WO2017078074A1 - 熱可塑性樹脂の製造方法 - Google Patents
熱可塑性樹脂の製造方法 Download PDFInfo
- Publication number
- WO2017078074A1 WO2017078074A1 PCT/JP2016/082615 JP2016082615W WO2017078074A1 WO 2017078074 A1 WO2017078074 A1 WO 2017078074A1 JP 2016082615 W JP2016082615 W JP 2016082615W WO 2017078074 A1 WO2017078074 A1 WO 2017078074A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- group
- compound represented
- dihydroxy compound
- carbon atoms
- Prior art date
Links
- 229920005992 thermoplastic resin Polymers 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 248
- 238000004519 manufacturing process Methods 0.000 claims abstract description 61
- 239000000376 reactant Substances 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims description 79
- 239000011347 resin Substances 0.000 claims description 79
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 229920005668 polycarbonate resin Polymers 0.000 claims description 45
- 239000004431 polycarbonate resin Substances 0.000 claims description 45
- 230000003287 optical effect Effects 0.000 claims description 44
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 26
- 150000004650 carbonic acid diesters Chemical class 0.000 claims description 23
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 21
- 229920000728 polyester Polymers 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000000465 moulding Methods 0.000 claims description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000012788 optical film Substances 0.000 claims description 5
- 229920001225 polyester resin Polymers 0.000 claims description 5
- 239000004645 polyester resin Substances 0.000 claims description 5
- HVIAEALBBMNFIW-UHFFFAOYSA-N 3-[9-(2-carboxyethyl)fluoren-9-yl]propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)(CCC(O)=O)C3=CC=CC=C3C2=C1 HVIAEALBBMNFIW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 52
- 239000003054 catalyst Substances 0.000 description 35
- -1 2-hydroxyethoxy Chemical group 0.000 description 34
- 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 31
- 239000010408 film Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- 239000002994 raw material Substances 0.000 description 27
- 238000011156 evaluation Methods 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 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 22
- 230000000052 comparative effect Effects 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000006068 polycondensation reaction Methods 0.000 description 16
- 239000013078 crystal Substances 0.000 description 15
- 238000005809 transesterification reaction Methods 0.000 description 15
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- 239000011521 glass Substances 0.000 description 13
- 239000000155 melt Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 12
- 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 11
- 150000003839 salts Chemical class 0.000 description 11
- 238000001746 injection moulding Methods 0.000 description 10
- 238000012545 processing Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 8
- 239000006096 absorbing agent Substances 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 6
- 230000009849 deactivation Effects 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical group C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012760 heat stabilizer Substances 0.000 description 6
- 229920000515 polycarbonate Polymers 0.000 description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 239000011342 resin composition Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000003643 water by type Substances 0.000 description 6
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000001339 alkali metal compounds Chemical class 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 150000004679 hydroxides Chemical class 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- 150000004671 saturated fatty acids Chemical class 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- OVJPYIRGUFWANT-UHFFFAOYSA-N 2-[1-[2-(2-hydroxyethoxy)naphthalen-1-yl]naphthalen-2-yl]oxyethanol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3OCCO)=C(OCCO)C=CC2=C1 OVJPYIRGUFWANT-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000748 compression moulding Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- UNBRVUTVKZVUGM-UHFFFAOYSA-N methyl 3-[9-(3-methoxy-3-oxopropyl)fluoren-9-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OC)(CCC(=O)OC)C3=CC=CC=C3C2=C1 UNBRVUTVKZVUGM-UHFFFAOYSA-N 0.000 description 3
- 239000006082 mold release agent Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- GPFJHNSSBHPYJK-UHFFFAOYSA-N (3-methylphenyl) hydrogen carbonate Chemical compound CC1=CC=CC(OC(O)=O)=C1 GPFJHNSSBHPYJK-UHFFFAOYSA-N 0.000 description 2
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- LAXWTHPUJQUILB-UHFFFAOYSA-N 1h-benzimidazole;1h-imidazole Chemical class C1=CNC=N1.C1=CC=C2NC=NC2=C1 LAXWTHPUJQUILB-UHFFFAOYSA-N 0.000 description 2
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 2
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 2
- LVLNPXCISNPHLE-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1O LVLNPXCISNPHLE-UHFFFAOYSA-N 0.000 description 2
- YBHWVDKCKDWQBX-UHFFFAOYSA-N 2-[2-cyclohexyl-4-[9-[3-cyclohexyl-4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound OCCOC1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OCCO)=CC=2)C2CCCCC2)C=C1C1CCCCC1 YBHWVDKCKDWQBX-UHFFFAOYSA-N 0.000 description 2
- LUXQHIIWBDDUDE-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3-methylphenyl]fluoren-9-yl]-2-methylphenoxy]ethanol Chemical compound C1=C(OCCO)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(OCCO)=CC=2)=C1 LUXQHIIWBDDUDE-UHFFFAOYSA-N 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 description 2
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 description 2
- IJWIRZQYWANBMP-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-propan-2-ylphenyl)propan-2-yl]-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)C)=C1 IJWIRZQYWANBMP-UHFFFAOYSA-N 0.000 description 2
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 2
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- 229920001651 Cyanoacrylate Polymers 0.000 description 2
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- 239000004420 Iupilon Substances 0.000 description 2
- ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 2
- 108010022337 Leucine Enkephalin Proteins 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 2
- 241000282376 Panthera tigris Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical class [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- QOBLJVUECBDJGF-UHFFFAOYSA-N [Mg].CC(O)=O Chemical compound [Mg].CC(O)=O QOBLJVUECBDJGF-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- UCVMQZHZWWEPRC-UHFFFAOYSA-L barium(2+);hydrogen carbonate Chemical compound [Ba+2].OC([O-])=O.OC([O-])=O UCVMQZHZWWEPRC-UHFFFAOYSA-L 0.000 description 2
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- MUCRFDZUHPMASM-UHFFFAOYSA-N bis(2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Cl MUCRFDZUHPMASM-UHFFFAOYSA-N 0.000 description 2
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 2
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000010338 boric acid Nutrition 0.000 description 2
- FLLNLJJKHKZKMB-UHFFFAOYSA-N boron;tetramethylazanium Chemical compound [B].C[N+](C)(C)C FLLNLJJKHKZKMB-UHFFFAOYSA-N 0.000 description 2
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- ZOAIGCHJWKDIPJ-UHFFFAOYSA-M caesium acetate Chemical compound [Cs+].CC([O-])=O ZOAIGCHJWKDIPJ-UHFFFAOYSA-M 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- 229960005147 calcium acetate Drugs 0.000 description 2
- 239000004301 calcium benzoate Substances 0.000 description 2
- 235000010237 calcium benzoate Nutrition 0.000 description 2
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 2
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 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
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- HZQXCUSDXIKLGS-UHFFFAOYSA-L calcium;dibenzoate;trihydrate Chemical compound O.O.O.[Ca+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HZQXCUSDXIKLGS-UHFFFAOYSA-L 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- BLUMOBPWAAOPOY-UHFFFAOYSA-M cesium;benzoate Chemical compound [Cs+].[O-]C(=O)C1=CC=CC=C1 BLUMOBPWAAOPOY-UHFFFAOYSA-M 0.000 description 2
- WLZGEDNSZCPRCJ-UHFFFAOYSA-M cesium;octadecanoate Chemical compound [Cs+].CCCCCCCCCCCCCCCCCC([O-])=O WLZGEDNSZCPRCJ-UHFFFAOYSA-M 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 238000004807 desolvation Methods 0.000 description 2
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 2
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 2
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 2
- VZEGPPPCKHRYGO-UHFFFAOYSA-N diethoxyphosphorylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1 VZEGPPPCKHRYGO-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- REKWWOFUJAJBCL-UHFFFAOYSA-L dilithium;hydrogen phosphate Chemical compound [Li+].[Li+].OP([O-])([O-])=O REKWWOFUJAJBCL-UHFFFAOYSA-L 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- TYJOJLOWRIQYQM-UHFFFAOYSA-L disodium;phenyl phosphate Chemical compound [Na+].[Na+].[O-]P([O-])(=O)OC1=CC=CC=C1 TYJOJLOWRIQYQM-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 238000000752 ionisation method Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 2
- URLZCHNOLZSCCA-UHFFFAOYSA-N leu-enkephalin Chemical compound C=1C=C(O)C=CC=1CC(N)C(=O)NCC(=O)NCC(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=CC=C1 URLZCHNOLZSCCA-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 2
- 229940031993 lithium benzoate Drugs 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 2
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 2
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 2
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 2
- 239000002370 magnesium bicarbonate Substances 0.000 description 2
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- JGIZKLDQCIOYLH-UHFFFAOYSA-L magnesium;phenyl phosphate Chemical compound [Mg+2].[O-]P([O-])(=O)OC1=CC=CC=C1 JGIZKLDQCIOYLH-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 2
- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 2
- LYTNHSCLZRMKON-UHFFFAOYSA-L oxygen(2-);zirconium(4+);diacetate Chemical compound [O-2].[Zr+4].CC([O-])=O.CC([O-])=O LYTNHSCLZRMKON-UHFFFAOYSA-L 0.000 description 2
- PXDJXZJSCPSGGI-UHFFFAOYSA-N palmityl palmitate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000005453 pelletization Methods 0.000 description 2
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 239000004300 potassium benzoate Substances 0.000 description 2
- 235000010235 potassium benzoate Nutrition 0.000 description 2
- 229940103091 potassium benzoate Drugs 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229940114930 potassium stearate Drugs 0.000 description 2
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 229910000018 strontium carbonate Inorganic materials 0.000 description 2
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 2
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 2
- WJMMDJOFTZAHHS-UHFFFAOYSA-L strontium;carbonic acid;carbonate Chemical compound [Sr+2].OC([O-])=O.OC([O-])=O WJMMDJOFTZAHHS-UHFFFAOYSA-L 0.000 description 2
- RXSHXLOMRZJCLB-UHFFFAOYSA-L strontium;diacetate Chemical compound [Sr+2].CC([O-])=O.CC([O-])=O RXSHXLOMRZJCLB-UHFFFAOYSA-L 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 2
- 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 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 2
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- FEODVXCWZVOEIR-UHFFFAOYSA-N (2,4-ditert-butylphenyl) octyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C FEODVXCWZVOEIR-UHFFFAOYSA-N 0.000 description 1
- SXJSETSRWNDWPP-UHFFFAOYSA-N (2-hydroxy-4-phenylmethoxyphenyl)-phenylmethanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C(O)=CC=1OCC1=CC=CC=C1 SXJSETSRWNDWPP-UHFFFAOYSA-N 0.000 description 1
- WXENKXQUTQFQIP-PLKIVWSFSA-N (2e,4e)-hexa-2,4-dienoic acid;octadecanoic acid Chemical compound C\C=C\C=C\C(O)=O.CCCCCCCCCCCCCCCCCC(O)=O WXENKXQUTQFQIP-PLKIVWSFSA-N 0.000 description 1
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
- FUAMQXCTIUGPJK-UHFFFAOYSA-N (5-benzoyl-4-hydroxy-2-methoxyphenyl) hydrogen sulfate Chemical compound C1=C(OS(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 FUAMQXCTIUGPJK-UHFFFAOYSA-N 0.000 description 1
- UONCERAQKBPLML-UHFFFAOYSA-N (6-ethoxypyridin-3-yl)boronic acid Chemical compound CCOC1=CC=C(B(O)O)C=N1 UONCERAQKBPLML-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 1
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- 229940083957 1,2-butanediol Drugs 0.000 description 1
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound 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 description 1
- DMBUODUULYCPAK-UHFFFAOYSA-N 1,3-bis(docosanoyloxy)propan-2-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCC DMBUODUULYCPAK-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- GSOBKKBOWPKAMP-UHFFFAOYSA-N 1-(2-phenylphenoxy)ethanol Chemical compound CC(O)OC1=CC=CC=C1C1=CC=CC=C1 GSOBKKBOWPKAMP-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- UAXNXOMKCGKNCI-UHFFFAOYSA-N 1-diphenylphosphanylethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 UAXNXOMKCGKNCI-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- CYXGBTZYTXLVDN-UHFFFAOYSA-N 1-octoxyphosphonoyloxyoctane Chemical compound CCCCCCCCOP(=O)OCCCCCCCC CYXGBTZYTXLVDN-UHFFFAOYSA-N 0.000 description 1
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 1
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WZUNUACWCJJERC-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CC)(CO)CO WZUNUACWCJJERC-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 1
- LEVFXWNQQSSNAC-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound OC1=CC(OCCCCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 LEVFXWNQQSSNAC-UHFFFAOYSA-N 0.000 description 1
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 1
- ARBJOSNLPIFBTO-UHFFFAOYSA-N 2-[2-(2H-benzotriazol-4-yl)phenyl]-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound CC(C)(c1ccccc1)c1cc(c(O)c(c1)C(C)(C)c1ccccc1)-c1ccccc1-c1cccc2[nH]nnc12 ARBJOSNLPIFBTO-UHFFFAOYSA-N 0.000 description 1
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- CUPZWXCTZHAVPP-UHFFFAOYSA-N 2-[2-tert-butyl-4-[9-[3-tert-butyl-4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=C(OCCO)C(C(C)(C)C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OCCO)=CC=2)C(C)(C)C)=C1 CUPZWXCTZHAVPP-UHFFFAOYSA-N 0.000 description 1
- MPLFLOQPUPLZHI-UHFFFAOYSA-N 2-[3-methyl-4-(4-oxo-3,1-benzoxazin-2-yl)phenyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C=3C=C(C(=CC=3)C=3OC(=O)C4=CC=CC=C4N=3)C)=NC2=C1 MPLFLOQPUPLZHI-UHFFFAOYSA-N 0.000 description 1
- XXKGLWFBWIYJEH-UHFFFAOYSA-N 2-[3-nitro-4-(4-oxo-3,1-benzoxazin-2-yl)phenyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C=3C=C(C(=CC=3)C=3OC(=O)C4=CC=CC=C4N=3)[N+](=O)[O-])=NC2=C1 XXKGLWFBWIYJEH-UHFFFAOYSA-N 0.000 description 1
- ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 description 1
- RGMDGTAYZZQRBC-UHFFFAOYSA-N 2-[4-(4-oxo-1,3-benzoxazin-2-yl)phenyl]-1,3-benzoxazin-4-one Chemical compound C1=CC=C2OC(C3=CC=C(C=C3)C3=NC(C4=CC=CC=C4O3)=O)=NC(=O)C2=C1 RGMDGTAYZZQRBC-UHFFFAOYSA-N 0.000 description 1
- IRTFFZWZLVOXMG-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]fluoren-9-yl]-2,6-dimethylphenoxy]ethanol Chemical compound CC1=C(OCCO)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(OCCO)=C(C)C=2)=C1 IRTFFZWZLVOXMG-UHFFFAOYSA-N 0.000 description 1
- WXNRFPMJYZGKSS-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3-propan-2-ylphenyl]fluoren-9-yl]-2-propan-2-ylphenoxy]ethanol Chemical compound C1=C(OCCO)C(C(C)C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OCCO)=CC=2)C(C)C)=C1 WXNRFPMJYZGKSS-UHFFFAOYSA-N 0.000 description 1
- UZOYICMDDCNJJG-UHFFFAOYSA-N 2-[[3-(benzotriazol-2-yl)-2-hydroxy-5-methylphenyl]methyl]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C)=CC(CN2C(C3=C(CCCC3)C2=O)=O)=C1O UZOYICMDDCNJJG-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- OPJWPPVYCOPDCM-UHFFFAOYSA-N 2-ethylhexyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CC)CCCC OPJWPPVYCOPDCM-UHFFFAOYSA-N 0.000 description 1
- UFMBOFGKHIXOTA-UHFFFAOYSA-N 2-methylterephthalic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C(O)=O UFMBOFGKHIXOTA-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- RKSBPFMNOJWYSB-UHFFFAOYSA-N 3,3-Bis(4-hydroxyphenyl)pentane Chemical compound C=1C=C(O)C=CC=1C(CC)(CC)C1=CC=C(O)C=C1 RKSBPFMNOJWYSB-UHFFFAOYSA-N 0.000 description 1
- AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WBWXVCMXGYSMQA-UHFFFAOYSA-N 3,9-bis[2,4-bis(2-phenylpropan-2-yl)phenoxy]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C=1C=C(OP2OCC3(CO2)COP(OC=2C(=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C(C)(C)C=2C=CC=CC=2)OC3)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 WBWXVCMXGYSMQA-UHFFFAOYSA-N 0.000 description 1
- OGYNJAOUDVVFMR-UHFFFAOYSA-N 3-[1-[2-(3-hydroxypropoxy)naphthalen-1-yl]naphthalen-2-yl]oxypropan-1-ol Chemical compound OCCCOC1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)OCCCO OGYNJAOUDVVFMR-UHFFFAOYSA-N 0.000 description 1
- VPMIEDAGSULEBW-UHFFFAOYSA-N 3-[3-(1-carboxy-2-methylpropan-2-yl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]-3-methylbutanoic acid Chemical compound C1OC(C(C)(CC(O)=O)C)OCC21COC(C(C)(C)CC(O)=O)OC2 VPMIEDAGSULEBW-UHFFFAOYSA-N 0.000 description 1
