WO2023199978A1 - Composition d'additif de résine, procédé de production d'une composition d'additif de résine, procédé d'amélioration de la résistance au blocage d'une composition d'additif de résine, composition de résine, structure de résine, procédé de production d'une composition de résine, composé d'amine encombrée et antioxydant phénolique - Google Patents
Composition d'additif de résine, procédé de production d'une composition d'additif de résine, procédé d'amélioration de la résistance au blocage d'une composition d'additif de résine, composition de résine, structure de résine, procédé de production d'une composition de résine, composé d'amine encombrée et antioxydant phénolique Download PDFInfo
- Publication number
- WO2023199978A1 WO2023199978A1 PCT/JP2023/015032 JP2023015032W WO2023199978A1 WO 2023199978 A1 WO2023199978 A1 WO 2023199978A1 JP 2023015032 W JP2023015032 W JP 2023015032W WO 2023199978 A1 WO2023199978 A1 WO 2023199978A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin
- additive composition
- resin additive
- hindered amine
- phenolic antioxidant
- Prior art date
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 155
- 239000011347 resin Substances 0.000 title claims abstract description 155
- 239000000654 additive Substances 0.000 title claims abstract description 133
- 239000000203 mixture Substances 0.000 title claims abstract description 130
- -1 amine compound Chemical class 0.000 title claims abstract description 127
- 230000000996 additive effect Effects 0.000 title claims abstract description 126
- 239000002530 phenolic antioxidant Substances 0.000 title claims abstract description 61
- 239000011342 resin composition Substances 0.000 title claims description 49
- 230000000903 blocking effect Effects 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 19
- 229920003002 synthetic resin Polymers 0.000 claims description 53
- 239000000057 synthetic resin Substances 0.000 claims description 53
- 238000002156 mixing Methods 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 35
- 150000004665 fatty acids Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 19
- 239000000377 silicon dioxide Substances 0.000 description 10
- 239000004743 Polypropylene Substances 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
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- 239000000843 powder Substances 0.000 description 6
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- 238000000576 coating method Methods 0.000 description 5
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- 239000007924 injection Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
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- 239000010959 steel Substances 0.000 description 4
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- 238000010521 absorption reaction Methods 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- 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 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 229920006038 crystalline resin Polymers 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
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- 238000005259 measurement Methods 0.000 description 2
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- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
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- 239000004645 polyester resin Substances 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- LDTAOIUHUHHCMU-UHFFFAOYSA-N 3-methylpent-1-ene Chemical compound CCC(C)C=C LDTAOIUHUHHCMU-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 229910001335 Galvanized steel Inorganic materials 0.000 description 1
- 239000004706 High-density cross-linked polyethylene Substances 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920003355 Novatec® Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000004699 Ultra-high molecular weight polyethylene Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229920006127 amorphous resin Polymers 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical compound COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000010891 electric arc Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920005680 ethylene-methyl methacrylate copolymer Polymers 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000005003 food packaging material Substances 0.000 description 1
- 239000008397 galvanized steel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 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 1
- 229920004932 high density cross-linked polyethylene Polymers 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007561 laser diffraction method Methods 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
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- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 1
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- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
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- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 239000010935 stainless steel Substances 0.000 description 1
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- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
-
- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
-
- 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
Definitions
- the present invention relates to a resin additive composition, a method for producing a resin additive composition, a method for improving blocking resistance of a resin additive composition, a resin composition, a resin structure, a method for producing a resin composition, a hindered amine compound, and a phenol.
- the present invention relates to antioxidants.
- Patent Document 1 describes a resin additive composition in which specific silica is impregnated with a specific hindered amine compound. Further, Patent Document 1 describes that this resin additive composition has excellent handleability and can impart excellent weather resistance to the resin.
- the present inventors further investigated and found that by blending a resin additive composition containing a hindered amine compound, a phenolic antioxidant, and a carrier into a synthetic resin, it is possible to impart excellent weather resistance to the synthetic resin.
