもできる。また上記樹脂ワニスは、所定の基材上にコーティングするための塗料材料として用いることもできる。As a method for preparing the resin varnish, the order of mixing each component is not particularly limited, and all the components may be mixed at the same time, or the granular ultraviolet absorber of the present embodiment and other additive components are mixed in advance. The synthetic resin may be mixed with the mixture obtained in the above process, a plurality of pre-prepared components may be mixed with other components, or a plurality of pre-prepared components may be mixed. They may be further mixed with each other.
The resin varnish can also be processed into a film or sheet by using, for example, a cast film method. The resin varnish can also be used as a coating material for coating on a predetermined base material.
本実施形態の樹脂組成物は、電気・電子・通信、農林水産、鉱業、建設、食品、繊維、衣類、医療、石炭、石油、ゴム、皮革、自動車、精密機器、木材、建材、土木、家具、印刷、楽器等の幅広い産業分野に使用できる。 The resin composition of the present embodiment includes electricity / electronics / communication, agriculture, forestry and fisheries, mining, construction, food, textiles, clothing, medical care, coal, petroleum, rubber, leather, automobiles, precision equipment, wood, building materials, civil engineering, and furniture. Can be used in a wide range of industrial fields such as printing and musical instruments.
より具体的な用途として、例えば、プリンター、パソコン、ワープロ、キーボード、PDA(小型情報端末機)、電話機、複写機、ファクシミリ、ECR(電子式金銭登録機)、電卓、電子手帳、カード、ホルダー、文具等の事務、OA機器、洗濯機、冷蔵庫、掃除機、電子レンジ、照明器具、ゲーム機、アイロン、コタツ等の家電機器、TV、VTR、ビデオカメラ、ラジカセ、テープレコーダー、ミニディスク、CDプレーヤー、スピーカー、液晶ディスプレイ等のAV機器、コネクター、リレー、コンデンサー、スイッチ、プリント基板、コイルボビン、半導体封止材料、LED封止材料、電線、ケーブル、トランス、偏向ヨーク、分電盤、時計等の電気・電子部品及び通信機器、自動車用内外装材、製版用フィルム、粘着フィルム、ボトル、食品用容器、食品包装用フィルム、製薬・医薬用ラップフィルム、製品包装フィルム、農業用フィルム、農業用シート、温室用フィルム等が挙げられる。 More specific applications include, for example, printers, personal computers, word processors, keyboards, PDAs (small information terminals), telephones, copiers, facsimiles, ECRs (electronic money registration machines), calculators, electronic notebooks, cards, holders, etc. Office work such as stationery, OA equipment, washing machines, refrigerators, vacuum cleaners, microwave ovens, lighting equipment, game machines, irons, household appliances such as kotatsu, TVs, VTRs, video cameras, radio cassette recorders, tape recorders, mini discs, CD players , Speakers, AV equipment such as liquid crystal displays, connectors, relays, capacitors, switches, printed boards, coil bobbins, semiconductor encapsulation materials, LED encapsulation materials, electric wires, cables, transformers, deflection yokes, distribution boards, clocks, etc.・ Electronic parts and communication equipment, interior / exterior materials for automobiles, plate-making films, adhesive films, bottles, food containers, food packaging films, pharmaceutical / pharmaceutical wrap films, product packaging films, agricultural films, agricultural sheets, Examples include greenhouse films.
また、具体的な用途して、座席(詰物、表地等)、ベルト、天井張り、コンパーチブルトップ、アームレスト、ドアトリム、リアパッケージトレイ、カーペット、マット、サンバイザー、ホイルカバー、マットレスカバー、エアバック、絶縁材、吊り手、吊り手帯、電線被覆材、電気絶縁材、塗料、コーティング材、上張り材、床材、隅壁、カーペット、壁紙、壁装材、外装材、内装材、屋根材、デッキ材、壁材、柱材、敷板、塀の材料、骨組及び繰形、窓及びドア形材、こけら板、羽目、テラス、バルコニー、防音板、断熱板、窓材等の自動車、車両、船舶、航空機、建物、住宅及び建築用材料や土木材料、衣料、カーテン、シーツ、不織布、合板、合繊板、絨毯、玄関マット、シート、バケツ、ホース、容器、眼鏡、鞄、ケース、ゴーグル、スキー板、ラケット、テント、楽器等の生活用品、スポーツ用品等の各種用途が挙げられる。この他、塗料、化粧品等が挙げられる。
また、医薬品、ビタミン剤、ドリンク剤、目薬等の薬品容器;化粧水、乳液、日焼け止め等の化粧品容器;食品容器、酒、ワイン、ビール、フルーツジュース、ソフトドリンク、お茶、紅茶、コーヒー等の飲料容器;シャンプー、リンス、うがい液、歯磨き剤、消毒液等の日用品容器等の用途も挙げられる。In addition, specific applications include seats (filling, outer material, etc.), belts, ceilings, compatible tops, armrests, door trims, rear package trays, carpets, mats, sun visors, foil covers, mattress covers, airbags, insulation. Materials, hanging hands, hanging hand bands, wire covering materials, electrical insulation materials, paints, coating materials, upholstery materials, flooring materials, corner walls, carpets, wallpaper, wall covering materials, exterior materials, interior materials, roofing materials, decks Automobiles, vehicles, ships such as materials, wall materials, pillar materials, floor boards, wall materials, skeletons and plywood, window and door profiles, moss boards, siding, terraces, balconies, soundproof boards, heat insulating boards, window materials, etc. , Aircraft, buildings, housing and building materials and civil engineering materials, clothing, curtains, sheets, non-woven fabrics, plywood, synthetic fiber boards, rugs, entrance mats, sheets, buckets, hoses, containers, glasses, bags, cases, goggles, ski boards. , Rackets, tents, daily necessities such as musical instruments, various uses such as sporting goods. In addition, paints, cosmetics and the like can be mentioned.
Also, chemical containers for medicines, vitamins, drinks, eye drops, etc .; cosmetic containers for lotions, emulsions, sunscreens, etc .; food containers, liquor, wine, beer, fruit juices, soft drinks, tea, tea, coffee, etc. Beverage containers: Applications such as daily necessities containers for shampoos, conditioners, mouthwashes, toothpastes, disinfectants, etc. can also be mentioned.
また、本実施形態の樹脂組成物は、特に制限されないが、シートやフィルム等に成形して、光学フィルムや光学シート等の光学材料として好適に使用できる。光学材料としては例えば、液晶表示装置(LCD)、プラズマディスプレイパネル(PDP)、エレクトロルミネッセンスディスプレイ(ELD)、陰極管表示装置(CRT)、蛍光表示管、電界放射型ディスプレイ等の画像表示装置に用いる光学フィルム又は光学シートとして有用であり、特に表示素子に紫外線耐性の劣る有機材料を用いる液晶表示装置や有機ELディスプレイの光学補正フィルム、発光体保護フィルム等の光学フィルムとして有用である。液晶表示装置用途としては、偏光板保護フィルム又は保護シート、位相差フィルム、視野角拡大フィルム、防眩フィルム、輝度向上フィルム、光拡散フィルム及び光拡散シート、レンズフィルム及びレンズシート、防曇フィルム、帯電防止フィルム、光学補正フィルム、反射防止フィルム、色調調整フィルムや導光板等が挙げられ、特に液晶表示素子に接している偏光板の外表面側に設置される光学フィルム若しくは光学シート、又は、偏光板保護フィルム若しくは光学シートに好適に使用できる。 Further, the resin composition of the present embodiment is not particularly limited, but can be suitably used as an optical material such as an optical film or an optical sheet by molding into a sheet or a film. As the optical material, for example, it is used for an image display device such as a liquid crystal display device (LCD), a plasma display panel (PDP), an electroluminescence display (ELD), a cathode tube display device (CRT), a fluorescent display tube, and an electric field radiation type display. It is useful as an optical film or an optical sheet, and is particularly useful as an optical film such as a liquid crystal display device using an organic material having inferior ultraviolet resistance for a display element, an optical correction film for an organic EL display, and a light emitter protective film. Applications of liquid crystal display devices include polarizing plate protective films or protective sheets, retardation films, viewing angle enlargement films, antiglare films, brightness improving films, light diffusing films and light diffusing sheets, lens films and lens sheets, and antifogging films. Examples thereof include antistatic film, optical correction film, antireflection film, color tone adjusting film, light guide plate, etc., and in particular, an optical film or optical sheet installed on the outer surface side of a polarizing plate in contact with a liquid crystal display element, or polarization. It can be suitably used for a plate protective film or an optical sheet.