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- NKYBNVBIWYHWQM-UHFFFAOYSA-N 4-(1-diethoxyphosphoryl-2,2-dimethylpropyl)phenol Chemical compound C(C)(C)(C)C(C1=CC=C(C=C1)O)P(OCC)(OCC)=O NKYBNVBIWYHWQM-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- SVOBELCYOCEECO-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-methylphenyl)cyclohexyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(CCCCC2)C=2C=C(C)C(O)=CC=2)=C1 SVOBELCYOCEECO-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- ACWKCNYOCGALDS-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-diphenylphenyl)propan-2-yl]-2,6-diphenylphenol Chemical compound C=1C(C=2C=CC=CC=2)=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=C(C=1O)C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 ACWKCNYOCGALDS-UHFFFAOYSA-N 0.000 description 1
- BKTRENAPTCBBFA-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-phenylphenyl)propan-2-yl]-2-phenylphenol Chemical compound C=1C=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC=C(O)C=1C1=CC=CC=C1 BKTRENAPTCBBFA-UHFFFAOYSA-N 0.000 description 1
- WCUDAIJOADOKAW-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)pentan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCC)C1=CC=C(O)C=C1 WCUDAIJOADOKAW-UHFFFAOYSA-N 0.000 description 1
- KBKLXLYSUOMJQE-UHFFFAOYSA-N 4-[9-(4-hydroxy-2-methylphenyl)fluoren-9-yl]-3-methylphenol Chemical compound CC1=CC(O)=CC=C1C1(C=2C(=CC(O)=CC=2)C)C2=CC=CC=C2C2=CC=CC=C21 KBKLXLYSUOMJQE-UHFFFAOYSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- ZVVFVKJZNVSANF-UHFFFAOYSA-N 6-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]hexyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCCCCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 ZVVFVKJZNVSANF-UHFFFAOYSA-N 0.000 description 1
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- NJIZOAZJRKRZHQ-UHFFFAOYSA-N C(CCCCCCCCCCC)C(C(=O)O)(CSCCC(=O)O)CCCCCCCCCCCC.C(CCCCCCCCCCCCCCCCC)CCC(=S)O.C(CCCCCCCCCCCCCCCCC)CCC(=S)O.C(CCCCCCCCCCCCCCCCC)CCC(=S)O.C(CCCCCCCCCCCCCCCCC)CCC(=S)O.OCC(CO)(CO)CO Chemical compound C(CCCCCCCCCCC)C(C(=O)O)(CSCCC(=O)O)CCCCCCCCCCCC.C(CCCCCCCCCCCCCCCCC)CCC(=S)O.C(CCCCCCCCCCCCCCCCC)CCC(=S)O.C(CCCCCCCCCCCCCCCCC)CCC(=S)O.C(CCCCCCCCCCCCCCCCC)CCC(=S)O.OCC(CO)(CO)CO NJIZOAZJRKRZHQ-UHFFFAOYSA-N 0.000 description 1
- VBTIYKDZCFBWNU-UHFFFAOYSA-N C1(=CC(=CC=C1)C1=NC2=C(C(O1)=O)C=CC=C2)C2=NC1=C(C(O2)=O)C=CC=C1.C1(=CC=C(C=C1)C1=NC2=C(C(O1)=O)C=CC=C2)C2=NC1=C(C(O2)=O)C=CC=C1 Chemical compound C1(=CC(=CC=C1)C1=NC2=C(C(O1)=O)C=CC=C2)C2=NC1=C(C(O2)=O)C=CC=C1.C1(=CC=C(C=C1)C1=NC2=C(C(O1)=O)C=CC=C2)C2=NC1=C(C(O2)=O)C=CC=C1 VBTIYKDZCFBWNU-UHFFFAOYSA-N 0.000 description 1
- LKUNXBRZDFMZOK-GFCCVEGCSA-N Capric acid monoglyceride Natural products CCCCCCCCCC(=O)OC[C@H](O)CO LKUNXBRZDFMZOK-GFCCVEGCSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- FRZFVJFGJXFYMW-UHFFFAOYSA-N OCCCCOC1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)OCCCCO Chemical compound OCCCCOC1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)OCCCCO FRZFVJFGJXFYMW-UHFFFAOYSA-N 0.000 description 1
- JWZOHRVCZRNDKO-UHFFFAOYSA-N OCCOC1=C(C=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC(=C(C=C1)OCCO)C(C)C)C(C)C.OCCOC1=C(C=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC(=C(C=C1)OCCO)C(C)(C)C)C(C)(C)C Chemical compound OCCOC1=C(C=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC(=C(C=C1)OCCO)C(C)C)C(C)C.OCCOC1=C(C=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC(=C(C=C1)OCCO)C(C)(C)C)C(C)(C)C JWZOHRVCZRNDKO-UHFFFAOYSA-N 0.000 description 1
- STOLTOYHKROIMJ-UHFFFAOYSA-N OCCOC1=C(C=CC=C2C(C3=CC=CC=C3C=C3)=C3OCCO)C2=CC=C1 Chemical compound OCCOC1=C(C=CC=C2C(C3=CC=CC=C3C=C3)=C3OCCO)C2=CC=C1 STOLTOYHKROIMJ-UHFFFAOYSA-N 0.000 description 1
- XAZWSYXCHDYDNQ-UHFFFAOYSA-N OCOC1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)OCO Chemical compound OCOC1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)OCO XAZWSYXCHDYDNQ-UHFFFAOYSA-N 0.000 description 1
- CUUYDUQLVLQSGI-UHFFFAOYSA-N OP(O)OP(O)O.C(CCCCCCCC)C1=C(C=CC=C1)C(O)C(CO)(CO)CO Chemical compound OP(O)OP(O)O.C(CCCCCCCC)C1=C(C=CC=C1)C(O)C(CO)(CO)CO CUUYDUQLVLQSGI-UHFFFAOYSA-N 0.000 description 1
- ODRWJRFALQTLOR-UHFFFAOYSA-N OP(O)OP(O)O.C(CCCCCCCCCCCCCCCCC)C(O)(C(CO)(CO)CO)CCCCCCCCCCCCCCCCCC.P(O)(O)O Chemical compound OP(O)OP(O)O.C(CCCCCCCCCCCCCCCCC)C(O)(C(CO)(CO)CO)CCCCCCCCCCCCCCCCCC.P(O)(O)O ODRWJRFALQTLOR-UHFFFAOYSA-N 0.000 description 1
- GWFGDXZQZYMSMJ-UHFFFAOYSA-N Octadecansaeure-heptadecylester Natural products CCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC GWFGDXZQZYMSMJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-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
- 241001483078 Phyto Species 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- CZEQLYJOEGYWPO-UHFFFAOYSA-N [2,3-bis(2,4-ditert-butylphenyl)-4-phenylphenyl]phosphonous acid Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1C1=C(P(O)O)C=CC(C=2C=CC=CC=2)=C1C1=CC=C(C(C)(C)C)C=C1C(C)(C)C CZEQLYJOEGYWPO-UHFFFAOYSA-N 0.000 description 1
- IZMPAOFESFSUKJ-UHFFFAOYSA-N [2,4-bis(2,4-ditert-butylphenyl)-3-phenylphenyl]phosphonous acid Chemical compound CC(C)(C)C1=CC(=C(C=C1)C2=C(C(=C(C=C2)P(O)O)C3=C(C=C(C=C3)C(C)(C)C)C(C)(C)C)C4=CC=CC=C4)C(C)(C)C IZMPAOFESFSUKJ-UHFFFAOYSA-N 0.000 description 1
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 description 1
- CGRTZESQZZGAAU-UHFFFAOYSA-N [2-[3-[1-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]-2-methylpropan-2-yl]-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]-2-methylpropyl] 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCC(C)(C)C2OCC3(CO2)COC(OC3)C(C)(C)COC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 CGRTZESQZZGAAU-UHFFFAOYSA-N 0.000 description 1
- LZGAFUNRMOUFFI-UHFFFAOYSA-N [3-(2-cyano-3,3-diphenylprop-2-enoyl)oxyphenyl] 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=C(C#N)C(=O)OC(C=1)=CC=CC=1OC(=O)C(C#N)=C(C=1C=CC=CC=1)C1=CC=CC=C1 LZGAFUNRMOUFFI-UHFFFAOYSA-N 0.000 description 1
- VSVVZZQIUJXYQA-UHFFFAOYSA-N [3-(3-dodecylsulfanylpropanoyloxy)-2,2-bis(3-dodecylsulfanylpropanoyloxymethyl)propyl] 3-dodecylsulfanylpropanoate Chemical compound CCCCCCCCCCCCSCCC(=O)OCC(COC(=O)CCSCCCCCCCCCCCC)(COC(=O)CCSCCCCCCCCCCCC)COC(=O)CCSCCCCCCCCCCCC VSVVZZQIUJXYQA-UHFFFAOYSA-N 0.000 description 1
- DCBVRWAFSWCCCH-UHFFFAOYSA-N [3-(hydroxymethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl]methanol Chemical compound C1CCCC2CC(CO)C(CO)CC21 DCBVRWAFSWCCCH-UHFFFAOYSA-N 0.000 description 1
- RABVYVVNRHVXPJ-UHFFFAOYSA-N [3-(hydroxymethyl)-1-adamantyl]methanol Chemical compound C1C(C2)CC3CC1(CO)CC2(CO)C3 RABVYVVNRHVXPJ-UHFFFAOYSA-N 0.000 description 1
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BNHVSHVDYVQSNW-UHFFFAOYSA-N [3-[3-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound C(C)(C)(C)C1=C(OP(C=2C=C(C=CC=2)C=2C=C(C=CC=2)P(OC2=C(C=C(C=C2)C(C)(C)C)C(C)(C)C)OC2=C(C=C(C=C2)C(C)(C)C)C(C)(C)C)OC2=C(C=C(C=C2)C(C)(C)C)C(C)(C)C)C=CC(=C1)C(C)(C)C BNHVSHVDYVQSNW-UHFFFAOYSA-N 0.000 description 1
- IBKKMFMBXQARGV-UHFFFAOYSA-N [3-nonanoyloxy-2,2-bis(nonanoyloxymethyl)propyl] nonanoate Chemical compound CCCCCCCCC(=O)OCC(COC(=O)CCCCCCCC)(COC(=O)CCCCCCCC)COC(=O)CCCCCCCC IBKKMFMBXQARGV-UHFFFAOYSA-N 0.000 description 1
- OCKWAZCWKSMKNC-UHFFFAOYSA-N [3-octadecanoyloxy-2,2-bis(octadecanoyloxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC OCKWAZCWKSMKNC-UHFFFAOYSA-N 0.000 description 1
- IQXDUKXUDQPOBC-UHFFFAOYSA-N [3-octadecanoyloxy-2-[[3-octadecanoyloxy-2,2-bis(octadecanoyloxymethyl)propoxy]methyl]-2-(octadecanoyloxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)COCC(COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC IQXDUKXUDQPOBC-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)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 BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 1
- RIBGZYZMHIANTO-UHFFFAOYSA-N [5-(hydroxymethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl]methanol Chemical compound OCC1CCCC2C(CO)CCCC21 RIBGZYZMHIANTO-UHFFFAOYSA-N 0.000 description 1
- KBWLBXSZWRTHKM-UHFFFAOYSA-N [6-(hydroxymethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl]methanol Chemical compound C1C(CO)CCC2CC(CO)CCC21 KBWLBXSZWRTHKM-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- KYQRDNYMKKJUTH-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-dicarboxylic acid Chemical compound C1CC2(C(O)=O)C(C(=O)O)CC1C2 KYQRDNYMKKJUTH-UHFFFAOYSA-N 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- HHBIQTAAJCSNCD-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone;bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O.OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O HHBIQTAAJCSNCD-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000005619 boric acid group Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- QYJXDIUNDMRLAO-UHFFFAOYSA-N butyl 4-methylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=C(C)C=C1 QYJXDIUNDMRLAO-UHFFFAOYSA-N 0.000 description 1
- ZWRWUGGYDBHANL-UHFFFAOYSA-N butyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCC)OC1=CC=CC=C1 ZWRWUGGYDBHANL-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003484 crystal nucleating agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-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
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- XFUSKHPBJXJFRA-UHFFFAOYSA-N dihexyl hydrogen phosphite Chemical compound CCCCCCOP(O)OCCCCCC XFUSKHPBJXJFRA-UHFFFAOYSA-N 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- OXDOANYFRLHSML-UHFFFAOYSA-N dimethoxyphosphorylbenzene Chemical compound COP(=O)(OC)C1=CC=CC=C1 OXDOANYFRLHSML-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- XMQYIPNJVLNWOE-UHFFFAOYSA-N dioctyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OCCCCCCCC XMQYIPNJVLNWOE-UHFFFAOYSA-N 0.000 description 1
- MKZVQIIAAIPNGH-UHFFFAOYSA-N dioctyl phenyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OC1=CC=CC=C1 MKZVQIIAAIPNGH-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- PXGLYSITKOROKV-UHFFFAOYSA-N dipropoxyphosphorylbenzene Chemical compound CCCOP(=O)(OCCC)C1=CC=CC=C1 PXGLYSITKOROKV-UHFFFAOYSA-N 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- VBVCYAZECWLFHP-UHFFFAOYSA-N dodecyl benzenesulfonate;tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC.CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 VBVCYAZECWLFHP-UHFFFAOYSA-N 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000007688 edging Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- IVQOVYWBHRSGJI-UHFFFAOYSA-N hexyl 4-methylbenzenesulfonate Chemical compound CCCCCCOS(=O)(=O)C1=CC=C(C)C=C1 IVQOVYWBHRSGJI-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- QJXZDBOIVBLYSJ-UHFFFAOYSA-N o-[3-heptadecanethioyloxy-2,2-bis(heptadecanethioyloxymethyl)propyl] heptadecanethioate Chemical compound CCCCCCCCCCCCCCCCC(=S)OCC(COC(=S)CCCCCCCCCCCCCCCC)(COC(=S)CCCCCCCCCCCCCCCC)COC(=S)CCCCCCCCCCCCCCCC QJXZDBOIVBLYSJ-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- KCRLWVVFAVLSAP-UHFFFAOYSA-N octyl dihydrogen phosphite Chemical compound CCCCCCCCOP(O)O KCRLWVVFAVLSAP-UHFFFAOYSA-N 0.000 description 1
- AXRSHKZFNKUGQB-UHFFFAOYSA-N octyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC)OC1=CC=CC=C1 AXRSHKZFNKUGQB-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- CHJUOCDSZWMLRU-UHFFFAOYSA-N oxo(dipropoxy)phosphanium Chemical compound CCCO[P+](=O)OCCC CHJUOCDSZWMLRU-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- VCAFTIGPOYBOIC-UHFFFAOYSA-N phenyl dihydrogen phosphite Chemical compound OP(O)OC1=CC=CC=C1 VCAFTIGPOYBOIC-UHFFFAOYSA-N 0.000 description 1
- SMIZARYCGYRDGF-UHFFFAOYSA-N phenyl dipropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC1=CC=CC=C1 SMIZARYCGYRDGF-UHFFFAOYSA-N 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- QVLTXCYWHPZMCA-UHFFFAOYSA-N po4-po4 Chemical class OP(O)(O)=O.OP(O)(O)=O QVLTXCYWHPZMCA-UHFFFAOYSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229940093625 propylene glycol monostearate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- AJHKJOCIGPIJFZ-UHFFFAOYSA-N tris(2,6-ditert-butylphenyl) phosphite Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1OP(OC=1C(=CC=CC=1C(C)(C)C)C(C)(C)C)OC1=C(C(C)(C)C)C=CC=C1C(C)(C)C AJHKJOCIGPIJFZ-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
- G02B27/09—Beam shaping, e.g. changing the cross-sectional area, not otherwise provided for
- G02B27/0938—Using specific optical elements
- G02B27/095—Refractive optical elements
- G02B27/0955—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
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- 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
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
- C08L69/005—Polyester-carbonates
-
- 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
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/16—Applications used for films
Definitions
- the present invention relates to a thermoplastic resin excellent in fluidity and tensile strength.
- plastic lenses are preferably used rather than glass lenses. The reason is that a plastic lens can cope with various shapes such as a thin shape and an aspherical surface, is inexpensive, and is easily mass-produced by injection molding.
- Optical lenses made of transparent optical resins have the advantage that they can be mass-produced by injection molding and are easy to manufacture aspherical lenses, and are currently used as camera lenses.
- polycarbonate made of bisphenol A (BPA) has been the mainstream as a transparent resin for optics, but a fluorene skeleton such as 9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene (BPEF) is used.
- BPA bisphenol A
- BPEF 9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene
- thermoplastic resin that is useful as an optical material and has excellent fluidity and tensile strength.
- thermoplastic resin excellent in fluidity and / or tensile strength.
- the present inventors have found that the above-mentioned problems can be solved by allowing a specific amount of a specific dihydroxy compound to be present in a dihydroxy compound having a specific fluorene skeleton. Reached. That is, the present invention is as follows, for example.
- the dihydroxy compound is A dihydroxy compound represented by the following formula (1); At least one of a compound represented by the following formula (A), a compound represented by the following formula (B), and a compound represented by the following formula (C); Including The total weight of the compound represented by the formula (A), the compound represented by the formula (B), and the compound represented by the formula (C) is the weight of the dihydroxy compound represented by the formula (1) ( 100 parts by weight), the production method is 1,500 ppm or more.
- R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or 1 to 20 carbon atoms. Selected from the group consisting of an alkoxyl group, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aryloxy group having 6 to 20 carbon atoms.
- the weight of the compound represented by the formula (A) in the dihydroxy compound is 1,000 ppm or more with respect to the weight (100 parts by weight) of the dihydroxy compound represented by the formula (1).
- the weight of the compound represented by the formula (B) in the dihydroxy compound is 200 ppm or more with respect to the weight (100 parts by weight) of the dihydroxy compound represented by the formula (1).
- the weight of the compound represented by the formula (C) in the dihydroxy compound is 200 ppm or more with respect to the weight (100 parts by weight) of the dihydroxy compound represented by the formula (1).
- the dihydroxy compound further contains at least one selected from the group consisting of a dihydroxy compound represented by the following formula (2) and a dihydroxy compound represented by the following formula (3): [4] The production method according to any one of [4].
- each X is independently an alkylene group having 1 to 4 carbon atoms.
- R 6 and R 7 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, or an alkyl group having 5 to 20 carbon atoms.
- Z 1 and Z 2 are each independently selected from the group consisting of an alkylene group having 1 to 8 carbon atoms, a cycloalkylene group having 6 to 10 carbon atoms, and an arylene group having 6 to 10 carbon atoms; l 1 and l 2 are each independently an integer from 0 to 5; Q is a single bond or Selected from the group consisting of
- R 8 , R 9 , R 14 to R 17 are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, and a phenyl group;
- R 10 to R 13 each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms;
- Z ′ is a single bond or Selected from the group consisting of
- thermoplastic resin is selected from the group consisting of a polycarbonate resin, a polyester resin, and a polyester carbonate resin.
- thermoplastic resin is a polycarbonate resin.
- reactant further contains a carbonic acid diester.
- the thermoplastic resin is a polyester carbonate resin
- the reactant includes the dihydroxy compound, a carbonic acid diester, a dicarboxylic acid containing at least one selected from terephthalic acid, 2,6-naphthalenedicarboxylic acid, and fluorene-9,9-dipropionic acid or a derivative thereof.
- a molar ratio of the dihydroxy compound to the dicarboxylic acid or a derivative thereof is 20/80 to 95/5 (dihydroxy compound / dicarboxylic acid or a derivative thereof).
- [12] A method for producing a molded body, comprising a step of molding the thermoplastic resin obtained by the production method according to any one of [1] to [11].
- An optical material characterized by using a thermoplastic resin obtained by the production method according to any one of [1] to [11] or a molded article obtained by the production method according to [12]. Manufacturing method.
