WO2019194117A1 - ポリエステル樹脂組成物 - Google Patents
ポリエステル樹脂組成物 Download PDFInfo
- Publication number
- WO2019194117A1 WO2019194117A1 PCT/JP2019/014437 JP2019014437W WO2019194117A1 WO 2019194117 A1 WO2019194117 A1 WO 2019194117A1 JP 2019014437 W JP2019014437 W JP 2019014437W WO 2019194117 A1 WO2019194117 A1 WO 2019194117A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- tert
- polyester resin
- butyl
- bis
- phosphate
- Prior art date
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- 229920001225 polyester resin Polymers 0.000 title claims abstract description 89
- 239000004645 polyester resin Substances 0.000 title claims abstract description 89
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 54
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- -1 2- (3- ( 3-tert-butyl-4-hydroxy-5-methylphenyl) -propionyloxy) -1,1-dimethylethyl Chemical group 0.000 claims description 95
- 229910052698 phosphorus Inorganic materials 0.000 claims description 23
- 239000011574 phosphorus Substances 0.000 claims description 23
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 21
- 239000007983 Tris buffer Substances 0.000 claims description 19
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 18
- 239000002530 phenolic antioxidant Substances 0.000 claims description 16
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 14
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 claims description 9
- 150000002009 diols Chemical group 0.000 claims description 9
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical group CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 claims description 8
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical group 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 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 claims description 5
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004383 yellowing Methods 0.000 abstract description 13
- 230000006866 deterioration Effects 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 53
- 239000003054 catalyst Substances 0.000 description 30
- 229910019142 PO4 Inorganic materials 0.000 description 29
- 235000021317 phosphate Nutrition 0.000 description 29
- 239000010452 phosphate Substances 0.000 description 28
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- 238000000034 method Methods 0.000 description 21
- 150000005673 monoalkenes Chemical class 0.000 description 20
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 238000007037 hydroformylation reaction Methods 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 17
- 125000006353 oxyethylene group Chemical group 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 238000005698 Diels-Alder reaction Methods 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000000654 additive Substances 0.000 description 12
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 150000002903 organophosphorus compounds Chemical class 0.000 description 12
- 238000006722 reduction reaction Methods 0.000 description 12
- 229910002091 carbon monoxide Inorganic materials 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 239000010948 rhodium Substances 0.000 description 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- 229910052703 rhodium Inorganic materials 0.000 description 9
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 150000003284 rhodium compounds Chemical class 0.000 description 8
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000011342 resin composition Substances 0.000 description 7
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical group C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 7
- SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 229920001634 Copolyester Polymers 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 229910052799 carbon Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 230000001771 impaired effect Effects 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- 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
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- QAFOOMOQTYFCFJ-UHFFFAOYSA-N [P]C=O Chemical compound [P]C=O QAFOOMOQTYFCFJ-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 3
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 3
- 239000001177 diphosphate Substances 0.000 description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 3
- 235000011180 diphosphates Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- HBTONAMIPDVQRI-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3-phenylphenyl]fluoren-9-yl]-2-phenylphenoxy]ethanol Chemical compound OCCOC1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OCCO)=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 HBTONAMIPDVQRI-UHFFFAOYSA-N 0.000 description 2
- NQXNYVAALXGLQT-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1(C=2C=CC(OCCO)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 NQXNYVAALXGLQT-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
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- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- HZEFWURFJZUWDE-UHFFFAOYSA-N cyclohexyl dihydrogen phosphite Chemical compound OP(O)OC1CCCCC1 HZEFWURFJZUWDE-UHFFFAOYSA-N 0.000 description 1
- KFYNLYOAEZCCAN-UHFFFAOYSA-N cyclohexyl diphenyl phosphite Chemical compound C1CCCCC1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 KFYNLYOAEZCCAN-UHFFFAOYSA-N 0.000 description 1
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- FCGAXGNQRRDUMJ-UHFFFAOYSA-N cyclohexyl phenyl hydrogen phosphite Chemical compound C=1C=CC=CC=1OP(O)OC1CCCCC1 FCGAXGNQRRDUMJ-UHFFFAOYSA-N 0.000 description 1
- GLOQRSIADGSLRX-UHFFFAOYSA-N decyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCC)OC1=CC=CC=C1 GLOQRSIADGSLRX-UHFFFAOYSA-N 0.000 description 1
- FMXOSDJYZPHKBG-UHFFFAOYSA-N decyl dodecyl tridecyl phosphate Chemical compound CCCCCCCCCCCCCOP(=O)(OCCCCCCCCCC)OCCCCCCCCCCCC FMXOSDJYZPHKBG-UHFFFAOYSA-N 0.000 description 1
- ZAQCGJYUIRLDEC-UHFFFAOYSA-N decyl hexadecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCC ZAQCGJYUIRLDEC-UHFFFAOYSA-N 0.000 description 1
- HDFFVHSMHLDSLO-UHFFFAOYSA-M dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)([O-])OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-M 0.000 description 1
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- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
- QBCOASQOMILNBN-UHFFFAOYSA-N didodecoxy(oxo)phosphanium Chemical compound CCCCCCCCCCCCO[P+](=O)OCCCCCCCCCCCC QBCOASQOMILNBN-UHFFFAOYSA-N 0.000 description 1
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- 150000001993 dienes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- DVZIQPGIAQDYQH-UHFFFAOYSA-N diheptyl hydrogen phosphate Chemical compound CCCCCCCOP(O)(=O)OCCCCCCC DVZIQPGIAQDYQH-UHFFFAOYSA-N 0.000 description 1
- MCLZZLXBOLWVSO-UHFFFAOYSA-N dihexyl octadecyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCC)OCCCCCC MCLZZLXBOLWVSO-UHFFFAOYSA-N 0.000 description 1
- XFANRJNPWHYBMX-UHFFFAOYSA-N diicosyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCCCCCC XFANRJNPWHYBMX-UHFFFAOYSA-N 0.000 description 1
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- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
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- FYOYCZHNDCCGCE-UHFFFAOYSA-N diphenyl hydrogen phosphite Chemical compound C=1C=CC=CC=1OP(O)OC1=CC=CC=C1 FYOYCZHNDCCGCE-UHFFFAOYSA-N 0.000 description 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- CYFHLEMYBPQRGN-UHFFFAOYSA-N ditetradecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCC CYFHLEMYBPQRGN-UHFFFAOYSA-N 0.000 description 1
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 1
- RSNDQTNQQQNXRN-UHFFFAOYSA-N dodecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCOP(O)O RSNDQTNQQQNXRN-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- ZUNGGJHBMLMRFJ-UHFFFAOYSA-O ethoxy-hydroxy-oxophosphanium Chemical compound CCO[P+](O)=O ZUNGGJHBMLMRFJ-UHFFFAOYSA-O 0.000 description 1
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- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- UTXVCHVLDOLVPC-UHFFFAOYSA-N ethyl 3-methylbut-2-enoate Chemical compound CCOC(=O)C=C(C)C UTXVCHVLDOLVPC-UHFFFAOYSA-N 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
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- 239000000194 fatty acid Substances 0.000 description 1
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- 238000009499 grossing Methods 0.000 description 1
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- TYCUSKFOGZNIBO-UHFFFAOYSA-N hexadecyl 3,4,5-trihydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 TYCUSKFOGZNIBO-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- BRSRUPSXDXGLDB-UHFFFAOYSA-N hexan-2-yl dinonyl phosphate Chemical compound CCCCCCCCCOP(=O)(OCCCCCCCCC)OC(C)CCCC BRSRUPSXDXGLDB-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- OHRVKCZTBPSUIK-UHFFFAOYSA-N tridodecyl phosphate Chemical compound CCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCC)OCCCCCCCCCCCC OHRVKCZTBPSUIK-UHFFFAOYSA-N 0.000 description 1
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- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- KENFVQBKAYNBKN-UHFFFAOYSA-N trihexadecyl phosphate Chemical compound CCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCC KENFVQBKAYNBKN-UHFFFAOYSA-N 0.000 description 1
- FDGZUBKNYGBWHI-UHFFFAOYSA-N trioctadecyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC FDGZUBKNYGBWHI-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
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- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- DQDKFPSBQOMNOI-UHFFFAOYSA-N tris(2-hexoxyethyl) phosphate Chemical compound CCCCCCOCCOP(=O)(OCCOCCCCCC)OCCOCCCCCC DQDKFPSBQOMNOI-UHFFFAOYSA-N 0.000 description 1
- BZZQSKIYWUCWDM-UHFFFAOYSA-N tris(2-methoxypropyl) phosphate Chemical compound COC(C)COP(=O)(OCC(C)OC)OCC(C)OC BZZQSKIYWUCWDM-UHFFFAOYSA-N 0.000 description 1
- BKHZQJRTFNFCTG-UHFFFAOYSA-N tris(2-methylphenyl) phosphite Chemical compound CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C BKHZQJRTFNFCTG-UHFFFAOYSA-N 0.000 description 1
- WSRKWWQBQDBQRH-UHFFFAOYSA-N tris(2-octylphenyl) phosphite Chemical compound CCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCC)OC1=CC=CC=C1CCCCCCCC WSRKWWQBQDBQRH-UHFFFAOYSA-N 0.000 description 1
- LORSVOJSXMHDHF-UHFFFAOYSA-N tris(4-tert-butylphenyl) phosphate Chemical compound C1=CC(C(C)(C)C)=CC=C1OP(=O)(OC=1C=CC(=CC=1)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1 LORSVOJSXMHDHF-UHFFFAOYSA-N 0.000 description 1
- SAAMKFBWYWFBNY-UHFFFAOYSA-N tris(4-tert-butylphenyl) phosphite Chemical compound C1=CC(C(C)(C)C)=CC=C1OP(OC=1C=CC(=CC=1)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1 SAAMKFBWYWFBNY-UHFFFAOYSA-N 0.000 description 1
- DECPGQLXYYCNEZ-UHFFFAOYSA-N tris(6-methylheptyl) phosphite Chemical compound CC(C)CCCCCOP(OCCCCCC(C)C)OCCCCCC(C)C DECPGQLXYYCNEZ-UHFFFAOYSA-N 0.000 description 1
- JHTBSBZWFPVSMF-UHFFFAOYSA-N tris[2-(2-hydroxyethoxy)ethyl] phosphate Chemical compound OCCOCCOP(=O)(OCCOCCO)OCCOCCO JHTBSBZWFPVSMF-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
- C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
Definitions
- the present invention relates to a polyester resin composition.