以上、本発明の実施形態について述べたが、これらは本発明の例示であり、上記以外の様々な構成を採用することもできる。
以下、参考形態の例を付記する。
1. トリアジン系化合物を含む粒状紫外線吸収剤であって、
下記の篩残分量の測定手順に基づいて算出される、
目開き4.0mmの篩上の篩残分量が、0.3wt%以上1.5wt%以下であり、
目開き2.8mmの篩上の篩残分量が、5.0wt%以上25.0wt%以下であり、
目開き2.0mmの篩上の篩残分量が、25.0wt%以上35.0wt%以下であり、
目開き1.0mmの篩上の篩残分量が、35.0wt%以上55.0wt%以下である、という粒度分布を満たす、粒状紫外線吸収剤。
(篩残分量の測定手順)
当該粒状紫外線吸収剤の所定量(g)を、目開き4.0mm篩、目開き2.8mm篩、目開き2.0mm篩、及び目開き1.0mm篩を用いて、この順で篩分を行い、各篩上に残存した当該粒状紫外線吸収剤の残存重量(g)を測定し、前記所定量に対する前記残存重量の重量割合(wt%)を篩残分量として算出する。
2. 1.に記載の粒状紫外線吸収剤であって、
前記トリアジン系化合物が、上記一般式(I)で表される化合物を含む、粒状紫外線吸収剤。
[上記一般式(I)中、
R 1 は、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、炭素原子数3〜20のシクロアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアルキルアリール基、炭素原子数7〜20のアリールアルキル基、炭素原子数2〜8のアルケニル基、又は上記一般式(II)で表される置換基を表し、
R 2 及びR 3 は、それぞれ独立に、水素原子、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、または−O−Rを表し、このRは、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、炭素原子数3〜20のシクロアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアルキルアリール基、又は炭素原子数7〜20のアリールアルキル基を表し、
R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 及びR 12 は、それぞれ独立に、水素原子、ハロゲン原子、置換又は無置換の、直鎖又は分岐の炭素原子数1〜8のアルキル基又は直鎖又は分岐の炭素原子数2〜8のアルケニル基を表し、
R 13 及びR 14 は、それぞれ独立に、水素原子またはヒドロキシ基を表す。
ただし、R 1 、R 2 、R 3 及びRで表される置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 及びR 12 で表される置換又は無置換の、直鎖又は分岐の炭素原子数1〜8のアルキル基中のメチレン基は、酸素原子、硫黄原子、炭素−炭素二重結合、−CO−、−CO−O−、−OC−O−、−CO−NH−、−NH−CO−、−CR 01 =N−および−N=CR 02 −から選択される少なくとも一以上の構造で置換されていてもよく、前記構造中のR 01 及びR 02 は、それぞれ独立に、直鎖又は分岐の炭素原子数1〜8のアルキル基を表す。]
[上記一般式(II)中、
R 21 及びR 22 は、それぞれ独立に、水素原子、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、または、−O−Rを表し、このRは、置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、炭素原子数3〜20のシクロアルキル基、炭素原子数6〜20のアリール基、炭素原子数7〜20のアルキルアリール基、又は炭素原子数7〜20のアリールアルキル基を表し、
R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 及びR 31 は、それぞれ独立に、水素原子、ハロゲン原子、置換又は無置換の、直鎖又は分岐の炭素原子数1〜8のアルキル基、又は直鎖又は分岐の炭素原子数2〜8のアルケニル基を表し、
R 32 及びR 33 は、それぞれ独立に、水素原子またはヒドロキシ基を表し、
X 1 は、置換又は無置換の、直鎖又は分岐の炭素原子数8以上30以下のアルキレン基を表し、
Y 1 及びY 2 は、それぞれ独立に、−CO−O−、−O−CO−、−L 1 −、−O−L 1 O−、−O−L 1 −、−L 1 −O−CO−、−L 1 −CO−O−、−CO−CH=CH−、−CH=CH−CO−、−CH=CH−CO−O−、−CH=CH−O−CO−、−CO−O−CH=CH−を表し、
L 1 は、直鎖又は分岐の炭素原子数1〜8のアルキレン基であり、
m及びnは、それぞれ独立に、0〜8の整数を表し、
*は、式(I)中のR 1 と連結する酸素原子との結合手を表す。
ただし、R 21 、R 22 及びRで表される置換又は無置換の、直鎖又は分岐の炭素原子数1〜20のアルキル基、R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 及びR 31 で表される前記置換又は無置換の、直鎖又は分岐の炭素原子数1〜8のアルキル基およびX 1 で表される直鎖又は分岐の炭素原子数8以上30以下のアルキレン基中のメチレン基は、酸素原子、硫黄原子、炭素−炭素二重結合、−CO−、−CO−O−、−OC−O−、−CO−NH−、−NH−CO−、−CR 03 =N−および−N=CR 04 −から選択される少なくとも一以上の構造で置換されていてもよく、R 03 及びR 04 は、それぞれ独立に、直鎖又は分岐の炭素原子数1〜8のアルキル基を表す。]
3. 1.または2.に記載の粒状紫外線吸収剤であって、
前記トリアジン系化合物が、上記一般式(A)で表される化合物を含む、粒状紫外線吸収剤。
(上記一般式(A)中、
R A1 は、直鎖又は分岐の炭素原子数1〜12のアルキル基、炭素原子数3〜8のシクロアルキル基、直鎖又は分岐の炭素原子数3〜8のアルケニル基、炭素原子数6〜18のアリール基、炭素原子数7〜18のアルキルアリール基または炭素原子数7〜18のアリールアルキル基を表し、
R A2 及びR A3 は、互いに同一でも異なっていてもよく、水素原子、直鎖又は分岐の炭素原子数1〜12のアルキル基、若しくは、直鎖又は分岐の炭素原子数1〜12のアルコキシ基を表し、
R A4 、R A7 、R A10 は、互いに同一でも異なっていてもよく、水素原子、直鎖又は分岐の炭素原子数1〜8のアルキル基または直鎖又は分岐の炭素原子数3〜8のアルケニル基を表し、
R A13 及びR A17 は、互いに同一で異なっていてもよく、水素原子またはヒドロキシ基を表す。
ただし、R A1 、R A2 及びR A3 で表される直鎖又は分岐の炭素原子数1〜12のアルキル基、R A2 及びR A3 で表される直鎖又は分岐の炭素原子数1〜12のアルコキシ基中のメチレン基は、酸素原子、硫黄原子、炭素−炭素二重結合、−CO−、−CO−O−、−OC−O−、−CO−NH−、−NH−CO−、−CR 05 =N−および−N=CR 06 −から選択される少なくとも一以上の構造で置換されていてもよく、前記構造中のR 05 及びR 06 は、それぞれ独立に、直鎖又は分岐の炭素原子数1〜8のアルキル基を表す。)
4. 1.または2.に記載の粒状紫外線吸収剤であって、
前記トリアジン系化合物が、上記の化合物No.1Aから化合物No.8Aのいずれかで表される一または二以上の化合物を含む、粒状紫外線吸収剤。
5. 1.または2.に記載の粒状紫外線吸収剤であって、
前記トリアジン系化合物が、上記一般式(B)で表される化合物を含む、粒状紫外線吸収剤。
(上記一般式(B)中、R B4 、R B5 、R B7 〜R B9 、R B10 〜R B12 、R B23 、R B24 、R B26 〜R B28 、R B29 〜R B31 は、各々独立して、水素原子、ヒドロキシ基、ハロゲン原子、炭素原子数1〜20のアルキル基、炭素原子数2〜20のアルケニル基、炭素原子数1〜20のアルコキシ基、炭素原子数6〜20のアリール基を表し、nは8〜14の整数を表す。ただし、トリアジン環と連結する三つのベンゼン環のうち二つのベンゼン環のパラ位は、水素原子、炭素原子数1〜20のアルキル基または炭素原子数1〜20のアルコキシ基を表し、且つ、オルト位の一つは、水素原子またはヒドロキシ基を表す。)
6. 5.に記載の粒状紫外線吸収剤であって、
前記トリアジン系化合物が、上記の化合物No.1Bから化合物No.4Bのいずれかで表される一または二以上の化合物を含む、粒状紫外線吸収剤。
(上記化合物No.1Bから化合物No.4B中、R A1 、R A2 、R B1 、R B2 、R C1 、R C2 、R D1 及びR D2 は、互いに同一でも異なってもよく、水素原子、直鎖または分岐の炭素原子数1〜4のアルキル基、若しくは、直鎖または分岐の炭素原子数1〜4のアルコキシ基を表す。)
7. 1.〜6.のいずれか1つに記載の粒状紫外線吸収剤であって、
当該粒状紫外線吸収剤を目開き5.0mm篩に通した際の不通過分量が0wt%である、粒状紫外線吸収剤。
8. 1.〜7.のいずれか1つに記載の粒状紫外線吸収剤であって、
上記篩残分量の測定手順を実施したとき、当該粒状紫外線吸収剤の目開き1.0mm篩の通過分量が1.0wt%以上15.0wt%以下である、粒状紫外線吸収剤。
9. 2.〜4.のいずれか1つに記載の粒状紫外線吸収剤であって、