- thermoplastic resin excellent in fluidity and / or tensile strength can be obtained.
- One embodiment of the present invention is a method for producing a thermoplastic resin by reacting a reactant containing a dihydroxy compound, wherein the dihydroxy compound includes a dihydroxy compound represented by the following formula (1) and a formula (A ), A compound represented by the following formula (B), and a compound represented by the following formula (C), and a compound represented by the above formula (A), the formula (
- the total weight of the compound represented by B) and the compound represented by formula (C) is 1,500 ppm or more with respect to the weight (100 parts by weight) of the dihydroxy compound represented by formula (1). It relates to a manufacturing method.
- thermoplastic resin having a structural unit derived from a compound having a fluorene skeleton represented by the formula (1) has a high refractive index and is suitable for an optical material, but has a problem of low fluidity and low tensile strength. there were.
- the inventor of the present application includes, as a monomer (raw material), a reaction containing a specific amount of the compound represented by the above formulas (A), (B), and (C) together with the dihydroxy compound represented by the formula (1).
- the compound represented by the formula (A), (B), and / or (C), and / or a polymer thereof functions as a plasticizer, and the fluidity and / or the thermoplastic resin. It has been found that the tensile strength can be improved.
- the compound represented by the above formula (A), formula (B), or formula (C) can be by-produced as an impurity in the process of synthesizing the dihydroxy compound represented by formula (1).
- the raw material in general, in a chemical reaction including a polymerization reaction, it is preferable that the raw material has a higher chemical purity.
- a resin containing a small amount of the above-described components can be obtained with excellent fluidity and obtained tensile strength.
- the dihydroxy compound represented by the formula (1) has a fluorene structure as an impurity by-produced in the course of synthesis, in addition to the compounds represented by the formula (A), the formula (B), and the formula (C). Contains a plurality of by-product compounds. Examples of by-product compounds other than formula (A), formula (B), and formula (C) are as follows:
- the present inventors have surprisingly found that among the impurities that were supposed to be reduced, the compounds represented by the above formulas (A), (B), and (C) are particularly excellent in fluidity and tensile strength. It has been found that the characteristics of the resulting resin can be improved by making the total content of these components a certain amount or more.
- the production method of the present invention includes a compound represented by the formula (A), a compound represented by the formula (B), and a compound represented by the formula (C) contained in a dihydroxy compound that is a raw material of a thermoplastic resin.
- the total weight is 1,500 ppm or more with respect to 100 parts by weight of the dihydroxy compound represented by the formula (1). When the total weight is 1,500 ppm or more, the fluidity and / or tensile properties of the thermoplastic resin can be improved.
- the total weight of the compound represented by the formula (A), the compound represented by the formula (B), and the compound represented by the formula (C) is more preferably 2,000 ppm or more, and further preferably 3 1,000 ppm or more.
- the upper limit of the total weight of the compound represented by the formula (A), the compound represented by the formula (B), and the compound represented by the formula (C) is not particularly limited, but when molding the resin, In consideration of maintaining the strength (for example, impact strength) of the molded body, suppressing water absorption, maintaining heat resistance, and / or maintaining moldability, it is preferably 20,000 ppm or less, more preferably 16,000 ppm or less.
- the weight of the compound represented by formula (A) in the dihydroxy compound is based on the weight (100 parts by weight) of the dihydroxy compound represented by formula (1) from the viewpoint of improving the fluidity and tensile strength of the thermoplastic resin.
- it is 1,000 ppm or more, more preferably 2,000 ppm or more, still more preferably 2,500 ppm or more, and particularly preferably 3,000 ppm or more.
- the upper limit is not particularly limited, but is preferably 10,000 ppm or less, more preferably 9,000 ppm or less in consideration of suppressing water absorption, maintaining heat resistance, and / or maintaining moldability.
- the weight of the compound represented by the formula (B) in the dihydroxy compound is the weight of the dihydroxy compound represented by the formula (1) (100 parts by weight) from the viewpoint of improving the fluidity and tensile strength of the thermoplastic resin.
- it is preferably 200 ppm or more.
- it may be 600 ppm or more or 2,000 ppm or more.
- the upper limit is not particularly limited, but is preferably 5,000 ppm or less, more preferably 4,000 ppm or less in consideration of maintaining the strength (for example, impact strength) of the molded body when the resin is molded.
- the weight of the compound represented by the formula (C) in the dihydroxy compound is the weight of the dihydroxy compound represented by the formula (1) (100 parts by weight) from the viewpoint of improving the fluidity and tensile strength of the thermoplastic resin.
- it is preferably 200 ppm or more.
- it may be 500 ppm or more, or 800 ppm or more, 1,000 ppm or more, or 3,000 ppm or more.
- the upper limit is not particularly limited, but is preferably 5,000 ppm or less, more preferably 4,000 ppm or less in consideration of maintaining heat resistance and / or maintaining moldability.
- the amount of the compound represented by the formula (A), the compound represented by the formula (B), and the compound represented by the formula (C) contained in the dihydroxy compound was determined by a liquid chromatograph mass spectrometer (LC- MS).
- An example of LC-MS measurement conditions is as follows. (LC-MS measurement conditions) ⁇ LC: Waters Acquity UPLC Flow rate: 0.5ml / min Temperature: 60 ° C Detector: UV254nm Column: Waters BEII phenyl (diameter 2.1mm x length 100mm, particle diameter 1.7um) Eluent: A mixed solution of A; water, B; methanol was used. The changes in the mixing ratio over time are shown below.
- MS Waters MALDI-Synapt HDMS Mode: MS Scan range: 100-1500 / 0.3sec Ionization method: ESI (+) Resolution: 8500 (Vmode) Capillary voltage: 3kV Code voltage: 30V Trap collision energy: 5V Transfer collision energy: 5V Source temperature: 150 °C Desolvation temperature: 500 °C Injection volume: 2 ⁇ l Internal reference material (mass correction): Leucine Enkephalin, 0.5ng / ul Internal standard flow rate: 0.1ml / min
- the method of setting the content of the compound represented by the formula (A), the compound represented by the formula (B), and the compound represented by the formula (C) to a certain amount or more is not particularly limited.
- a method of adding a compound represented by formula (A), a compound represented by formula (B), and / or a compound represented by formula (C) to a dihydroxy compound as a raw material, in formula (A) A method using a low purity dihydroxy compound containing a certain amount of the compound represented by formula (B) and / or the compound represented by formula (C), and the dihydroxy compound represented by formula (1) (For example, the reaction temperature and reaction time are, for example, 100 to 140 ° C. and 1 to 30 hours, for example, about 100 ° C.
- thermoplastic resin obtained by the production method of the present invention will be described.
- thermoplastic resin obtained by the production method of the embodiment of the present invention is produced by reacting a reaction product containing a dihydroxy compound represented by the formula (1), and is derived from the dihydroxy compound represented by the formula (1).
- the structural unit (1) ′ to be included is included.
- * represents a bonding part.
- the resin using the compound of the above formula (1) as a raw material exhibits physical properties such as a high refractive index, a low Abbe number, a high transparency, a glass transition temperature suitable for injection molding, a low birefringence, and the like.
- an optical component such as an excellent optical lens substantially free from optical distortion can be obtained.
- thermoplastic resin a polyester resin, a polyester carbonate resin, or a polycarbonate resin is preferable. Especially, since it is excellent in heat resistance and hydrolysis resistance, it is preferable to contain polycarbonate resin.
- a thermoplastic resin may be included singly or in combination of two or more.
- Optical characteristics such as refractive index, Abbe number, and birefringence value are greatly affected by the chemical structure of the structural units, and the influence of whether the chemical bond between the structural units is an ester bond or a carbonate bond is relatively small.
- the influence of impurities is also greatly affected by the chemical structure of the constituent units constituting the resin, and is due to differences in chemical bonds (ester bonds, carbonate bonds) between the constituent units. The impact is relatively small.
- the thermoplastic resin according to the embodiment of the present invention is produced by reacting a reactant containing a dihydroxy compound.
- a reactant containing a dihydroxy compound For example, it is produced by polycondensation using a dihydroxy compound containing a dihydroxy compound represented by the formula (1) as a raw material.
- the functional group contributing to polycondensation is an alcoholic hydroxyl group or a phenolic hydroxyl group.
- the structural unit (1) ′ derived from the compound represented by the formula (1) is bonded to a carbonate bond by a polycondensation reaction between the compound represented by the formula (1) and a carbonic acid diester and / or dicarboxylic acid or a derivative thereof. And / or via an ester bond.
- a thermoplastic resin containing the structural unit (1) ′ derived from the dihydroxy compound represented by the formula (1) can be obtained.
- R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, or a carbon number of 5 Is selected from the group consisting of ⁇ 20 cycloalkoxyl carbon atoms, aryl groups having 6-20 carbon atoms, or aryloxy groups having 6-20 carbon atoms.
- a compound in which R 1 and R 2 are a hydrogen atom and an aryl group having 6 to 20 carbon atoms is preferable because the melt fluidity when molded as an optical lens is improved.
- Examples of the compound represented by the formula (1) include 9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene, 9,9-bis (4- (2-hydroxyethoxy) -3-methylphenyl ) Fluorene, 9,9-bis (4- (2-hydroxyethoxy) -3,5-dimethylphenyl) fluorene, 9,9-bis (4- (2-hydroxyethoxy) -3-tert-butylphenyl) fluorene 9,9-bis (4- (2-hydroxyethoxy) -3-isopropylphenyl) fluorene, 9,9-bis (4- (2-hydroxyethoxy) -3-cyclohexylphenyl) fluorene, 9,9-bis (4- (2-hydroxyethoxy) -3-phenylphenyl) fluorene and the like.
- 9,9-bis (4- (2-hydroxyethoxy) -3-phenylphenyl) fluorene and 9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene are preferred, and 9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene is more preferred. These may be used alone or in combination of two or more.
- the proportion of the dihydroxy compound of the formula (1) is preferably 1 to 100 mol%, more preferably 30 to 100 mol%, based on 100 mol% of the dihydroxy compound used as a raw material for the thermoplastic resin, Preferably, it is 40 to 100 mol%.
- the proportion of the dihydroxy compound of the formula (1) is preferably 1 to 100 mol%, more preferably 30 to 100 mol% with respect to 100 mol% of all monomers used as a raw material for the thermoplastic resin. More preferably, it is 40 to 100 mol%.
- the dihydroxy compound includes at least one of a compound represented by formula (A), a compound represented by formula (B), and a compound represented by formula (C). These compounds are usually subjected to a polycondensation reaction with the dihydroxy compound of the formula (1), and in the thermoplastic resin, in the structural units (A) ′ and (B) derived from the compound represented by the formula (A)
- the structural unit (B) ′ derived from the represented compound and the structural unit (C) ′ derived from the compound represented by the formula (C) can be incorporated.
- * represents a binding moiety.
- R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, or a cycloalkyl having 5 to 20 carbon atoms. Selected from the group consisting of a group, a C 5-20 cycloalkoxyl group, a C 6-20 aryl group, or a 6-20 aryloxy group.
- R 1 and R 2 in formula (A) ⁇ (C) are respectively the same as R 1 and R 2 in the formula (1).
- R 1 and R 2 are hydrogen atoms (9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene; BPEF; a compound of the following formula (1) -1 )
- BPEF a compound of the following formula (1) -1
- the corresponding compounds of the formulas (A) -1 to (C) -1 are as follows.
- R 1 and R 2 are phenyl groups (for example, 9,9-bis (4- (2-hydroxyethoxy) -3-phenylphenyl) fluorene; BPPEF; the following formula (1) ) -2) and the corresponding compounds of the formulas (A) -2 to (C) -2 are as follows.
- the dihydroxy component in addition to the compound represented by the formula (1), other dihydroxy compounds can be used in combination.
- the dihydroxy compound is at least one selected from the group consisting of a dihydroxy compound represented by formula (2) and a compound represented by formula (3) in addition to the dihydroxy compound represented by formula (1). Further comprising a dihydroxy compound.
- the thermoplastic resin obtained by using such a dihydroxy compound as a raw material is represented by the formula (2) in addition to the structural unit (1) ′ derived from the dihydroxy compound represented by the formula (1). It further contains at least one of the structural unit (2) ′ derived from the dihydroxy compound and the structural unit (3) ′ derived from the dihydroxy compound represented by the formula (3).
- * represents a bonding part.
- the functional group contributing to polycondensation is an alcoholic hydroxyl group.
- the structural unit (2) ′ derived from the compound represented by the formula (2) contributes to a high refractive index and has an Abbe number higher than that of the structural unit (1) ′ derived from the compound represented by the formula (1). Contributes to reduction.
- the structural unit (1) ′ and the structural unit (2) ′ there is an effect of reducing the birefringence value of the entire resin and reducing the optical distortion of the optical molded body.
- the total amount of the dihydroxy compound of the formula (1) and the dihydroxy compound of the formula (2) is preferably 50 mol% or more, more preferably 80 mol% or more with respect to 100 mol% of the dihydroxy compound used as a raw material for the thermoplastic resin. Is preferable, 90 mol% or more is particularly preferable, and 100 mol% is most preferable.
- the molar ratio of the dihydroxy compound of the formula (1) and the dihydroxy compound of the formula (2) (the structural unit (1) ′ and the structural unit (2) ′) is preferably 20/80 to 80/20, more preferably 30/70 to 80 / 20 is more preferable, and 40/60 to 80/20 is particularly preferable.
- each X is independently an alkylene group having 1 to 4 carbon atoms.
- Preferred examples of the alkylene group having 1 to 4 carbon atoms include methylene group, ethylene group, propylene group, isopropylene group, n-butylene group, isobutylene group, sec-butylene group, and tert-butylene group.
- X is preferably an ethylene group because the melt fluidity of the resin during molding becomes good.
- Examples of the dihydroxy compound represented by the formula (2) include 2,2′-bis (1-hydroxymethoxy) -1,1′-binaphthalene, 2,2′-bis (2-hydroxyethoxy) -1,1.
- Examples include '-binaphthalene, 2,2'-bis (3-hydroxypropyloxy) -1,1'-binaphthalene, 2,2'-bis (4-hydroxybutoxy) -1,1'-binaphthalene, and the like. Of these, 2,2'-bis (2-hydroxyethoxy) -1,1'-binaphthalene is preferable. These may be used alone or in combination of two or more.
- thermoplastic resin has a structural unit (2) ′ derived from the compound represented by the formula (2).
- the functional group contributing to polycondensation is an alcoholic hydroxyl group or a phenolic hydroxyl group.
- the structural unit (3) ′ derived from the compound represented by the formula (3) contributes to a high refractive index and has a smaller Abbe number than the structural unit (A) derived from the compound represented by the formula (1). Contribute to.
- the structural unit (A) and the structural unit (C) there is an effect of reducing the birefringence value of the entire resin and reducing the optical distortion of the optical molded body.
- the total amount of the dihydroxy compound of the formula (1) and the dihydroxy compound of the formula (3) is preferably 50 mol% or more, more preferably 80 mol% or more with respect to 100 mol% of the dihydroxy compound used as a raw material for the thermoplastic resin. Is preferable, 90 mol% or more is particularly preferable, and 100 mol% is most preferable.
- the molar ratio of the dihydroxy compound of formula (1) and the dihydroxy compound of formula (3) (structural unit (1) ′ to structural unit (3) ′) is preferably 20/80 to 99/1, preferably 30/70 to 95. / 5 is more preferable, and 40/60 to 90/10 is particularly preferable.
- R 6 and R 7 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, or a carbon number of 5 It is selected from the group consisting of ⁇ 20 cycloalkoxyl groups, C 6-20 aryl groups or C 6-20 aryloxy groups, and halogen atoms (F, Cl, Br, I). Of these, a hydrogen atom and a methyl group are preferable from the viewpoints of few impurities and a large amount of circulation.
- Z 1 and Z 2 are each independently selected from the group consisting of an alkylene group having 1 to 8 carbon atoms, a cycloalkylene group having 6 to 10 carbon atoms, and an arylene group having 6 to 10 carbon atoms.
- a cycloalkylene group having 6 carbon atoms and an arylene group having 6 carbon atoms are preferable in terms of excellent heat resistance.
- l 1 and l 2 are each independently an integer of 0 to 5. Above all, since it is excellent in heat resistance, it is preferable l 1 and l 2 are 0.
- Q is a single bond or Selected from the group consisting of
- R 8 , R 9 , R 14 to R 17 are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, and a phenyl group;
- R 10 to R 13 each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms;
- Z ′ is an integer from 3 to 11;
- R 6 and R 7 may be the same or different.
- dihydroxy compounds represented by formula (3) include, for example, 4,4-bis (4-hydroxyphenyl) propane (ie, bisphenol A), 1,1-bis (4-hydroxyphenyl) -1-phenyl Ethane (ie, bisphenol AP), 2,2-bis (4-hydroxyphenyl) hexafluoropropane (ie, bisphenol AF), 2,2-bis (4-hydroxyphenyl) butane (ie, bisphenol B), bis ( 4-hydroxyphenyl) diphenylmethane (ie bisphenol BP), bis (4-hydroxy-3-methylphenyl) propane (ie bisphenol C), 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane 2,2-bis (4-hydroxy-3,5-di- Tilphenyl) propane, 2,2-bis (4-hydroxy- (3,5-diphenyl) phenyl) propane, 2,2-bis (4-hydroxy-3,5-dibromophenyl) propane, 1,1-bis ( 4-hydroxyphenyl) ethane (ie
- thermoplastic resin has a structural unit (3) ′ derived from the compound represented by the formula (3).
- the thermoplastic resin may contain a structural unit derived from a dihydroxy compound other than the compounds of the above formulas (1) to (3).
- Other dihydroxy compounds include tricyclodecane [5.2.1.0 2,6 ] dimethanol, pentacyclopentadecanedimethanol, cyclohexane-1,2-dimethanol, cyclohexane-1,4-dimethanol, cyclohexane -1,3-dimethanol, decalin-2,6-dimethanol, decalin-2,3-dimethanol, decalin-1,5-dimethanol, 2,3-norbornane dimethanol, 2,5-norbornane dimethanol Alicyclic dihydroxy compounds such as 1,3-adamantane dimethanol; ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,3-butanediol, 1,2 -Butanediol, 1,5
- dihydroxy compounds are preferably added in an amount of 20 mol% or less, more preferably 10 mol% or less, relative to 100 mol% of the compound of formula (1). Within this range, a high refractive index is maintained.
- thermoplastic resin is derived from the resin composed of the structural unit (1) ′ derived from the dihydroxy compound of the formula (1) (first embodiment); derived from the dihydroxy compound of the formula (1).
