JP2024055310A - Thermoplastic resin composition and optical member containing same - Google Patents
Thermoplastic resin composition and optical member containing same Download PDFInfo
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- JP2024055310A JP2024055310A JP2022162131A JP2022162131A JP2024055310A JP 2024055310 A JP2024055310 A JP 2024055310A JP 2022162131 A JP2022162131 A JP 2022162131A JP 2022162131 A JP2022162131 A JP 2022162131A JP 2024055310 A JP2024055310 A JP 2024055310A
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- Prior art keywords
- thermoplastic resin
- resin composition
- bis
- formula
- ppm
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- 229920005992 thermoplastic resin Polymers 0.000 title claims abstract description 129
- 239000011342 resin composition Substances 0.000 title claims abstract description 101
- 230000003287 optical effect Effects 0.000 title claims abstract description 45
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 26
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000005647 linker group Chemical group 0.000 claims abstract description 7
- 239000006082 mold release agent Substances 0.000 claims abstract description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 229920005989 resin Polymers 0.000 claims description 32
- 239000011347 resin Substances 0.000 claims description 32
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 29
- 229920000728 polyester Polymers 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 229920005668 polycarbonate resin Polymers 0.000 claims description 18
- 239000004431 polycarbonate resin Substances 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000004383 yellowing Methods 0.000 claims description 9
- 230000007774 longterm Effects 0.000 abstract description 22
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 14
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000008188 pellet Substances 0.000 description 31
- -1 naphthalenediyl group Chemical group 0.000 description 19
- 238000004898 kneading Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000000654 additive Substances 0.000 description 13
- 239000006096 absorbing agent Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 10
- 150000002009 diols Chemical class 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 229910000831 Steel Inorganic materials 0.000 description 9
- 238000000465 moulding Methods 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000010959 steel Substances 0.000 description 9
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 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 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 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 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000004075 alteration Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000002685 polymerization catalyst Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 150000003009 phosphonic acids Chemical class 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 3
- KLDXJTOLSGUMSJ-UNTFVMJOSA-N (3s,3ar,6s,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-UNTFVMJOSA-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
- GJDRKHHGPHLVNI-UHFFFAOYSA-N 2,6-ditert-butyl-4-(diethoxyphosphorylmethyl)phenol Chemical compound CCOP(=O)(OCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GJDRKHHGPHLVNI-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
- 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 2
- 229920001651 Cyanoacrylate Polymers 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- YNCDEEFMDXHURQ-UHFFFAOYSA-N aluminum;ethyl 3-oxobutanoate Chemical compound [Al].CCOC(=O)CC(C)=O YNCDEEFMDXHURQ-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 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
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 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
- 230000008859 change Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000003063 flame retardant Substances 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
- 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
- 239000000314 lubricant Substances 0.000 description 2
- 239000006078 metal deactivator Substances 0.000 description 2
- 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 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-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
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- NJHVXCSESBEOEB-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl) dihydrogen phosphite Chemical compound CC1=CC(C(C)(C)C)=C(OP(O)O)C(C(C)(C)C)=C1 NJHVXCSESBEOEB-UHFFFAOYSA-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
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 1
- GLCPRUJXNXWSRF-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene-2,6-dicarboxylic acid Chemical compound C1C(C(O)=O)CCC2CC(C(=O)O)CCC21 GLCPRUJXNXWSRF-UHFFFAOYSA-N 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
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- MJMYTWUUAMWUNG-UHFFFAOYSA-N 1-[4-[9-[4-(2-hydroxypropoxy)phenyl]fluoren-9-yl]phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)C)=CC=C1C1(C=2C=CC(OCC(C)O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 MJMYTWUUAMWUNG-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
- 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
- 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 1
- 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 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
- 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
- BBITXNWQALLODC-UHFFFAOYSA-N 2-[4-(4-oxo-3,1-benzoxazin-2-yl)phenyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C3=CC=C(C=C3)C=3OC(C4=CC=CC=C4N=3)=O)=NC2=C1 BBITXNWQALLODC-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- GUFIKYXJLDNKON-UHFFFAOYSA-N 2-[6-[9-[6-(2-hydroxyethoxy)naphthalen-2-yl]-2,7-diphenylfluoren-9-yl]naphthalen-2-yl]oxyethanol Chemical compound OCCOC=1C=C2C=CC(=CC2=CC=1)C1(C2=CC(=CC=C2C=2C=CC(=CC1=2)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC2=CC=C(C=C2C=C1)OCCO GUFIKYXJLDNKON-UHFFFAOYSA-N 0.000 description 1
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- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
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- KMJRBSYFFVNPPK-UHFFFAOYSA-K aluminum;dodecanoate Chemical compound [Al+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O KMJRBSYFFVNPPK-UHFFFAOYSA-K 0.000 description 1
- LIQDVINWFSWENU-UHFFFAOYSA-K aluminum;prop-2-enoate Chemical compound [Al+3].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C LIQDVINWFSWENU-UHFFFAOYSA-K 0.000 description 1
- DMGNPLVEZUUCBT-UHFFFAOYSA-K aluminum;propanoate Chemical compound [Al+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O DMGNPLVEZUUCBT-UHFFFAOYSA-K 0.000 description 1
- CSJKPFQJIDMSGF-UHFFFAOYSA-K aluminum;tribenzoate Chemical compound [Al+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 CSJKPFQJIDMSGF-UHFFFAOYSA-K 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
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- FNGGVJIEWDRLFV-UHFFFAOYSA-N anthracene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=CC=C3C=C21 FNGGVJIEWDRLFV-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ZCLVNIZJEKLGFA-UHFFFAOYSA-H bis(4,5-dioxo-1,3,2-dioxalumolan-2-yl) oxalate Chemical compound [Al+3].[Al+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O ZCLVNIZJEKLGFA-UHFFFAOYSA-H 0.000 description 1
- 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 1
- 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 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- WLZGEDNSZCPRCJ-UHFFFAOYSA-M cesium;octadecanoate Chemical compound [Cs+].CCCCCCCCCCCCCCCCCC([O-])=O WLZGEDNSZCPRCJ-UHFFFAOYSA-M 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
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- 238000011109 contamination Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- REKWWOFUJAJBCL-UHFFFAOYSA-L dilithium;hydrogen phosphate Chemical compound [Li+].[Li+].OP([O-])([O-])=O REKWWOFUJAJBCL-UHFFFAOYSA-L 0.000 description 1
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- TYJOJLOWRIQYQM-UHFFFAOYSA-L disodium;phenyl phosphate Chemical compound [Na+].[Na+].[O-]P([O-])(=O)OC1=CC=CC=C1 TYJOJLOWRIQYQM-UHFFFAOYSA-L 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
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- 238000005530 etching Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 229940031993 lithium benzoate Drugs 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
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- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-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
- 125000004957 naphthylene group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-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
- 239000013307 optical fiber Substances 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- AJDJKHROQJQURF-UHFFFAOYSA-N phenanthrene-1,2-dicarboxylic acid Chemical compound C1=CC=C2C3=CC=C(C(=O)O)C(C(O)=O)=C3C=CC2=C1 AJDJKHROQJQURF-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
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- 229930003231 vitamin Natural products 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
【課題】本発明は、高屈折率及び低複屈折を有し、且つ、長期耐熱性に優れる熱可塑性樹脂組成物を提供することを目的とする。また、この熱可塑性樹脂組成物を使用することにより、優れた光学レンズを提供することを目的とする。【解決手段】下記式（１）で表される構成単位を有する熱可塑性樹脂および離型剤を含む熱可塑性樹脂組成物であって、さらに熱可塑性樹脂組成物中の酸化防止剤の含有量が０～３００ｐｐｍである熱可塑性樹脂組成物。JPEG2024055310000013.jpg3482｛式（１）中、環Ｚは芳香族炭化水素環を示し、Ｌ１及びＬ２はそれぞれ独立に２価の連結基を示し、ｏ及びｐはそれぞれ独立に０以上の整数を示し、Ｒ１、Ｒ２、Ｒ３及びＲ４はそれぞれ独立に、水素原子、炭素原子数１～２０の炭化水素基を示し、Ｘは炭酸もしくはジカルボン酸から水酸基を除いた残基である。｝【選択図】なし[Problem] The present invention aims to provide a thermoplastic resin composition having a high refractive index, low birefringence, and excellent long-term heat resistance. It is also an object of the present invention to provide an excellent optical lens by using this thermoplastic resin composition. [Solution] A thermoplastic resin composition comprising a thermoplastic resin having a structural unit represented by the following formula (1) and a mold release agent, wherein the content of an antioxidant in the thermoplastic resin composition is 0 to 300 ppm. JPEG2024055310000013.jpg3482 {In formula (1), ring Z represents an aromatic hydrocarbon ring, L1 and L2 each independently represent a divalent linking group, o and p each independently represent an integer of 0 or more, R1, R2, R3, and R4 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and X is a residue obtained by removing a hydroxyl group from carbonic acid or dicarboxylic acid.} [Selected Figure] None
Description
本発明は、熱可塑性樹脂組成物及びそれを含む光学部材に関するものである。 The present invention relates to a thermoplastic resin composition and an optical member containing the same.