前記トリアジン系化合物が、粉末X線回折分析パターンにおいて、回折角2θが5.00°以上6.50°以下の範囲内に極大ピークを有することを特徴とする、粒状紫外線吸収剤。
10. 9.に記載の粒状紫外線吸収剤であって、
前記トリアジン系化合物の極大ピークの半値幅が、0.05°以上0.20°以下である、粒状紫外線吸収剤。
11. 9.または10.に記載の粒状紫外線吸収剤であって、
前記トリアジン系化合物の極大ピークの相対強度を100としたとき、当該相対強度30以上60以下の回折ピークが、回折角2θが3.0°以上45.0°以下の範囲内に存在しないことを特徴とする、粒状紫外線吸収剤。
12. 9.〜11.のいずれか1つに記載の粒状紫外線吸収剤であって、
請求項トリアジン系化合物の極大ピークの相対強度を100としたとき、当該相対強度1以上5以下の回折ピークが、回折角2θが45.0°超60.0°以下の範囲内に存在しないことを特徴とする、粒状紫外線吸収剤。
13. 1.〜12.のいずれか1つに記載の粒状紫外線吸収剤を含有する、樹脂組成物。
14. 13.に記載の樹脂組成物であって、合成樹脂を含有する樹脂組成物。
Although the embodiments of the present invention have been described above, these are examples of the present invention, and various configurations other than the above can be adopted.
Hereinafter, an example of the reference form will be added.
1. 1. A granular UV absorber containing a triazine compound.
Calculated based on the following procedure for measuring the amount of sieve residue,
The residual amount of the sieve on the sieve having a mesh size of 4.0 mm is 0.3 wt% or more and 1.5 wt% or less.
The residual amount of the sieve on the sieve having a mesh size of 2.8 mm is 5.0 wt% or more and 25.0 wt% or less.
The amount of sieve residue on the sieve having a mesh size of 2.0 mm is 25.0 wt% or more and 35.0 wt% or less.
A granular ultraviolet absorber that satisfies a particle size distribution in which the amount of residual sieve residue on a sieve having a mesh size of 1.0 mm is 35.0 wt% or more and 55.0 wt% or less.
(Measurement procedure for sieve residue)
A predetermined amount (g) of the granular ultraviolet absorber is sieved in this order using a 4.0 mm mesh sieve, a 2.8 mm mesh sieve, a 2.0 mm mesh sieve, and a 1.0 mm mesh sieve. Is performed, the residual weight (g) of the granular ultraviolet absorber remaining on each sieve is measured, and the weight ratio (wt%) of the residual weight to the predetermined amount is calculated as the sieve residual amount.
2. 2. 1. 1. The granular UV absorber described in
A granular ultraviolet absorber, wherein the triazine-based compound contains a compound represented by the general formula (I).
[In the above general formula (I),
R 1 is a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 carbon atoms. Represents an alkylaryl group of ~ 20, an arylalkyl group having 7 to 20 carbon atoms, an alkenyl group having 2-8 carbon atoms, or a substituent represented by the above general formula (II).
R 2 and R 3 independently represent a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or −OR, and this R is substituted or absent. Substituent linear or branched alkyl groups with 1 to 20 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, alkylaryl groups with 7 to 20 carbon atoms, Alternatively, it represents an arylalkyl group having 7 to 20 carbon atoms.
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are independently hydrogen atoms, halogen atoms, substituted or unsubstituted, linear or branched carbons. Represents an alkyl group with 1 to 8 atoms or a linear or branched alkenyl group with 2 to 8 carbon atoms.
R 13 and R 14 each independently represent a hydrogen atom or a hydroxy group.
However, substituted or unsubstituted, linear or branched alkyl groups having 1 to 20 carbon atoms represented by R 1 , R 2 , R 3 and R, R 4 , R 5 , R 6 , R 7 , R. The methylene groups in the substituted or unsubstituted, linear or branched alkyl groups having 1 to 8 carbon atoms represented by 8 , R 9 , R 10 , R 11 and R 12 are oxygen atoms, sulfur atoms, and carbon atoms. - carbon double bond, -CO -, - CO-O -, - OC-O -, - CO-NH -, - NH-CO -, - CR 01 = N- and -N = CR 02 - is selected from It may be substituted with at least one structure, and R 01 and R 02 in the structure each independently represent a linear or branched alkyl group having 1 to 8 carbon atoms. ]
[In the above general formula (II),
R 21 and R 22 independently represent a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or −OR, and this R is substituted or substituted. Unsubstituted, linear or branched alkyl group with 1 to 20 carbon atoms, cycloalkyl group with 3 to 20 carbon atoms, aryl group with 6 to 20 carbon atoms, alkylaryl group with 7 to 20 carbon atoms , Or an arylalkyl group having 7 to 20 carbon atoms.