- a resin comprising the structural unit (1) ′ and the structural unit (2) ′ derived from the dihydroxy compound of the formula (2) (second embodiment); the structural unit (1) ′ derived from the dihydroxy compound of the formula (1) and Resin comprising the structural unit (3) ′ derived from the dihydroxy compound of the formula (3) (third embodiment); the structural unit (1) ′ derived from the dihydroxy compound of the formula (1), and the dihydroxy compound of the formula (2) Resin (fourth embodiment) comprising the structural unit (2) ′ derived from and the structural unit (3) ′ derived from the dihydroxy compound represented by formula (3); or the structural unit derived from the dihydroxy compound represented by formula (1) (1 ) 'And Te Is preferably at least one dicarboxylic acid or a resin consisting of structural units derived from a derivative thereof selected from phthalic acid dimethyl or
- thermoplastic resins (polycarbonate resin, polyester resin, polyester carbonate resin) of the first to fifth embodiments may be used as a mixture or may be used as a mixture with other resins.
- Comprising the structural unit (1) ′ and optionally the structural unit ⁇ ( ⁇ (2) ′ and / or (3) ′).
- the polycarbonate binding moiety is derived from a carbonate precursor such as phosgene or carbonic acid diester.
- thermoplastic resins according to the first to fifth aspects include, as trace components, the structural unit (A) ′ derived from the dihydroxy compound of the above formula (A) and the structural unit derived from the dihydroxy compound of the above formula (B). (B) ′ and at least one of the structural unit (C) ′ derived from the dihydroxy compound of the above formula (C) may be included.
- the thermoplastic resin of the first to fourth aspects is a polycarbonate resin.
- thermoplastic resin of the fifth aspect is a polyester carbonate resin.
- the preferred weight average molecular weight of the thermoplastic resin is 10,000 to 100,000.
- the weight average molecular weight (Mw) of a thermoplastic resin means the polystyrene conversion weight average molecular weight, and is measured by the method as described in the Example mentioned later. If Mw is 10,000 or more, the brittle fall of a molded object is prevented. If Mw is 100,000 or less, the melt viscosity does not become too high, the resin can be easily taken out from the mold during molding, and the fluidity is good, which is suitable for injection molding in a molten state. More preferably, the weight average molecular weight (Mw) is 20,000 to 70,000, still more preferably 25,000 to 60,000.
- the preferred glass transition temperature (Tg) is 95 to 180 ° C, more preferably 110 to 170 ° C, still more preferably 115 to 160 ° C, and particularly preferably 125. ⁇ 145 ° C.
- Tg is lower than 95 ° C.
- the melting temperature of the resin becomes high and the resin is likely to be decomposed or colored, which is not preferable.
- the glass transition temperature of resin is too high, in a general-purpose mold temperature controller, the difference between the mold temperature and the resin glass transition temperature becomes large. Therefore, in applications where strict surface accuracy is required for products, it is difficult and undesirable to use a resin having a glass transition temperature that is too high.
- the thermoplastic resin preferably has a 5% weight loss temperature (Td) of 350 ° C. or higher measured at a temperature rising rate of 10 ° C./min as an index of thermal stability to withstand heating during injection molding.
- Td 5% weight loss temperature
- the thermal decomposition during the molding is severe and it becomes difficult to obtain a good molded product, which is not preferable.
- the thermoplastic resin may have any structure of random, block and alternating copolymer.
- thermoplastic resin phenol produced during production and carbonic diester remaining without reacting exist as impurities.
- the phenol content in the thermoplastic resin is preferably 0.1 to 3000 ppm, more preferably 0.1 to 2000 ppm, 1 to 1000 ppm, 1 to 800 ppm, 1 to 500 ppm, or 1 to 300 ppm. It is particularly preferred.
- the content of carbonic acid diester in the polycarbonate resin or polyester carbonate resin is preferably 0.1 to 1000 ppm, more preferably 0.1 to 500 ppm, and particularly preferably 1 to 100 ppm.
- the thermoplastic resin according to the embodiment has as little foreign matter content as possible, and it is preferable to perform filtration of the molten raw material, filtration of the catalyst solution, and filtration of the molten oligomer.
- the filter mesh is preferably 7 ⁇ m or less, more preferably 5 ⁇ m or less.
- the mesh of the polymer filter is preferably 100 ⁇ m or less, more preferably 30 ⁇ m or less.
- the step of collecting the resin pellets must be a low dust environment, and is preferably class 6 or less, more preferably class 5 or less.
- polyester resin can also be used with reference to the following description (polycarbonate resin) and / or using a known method.
- the polycarbonate resin according to the embodiment includes a structural unit (1) ′ derived from the compound represented by the formula (1), a structural unit (A) ′ derived from the dihydroxy compound of the formula (A) as a trace component, At least one of the structural unit (B) ′ derived from the dihydroxy compound of the above formula (B) and the structural unit (C) ′ derived from the dihydroxy compound of the above formula (C), and the above-described other units as necessary.
- Polycarbonate resin containing a structural unit for example, structural unit (2) ′ and / or (3) ′.
- the polycarbonate binding moiety is derived from a carbonate precursor such as phosgene or a carbonic acid diester.
- the polycarbonate resin is produced by reacting a dihydroxy compound with a carbonate precursor such as a carbonic acid diester.
- a carbonate precursor such as a carbonic acid diester.
- each structural unit is bonded through a carbonate bond.
- the reactant further comprises a carbonic acid diester in addition to the dihydroxy compound.
- the dihydroxy compound containing the compound represented by the above formula (1), the dihydroxy compound of the above formula (A) as a trace component, the dihydroxy compound of the above formula (B), and the dihydroxy compound of the above formula (C) At least one of the compounds, optionally a compound represented by the above formula (2) and / or (3), and a carbonate precursor such as a carbonic acid diester are reacted in the presence or absence of a transesterification catalyst.
- the reaction method include various methods such as a melt polycondensation method such as a transesterification method and a direct polymerization method, a solution polymerization method, and an interfacial polymerization method. Among them, a melt polycondensation method that does not use a reaction solvent is preferable.
- Examples of the carbonic acid diester include diphenyl carbonate, ditolyl carbonate, bis (chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, and dicyclohexyl carbonate. Of these, diphenyl carbonate is particularly preferred.
- the carbonic acid diester (for example, diphenyl carbonate) is preferably used in a ratio of 0.97 to 1.20 mol, more preferably 0.98 to 1.10 mol, relative to a total of 1 mol of the dihydroxy compound. .
- An example of the production method is a method in which a dihydroxy compound component is heated and stirred with a carbonic acid diester and melted in an inert gas atmosphere, and then polymerized while distilling off the alcohol or phenols produced.
- the reaction temperature varies depending on the boiling point of the alcohol or phenol produced, but is usually in the range of 120 to 350 ° C.
- the reaction is decompressed from the beginning, and the reaction is completed while distilling off the produced alcohol or phenol.
- a transesterification catalyst can also be used to accelerate the reaction.
- the reaction may be carried out continuously or batchwise.
- the reaction equipment used for the reaction is a horizontal type equipped with paddle blades, lattice blades, glasses blades, etc., even if it is a vertical type equipped with vertical stirring blades, Max blend stirring blades, helical ribbon type stirring blades, etc. Or an extruder type equipped with a screw. Further, it is preferable to use a reaction apparatus in which these reaction apparatuses are appropriately combined in consideration of the viscosity of the polymer.
- a basic compound catalyst is used as the transesterification catalyst.
- examples thereof include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds.
- alkali metal compound examples include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, and alkoxides of alkali metals.
- alkaline earth metal compound examples include organic acid salts, inorganic salts, oxides, hydroxides, hydrides or alkoxides of alkaline earth metal compounds.
- magnesium hydroxide, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenyl phosphate and the like are used.
- nitrogen-containing compound examples include quaternary ammonium hydroxide and salts thereof, amines and the like.
- quaternary ammonium hydroxides having an alkyl group, an aryl group, and the like such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, and trimethylbenzylammonium hydroxide;
- Tertiary amines such as triethylamine, dimethylbenzylamine and triphenylamine; secondary amines such as diethylamine and dibutylamine; primary amines such as propylamine and butylamine; 2-methylimidazole, 2-phenylimidazole and benzimidazole Imidazoles such as ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, te
- salts of zinc, tin, zirconium, lead, etc. may be used, and these can be used alone or in combination.
- transesterification catalysts include zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin (II) chloride, tin (IV) chloride, tin (II) acetate, tin (IV) acetate, Examples include dibutyltin dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead (II) acetate, and lead (IV) acetate.
- transesterification catalysts are used in a ratio of 1 ⁇ 10 ⁇ 9 to ⁇ 10 ⁇ 3 mol, preferably 1 ⁇ 10 ⁇ 7 to 1 ⁇ 10 ⁇ 4 mol, relative to a total of 1 mol of the dihydroxy compound. It is done.
- catalysts Two or more types may be used in combination. Further, the catalyst itself may be added as it is, or it may be added after being dissolved in a solvent such as water or phenol.
- the melt polycondensation method is a method in which melt polycondensation is carried out using the above-mentioned raw materials and catalysts under heating and further under normal pressure or reduced pressure while removing by-products by transesterification.
- the catalyst may be present together with the raw materials from the beginning of the reaction, or may be added during the reaction.
- the catalyst may be removed or deactivated after the polymerization reaction to maintain thermal stability and hydrolysis stability, but it is not always necessary to deactivate.
- a method for deactivation of the catalyst by adding a known acidic substance can be preferably carried out.
- the acidic substance include esters such as butyl benzoate; aromatic sulfonic acids such as p-toluenesulfonic acid; aromatic sulfonic acid esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate.
- Phosphoric acids such as phosphorous acid, phosphoric acid, phosphonic acid; triphenyl phosphite, monophenyl phosphite, diphenyl phosphite, diethyl phosphite, di-n-propyl phosphite, diphosphorous acid Phosphorous esters such as n-butyl, di-n-hexyl phosphite, dioctyl phosphite, monooctyl phosphite; triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate, phosphoric acid Phosphate esters such as dioctyl and monooctyl phosphate; Phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid and dibutylphosphonic acid Phosphonates such as diethyl phenylphosphonate; pho
- p-toluene or butyl sulfonate is particularly preferable.
- These deactivators are used in an amount of 0.01 to 50 times mol, preferably 0.3 to 20 times mol for the amount of catalyst. When the amount is less than 0.01 times the amount of the catalyst, the deactivation effect is insufficient, which is not preferable. Moreover, when it is more than 50 times mole with respect to the amount of catalyst, since the heat resistance of resin falls and it becomes easy to color a molded object, it is unpreferable.
- the kneading of the deactivator may be performed immediately after the completion of the polymerization reaction, or may be performed after pelletizing the polymerized resin.
- other additives antioxidants, mold release agents, ultraviolet absorbers, fluidity modifiers, crystal nucleating agents, reinforcing agents, dyes, antistatic agents, antibacterial agents, etc. described later. Can also be added in a similar manner.
- the temperature during devolatilization is preferably 230 to 300 ° C, more preferably 250 to 270 ° C.
- a horizontal apparatus equipped with a stirring blade having excellent surface renewability, such as a paddle blade, a lattice blade, or a glasses blade, or a thin film evaporator is preferably used.
- the polyester carbonate resin according to the embodiment includes the structural unit (1) ′ derived from the compound represented by the formula (1); the structural unit (A) ′ derived from the dihydroxy compound of the formula (A) as a trace component. , At least one of the structural unit (B) ′ derived from the dihydroxy compound of the formula (B) and the structural unit (C) ′ derived from the dihydroxy compound of the formula (C); derived from a dicarboxylic acid or a derivative thereof
- the structural unit; and other structural units described above, if necessary, are bonded via a carbonate bond and an ester bond.
- the polyester carbonate resin of one embodiment is produced by reacting a dihydroxy compound, a dicarboxylic acid or a derivative thereof, and a carbonate precursor such as a carbonic acid diester. Therefore, in one embodiment, the reactant includes a compound represented by the above formula (1), a dihydroxy compound of the above formula (A) as a trace component, a dihydroxy compound of the above formula (B), and the above formula (C). ), A dihydroxy compound optionally containing a compound represented by the above formula (2) and / or (3), a dicarboxylic acid or a derivative thereof, and a carbonate precursor.
- the reaction method include various methods such as a melt polycondensation method such as a transesterification method and a direct polymerization method, a solution polymerization method, and an interfacial polymerization method. Among them, a melt polycondensation method that does not use a reaction solvent is preferable.
- the dicarboxylic acid component is not particularly limited, but naphthalenedicarboxylic acid (for example, 2,7-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, 1, 4-naphthalenedicarboxylic acid), terephthalic acid, isophthalic acid, phthalic acid, 2-methylterephthalic acid, biphenyldicarboxylic acid, tetralindicarboxylic acid, fluorene-9,9-dipropionic acid and other aromatic dicarboxylic acids, oxalic acid, malon Acid, succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, dodecanedicarboxylic acid, cyclohex
- dicarboxylic acid derivatives include esters (eg, C 1-4 alkyl esters), acid anhydrides, and acid halides.
- dicarboxylic acids containing at least one selected from terephthalic acid, 2,6-naphthalenedicarboxylic acid and fluorene-9,9-dipropionic acid or derivatives thereof are from the viewpoint of market distribution, heat resistance, and refractive index.
- At least one selected from dimethyl terephthalate, dimethyl 2,6-naphthalenedicarboxylate and dimethyl fluorene-9,9-dipropionate is more preferable.
- the structure of dimethyl fluorene-9,9-dipropionate is shown below.
- the total amount of dimethyl terephthalate, dimethyl 2,6-naphthalenedicarboxylate and dimethyl fluorene-9,9-dipropionate is preferably 80 mol% or more with respect to 100 mol% of the dicarboxylic acid component. Preferably it is 90 mol% or more, More preferably, it is 95 mol% or more.
- the molar ratio (dihydroxy compound / dicarboxylic acid or derivative thereof) to the total of dicarboxylic acid components (dicarboxylic acid or derivative thereof) of the dihydroxy compound is preferably 20/80 to 95/5, and preferably 50/50 to 90/20. More preferred is 60/40 to 85/15. In such a case, a resin containing a structural unit derived from a dihydroxy compound and a structural unit derived from a dicarboxylic acid in the above ratio is obtained.
- Examples of the carbonic acid diester include diphenyl carbonate, ditolyl carbonate, bis (chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, and dicyclohexyl carbonate. Of these, diphenyl carbonate is particularly preferred.
- the carbonic acid diester (for example, diphenyl carbonate) is preferably used in a ratio of 0.97 to 1.20 mol, more preferably 0.98 to 1.10 mol, relative to a total of 1 mol of the dihydroxy compound. .
- a basic compound catalyst is used as the transesterification catalyst.
- examples thereof include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds.
- alkali metal compound examples include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, and alkoxides of alkali metals.
- alkaline earth metal compound examples include organic acid salts, inorganic salts, oxides, hydroxides, hydrides or alkoxides of alkaline earth metal compounds.
- magnesium hydroxide, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenyl phosphate and the like are used.
- nitrogen-containing compound examples include quaternary ammonium hydroxide and salts thereof, amines and the like.
- quaternary ammonium hydroxides having an alkyl group, an aryl group, and the like such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, and trimethylbenzylammonium hydroxide;
- Tertiary amines such as triethylamine, dimethylbenzylamine and triphenylamine; secondary amines such as diethylamine and dibutylamine; primary amines such as propylamine and butylamine; 2-methylimidazole, 2-phenylimidazole and benzimidazole Imidazoles such as ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, te
- transesterification catalysts salts such as zinc, tin, zirconium, lead, titanium, germanium, antimony, osmium, and aluminum may be used, and these may be used alone or in combination.
- transesterification catalysts are used in a ratio of 1 ⁇ 10 ⁇ 9 to ⁇ 10 ⁇ 3 mol, preferably 1 ⁇ 10 ⁇ 7 to 1 ⁇ 10 ⁇ 4 mol, relative to a total of 1 mol of the dihydroxy compound. It is done.
- the catalyst itself may be added as it is, or it may be added after being dissolved in a solvent such as water or phenol.
- melt polycondensation is carried out using the above-mentioned raw materials and catalyst under heating and further under normal pressure or reduced pressure while removing by-products by transesterification. That is, it is preferable that the reaction temperature is started from ordinary temperature and normal pressure, and gradually raised to a reduced pressure while removing by-products.
- the catalyst may be present together with the raw materials from the beginning of the reaction, or may be added during the reaction. After completion of the polymerization reaction, the catalyst may be removed or deactivated in order to maintain thermal stability and hydrolysis stability, but it is not always necessary to deactivate. In the case of deactivation, the method described in the production of the polycarbonate resin can be preferably used as well.
- thermoplastic resin an antioxidant, a processing stabilizer, a light stabilizer, a polymerized metal deactivator, a flame retardant, a lubricant, an antistatic agent, a surfactant, an antibacterial agent, as long as the characteristics of the present invention are not impaired.
- Additives such as mold release agents, ultraviolet absorbers, plasticizers and compatibilizers may be added.
- Antioxidants include triethylene glycol-bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol-bis [3- (3,5-di- -Tert-butyl-4-hydroxyphenyl) propionate], pentaerythritol-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5-di- tert-butyl-4-hydroxyphenyl) propionate, 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, N, N-hexamethylene Bis (3,5-di-tert-butyl-4-hydroxy-hydrocinnamide), 3,5-di-te t-butyl-4-hydroxy-benzylphosphonate-diethy
- processing stabilizers include phosphorus processing heat stabilizers and sulfur processing heat stabilizers.
- the phosphorus processing heat stabilizer include phosphorous acid, phosphoric acid, phosphonous acid, phosphonic acid, and esters thereof.
- triphenyl phosphite tris (nonylphenyl) phosphite, tris (2,4-di-tert-butylphenyl) phosphite, tris (2,6-di-tert-butylphenyl) phosphite, Tridecyl phosphite, trioctyl phosphite, trioctadecyl phosphite, didecyl monophenyl phosphite, dioctyl monophenyl phosphite, diisopropyl monophenyl phosphite, monobutyl diphenyl phosphite, monodecyl dipheny
- Sulfur-based processing heat stabilizers include pentaerythritol-tetrakis (3-laurylthiopropionate), pentaerythritol-tetrakis (3-myristylthiopropionate), pentaerythritol-tetrakis (3-stearylthiopropionate) Dilauryl-3,3′-thiodipropionate, dimyristyl-3,3′-thiodipropionate, distearyl-3,3′-thiodipropionate, and the like.