- the present invention has now been completed.
- one aspect of the present invention describes the following resin additive composition, method for producing a resin additive composition, method for improving blocking resistance of a resin additive composition, resin composition, resin structure, and resin composition.
- Methods of production, hindered amine compounds, and phenolic antioxidants are provided.
- (B-1) a hindered amine compound;
- (B-2) A phenolic antioxidant, A carrier;
- a resin additive composition comprising: 2.
- 3. 1.
- the resin additive composition described in A resin additive composition in which the hindered amine compound (B-1) contains one or more compounds represented by the following general formula (1).
- R 1 represents a hydrogen atom or a methyl group
- R 2 to R 5 each independently represents an alkyl group having 1 to 6 carbon atoms
- R 6 represents a carbon number of 7 to 6. 29 fatty acid residues
- R 7 and R 8 each independently represent an alkyl group having 1 to 6 carbon atoms, n represents 1, 2 or 4, and when n is 1, X is a carbon atom.
- R 9 to R 14 each independently represent an alkyl group having 1 to 6 carbon atoms, and Y represents a trivalent group represented by the following formula (c) or (d). represent.)
- * represents the position bonded to the methylene group.
- a resin composition comprising the resin additive composition according to any one of the above. 9. 8. A resin structure formed from the resin composition described in . 10.
- a method for producing a resin composition comprising the step of blending the resin additive composition according to any one of the above. 11.
- (B-1) a hindered amine compound;
- (B-2) A phenolic antioxidant, A carrier;
- a hindered amine compound for use in a resin additive composition comprising: 12.
- R 1 represents a hydrogen atom or a methyl group
- R 2 to R 5 each independently represents an alkyl group having 1 to 6 carbon atoms
- R 6 represents a carbon atom number of 7 to 6. 29 fatty acid residues
- (B-1) a hindered amine compound
- (B-2) A phenolic antioxidant, A carrier
- a phenolic antioxidant for use in a resin additive composition comprising. 14. 13.
- R 7 and R 8 each independently represent an alkyl group having 1 to 6 carbon atoms
- n represents 1, 2 or 4, and when n is 1, X is a carbon atom.
- a resin additive composition capable of imparting excellent weather resistance to a synthetic resin
- a method for producing a resin additive composition a method for improving blocking resistance of a resin additive composition, a resin composition, and a resin structure.
- a method for producing a resin composition a hindered amine compound, and a phenolic antioxidant.
- the resin additive composition of the present embodiment includes (B-1) a hindered amine compound, (B-2) a phenolic antioxidant, and a carrier.
- the resin additive composition of this embodiment can impart excellent weather resistance to synthetic resins. Further, the resin additive composition of the present embodiment is unlikely to cause sticking (blocking) during storage, that is, has excellent blocking resistance.
- the hindered amine compound preferably contains at least one compound having a melting point of 80°C or lower, preferably 60°C or lower, more preferably 40°C or lower.
- the resin additive composition has excellent dispersibility in the synthetic resin.
- the hindered amine compound (B-1) may consist only of compounds having a melting point of 80°C or lower, preferably 60°C or lower, and more preferably 40°C or lower.
- the melting point refers to the value measured using a melting point meter manufactured by Mettler Toledo (model number MP-90) at a temperature increase rate of 1° C./min.
- the hindered amine compound preferably contains one or more compounds represented by the following general formula (1). In this case, even better weather resistance can be imparted to the synthetic resin.
- R 1 represents a hydrogen atom or a methyl group
- R 2 to R 5 each independently represents an alkyl group having 1 to 6 carbon atoms
- R 6 represents a carbon atom number of 7 to 29 represents a fatty acid residue.
- Examples of the alkyl group having 1 to 6 carbon atoms represented by R 2 to R 5 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, and pentyl group. group, sec-pentyl group, tert-pentyl group, hexyl group, etc.