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 are independently hydrogen atoms, halogen atoms, substituted or unsubstituted, linear or branched carbons, respectively. Represents an alkyl group with 1 to 8 atoms, or a linear or branched alkenyl group with 2 to 8 carbon atoms.
R 32 and R 33 independently represent a hydrogen atom or a hydroxy group, respectively.
X 1 represents a substituted or unsubstituted, linear or branched alkylene group having 8 or more and 30 or less carbon atoms.
Y 1 and Y 2 each independently, -CO-O -, - O -CO -, - L 1 -, - O-L 1 O -, - O-L 1 -, - L 1 -O-CO -, -L 1- CO-O-, -CO-CH = CH-, -CH = CH-CO-, -CH = CH-CO-O-, -CH = CH-O-CO-, -CO- Represents O-CH = CH-
L 1 is a linear or branched alkylene group having 1 to 8 carbon atoms.
m and n each independently represent an integer from 0 to 8.
* Represents a bond with an oxygen atom connected to R 1 in the formula (I).
However, substituted or unsubstituted, linear or branched alkyl groups having 1 to 20 carbon atoms represented by R 21 , R 22 and R, R 23 , R 24 , R 25 , R 26 , R 27 , R. 28, R 29, R 30 and the substituted or unsubstituted represented by R 31, a straight-chain or straight-chain or branched carbon atoms represented by branched alkyl group and X 1 of 1 to 8 carbon atoms The methylene group in the alkylene group of 8 or more and 30 or less is an oxygen atom, a sulfur atom, a carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH. It may be substituted with at least one structure selected from −CO−, −CR 03 = N− and −N = CR 04− , where R 03 and R 04 are independently linear or branched, respectively. Represents an alkyl group having 1 to 8 carbon atoms. ]
3. 3. 1. 1. Or 2. The granular UV absorber described in
A granular ultraviolet absorber, wherein the triazine-based compound contains a compound represented by the general formula (A).
(In the above general formula (A),
R A1 is a linear or branched alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, straight-chain or branched alkenyl group having 3 to 8 carbon atoms, 6 carbon atoms Represents an aryl group of 18, an alkylaryl group having 7 to 18 carbon atoms or an arylalkyl group having 7 to 18 carbon atoms.
R A2 and R A3 may be the same or different from each other, a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a linear or branched alkoxy group having 1 to 12 carbon atoms Represents
R A4, R A7, R A10 may be the same or different from each other, a hydrogen atom, a linear or branched alkyl group or a linear or branched alkenyl having 3 to 8 carbon atoms of 1 to 8 carbon atoms Represents the group
R A13 and R A17 may be different mutually the same and represent a hydrogen atom or a hydroxy group.
However, R A1, R A2 and linear or branched alkyl group having 1 to 12 carbon atoms represented by R A3, a linear or branched carbon atoms having 1 to 12 of the represented by R A2 and R A3 The methylene group in the alkoxy group is an oxygen atom, a sulfur atom, a carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-CO-,-. It may be substituted with at least one structure selected from CR 05 = N − and −N = CR 06 −, and R 05 and R 06 in the structure are independently linear or branched carbons, respectively. Represents an alkyl group having 1 to 8 atoms. )
4. 1. 1. Or 2. The granular UV absorber described in
The triazine-based compound is the above-mentioned compound No. From 1A, compound No. A granular UV absorber comprising one or more compounds represented by any of 8A.
5. 1. 1. Or 2. The granular UV absorber described in
A granular ultraviolet absorber, wherein the triazine-based compound contains a compound represented by the general formula (B).
(In the above general formula (B), R B4 , R B5 , R B7 to R B9 , R B10 to R B12 , R B23 , R B24 , R B26 to R B28 , and R B29 to R B31 are independent of each other. , Hydrogen atom, hydroxy group, halogen atom, alkyl group with 1 to 20 carbon atoms, alkenyl group with 2 to 20 carbon atoms, alkoxy group with 1 to 20 carbon atoms, aryl group with 6 to 20 carbon atoms. Representing, n represents an integer of 8 to 14. However, the para position of two benzene rings among the three benzene rings connected to the triazine ring is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the number of carbon atoms. Represents 1 to 20 alkoxy groups, and one of the ortho positions represents a hydrogen atom or a hydroxy group.)
6. 5. The granular UV absorber described in
The triazine-based compound is the above-mentioned compound No. From 1B, compound No. A granular UV absorber comprising one or more compounds represented by any of 4B.
(The compound No.4B from the compound No.1B, R A1, R A2, R B1, R B2, R C1, R C2, R D1 and R D2, which may be the same or different, a hydrogen atom, a straight It represents an alkyl group having 1 to 4 carbon atoms in a chain or a branch, or an alkoxy group having 1 to 4 carbon atoms in a straight chain or a branch.)
7. 1. 1. ~ 6. The granular ultraviolet absorber according to any one of the above.
A granular ultraviolet absorber having a non-passing amount of 0 wt% when the granular ultraviolet absorber is passed through a 5.0 mm sieve.
8. 1. 1. ~ 7. The granular ultraviolet absorber according to any one of the above.
When the above-mentioned procedure for measuring the residual amount of the sieve is carried out, the granular ultraviolet absorber having a mesh opening of the granular ultraviolet absorber having a diameter of 1.0 mm and a passing amount of 1.0 wt% or more and 15.0 wt% or less.
9. 2. 2. ~ 4. The granular ultraviolet absorber according to any one of the above.
A granular ultraviolet absorber, wherein the triazine compound has a maximum peak in a diffraction angle 2θ of 5.00 ° or more and 6.50 ° or less in a powder X-ray diffraction analysis pattern.
10. 9. The granular UV absorber described in
A granular ultraviolet absorber having a half-value width of a maximum peak of the triazine compound of 0.05 ° or more and 0.20 ° or less.
11. 9. Or 10. The granular UV absorber described in
When the relative intensity of the maximum peak of the triazine compound is 100, the diffraction peak having a relative intensity of 30 or more and 60 or less does not exist in the range where the diffraction angle 2θ is 3.0 ° or more and 45.0 ° or less. A characteristic granular UV absorber.
12. 9. ~ 11. The granular ultraviolet absorber according to any one of the above.
Claim When the relative intensity of the maximum peak of the triazine compound is 100, the diffraction peak having a relative intensity of 1 or more and 5 or less does not exist within the range where the diffraction angle 2θ is more than 45.0 ° and 60.0 ° or less. A granular UV absorber characterized by.
13. 1. 1. ~ 12. A resin composition containing the granular ultraviolet absorber according to any one of the above.
14. 13. The resin composition according to the above, which contains a synthetic resin.
以下、本発明について実施例を参照して詳細に説明するが、本発明は、これらの実施例の記載に何ら限定されるものではない。 Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited to the description of these Examples.