- the content of the sulfur-based processing heat stabilizer is preferably 0.001 to 0.2 parts by weight with respect to 100 parts by weight of the thermoplastic resin.
- esters of alcohol and fatty acid include esters of monohydric alcohol and fatty acid, partial esters or total esters of polyhydric alcohol and fatty acid.
- the ester of the monohydric alcohol and the fatty acid is preferably an ester of a monohydric alcohol having 1 to 20 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms.
- the partial ester or total ester of a polyhydric alcohol and a fatty acid is preferably a partial ester or total ester of a polyhydric alcohol having 1 to 25 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms.
- examples of the ester of a monohydric alcohol and a saturated fatty acid include stearyl stearate, palmityl palmitate, butyl stearate, methyl laurate, isopropyl palmitate and the like.
- Examples of partial esters or total esters of polyhydric alcohols and saturated fatty acids include stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbate, behenic acid monoglyceride, capric acid monoglyceride, lauric acid monoglyceride, pentaerythritol monostearate.
- Dipentaerythritol such as rate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, 2-ethylhexyl stearate, dipentaerythritol hexastearate And all esters or partial esters.
- stearic acid monoglyceride and lauric acid monoglyceride are particularly preferred.
- the content of these release agents is preferably in the range of 0.005 to 2.0 parts by weight, more preferably in the range of 0.01 to 0.6 parts by weight, with respect to 100 parts by weight of the thermoplastic resin. A range of ⁇ 0.5 parts by weight is more preferred.
- the ultraviolet absorber at least one ultraviolet ray selected from the group consisting of a benzotriazole ultraviolet absorber, a benzophenone ultraviolet absorber, a triazine ultraviolet absorber, a cyclic imino ester ultraviolet absorber, and a cyanoacrylate ultraviolet absorber.
- Absorbents are preferred. That is, any of the ultraviolet absorbers listed below may be used alone or in combination of two or more.
- benzotriazole ultraviolet absorber examples include 2- (2-hydroxy-5-methylphenyl) benzotriazole, 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, 2- (2-hydroxy- 3,5-dicumylphenyl) phenylbenzotriazole, 2- (2-hydroxy-3-tert-butyl-5-methylphenyl) -5-chlorobenzotriazole, 2,2′-methylenebis [4- (1,1 , 3,3-tetramethylbutyl) -6- (2N-benzotriazol-2-yl) phenol], 2- (2-hydroxy-3,5-di-tert-butylphenyl) benzotriazole, 2- ( 2-hydroxy-3,5-di-tert-butylphenyl) -5-chlorobenzotriazole, 2- (2-hydroxy -3,5-di-tert-amylphenyl) benzotriazole, 2- (2-hydroxy-5-tert-octyl
- benzophenone ultraviolet absorbers examples include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone, 2-hydroxy-4- Methoxy-5-sulfoxybenzophenone, 2-hydroxy-4-methoxy-5-sulfoxytrihydridolate benzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy-5-sodiumsulfoxybenzophenone, bis (5-benzoyl-4-hydroxy-2- Methoxyphenyl) Down, 2-hydroxy -4-n-dodecyloxy benzophenone, 2-hydroxy-4-methoxy-2'-carboxy benzophenone.
- triazine ultraviolet absorbers examples include 2- (4,6-diphenyl-1,3,5-triazin-2-yl) -5-[(hexyl) oxy] -phenol, 2- (4,6-bis ( 2,4-dimethylphenyl) -1,3,5-triazin-2-yl) -5-[(octyl) oxy] -phenol and the like.
- Cyclic imino ester UV absorbers include 2,2′-bis (3,1-benzoxazin-4-one), 2,2′-p-phenylenebis (3,1-benzoxazin-4-one) 2,2′-m-phenylenebis (3,1-benzoxazin-4-one), 2,2 ′-(4,4′-diphenylene) bis (3,1-benzoxazin-4-one), 2,2 '-(2,6-naphthalene) bis (3,1-benzoxazin-4-one), 2,2'-(1,5-naphthalene) bis (3,1-benzoxazin-4-one) ), 2,2 ′-(2-methyl-p-phenylene) bis (3,1-benzoxazin-4-one), 2,2 ′-(2-nitro-p-phenylene) bis (3,1- Benzoxazin-4-one) and 2,2 '-(2-chloro-p- Eniren) bis (3,1-benzoxazin-4-one
- Cyanoacrylate-based ultraviolet absorbers include 1,3-bis-[(2′-cyano-3 ′, 3′-diphenylacryloyl) oxy] -2,2-bis [(2-cyano-3,3-diphenyl). And acryloyl) oxy] methyl) propane and 1,3-bis-[(2-cyano-3,3-diphenylacryloyl) oxy] benzene.
- the content of the ultraviolet absorber is preferably 0.01 to 3.0 parts by weight, more preferably 0.02 to 1.0 parts by weight, and still more preferably 100 parts by weight of the thermoplastic resin. 0.05 to 0.8 part by weight. If it is the range of this compounding quantity, it is possible to provide sufficient weather resistance to a thermoplastic resin according to a use.
- thermoplastic resin of the present invention may be in the form of a resin composition containing a plurality of types of resins.
- the resin composition contains at least a thermoplastic resin containing 1 to 100% by weight of the repeating unit represented by the formula (1).
- Examples of other resins include the following: Polyethylene, polypropylene, polyvinyl chloride, polystyrene, (meth) acrylic resin, ABS resin, polyamide, polyacetal, polycarbonate (excluding constituent unit (1) '), polyphenylene ether, polyester (providing constituent unit (1)' ), Polyester carbonate (excluding the structural unit (1) ′), polyphenylene sulfide, polyimide, polyethersulfone, polyetheretherketone, fluororesin, cycloolefin polymer, ethylene / vinyl acetate copolymer Coalescence, epoxy resin, silicone resin, phenol resin, unsaturated polyester resin, polyurethane.
- the content of the other resin that may be contained is preferably 20 parts by mass or less, more preferably 10 parts by mass or less, with respect to the total mass of the thermoplastic resin including the structural unit derived from the dihydroxy compound of the above formula (1). . When there is too much content of other resin, compatibility will worsen and the transparency of a resin composition may fall.
- thermoplastic resin of the present invention preferably has a tensile strength of 70% or more, more preferably 80% or more.
- the tensile strength of the resin can be measured by the method described in Examples described later.
- the thermoplastic resin of the present invention further preferably melt volume rate at 260 ° C. (MVR) is 20 cm 3 / is preferably 10min or more at which, 25 cm 3 / 10min is more and more preferably 30 cm 3 / 10min or more .
- MVR melt volume rate
- a molded body (for example, an optical element) can be produced using the thermoplastic resin of the present invention.
- it is molded by an arbitrary method such as an injection molding method, a compression molding method, an extrusion molding method, or a solution casting method.
- the optical element manufactured using the thermoplastic resin or the molded body according to the embodiment is suitably used for an optical lens, a prism, and the like.
- Molded articles produced by these methods are used for various glazing applications, automobile lamp lenses, lamp covers, optical lenses, OHP sheets, nameplates, indicator lamps, and the like.
- the film manufactured by this method is suitably used as a placel substrate or a retardation film for flat panel display substrate applications.
- the placel substrate is used unstretched, but in order to use it as a retardation film, it is stretched and oriented in at least a uniaxial direction so as to have an optimal birefringence characteristic to form a retardation film.
- An optical lens can be produced using the thermoplastic resin or molded article of the present invention.
- Optical lenses manufactured using the thermoplastic resin according to the embodiments have a high refractive index and excellent heat resistance, and thus, conventionally, expensive high refractive glass lenses such as telescopes, binoculars, and television projectors have been used. It can be used in various fields and is extremely useful. If necessary, it is preferably used in the form of an aspheric lens. Since an aspherical lens can substantially eliminate spherical aberration with a single lens, there is no need to remove spherical aberration by combining a plurality of spherical lenses, which reduces weight and reduces production costs. It becomes possible. Therefore, the aspherical lens is particularly useful as a camera lens among optical lenses.
- the optical lens is molded by an arbitrary method such as an injection molding method, a compression molding method, or an injection compression molding method.
- an injection molding method such as an injection molding method, a compression molding method, or an injection compression molding method.
- the optical lens of the present invention When the optical lens of the present invention is manufactured by injection molding, it is preferable to mold it under conditions of a cylinder temperature of 230 to 270 ° C. and a mold temperature of 100 to 140 ° C. With these molding conditions, it has excellent physical properties as an optical lens, and also has a function of cutting the wavelength in the ultraviolet region. The effect can be prevented. On the contrary, when the resin composition of the present invention is used as an ultraviolet filter, it is very transparent, so that a clear photograph can be taken without deteriorating the image quality of the photograph taken.
- the resin of the embodiment since it has high fluidity, it can be an optical lens having a thin and small size and a complicated shape.
- the thickness of the central portion is 0.05 to 3.0 mm, more preferably 0.05 to 2.0 mm, and still more preferably 0.1 to 2.0 mm.
- the diameter is 1.0 mm to 20.0 mm, more preferably 1.0 to 10.0 mm, and still more preferably 3.0 to 10.0 mm.
- the surface of the optical lens of the present invention may be provided with a coating layer such as an antireflection layer or a hard coating layer as necessary.
- the antireflection layer may be a single layer or a multilayer, and may be organic or inorganic, but is preferably inorganic. Specific examples include oxides or fluorides such as silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, cerium oxide, magnesium oxide, and magnesium fluoride.
- the optical lens of the present invention may be molded by any method such as mold molding, cutting, polishing, laser processing, electric discharge machining, and edging. Furthermore, mold molding is more preferable.
- the molding environment In order to avoid the contamination of foreign matter into the optical lens as much as possible, the molding environment must naturally be a low dust environment, preferably class 6 or less, more preferably class 5 or less.
- An optical film can be produced using the thermoplastic resin or molded article of the present invention. Since the optical film manufactured using the thermoplastic resin according to the embodiment is excellent in transparency and heat resistance, it is suitably used for a film for a liquid crystal substrate, an optical memory card, and the like.
- sheet is generally a thin product whose thickness is small and flat instead of length and width, and “film” is extremely small compared to the length and width, and has a maximum thickness.
- sheet and film are not clearly distinguished, and both are used as the same meaning.
- the film formed from the thermoplastic resin of the present invention has good heat resistance and hue.
- the resin composition is dissolved in an organic solvent such as methylene chloride, tetrahydrofuran, dioxane, etc., and a casting film is formed.
- a gas barrier film and a solvent-resistant film are attached to both sides of the film, and it is suitably used as a film for liquid crystal displays such as a film for a liquid crystal substrate (a plastic substrate) or a retardation film together with a transparent conductive film and a polarizing plate. It can be advantageously used for tablets, smartphones, handy terminals, various display elements, and the like.
- MVR Melt volume rate
- BPEF (9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene): 20 mg of BPEF was dissolved in 10 ml of methanol to adjust 0.2 wt / vol%.
- the following compounds (1) -1, (A) -1, (B) -1 and (C) -1 were identified using LC-MS after filtering each material with a PTFE filter having a pore size of 0.20 ⁇ m. The purity was calculated from the ratio of the peak area of each compound to the total peak area. The analysis was performed under the following measurement conditions.
- ⁇ LC Waters Acquity UPLC Flow rate: 0.5ml / min Temperature: 60 ° C Detector: UV254nm Column: Waters BEII phenyl (diameter 2.1mm x length 100mm, particle diameter 1.7um) Eluent: A mixed solution of A; water, B; methanol was used. The changes in the mixing ratio over time are shown below.
- MS Waters MALDI-Synapt HDMS Mode: MS Scan range: 100-1500 / 0.3sec Ionization method: ESI (+) Resolution: 8500 (Vmode) Capillary voltage: 3kV Code voltage: 30V Trap collision energy: 5V Transfer collision energy: 5V Source temperature: 150 °C Desolvation temperature: 500 °C Injection volume: 2 ⁇ l Internal reference material (mass correction): Leucine Enkephalin, 0.5ng / ul Internal standard flow rate: 0.1ml / min
- BPPEF (9,9-bis (4- (2-hydroxyethoxy) -3-phenylphenyl) fluorene): 20 wt.
- BPPEF was dissolved in 10 ml of methanol to adjust 0.2 wt / vol%.
- the following compounds (1) -2, (A) -2, (B) -2 and (C) -2 were identified using LC-MS after filtering each material with a PTFE filter having a pore size of 0.20 ⁇ m. The purity was calculated from the ratio of the peak area of each compound to the total peak area. The analysis was performed in the same manner as the BPEF analysis conditions.
- the BPEF purity was 99.5%
- the (A) -1 content was 200 ppm
- the (B) -1 content was 200 ppm
- the (C) -1 content was 800 ppm.
- the results of analysis by LC-MS are shown in Tables 1 and 3.
- the BPPEF purity was 99.2%
- the (A) -2 content was 3000 ppm
- the (B) -2 content was 200 ppm
- the (C) -2 content was 200 ppm.
- the results of analysis by LC-MS are shown in Table 2.
- the BPPEF purity was 99.4%
- the (A) -2 content was 900 ppm
- the (B) -2 content was 200 ppm
- the (C) -2 content was 200 ppm.
- the results of analysis by LC-MS are shown in Table 2.
- BPEF-1 produced in Synthesis Example 1; 21.000 g (0.048 mol), diphenyl carbonate (hereinafter sometimes abbreviated as “DPC”); 10.675 g (0.050 mol) and sodium hydrogen carbonate as a catalyst was added in a glass 200 mL reaction vessel with a stirrer and a distiller, and 6 ⁇ mol / mol (sodium bicarbonate was added in the form of a 0.1 wt% aqueous solution with respect to BPEF). Was replaced under a nitrogen atmosphere and heated to 200 ° C. under 760 Torr.
- DPC diphenyl carbonate
- BPEF-1 20.360 g (0.046 mol), 2,2-bis (4-hydroxyphenyl) propane (BPA); 1.598 g (0.007 mol), diphenyl carbonate (DPC); 11.910 g ( 0.056 mol), and 6 ⁇ mol / mol of sodium bicarbonate as a catalyst
- sodium bicarbonate is the number of moles relative to the total of BPEF and BPA, and added in the form of a 0.1 wt% aqueous solution.
- the mixture was placed in a glass 200 mL reaction vessel equipped with a stirrer and a distiller, and the inside of the system was replaced with a nitrogen atmosphere and heated to 200 ° C. under 760 Torr.
- BPEF-1 19.983 g (0.046 mol), and 2,387 '(2,5'-bis (2-hydroxyethoxy) -1,1'-binaphthalene (hereinafter sometimes abbreviated as "BHEBN”) 0.033 mol), DPC; 17.321 g (0.081 mol), and sodium hydrogen carbonate as a catalyst at 6 ⁇ mol / mol (sodium hydrogen carbonate is the number of moles relative to the sum of BPEF and BHEBN, 0
- BHEBN 2,387 '(2,5'-bis (2-hydroxyethoxy) -1,1'-binaphthalene
- BPPEF-1 20.410 g (0.035 mol), and 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene (hereinafter sometimes abbreviated as “BHEBN”) 10.140 g ( 0.027 mol), DPC; 13.380 g (0.0625 mol), and 6 ⁇ mol / mol of sodium bicarbonate as a catalyst (sodium bicarbonate is the number of moles relative to the sum of BPEF and BHEBN, and 0 In a glass 200 mL reaction vessel equipped with a stirrer and a distiller, the inside of the system was replaced with a nitrogen atmosphere, and the mixture was heated to 200 ° C. under 760 Torr.
- BHEBN 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene
- Example 5 The reaction was performed in the same manner as in Example 4 except that BPPEF-2 obtained in Synthesis Example 4 was used. Table 2 shows the MVR and tensile strength of the obtained resin.
- Polyester carbonate resin >> ⁇ Example 6> BPEF-1 produced in Synthesis Example 1; 40.000 g (0.091 mol), dimethyl terephthalate (hereinafter sometimes abbreviated as “DMT”) 4.4000 g (0.023 mol), diphenyl carbonate (DPC) 15.630 g (0.073 mol) and 1 ⁇ 10 ⁇ 3 g of titanium butoxide as a catalyst were placed in a glass 200 mL reaction vessel equipped with a stirrer and a distiller, and the inside of the system was replaced with a nitrogen atmosphere. The mixture was heated to 190 ° C. and then stirred for 20 minutes under the same conditions.
- DMT dimethyl terephthalate
- DPC diphenyl carbonate
- BPEF-1 produced in Synthesis Example 1; 32.000 g (0.073 mol), dimethyl 2,6-naphthalenedicarboxylate (hereinafter sometimes abbreviated as “NDCM”) 4.4000 g (0.018 Mol), DPC; 12.500 g (0.058 mol) and titanium butoxide was changed to 1 ⁇ 10 ⁇ 3 g as a catalyst, and reacted in the same manner as in Example 6.
- Table 3 shows the MVR and tensile strength of the obtained resin.
- BPEF 9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene
- BPPEF 9,9-bis (4- (2-hydroxyethoxy) -3-phenylphenyl) fluorene
- BPA 2,2-bis ( 4-hydroxyphenyl) propane
- BHEBN 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene
- DMT dimethyl terephthalate
- NDCM dimethyl 2,6-naphthalenedicarboxylate
- the polycarbonate resins obtained in Examples 1 to 5 using raw materials containing compounds of the formulas (A) to (C) of 1,500 ppm or more have a high melt volume rate (MVR), And it turns out that tensile strength is high.
- Comparative Examples 1 to 3 in which the total content of the compounds of formulas (A) to (C) is less than 1,500 ppm are obtained in comparison with Examples 1 to 3 using dihydroxy compounds having the same structure. It is confirmed that the melt volume rate (MVR) of the resin is decreased (fluidity decrease) and the tensile strength is decreased.
- MVR melt volume rate
- the polyester carbonate resins obtained in Examples 6 to 7 using raw materials containing compounds of formulas (A) to (C) of 1,500 ppm or more have a high melt volume rate (MVR), and It can be seen that the tensile strength is high.
- Comparative Example 5 in which the total content of the compounds of formulas (A) to (C) is less than 1,500 ppm is compared with Example 6 using a dihydroxy compound and a comonomer having the same structure, and the resulting polyester carbonate resin. It was confirmed that the tensile strength of the steel was lowered.
- Total light transmittance and haze The total light transmittance and haze were measured according to JIS K-7361 and JIS K-7136 using a haze meter (manufactured by Murakami Color Research Laboratory, "HM-150"). It was measured.