- the fatty acid residue having 7 to 29 carbon atoms represented by R 6 is a residue obtained by removing a carboxyl group from a fatty acid having 8 to 30 carbon atoms, such as n-heptyl group, n-octyl group, n-nonyl group, etc.
- n-decyl group n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group group, n-eicosyl group, n-henicosyl group, n-docosyl group, n-tricosyl group, n-pentacosyl group, n-heptacosyl group, n-nonacodecyl group, and the like.
- R 1 in the above general formula (1) is a methyl group.
- the resin additive composition has excellent acid resistance, and has excellent weather resistance under conditions where it is exposed to an acidic atmosphere such as acid rain.
- R 2 to R 5 in the above general formula (1) are preferably a methyl group, a tert-butyl group, or a tert-pentyl group, and a methyl group It is particularly preferable that
- R 6 in the above general formula (1) has a carbon atom number of 9 to 25.
- a fatty acid residue having 11 to 21 carbon atoms is preferred, and a fatty acid residue having 11 to 21 carbon atoms is more preferred.
- R 6 is preferably a residue obtained by removing a carboxyl group from a saturated fatty acid.
- the hindered amine compound is, for example, the following compound No. A1 ⁇ No. It may contain one or more selected from the group consisting of A6.
- the phenolic antioxidant preferably contains at least one compound with a melting point of 200°C or lower, preferably 120°C or lower, more preferably 80°C or lower, even more preferably 60°C or lower.
- the resin additive composition has excellent dispersibility in the synthetic resin.
- the phenolic antioxidant may consist only of compounds with a melting point of 200°C or lower, preferably 120°C or lower, more preferably 80°C or lower, even more preferably 60°C or lower.
- Examples of the phenolic antioxidant include hindered phenol compounds, semi-hindered phenol compounds, unhindered phenol compounds, and the like.
- the phenolic antioxidant preferably contains a hindered phenol compound or a semi-hindered phenol compound, and more preferably contains a hindered phenol compound. preferable.
- the phenolic antioxidant preferably contains one or more compounds represented by the following general formula (2). In this case, even better weather resistance can be imparted to the synthetic resin.
- R 7 and R 8 each independently represent an alkyl group having 1 to 6 carbon atoms, n represents 1, 2 or 4, and when n is 1, X represents the number of carbon atoms. 7 to 29 fatty acid residues, when n is 2, X represents a divalent group represented by the following formula (a), and when n is 4, X represents the following formula (b). represents a tetravalent group.
- the phenolic antioxidant preferably contains one or more compounds represented by the above general formula (2) where n is 1 or 2, and the above general formula where n is 1. It is more preferable to include one or more compounds represented by (2).
- the dark-colored synthetic resin composition obtained by blending the resin additive composition and the black pigment has excellent weather resistance.
- R 7 and R 8 examples include those exemplified as the alkyl group having 1 to 6 carbon atoms represented by R 2 to R 5 in general formula (1) above.
- R 7 and R 8 are preferably a methyl group, a tert-butyl group or a tert-pentyl group, and particularly preferably a tert-butyl group.
- examples of the fatty acid residue having 7 to 29 carbon atoms represented by X include those exemplified as the fatty acid residue having 7 to 29 carbon atoms represented by R 6 in the general formula (1) above. It will be done.
- X is a fatty acid having 10 to 26 carbon atoms. It is preferably a residue, and more preferably a fatty acid residue having 12 to 22 carbon atoms. Furthermore, when n is 1, it is preferable that X is a residue obtained by removing a carboxyl group from a saturated fatty acid.
- the phenolic antioxidant may contain one or more compounds represented by the following general formula (3).
- the blocking resistance of the resin additive composition becomes even more excellent.
- the resin additive composition has excellent heat resistance.
- the dark-colored synthetic resin composition obtained by blending the resin additive composition and the black pigment has excellent weather resistance.
- R 9 to R 14 each independently represent an alkyl group having 1 to 6 carbon atoms
- Y represents a trivalent group represented by the following formula (c) or (d). .