- COP cycloolefin polymer described in Patent Document 1
- COP is a resin having high transparency and heat resistance, and can be used in applications requiring transparency and heat resistance. is there.
- Patent Document 1 The COP described in Patent Document 1 is improved to some extent in heat yellowing. However, when the COP is used in an environment where the temperature is high, such as in a car, there is a problem that yellow coloring is observed and transparency and appearance are impaired.
- Patent Document 1 As described above, there is still room for improvement in the technique of Patent Document 1 as a material that can sufficiently prevent yellow coloring that may occur due to use in a high temperature environment and can maintain transparency.
- R 1 is a hydrogen atom
- R 2 and R 3 are each independently a hydrogen atom or CH 3
- n is 0 or 1.
- the polyester resin is a copolymer polyester resin having the unit (A), the diol unit (B), and a dicarboxylic acid or an ester-forming derivative unit (C) thereof,
- the polyester resin composition according to [1] wherein the content of the unit (A) in all the units of the copolymerized polyester resin is 10 to 95 mol%.
- the phenolic antioxidant is 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione, 4,4 ′, 4 ′′-(1-methylpropanyl-3-ylidene) tris (6-tert-butyl-m-cresol), n-octadecyl-3- (3,5-di -Tert-butyl-4-hydroxyphenyl) propionate, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], and 3,9-bis (2- (3- ( 3-tert-butyl-4-hydroxy-5-methylphenyl) -propion
- the phosphorus-based antioxidant is tris (2,4-di-tert-butylphenyl) phosphite and 3,9-bis (2,6-di-tert-butyl-4-methylphenoxy) -2,4,
- the phenolic antioxidant is 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H
- the phosphorus antioxidant is 3,9-bis (2,6-di-tert-butyl-4-methylphenoxy) -2,4,8,10-tetraoxa-3,9-diphosphaspiro [5.5].
- the polyester resin composition according to any one of [3] to [7], which is undecane.
- the polyester resin composition of the present invention can maintain transparency and prevent deterioration of appearance due to yellowing even when used in a high temperature environment.
- the present embodiment a mode for carrying out the present invention (hereinafter simply referred to as “the present embodiment”) will be described in detail.
- the following embodiments are examples for explaining the present invention, and are not intended to limit the present invention to the following contents.
- the present invention can be implemented with appropriate modifications within the scope of the gist thereof.
- the polyester resin composition of this embodiment contains the polyester resin containing the unit (A) represented by following General formula (1), and antioxidant. Since it is configured in this manner, the resin composition of the present embodiment can maintain transparency even when used in a high-temperature environment and can prevent deterioration in appearance due to yellowing.
- the polyester resin in the present embodiment is derived from the norbornane ring skeleton and tends to be excellent in various physical properties such as heat resistance and transparency. However, such physical properties are combined with the yellowing prevention effect of the antioxidant. Thus, the desired effect of the present embodiment can be obtained.
- the resin composition of the present embodiment can remarkably enhance the yellowing prevention effect when used in a high temperature environment, as compared with the case where a known polymer such as COP and an antioxidant are combined, and the transparency is also high. Can be maintained.
- R 1 is a hydrogen atom
- R 2 and R 3 are each independently a hydrogen atom or CH 3
- n is 0 or 1. .
- polyester resin The polyester resin in the present embodiment is not particularly limited as long as it has the unit (A) represented by the general formula (1) (hereinafter also referred to as “unit (A)”).
- unit (C) dicarboxylic acid or ester-forming derivative unit
- the content of the unit (A) with respect to all units of the copolymer polyester resin is 10 to 95 mol%
- the balance between heat resistance and optical properties tends to be better. That is, when the content is 10 mol% or more, sufficient heat resistance and optical properties tend to be ensured, and when the content is 95 mol% or less, good heat resistance and optical properties are ensured.
- the moldability tends to be improved.
- the content of the unit (A) is preferably 15 to 95 mol%, more preferably 20 to 95 mol%.
- R 1 in the general formula (1) is preferably a hydrogen atom or CH 3
- R 2 and R 3 are preferably a hydrogen atom.
- R 1 , R 2 , and R 3 in the general formula (1) are hydrogen atoms.
- n in the said General formula (1) is 1 from a viewpoint of improving heat resistance more.
- the structural unit (B) is not particularly limited as long as it is a unit derived from diol, and specific examples thereof include ethylene glycol, trimethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1, 6-hexanediol, diethylene glycol, propylene glycol, neopentyl glycol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, 1,2-decahydronaphthalenediethanol, 1,3-decahydronaphthalenediethanol, 1,4-decahydronaphthalene diethanol, 1,5-decahydronaphthalene diethanol, 1,6-decahydronaphthalene diethanol, 2,7-decahydronaphthalene diethanol, tetralin dimethanol, norbornane dimethanol, tricyclodeca Dimethanol, pentacyclopentadecane dimethanol, norbornanediol, cyclohexanedi
- the structural unit (B) is preferably a unit derived from an aliphatic diol or a diol having a cardo structure because good transparency is obtained.
- units derived from such aliphatic diols include 1,4-cyclohexanedimethanol, ethylene glycol, tricyclodecane dimethanol, 3,9-bis (1,1-dimethyl-2-hydroxyethyl) -2, Derived from 4,8,10-tetraoxaspiro [5.5] undecane, 1,4: 3,6-dianhydro-D-sorbitol, 2,2,4,4-tetramethyl-1,3-cyclobutanediol Units are more preferred.
- Examples of the unit derived from a diol having a cardo structure include 9,9-bis [4- (2-hydroxyethoxy) phenyl] fluorene, 9,9-bis [4- (2-hydroxyethoxy) -3-methyl. More preferred are units derived from phenyl] fluorene and 9,9-bis [4- (2-hydroxyethoxy) -3-phenylphenyl] fluorene. These optical isomers may be any of a cis isomer, a trans isomer, and a mixture thereof, and are not particularly limited.
- the content of the unit (B) with respect to all units contained in the copolymer polyester resin is preferably 2.5 to 45 mol%, more preferably 2.5 to 40 mol%.
- the above-mentioned units may be included alone or in combination of two or more.
- the structural unit (C) is not particularly limited as long as it is a unit derived from dicarboxylic acid or an ester-forming derivative thereof. Specific examples thereof include terephthalic acid, isophthalic acid, phthalic acid, and 1,3-naphthalenedicarboxylic acid.
- 1,4-naphthalenedicarboxylic acid 1,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 2-methylterephthalic acid, biphenyldicarboxylic acid, tetralindicarboxylic acid and other aromatics Structural units derived from dicarboxylic acids and / or derivatives thereof; succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, dodecanedicarboxylic acid, cyclohexanedicarboxylic acid, decalin dicarboxylic acid, Norbornane dicarboxylic acid, tricyclode Dicarboxylic acid, pentacyclododecanedicarboxylic acid, 3,9-bis (1,1-dimethyl-2-carboxyethyl) -2
- the structural unit (C) is preferably a unit derived from an aliphatic dicarboxylic acid or an ester-forming derivative thereof, or a dicarboxylic acid having a cardo structure or an ester-forming derivative thereof because good transparency is obtained.
- a unit derived from an aliphatic dicarboxylic acid or an ester-forming derivative thereof a unit derived from dimethyl 1,4-cyclohexanedicarboxylate is more preferable from the viewpoint of balance of transparency and heat resistance.