[粒状紫外線吸収剤の調製]
(実施例1)
以下の手順により2,4,6−トリス[2−ヒドロキシ−3−メチル−4−ヘキシルオキシフェニル]トリアジンを合成した。
300mlの四つ口フラスコに2,4,6−トリス(2,4−ジヒドロキシ−3−メチルフェニル)トリアジンを10.00g、水酸化ナトリウムを22.68g、ジメチルホルムアミドを80.00g、1−ブロモヘキサンを11.07g加え80℃まで昇温し、9時間反応させた。塩酸を用いて中和処理を行った後、水洗、減圧脱溶媒し、残渣をトルエン:イソプロピルアルコール=1:1から再結晶することにより、結晶を得た。その後、金属製プレートに溶融させた目的物(結晶)を滴下し、冷却することでフレークを得た(溶融固化処理)。得られたフレークを、粗粉砕・分級することで、融点145℃の淡黄色顆粒11.89g(収率76%)を得た。
得られた化合物(淡黄色顆粒)について、1H−NMR測定を行った。下記分析結果により得られた淡黄色顆粒は、下記式No.1で表される顆粒状の化合物(粒状紫外線吸収剤)と同定された。[Preparation of granular UV absorber]
(Example 1)
2,4,6-tris [2-hydroxy-3-methyl-4-hexyloxyphenyl] triazine was synthesized by the following procedure.
10.00 g of 2,4,6-tris (2,4-dihydroxy-3-methylphenyl) triazine, 22.68 g of sodium hydroxide, 80.00 g of dimethylformamide, 1-bromo in a 300 ml four-necked flask. 11.07 g of hexane was added, the temperature was raised to 80 ° C., and the reaction was carried out for 9 hours. After neutralization treatment with hydrochloric acid, washing with water and desolvation under reduced pressure were performed, and the residue was recrystallized from toluene: isopropyl alcohol = 1: 1 to obtain crystals. Then, the molten object (crystal) was dropped onto a metal plate and cooled to obtain flakes (melting and solidifying treatment). The obtained flakes were roughly pulverized and classified to obtain 11.89 g (yield 76%) of pale yellow granules having a melting point of 145 ° C.
The obtained compound (pale yellow granules) was subjected to 1 1 H-NMR measurement. The pale yellow granules obtained from the following analysis results were obtained by the following formula No. It was identified as a granular compound (granular ultraviolet absorber) represented by 1.
(実施例2〜5)
実施例1と同様にして、異なるロットである、顆粒状の化合物No.1(粒状紫外線吸収剤)を得た。(Examples 2 to 5)
In the same manner as in Example 1, different lots of granular compound No. 1 (granular ultraviolet absorber) was obtained.
(比較例1)
実施例1で得られた結晶を、溶融固化処理を実施せずに、乳鉢粉砕することで、上記式No.1で表される粉状の化合物(粒状紫外線吸収剤)を得た。(Comparative Example 1)
The crystals obtained in Example 1 were crushed in a mortar without performing a melt-solidification treatment to obtain the above formula No. A powdery compound (granular ultraviolet absorber) represented by 1 was obtained.
(比較例2)
実施例1において、分級した際に得られた粗大な粒子径の化合物を集めて、粒状紫外線吸収剤を得た。(Comparative Example 2)
In Example 1, compounds having a coarse particle size obtained during classification were collected to obtain a granular ultraviolet absorber.
以上により得られた粒状紫外線吸収剤について、以下の評価項目に基づいて評価を実施した。評価結果を表1に示す。 The granular ultraviolet absorbers obtained as described above were evaluated based on the following evaluation items. The evaluation results are shown in Table 1.
(粒子径分布)
得られた粒状紫外線吸収剤の粒子径分布を、複数の篩を用いて篩別し、各々の篩上に残留したものの重量から残存割合を算出した。具体的には、以下の通り。
まず、得られた粒状紫外線吸収剤の約200g(全量)を最上段の篩に入れ、下記の目開きの篩、振幅の条件で、篩を備える振動ふるい装置(レッチェ社製、AS300)を用いて、3分間振とうした(篩分操作)。各々の篩上に残存する粒状紫外線吸収剤の重量(g)を測定し、該重量について、導入した全量に対する重量割合(wt%)を、篩残分量として算出した。
・目開き:4.0mm、2.8mm、2.0mm、1.0mm(上からこの順番でセット)
・振幅:1.00mm、3min(Particle size distribution)
The particle size distribution of the obtained granular ultraviolet absorber was sieved using a plurality of sieves, and the residual ratio was calculated from the weight of what remained on each sieve. Specifically, it is as follows.
First, about 200 g (total amount) of the obtained granular ultraviolet absorber is put into the uppermost sieve, and a vibrating sieve (manufactured by Lecce, AS300) equipped with a sieve is used under the conditions of the following open mesh sieve and amplitude. And shaken for 3 minutes (sieving operation). The weight (g) of the granular ultraviolet absorber remaining on each sieve was measured, and the weight ratio (wt%) to the total amount introduced was calculated as the sieve residual amount.
・ Opening: 4.0 mm, 2.8 mm, 2.0 mm, 1.0 mm (set in this order from the top)
・ Amplitude: 1.00 mm, 3 min
表1中、篩残分量は、篩分操作よって篩上に残存する粒状紫外線吸収剤の重量割合を示す。通過分は、目開き1.0mmの篩を通過(パス)した粒状紫外線吸収剤の重量割合を示す。
また、得られた粒状紫外線吸収剤を、目開き5.0mm篩を用いて篩分したときの、目開き5.0mm篩上の篩残分量(wt%)の結果を表1に示す。In Table 1, the sieve residue amount indicates the weight ratio of the granular ultraviolet absorber remaining on the sieve by the sieving operation. The amount passed indicates the weight ratio of the granular ultraviolet absorber that has passed (passed) through a sieve having a mesh size of 1.0 mm.
Table 1 shows the results of the residual amount (wt%) of the sieve residue on the 5.0 mm mesh sieve when the obtained granular ultraviolet absorber was sieved using a 5.0 mm mesh sieve.
(粉塵性)
・ハンドリング性
ポリカーボネート樹脂100質量部に対して、得られた粒状紫外線吸収剤を0.2質量部配合したものを、ヘンシェルミキサーで10分間混合し、混合物を得た。以下の評価基準に基づいてハンドリング性を評価した。
○:粉立ちがほとんど見られなかった。
×:大量の粉立ちが見られた。
・作業環境性
得られた粒状紫外線吸収剤を30cm上部から受け皿に落とし、受け皿に載る量を測定した。以下の評価基準に基づいて作業環境性を評価した。
○:受け皿に残る量が比較的多い。
×:受け皿に残る量が比較的に少なく、その多くが受け皿からはみ出た。(Dustiness)
-Handling property A mixture of 0.2 parts by mass of the obtained granular ultraviolet absorber with respect to 100 parts by mass of the polycarbonate resin was mixed with a Henschel mixer for 10 minutes to obtain a mixture. The handleability was evaluated based on the following evaluation criteria.
◯: Almost no powdering was observed.
X: A large amount of powder was observed.
-Working environment The obtained granular UV absorber was dropped on a saucer from 30 cm above, and the amount placed on the saucer was measured. The work environment was evaluated based on the following evaluation criteria.
◯: The amount remaining in the saucer is relatively large.
X: The amount remaining in the saucer was relatively small, and most of it protruded from the saucer.
(流動性)
ポリカーボネート樹脂100質量部に対して、得られた粒状紫外線吸収剤を0.2質量部配合したものを、ヘンシェルミキサーで10分間混合し、得られた混合物を、押出し機のホッパーから押出し機へ供給した。ホッパーにおける流動性を以下の評価基準に基づいて評価した。
◎:混合物の流動性が良好であり、仕込み不良は発生しなかった
○:混合物が比較的に流動しており、実用上問題ない範囲で仕込み不良は発生しなかった。
×:混合物の流動性が低下しており、仕込み不良が発生した。(Liquidity)
0.2 parts by mass of the obtained granular ultraviolet absorber was mixed with 100 parts by mass of the polycarbonate resin, mixed with a Henschel mixer for 10 minutes, and the obtained mixture was supplied from the hopper of the extruder to the extruder. did. Liquidity in the hopper was evaluated based on the following evaluation criteria.