- R 9 to R 14 examples include those exemplified as the alkyl group having 1 to 6 carbon atoms represented by R 2 to R 5 in general formula (1) above.
- R 9 to R 14 are preferably a methyl group, a tert-butyl group or a tert-pentyl group, and particularly preferably a tert-butyl group.
- Y is the above formula (c).
- the blocking resistance of the resin additive composition becomes even more excellent.
- the heat resistance of the resin additive composition becomes even more excellent.
- the weather resistance of the dark-colored synthetic resin composition obtained by blending the resin additive composition and the black pigment becomes more excellent.
- the phenolic antioxidant has the above general formula where n is 1. It may contain both the compound represented by (2) and the compound represented by the above general formula (3).
- the phenolic antioxidant is, for example, the following compound No. B1 ⁇ No. It may contain one or more selected from the group consisting of B5.
- the ratio Z 2 /Z 1 of the content Z 2 of the (B-2) phenolic antioxidant to the content Z 1 of the hindered amine compound (B-1) is For example, it may be 0.05 or more and 10.0 or less.
- Z 2 /Z 1 is preferably 0.1 or more and 4.0 or less, more preferably 0.15 or more and 2.5 or less, and 0. More preferably, it is .2 or more and 1.5 or less.
- the carrier is a substance that adsorbs at least one component included in the resin additive composition.
- Specific examples of carriers include inorganic carriers such as silica, alumina, silicate, zeolite, and carbon black, low-molecular organic carriers such as cyclodextrin, crown ether, and calixarene, and polymeric organic carriers such as synthetic resins. Can be mentioned. These may be used alone or in combination of two or more.
- the carrier contained in the resin additive composition of the present embodiment preferably contains something other than a polymeric organic carrier, and may include one or more selected from the group consisting of an inorganic carrier and a low-molecular organic carrier. is more preferable, and it is even more preferable that an inorganic carrier is included.
- the resin additive composition will have excellent blocking resistance.
- the inorganic carrier preferably contains silica, alumina, silicate or zeolite, more preferably contains silica, silicate or zeolite, and contains silica or silicic acid. It is more preferable to contain salt, and it is especially preferable to contain silica.
- silica may be either a natural product or a synthetic product, and may be crystalline or amorphous.
- silica may be manufactured by a wet method such as a gel method or a precipitation method, or by a dry method such as a combustion method, arc discharge, or plasma discharge.
- the silica is preferably produced by a wet method, and preferably by a gel method. Particularly preferred.
- the form of the carrier contained in the resin additive composition of this embodiment may be, for example, powder, flake, granule, sheet, etc.
- the carrier is preferably a powder.
- the carrier is preferably porous.
- the volume average particle diameter of the carrier may be, for example, 0.1 to 100 ⁇ m. From the viewpoint of improving the blocking resistance of the resin additive composition, the volume average particle diameter of the carrier is preferably 1 to 50 ⁇ m, more preferably 3 to 25 ⁇ m. In this embodiment, the volume average particle diameter of the carrier is a 50% cumulative particle diameter measured by a laser diffraction/scattering method in accordance with ISO-13320.
- the specific surface area of the carrier contained in the resin additive composition of the present embodiment may be, for example, 100 to 1000 m 2 /g.
- the specific surface area of the carrier is preferably 120 to 800 m 2 /g, more preferably 200 to 750 m 2 /g, and more preferably 250 to 800 m 2 /g. It is more preferably 700 m 2 /g, and even more preferably 400 to 600 m 2 /g.
- the specific surface area of the carrier is the BET specific surface area measured in accordance with JIS Z 8830.
- the water content of the carrier contained in the resin additive composition of the present embodiment may be, for example, 0.5 to 10% by mass.
- the water content of the carrier is preferably 2 to 9% by mass, more preferably 3 to 8% by mass, and 3.5% by mass. More preferably, the content is 7% by mass.