光学系材料として従来用いられていたガラスは光学特性や環境耐性に優れているが、加工性が悪いという問題があった。一方、光学用樹脂、中でも熱可塑性樹脂組成物は、ガラス材料に比べ安価であると共に、射出成形により成形品の大量生産が可能で、しかも非球面レンズの製造も容易であるという利点を有している。そのため、これまで主としてスマートフォンカメラを構成する光学レンズに使用され、普及してきた。近年では新たな用途として、車載センシングカメラや車載ビューイングカメラといったいわゆる車載カメラの光学レンズへの展開が期待されている。 Glass, which has traditionally been used as an optical system material, has excellent optical properties and environmental resistance, but has the problem of poor processability. On the other hand, optical resins, especially thermoplastic resin compositions, are cheaper than glass materials, and have the advantages of being able to mass-produce molded products by injection molding and easily producing aspherical lenses. For this reason, they have been used primarily in the optical lenses that make up smartphone cameras, and have become widespread. In recent years, a new application for these resins is expected to be the optical lenses for so-called vehicle-mounted cameras, such as vehicle-mounted sensing cameras and vehicle-mounted viewing cameras.
そのような中で光学用樹脂には、光学系の小型、薄型化の為、より高い屈折率が求められ、また光学レンズを介して結像をセンサーや人が認識する為、高度に低歪であること、つまり低複屈折であることが求められる。さらに車載カメラ用途では、その使用環境から高温下で長時間変色しないという長期耐熱性が重要である。 In this environment, optical resins are required to have a higher refractive index in order to make optical systems smaller and thinner, and also to have extremely low distortion, i.e. low birefringence, because images formed through optical lenses are recognized by sensors and people. Furthermore, for in-vehicle camera applications, long-term heat resistance is important so that the color does not change over long periods of time even at high temperatures due to the operating environment.
特許文献１には、屈折率が１．６３５～１．６５０の高屈折率且つ配向複屈折が０～６×１０－３の低複屈折に優れた、式（Ｍ）及び式（Ｎ）で示される構造単位を有するポリエステルカーボネート樹脂が得られることが記載されている。 Patent Document 1 describes that a polyester carbonate resin having structural units represented by formula (M) and formula (N) can be obtained, which has a high refractive index of 1.635 to 1.650 and an excellent low orientation birefringence of 0 to 6 × 10-3 .
特許文献２には、アルミニウム化合物とリン化合物からなる触媒を用いたポリエステルカーボネート樹脂が一般的なチタン系触媒を用いた場合よりも色相が良好と記載されている。 Patent Document 2 describes that polyester carbonate resins produced using a catalyst made of an aluminum compound and a phosphorus compound have better color than those produced using a general titanium-based catalyst.
特許文献３には、高透明性、高Ｔｇ、高屈折率、低複屈折に優れる、式（Ｏ）で表される構造を有するポリカーボネート樹脂が得られることが記載されている。 Patent Document 3 describes that a polycarbonate resin having a structure represented by formula (O) can be obtained that has excellent properties such as high transparency, high Tg, high refractive index, and low birefringence.
上述した文献には、高屈折率、低複屈折、高透明性、高Ｔｇ、色相良好なポリカーボネート樹脂またはポリエステルカーボネート樹脂の取得について記載されているが、押出、成形後の熱可塑性樹脂組成物としての特性、特に長期耐熱性について記載されておらず、改良の余地がある。 The above-mentioned documents describe the production of polycarbonate resins or polyester carbonate resins with high refractive index, low birefringence, high transparency, high Tg, and good color, but do not describe the properties of the thermoplastic resin composition after extrusion and molding, particularly the long-term heat resistance, and there is room for improvement.
上記のように、高屈折率、低複屈折に加え、長期耐熱性を有するポリカーボネート樹脂組成物及びポリエステルカーボネート樹脂組成物及び光学レンズは、未だ提供されていなかった。 As described above, polycarbonate resin compositions and polyester carbonate resin compositions and optical lenses that have a high refractive index, low birefringence, and long-term heat resistance have not yet been provided.
そこで本発明は、高屈折率及び低複屈折を有し、且つ、長期耐熱性に優れる熱可塑性樹脂組成物を提供することを目的とする。また、この熱可塑性樹脂組成物を使用することにより、優れた光学レンズを提供することを目的とする。 The present invention aims to provide a thermoplastic resin composition that has a high refractive index, low birefringence, and excellent long-term heat resistance. It also aims to provide an excellent optical lens by using this thermoplastic resin composition.
本発明者らは、以下の態様を有する本発明により、上記課題を解決できることを見出した。 The inventors have discovered that the above problems can be solved by the present invention, which has the following features:
《態様１》
下記式（１）で表される構成単位を有する熱可塑性樹脂および離型剤を含む熱可塑性樹脂組成物であって、さらに熱可塑性樹脂組成物中の酸化防止剤の含有量が０～３００ｐｐｍである熱可塑性樹脂組成物。
<<Aspect 1>>
A thermoplastic resin composition comprising a thermoplastic resin having a structural unit represented by the following formula (1) and a mold release agent, wherein the content of an antioxidant in the thermoplastic resin composition is 0 to 300 ppm:
《態様２》
前記離型剤が熱可塑性樹脂組成物中に１～４０００ｐｐｍの量で含まれる、態様１に記載の熱可塑性樹脂組成物。
《態様３》
前記熱可塑性樹脂組成物中の酸化防止剤の含有量が０～５０ｐｐｍである、態様１又は２に記載の熱可塑性樹脂組成物。
《態様４》
乾熱黄変ΔＹＩが０．００～０．４７である、態様１～３のいずれか一項に記載の熱可塑性樹脂組成物。
《態様５》
前記式（１）中の環Ｚがベンゼン環である、態様１～４のいずれか一項に記載の熱可塑性樹脂組成物。
《態様６》
式（１）で表される構成単位を有する熱可塑性樹脂が、ポリカーボネート樹脂またはポリエステルカーボネート樹脂である態様１～５のいずれか一項に記載の熱可塑性樹脂組成物。
《態様７》
式（１）で表される構成単位を有する熱可塑性樹脂が、ポリエステルカーボネート樹脂である態様６に記載の熱可塑性樹脂組成物。
《態様８》
態様１～７のいずれか一項に記載の熱可塑性樹脂組成物を含む、光学部材。
《態様９》
光学レンズである、態様８に記載の光学部材。
Aspect 2
2. The thermoplastic resin composition according to claim 1, wherein the release agent is contained in the thermoplastic resin composition in an amount of 1 to 4000 ppm.
Aspect 3
The thermoplastic resin composition according to claim 1 or 2, wherein the content of the antioxidant in the thermoplastic resin composition is 0 to 50 ppm.
Aspect 4
The thermoplastic resin composition according to any one of claims 1 to 3, wherein the dry heat yellowing ΔYI is 0.00 to 0.47.
Aspect 5
The thermoplastic resin composition according to any one of claims 1 to 4, wherein ring Z in formula (1) is a benzene ring.
Aspect 6
The thermoplastic resin composition according to any one of aspects 1 to 5, wherein the thermoplastic resin having a structural unit represented by formula (1) is a polycarbonate resin or a polyester carbonate resin.
Aspect 7
The thermoplastic resin composition according to embodiment 6, wherein the thermoplastic resin having a structural unit represented by formula (1) is a polyester carbonate resin.
Aspect 8
An optical member comprising the thermoplastic resin composition according to any one of aspects 1 to 7.
Aspect 9
9. The optical member according to claim 8, which is an optical lens.
本発明の熱可塑性樹脂組成物は、高屈折率、低複屈折を有し、且つ、長期耐熱性に優れる。さらに、本発明の熱可塑性樹脂組成物を使用することにより、広範な環境に適応可能な優れた光学レンズを得ることができる。 The thermoplastic resin composition of the present invention has a high refractive index, low birefringence, and excellent long-term heat resistance. Furthermore, by using the thermoplastic resin composition of the present invention, it is possible to obtain an excellent optical lens that can be adapted to a wide range of environments.