- units derived from a dicarboxylic acid having a cardo structure or an ester-forming derivative thereof include 9,9-bis (methoxycarbonylmethyl) fluorene, 9,9-bis from the viewpoint of the balance of transparency and heat resistance.
- Units derived from (methoxycarbonylethyl) fluorene and 9,9-bis (methoxycarbonylpropyl) fluorene are more preferred.
- These optical isomers may be any of a cis isomer, a trans isomer, and a mixture thereof, and are not particularly limited.
- the content of the unit (C) with respect to all the units contained in the copolymer polyester resin is preferably 2.5 to 45 mol%, more preferably 2.5 to 40 mol%.
- the above-mentioned units may be included alone or in combination of two or more.
- the copolymer polyester resin may contain other units such as a hydroxyl group and a carboxylic acid or an ester-forming derivative unit thereof (A1) in addition to the units (A) to (C).
- the unit (A1) is not particularly limited, but examples thereof include oxyacids such as glycolic acid, lactic acid, hydroxybutyric acid, 2-hydroxyisobutyric acid, hydroxybenzoic acid, 6-hydroxycaproic acid, 4-hydroxycyclohexanecarboxylic acid, and the like. And / or a unit derived from a derivative thereof.
- the glass transition temperature (Tg) of the copolyester resin is not particularly limited, but is preferably 100 ° C. or higher, more preferably 105 ° C. or higher, from the viewpoint of ensuring sufficient heat resistance. More preferably, it is 110 degreeC or more, More preferably, it is 115 degreeC or more, More preferably, it is 120 degreeC or more, More preferably, it is 130 degreeC or more.
- the Tg can be measured by the method described in Examples described later. Moreover, the Tg can be adjusted to the above range, for example, by appropriately adjusting the copolymerization ratio of the raw material monomer of the copolyester resin.
- the molecular weight of the copolyester resin can be appropriately set in consideration of desired performance, handling properties, etc., and is not particularly limited, but the polystyrene-equivalent weight average molecular weight (Mw) is 5000 to 200,000. And more preferably 10,000 to 100,000. When Mw is 5,000 or more, heat resistance tends to be preferably ensured, and when Mw is 200,000 or less, the melt viscosity becomes better, the resin after production is easily extracted, and further the flow From the viewpoint of properties, it tends to be easy to perform injection molding in a molten state.
- Mw polystyrene-equivalent weight average molecular weight
- the copolymerized polyester resin in the present embodiment can be obtained by copolymerizing monomers corresponding to the units (A) to (C).
- monomers corresponding to the units (A) to (C) corresponding to the units (A) to (C).
- a method for producing a monomer corresponding to the unit (A) will be described.
- Such a monomer is represented, for example, by the following general formula (2).
- R 1 is a hydrogen atom
- R 2 and R 3 are each independently a hydrogen atom or CH 3
- X is a hydrogen atom or carbon It is a hydrocarbon group which may contain a hydroxyl group of several 4 or less.
- R 1 is preferably a hydrogen atom or CH 3
- R 2 and R 3 are preferably a hydrogen atom.
- the hydrocarbon group include, but are not limited to, a methyl group, an ethyl group, a propyl group, a butyl group, a vinyl group, a 2-hydroxyethyl group, and a 4-hydroxybutyl group.
- the compound represented by the general formula (2) in this embodiment can be synthesized by using, for example, the route represented by the following formula (I) using dicyclopentadiene or cyclopentadiene and an olefin having a functional group as a raw material. .
- R 1 is a hydrogen atom, CH 3 or C 2 H 5 , R 2 and R 3 are each independently a hydrogen atom or CH 3 , and X is a hydrogen atom or a carbon number of 4 or less. Which may contain a hydroxyl group of
- the monoolefin having 13 to 21 carbon atoms represented by the general formula (4) can be produced, for example, by performing a Diels-Alder reaction between an olefin having a functional group and dicyclopentadiene.
- olefin having a functional group used in the Diels-Alder reaction include, but are not limited to, methacrylic acid, methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, vinyl methacrylate, methacrylic acid-2 -Hydroxyethyl, 4-hydroxybutyl methacrylate, acrylic acid, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, vinyl acrylate, 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate Crotonic acid, methyl crotonic acid, ethyl crotonic acid, 3-methylcrotonic acid, methyl 3-methylcrotonate, ethyl 3-methylcrotonate and the like.
- Preferred olefins include methacrylic acid, methyl methacrylate, methacrylate.
- Acid-2-hydroxyethyl, acrylic acid, methyl acrylate, include 2-hydroxyethyl acrylate, methyl methacrylate, methyl acrylate may be mentioned as preferred olefin.
- examples of the olefin having a functional group used for the Diels-Alder reaction include acrylonitrile, methacrylonitrile, acrolein, and methacrolein.
- monoolefins represented by the general formula (4 ') can be produced through the routes shown in the following formulas (II) and (III).
- R 1 is a hydrogen atom or CH 3 )
- R 1 is a hydrogen atom or CH 3 )
- the dicyclopentadiene used for the Diels-Alder reaction preferably has a high purity, and it is preferable to reduce the content of butadiene, isoprene and the like.
- the purity of dicyclopentadiene is preferably 90% or more, and more preferably 95% or more. Further, since dicyclopentadiene tends to depolymerize under heating conditions to form cyclopentadiene (so-called monocyclopentadiene), it is also possible to use cyclopentadiene instead of dicyclopentadiene.
- the monoolefin having 13 to 21 carbon atoms represented by the general formula (4) is substantially a monoolefin having 8 to 16 carbon atoms represented by the following general formula (7) (the first stage Diels-Alder reaction product).
- Dienophile Dienophile
- the second stage Diels-Alder reaction is considered to produce a monoolefin having 13 to 21 carbon atoms represented by the general formula (4).
- the monoolefin having 13 to 21 carbon atoms represented by the formula (4) is appropriately controlled by appropriately controlling the reaction conditions of the first stage Diels-Alder reaction.
- a monoolefin having 8 to 16 carbon atoms represented by the formula (7) can be selectively obtained.
- R 1 represents a hydrogen atom, CH 3 or C 2 H 5
- R 2 and R 3 each independently represent a hydrogen atom or CH 3
- X represents a hydrogen atom or a carbon number of 4 or less.
- the reaction temperature is preferably 100 ° C. or higher, more preferably 120 ° C. or higher, and further preferably 130 ° C. or higher.
- the reaction temperature is preferably less than 180 ° C. In any case, it is preferable to perform the reaction at a temperature of 250 ° C. or lower in order to suppress the by-product of the high boiling substance.
- reaction solvents such as aliphatic hydrocarbons having 6 or more carbon atoms, cyclohexane, toluene, xylene, ethylbenzene, mesitylene, propanol, butanol, etc. preferable. If necessary, it may be added to AlCl 3 or the like known catalysts.
- R 1 is a hydrogen atom
- R 2 and R 3 are each independently a hydrogen atom or CH 3
- X is a hydrogen atom or carbon (It is a hydrocarbon group which may contain a hydroxyl group of several 4 or less.)
- the reaction method of the Diels-Alder reaction is a batch system using a tank reactor, a semi-batch system in which a substrate or a substrate solution is supplied to a tank reactor under reaction conditions, and a substrate type under a reaction condition in a tube reactor. It is possible to adopt various reaction methods such as a continuous flow method for distributing the gas.
- the reaction product obtained by the Diels-Alder reaction can be used as a raw material for the next hydroformylation reaction as it is, but may be used for the next step after being purified by a method such as distillation, extraction or crystallization.
- bifunctional compound having 14 to 22 carbon atoms represented by (3) in formula (I) is, for example, a monoolefin having 13 to 21 carbon atoms represented by the general formula (4) and carbon monoxide.
- hydrogen gas can be produced by a hydroformylation reaction in the presence of a rhodium compound or an organophosphorus compound.
- the rhodium compound used in the hydroformylation reaction may be a compound that forms a complex with an organic phosphorus compound and exhibits hydroformylation activity in the presence of carbon monoxide and hydrogen, and the form of the precursor is not particularly limited. .
- rhodium acetylacetonate dicarbonyl hereinafter referred to as Rh (acac) (CO) 2
- Rh 2 O 3 Rh 4 (CO) 12
- Rh 6 (CO) 16 Rh (NO 3 ) 3, etc.
- the catalyst precursor may be introduced into the reaction mixture together with the organophosphorus compound to form a rhodium metal hydridocarbonyl phosphorus complex having catalytic activity in the reaction vessel.
- a rhodium metal hydridocarbonyl phosphorus complex may be prepared in advance. It may be introduced into the reactor.
- Rh (acac) (CO) 2 is reacted with an organophosphorus compound in the presence of a solvent, and then introduced into a reactor together with an excess organophosphorus compound, and a rhodium-organophosphorus complex having catalytic activity and The method of doing is mentioned.
- a two-stage Diels-Alder reaction product having an internal olefin having a relatively large molecular weight represented by the general formula (4) is hydroformylated with a very small amount of rhodium catalyst.