⊚: The fluidity of the mixture was good and no defective preparation occurred. ◯: The mixture was relatively fluid and no defective preparation occurred within a range where there was no practical problem.
X: The fluidity of the mixture was lowered, and poor preparation occurred.
(溶融混練性)
アクリル樹脂100質量部に対して、得られた粒状紫外線吸収剤を1質量部の配合量に
て配合し、二軸押出機(L/D=30)を用いて、250℃で溶融混練して造粒し、ペレ
ットを得た。吐出量を0.3kg/hに設定したときのペレットを観察し、以下の評価基
準に基づいて溶融混練性を評価した。
○:樹脂と粒状紫外線吸収剤とが均一に分散し、溶融混練をすることができた。
△:樹脂と粒状紫外線吸収剤とがやや分離したが、溶融混練をすることができた。
×:樹脂と粒状紫外線吸収剤とが分離し、溶融混練をすることができなかった。(Melting kneading property)
The obtained granular ultraviolet absorber was blended in an amount of 1 part by mass with respect to 100 parts by mass of the acrylic resin, and melt-kneaded at 250 ° C. using a twin-screw extruder (L / D = 30). Granulation was performed to obtain pellets. The pellets were observed when the discharge rate was set to 0.3 kg / h, and the melt-kneadability was evaluated based on the following evaluation criteria.
◯: The resin and the granular ultraviolet absorber were uniformly dispersed, and melt-kneading was possible.
Δ: The resin and the granular ultraviolet absorber were slightly separated, but melt-kneading was possible.
X: The resin and the granular ultraviolet absorber were separated and could not be melt-kneaded.
また、得られた実施例1、比較例1の粒状紫外線吸収剤について、X線回折分析を行った。評価結果を表2〜4に示す。 In addition, the obtained granular ultraviolet absorbers of Example 1 and Comparative Example 1 were subjected to X-ray diffraction analysis. The evaluation results are shown in Tables 2-4.
(X線回折)
得られた粒状紫外線吸収剤に対して、UltimaIV(株式会社リガク)を用い、以下の測定条件で、粉末X線回折測定を実施した。
(測定条件)
X線管球:CuKα線(CuKα1=1.540562Å、CuKα2=1.544398Å、CuKα2除去なし)
管電圧/管電流:40kV/40mA
アタッチメント:多目的薄膜試料台
モノクロメータ:固定
フィルタ:なし
発散スリット:2/3°
発散縦制限スリット:10mm
散乱スリット:1.17mm
受光スリット:0.3mm
スキャンタイプ:連続スキャン
スキャンスピード:4°/min
サンプリング幅:0.02°
走査軸:2θ/ω
走査範囲:=3゜〜90゜(X-ray diffraction)
Powder X-ray diffraction measurement was carried out on the obtained granular ultraviolet absorber using Ultima IV (Rigaku Co., Ltd.) under the following measurement conditions.
(Measurement condition)
X-ray tube: CuKα ray (CuKα1 = 1.540562Å, CuKα2 = 1.5444398Å, without CuKα2 removal)
Tube voltage / tube current: 40kV / 40mA
Attachment: Multipurpose thin film sample stand Monochromator: Fixed filter: None Diffuse slit: 2/3 °
Divergence vertical restriction slit: 10 mm
Scattering slit: 1.17 mm
Light receiving slit: 0.3 mm
Scan type: Continuous scan Scan speed: 4 ° / min
Sampling width: 0.02 °
Scanning axis: 2θ / ω
Scanning range: = 3 ° to 90 °
実施例1の粒状紫外線吸収剤における粉末X線回折分析の結果を図1に示す。図1の各ピークに対応する回折角2θ、d値、相対強度を表3に示す。表3中、degは、°を表し、ピーク強度の閾値を極大ピークの1/100に設定した。 The result of the powder X-ray diffraction analysis in the granular ultraviolet absorber of Example 1 is shown in FIG. Table 3 shows the diffraction angles 2θ, d values, and relative intensities corresponding to each peak in FIG. In Table 3, deg represents ° and the threshold of peak intensity was set to 1/100 of the maximum peak.
比較例1の粒状紫外線吸収剤における粉末X線回折分析の結果を図2に示す。図2の各ピークに対応する回折角2θ、d値、相対強度を表4に示す。表4中、ピーク強度の閾値を1/100に設定した。 The result of the powder X-ray diffraction analysis in the granular ultraviolet absorber of Comparative Example 1 is shown in FIG. Table 4 shows the diffraction angles 2θ, d values, and relative intensities corresponding to each peak in FIG. In Table 4, the peak intensity threshold was set to 1/100.
(フィード性)
得られた粒状紫外線吸収剤1kgをホッパーに投入し、重量式フィーダー(K−トロン社製、縦:25cm×外径:1.4cm、溝の幅:2.0cm、溝の深さ:0.3cmのTwin spiral typeの二軸スクリュー)を用いて、フィーダー排出量:0.3kg/hの条件で、30分間排出した(フィード性試験)。
・定量性
重量式フィーダーから排出された量(フィーダー量)を、10分間隔で経時的に測定した。フィード量のバラツキが小さい場合を○、フィード量のバラツキが大きい場合を×とした。
・ロングラン性
排出時間の条件を30分間から3時間に変更した以外は同様にして、上記のフィード試験を実施した。3時間排出し続けた場合を○、3時間の経過前に運転が停止した場合を×とした。(Feedability)
1 kg of the obtained granular UV absorber was put into a hopper, and a heavy-duty feeder (manufactured by K-Tron, length: 25 cm x outer diameter: 1.4 cm, groove width: 2.0 cm, groove depth: 0. Using a 3 cm Twin spiral type biaxial screw), the feeder was discharged for 30 minutes under the condition of a feeder discharge amount of 0.3 kg / h (feedability test).
-Quantitative The amount discharged from the heavy-duty feeder (feeder amount) was measured over time at 10-minute intervals. The case where the variation in the feed amount was small was evaluated as ◯, and the case where the variation in the feed amount was large was evaluated as x.
-Long-run property The above feed test was carried out in the same manner except that the condition of the discharge time was changed from 30 minutes to 3 hours. The case where the water was continuously discharged for 3 hours was marked with ◯, and the case where the operation was stopped before the lapse of 3 hours was marked with x.
(圧縮造粒性)
ローラーコンパクター(ホソカワミクロン社製、造粒機M−25型)を用いて、ロールギャップ:3.2mm、ロール回転速度:14rpmの条件で、得られた粒状紫外線吸収剤を圧縮造粒して、板厚み:4mmの板状顆粒を得た。得られた板状顆粒を粉砕し、5メッシュの振動篩にて粗粉を除去し、次いで24メッシュの振動篩にて微粉を除去した後(整粒)、24メッシュの振動櫛上に残存した板状の造粒物を得た。
得られた造粒物について外観観察を行い、造粒物の崩壊度合いを下記の基準に基づいて評価した。
10個中10個の造粒物において崩壊が観察できなかったものを○とし、10個中1個以上4個以下の造粒物において一部の崩壊が観察されたものを△とし、10個中5個以上の造粒物の一部または全体の崩壊が観察されたものを×とした。(Compression granulation property)
Using a roller compactor (Hosokawa Micron Co., Ltd., granulator M-25 type), the obtained granular ultraviolet absorber was compression-granulated under the conditions of roll gap: 3.2 mm and roll rotation speed: 14 rpm to form a plate. Plate-shaped granules having a thickness of 4 mm were obtained. The obtained plate-shaped granules were crushed, coarse powder was removed with a 5-mesh vibrating sieve, and then fine powder was removed with a 24-mesh vibrating sieve (grain size), and then remained on the 24-mesh vibrating comb. A plate-shaped granule was obtained.