- Refractive index A film having a thickness of 0.1 mm was measured by the method of JIS-K-7142 using an Abbe refractometer (23 ° C., wavelength 589 nm).
- ⁇ (nD-1) / (nF-nC) nD: Refractive index at a wavelength of 589 nm nC: Refractive index at a wavelength of 656 nm nF: Refractive index at a wavelength of 486 nm
- Example 8 BHEBN 6.20 kg (16.56 mol), BPEF-1 10.00 kg (22.80 mol), diphenyl carbonate (DPC) 8.67 kg (40.46 mol), sodium bicarbonate 1.98 ⁇
- the reaction was conducted in the same manner as in Example 3 except that 10 ⁇ 2 g (2.36 ⁇ 10 ⁇ 4 mol) and the reactor were changed to 50 L. After completion of the reaction, nitrogen was introduced into the reactor, and the produced polycarbonate resin was extracted while pelletizing.
- the obtained pellets were melt extruded at 280 ° C. using a 26 mm twin screw extruder and a T die.
- the extruded molten film was nipped between a first cooling roll made of silicon rubber having a diameter of 200 mm and a second cooling roll made of metal having a diameter of 200 mm subjected to mat processing (arithmetic average roughness of the surface: 3.2 ⁇ m).
- mat processing as 3.2 ⁇ metic average roughness of the surface: 3.2 ⁇ m.
- the film was cooled, and the film was passed through a metal third cooling roll having a mirror surface structure, and a single-sided mat film was formed while being taken up by a take-up roll.
- the temperature of the first cooling roll is set to 40 ° C.
- the temperature of the second cooling roll is set to 130 ° C.
- the temperature of the third cooling roll is set to 130 ° C.
- the speed of the cooling roll is adjusted.
- the average roughness was 3.0 ⁇ m.
- Example 9 BPEF-1; 14.99 kg (34.18 mol), 2,2-bis (4-hydroxyphenyl) propane; 1.18 kg (5.15 mol), DPC; 8.79 kg (41.02 mol), carbonic acid
- the reaction was conducted in the same manner as in Example 2 except that sodium hydride; 1.98 ⁇ 10 ⁇ 2 g (2.36 ⁇ 10 ⁇ 4 mol) and the reactor were changed to 50 L.
- the obtained pellets were molded in the same manner as in Example 8.
- Table 4 shows the evaluation results of the films obtained in Examples 8 and 9 and Comparative Example 6.
- the films (Examples 8 and 9) produced using the polycarbonate resin of the present invention are compared with the conventional bisphenol A-based polycarbonate resin (Comparative Example 6) having equivalent fluidity (MVR). It is confirmed that the haze is high, the transparency is excellent, and the low Abbe and the high refractive index are exhibited.
- an injection molded product in which an optical lens was prepared as an injection molded product was produced by the following method.
- the thin molded product forms a lens with a convex curvature radius of 5.73 mm, a concave curvature radius of 3.01 mm, a diameter of 4.5 mm, a lens portion diameter of 3 mm, and a lens center thickness of 0.20 mm.
- Ten molded products were produced at a resin temperature of 260 ° C., a mold temperature of Tg-5 ° C., and a holding pressure of 600 kgf / cm 2 using a ROBOSHOT S-2000i30A injection molding machine manufactured by FANUC CORPORATION.
- the obtained optical lens was evaluated by the following method.
- the obtained molded product was measured with a birefringence meter (manufactured by Oji Scientific Instruments; KOBRA (registered trademark) -CCD / X) and compared with the retardation value at the measurement wavelength of 650 nm at the center of the lens.
- a less than 20 is B
- 20 to less than 40 is B
- 40 to less than 60 is C
- 60 or more is D.
- Example 10 An injection molded product was prepared using the polycarbonate resin obtained in Example 1.
- Table 5 shows the results of birefringence evaluation and weld line evaluation of the obtained molded product.
- Example 11 An injection molded article was prepared using the polycarbonate resin obtained in Example 2.
- Table 5 shows the results of birefringence evaluation and weld line evaluation of the obtained molded product.
- Example 12 An injection molded product was prepared using the polycarbonate resin obtained in Example 3.
- Table 5 shows the results of birefringence evaluation and weld line evaluation of the obtained molded product.
- Example 13 An injection molded product was prepared using the polycarbonate resin obtained in Example 4.
- Table 5 shows the results of birefringence evaluation and weld line evaluation of the obtained molded product.
- Example 14 An injection molded product was prepared using the polycarbonate resin obtained in Example 5.
- Table 5 shows the results of birefringence evaluation and weld line evaluation of the obtained molded product.
- the optical lenses (Examples 10 to 14) produced using the polycarbonate resin of the present invention had low birefringence (evaluation of A or B). Furthermore, in the optical lens of the present invention, the weld line had a short length (evaluation of A or B) due to the good fluidity of the polycarbonate resin used for production.
- optical lenses (Comparative Examples 7 to 9) manufactured using the polycarbonate resins of Comparative Examples 1 to 3 having a total content of the compounds of the formulas (A) to (C) of less than 1,500 ppm are weld lines. The length of was long. Further, in the optical lens (Comparative Example 10) manufactured using the conventional bisphenol A-based polycarbonate resin having the same fluidity (MVR), the weld line evaluation was equivalent to the optical lenses of Examples 10 to 14. However, birefringence was large (D evaluation).
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Metal Extraction Processes (AREA)
- Arc Welding In General (AREA)
Abstract
Description
前記ジヒドロキシ化合物は、
下記式(1)で表されるジヒドロキシ化合物と、
下記式(A)で表される化合物、下記式(B)で表される化合物、および下記式(C)で表される化合物の少なくとも一つと、
を含み、
前記式(A)で表される化合物、式(B)で表される化合物、および式(C)で表される化合物の合計重量が、前記式(1)で表されるジヒドロキシ化合物の重量(100重量部)に対して、1,500ppm以上である、製造方法。
[2] 前記ジヒドロキシ化合物における前記式(A)で表される化合物の重量が、前記式(1)で表されるジヒドロキシ化合物の重量(100重量部)に対して、1,000ppm以上である、[1]に記載の製造方法。
[3] 前記ジヒドロキシ化合物における前記式(B)で表される化合物の重量が、前記式(1)で表されるジヒドロキシ化合物の重量(100重量部)に対して、200ppm以上である、[1]または[2]に記載の製造方法。
[4] 前記ジヒドロキシ化合物における前記式(C)で表される化合物の重量が、前記式(1)で表されるジヒドロキシ化合物の重量(100重量部)に対して、200ppm以上である、[1]~[3]のいずれかに記載の製造方法。
[5] 前記ジヒドロキシ化合物は、下記式(2)で表されるジヒドロキシ化合物および下記式(3)で表されるジヒドロキシ化合物からなる群から選択される少なくとも一つをさらに含有する、[1]~[4]のいずれかに記載の製造方法。
Z1およびZ2はそれぞれ独立に、炭素数1~8のアルキレン基、炭素数6~10のシクロアルキレン基、および炭素数6~10のアリーレン基からなる群から選択され;
l1およびl2はそれぞれ独立に、0~5の整数であり;
Qは単結合または
ここで、R8、R9、R14~R17はそれぞれ独立に、水素原子、炭素数1~10のアルキル基、およびフェニル基からなる群から選択され;
R10~R13はそれぞれ独立に、水素原子または炭素数1~5のアルキル基を表し;
Z’は3~11の整数であり;
R6とR7は同じでも異なっていても良い。)
[6] Xがエチレン基である[1]~[5]のいずれかに記載の製造方法。
[7] 前記熱可塑性樹脂はポリカーボネート樹脂、ポリエステル樹脂、およびポリエステルカーボネート樹脂からなる群から選択される、[1]~[6]のいずれかに記載の製造方法。
[8] 前記熱可塑性樹脂はポリカーボネート樹脂である、[7]に記載の製造方法。
[9] 前記反応物が、炭酸ジエステルをさらに含む、[1]~[8]のいずれかに記載の製造方法。
[10] 前記熱可塑性樹脂はポリエステルカーボネート樹脂であり、
前記反応物は、前記ジヒドロキシ化合物と、炭酸ジエステルと、テレフタル酸、2,6-ナフタレンジカルボン酸、およびフルオレン-9,9-ジプロピオン酸から選択される少なくとも一種を含むジカルボン酸またはその誘導体とを含み、
前記ジヒドロキシ化合物と前記ジカルボン酸またはその誘導体とのモル比は、(ジヒドロキシ化合物/ジカルボン酸またはその誘導体)は、20/80~95/5である、[7]に記載の製造方法。
[11] 引張強度が80%以上である[1]~[10]のいずれかに記載の製造方法。
[12] [1]~[11]のいずれかに記載の製造方法で得られた熱可塑性樹脂を成形する工程を含む、成形体の製造方法。
[13] [1]~[11]のいずれかに記載の製造方法で得られた熱可塑性樹脂または[12]に記載の製造方法で得られた成形体を用いることを特徴とする、光学材料の製造方法。
[14] [1]~[11]のいずれかに記載の製造方法で得られた熱可塑性樹脂または[12]に記載の製造方法で得られた成形体を用いることを特徴とする、光学レンズの製造方法。
[15] [1]~[11]のいずれかに記載の製造方法で得られた熱可塑性樹脂または[12]に記載の製造方法で得られた成形体を用いることを特徴とする、光学フィルムを製造方法。
・LC:Waters Acquity UPLC
流速:0.5ml/min
温度:60℃
検出器:UV254nm
カラム:Waters BEII phenyl(径2.1mm×長さ100mm、粒子径1.7um)
溶離液:A;水、B;メタノールの混合溶液を用いた。
混合比の計時変化を以下に示す。
B=60%(0-6min)
B=60-95%(6-10min)
B=95-100%(10-11min)
B=100%(11-12min)
・MS:Waters MALDI-Synapt HDMS
モード:MS
スキャン範囲:100-1500/0.3sec
イオン化法:ESI(+)
分解能:8500(Vmode)
Capillary 電圧:3kV
Code電圧:30V
Trap collisionエネルギー:5V
Transfer collisionエネルギー:5V
Source温度:150℃
Desolvation温度:500℃
注入量:2μl
内部標準物質(質量補正):Leucine Enkephalin、0.5ng/ul
内部標準流速:0.1ml/min
本発明の実施形態の製造方法により得られる熱可塑性樹脂は、式(1)で表されるジヒドロキシ化合物を含む反応物を反応させることにより製造され、式(1)で表されるジヒドロキシ化合物に由来する構成単位(1)’を含むものである。
本発明において、ジヒドロキシ成分としては、式(1)で表される化合物に加えて、その他のジヒドロキシ化合物を併用することができる。例えば、ジヒドロキシ化合物は、式(1)で表されるジヒドロキシ化合物に加えて、式(2)で表されるジヒドロキシ化合物および式(3)で表される化合物からなる群から選択される少なくとも一つのジヒドロキシ化合物をさらに含む。このようなジヒドロキシ化合物を原料として用いることで、得られる熱可塑性樹脂は、式(1)で表されるジヒドロキシ化合物に由来する構成単位(1)’に加えて、式(2)で表されるジヒドロキシ化合物に由来する構成単位(2)’および式(3)で表されるジヒドロキシ化合物に由来する構成単位(3)’の少なくとも一つをさらに含む。
R10~R13はそれぞれ独立に、水素原子または炭素数1~5のアルキル基を表し;
Z’は3~11の整数であり;
R6とR7とは同じでも異なっていても良い。
熱可塑性樹脂は、上記式(1)~(3)の化合物以外のジヒドロキシ化合物に由来する構成単位を含んでいてもよい。その他のジヒドロキシ化合物としては、トリシクロデカン[5.2.1.02,6]ジメタノール、ペンタシクロペンタデカンジメタノール、シクロヘキサン-1,2-ジメタノール、シクロヘキサン-1,4-ジメタノール、シクロヘキサン-1,3-ジメタノール、デカリン-2,6-ジメタノール、デカリン-2,3-ジメタノール、デカリン-1,5-ジメタノール、2,3-ノルボルナンジメタノール、2,5-ノルボルナンジメタノール、1,3-アダマンタンジメタノール等の脂環式ジヒドロキシ化合物;エチレングリコール、1,3-プロパンジオール、1,2-プロパンジオール、1,4-ブタンジオール、1,3-ブタンジオール、1,2-ブタンジオール、1,5-ペンタンジオール、1,6-ヘキサンジオール、1,5-ヘプタンジオール、1,8-オクタンジオール、1,9-ノナンジオール、1,10-デカンジオール、スピログリコール等の脂肪族ジヒドロキシ化合物が挙げられる。
なお、第1態様~第5態様の熱可塑性樹脂は、微量成分として、上記式(A)のジヒドロキシ化合物に由来する構成単位(A)’、上記式(B)のジヒドロキシ化合物に由来する構成単位(B)’、および上記式(C)のジヒドロキシ化合物に由来する構成単位(C)’の少なくとも一つを含みうる。
好ましい一実施形態において、第1態様~第4態様の熱可塑性樹脂はポリカーボネート樹脂である。
好ましい一実施形態において、第5態様の熱可塑性樹脂はポリエステルカーボネート樹脂である。
使用する場合、好ましいガラス転移温度(Tg)は95~180℃であり、より好ましくは110~170℃であり、さらに好ましくは115~160℃であり、特に好ましくは125~145℃である。Tgが95℃より低いと、使用温度範囲が狭くなるため好ましくない。また180℃を超えると、樹脂の溶融温度が高くなり、樹脂の分解や着色が発生しやすくなるため好ましくない。また、樹脂のガラス転移温度が高すぎる場合、汎用の金型温調機では、金型温度と樹脂ガラス転移温度の差が大きくなってしまう。そのため、製品に厳密な面精度が求められる用途においては、ガラス転移温度が高すぎる樹脂の使用は難しく、好ましくない。
実施形態に係るポリカーボネート樹脂は、上記式(1)で表される化合物に由来する構成単位(1)’、微量成分として、上記式(A)のジヒドロキシ化合物に由来する構成単位(A)’、上記式(B)のジヒドロキシ化合物に由来する構成単位(B)’、および上記式(C)のジヒドロキシ化合物に由来する構成単位(C)’の少なくとも一つ、ならびに必要に応じて上述したその他の構成単位(例えば構成単位(2)’および/または(3)’など)を含むポリカーボネート樹脂である。例えば、ポリカーボネート結合部分は、ホスゲンまたは炭酸ジエステルなどのカーボネート前駆物質に由来する。
ポリカーボネート樹脂は、ジヒドロキシ化合物を炭酸ジエステルなどのカーボネート前駆物質と反応させて生成され、ポリカーボネート樹脂において、各構成単位は、カーボネート結合を介して結合される。一実施形態は、反応物はジヒドロキシ化合物に加えて炭酸ジエステルをさらに含む。
実施形態に係るポリエステルカーボネート樹脂は、上記式(1)で表される化合物に由来する構成単位(1)’;微量成分として、上記式(A)のジヒドロキシ化合物に由来する構成単位(A)’、上記式(B)のジヒドロキシ化合物に由来する構成単位(B)’、および上記式(C)のジヒドロキシ化合物に由来する構成単位(C)’の少なくとも一つ;ジカルボン酸またはその誘導体に由来する構成単位;ならびに必要に応じて上述したその他の構成単位が、カーボネート結合およびエステル結合を介して結合される。
中でも、テレフタル酸、2,6-ナフタレンジカルボン酸およびフルオレン-9,9-ジプロピオン酸から選択される少なくとも一種を含むジカルボン酸またはその誘導体が市場での流通性、耐熱性、屈折率の観点から好ましく、テレフタル酸ジメチル、2,6-ナフタレンジカルボン酸ジメチルおよびフルオレン-9,9-ジプロピオン酸ジメチルから選択される少なくとも一種がより好ましく、2,6-ナフタレンジカルボン酸ジメチルおよびテレフタル酸ジメチルから選択される少なくとも一種がさらに好ましい。フルオレン-9,9-ジプロピオン酸ジメチルの構造を以下に示す。
その他のエステル交換触媒として、具体的には、酢酸亜鉛、安息香酸亜鉛、2-エチルヘキサン酸亜鉛、塩化スズ(II)、塩化スズ(IV)、酢酸スズ(II)、酢酸スズ(IV)、ジブチルスズジラウレート、ジブチルスズオキサイド、ジブチルスズジメトキシド、ジルコニウムアセチルアセトナート、オキシ酢酸ジルコニウム、ジルコニウムテトラブトキシド、酢酸鉛(II)、酢酸鉛(IV)、チタンテトラブトキシド(IV)、チタンテトライソプロポキシド(IV)、チタン(IV)=テトラキス(2-エチル-1-ヘキサノラート)、酸化チタン(IV)、トリス(2,4-ペンタジオネート)アルミニウム(III)等が挙げられる。