- the amount of rhodium compound used in this hydroformylation reaction is preferably 0.1 to 60 micromoles per 1 mol of a monoolefin having 13 to 21 carbon atoms represented by the general formula (4) which is a substrate for the hydroformylation reaction. 0.1 to 30 ⁇ mol is more preferable, 0.2 to 20 ⁇ mol is further preferable, and 0.5 to 10 ⁇ mol is particularly preferable.
- the amount of the rhodium compound used is less than 60 micromoles per 1 mol of the monoolefin having 13 to 21 carbon atoms, it can be evaluated that it is practically not necessary to provide a collection and recycling facility for the rhodium complex. Thus, according to this embodiment, it is possible to reduce the economic burden related to the recovery and recycling equipment, and to reduce the cost for the rhodium catalyst.
- the organophosphorus compound that forms a catalyst for the hydroformylation reaction with the rhodium compound is not particularly limited.
- R a , R b , and R c include, but are not limited to, an aryl group that can be substituted with an alkyl group having 1 to 4 carbon atoms or an alkoxy group, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group.
- alicyclic alkyl groups that can be substituted with triphenylphosphine and triphenylphosphite are preferably used.
- the amount of the organophosphorus compound used is preferably 300-fold to 10,000-fold mol, more preferably 500-fold to 10,000-fold mol, still more preferably 700-fold to 5000-fold mol, particularly preferably relative to the rhodium atom in the rhodium compound. Is 900 times to 2000 times mol.
- the amount of the organic phosphorus compound used is 300 times mol or more of the rhodium atom, the stability of the rhodium metal hydridocarbonyl phosphorus complex as the catalyst active material tends to be sufficiently secured, and as a result, good reactivity is ensured. Tend to. Moreover, when the usage-amount of an organic phosphorus compound is 10000 times mole or less of a rhodium atom, it is preferable from a viewpoint of fully reducing the cost concerning an organic phosphorus compound.
- the hydroformylation reaction can be carried out without using a solvent, but can be carried out more suitably by using a solvent inert to the reaction.
- Solvents that can be used in the hydroformylation reaction include those that dissolve the monoolefin having 13 to 21 carbon atoms, dicyclopentadiene or cyclopentadiene represented by the general formula (4), the rhodium compound, and the organophosphorus compound. If it does not specifically limit.
- hydrocarbons such as aliphatic hydrocarbons, alicyclic hydrocarbons, and aromatic hydrocarbons
- esters such as aliphatic esters, alicyclic esters, and aromatic esters
- Alcohols such as aromatic alcohols and alicyclic alcohols
- solvents such as aromatic halides.
- hydrocarbons are preferably used, and alicyclic hydrocarbons and aromatic hydrocarbons are more preferably used.
- the temperature for the hydroformylation reaction is preferably 40 ° C. to 160 ° C., more preferably 80 ° C. to 140 ° C.
- the reaction temperature is 40 ° C. or higher, a sufficient reaction rate tends to be obtained, and the residual monoolefin as a raw material tends to be further suppressed.
- the reaction is performed under pressure with carbon monoxide (hereinafter also referred to as “CO”) and hydrogen (hereinafter also referred to as “H 2” ) gas.
- CO carbon monoxide
- H 2 hydrogen
- the CO and H 2 gases can be independently introduced into the reaction system, or can be introduced into the reaction system as a mixed gas prepared in advance.
- the molar ratio of CO and H 2 gas introduced into the reaction system is preferably 0.2 to 5, more preferably 0.5 to 2, and still more preferably 0.8 to 1.2. .
- the reaction activity of the hydroformylation reaction and the selectivity of the target aldehyde tend to be good. Since CO and H 2 gas introduced into the reaction system decrease with the progress of the reaction, the reaction control may be simple when a previously prepared mixed gas of CO and H 2 is used.
- the reaction pressure of the hydroformylation reaction is preferably 1 to 12 MPa, more preferably 1.2 to 9 MPa, and further preferably 1.5 to 5 MPa.
- the reaction pressure is 1 MPa or more, a sufficient reaction rate tends to be obtained, and the residual monoolefin as a raw material tends to be sufficiently suppressed.
- the reaction pressure is set to 12 MPa or less, it is economically advantageous because expensive equipment excellent in pressure resistance is not required.
- a batch reaction or a semi-batch reaction is suitable as a reaction system in the case of performing the hydroformylation reaction.
- the semi-batch reaction is performed by adding a rhodium compound, an organic phosphorus compound, and the above solvent to the reactor, pressurizing or heating with CO / H 2 gas, etc. This can be done by feeding the solution to the reactor.
- the reaction product obtained by the hydroformylation reaction can be used as a raw material for the next reduction reaction as it is, but may be subjected to the next step after purification by distillation, extraction, crystallization, or the like.
- the compound having 14 to 22 carbon atoms represented by the general formula (2) in the formula (I) is obtained by converting a compound having 14 to 22 carbon atoms represented by the general formula (3) into a catalyst having hydrogenation ability and It can be produced by reduction in the presence of hydrogen.
- a catalyst containing at least one element selected from the group consisting of copper, chromium, iron, zinc, aluminum, nickel, cobalt, and palladium as a catalyst having hydrogenation ability. More preferred catalysts include a Cu—Cr catalyst, a Cu—Zn catalyst, a Cu—Zn—Al catalyst, and the like, as well as a Raney-Ni catalyst, a Raney-Co catalyst, and the like. Further preferred catalysts include a Cu—Cr catalyst and a Raney catalyst. -Co catalyst.
- the amount of the hydrogenation catalyst used is 1 to 100% by mass, preferably 2 to 50% by mass, more preferably 5 to 5% by mass with respect to the compound having 14 to 22 carbon atoms represented by the general formula (3) as a substrate. 30% by mass.
- the amount of catalyst used is 1% by mass or more, the reaction proceeds sufficiently, and as a result, the yield of the target product tends to be sufficiently secured. Further, when the amount of catalyst used is 100% by mass or less, the balance between the amount of catalyst used for the reaction and the effect of improving the reaction rate tends to be good.
- the reaction temperature for the reduction reaction is preferably 60 to 200 ° C, more preferably 80 to 150 ° C.
- the reaction temperature for the reduction reaction is preferably 60 to 200 ° C, more preferably 80 to 150 ° C.
- the reaction temperature By setting the reaction temperature to 200 ° C. or lower, the occurrence of side reactions and decomposition reactions is suppressed, and the target product tends to be obtained with a high yield.
- the reaction temperature by setting the reaction temperature to 60 ° C. or higher, the reaction can be completed in an appropriate time, and there is a tendency that a decrease in productivity and a decrease in the yield of the target product can be avoided.
- the reaction pressure of the reduction reaction is preferably 0.5 to 10 MPa, more preferably 1 to 5 MPa as a hydrogen partial pressure.
- the hydrogen partial pressure is preferably 0.5 to 10 MPa or less, the occurrence of side reactions and decomposition reactions is suppressed, and the target product tends to be obtained in a high yield.
- the hydrogen partial pressure is set to 0.5 MPa or more, the reaction can be completed in an appropriate time, and a decrease in productivity and a decrease in the yield of the target product tend to be avoided.
- a gas inert to the reduction reaction for example, nitrogen or argon
- a solvent can be used.
- the solvent used for the reduction reaction include aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, alcohols, and the like. Among them, alicyclic hydrocarbons, aromatic hydrocarbons, alcohols, etc. Are preferred. Specific examples thereof include cyclohexane, toluene, xylene, methanol, ethanol, 1-propanol and the like.
- the reaction method of the reduction reaction is a batch type using a tank reactor, a semi-batch type for supplying a substrate or a substrate solution to a tank reactor under the reaction conditions, a reaction condition in a tube type reactor filled with a molded catalyst. It is possible to adopt various reaction methods such as a continuous flow method in which a substrate and a substrate solution are circulated.
- the reaction product obtained by the reduction reaction can be purified by, for example, distillation, extraction, crystallization, or the like.
- the compound represented by the general formula (2) or the compound represented by the formula (8) is a monomer corresponding to the unit (A), and each unit corresponding to the units (B) to (C) is used.
- the method of copolymerizing with the monomer is not particularly limited, and a conventionally known polyester production method can be applied. Examples thereof include a melt polymerization method such as a transesterification method and a direct esterification method, or a solution polymerization method.
- a transesterification catalyst, an esterification catalyst, a polycondensation catalyst, or the like used in the production of a normal polyester resin can be used.
- These catalysts are not particularly limited.
- metals such as zinc, lead, cerium, cadmium, manganese, cobalt, lithium, sodium, potassium, calcium, nickel, magnesium, vanadium, aluminum, titanium, antimony, germanium, tin, etc.
- fatty acid salts, carbonates, phosphates, hydroxides, chlorides, oxides, alkoxides can be used alone or in combination of two or more.
- the catalyst compounds of manganese, cobalt, zinc, titanium, calcium, antimony, germanium, and tin are preferable, and compounds of manganese, titanium, antimony, germanium, and tin are more preferable.