The appearance of the obtained granulated product was observed, and the degree of disintegration of the granulated product was evaluated based on the following criteria.
In 10 out of 10 granules, no disintegration was observed, and in 10 out of 10, 1 or more and 4 or less granules, in which some disintegration was observed, were marked with Δ. Those in which partial or total collapse of 5 or more granules was observed were marked with x.
[樹脂組成物の調製]
(フィルムの作製)
合成樹脂(ポリカーボネート樹脂:三菱エンジニアリングプラスチックス(株)製、製品名E−2000)100質量部に対して、得られた各実施例の粒状紫外線吸収剤を0.2質量部配合したものを、溶媒(トルエン/シクロヘキサン=9/1)230質量部に溶解することにより、樹脂組成物を調製した。得られた樹脂組成物で、キャスト法により厚さ40μmのフィルムを作製し、1辺2cmの正方形のフィルム試験片を得た。
得られたフィルム試験片を、サンシャインウェザオメーター(83℃、雨なし、光源カーボンアーク)にて、240、360及び480時間後の全光線透過率(%)の保持率(%)を測定し、耐光性を評価した。
240、360及び480時間後の保持率(%)が高い値を示した結果から、各実施例の粒状紫外線吸収剤を使用することにより、優れた耐光性を実現できることが分かった。
また、合成樹脂として、ポリカーボネート樹脂に代えて、メタクリル樹脂、ノルボルネン樹脂、ポリエチレンテレフタレート樹脂、又はポリスチレン樹脂を用いた場合でも、同様に優れた耐光性を実現できることが分かった。[Preparation of resin composition]
(Production of film)
A mixture of 100 parts by mass of a synthetic resin (polycarbonate resin: manufactured by Mitsubishi Engineering Plastics Co., Ltd., product name E-2000) and 0.2 parts by mass of the obtained granular ultraviolet absorbers of each example was prepared. A resin composition was prepared by dissolving in 230 parts by mass of a solvent (toluene / cyclohexane = 9/1). From the obtained resin composition, a film having a thickness of 40 μm was prepared by a casting method, and a square film test piece having a side of 2 cm was obtained.
The obtained film test piece was measured with a sunshine weather meter (83 ° C., no rain, light source carbon arc) to measure the retention rate (%) of the total light transmittance (%) after 240, 360 and 480 hours. , Light resistance was evaluated.
From the results showing high retention rates (%) after 240, 360 and 480 hours, it was found that excellent light resistance can be realized by using the granular ultraviolet absorbers of each example.
Further, it was found that even when a methacrylic resin, a norbornene resin, a polyethylene terephthalate resin, or a polystyrene resin is used as the synthetic resin instead of the polycarbonate resin, similarly excellent light resistance can be realized.
(容器の作製)
ポリエチレンテレフタレート(固有粘度:0.8dL/g)100質量部に対して、得られた各実施例の粒状紫外線吸収剤を0.3質量部加えて混合し、樹脂組成物を得た。得られた樹脂組成物について、160℃のギヤーオーブンで4時間乾燥後、射出成形機にて、射出温度280℃の成形温度で、プリフォーム(口外径25mm、重量23g)を成形した。次に、得られたプリフォームについて、金型温度130℃で二軸延伸ブロー成形し、容量500mL、厚さ0.7mmのプラスチックボトルを作製した。得られたプラスチックボトルについて、波長500nmの可視光線の透過率、波長400nmの紫外線の透過率を測定した。波長500nmの透過率が高く、波長400nmの透過率が低い結果から、得られたプラスチックボトル(容器)は、紫外線を効率的に吸収し、また、可視光線の透過性も十分確保できていることが分かった。(Making a container)
To 100 parts by mass of polyethylene terephthalate (intrinsic viscosity: 0.8 dL / g), 0.3 parts by mass of the obtained granular ultraviolet absorbers of each example were added and mixed to obtain a resin composition. The obtained resin composition was dried in a gear oven at 160 ° C. for 4 hours, and then a preform (outer diameter 25 mm, weight 23 g) was molded by an injection molding machine at a molding temperature of 280 ° C. Next, the obtained preform was biaxially stretched and blow-molded at a mold temperature of 130 ° C. to prepare a plastic bottle having a capacity of 500 mL and a thickness of 0.7 mm. With respect to the obtained plastic bottle, the transmittance of visible light having a wavelength of 500 nm and the transmittance of ultraviolet rays having a wavelength of 400 nm were measured. From the results that the transmittance at a wavelength of 500 nm is high and the transmittance at a wavelength of 400 nm is low, the obtained plastic bottle (container) efficiently absorbs ultraviolet rays and sufficiently secures the transmittance of visible light. I found out.
(コーティング材の作製)
・紫外線吸収層
ノルボルネン樹脂(JSR(株)製、製品名:ARTON F5023)100質量部に対して、得られた各実施例の粒状紫外線吸収剤を0.5質量部、並びに溶媒としてジクロロメタン2000質量部を混合し、樹脂溶液(樹脂組成物)を得た。得られた樹脂溶液を、表面研磨したガラス板上にバーコーターを用いて流延し、50℃で20分の予備乾燥、90℃で30分の乾燥を経て、膜厚80〜90μmのフィルムを作製した後、1辺2cmの正方形のフィルム試験片(紫外線吸収層)を得た。
・NIR吸収層の作製
ノルボルネン樹脂(JSR(株)製、製品名:ARTON F5023)100質量部に対して、近赤外線吸収剤としてジイモニウム系化合物(日本化薬(株)製、製品名:IRG−068)0.3質量部、溶媒としてジクロロメタン2000質量部からなる樹脂溶液を、表面研磨したガラス板上にバーコーターを用いて流延し、50℃で20分の予備乾燥、90℃で30分の乾燥を経て、膜厚50〜60μmのフィルムを作製した後、1辺2cmの正方形のフィルム試験片を得た。
得られたNIR吸収層及び紫外線吸収層を重ね合わせた試験片につき、サンシャインウェザーメーター(スガ試験機株式会社製;83℃、雨なし、光源カーボンアーク)にて、紫外線吸収層側から試験光が当たるようにして、360(又は540)時間曝露した。耐光試験前後のNIR領域の極大波長(NIR吸収層:1100nm)における透過率を測定し、透過率の減衰率(Δ透過率)により耐光性評価を行った。
各実施例において、Δ透過率を低減できた結果から、近赤外線吸収剤の光劣化に対して効果を示すことが確かめられた。これにより、近赤外線吸収層における近赤外線吸収剤の光劣化防止に優れることが分かった。(Preparation of coating material)
-Ultraviolet absorbing layer 0.5 parts by mass of the obtained granular ultraviolet absorber of each example and 2000 parts by mass of dichloromethane as a solvent with respect to 100 parts by mass of norbornene resin (manufactured by JSR Co., Ltd., product name: ARTON F5023). The parts were mixed to obtain a resin solution (resin composition). The obtained resin solution was cast on a surface-polished glass plate using a bar coater, pre-dried at 50 ° C. for 20 minutes, dried at 90 ° C. for 30 minutes, and then a film having a thickness of 80 to 90 μm was formed. After preparation, a square film test piece (ultraviolet absorbing layer) having a side of 2 cm was obtained.