- the oil absorption amount of the carrier contained in the resin additive composition of the present embodiment may be, for example, 10 to 1000 mL/100 g.
- the oil absorption amount of the carrier is preferably 100 to 500 mL/100 g, more preferably 150 to 300 mL/100 g.
- the oil absorption amount of the carrier is measured in accordance with JIS K 5101.
- the content of the carrier is, for example, 100 parts by mass of the total amount of (B-1) hindered amine compound and (B-2) phenolic antioxidant contained in the resin additive composition.
- the amount may be 10 to 1000 parts by mass.
- the content of the carrier is determined by the amount of (B-1) hindered amine compound and (B-2) phenolic antioxidant. It is preferably 20 to 500 parts by mass, more preferably 25 to 400 parts by mass, even more preferably 33 to 300 parts by mass, and even more preferably 50 to 200 parts by mass, based on 100 parts by mass of the total amount. It is even more preferable.
- the resin additive composition of the present embodiment may further contain (B-3) a benzoate compound.
- (B-3) a benzoate compound.
- the benzoate compound preferably contains one or more compounds represented by the following general formula (5).
- R 21 and R 22 each independently represent an alkyl group having 1 to 6 carbon atoms, and R 23 represents a fatty acid residue having 7 to 29 carbon atoms.
- Examples of the alkyl group having 1 to 6 carbon atoms represented by R 21 and R 22 include those exemplified as the alkyl group having 1 to 6 carbon atoms represented by R 2 to R 5 in general formula (1) above. . From the viewpoint of imparting better weather resistance to the synthetic resin, R 21 and R 22 are preferably a methyl group, a tert-butyl group or a tert-pentyl group, and particularly preferably a tert-butyl group. Furthermore, examples of the fatty acid residue having 7 to 29 carbon atoms represented by R 23 include those exemplified as the fatty acid residue having 7 to 29 carbon atoms represented by R 6 in the above general formula (1).
- R 23 is preferably a fatty acid residue having 10 to 26 carbon atoms, More preferably, it is a fatty acid residue having 12 to 22 carbon atoms. Furthermore, R 23 is preferably a residue obtained by removing a carboxyl group from a saturated fatty acid.
- Benzoate compound is, for example, the following compound No. C1 ⁇ No. It may contain one or more selected from the group consisting of C5.
- the ratio Z 3 of the content Z 3 of the benzoate compound (B-3) to the content Z 1 of the hindered amine compound (B-1) /Z 1 may be, for example, 0.05 or more and 10.0 or less in terms of mass.
- Z 3 /Z 1 is preferably 0.1 or more and 4.0 or less, more preferably 0.15 or more and 2.5 or less, and 0. More preferably, it is .2 or more and 1.5 or less.
- the resin additive composition of the present embodiment may further contain antioxidants other than phenolic antioxidants, ultraviolet absorbers, fatty acid metal salts, lubricants, hydrotalcites, optical brighteners, pigments, It may also contain resin additives such as dyes (hereinafter referred to as "other additives (I)").
- the hindered amine compound (B-1) is adsorbed on the carrier.
- seepage of the hindered amine compound (B-1) from the resin additive composition can be suppressed.
- the resin additive composition can have excellent blocking resistance, and the resin additive composition It is possible to improve the ease of weighing and handling of objects.
- the mode of adsorption includes, for example, chemical adsorption and physical adsorption. Among these, chemisorption is preferred from the viewpoint of improving the blocking resistance of the resin additive composition.
- the hindered amine compound (B-1) may be adsorbed only on the surface of the carrier (surface adsorption) or may be impregnated into the carrier. From the viewpoint of further suppressing the seepage of the hindered amine compound (B-1) from the resin additive composition, the hindered amine compound (B-1) is preferably impregnated into a carrier.
- "(B-1) the hindered amine compound is impregnated into the carrier” means that the carrier is porous and (B-1) the hindered amine compound is impregnated in the pores on the surface of the carrier and the voids inside the carrier.