- the amount of these catalysts to be used is not particularly limited, but the amount as a metal component with respect to the raw material of the polyester resin is preferably 1 to 1000 ppm, more preferably 3 to 750 ppm, and still more preferably 5 to 500 ppm.
- the reaction temperature in the polymerization reaction depends on the type of catalyst and the amount of the catalyst used, but is usually selected within the range of 150 ° C. to 300 ° C., preferably 180 ° C. to 280 ° C. in consideration of the reaction rate and resin coloring.
- the pressure in the reaction layer is preferably adjusted to 1 kPa or less finally from the atmospheric atmosphere, and more preferably 0.5 kPa or less.
- a phosphorus compound When performing the polymerization reaction, a phosphorus compound may be added if desired.
- the phosphorus compound include, but are not limited to, phosphoric acid, phosphorous acid, phosphoric acid ester, phosphorous acid ester, and the like.
- phosphate esters include, but are not limited to, methyl phosphate, ethyl phosphate, butyl phosphate, phenyl phosphate, dimethyl phosphate, diethyl phosphate, dibutyl phosphate, diphenyl phosphate, trimethyl phosphate, Examples thereof include triethyl phosphate, tributyl phosphate, and triphenyl phosphate.
- phosphites include, but are not limited to, methyl phosphite, ethyl phosphite, butyl phosphite, phenyl phosphite, dimethyl phosphite, diethyl phosphite, dibutyl phosphite, Examples thereof include diphenyl phosphite, trimethyl phosphite, triethyl phosphite, tributyl phosphite, and triphenyl phosphite. These can be used alone or in combination of two or more.
- the concentration of phosphorus atoms in the copolyester resin of this embodiment is preferably 1 to 500 ppm, more preferably 5 to 400 ppm, and even more preferably 10 to 200 ppm.
- various stabilizers such as an etherification inhibitor, a heat stabilizer, and a light stabilizer, a polymerization regulator, and the like can be used.
- the polyester resin composition of this embodiment contains an antioxidant.
- Antioxidant means an additive blended in the resin for the purpose of preventing oxidative deterioration and yellowing due to heat, and preferred examples include phenol-based antioxidants and phosphorus-based antioxidants.
- Phenol antioxidants and phosphorus antioxidants are each preferably used alone, but when used in combination, the phosphorus antioxidants supplement the peroxide generated by the function of the phenolic antioxidants. It tends to prevent yellowing. Therefore, it is more preferable to use a phenol-based antioxidant and a phosphorus-based antioxidant in combination. That is, it is preferable that the antioxidant in the present embodiment includes a phenol-based antioxidant and / or a phosphorus-based antioxidant.
- the phenolic antioxidant is not particularly limited, and examples thereof include 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol, and 2,6-di-tert.
- 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1,3,5-triazine-2,4,6 (1H , 3H, 5H) -trione, 4,4 ′, 4 ′′-(1-methylpropanyl-3-ylidene) tris (6-tert-butyl-m-cresol), n-octadecyl-3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 3,9-bis (2- (3 -(3-tert-butyl-4-hydroxy-5-methylphenyl) -propionyloxy) -1,1-dimethylethyl) -2,4,8,10-tetraoxaspiro [5.
- Undecane is preferred, and 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H)- Trion is particularly preferred.
- phenolic antioxidants may be used alone or in combination of two or more phenolic antioxidants.
- the phosphorus-based antioxidant is not particularly limited.
- triphenyl phosphite tris (methylphenyl) phosphite, triisooctyl phosphite, tridecyl phosphite, tris (2-ethylhexyl) phosphite 2-ethylhexyl diphenyl phosphite, tris (nonylphenyl) phosphite, tris (octylphenyl) phosphite, tris [decyl poly (oxyethylene) phosphite, tris (cyclohexylphenyl) phosphite, tricyclohexyl phosphite, tri (decyl) ) Thiophosphite, triisodecyl thiophosphite, phenyl bis (2-ethylhexyl) phosphite, pheny
- the above-mentioned phosphorus antioxidants may be used alone or in combination with two or more phosphorus antioxidants.
- 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) is used as a phenolic antioxidant from the viewpoint of more effectively preventing yellowing in a high temperature environment.
- -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione and / or pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate
- 3,9-bis (2,6-di-tert-butyl-4-methylphenoxy) -2,4,8,10-tetraoxa-3,9-diphosphaspiro as a phosphorus-based antioxidant [5.5]
- it includes undecane and / or tris (2,4-di-tert-butylphenyl) phosphite.
- antioxidant in the present embodiment, a lactone antioxidant, a sulfur antioxidant, and other known antioxidants can be used in addition to those described above.
- the lactone antioxidant is not particularly limited, but 5,7-di-tert-butyl-3- (3,4-di-methylphenyl) -3H-bezofuran-2-one is preferable.
- the sulfur-based antioxidant is not particularly limited, but 2,2-bis ⁇ [3- (dodecylthio) -1-oxypropoxy] methyl ⁇ propane-1,3-diylbis [3- (dodecylthio) propionate], di- (Tridecyl) 3,3′-thiodipropionate is preferred.
- the content of the antioxidant used in this embodiment is preferably 0.005 to 1 part by mass, more preferably 0.007 to 0.8 part by mass with respect to the polyester resin used in this embodiment. More preferably, it is 0.01 to 0.7 parts by mass.
- the content is 0.005 parts by mass or more, there is a tendency that deterioration of the polyester resin (yellowing, generation of gel component, molecular weight reduction, etc.) can be preferably prevented during polymerization or heat processing during molding. There is a tendency to ensure sufficient heat-resistant yellowing.
- it is 1 mass part or less it exists in the tendency which can prevent problems, such as a bleed out to the metal mold
- the content of the phenolic antioxidant is preferably 0.005 to 1 part by mass, more preferably 0.007 to 0.8 part by mass with respect to 100 parts by mass of the polyester resin. More preferably 0.01 to 0.7 parts by mass.
- the content of the phosphorus-based antioxidant is preferably 0.005 to 1 part by weight, more preferably 0.007 to 0.8 part by weight, based on 100 parts by weight of the polyester resin. The amount is preferably 0.01 to 0.7 parts by mass.
- the polyester resin composition of this embodiment may contain one or more ultraviolet absorbers.
- an ultraviolet absorber for example, inorganic type ultraviolet absorbers, such as a cerium oxide and a zinc oxide; A benzotriazole type compound, a benzophenone type compound, a salicylate type compound, a cyanoacrylate type compound, a triazine type compound, an oxanilide type
- organic ultraviolet absorbers such as compounds, malonic acid ester compounds, hindered amine compounds, oxalic acid anilide compounds, and benzoxazinone compounds.
- an organic ultraviolet absorber is preferable, a benzotriazole compound, a triazine compound, or a benzoxazinone compound is more preferable, and a benzotriazole compound (a compound having a benzotriazole structure) is used. It is particularly preferred.
- benzotriazole compound examples include, for example, 2- (2′-hydroxy-5′-methylphenyl) benzotriazole, 2- [2′-hydroxy-3 ′, 5′-bis ( ⁇ , ⁇ -dimethyl).
- Benzyl) phenyl] -benzotriazole 2- (2′-hydroxy-3 ′, 5′-di-tert-butyl-phenyl) -benzotriazole, 2- (2′-hydroxy-3′-tert-butyl-5) '-Methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-3', 5'-di-tert-butyl-phenyl) -5-chlorobenzotriazole), 2- (2'-hydroxy- 3 ′, 5′-di-tert-amyl) -benzotriazole, 2- (2′-hydroxy-5′-tert-octylphenyl) benzotriazol 2,2′-methylenebis [6- (benzo)
- benzophenone compounds include, for example, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, 2-hydroxy-4-n-octate.
- salicylate compound examples include, but are not limited to, phenyl salicylate, 4-tert-butylphenyl salicylate, and the like.
- cyanoacrylate compound examples include, but are not limited to, ethyl-2-cyano-3,3-diphenyl acrylate, 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate, and the like.
- oxanilide compound examples include, but are not limited to, 2-ethoxy-2'-ethyloxalinic acid bis-arinide and the like.
- the malonic acid ester compound is not particularly limited, but 2- (alkylidene) malonic acid esters are preferable, and 2- (1-arylalkylidene) malonic acid esters are more preferable.
- triazine-based compound examples include, but are not limited to, 2,4-bis [2-hydroxy-4-butoxyphenyl] -6- (2,4-dibutoxyphenyl) -1,3,5-triazine 2- (2-hydroxy-4- [1-octyloxycarbonylethoxy] phenyl) -4,6-bis (4-phenylphenyl) -1,3,5-triazine, 2- (4,6-diphenyl- 1,3,5-triazin-2-yl) -5- [2- (2-ethylhexanoyloxy) ethoxy] -phenol, 2- [4,6-bis (2,4-dimethylphenyl) -1, 3,5-triazin-2-yl] -5- (octyloxy) phenol, 2- (4,6-diphenyl-1,3,5-triazin-2-yl) -5-[(hexyl) oxy]- Phenol, 2, 6- tris (2-hydroxy-4-butoxy
- the content of the ultraviolet absorber component that can be used can be 0.005 to 1 part by mass, preferably 0.007 to 0.8 part by mass with respect to the polyester resin in the present embodiment. More preferably, it is 0.01 to 0.7 parts by mass.