以下、本発明を実施するための形態について詳細に説明するが、本発明はこれに限定されるものではなく、その要旨を逸脱しない範囲で様々な変形が可能である。 The following describes in detail the mode for carrying out the present invention, but the present invention is not limited to this, and various modifications are possible without departing from the gist of the invention.
（１）熱可塑性樹脂組成物
本発明の熱可塑性樹脂組成物は、所定の構造を有する熱可塑性樹脂と離型剤を含み、さらに熱可塑性樹脂組成物中の酸化防止剤の含有量が０～３００ｐｐｍの熱可塑性樹脂組成物である。本発明の熱可塑性樹脂組成物は、このような構成により、高屈折率、低複屈折を有し、かつ、優れた長期耐熱性を有する。
(1) Thermoplastic resin composition The thermoplastic resin composition of the present invention is a thermoplastic resin composition that contains a thermoplastic resin having a predetermined structure and a mold release agent, and further contains an antioxidant in an amount of 0 to 300 ppm. Due to this constitution, the thermoplastic resin composition of the present invention has a high refractive index, low birefringence, and excellent long-term heat resistance.
《熱可塑性樹脂》
本発明に用いる熱可塑性樹脂は上記式（１）で表される構造を有する。
上記式（１）中、Ｚは同一又は異なって芳香族炭化水素環を示し、ナフタレン環、ベンゼン環などが挙げられ、ベンゼン環が好ましい。
"Thermoplastic resin"
The thermoplastic resin used in the present invention has a structure represented by the above formula (1).
In the above formula (1), Z may be the same or different and represents an aromatic hydrocarbon ring, such as a naphthalene ring or a benzene ring, with a benzene ring being preferred.
上記式（１）中、Ｒ１、Ｒ２、Ｒ３及びＲ４は、それぞれ独立に、水素原子、炭素原子数１～２０の炭化水素基を示し、炭化水素基としては、アルキル基、シクロアルキル基、及びアリール基を挙げることができる。 In the above formula (1), R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and examples of the hydrocarbon group include an alkyl group, a cycloalkyl group, and an aryl group.
アルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、ｔ－ブチル基などが挙げられ、メチル基が好ましい。 Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, and t-butyl groups, with methyl being preferred.
シクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、及びビシクロ［１．１．１］ペンタニル基等が挙げられる。 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and bicyclo[1.1.1]pentanyl groups.
アリール基としては、フェニル基、トリル基、ナフチル基、キシリル基などが挙げられ、フェニル基が好ましい。 Aryl groups include phenyl, tolyl, naphthyl, and xylyl groups, with phenyl being preferred.
Ｒ１、Ｒ２、Ｒ３及びＲ４は、それぞれ独立に、水素原子、メチル基、またはフェニル基のいずれかであることが好ましく、水素原子であることがさらに好ましい。 R 1 , R 2 , R 3 and R 4 each independently preferably represent any one of a hydrogen atom, a methyl group, or a phenyl group, and more preferably a hydrogen atom.
上記式（１）中、Ｌ１及びＬ２は、それぞれ独立に、２価の連結基を示し、炭素数１～４のアルキレン基などが挙げられ、好ましくはエチレン基、またはプロピレン基を示し、より好ましくはエチレン基を示す。 In the above formula (1), L 1 and L 2 each independently represent a divalent linking group, such as an alkylene group having 1 to 4 carbon atoms, preferably an ethylene group or a propylene group, and more preferably an ethylene group.
上記式（１）中、ｏ及びｐはそれぞれ独立に０以上の整数を示し、好ましくは０～２示し、より好ましくは１を示す。 In the above formula (1), o and p each independently represent an integer of 0 or more, preferably 0 to 2, and more preferably 1.
上記式（１）中、Ｘは上記式（２）又は（３）で表される群より選ばれる少なくとも１つである。 In the above formula (1), X is at least one selected from the group represented by the above formula (2) or (3).
上記式（３）中、Ｙは２価の連結基を示し、炭素原子数１～２５の炭化水素基が挙げられ、炭化水素基としては、アルケン基、シクロアルケン基、アリーレン基を挙げることができる。 In the above formula (3), Y represents a divalent linking group, and examples of the hydrocarbon group include an alkene group, a cycloalkene group, and an arylene group.
アリーレン基としては、フェニレン基、ナフチレン基などが好ましく挙げられ、フェニレン基が特に好ましい。 Preferred examples of the arylene group include a phenylene group and a naphthylene group, with a phenylene group being particularly preferred.
上記式（１）において、芳香族炭化水素環を有するため屈折率を高める効果があり、またカルド構造を有するため複屈折を低減させる効果がある。 In the above formula (1), the presence of an aromatic hydrocarbon ring increases the refractive index, and the presence of a cardo structure reduces birefringence.
本発明の熱可塑性樹脂としては、ポリカーボネート、ポリエステルカーボネート及びポリエステルを挙げることができ、ポリカーボネート、ポリエステルカーボネートであることが好ましく、ポリエステルカーボネートであることがより好ましい。 Thermoplastic resins of the present invention include polycarbonate, polyester carbonate, and polyester, with polycarbonate and polyester carbonate being preferred, and polyester carbonate being more preferred.
《上記式（１）で表される構造を有する熱可塑性樹脂に使用するジオール成分》
本発明の熱可塑性樹脂の上記式（１）で表される構造単位に使用するジオール成分は、主に式（ａ）で表される化合物である。
<<Diol component used in thermoplastic resin having the structure represented by formula (1)>>
The diol component used in the structural unit represented by the above formula (1) of the thermoplastic resin of the present invention is mainly a compound represented by formula (a).
ジオール成分の上記式（ａ）において、Ｚ、Ｌ１、Ｌ２、ｏ、ｐ、Ｒ１、Ｒ２、Ｒ３及びＲ４は上記式（１）の各式と同様である。
以下、上記式（ａ）で表されるジオール成分の代表的具体例を示すが、本発明の上記式（ａ）に用いられる原料としては、それらによって限定されるものではない。
In the above formula (a) of the diol component, Z, L1 , L2 , o, p, R1 , R2 , R3 and R4 are the same as those in the above formula (1).
Representative specific examples of the diol component represented by the above formula (a) are shown below, but the raw materials used in the above formula (a) of the present invention are not limited to these.
具体的には、９，９－ビス（４－ヒドロキシフェニル）フルオレン、９，９－ビス（４－ヒドロキ－３－メチルフェニル）フルオレン、９，９－ビス（４－ヒドロキ－３－フェニルフェニル）フルオレン、９，９－ビス（４－（ヒドロキシメトキシ）フェニル）フルオレン、９，９－ビス（４－（ヒドロキシメトキシ）－３－メチルフェニル）フルオレン、９，９－ビス（４－（ヒドロキシメトキシ）－３－フェニルフェニル）フルオレン、９，９－ビス（４－（２－ヒドロキシエトキシ）フェニル）フルオレン、９，９－ビス（４－（２－ヒドロキシエトキシ）－３－メチルフェニル）フルオレン、９，９－ビス（４－（２－ヒドロキシエトキシ）－３－フェニルフェニル）フルオレン、９，９－ビス（４－（３－ヒドロキシプロポキシ）フェニル）フルオレン、９，９－ビス（４－（３－ヒドロキシプロポキシ）－３－メチルフェニル）フルオレン、９，９－ビス（４－（３－ヒドロキシプロポキシ）－３－フェニルフェニル）フルオレン、９，９－ビス（６－ヒドロキシ－２－ナフチル）フルオレン、９，９－ビス（６－ヒドロキシ－２－ナフチル）－２，７－ジメチルフルオレン、９，９－ビス（６－ヒドロキシ－２－ナフチル）－２，７－ジフェニルフルオレン、９，９－ビス（６－（２－ヒドロキシメトキシ）－２－ナフチル）フルオレン、９，９－ビス（６－（２－ヒドロキシメトキシ）－２－ナフチル）－２，７－ジメチルフルオレン、９，９－ビス（６－（２－ヒドロキシメトキシ）－２－ナフチル）－２，７－ジフェニルフルオレン、９，９－ビス（６－（２－ヒドロキシエトキシ）－２－ナフチル）フルオレン、９，９－ビス（６－（２－ヒドロキシエトキシ）－２－ナフチル）－２，７－ジメチルフルオレン、９，９－ビス（６－（２－ヒドロキシエトキシ）－２－ナフチル）－２，７－ジフェニルフルオレン、
９，９－ビス（６－（３－ヒドロキシプロポキシ）－２－ナフチル）フルオレン、９，９－ビス（６－（３－ヒドロキシプロポキシ）－２－ナフチル）－２，７－ジメチルフルオレン、９，９－ビス（６－（３－ヒドロキシプロポキシ）－２－ナフチル）－２，７－ジフェニルフルオレンが挙げられる。
Specifically, 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene, 9,9-bis(4-(hydroxymethoxy)phenyl)fluorene, 9,9-bis(4-(hydroxymethoxy)-3-methylphenyl)fluorene, 9,9-bis(4-(hydroxymethoxy)-3-phenylphenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)-3-methylphenyl)fluorene, 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorene, 9,9-bis(4-(3-hydroxypropoxy)phenyl)fluorene, 9,9-bis(4-(3-hydroxypropoxy)-3-methylphenyl)fluorene, 9,9-bis( 4-(3-hydroxypropoxy)-3-phenylphenyl)fluorene, 9,9-bis(6-hydroxy-2-naphthyl)fluorene, 9,9-bis(6-hydroxy-2-naphthyl)-2,7-dimethylfluorene, 9,9-bis(6-hydroxy-2-naphthyl)-2,7-diphenylfluorene, 9,9-bis(6-(2-hydroxymethoxy)-2-naphthyl)fluorene, 9,9-bis(6-(2-hydroxymethoxy) -2-naphthyl)-2,7-dimethylfluorene, 9,9-bis(6-(2-hydroxymethoxy)-2-naphthyl)-2,7-diphenylfluorene, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)fluorene, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-dimethylfluorene, 9,9-bis(6-(2-hydroxyethoxy)-2-naphthyl)-2,7-diphenylfluorene,
Examples of the fluorene include 9,9-bis(6-(3-hydroxypropoxy)-2-naphthyl)fluorene, 9,9-bis(6-(3-hydroxypropoxy)-2-naphthyl)-2,7-dimethylfluorene, and 9,9-bis(6-(3-hydroxypropoxy)-2-naphthyl)-2,7-diphenylfluorene.