- the hindered amine compound (B-1) in liquid form is adsorbed to the pores on the surface of the carrier and the pores inside the carrier, and the hindered amine compound in liquid form (B-1) is adsorbed to the pores.
- (B-2) a phenolic antioxidant may be further adsorbed on the carrier.
- the resin additive composition of the present embodiment further contains (B-3) a benzoate compound or the above-mentioned other additive (I), one or more of these components are adsorbed on the carrier.
- the hindered amine compound (B-1) is used to be blended into a resin additive composition having anti-blocking properties as described above.
- (B-1) a hindered amine compound is a hindered amine compound for use in a resin additive composition containing (B-1) a hindered amine compound, (B-2) a phenolic antioxidant, and a carrier.
- the phenolic antioxidant (B-2) is used to be blended into the resin additive composition having anti-blocking properties as described above.
- the phenolic antioxidant is used in a resin additive composition containing (B-1) the hindered amine compound, (B-2) the phenolic antioxidant, and a carrier. It can be used as a phenolic antioxidant.
- the method for producing a resin additive composition of the present embodiment includes a blending step of blending (B-1) a hindered amine compound, (B-2) a phenolic antioxidant, and a carrier.
- an example of the resin additive composition includes (B-1) a hindered amine compound, (B-2) a phenolic antioxidant, a carrier, and optionally (B-3) a benzoate compound and the other additives mentioned above.
- It is produced by a production method including a blending step of blending and uniformly mixing (I).
- the mixing method is not particularly limited, and for example, a known mixing device such as an FM mixer may be used for mixing.
- a method of mixing (B-1) hindered amine compound in a liquid or molten state with a carrier under atmospheric pressure or reduced pressure a method of mixing a solution of (B-1) hindered amine compound in a solvent with a carrier,
- the hindered amine compound (B-1) may be adsorbed onto the carrier by a method such as removing the solvent after mixing with the carrier.
- the mixing method, mixing environmental conditions, and mixing order of each component in the above blending step are not particularly limited.
- a method for improving the blocking resistance of a resin additive composition can be provided.
- a method for improving blocking resistance of a resin additive composition includes a blending step of blending (B-1) a hindered amine compound, (B-2) a phenolic antioxidant, and a carrier.
- B-1 a hindered amine compound
- B-2 a phenolic antioxidant
- a carrier a carrier for a phenolic antioxidant
- the conditions similar to the compounding step of the above-mentioned manufacturing method can be adopted for the compounding step in the method for improving blocking resistance.
- (A) synthetic resin may be further blended, if necessary.
- the shape of the resin additive composition of this embodiment may be, for example, pellet, pill, or powder. From the viewpoint of suppressing seepage of the hindered amine compound (B-1) from the resin additive composition, pellets or pills are preferred, and pellets are particularly preferred.
- the resin composition of this embodiment includes at least (A) a synthetic resin and the resin additive composition described above.
- the resin composition of this embodiment has excellent weather resistance.
- thermoplastic resins examples include thermoplastic resins and thermosetting resins.
- thermoplastic resins include polyolefin resins, polyamide resins, polyester resins, polyacetal resins, polylactic acid, crystalline resins such as polyphenylene sulfide, polycarbonate resins, styrene resins, acrylic resins, urethane resins, etc.
- examples include amorphous resins such as halogen resins, petroleum resins, coumaron resins, polyvinyl alcohol, polyvinyl acetate, and polyphenylene oxide, and thermoplastic elastomers.
- thermosetting resin examples include phenol resin, urea resin, melamine resin, epoxy resin, unsaturated polyester resin, and synthetic rubber.
- the synthetic resin may be contained singly or in combination of two or more.
- the synthetic resin (A) may be a copolymer or a polymer alloy.
- the synthetic resin is preferably a thermoplastic resin, more preferably a crystalline resin, and preferably contains a polyolefin resin.