- the content is 0.005 parts by mass or more, sufficient weather resistance tends to be ensured, and when it is 1 part by mass or less, problems such as bleeding out to the mold during molding tend to be preferably prevented. It is in.
- various known ultraviolet absorbers may be used in combination as long as the effects of the present embodiment are not impaired.
- the polyester resin composition of the present embodiment includes a light stabilizer, a plasticizer, an extender, a matting agent, a drying regulator, an antistatic agent, and an antisettling agent as long as the purpose of the present embodiment is not impaired.
- Various additives such as additives, surfactants, flow improvers, drying oils, waxes, colorants, dispersants, reinforcing agents, surface smoothing agents, leveling agents, curing reaction accelerators, thickeners, and molding aids. Can be added. These can use various well-known things and can add it to a resin composition individually by 1 type or in combination of 2 or more types.
- additive any additive that can be used in the present embodiment
- a method in which a polymerization reaction is performed and contained in the presence of an additive or a method in which an additive is added to a polyester resin in a molten state before being extracted from the polymerization vessel in the polymerization step, and the additive is dried after pelletizing the polyester resin.
- a blending method or a method of adding an additive to a melted polyester resin using an extruder or the like is employed.
- a known apparatus can be used for mixing and kneading the polyester resin and the additive component.
- liquid mixing apparatuses such as a gate mixer, a butterfly mixer, a universal mixer, a dissolver, and a static mixer, can also be used.
- a resin containing a high concentration additive component and a polyester resin can be mixed by the above method and apparatus.
- the polyester resin composition of this embodiment can contain a resin other than the polyester resin in this embodiment as long as the desired effect of this embodiment is not impaired.
- a resin is not particularly limited.
- polyester resin other than the polyester resin in the present embodiment polycarbonate resin, (meth) acrylic resin, polyamide resin, polystyrene resin, acrylonitrile-butadiene-styrene copolymer resin, chloride It may further include at least one resin selected from the group consisting of vinyl resin, polyphenylene ether resin, polysulfone resin, polyacetal resin, and methyl methacrylate-styrene copolymer resin.
- These can use various well-known things and can add it to a resin composition individually by 1 type or in combination of 2 or more types. As these content, it is preferable to set it as 10 mass% or less in a resin composition.
- Resin composition The ratio of the diol structural unit and the dicarboxylic acid structural unit in the polyester resin was calculated by 1 H-NMR measurement. The measurement was performed at 400 MHz using a nuclear magnetic resonance apparatus (manufactured by JEOL Ltd., trade name: JNM-AL400). Deuterated chloroform was used as the solvent.
- the glass transition temperature of the polyester resin was measured as follows. Using a differential scanning calorimeter (manufactured by Shimadzu Corporation, trade name: DSC / TA-60WS), about 10 mg of copolymer polyester resin was placed in an aluminum non-sealed container, and in a nitrogen gas (30 mL / min) stream, A sample heated and melted to 280 ° C. at a temperature rising rate of 20 ° C./min was rapidly cooled to obtain a measurement sample. The sample was measured under the same conditions, and the temperature at which the difference between the baselines before and after the transition of the DSC curve changed by 1/2 was taken as the glass transition temperature.
- Heat-resistant yellowing is a yellowness in the thickness direction (light path length: 3 mm) before and after the test after storing a disk-shaped test piece having a thickness of 3 mm and a diameter of 50 mm in a hot air dryer at 125 ° C. for 1000 hours. Evaluation was based on the difference in YI ( ⁇ YI). The yellowness was measured in accordance with JIS K7103 using a fog value measuring apparatus (model: COH-400) manufactured by Nippon Denshoku Industries Co., Ltd. in an atmosphere of 23 ° C. and 50% relative humidity.
- Total light transmittance The total light transmittance is 3 mm in thickness and a disk-shaped test piece having a diameter of 50 mm is stored in a hot air dryer at 125 ° C. for 1000 hours, and then the thickness direction before and after the test (light path length: 3 mm).
- the total light transmittance was measured with a fog value measuring apparatus (model: COH-400) manufactured by Nippon Denshoku Industries Co., Ltd.
- Methoxycarbonyl-6 (7) -methanol 4011.13 g, ethylene glycol 811.47 g, 1,4-cyclohexanedicarboxylate dimethyl (cis / trans 7/3) 506.68 g, and manganese acetate tetrahydrate as transesterification catalyst 1.24 g of the product was charged, and the temperature was raised to 250 ° C. to conduct a transesterification reaction. After the reaction conversion rate of the dicarboxylic acid component is set to 90% or more, 2.88 g of germanium oxide and 1.65 g of phosphoric acid are added, and the temperature is increased and the pressure is gradually reduced, and finally at 280 ° C. and 0.1 kPa or less. Polycondensation was performed.
- polyester resins having a weight average molecular weight of 48000 and a glass transition temperature of 144 ° C. were produced.
- polyester resin composition To 100 parts by mass of the polyester resin, 0.1 parts by mass of calcium stearate as a release agent and the amount of antioxidants shown in Table 1 (unit: parts by mass) were dry-mixed using a tumbler, Toyo Seiki Seisakusho ( Kneading was carried out at a cylinder temperature of 260 ° C. using a Laboplast mill manufactured by Co., Ltd. The following additives were used as additives in the table.
- Antioxidant 1 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H)- Trion: “Adeka Stub AO-20” manufactured by Adeka Antioxidant 2: 4,4 ′, 4 ′′-(1-methylpropanyl-3-ylidene) tris (6-tert-butyl-m-cresol); “Adeka Stub AO-30” manufactured by Adeka Corporation, Antioxidant 3: n-octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate; “Adeka Stub AO-50” manufactured by Adeka Company, Antioxidant 4: Pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate]; “Adeka Stub AO-60” manufactured by Ade
- polyester resin compositions prepared in Examples 1 to 9 were molded into a disk having a thickness of 3 mm and a diameter of 50 mm under the conditions of a cylinder temperature of 270 ° C. and a mold temperature of 130 ° C. using a screw injection molding machine (J55AD manufactured by JSW). The measurement samples of each example were used.
- the polyester resin composition of the present invention is excellent in transparency and heat-resistant yellowing.
- a molded article excellent in transparency and heat-resistant yellowing can be produced.
- the present invention can be suitably used for lenses, lens members such as LED lighting lenses and spectacle lenses, optical members such as light guide plates and optical fibers, optical film materials such as retardation films, etc., and the industrial significance of the present invention is great.