これらは、１種を単独で使用しても、２種類以上を組み合わせて用いてもよい。
なかでも９，９－ビス（４－（３－ヒドロキシメトキシ）フェニル）フルオレン、９，９－ビス（４－（３－ヒドロキシエトキシ）フェニル）フルオレン、９，９－ビス（４－（２－ヒドロキプロポキシ）フェニル）フルオレンが好ましく、９，９－ビス（４－（２－ヒドロキシエトキシ）フェニル）フルオレンがより好ましい。９，９－ビス（４－（２－ヒドロキシエトキシ）フェニル）フルオレンは、その構造が高屈折率及び低複屈折性に寄与することに加え、酸化に強い安定した構造を有しており、長期耐熱性発現においても有利である。
These may be used alone or in combination of two or more.
Of these, 9,9-bis(4-(3-hydroxymethoxy)phenyl)fluorene, 9,9-bis(4-(3-hydroxyethoxy)phenyl)fluorene and 9,9-bis(4-(2-hydroxypropoxy)phenyl)fluorene are preferred, with 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene being more preferred. 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene has a structure that contributes to a high refractive index and low birefringence, and also has a stable structure that is resistant to oxidation, and is advantageous in terms of long-term heat resistance.
《上記式（ａ）以外のジオール成分》
本発明における熱可塑性樹脂は、上記式（ａ）で表されるジオール成分由来の上記式（１）の構造を有するが、本発明による効果を損なわない範囲で他のジオール成分由来の構造を含んでも良い。本発明における熱可塑性樹脂では、上記式（ａ）で表されるジオール成分を全ジオール成分中７０ｍｏｌ％以上占めることが好ましく、８０ｍｏｌ％以上であることがより好ましい。
Diol component other than the above formula (a)
The thermoplastic resin in the present invention has the structure of the above formula (1) derived from the diol component represented by the above formula (a), but may contain structures derived from other diol components within a range that does not impair the effects of the present invention. In the thermoplastic resin in the present invention, the diol component represented by the above formula (a) preferably accounts for 70 mol % or more, more preferably 80 mol % or more, of the total diol components.
他のジオール成分としては、エチレングリコール、プロパンジオール、ブタンジオール、ペンタンジオール、ヘキサンジオール、ヘプタンジオール、オクタンジオール、ノナンジオール、トリシクロ［５．２．１．０２，６］デカンジメタノール、シクロヘキサン－１，４－ジメタノール、デカリン－２，６－ジメタノール、ノルボルナンジメタノール、ペンタシクロペンタデカンジメタノール、シクロペンタン－１，３－ジメタノール、スピログリコール、イソソルビド、イソマンニド、イソイジド、ヒドロキノン、レゾルシノール、ジヒドロキシナフタレン、２，２－ビス（４－ヒドロキシフェニル）プロパン、２，２－ビス（３－メチル－４－ヒドロキシフェニル）プロパン、１，１－ビス（４－ヒドロキシフェニル）－１－フェニルエタン、１，３－ビス（２－（４－ヒドロキシフェニル）－２－プロピル）ベンゼン、１，１－ビス（４－ヒドロキシフェニル）－３，３，５－トリメチルシクロヘキサン、１，１－ビス（４－ヒドロキシフェニル）シクロヘキサン、ビス（４－ヒドロキシフェニル）ジフェニルメタン、１，１－ビス（４－ヒドロキシフェニル）デカン、ビス（４－ヒドロキシフェニル）スルフィド、ビス（４－ヒドロキシ－３－メチルフェニル）スルフィド、ビフェノール、２，２’－ビス（１－ヒドロキシメトキシ）－１，１’－ビナフタレン、２，２’－ビス（２－ヒドロキシエトキシ）－１，１’－ビナフタレン、２，２’－ビス（３－ヒドロキシプロピルオキシ）－１，１’－ビナフタレン、２，２’－ビス（４－ヒドロキシブトキシ）－１，１’－ビナフタレン、１，１’－ビ－２－ナフトール等が例示され、これらは単独または二種類以上組み合わせて用いても良い。 Other diol components include ethylene glycol, propanediol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, tricyclo[5.2.1.0 2,6 ] decanedimethanol, cyclohexane-1,4-dimethanol, decalin-2,6-dimethanol, norbornane dimethanol, pentacyclopentadecanedimethanol, cyclopentane-1,3-dimethanol, spiroglycol, isosorbide, isomannide, isoidide, hydroquinone, resorcinol, dihydroxynaphthalene, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, Examples include 1,1-bis(4-hydroxyphenyl)cyclohexane, bis(4-hydroxyphenyl)diphenylmethane, 1,1-bis(4-hydroxyphenyl)decane, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxy-3-methylphenyl)sulfide, biphenol, 2,2'-bis(1-hydroxymethoxy)-1,1'-binaphthalene, 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene, 2,2'-bis(3-hydroxypropyloxy)-1,1'-binaphthalene, 2,2'-bis(4-hydroxybutoxy)-1,1'-binaphthalene, and 1,1'-bi-2-naphthol, which may be used alone or in combination of two or more.
《上記式（１）で表される構造を有する熱可塑性樹脂に使用するジカルボン酸成分》
本発明の熱可塑性樹脂がポリエステルカーボネート、ポリエステルなどの場合に使用するジカルボン酸成分は、主に式（ｂ）で表される化合物、またはそのエステル形成誘導体である。
<<Dicarboxylic acid component used in thermoplastic resin having the structure represented by the above formula (1)>>
When the thermoplastic resin of the present invention is a polyester carbonate, polyester or the like, the dicarboxylic acid component used is mainly a compound represented by formula (b) or an ester-forming derivative thereof.
上記式（ｂ）において、Ｙは上記式（３）と同様である。
以下、上記式（ｂ）で表されるジカルボン酸またはそのエステル形成性誘導体の代表的具体例を示すが、本発明の上記式（ｂ）に用いられる原料としては、それらによって限定されるものではない。
In the above formula (b), Y is the same as in the above formula (3).
Representative examples of the dicarboxylic acid represented by the above formula (b) or its ester-forming derivative are shown below, but the raw material used in the above formula (b) of the present invention is not limited thereto.