また、触媒自体をそのまま添加してもよく、あるいは、水やフェノール等の溶媒に溶解してから添加してもよい。
重合反応終了後、熱安定性および加水分解安定性を保持するために、触媒を除去もしくは失活させてもよいが、必ずしも失活させる必要はない。失活させる場合には、ポリカーボネート樹脂の製造において説明した方法を同様に好ましく使用することができる。
熱可塑性樹脂には、本発明の特性を損なわない範囲において、酸化防止剤、加工安定剤、光安定剤、重合金属不活性化剤、難燃剤、滑剤、帯電防止剤、界面活性剤、抗菌剤、離型剤、紫外線吸収剤、可塑剤、相溶化剤等の添加剤を添加してもよい。
ポリエチレン、ポリプロピレン、ポリ塩化ビニル、ポリスチレン、(メタ)クリル樹脂、ABS樹脂、ポリアミド、ポリアセタール、ポリカーボネート(ただし構成単位(1)’を含まないもの)、ポリフェニレンエーテル、ポリエステル(ただし構成単位(1)’を含まないもの)、ポリエステルカーボネート(ただし構成単位(1)’を含まないもの)、ポリフェニレンサルファイド、ポリイミド、ポリエーテルサルホン、ポリエーテルエーテルケトン、フッ素樹脂、シクロオレフィンポリマー、エチレン・酢酸ビニル共重合体、エポキシ樹脂、シリコーン樹脂、フェノール樹脂、不飽和ポリエステル樹脂、ポリウレタン。
と、相溶性が悪くなり、樹脂組成物の透明性が低下する場合がある。
本発明の熱可塑性樹脂は、引張強度が好ましくは70%以上であり、より好ましくは80%以上である。樹脂の引張強度は、後述する実施例に記載の方法で測定することができる。
本発明の熱可塑性樹脂を用いて成形体(例えば、光学素子)を製造できる。例えば射出成形法、圧縮成形法、押出成形法、溶液キャスティング法など任意の方法により成形される。実施形態に係る熱可塑性樹脂または成形体を用いて製造される光学素子は、光学レンズ、プリズム等に好適に使用される。
本発明の熱可塑性樹脂または成形体を用いて光学レンズを製造できる。実施形態に係る熱可塑性樹脂を用いて製造される光学レンズは、高屈折率であり、耐熱性に優れるため、望遠鏡、双眼鏡、テレビプロジェクター等、従来、高価な高屈折率ガラスレンズが用いられていた分野に用いることができ、極めて有用である。必要に応じて、非球面レンズの形で用いることが好ましい。非球面レンズは、1枚のレンズで球面収差を実質的にゼロとすることが可能であるため、複数の球面レンズの組み合わせによって球面収差を取り除く必要がなく、軽量化および生産コストの低減化が可能になる。従って、非球面レンズは、光学レンズの中でも特にカメラレンズとして有用である。
本発明の熱可塑性樹脂または成形体を用いて光学フィルムを製造できる。実施形態に係る熱可塑性樹脂を用いて製造される光学フィルムは、透明性および耐熱性に優れるため、液晶基板用フィルム、光メモリーカード等に好適に使用される。
ポリカーボネート樹脂およびポリエステルカーボネート樹脂の評価は以下の方法により行った。
(1)メルトボリュームレート(MVR):MVRは、樹脂または樹脂組成物の流動性を示す指標であり、値が大きいほど流動性が高いことを示す。得られたポリカーボネート樹脂を120℃で4時間真空乾燥し、(株)東洋精機製作所製メルトインデクサーT‐111を用い、温度260℃、加重2160gの条件下で測定した。
液体クロマトグラフ質量分析計(LC-MS)を用いて、下記の方法により、式(1)-1、式(1)-2、式(A)-1、式(A)-2、式(B)-1、式(B)-2、式(C)-1、式(C)-2で表される化合物の重量を測定した。
BPEF20mgをメタノール10mlに溶解して0.2wt/vol%を調整した。各資料を孔径0.20μmのPTFEフィルターで濾過した後にLC‐MSを用いて、下記(1)-1、(A)-1、(B)-1及び(C)-1の化合物を同定し、全ピーク面積に対する各化合物のピーク面積の割合から純度を算定した。分析は下記の測定条件で行った。
流速:0.5ml/min
温度:60℃
検出器:UV254nm
カラム:Waters BEII phenyl(径2.1mm×長さ100mm、粒子径1.7um)
溶離液:A;水、B;メタノールの混合溶液を用いた。
混合比の計時変化を以下に示す。
B=60%(0-6min)
B=60-95%(6-10min)
B=95-100%(10-11min)
B=100%(11-12min)
・MS:Waters MALDI-Synapt HDMS
モード:MS
スキャン範囲:100-1500/0.3sec
イオン化法:ESI(+)
分解能:8500(Vmode)
Capillary 電圧:3kV
Code電圧:30V
Trap collisionエネルギー:5V
Transfer collisionエネルギー:5V
Source温度:150℃
Desolvation温度:500℃
注入量:2μl
内部標準物質(質量補正):Leucine Enkephalin、0.5ng/ul
内部標準流速:0.1ml/min
BPPEF20mgをメタノール10mlに溶解して0.2wt/vol%を調整した。各資料を孔径0.20μmのPTFEフィルターで濾過した後にLC‐MSを用いて、下記(1)-2、(A)-2、(B)-2及び(C)-2の化合物を同定し、全ピーク面積に対する各化合物のピーク面積の割合から純度を算定した。分析は前記BPEFの分析条件と同様に行なった。
攪拌機、窒素吹込管、温度計および冷却管を付けた水分離器を備えたガラス製反応器にフルオレノン84.6g(0.47モル)、フェノキシエタノール394.2g(2.85モル)、トルエン350gおよび100℃で減圧乾燥し結晶水を除いたリンタングステン酸4.3gを加え、トルエン還流下、生成水を反応系外に除去しながら11時間攪拌した。この反応液にトルエン300gを加え、水100gを用いて80℃で水洗を行った。次いでこの液を室温まで徐々に冷却し、析出した結晶をろ過、乾燥することにより白色結晶[9,9-ビス(4-(2-ヒドロキシエトキシ)フェニル)フルオレン](BPEF‐1)を得た。LC-MSによる分析の結果、BPEF純度は98.6%、(A)-1含有量は6300ppm、(B)-1含有量は2300ppm、(C)-1含有量は3100ppmであった。LC-MSによる分析の結果を表1および表3に示す。
合成例1と同様にして得られた白色結晶[9,9-ビス(4-(2-ヒドロキシエトキシ)フェニル)フルオレン]200gへ、トルエン300gを添加し、水100gを用いて80℃での水洗を2回繰り返した。室温まで徐々に冷却し、析出した結晶をろ過、乾燥することにより白色結晶[9,9-ビス(4-(2-ヒドロキシエトキシ)フェニル)フルオレン](BPEF‐2)を得た。LC-MSによる分析の結果、BPEF純度は99.5%、(A)-1含有量は200ppm、(B)-1含有量は200ppm、(C)-1含有量は800ppmであった。LC-MSによる分析の結果を表1および表3に示す。
攪拌機、窒素吹込管、温度計および冷却管を付けた水分離器を備えたガラス製反応器にフルオレノン84.6g(0.47モル)、2-フェニルフェノルキシエタノール485.1g(2.85モル)、トルエン350gおよび100℃で減圧乾燥し結晶水を除いたリンタングステン酸4.3gを加え、トルエン還流下、生成水を反応系外に除去しながら11時間攪拌した。この反応液にトルエン300gを加え、水100gを用いて80℃で水洗を行った。次いでこの液を室温まで徐々に冷却し、析出した結晶をろ過、乾燥することにより白色結晶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(BPPEF‐1)を得た。LC-MSによる分析の結果、BPPEF純度は98.5%、(A)-2含有量は8900ppm、(B)-2含有量は600ppm、(C)-2含有量は800ppmであった。LC-MSによる分析の結果を表2に示す。
合成例3と同様にして得られた白色結晶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(BPPEF‐1)200gへ、トルエン300gを添加し、水100gを用いて80℃での水洗を2回繰り返した。室温まで徐々に冷却し、析出した結晶をろ過、乾燥することにより白色結晶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(BPPEF‐2)を得た。LC-MSによる分析の結果、BPPEF純度は99.2%、(A)-2含有量は3000ppm、(B)-2含有量は200ppm、(C)-2含有量は200ppmであった。LC-MSによる分析の結果を表2に示す。
合成例3と同様にして得られた白色結晶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(BPPEF‐1)200gへ、トルエン300gを添加し、水100gを用いて80℃での水洗を5回繰り返した。室温まで徐々に冷却し、析出した結晶をろ過、乾燥することにより白色結晶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(BPPEF‐3)を得た。LC-MSによる分析の結果、BPPEF純度は99.4%、(A)-2含有量は900ppm、(B)-2含有量は200ppm、(C)-2含有量は200ppmであった。LC-MSによる分析の結果を表2に示す。
<実施例1>
合成例1で製造したBPEF‐1;21.000g(0.048モル)、ジフェニルカーボネート(以下「DPC」と省略することがある);10.675g(0.050モル)及び触媒として炭酸水素ナトリウムを6μモル/モル(炭酸水素ナトリウムはBPEFに対してのモル数であり、0.1wt%水溶液の状態で添加した)とを攪拌器および留出装置付ガラス製200mL反応容器に入れ、系内を窒素雰囲気下に置換し、760Torrの下で200℃に加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で20分間攪拌した。引き続き、減圧度を200Torrに調整すると同時60℃/hrの速度で210℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。その後、20分間、210℃に保持し反応を行った。さらに180Torrに減圧しながら60℃/hrの速度で230℃まで昇温した。昇温終了10分後、温度を保持したままで150Torrに減圧、さらに130Torrに減圧しながら240℃まで昇温し、昇温が終了したところで温度を保持しながら30分かけて0.1Torrまで減圧した。その後10分間、系内を240℃、0.1Torrで保持した後、反応器内に窒素を導入することにより反応系内を常圧に戻し、生成したポリカーボネート樹脂を取り出した。得られた樹脂のMVR、引張強度を表1に示す。
BPEF‐1;20.360g(0.046モル)、2,2‐ビス(4‐ヒドロキシフェニル)プロパン(BPA);1.598g(0.007モル)、ジフェニルカーボネート(DPC);11.910g(0.056モル)、および及び触媒として炭酸水素ナトリウムを6μモル/モル(炭酸水素ナトリウムはBPEFとBPAの合計に対してのモル数であり、0.1wt%水溶液の状態で添加した)とを攪拌器および留出装置付ガラス製200mL反応容器に入れ、系内を窒素雰囲気下に置換し、760Torrの下で200℃に加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で20分間攪拌した。その後、減圧度を200Torrに調整すると同時60℃/hrの速度で210℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。その後、20分間その温度に保持し反応を行った。さらに180Torrに減圧しながら60℃/hrの速度で230℃まで昇温した。昇温終了10分後、温度を保持したままで150Torrに減圧、さらに130Torrに減圧しながら240℃まで昇温し、昇温が終了したところで温度を保持しながら30分かけて0.1Torrまで減圧した。その後10分間、系内を240℃、0.1Torrで保持した後、反応器内に窒素を導入することにより反応系内を常圧に戻し、生成したポリカーボネート樹脂を取り出した。得られた樹脂のMVR、引張強度を表1に示す。
BPEF‐1;19.983g(0.046モル)、および2,2’‐ビス(2‐ヒドロキシエトキシ)‐1,1’‐ビナフタレン(以下「BHEBN」と省略することがある)12.387g(0.033モル)、DPC;17.321g(0.081モル)、および及び触媒として炭酸水素ナトリウムを6μモル/モル(炭酸水素ナトリウムはBPEFとBHEBNの合計に対してのモル数であり、0.1wt%水溶液の状態で添加した)とを攪拌器および留出装置付ガラス製200mL反応容器に入れ、系内を窒素雰囲気下に置換し、760Torrの下で200℃に加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で110分間攪拌を行った。その後減圧度を20Torrに調整すると同時に、60℃/hrの速度で200℃まで昇温を行った。この際副生したフェノールの留出開始を確認した。その後、20分間その温度に保持して反応を行った。さらに75℃/hrの速度で230℃まで昇温し、昇温終了10分後、その温度で保持しながら1時間かけて減圧度を1Torr以下とした。その後、60℃/hrの速度で240℃まで昇温し、さらに240℃、0.2Torrで20分間、反応を行った。反応終了後、反応器内に窒素を導入することにより反応系内を常圧に戻し、生成したポリカーボネート樹脂を取り出した。得られた樹脂のMVR、引張強度を表1に示す。
BPPEF‐1;20.410g(0.035モル)、および2,2’‐ビス(2‐ヒドロキシエトキシ)‐1,1’‐ビナフタレン(以下「BHEBN」と省略することがある)10.140g(0.027モル)、DPC;13.380g(0.0625モル)、および及び触媒として炭酸水素ナトリウムを6μモル/モル(炭酸水素ナトリウムはBPEFとBHEBNの合計に対してのモル数であり、0.1wt%水溶液の状態で添加した)とを攪拌器および留出装置付ガラス製200mL反応容器に入れ、系内を窒素雰囲気下に置換し、760Torrの下で200℃に加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で110分間攪拌を行った。その後減圧度を20Torrに調整すると同時に、60℃/hrの速度で200℃まで昇温を行った。この際副生したフェノールの留出開始を確認した。その後、20分間その温度に保持して反応を行った。さらに75℃/hrの速度で230℃まで昇温し、昇温終了10分後、その温度で保持しながら1時間かけて減圧度を1Torr以下とした。その後、60℃/hrの速度で240℃まで昇温し、さらに240℃、0.2Torrで20分間、反応を行った。反応終了後、反応器内に窒素を導入することにより反応系内を常圧に戻し、生成したポリカーボネート樹脂を取り出した。得られた樹脂のMVR、引張強度を表2に示す。
合成例4において得られたBPPEF‐2を用いる以外は、実施例4と同様に反応を行なった。得られた樹脂のMVR、引張強度を表2に示す。
合成例2において得られたBPEF‐2を用いる以外は、実施例1と同様に反応を行なった。得られた樹脂のMVR、引張強度を表1に示す。
合成例2において得られたBPEF‐2を用いる以外は、実施例2と同様に反応を行なった。得られた樹脂のMVR、引張強度を表1に示す。
合成例2において得られたBPEF‐2を用いる以外は、実施例3と同様に反応を行なった。得られた樹脂のMVR、引張強度を表1に示す。
合成例5において得られたBPPEF‐3を用いる以外は、実施例4と同様に反応を行なった。得られた樹脂のMVR、引張強度を表2に示す。
<実施例6>
合成例1で製造したBPEF‐1;40.000g(0.091モル)、テレフタル酸ジメチル(以下「DMT」と省略することがある)4.4000g(0.023モル)、ジフェニルカーボネート(DPC);15.630g(0.073モル)及び触媒としてチタンブトキシドを1×10-3gとを攪拌器および留出装置付ガラス製200mL反応容器に入れ、系内を窒素雰囲気下に置換し、760Torrの下で190℃に加熱し、その後同条件で20分間攪拌した。引き続き、減圧度を200Torrに調整すると同時60℃/hrの速度で260℃まで昇温を行った。昇温終了10分後、温度を保持したまま60分かけて0.1Torrまで減圧した。その後10分間、系内を260℃、0.1Torrで保持した後、反応器内に窒素を導入することにより反応系内を常圧に戻し、生成したポリカーボネート樹脂を取り出した。得られた樹脂のMVR、引張強度を表3に示す。
原料として、合成例1で製造したBPEF‐1;32.000g(0.073モル)、2,6-ナフタレンジカルボン酸ジメチル(以下「NDCM」と省略することがある)4.4000g(0.018モル)、DPC;12.500g(0.058モル)及び触媒としてチタンブトキシドを1×10-3gに変更した以外は、実施例6と同様に反応した。得られた樹脂のMVR、引張強度を表3に示す。
合成例2で製造したBPEF‐2を用いる以外は、実施例6と同様に反応を行なった。得られた樹脂のMVR、引張強度を表3に示す。
BPPEF: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
BPA:2,2‐ビス(4‐ヒドロキシフェニル)プロパン
BHEBN:2,2’‐ビス(2‐ヒドロキシエトキシ)‐1,1’‐ビナフタレン
DMT:テレフタル酸ジメチル
NDCM:2,6-ナフタレンジカルボン酸ジメチル
フィルムの評価は、以下に示す方法で行った。
全光線透過率およびヘーズは、ヘイズメーター((株)村上色彩技術研究所製、「HM-150」)を用いて、JIS K-7361、JIS K-7136に従って測定した。
示差熱走査熱量分析計(DSC)により測定した(測定機器:株式会社日立ハイテクサイエンスDSC7000X)。
光拡散フィルムの表面形状は、算術平均粗さによって評価した。算術平均粗さは、小型表面粗さ測定機(株式会社ミツトモ製、「サーフテストSJ-210」)を用いて粗さ曲線を作成し、以下のように算出した。作成した粗さ曲線から、基準長さ(l)(平均線方向)の範囲を抜き取り、この抜き取り部分の平均線の方向にX軸を、X軸と直交する方向にY軸を取り、粗さ曲線をy=f(x)で表したときに、次の式によって求められる値(μm)を算術平均粗さ(Ra)とした。ここで、「基準長さ(l)(平均線方向)」とは、JIS B 0601:2001(ISO 4287:1997)に基づいた、粗さパラメータの基準長さを示す。
厚さ0.1mmフィルムについて、アッベ屈折計を用い、JIS-K-7142の方法で測定した(23℃、波長589nm)。
厚さ0.1mmフィルムについて、アッベ屈折計を用い、23℃下での波長486nm、589nmおよび656nmの屈折率を測定し、さらに下記式を用いてアッベ数を算出した。
ν=(nD-1)/(nF-nC)
nD:波長589nmでの屈折率
nC:波長656nmでの屈折率
nF:波長486nmでの屈折率
得られた樹脂を120℃で4時間真空乾燥し、(株)東洋精機製作所製メルトインデクサーT‐111を用い、温度260℃、加重2160gの条件下で測定した。
BHEBNを6.20kg(16.56モル)、BPEF-1を10.00kg(22.80モル)、ジフェニルカーボネート(DPC)を8.67kg(40.46モル)、炭酸水素ナトリウムを1.98×10-2g(2.36×10-4モル)及び反応器を50Lに変えた以外は、実施例3と同様に反応を行った。反応終了後、反応器内に窒素を導入し、生成したポリカーボネート樹脂をペレタイズしながら抜き出した。
BPEF-1;14.99kg(34.18モル)、2,2‐ビス(4‐ヒドロキシフェニル)プロパン;1.18kg(5.15モル)、DPC;8.79kg(41.02モル)、炭酸水素ナトリウム;1.98×10-2g(2.36×10-4モル)及び反応器を50Lに変えた以外は、実施例2と同様に反応を行った。得られたペレットを、実施例8と同様に成形した。
ポリカーボネート樹脂(三菱エンジニアリングプラスチックス株式会社製ユーピロンH-4000;ビスフェノールAからなるポリカーボネート(BPA-HOMO-PC))のペレットを用いて、実施例8と同様にフィルムを作製した。
得られた成形品を複屈折計(王子計測器社製;KOBRA(登録商標)-CCD/X)により測定し、レンズ中心部の、測定波長650nmでのレタデーションの値によって比較した。レタデーションの値は小さいほど低複屈折性に優れていることを意味し、20未満をA、20以上40未満をB、40以上60未満をC、60以上をDとした。
得られた成形品を顕微鏡により観察し、反ゲート方向に生じたウェルドライン長さの測定を行った。ウェルドラインの長さが0.1mm未満ならA、0.1mm以上0.3mm未満ならB、0.3mm以上0.5mm未満ならC、0.5mm以上ならD、とした。
実施例1において得られポリカーボネート樹脂を用い、射出成型物を作成した。得られた成形物の複屈折評価、ウエルドライン評価結果を表5に示す。
実施例2において得られポリカーボネート樹脂を用い、射出成型物を作成した。得られた成形物の複屈折評価、ウエルドライン評価結果を表5に示す。
実施例3において得られポリカーボネート樹脂を用い、射出成型物を作成した。得られた成形物の複屈折評価、ウエルドライン評価結果を表5に示す。
実施例4において得られポリカーボネート樹脂を用い、射出成型物を作成した。得られた成形物の複屈折評価、ウエルドライン評価結果を表5に示す。
実施例5において得られポリカーボネート樹脂を用い、射出成型物を作成した。得られた成形物の複屈折評価、ウエルドライン評価結果を表5に示す。
比較例1において得られポリカーボネート樹脂を用い、射出成型物を作成した。得られた成形物の複屈折評価、ウエルドライン評価結果を表5に示す。
比較例2において得られポリカーボネート樹脂を用い、射出成型物を作成した。得られた成形物の複屈折評価、ウエルドライン評価結果を表5に示す。
比較例3において得られポリカーボネート樹脂を用い、射出成型物を作成した。得られた成形物の複屈折評価、ウエルドライン評価結果を表5に示す。
ポリカーボネート樹脂(三菱エンジニアリングプラスチックス株式会社製ユーピロンH-4000;ビスフェノールAからなるポリカーボネート(BPA-HOMO-PC))のペレットを用い、射出成型物を作成した。得られた成形物の複屈折評価、ウエルドライン評価結果を表5に示す。
Claims (15)
- ジヒドロキシ化合物を含む反応物を反応させて熱可塑性樹脂を製造する方法であって、
前記ジヒドロキシ化合物は、
下記式(1)で表されるジヒドロキシ化合物と、
下記式(A)で表される化合物、下記式(B)で表される化合物、および下記式(C)で表される化合物の少なくとも一つと、
を含み、
前記式(A)で表される化合物、式(B)で表される化合物、および式(C)で表される化合物の合計重量が、前記式(1)で表されるジヒドロキシ化合物の重量(100重量部)に対して、1,500ppm以上である、製造方法。
- 前記ジヒドロキシ化合物における前記式(A)で表される化合物の重量が、前記式(1)で表されるジヒドロキシ化合物の重量(100重量部)に対して、1,000ppm以上である、請求項1に記載の製造方法。
- 前記ジヒドロキシ化合物における前記式(B)で表される化合物の重量が、前記式(1)で表されるジヒドロキシ化合物の重量(100重量部)に対して、200ppm以上である、請求項1または2に記載の製造方法。
- 前記ジヒドロキシ化合物における前記式(C)で表される化合物の重量が、前記式(1)で表されるジヒドロキシ化合物の重量(100重量部)に対して、200ppm以上である、請求項1~3のいずれか一項に記載の製造方法。
- 前記ジヒドロキシ化合物は、下記式(2)で表されるジヒドロキシ化合物および下記式(3)で表されるジヒドロキシ化合物からなる群から選択される少なくとも一つをさらに含有する、請求項1~4のいずれか一項に記載の製造方法。