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Abstract
Description
[1]
下記一般式(1)で表される単位(A)を含有するポリエステル樹脂と、酸化防止剤と、を含む、ポリエステル樹脂組成物。
[2]
ポリエステル樹脂が、前記単位(A)、ジオール単位(B)、及びジカルボン酸又はそのエステル形成性誘導体単位(C)を有する共重合ポリエステル樹脂であり、
前記共重合ポリエステル樹脂の全単位中の前記単位(A)の含有量が10~95mol%である、[1]に記載のポリエステル樹脂組成物。
[3]
前記酸化防止剤が、フェノール系酸化防止剤及び/又はリン系酸化防止剤を含む、[1]又は[2]に記載のポリエステル樹脂組成物。
[4]
前記フェノール系酸化防止剤が、1,3,5-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン、4,4’,4’’-(1-メチルプロパニル-3-イリデン)トリス(6-tert-ブチル-m-クレゾール)、n-オクタデシル-3-(3、5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオナート、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオナート]、及び3,9-ビス(2-(3-(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)-1,1-ジメチルエチル)-2,4,8,10-テトラオキサスピロ[5.5]ウンデカンからなる群より選択される少なくとも一種を含む、[3]に記載のポリエステル樹脂組成物。
[5]
前記リン系酸化防止剤がトリス(2,4-ジ-tert-ブチルフェニル)ホスファイト、及び3,9-ビス(2,6-ジ-tert-ブチル-4-メチルフェノキシ)-2,4,8,10-テトラオキサ-3,9-ジホスファスピロ[5.5]ウンデカンからなる群より選択される少なくとも一種を含む、[3]又は[4]に記載のポリエステル樹脂組成物。
[6]
前記フェノール系酸化防止剤として、1,3,5-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン及び/又はペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオナート]を含み、
前記リン系酸化防止剤として、3,9-ビス(2,6-ジ-tert-ブチル-4-メチルフェノキシ)-2,4,8,10-テトラオキサ-3,9-ジホスファスピロ[5.5]ウンデカン及び/又はトリス(2,4-ジ-tert-ブチルフェニル)ホスファイトを含む、[3]~[5]のいずれか1項に記載のポリエステル樹脂組成物。
[7]
前記フェノール系酸化防止剤が1,3,5-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオンである、[3]~[6]のいずれか1項に記載のポリエステル樹脂組成物。
[8]
前記リン系酸化防止剤が、3,9-ビス(2,6-ジ-tert-ブチル-4-メチルフェノキシ)-2,4,8,10-テトラオキサ-3,9-ジホスファスピロ[5.5]ウンデカンである、[3]~[7]のいずれか1項に記載のポリエステル樹脂組成物。
[9]
前記フェノール系酸化防止剤の含有量が、前記ポリエステル樹脂100質量部に対し、0.005~1質量部である、[3]~[8]のいずれか1項に記載のポリエステル樹脂組成物。
[10]
前記リン系酸化防止剤の含有量が前記ポリエステル樹脂100質量部に対し、0.005~1質量部である、[3]~[9]のいずれか1項に記載のポリエステル樹脂組成物。
本実施形態のポリエステル樹脂組成物は、下記一般式(1)で表される単位(A)を含有するポリエステル樹脂と、酸化防止剤と、を含む。このように構成されているため、本実施形態の樹脂組成物は、高温環境下における使用においても、透明性を維持できると共に黄着色による外観の悪化を防止できる。
本実施形態におけるポリエステル樹脂は、ノルボルナン環骨格に由来して、耐熱性や透明性等の各種物性に優れる傾向にあるが、かかる物性と、酸化防止剤が有する黄着色防止効果とが相俟って、本実施形態の所望とする効果を得ることができる。すなわち、本実施形態の樹脂組成物は、COP等の公知のポリマーと酸化防止剤とを組み合わせる場合に比べ、高温環境下での使用における黄着色防止効果を顕著に高めることができ、透明性も維持できる。
本実施形態におけるポリエステル樹脂は、上記一般式(1)で表される単位(A)(以下、「単位(A)」ともいう。)を有する限り特に限定されないが、当該ポリエステル樹脂は、単位(A)、ジオール単位(B)(以下、「単位(B)」ともいう。)、及びジカルボン酸又はそのエステル形成性誘導体単位(C)(以下、「単位(C)」ともいう。)を有する共重合ポリエステル樹脂(以下、単に「共重合ポリエステル樹脂」ともいう。)であって、前記共重合ポリエステル樹脂が有する全単位中、前記単位(A)の含有量が10~95mol%であることが好ましい。
また、上記一般式(1)中のnは、耐熱性をより向上させる観点から、1であることが好ましい。
構成単位(B)は、良好な透明性が得られることから、脂肪族ジオール又はカルド構造を有するジオールに由来する単位であることが好ましい。このような脂肪族ジオールに由来する単位としては、1,4-シクロヘキサンジメタノール、エチレングリコール、トリシクロデカンジメタノール、3,9-ビス(1,1-ジメチル-2-ヒドロキシエチル)-2,4,8,10-テトラオキサスピロ[5.5]ウンデカン、1,4:3,6-ジアンヒドロ-D-ソルビトール、2,2,4,4-テトラメチル-1,3-シクロブタンジオールに由来する単位がより好ましい。また、カルド構造を有するジオールに由来する単位としては、9,9-ビス[4-(2-ヒドロキシエトキシ)フェニル]フルオレン、9,9-ビス[4-(2-ヒドロキシエトキシ)-3-メチルフェニル]フルオレン、9,9-ビス[4-(2-ヒドロキシエトキシ)-3-フェニルフェニル]フルオレンに由来する単位がより好ましい。
なお、これらの光学異性体は、シス体、トランス体、これらの混合物のいずれであってもよく、特に限定されない。
共重合ポリエステル樹脂が有する全単位に対する単位(B)の含有量は、2.5~45mol%であることが好ましく、より好ましくは2.5~40mol%である。
上記した単位は、1種を単独で含まれていてもよく、2種以上を組み合わせて含まれていてもよい。
構成単位(C)は、良好な透明性が得られることから、脂肪族ジカルボン酸又はそのエステル形成性誘導体、若しくはカルド構造を有するジカルボン酸又はそのエステル形成性誘導体に由来する単位であることが好ましい。脂肪族ジカルボン酸又はそのエステル形成性誘導体に由来する単位としては、透明性及び耐熱性の物性バランスの観点から、1,4-シクロヘキサンジカルボン酸ジメチルに由来する単位がより好ましい。また、カルド構造を有するジカルボン酸又はそのエステル形成性誘導体に由来する単位としては、透明性及び耐熱性の物性バランスの観点から、9,9-ビス(メトキシカルボニルメチル)フルオレン、9,9-ビス(メトキシカルボニルエチル)フルオレン、9,9-ビス(メトキシカルボニルプロピル)フルオレンに由来する単位がより好ましい。
なお、これらの光学異性体は、シス体、トランス体、これらの混合物のいずれであってもよく、特に限定されない。
共重合ポリエステル樹脂が有する全単位に対する単位(C)の含有量は、2.5~45mol%であることが好ましく、より好ましくは2.5~40mol%である。
上記した単位は、1種を単独で含まれていてもよく、2種以上を組み合わせて含まれていてもよい。
本実施形態における共重合ポリエステル樹脂は、単位(A)~(C)に対応する各単量体を共重合することにより、得ることができる。以下、単位(A)に対応する単量体の製造方法について説明する。かかる単量体は、例えば、下記一般式(2)で表される。
式(2)において、R1は、好ましくは水素原子又はCH3である。R2及びR3は、好ましくは水素原子である。上記炭化水素基としては、以下に限定されないが、例えば、メチル基、エチル基、プロピル基、ブチル基、ビニル基、2-ヒドロキシエチル基、4-ヒドロキシブチル基等が挙げられる。
前記一般式(4)で表される炭素数13~21のモノオレフィンは、例えば、官能基を有するオレフィンとジシクロペンタジエンのディールスアルダー反応を行うこと等で製造することが可能である。
以上の観点から、例えば、上記式(I)に示す反応ルートにおいて、1段目ディールスアルダー反応の反応条件を適宜制御することにより、式(4)で表される炭素数13~21のモノオレフィンあるいは式(7)で表される炭素数8~16のモノオレフィンを選択的に得ることができる。
上記のようにして得られた式(4)で表される炭素数13~21のモノオレフィンを、後述するヒドロホルミル化反応及び還元反応に供することで、式(1)においてn=1である場合に対応する単量体(すなわち、式(2)で表される化合物)を得ることができる。また、上記のようにして得られた式(7)で表される炭素数8~16のモノオレフィンを、同様のヒドロホルミル化反応及び還元反応に供することで、式(1)においてn=0である場合に対応する単量体(すなわち、式(8)で表される化合物)を得ることができる。
なお、反応溶媒として炭化水素類やアルコール類、エステル類等を使用することも可能であり、炭素数6以上の脂肪族炭化水素類、シクロヘキサン、トルエン、キシレン、エチルベンゼン、メシチレン、プロパノール、ブタノール等が好ましい。また、必要に応じて、AlCl3等公知の触媒を添加してもよい。
前記式(I)中の一般式(3)で表される炭素数14~22の二官能性化合物は、例えば、一般式(4)で表される炭素数13~21モノオレフィンと一酸化炭素及び水素ガスをロジウム化合物、有機リン化合物の存在下でヒドロホルミル化反応させること等で製造することができる。
前記式(I)中の一般式(2)で表される炭素数14~22の化合物は、一般式(3)で表される炭素数14~22の化合物を、水素化能を有する触媒及び水素の存在下で還元することにより製造することが出来る。
)ホスフェート、2-ヒドロキシプロピルジ(オキシプロピレン)ホスフェート、2-ヒドロキシプロピルポリ(オキシプロピレン)ホスフェート及びオクタデシルポリ(オキシエチレン)ホスフェート、ジ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、ジベンジルホスフェート、トリエチルホスフェート、トリメチルホスフェート、トリオクチルホスフェート、トリクレジルホスフェート、トリス(4-tert-ブチルフェニル)ホスフェート、トリス(ブトキシエチル)ホスフェート、トリ-n-ブチルホスフェートなどのリン酸およびそのエステル類並びにこれらのリチウム、ナトリウム、カリウム、マグネシウム、カルシウム、バリウム、亜鉛及びアルミニウム金属塩化合物;次亜リン酸、ポリリン酸等が挙げられる。