ジカルボン酸成分としては、マロン酸、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、メチルマロン酸、エチルマロン酸等の脂肪族ジカルボン酸成分、フタル酸、イソフタル酸、テレフタル酸等の単環式芳香族ジカルボン酸成分、２，６－ナフタレンジカルボン酸、２，７－ナフタレンジカルボン酸、２，３－ナフタレンジカルボン酸、１，４－ナフタレンジカルボン酸、１，８－ナフタレンジカルボン酸、アントラセンジカルボン酸、フェナントレンジカルボン酸、９，９－ビス（カルボキシメチル）フルオレン、９，９－ビス（２－カルボキシエチル）フルオレン、９，９－ビス（１－カルボキシエチル）フルオレン、９，９－ビス（１－カルボキシプロピル）フルオレン、９，９－ビス（２－カルボキシプロピル）フルオレン、９，９－ビス（２－カルボキシ－１－メチルエチル）フルオレン、９，９－ビス（２－カルボキシ－１－メチルプロピル）フルオレン、９，９－ビス（２－カルボキシブチル）フルオレン、９，９－ビス（２－カルボキシ－１－メチルブチル）フルオレン、９，９－ビス（５－カルボキシペンチル）フルオレン、９，９－ビス（カルボキシシクロヘキシル）フルオレン等の多環式芳香族ジカルボン酸成分、１，４－シクロヘキサンジカルボン酸、２，６－デカリンジカルボン酸等の脂環族ジカルボン酸成分が挙げられ、２，６－ナフタレンジカルボン酸、テレフタル酸が好ましく、テレフタル酸がより好ましい。また、エステル形成性誘導体としては酸クロライドや、メチルエステル、エチルエステル、フェニルエステル等のエステル類を用いてもよく、２，６－ナフタレンジカルボン酸ジメチル、テレフタル酸ジメチルが好ましく、テレフタル酸ジメチルがより好ましい。テレフタル酸ジメチルは酸化に強い安定した構造を有しており、長期耐熱性発現に有利である。これらは、１種を単独で使用しても、２種類以上を組み合わせて用いてもよい。 Dicarboxylic acid components include aliphatic dicarboxylic acid components such as malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, methylmalonic acid, and ethylmalonic acid, monocyclic aromatic dicarboxylic acid components such as phthalic acid, isophthalic acid, and terephthalic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, anthracene dicarboxylic acid, phenanthrene dicarboxylic acid, 9,9-bis(carboxymethyl)fluorene, 9,9-bis(2-carboxyethyl)fluorene, 9,9-bis(1-carboxyethyl)fluorene, and 9,9-bis(1-carboxypropyl)fluorene. Examples of the dicarboxylic acid component include polycyclic aromatic dicarboxylic acid components such as 9,9-bis(2-carboxypropyl)fluorene, 9,9-bis(2-carboxy-1-methylethyl)fluorene, 9,9-bis(2-carboxy-1-methylpropyl)fluorene, 9,9-bis(2-carboxybutyl)fluorene, 9,9-bis(2-carboxy-1-methylbutyl)fluorene, 9,9-bis(5-carboxypentyl)fluorene, and 9,9-bis(carboxycyclohexyl)fluorene; and alicyclic dicarboxylic acid components such as 1,4-cyclohexanedicarboxylic acid and 2,6-decalindicarboxylic acid. Of these, 2,6-naphthalenedicarboxylic acid and terephthalic acid are preferred, and terephthalic acid is more preferred. In addition, examples of the ester-forming derivative include acid chlorides, and esters such as methyl esters, ethyl esters, and phenyl esters. Of these, dimethyl 2,6-naphthalenedicarboxylate and dimethyl terephthalate are preferred, and dimethyl terephthalate is more preferred. Dimethyl terephthalate has a stable structure that is resistant to oxidation, and is advantageous in terms of long-term heat resistance. These may be used alone or in combination of two or more types.
《ポリカーボネート樹脂の製造方法》
ポリカーボネート樹脂は、それ自体公知の反応手段、例えばジヒドロキシ化合物成分とカーボネート前駆物質を界面重合法または溶融重合法によって反応させて得られる。ポリカーボネート樹脂を製造するに当たっては、必要に応じて触媒、末端停止剤、酸化防止剤等を使用してもよい。国際公開第２０１７／０７８０７０号の記載を参考に製造することができる。
<<Production method of polycarbonate resin>>
The polycarbonate resin is obtained by reacting a dihydroxy compound component with a carbonate precursor by a known reaction means, for example, an interfacial polymerization method or a melt polymerization method. When producing the polycarbonate resin, a catalyst, a terminal terminator, an antioxidant, etc. may be used as necessary. It can be produced by referring to the description in International Publication No. 2017/078070.
溶融重合法においては重合速度を速めるために、重合触媒を用いることができ、かかる重合触媒としては、アルカリ金属化合物、アルカリ土類金属化合物、含窒素化合物、等が挙げられる。このような化合物としては、アルカリ金属やアルカリ土類金属の、有機酸塩、無機塩、酸化物、水酸化物、水素化物、アルコキシド、４級アンモニウムヒドロキシド等が好ましく用いられ、これらの化合物は単独もしくは組み合わせて用いることができる。 In the melt polymerization method, a polymerization catalyst can be used to increase the polymerization rate. Examples of such polymerization catalysts include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds. As such compounds, organic acid salts, inorganic salts, oxides, hydroxides, hydrides, alkoxides, and quaternary ammonium hydroxides of alkali metals and alkaline earth metals are preferably used, and these compounds can be used alone or in combination.
アルカリ金属化合物としては、水酸化ナトリウム、水酸化カリウム、水酸化セシウム、水酸化リチウム、炭酸水素ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、炭酸リチウム、酢酸ナトリウム、酢酸カリウム、酢酸セシウム、酢酸リチウム、ステアリン酸ナトリウム、ステアリン酸カリウム、ステアリン酸セシウム、ステアリン酸リチウム、水素化ホウ素ナトリウム、安息香酸ナトリウム、安息香酸カリウム、安息香酸セシウム、安息香酸リチウム、リン酸水素２ナトリウム、リン酸水素２カリウム、リン酸水素２リチウム、フェニルリン酸２ナトリウム、ビスフェノールＡの２ナトリウム塩、２カリウム塩、２セシウム塩、２リチウム塩、フェノールのナトリウム塩、カリウム塩、セシウム塩、リチウム塩等が例示され、水酸化ナトリウム、水酸化カリウム、水酸化セシウム、水酸化リチウム、炭酸水素ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、炭酸リチウムが好ましく、炭酸水素ナトリウムがより好ましい。 Examples of alkali metal compounds include sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium hydrogen carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, cesium acetate, lithium acetate, sodium stearate, potassium stearate, cesium stearate, lithium stearate, sodium borohydride, sodium benzoate, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, disodium phenylphosphate, disodium salt, dipotassium salt, dicesium salt, dilithium salt of bisphenol A, sodium salt, potassium salt, cesium salt, lithium salt of phenol, etc., and sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium hydrogen carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate are preferred, and sodium hydrogen carbonate is more preferred.
《ポリエステルカーボネート樹脂の製造方法》
ポリエステルカーボネート樹脂は、それ自体公知の反応手段、例えばジヒドロキシ化合物成分およびジカルボン酸またはそのエステル形成性誘導体と、ホスゲンやカーボネートエステルなどのカーボネート前駆物質とを反応させることにより製造することができる。特許文献１や２の記載を参考に製造することができる。
<Production method of polyester carbonate resin>
The polyester carbonate resin can be produced by a reaction means known per se, for example, by reacting a dihydroxy compound component and a dicarboxylic acid or an ester-forming derivative thereof with a carbonate precursor such as phosgene or a carbonate ester. The production can be carried out by referring to the descriptions in Patent Documents 1 and 2.
溶融重合法においては重合速度を速めるために、重合触媒を用いることができ、かかる重合触媒として、アルミニウム又はその化合物とリン化合物とからなる触媒を用いてもよい。その場合、使用する全モノマー単位の合計１ｍｏｌに対して、８０μｍｏｌ以上、９０μｍｏｌ以上、１００μｍｏｌ以上であってもよく、１０００μｍｏｌ以下、８００μｍｏｌ以下、６００μｍｏｌ以下で使用することができる。 In the melt polymerization method, a polymerization catalyst can be used to increase the polymerization rate, and a catalyst consisting of aluminum or a compound thereof and a phosphorus compound can be used as the polymerization catalyst. In that case, the amount of the catalyst may be 80 μmol or more, 90 μmol or more, or 100 μmol or more, or 1000 μmol or less, 800 μmol or less, or 600 μmol or less, per 1 mol of the total of all monomer units used.