- polyolefin resins include polyethylene resins such as low density polyethylene, linear low density polyethylene, high density polyethylene, crosslinked polyethylene, and ultra-high molecular weight polyethylene, homopolypropylene, random copolymer polypropylene, block copolymer polypropylene, and impact copolymer polypropylene.
- high impact copolymer polypropylene polypropylene resins such as maleic anhydride modified polypropylene, polybutene-1, cycloolefin polymer, poly-3-methyl-1-butene, poly-3-methyl-1-pentene, poly-4-methyl
- examples thereof include ⁇ -olefin polymers such as -1-pentene, ethylene-methyl methacrylate copolymers, and ⁇ -olefin copolymers such as ethylene-vinyl acetate copolymers.
- the type of catalyst used for example, Ziegler catalyst, metallocene catalyst, etc.
- polyolefin resins polypropylene resins are particularly preferred.
- the content of the resin additive composition may be, for example, 0.001 to 10 parts by mass based on 100 parts by mass of the (A) synthetic resin.
- the content of the resin additive composition is (A) 100% synthetic resin. It is preferably 0.01 to 5 parts by weight, more preferably 0.05 to 3 parts by weight, and even more preferably 0.1 to 1 part by weight.
- the resin composition of this embodiment may further include the above-mentioned other additives (I), a flame retardant, and a flame retardant auxiliary agent, which are exemplified as components that may be included in the resin additive composition of this embodiment, as necessary. , fillers, antistatic agents, curing accelerating catalysts, organic solvents, anti-yellowing agents, leveling agents, antifoaming agents, thickeners, antisettling agents, antifogging agents, and other resin additives (hereinafter referred to as ⁇ other additives'') (II)").
- ⁇ other additives'' II
- the method for producing a resin composition of the present embodiment includes the step of blending the above-mentioned resin additive composition into (A) a synthetic resin. According to the method for producing a resin composition of the present embodiment, a resin composition with excellent weather resistance can be produced. In addition, according to the method for producing a resin composition of the present embodiment, a resin additive composition having excellent blocking resistance and excellent metering and handling properties can be used as an additive to be blended into the synthetic resin, so that it can be uniformly produced. It is possible to efficiently produce resin compositions of high quality.
- the synthetic resin and the resin additive composition are mixed in various mixers such as a tumbler or an FM mixer.
- mixers such as a tumbler or an FM mixer.
- examples include a method of pre-mixing and then melt-kneading with a Banbury mixer, roll, Brabender, single-screw kneading extruder, twin-screw kneading extruder, kneader, or the like.
- the resin composition may be manufactured without premixing the respective components or by premixing only a part of the components and supplying the mixture to an extruder using a feeder and melt-kneading it.
- a resin composition obtained by premixing some of the components and supplying the mixture to an extruder and melt-kneading is used as a masterbatch, which is then mixed with other components and melt-kneaded again to produce a resin composition.
- the synthetic resin (A) used in the above-mentioned mixing/kneading step may have a predetermined shape such as powder, pellet, etc., or fibrous.
- the resin composition of the present embodiment may be solid, for example, and may have a certain shape such as powder, granules, pellets, briquettes, tablets, or sheets. Moreover, the resin composition of this embodiment may be a liquid, a slurry, an emulsion, or a paste.
- the resin structure of this embodiment is formed from the above resin composition.
- the resin structure of this embodiment has excellent weather resistance.
- the resin structure may be partially or entirely composed of a resin composition. However, it is preferable that the entire resin structure is made of a resin composition.
- Specific examples of the resin structure include a molded article obtained by molding a resin composition, a coating film obtained by curing a paint made of the resin composition, and the like. Among these, molded products obtained by molding a resin composition are preferred.
- examples of molded products include injection molded products, fibers, biaxially stretched films, uniaxially stretched films, unstretched films, sheets, thermoformed products, extrusion blow molded products, injection blow molded products, and injection stretch blow molded products. , profile extrusion molded products, rotary molded products, etc., and more specifically, vehicle parts, household goods, food packaging materials, etc.