-Preparation of NIR absorption layer A diimonium compound (manufactured by Nippon Kayaku Co., Ltd., product name: IRG-) as a near-infrared absorber with respect to 100 parts by mass of a solvent resin (manufactured by JSR Co., Ltd., product name: ARTON F5023). 068) A resin solution consisting of 0.3 parts by mass and 2000 parts by mass of dichloromethane as a solvent was cast on a surface-polished glass plate using a bar coater, pre-dried at 50 ° C. for 20 minutes, and pre-dried at 90 ° C. for 30 minutes. After drying to prepare a film having a thickness of 50 to 60 μm, a square film test piece having a side of 2 cm was obtained.
The obtained test piece in which the NIR absorption layer and the ultraviolet absorption layer were overlapped was subjected to test light from the ultraviolet absorption layer side with a sunshine weather meter (manufactured by Suga Test Instruments Co., Ltd .; 83 ° C, no rain, light source carbon arc). It was exposed for 360 (or 540) hours so as to hit. The transmittance at the maximum wavelength (NIR absorption layer: 1100 nm) in the NIR region before and after the light resistance test was measured, and the light resistance was evaluated by the attenuation rate (Δ transmittance) of the transmittance.
From the result that the Δ transmittance could be reduced in each example, it was confirmed that the near-infrared absorber was effective against photodegradation. As a result, it was found that the near-infrared absorbing layer is excellent in preventing photodegradation of the near-infrared absorbing agent.
実施例1〜5の粒状紫外線吸収剤は、比較例1と比べて粉塵性や流動性に優れており、比較例2と比べて溶融混練性に優れることから、良好な粉体特性を示すことが分かった。また、実施例1〜5の化合物は、紫外線吸収特性に優れているため、紫外線吸収剤として好適に利用できることが分かった。 The granular ultraviolet absorbers of Examples 1 to 5 are excellent in dustiness and fluidity as compared with Comparative Example 1, and are excellent in melt kneading property as compared with Comparative Example 2, and thus exhibit good powder characteristics. I found out. Further, it was found that the compounds of Examples 1 to 5 can be suitably used as an ultraviolet absorber because they have excellent ultraviolet absorption characteristics.
この出願は、2018年3月30日に出願された日本出願特願2018−067812号および2018年3月30日に出願された日本出願特願2018−067830号を基礎とする優先権を主張し、その開示の全てをここに取り込む。 This application claims priority on the basis of Japanese application Japanese Patent Application No. 2018-067812 filed on March 30, 2018 and Japanese application Japanese Patent Application No. 2018-067830 filed on March 30, 2018. , All of its disclosures are taken here.
Claims (7)
前記トリアジン系化合物が、下記化合物No.1を含み、
下記篩残分量の測定手順を実施したとき、当該粒状紫外線吸収剤を目開き5.0mm篩に通した際の不通過分量が0wt%であり、
下記篩残分量の測定手順を実施したとき、当該粒状紫外線吸収剤の目開き1.0mm篩の通過分量が1.0wt%以上15.0wt%以下であり、
下記の篩残分量の測定手順に基づいて算出される、
目開き4.0mmの篩上の篩残分量が、0.3wt%以上1.5wt%以下であり、
目開き2.8mmの篩上の篩残分量が、5.0wt%以上25.0wt%以下であり、
目開き2.0mmの篩上の篩残分量が、25.0wt%以上35.0wt%以下であり、
目開き1.0mmの篩上の篩残分量が、35.0wt%以上55.0wt%以下である、という粒度分布を満たす、粒状紫外線吸収剤。
(篩残分量の測定手順)
当該粒状紫外線吸収剤の所定量(g)を、目開き4.0mm篩、目開き2.8mm篩、目開き2.0mm篩、及び目開き1.0mm篩を用いて、この順で篩分を行い、各篩上に残存した当該粒状紫外線吸収剤の残存重量(g)を測定し、前記所定量に対する前記残存重量の重量割合(wt%)を篩残分量として算出する。
The triazine-based compound is the following compound No. Including 1
When the following procedure for measuring the residual amount of the sieve was carried out, the amount of non-passing when the granular ultraviolet absorber was passed through a 5.0 mm sieve with a mesh size was 0 wt%.
When the following procedure for measuring the residual amount of the sieve was carried out, the amount of the granular ultraviolet absorber passing through the 1.0 mm mesh sieve was 1.0 wt% or more and 15.0 wt% or less.
Calculated based on the following procedure for measuring the amount of sieve residue,
The residual amount of the sieve on the sieve having a mesh size of 4.0 mm is 0.3 wt% or more and 1.5 wt% or less.
The residual amount of the sieve on the sieve having a mesh size of 2.8 mm is 5.0 wt% or more and 25.0 wt% or less.
The amount of sieve residue on the sieve having a mesh size of 2.0 mm is 25.0 wt% or more and 35.0 wt% or less.
A granular ultraviolet absorber that satisfies a particle size distribution in which the amount of residual sieve residue on a sieve having a mesh size of 1.0 mm is 35.0 wt% or more and 55.0 wt% or less.
(Measurement procedure for sieve residue)
A predetermined amount (g) of the granular ultraviolet absorber is sieved in this order using a 4.0 mm mesh sieve, a 2.8 mm mesh sieve, a 2.0 mm mesh sieve, and a 1.0 mm mesh sieve. Is performed, the residual weight (g) of the granular ultraviolet absorber remaining on each sieve is measured, and the weight ratio (wt%) of the residual weight to the predetermined amount is calculated as the sieve residual amount.
前記トリアジン系化合物が、粉末X線回折分析パターンにおいて、回折角2θが5.00°以上6.50°以下の範囲内に極大ピークを有することを特徴とする、粒状紫外線吸収剤。 The granular ultraviolet absorber according to claim 1.
A granular ultraviolet absorber, wherein the triazine compound has a maximum peak in a diffraction angle 2θ of 5.00 ° or more and 6.50 ° or less in a powder X-ray diffraction analysis pattern.
前記トリアジン系化合物の極大ピークの半値幅が、0.05°以上0.20°以下である、粒状紫外線吸収剤。 The granular ultraviolet absorber according to claim 2.
A granular ultraviolet absorber having a half-value width of a maximum peak of the triazine compound of 0.05 ° or more and 0.20 ° or less.
前記トリアジン系化合物の極大ピークの相対強度を100としたとき、当該相対強度30以上60以下の回折ピークが、回折角2θが3.0°以上45.0°以下の範囲内に存在しないことを特徴とする、粒状紫外線吸収剤。 The granular ultraviolet absorber according to claim 2 or 3.
When the relative intensity of the maximum peak of the triazine compound is 100, the diffraction peak having a relative intensity of 30 or more and 60 or less does not exist in the range where the diffraction angle 2θ is 3.0 ° or more and 45.0 ° or less. A characteristic granular UV absorber.
前記トリアジン系化合物の極大ピークの相対強度を100としたとき、当該相対強度1以上5以下の回折ピークが、回折角2θが45.0°超60.0°以下の範囲内に存在しないことを特徴とする、粒状紫外線吸収剤。 The granular ultraviolet absorber according to any one of claims 2 to 4.
When the relative intensity of the maximum peak of the triazine compound is 100, the diffraction peak having a relative intensity of 1 or more and 5 or less does not exist in the range where the diffraction angle 2θ is more than 45.0 ° and 60.0 ° or less. A characteristic granular UV absorber.
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