アルミニウム塩としては、アルミニウムの有機酸塩及び無機酸塩を挙げることができる。アルミニウムの有機酸塩としては、例えば、アルミニウムのカルボン酸塩を挙げることができ、具体的にはギ酸アルミニウム、酢酸アルミニウム、プロピオン酸アルミニウム、蓚酸アルミニウム、アクリル酸アルミニウム、ラウリン酸アルミニウム、ステアリン酸アルミニウム、安息香酸アルミニウム、トリクロロ酢酸アルミニウム、乳酸アルミニウム、クエン酸アルミニウム、及びサリチル酸アルミニウムを挙げることができる。アルミニウムの無機酸塩としては、例えば、塩化アルミニウム、水酸化アルミニウム、水酸化塩化アルミニウム、炭酸アルミニウム、リン酸アルミニウム、及びホスホン酸アルミニウムを挙げることができる。アルミニウムキレート化合物としては、例えば、アルミニウムアセチルアセトネート、アルミニウムアセチルアセテート、アルミニウムエチルアセトアセテート、及びアルミニウムエチルアセトアセテートジｉｓｏ－プロポキシドを好ましく挙げることができ、アルミニウムアセチルアセトネートがさらに好ましい。 Examples of aluminum salts include organic and inorganic salts of aluminum. Examples of organic salts of aluminum include aluminum carboxylates, specifically aluminum formate, aluminum acetate, aluminum propionate, aluminum oxalate, aluminum acrylate, aluminum laurate, aluminum stearate, aluminum benzoate, aluminum trichloroacetate, aluminum lactate, aluminum citrate, and aluminum salicylate. Examples of inorganic salts of aluminum include aluminum chloride, aluminum hydroxide, aluminum hydroxide chloride, aluminum carbonate, aluminum phosphate, and aluminum phosphonate. Examples of aluminum chelate compounds include aluminum acetylacetonate, aluminum acetylacetate, aluminum ethylacetoacetate, and aluminum ethylacetoacetate diso-propoxide, with aluminum acetylacetonate being more preferred.
リン化合物としては、例えば、ホスホン酸系化合物、ホスフィン酸系化合物、ホスフィンオキサイド系化合物、亜ホスホン酸系化合物、亜ホスフィン酸系化合物、及びホスフィン系化合物を挙げることができ、これらの中でも特に、ホスホン酸系化合物、ホスフィン酸系化合物、及びホスフィンオキサイド系化合物を好ましく挙げることができ、特にホスホン酸系化合物が好ましい。 Examples of phosphorus compounds include phosphonic acid compounds, phosphinic acid compounds, phosphine oxide compounds, phosphonous acid compounds, phosphineous acid compounds, and phosphine compounds. Among these, phosphonic acid compounds, phosphinic acid compounds, and phosphine oxide compounds are particularly preferred, with phosphonic acid compounds being particularly preferred.
《ポリエステル樹脂の製造方法》
ポリエステル樹脂である場合はそれ自体公知の反応手段、例えばジヒドロキシ化合物成分とジカルボン酸またはそのエステル形成性誘導体とをエステル化反応もしくはエステル交換反応させ、得られた反応生成物を重縮合反応させ、所望の分子量の高分子量体とすればよい。特開２０１６―６９６４３号公報の記載を参考に製造することができる。
<<Production method of polyester resin>>
In the case of a polyester resin, a known reaction method may be used, for example, an esterification reaction or an ester exchange reaction between a dihydroxy compound component and a dicarboxylic acid or its ester-forming derivative, and the resulting reaction product may be subjected to a polycondensation reaction to obtain a polymer having a desired molecular weight. The polyester resin may be produced by referring to the description in JP-A-2016-69643.
《離型剤》
本発明の熱可塑性樹脂組成物は、離型剤を含み、離型剤の含有量として、熱可塑性樹脂組成物中に１～４０００ｐｐｍ含むことが好ましく、１０～３５００ｐｐｍ含むことがより好ましく、５０～３０００ｐｐｍ含むことがさらに好ましく、８０～２５００ｐｐｍ含むことがよりさらに好ましく、３００～２０００ｐｐｍ含むことが特に好ましく、７００ｐｐｍ～２０００ｐｐｍ含むことが最も好ましい。発明者は離型剤を上記範囲内で添加することで、離型性を向上させることに加え、高い長期耐熱性を発揮させることができることを見出した。長期耐熱性は、酸化劣化を抑制することで向上すると考えられる。よって、離型剤が樹脂中に存在することで、樹脂混錬時及び成形加工時の摩擦等からポリマー鎖を保護し負荷を低減する効果が奏され、酸化劣化を進行させるラジカル・過酸化物等の不安定構造生成が抑えられる為、長期耐熱性が向上すると推測される。併せて、樹脂混錬時及び成形加工時の酸化劣化が抑制されることで初期色相も良化する効果が奏される。
さらに、上記範囲内であれば離型剤の量が多すぎることによる屈折率の低下、全光線透過率の低下、金型付着汚れを抑制することができる。なお本書において「ｐｐｍ」は「質量ｐｐｍ」を意味する。
"Release agent"
The thermoplastic resin composition of the present invention contains a release agent, and the content of the release agent in the thermoplastic resin composition is preferably 1 to 4000 ppm, more preferably 10 to 3500 ppm, even more preferably 50 to 3000 ppm, even more preferably 80 to 2500 ppm, particularly preferably 300 to 2000 ppm, and most preferably 700 ppm to 2000 ppm. The inventors have found that by adding the release agent within the above range, it is possible to improve the releasability and also to exhibit high long-term heat resistance. It is believed that the long-term heat resistance is improved by suppressing oxidative deterioration. Therefore, the presence of the release agent in the resin has the effect of protecting the polymer chain from friction and the like during resin kneading and molding processing, reducing the load, and suppressing the generation of unstable structures such as radicals and peroxides that promote oxidative deterioration, so that it is presumed that the long-term heat resistance is improved. In addition, the effect of improving the initial color is achieved by suppressing oxidative deterioration during resin kneading and molding processing.
Furthermore, within the above range, it is possible to suppress a decrease in refractive index, a decrease in total light transmittance, and mold contamination caused by an excessive amount of the mold release agent. In this specification, "ppm" means "ppm by mass."
離型剤として、一種の離型剤を用いても良く複数種類の離型剤を組み合わせても良い。複数種類の離型剤を用いる場合は、離型剤の合計量が上記の数値範囲となるように調整すればよい。 As the release agent, one type of release agent may be used, or multiple types of release agents may be combined. When multiple types of release agents are used, the total amount of the release agents may be adjusted so that it falls within the above numerical range.
本発明に用いる離型剤としては、国際公開第２０１１／０１０７４１号に記載されたものが好ましく挙げられる。特に好ましい離型剤としては、ステアリン酸モノグリセリド、ステアリン酸トリグリセリド、ペンタエリスリトールテトラステアレート、ステアリン酸トリグリセリドとステアリルステアレートの混合物が好ましく用いられる。また、離型剤中の前記エステルの量は、離型剤を１００質量％とした時、９０質量％以上が好ましく、９５質量％以上がより好ましい。 Preferred examples of the release agent used in the present invention include those described in International Publication No. 2011/010741. Particularly preferred release agents include stearic acid monoglyceride, stearic acid triglyceride, pentaerythritol tetrastearate, and a mixture of stearic acid triglyceride and stearyl stearate. The amount of the ester in the release agent is preferably 90% by mass or more, and more preferably 95% by mass or more, when the release agent is taken as 100% by mass.
《酸化防止剤》
本発明の熱可塑性樹脂組成物において、熱可塑性樹脂組成物中に含まれる酸化防止剤の含有量は０～３００ｐｐｍである。熱可塑性樹脂組成物中に含まれる酸化防止剤の量は０～２００ｐｐｍであることが好ましく、０～１００ｐｐｍであることがより好ましく、０～５０ｐｐｍであることがさらに好ましく、０～１０ｐｐｍであることがよりさらに好ましく、０～１ｐｐｍであることが特に好ましく、０ｐｐｍであることが最も好ましい。酸化防止剤が上記範囲内であることで、長期耐熱性に優れる。長期耐熱性は、酸化劣化を抑制することで向上するため、酸化防止剤のように容易に変化可能な構造を少なくし、酸化に強い安定な化学構造で熱可塑性樹脂組成物を構築することで長期耐熱性を向上させることができる。
"Antioxidant"
In the thermoplastic resin composition of the present invention, the content of the antioxidant contained in the thermoplastic resin composition is 0 to 300 ppm. The amount of the antioxidant contained in the thermoplastic resin composition is preferably 0 to 200 ppm, more preferably 0 to 100 ppm, even more preferably 0 to 50 ppm, even more preferably 0 to 10 ppm, particularly preferably 0 to 1 ppm, and most preferably 0 ppm. By having the antioxidant within the above range, the long-term heat resistance is excellent. Since the long-term heat resistance is improved by suppressing oxidative deterioration, the long-term heat resistance can be improved by reducing the structure that can be easily changed such as the antioxidant and constructing the thermoplastic resin composition with a stable chemical structure that is resistant to oxidation.