Z1およびZ2はそれぞれ独立に、炭素数1~8のアルキレン基、炭素数6~10のシクロアルキレン基、および炭素数6~10のアリーレン基からなる群から選択され;
l1およびl2はそれぞれ独立に、0~5の整数であり;
Qは単結合または
ここで、R8、R9、R14~R17はそれぞれ独立に、水素原子、炭素数1~10のアルキル基、およびフェニル基からなる群から選択され;
R10~R13はそれぞれ独立に、水素原子または炭素数1~5のアルキル基を表し;
Z’は3~11の整数であり;
R6とR7は同じでも異なっていても良い。) - Xがエチレン基である請求項1~5のいずれか一項に記載の製造方法。
- 前記熱可塑性樹脂はポリカーボネート樹脂、ポリエステル樹脂、およびポリエステルカーボネート樹脂からなる群から選択される、請求項1~6のいずれか一項に記載の製造方法。
- 前記熱可塑性樹脂はポリカーボネート樹脂である、請求項7に記載の製造方法。
- 前記反応物が、炭酸ジエステルをさらに含む、請求項1~8のいずれか一項に記載の製造方法。
- 前記熱可塑性樹脂はポリエステルカーボネート樹脂であり、
前記反応物は、前記ジヒドロキシ化合物と、炭酸ジエステルと、テレフタル酸、2,6-ナフタレンジカルボン酸およびフルオレン-9,9-ジプロピオン酸から選択される少なくとも一種を含むジカルボン酸またはその誘導体とを含み、
前記ジヒドロキシ化合物と前記ジカルボン酸またはその誘導体とのモル比は、(ジヒドロキシ化合物/ジカルボン酸またはその誘導体)は、20/80~95/5である、請求項7に記載の製造方法。 - 引張強度が70%以上である請求項1~10のいずれか一項に記載の製造方法。
- 請求項1~11のいずれか一項に記載の製造方法で得られた熱可塑性樹脂を成形する工程を含む、成形体の製造方法。
- 請求項1~11のいずれか一項に記載の製造方法で得られた熱可塑性樹脂または請求項12に記載の製造方法で得られた成形体を用いることを特徴とする、光学材料の製造方法。
- 請求項1~11のいずれか一項に記載の製造方法で得られた熱可塑性樹脂または請求項12に記載の製造方法で得られた成形体を用いることを特徴とする、光学レンズの製造方法。
- 請求項1~11のいずれか一項に記載の製造方法で得られた熱可塑性樹脂または請求項12に記載の製造方法で得られた成形体を用いることを特徴とする、光学フィルムを製造方法。
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020187014565A KR102659378B1 (ko) | 2015-11-04 | 2016-11-02 | 열가소성 수지의 제조 방법 |
US15/769,182 US10955680B2 (en) | 2015-11-04 | 2016-11-02 | Method of producing thermoplastic resin |
JP2017548811A JP7047381B2 (ja) | 2015-11-04 | 2016-11-02 | 熱可塑性樹脂の製造方法 |
EP16862134.0A EP3372627B1 (en) | 2015-11-04 | 2016-11-02 | Method of producing thermoplastic resin |
EP19169192.2A EP3536728B1 (en) | 2015-11-04 | 2016-11-02 | Method of producing thermoplastic resin |
CN201680063600.XA CN108350163B (zh) | 2015-11-04 | 2016-11-02 | 热塑性树脂的制造方法 |
CN201910303419.7A CN110256661B (zh) | 2015-11-04 | 2016-11-02 | 热塑性树脂的制造方法 |
KR1020247012232A KR20240055857A (ko) | 2015-11-04 | 2016-11-02 | 열가소성 수지의 제조 방법 |
CN202110665289.9A CN113248697B (zh) | 2015-11-04 | 2016-11-02 | 热塑性树脂的制造方法 |
KR1020197010654A KR102678028B1 (ko) | 2015-11-04 | 2016-11-02 | 디하이드록시 화합물 |
US16/383,143 US10962793B2 (en) | 2015-11-04 | 2019-04-12 | Method of producing thermoplastic resin |
JP2021205679A JP7238952B2 (ja) | 2015-11-04 | 2021-12-20 | 熱可塑性樹脂の製造方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015216978 | 2015-11-04 | ||
JP2015-216978 | 2015-11-04 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/769,182 A-371-Of-International US10955680B2 (en) | 2015-11-04 | 2016-11-02 | Method of producing thermoplastic resin |
US16/383,143 Division US10962793B2 (en) | 2015-11-04 | 2019-04-12 | Method of producing thermoplastic resin |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2017078074A1 true WO2017078074A1 (ja) | 2017-05-11 |
Family
ID=58662071
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2016/082615 WO2017078074A1 (ja) | 2015-11-04 | 2016-11-02 | 熱可塑性樹脂の製造方法 |
Country Status (7)
Country | Link |
---|---|
US (2) | US10955680B2 (ja) |
EP (2) | EP3536728B1 (ja) |
JP (3) | JP7047381B2 (ja) |
KR (2) | KR20240055857A (ja) |
CN (3) | CN108350163B (ja) |
TW (3) | TWI727990B (ja) |
WO (1) | WO2017078074A1 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018076238A (ja) * | 2016-11-07 | 2018-05-17 | 田岡化学工業株式会社 | フルオレン骨格を含む樹脂原料用組成物およびその製造方法 |
JP2020037546A (ja) * | 2018-09-06 | 2020-03-12 | 田岡化学工業株式会社 | フルオレン骨格を有するアルコール化合物を含む樹脂原料用組成物 |
WO2020080199A1 (ja) * | 2018-10-16 | 2020-04-23 | 三菱瓦斯化学株式会社 | ポリエステルカーボネート樹脂および光学レンズ |
CN111094389A (zh) * | 2017-08-30 | 2020-05-01 | 三菱瓦斯化学株式会社 | 聚碳酸酯树脂、其制造方法和光学透镜 |
WO2022230471A1 (ja) * | 2021-04-26 | 2022-11-03 | 三菱瓦斯化学株式会社 | 熱可塑性樹脂組成物及びそれに添加される配合剤 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR112020007384A2 (pt) * | 2017-10-26 | 2020-09-29 | Saint-Gobain Glass France | peça de complemento tendo um módulo de câmera integrado |
EP4092068A4 (en) | 2020-01-16 | 2023-04-26 | Asahi Kasei Kabushiki Kaisha | POLYCARBONATE RESIN, POLYCARBONATE RESIN COMPOSITION, MOLDED OPTICAL COMPOSITION INCLUDING THEM, AND CYCLIC CARBONATE |
KR20240047925A (ko) * | 2022-10-05 | 2024-04-12 | 주식회사 엘지화학 | 폴리카보네이트 수지 및 이의 제조방법 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010248095A (ja) * | 2009-04-13 | 2010-11-04 | Taoka Chem Co Ltd | 9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの製造法 |
JP2012077266A (ja) * | 2010-10-06 | 2012-04-19 | Teijin Chem Ltd | フルオレン誘導体からなる熱可塑性樹脂およびその溶融重合方法 |
JP2014169396A (ja) * | 2013-03-04 | 2014-09-18 | Mitsubishi Chemicals Corp | ポリカーボネート樹脂製造方法 |
JP2014214251A (ja) * | 2013-04-26 | 2014-11-17 | 帝人株式会社 | ポリエステルカーボネート共重合体 |
JP2014214220A (ja) * | 2013-04-25 | 2014-11-17 | 帝人株式会社 | ポリカーボネート |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10101786A (ja) | 1996-09-30 | 1998-04-21 | Teijin Ltd | ポリカーボネート共重合体およびその製造方法 |
JP2001122828A (ja) * | 1999-10-27 | 2001-05-08 | Shinnakamura Kagaku Kogyo Kk | 2官能(メタ)アクリル酸エステル組成物とそのための2価アルコール |
KR20090126260A (ko) | 2007-02-15 | 2009-12-08 | 다오카가가쿠고교가부시키가이샤 | 플루오렌 유도체의 결정 다형체 및 그 제조 방법 |
JP5325627B2 (ja) * | 2008-03-27 | 2013-10-23 | 大阪瓦斯株式会社 | フルオレン骨格を有するアルコールの製造方法 |
JP5202146B2 (ja) | 2008-07-14 | 2013-06-05 | 日本化薬株式会社 | (メタ)アクリレート化合物及びそれを含有する活性エネルギー線硬化型樹脂組成物並びにその硬化物 |
EP2420485B1 (en) | 2009-04-13 | 2014-04-09 | Taoka Chemical Co., Ltd. | Method for producing fluorene derivative |
WO2011010741A1 (ja) | 2009-07-24 | 2011-01-27 | 帝人化成株式会社 | 光学レンズ用ポリエステルカーボネート共重合体および光学レンズ |
CN104471451A (zh) * | 2012-08-01 | 2015-03-25 | 三菱化学株式会社 | 聚碳酸酯树脂组合物及透明膜 |
EP4219588A1 (en) | 2012-11-07 | 2023-08-02 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin, production method therefor, and optical molded body |
JP6154337B2 (ja) | 2013-02-20 | 2017-06-28 | 帝人株式会社 | ポリカーボネート共重合体 |
JP6139258B2 (ja) * | 2013-05-13 | 2017-05-31 | 帝人株式会社 | ポリエステルカーボネート共重合体 |
JP6253099B2 (ja) | 2014-03-10 | 2017-12-27 | 田岡化学工業株式会社 | 2,2’−ビス(2−ヒドロキシエトキシ)−1,1’−ビナフタレンの製造方法 |
US10634819B2 (en) * | 2015-11-04 | 2020-04-28 | MlTSUBISHI GAS CHEMICAL COMPANY, INC. | Resin composition, and optical lens, sheet and film which contain same |
-
2016
- 2016-11-02 JP JP2017548811A patent/JP7047381B2/ja active Active
- 2016-11-02 US US15/769,182 patent/US10955680B2/en active Active
- 2016-11-02 KR KR1020247012232A patent/KR20240055857A/ko not_active Application Discontinuation
- 2016-11-02 TW TW105135547A patent/TWI727990B/zh active
- 2016-11-02 TW TW110122172A patent/TWI806078B/zh active
- 2016-11-02 CN CN201680063600.XA patent/CN108350163B/zh active Active
- 2016-11-02 WO PCT/JP2016/082615 patent/WO2017078074A1/ja active Application Filing
- 2016-11-02 EP EP19169192.2A patent/EP3536728B1/en active Active
- 2016-11-02 KR KR1020187014565A patent/KR102659378B1/ko active IP Right Grant
- 2016-11-02 CN CN202110665289.9A patent/CN113248697B/zh active Active
- 2016-11-02 TW TW108113440A patent/TWI741281B/zh active
- 2016-11-02 CN CN201910303419.7A patent/CN110256661B/zh active Active
- 2016-11-02 EP EP16862134.0A patent/EP3372627B1/en active Active
-
2019
- 2019-04-08 JP JP2019073324A patent/JP7047808B2/ja active Active
- 2019-04-12 US US16/383,143 patent/US10962793B2/en active Active
-
2021
- 2021-12-20 JP JP2021205679A patent/JP7238952B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010248095A (ja) * | 2009-04-13 | 2010-11-04 | Taoka Chem Co Ltd | 9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの製造法 |
JP2012077266A (ja) * | 2010-10-06 | 2012-04-19 | Teijin Chem Ltd | フルオレン誘導体からなる熱可塑性樹脂およびその溶融重合方法 |
JP2014169396A (ja) * | 2013-03-04 | 2014-09-18 | Mitsubishi Chemicals Corp | ポリカーボネート樹脂製造方法 |
JP2014214220A (ja) * | 2013-04-25 | 2014-11-17 | 帝人株式会社 | ポリカーボネート |
JP2014214251A (ja) * | 2013-04-26 | 2014-11-17 | 帝人株式会社 | ポリエステルカーボネート共重合体 |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018076238A (ja) * | 2016-11-07 | 2018-05-17 | 田岡化学工業株式会社 | フルオレン骨格を含む樹脂原料用組成物およびその製造方法 |
CN111094389A (zh) * | 2017-08-30 | 2020-05-01 | 三菱瓦斯化学株式会社 | 聚碳酸酯树脂、其制造方法和光学透镜 |
EP3677615A4 (en) * | 2017-08-30 | 2020-09-23 | Mitsubishi Gas Chemical Company, Inc. | POLYCARBONATE RESIN, PROCESS FOR THE PRODUCTION OF THE SAME AND OPTICAL LENS |
US11434327B2 (en) | 2017-08-30 | 2022-09-06 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin, method for producing the same, and optical lens |
US11952460B2 (en) | 2017-08-30 | 2024-04-09 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin, method for producing the same, and optical lens |
JP2020037546A (ja) * | 2018-09-06 | 2020-03-12 | 田岡化学工業株式会社 | フルオレン骨格を有するアルコール化合物を含む樹脂原料用組成物 |
JP7146345B2 (ja) | 2018-09-06 | 2022-10-04 | 田岡化学工業株式会社 | フルオレン骨格を有するアルコール化合物を含む樹脂原料用組成物 |
WO2020080199A1 (ja) * | 2018-10-16 | 2020-04-23 | 三菱瓦斯化学株式会社 | ポリエステルカーボネート樹脂および光学レンズ |
JPWO2020080199A1 (ja) * | 2018-10-16 | 2021-09-30 | 三菱瓦斯化学株式会社 | ポリエステルカーボネート樹脂および光学レンズ |
US11732088B2 (en) | 2018-10-16 | 2023-08-22 | Mitsubishi Gas Chemical Company, Inc. | Polyester carbonate resin and optical lens |
JP7342878B2 (ja) | 2018-10-16 | 2023-09-12 | 三菱瓦斯化学株式会社 | ポリエステルカーボネート樹脂および光学レンズ |
WO2022230471A1 (ja) * | 2021-04-26 | 2022-11-03 | 三菱瓦斯化学株式会社 | 熱可塑性樹脂組成物及びそれに添加される配合剤 |
Also Published As
Publication number | Publication date |
---|---|
EP3372627A4 (en) | 2019-06-12 |
JP7047381B2 (ja) | 2022-04-05 |
EP3372627A1 (en) | 2018-09-12 |
EP3536728A1 (en) | 2019-09-11 |
TW201934604A (zh) | 2019-09-01 |
TW201731904A (zh) | 2017-09-16 |
EP3536728B1 (en) | 2022-10-12 |
US10962793B2 (en) | 2021-03-30 |
CN108350163A (zh) | 2018-07-31 |
JP2019143152A (ja) | 2019-08-29 |
US20190235258A1 (en) | 2019-08-01 |
US20180307052A1 (en) | 2018-10-25 |
JPWO2017078074A1 (ja) | 2018-08-23 |
TWI806078B (zh) | 2023-06-21 |
CN108350163B (zh) | 2021-07-06 |
US10955680B2 (en) | 2021-03-23 |
KR20190041544A (ko) | 2019-04-22 |
KR20240055857A (ko) | 2024-04-29 |
CN110256661B (zh) | 2022-04-08 |
CN110256661A (zh) | 2019-09-20 |
CN113248697B (zh) | 2023-03-21 |
TWI727990B (zh) | 2021-05-21 |
EP3372627B1 (en) | 2020-05-27 |
KR102659378B1 (ko) | 2024-04-19 |
TWI741281B (zh) | 2021-10-01 |
KR20180079359A (ko) | 2018-07-10 |
JP7047808B2 (ja) | 2022-04-05 |
TW202140608A (zh) | 2021-11-01 |
JP7238952B2 (ja) | 2023-03-14 |
JP2022046587A (ja) | 2022-03-23 |
CN113248697A (zh) | 2021-08-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7238952B2 (ja) | 熱可塑性樹脂の製造方法 | |
JP6631514B2 (ja) | 重縮合で製造された樹脂および樹脂組成物 | |
JP7136265B2 (ja) | 熱可塑性樹脂の製造方法 | |
KR102678028B1 (ko) | 디하이드록시 화합물 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16862134 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 15769182 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 2017548811 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 20187014565 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2016862134 Country of ref document: EP |