- a coating film for example, metals such as galvanized steel sheets, zinc alloy-plated steel sheets, stainless steel sheets, tin-plated steel sheets, polymethyl methacrylate resin, polycarbonate resin, polyester resin, polystyrene resin, ABS resin, AS resin, polyamide resin.
- Brushing a paint made of a resin composition onto a base material made of resin such as polyarylate resin, polymethacrylimide resin, polyallyl diglycol carbonate resin, bar coat, spray coat, dip coat, spin coat, curtain, etc.
- resin such as polyarylate resin, polymethacrylimide resin, polyallyl diglycol carbonate resin
- bar coat, spray coat, dip coat, spin coat, curtain etc.
- Examples include a coating film obtained by forming a paint layer by coating using a known method such as coating, and then curing this paint layer using a known method such as room temperature curing, heat curing, or ultraviolet irradiation.
- the (A) synthetic resin, (B-1) hindered amine compound, (B-2) phenolic antioxidant, carrier, filler, and pigment used in this example are as follows.
- Synthetic resin [(A) Synthetic resin]
- ⁇ Synthetic resin 2 Impact copolymer polypropylene (Novatec PP BC03B, manufactured by Nippon Polypro Co., Ltd.)
- ⁇ Synthetic resin 3 Ethylene-1-octene copolymer elastomer (manufactured by Dow, Engage8100)
- the glossiness (gloss value) of each test piece was measured before and during the weatherability test, and from the start of the test, the glossiness of the test piece was 80% or less of the glossiness before the weatherability test.
- the time (h) required for this to occur was defined as the "80% gloss retention time” and was used as an index of weather resistance.
- the glossiness of the test piece was measured using a gloss meter (manufactured by Nippon Denshoku Industries, VG-2000) at a measurement angle of 60°. The results are also listed in Table 2.
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Abstract
La présente invention concerne une composition d'additif de résine contenant (B-1) un composé d'amine encombrée, (B-2) un antioxydant phénolique et un support.
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JPH03197549A (ja) * | 1989-12-27 | 1991-08-28 | Ube Ind Ltd | 塗装性改良ポリプロピレン系樹脂組成物 |
JP2001329178A (ja) * | 2000-05-24 | 2001-11-27 | Asahi Denka Kogyo Kk | ガラス繊維強化熱可塑性樹脂組成物 |
JP2001342362A (ja) * | 2000-05-31 | 2001-12-14 | Asahi Denka Kogyo Kk | 含酸素ポリマー組成物 |
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JP2006249040A (ja) * | 2005-03-14 | 2006-09-21 | Tokuyama Corp | 歯科用硬化性組成物 |
JP2014029953A (ja) * | 2012-07-31 | 2014-02-13 | Mitsui Chemicals Inc | 太陽電池封止材および太陽電池モジュール |
WO2019188937A1 (fr) * | 2018-03-26 | 2019-10-03 | 株式会社Adeka | Composition de résine de chlorure de vinyle pour des feuilles imperméables à l'eau et feuille imperméable à l'eau |
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JPS6136345A (ja) * | 1984-07-30 | 1986-02-21 | Sumitomo Chem Co Ltd | エチレン・プロピレン系加硫ゴム組成物 |
JPS6346246A (ja) * | 1986-04-14 | 1988-02-27 | Sumitomo Chem Co Ltd | エチレン・α−オレフイン共重合系加硫ゴム組成物 |
JPH03197549A (ja) * | 1989-12-27 | 1991-08-28 | Ube Ind Ltd | 塗装性改良ポリプロピレン系樹脂組成物 |
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JP2006249040A (ja) * | 2005-03-14 | 2006-09-21 | Tokuyama Corp | 歯科用硬化性組成物 |
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WO2019188937A1 (fr) * | 2018-03-26 | 2019-10-03 | 株式会社Adeka | Composition de résine de chlorure de vinyle pour des feuilles imperméables à l'eau et feuille imperméable à l'eau |
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