具体的な酸化防止剤としては、国際公開第２０１１／０１０７４１号に記載されたものが挙げられ、リン系酸化防止剤、硫黄系酸化防止剤及びヒンダードフェノール系酸化防止剤等がある。 Specific examples of antioxidants include those described in WO 2011/010741, such as phosphorus-based antioxidants, sulfur-based antioxidants, and hindered phenol-based antioxidants.
また、リン系酸化防止剤としては、トリス（２，４－ジ－ｔｅｒｔ－ブチルフェニル）ホスファイト、ビス（２，６－ジ－ｔｅｒｔ－ブチル－４－メチルフェニル）ペンタエリスリトールジホスファイト、テトラキス（２，４－ジ－ｔｅｒｔ－ブチルフェニル）－４，４’－ビフェニレンジホスホナイト、ジスステアリルペンタエリスリトールジホスファイト、ビス（２，４－ジクミルフェニル）ペンタエリスリトールジホスファイト、環状ネオペンタンテトライルビス（２，６－ジ－ｔｅｒｔ－ブチル－４－メチルフェニルホスファイト）、ビス（２，４－ジ－ｔｅｒｔ－ブチルフェニル）ペンタエリスリトールジホスファイトが挙げられる。 Examples of phosphorus-based antioxidants include tris(2,4-di-tert-butylphenyl)phosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, tetrakis(2,4-di-tert-butylphenyl)-4,4'-biphenylene diphosphonite, distearyl pentaerythritol diphosphite, bis(2,4-dicumylphenyl)pentaerythritol diphosphite, cyclic neopentanetetraylbis(2,6-di-tert-butyl-4-methylphenyl phosphite), and bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite.
また、硫黄系酸化防止剤としては、ペンタエリスリトール－テトラキス（３－ラウリルチオプロピオネート）が挙げられる。 Another sulfur-based antioxidant is pentaerythritol-tetrakis(3-laurylthiopropionate).
また、ヒンダードフェノール系酸化防止剤としては、オクタデシル－３－（３，５－ジ－ｔｅｒｔ－ブチル－４－ヒドロキシフェニル）プロピオネート、ペンタエリスリトール－テトラキス［３－（３，５－ジ－ｔｅｒｔ－ブチル－４－ヒドロキシフェニル）プロピオネート］、トリエチレングリコール－ビス［３－（３－ｔｅｒｔ－ブチル－５－メチル－４－ヒドロキシフェニル）プロピオネート］、１，６－ヘキサンジオール－ビス［３－（３，５－ジ－ｔｅｒｔ－ブチル－４－ヒドロキシフェニル）プロピオネート］、１，３，５－トリメチル－２，４，６－トリス（３，５－ジ－ｔｅｒｔ－ブチル－４－ヒドロキシベンジル）ベンゼン
、Ｎ，Ｎ－ヘキサメチレンビス（３，５－ジ－ｔｅｒｔ－ブチル－４－ヒドロキシ－ヒドロシンナマイド）、３，５－ジ－ｔｅｒｔ－ブチル－４－ヒドロキシ－ベンジルホスホネート－ジエチルエステル、トリス（３，５－ジ－ｔｅｒｔ－ブチル－４－ヒドロキシベンジル）イソシアヌレート、３，９－ビス｛１，１－ジメチル－２－［β－（３－ｔｅｒｔ－ブチル－４－ヒドロキシ－５－メチルフェニル）プロピオニルオキシ］エチル｝－２，４，８，１０－テトラオキサスピロ（５，５）ウンデカンが挙げられる。
酸化防止剤の合計量が上記の数値範囲であれば、複数種類の酸化防止剤を含んでも良い。
Examples of the hindered phenol antioxidant include octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 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], 1,3,5-trimethyl-2,4,6-tris(3,5 -di-tert-butyl-4-hydroxybenzyl)benzene, N,N-hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamide), 3,5-di-tert-butyl-4-hydroxy-benzylphosphonate-diethyl ester, tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 3,9-bis{1,1-dimethyl-2-[β-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]ethyl}-2,4,8,10-tetraoxaspiro(5,5)undecane.
As long as the total amount of the antioxidants is within the above range, multiple types of antioxidants may be included.
《任意の添加剤》
本発明の熱可塑性樹脂組成物には、必要に応じて、紫外線吸収剤、帯電防止剤、難燃剤、可塑剤、充填剤、滑剤、界面活性剤、抗菌剤、重合金属不活性化剤、相溶化剤、着色剤などの添加剤を適宜添加して樹脂組成物として用いることができる。
Optional Additives
The thermoplastic resin composition of the present invention can be used as a resin composition by appropriately adding additives such as ultraviolet absorbers, antistatic agents, flame retardants, plasticizers, fillers, lubricants, surfactants, antibacterial agents, polymerized metal deactivators, compatibilizers, and colorants, as necessary.
紫外線吸収剤としては、ベンゾトリアゾール系紫外線吸収剤、ベンゾフェノン系紫外線吸収剤、トリアジン系紫外線吸収剤、環状イミノエステル系紫外線吸収剤及びシアノアクリレート系からなる群より選ばれた少なくとも１種の紫外線吸収剤が好ましい。 As the ultraviolet absorber, at least one ultraviolet absorber selected from the group consisting of benzotriazole-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers, triazine-based ultraviolet absorbers, cyclic iminoester-based ultraviolet absorbers, and cyanoacrylate-based ultraviolet absorbers is preferred.
ベンゾトリアゾール系紫外線吸収剤において、より好ましくは、２－（２－ヒドロキシ－５－ｔｅｒｔ－オクチルフェニル）ベンゾトリアゾ－ル、２，２’－メチレンビス［４－（１，１，３，３－テトラメチルブチル）－６－（２Ｈ－ベンゾトリアゾール－２－イル）フェノール］である。 Among benzotriazole-based ultraviolet absorbers, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole and 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazol-2-yl)phenol] are more preferred.
ベンゾフェノン系紫外線吸収剤としては、２－ヒドロキシ－４－ｎ－ドデシルオキシベンソフェノン、２－ヒドロキシ－４－メトキシ－２’－カルボキシベンゾフェノンが挙げられる。 Benzophenone-based UV absorbers include 2-hydroxy-4-n-dodecyloxybenzophenone and 2-hydroxy-4-methoxy-2'-carboxybenzophenone.
トリアジン系紫外線吸収剤としては、２－（４，６－ジフェニル－１，３，５－トリアジン－２－イル）－５－［（ヘキシル）オキシ］－フェノール、２－（４，６－ビス（２．４－ジメチルフェニル）－１，３，５－トリアジン－２－イル）－５－［（オクチル）オキシ］－フェノール等が挙げられる。 Examples of triazine-based ultraviolet absorbers 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, etc.
環状イミノエステル系紫外線吸収剤としては、特に２，２’－ｐ－フェニレンビス（３，１－ベンゾオキサジン－４－オン）が好適である。 As a cyclic iminoester-based UV absorber, 2,2'-p-phenylenebis(3,1-benzoxazin-4-one) is particularly suitable.
シアノアクリレート系紫外線吸収剤としては、１，３－ビス－［（２’－シアノ－３’，３’－ジフェニルアクリロイル）オキシ］－２，２－ビス［（２－シアノ－３，３－ジフェニルアクリロイル）オキシ］メチル）プロパン、及び１，３－ビス－［（２－シアノ－３，３－ジフェニルアクリロイル）オキシ］ベンゼン等が挙げられる。 Examples of cyanoacrylate-based UV absorbers include 1,3-bis-[(2'-cyano-3',3'-diphenylacryloyl)oxy]-2,2-bis[(2-cyano-3,3-diphenylacryloyl)oxy]methyl)propane and 1,3-bis-[(2-cyano-3,3-diphenylacryloyl)oxy]benzene.
紫外線吸収剤の配合量は、熱可塑性樹脂組成物に対して好ましくは１０００～３００００ｐｐｍであり、かかる配合量の範囲であれば、用途に応じ、熱可塑性樹脂組成物の成形品に十分な耐候性を付与することが可能である。 The amount of ultraviolet absorber to be blended is preferably 1,000 to 30,000 ppm relative to the thermoplastic resin composition, and within this blending range, it is possible to impart sufficient weather resistance to molded articles of the thermoplastic resin composition depending on the application.