上記同様の観点から、フェノール系酸化防止剤の含有量は、ポリエステル樹脂100質量部に対し、0.005~1質量部であることが好ましく、より好ましくは0.007~0.8質量部であり、さらに好ましくは0.01~0.7質量部である。同様に、リン系酸化防止剤の含有量は、ポリエステル樹脂100質量部に対し、0.005~1質量部であることが好ましく、より好ましくは0.007~0.8質量部であり、さらに好ましくは0.01~0.7質量部である。
紫外線吸収剤としては、特に限定されないが、例えば、酸化セリウム、酸化亜鉛などの無機系紫外線吸収剤;ベンゾトリアゾール系化合物、ベンゾフェノン系化合物、サリシレート系化合物、シアノアクリレート系化合物、トリアジン系化合物、オギザニリド系化合物、マロン酸エステル化合物、ヒンダードアミン系化合物、シュウ酸アニリド系化合物、ベンゾオキサジノン系化合物などの有機系紫外線吸収剤が挙げられる。これらの中で、有機系紫外線吸収剤であることが好ましく、ベンゾトリアゾール系化合物、トリアジン系化合物又はベンゾオキサジノン系化合物であることがより好ましく、ベンゾトリアゾール系化合物(ベンゾトリアゾール構造を有する化合物)であることが特に好ましい。
ポリエステル樹脂中のジオール構成単位及びジカルボン酸構成単位の割合は、1H-NMR測定にて算出した。測定装置は、核磁気共鳴装置(日本電子(株)製、商品名:JNM-AL400)を用い、400MHzで測定した。溶媒には重クロロホルムを用いた。
ポリエステル樹脂濃度が0.2質量%になるようにテトラヒドロフランに溶解させ、ゲルパーミエイションクロマトグラフィー(GPC)で測定し、標準ポリスチレンで検量した。GPCは東ソー株式会社製カラムTSKgel SuperHM-Mを用い、カラム温度40℃で測定した。溶離液はテトラヒドロフランを0.6ml/minの流速で流し、RI検出器で測定した。
ポリエステル樹脂のガラス転移温度は、次のように測定した。示差走査熱量計((株)島津製作所製、商品名:DSC/TA-60WS)を使用し、共重合ポリエステル樹脂約10mgをアルミニウム製非密封容器に入れ、窒素ガス(30mL/分)気流中、昇温速度20℃/分で280℃まで加熱、溶融したものを急冷して測定用試料とした。該試料を同条件で測定し、DSC曲線の転移前後における基線の差の1/2だけ変化した温度をガラス転移温度とした。
耐熱黄変性は厚さ3mm、直径50mmの円盤型の試験片を125℃の熱風乾燥機中にて1000時間保存後、試験前後の厚み方向(光路長3mm)の黄色度YIの差(ΔYI)にて評価した。なお、黄色度の測定はJIS K7103に準じ、23℃、相対湿度50%の雰囲気下で日本電色工業株式会社製の曇価測定装置(型式:COH-400)にて行った。
全光線透過率は厚さ3mm、直径50mmの円盤型の試験片を125℃の熱風乾燥機中にて1000時間保存後、試験前後の厚み方向(光路長3mm)の全光線透過率を日本電色工業株式会社製の曇価測定装置(型式:COH-400)にて測定した。
〔ポリエステル樹脂の製造〕
分縮器、全縮器、コールドトラップ、撹拌機、加熱装置、窒素導入管を備えた10Lのポリエステル製造装置に、原料モノマーであるデカヒドロ-1、4:5、8-ジメタノナフタレン-2-メトキシカルボニル-6(7)-メタノール4011.93g、エチレングリコール811.47g、1,4-シクロヘキサンジカルボン酸ジメチル(シス/トランス=7/3)506.68g、及びエステル交換触媒として酢酸マンガン四水和物を1.24g仕込み、250℃まで昇温してエステル交換反応を行った。ジカルボン酸成分の反応転化率を90%以上とした後、酸化ゲルマニウム2.88g、及びリン酸1.65gを加え、昇温と減圧を徐々に行い、最終的に280℃、0.1kPa以下で重縮合を行った。適度な溶融粘度になった時点で反応を終了し、重量平均分子量48000、ガラス転移温度144℃のポリエステル樹脂をそれぞれ製造した。製造したポリエステル樹脂中のジオール構成単位及びジカルボン酸構成単位の割合は、デカヒドロ-1、4:5、8-ジメタノナフタレン-2-メトキシカルボニル-6(7)-メタノール、エチレングリコール、1,4-シクロヘキサンジカルボン酸ジメチル(シス/トランス=7/3)それぞれ、76mol%、12mol%、12mol%となった。
ポリエステル樹脂100質量部に対し、表1に記載の量(単位は質量部)の酸化防止剤、及び離型剤としてステアリン酸カルシウム0.1質量部をタンブラーを用いて乾式混合し、東洋精機製作所(株)製ラボプラストミルを用い、シリンダー温度260℃にて混練した。
尚、表中の添加剤として次のものを用いた。
酸化防止剤1:1,3,5-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン;アデカ社製「アデカスタブAO-20」
酸化防止剤2:4,4’,4’’-(1-メチルプロパニル-3-イリデン)トリス(6-tert-ブチル-m-クレゾール);アデカ社製「アデカスタブAO-30」、
酸化防止剤3:n-オクタデシル-3-(3、5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオナート;アデカ社製「アデカスタブAO-50」、
酸化防止剤4:ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオナート];アデカ社製「アデカスタブAO-60」、
酸化防止剤5:3,9-ビス(2-(3-(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)-1,1-ジメチルエチル)-2,4,8,10-テトラオキサスピロ[5.5]ウンデカン;アデカ社製「アデカスタブAO-80」、
酸化防止剤6:3,9-ビス(2,6-ジ-tert-ブチル-4-メチルフェノキシ)-2,4,8,10-テトラオキサ-3,9-ジホスファスピロ[5.5]ウンデカン;アデカ社製「アデカスタブPEP-36」、
酸化防止剤7:トリス(2,4-ジ-tert-ブチルフェニル)ホスファイト;アデカ社製「アデカスタブ2112」
実施例1~9で調製したポリエステル樹脂組成物をスクリュー式射出成型機(JSW社製J55AD)を用い、シリンダー温度270℃、金型温度130℃の条件で3mm厚、直径50mmの円盤に成形し、各例の測定試料とした。
表1に示すとおり、酸化防止剤を添加しなかったこと以外は実施例1と同様にしてポリエステル樹脂組成物の製造、試験片の作製を行い、比較例1の測定試料とした。
実施例1のポリエステル樹脂の代わりに、日本ゼオン社製COP、ZEONEX F52Rを準備し、酸化防止剤を添加せず、スクリュー式射出成型機(JSW社製J55AD)を用い、シリンダー温度270℃、金型温度130℃の条件で3mm厚、直径50mmの円盤に成形し、参考例の測定試料とした。
Claims (10)
- ポリエステル樹脂が、前記単位(A)、ジオール単位(B)、及びジカルボン酸又はそのエステル形成性誘導体単位(C)を有する共重合ポリエステル樹脂であり、
前記共重合ポリエステル樹脂の全単位中の前記単位(A)の含有量が10~95mol%である、請求項1に記載のポリエステル樹脂組成物。 - 前記酸化防止剤が、フェノール系酸化防止剤及び/又はリン系酸化防止剤を含む、請求項1又は2に記載のポリエステル樹脂組成物。
- 前記フェノール系酸化防止剤が、1,3,5-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン、4,4’,4’’-(1-メチルプロパニル-3-イリデン)トリス(6-tert-ブチル-m-クレゾール)、n-オクタデシル-3-(3、5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオナート、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオナート]、及び3,9-ビス(2-(3-(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)-1,1-ジメチルエチル)-2,4,8,10-テトラオキサスピロ[5.5]ウンデカンからなる群より選択される少なくとも一種を含む、請求項3に記載のポリエステル樹脂組成物。
- 前記リン系酸化防止剤がトリス(2,4-ジ-tert-ブチルフェニル)ホスファイト、及び3,9-ビス(2,6-ジ-tert-ブチル-4-メチルフェノキシ)-2,4,8,10-テトラオキサ-3,9-ジホスファスピロ[5.5]ウンデカンからなる群より選択される少なくとも一種を含む、請求項3又は4に記載のポリエステル樹脂組成物。
- 前記フェノール系酸化防止剤として、1,3,5-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン及び/又はペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオナート]を含み、
前記リン系酸化防止剤として、3,9-ビス(2,6-ジ-tert-ブチル-4-メチルフェノキシ)-2,4,8,10-テトラオキサ-3,9-ジホスファスピロ[5.5]ウンデカン及び/又はトリス(2,4-ジ-tert-ブチルフェニル)ホスファイトを含む、請求項3~5のいずれか1項に記載のポリエステル樹脂組成物。 - 前記フェノール系酸化防止剤が1,3,5-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオンである、請求項3~6のいずれか1項に記載のポリエステル樹脂組成物。
- 前記リン系酸化防止剤が、3,9-ビス(2,6-ジ-tert-ブチル-4-メチルフェノキシ)-2,4,8,10-テトラオキサ-3,9-ジホスファスピロ[5.5]ウンデカンである、請求項3~7のいずれか1項に記載のポリエステル樹脂組成物。
- 前記フェノール系酸化防止剤の含有量が、前記ポリエステル樹脂100質量部に対し、0.005~1質量部である、請求項3~8のいずれか1項に記載のポリエステル樹脂組成物。
- 前記リン系酸化防止剤の含有量が、前記ポリエステル樹脂100質量部に対し、0.005~1質量部である、請求項3~9のいずれか1項に記載のポリエステル樹脂組成物。
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