《熱可塑性樹脂組成物の製造方法》
本発明の熱可塑性樹脂組成物は、式（１）で表される構造を有する熱可塑性樹脂に離型剤及びその他添加剤を添加し、溶融混錬することで製造される。
<<Method for producing thermoplastic resin composition>>
The thermoplastic resin composition of the present invention is produced by adding a release agent and other additives to a thermoplastic resin having a structure represented by formula (1), and melt-kneading the mixture.
各種添加剤の添加方法は特に限定されず、任意の方法で行ってよい。例えば、熱可塑性樹脂の重合段階で加えてもよいし、熱可塑性樹脂を重合した後に入れても良い。熱可塑性樹脂に各種添加剤を添加する場合、熱可塑性樹脂を入れた容器に後から添加剤を添加してもよいし、予め添加剤を入れた容器に後から熱可塑性樹脂を入れてもよいし、熱可塑性樹脂と添加剤を同時に一つの容器に入れてもよい。具体的には、ターンブルミキサー、ヘンシェルミキサー、リボンブレンダー、スーパーミキサー、ロールミキサーまたはタンブラーミキサーを用いて、ペレット状の熱可塑性樹脂に添加剤を付着させてもよい。このような添加方法によれば、熱可塑性樹脂中に添加剤を均一に分散することができるため好ましい。またペレット状の熱可塑性樹脂と熱可塑性樹脂の一部へ高濃度で添加剤を溶融混錬したペレット同士を混合してもよい。熱可塑性樹脂へ各種添加剤を添加した後、これらを溶融混錬する方法は特に限定されず、任意の方法で行って良い。例えば、溶融混錬は一軸または二軸押出機、バンバリーミキサー、スタティックミキサー等の公知の混錬方法で行ってもよい。ペレット化の方法は特に限定されず、任意の方法を用いることができる。 The method of adding the various additives is not particularly limited, and may be any method. For example, they may be added at the polymerization stage of the thermoplastic resin, or may be added after the thermoplastic resin is polymerized. When adding various additives to the thermoplastic resin, the additives may be added later to a container containing the thermoplastic resin, the thermoplastic resin may be added later to a container containing the additives in advance, or the thermoplastic resin and the additives may be placed in one container at the same time. Specifically, the additives may be attached to the pellet-shaped thermoplastic resin using a Turnbull mixer, a Henschel mixer, a ribbon blender, a super mixer, a roll mixer, or a tumbler mixer. This method of addition is preferable because it allows the additives to be uniformly dispersed in the thermoplastic resin. In addition, pellet-shaped thermoplastic resin and pellets in which additives are melt-kneaded at a high concentration in a part of the thermoplastic resin may be mixed together. After adding various additives to the thermoplastic resin, the method of melt-kneading them is not particularly limited, and may be any method. For example, melt-kneading may be performed by a known kneading method such as a single-screw or twin-screw extruder, a Banbury mixer, or a static mixer. The method of pelletization is not particularly limited, and any method can be used.
《熱可塑性樹脂組成物の特性》
本発明の熱可塑性樹脂組成物は、優れた長期耐熱性を有する。本明細書において、「優れた長期耐熱性」とは射出成形物が長期にわたる高温暴露の前後で黄変が小さいことを示す。長期耐熱性は、熱可塑性樹脂組成物を射出成形し、得られた成形物に乾燥雰囲気下１２０℃で５００時間暴露する乾熱試験を行い、試験前後での色の変化である乾熱黄変ΔＹＩを測定することで評価することができる。本発明の熱可塑性樹脂組成物の２ｍｍ厚成形物の乾熱黄変ΔＹＩは、０．００～０．４７であることが好ましく、０．００～０．４０であることがより好ましく、０．００～０．３５であることがさらに好ましく、０．００～０．３０であることがよりさらに好ましく、０．００～０．２１であることがさらに好ましく、０．００～０．１５であることが最も好ましい。乾熱黄変ΔＹＩが上記範囲内であると各種透明部材としての使用範囲が限定されず好ましい。
<Characteristics of Thermoplastic Resin Composition>
The thermoplastic resin composition of the present invention has excellent long-term heat resistance. In this specification, "excellent long-term heat resistance" means that the injection molded product has little yellowing before and after long-term exposure to high temperatures. The long-term heat resistance can be evaluated by injection molding the thermoplastic resin composition, exposing the obtained molded product to 120°C in a dry atmosphere for 500 hours in a dry heat test, and measuring the dry heat yellowing ΔYI, which is the change in color before and after the test. The dry heat yellowing ΔYI of a 2 mm thick molded product of the thermoplastic resin composition of the present invention is preferably 0.00 to 0.47, more preferably 0.00 to 0.40, even more preferably 0.00 to 0.35, even more preferably 0.00 to 0.30, even more preferably 0.00 to 0.21, and most preferably 0.00 to 0.15. If the dry heat yellowing ΔYI is within the above range, the range of use as various transparent members is not limited and is preferable.
本発明の熱可塑性樹脂組成物は、高い屈折率ｎｄと低いアッベ数νｄを有する。本発明の熱可塑性樹脂組成物の屈折率ｎｄは、温度：２０℃、波長：５８９ｎｍで測定した場合に、１．６００以上であり、１．６１０以上、１．６２０以上または１．６３０以上であってもよく、１．６８０以下、１．６７０以下、１．６６０以下、１．６５０以下であってもよい。例えば、本発明の熱可塑性樹脂の屈折率ｎｄは、１．６３５～１．６５０であり、１．６３５～１．６４８が好ましく、１．６３５～１．６４６がより好ましく、１．６３６～１．６４４がさらに好ましく、１．６３６～１．６４２が特に好ましく、１．６３６～１．６４１が最も好ましい。屈折率が上記範囲内の場合、光学レンズの球面収差を低減でき、さらに光学レンズの焦点距離を短くすることができる。 The thermoplastic resin composition of the present invention has a high refractive index nd and a low Abbe number νd. The refractive index nd of the thermoplastic resin composition of the present invention is 1.600 or more, and may be 1.610 or more, 1.620 or more, or 1.630 or more, or may be 1.680 or less, 1.670 or less, 1.660 or less, or 1.650 or less, when measured at a temperature of 20°C and a wavelength of 589 nm. For example, the refractive index nd of the thermoplastic resin of the present invention is 1.635 to 1.650, preferably 1.635 to 1.648, more preferably 1.635 to 1.646, even more preferably 1.636 to 1.644, particularly preferably 1.636 to 1.642, and most preferably 1.636 to 1.641. When the refractive index is within the above range, the spherical aberration of the optical lens can be reduced, and the focal length of the optical lens can be shortened.
本発明の熱可塑性樹脂組成物のアッベ数νｄは、１７．０以上、１８．０以上、１９．０以上、２０．０以上、又は２１．０以上であってもよく、３０．０以下、２９．０以下、２８．０以下、２７．０以下、２６．０以下、又は２５．０以下であってもよい。例えば、本発明の熱可塑性樹脂組成物のアッベ数νｄは、２１．０～２６．０、２１．５～２５．５、２２．０～２５．０であってもよい。
ここで、アッベ数νｄは、温度：２０℃、波長：４８６．１３ｎｍ、５８７．５６ｎｍ、６５６．２７ｎｍの屈折率から、下記式を用いて算出する：
νｄ＝（ｎｄ－１）／（ｎＦ－ｎＣ）
ｎｄ：波長５８７．５６ｎｍでの屈折率、
ｎＦ：波長４８６．１３ｎｍでの屈折率、
ｎＣ：波長６５６．２７ｎｍでの屈折率を意味する。
The Abbe number vd of the thermoplastic resin composition of the present invention may be 17.0 or more, 18.0 or more, 19.0 or more, 20.0 or more, or 21.0 or more, and may be 30.0 or less, 29.0 or less, 28.0 or less, 27.0 or less, 26.0 or less, or 25.0 or less. For example, the Abbe number vd of the thermoplastic resin composition of the present invention may be 21.0 to 26.0, 21.5 to 25.5, or 22.0 to 25.0.
Here, the Abbe number vd is calculated from the refractive indexes at a temperature of 20° C. and wavelengths of 486.13 nm, 587.56 nm, and 656.27 nm using the following formula:
νd=(nd−1)/(nF−nC)
nd: refractive index at a wavelength of 587.56 nm,
nF: refractive index at a wavelength of 486.13 nm,
nC: refers to the refractive index at a wavelength of 656.27 nm.
本発明の熱可塑性樹脂組成物は低い配向複屈折｜Δｎ｜を有する。本発明の熱可塑性樹脂組成物の配向複屈折｜Δｎ｜の絶対値は、６．０×１０－３以下であることが好ましく、５．０×１０－３以下であることがより好ましく、４．０×１０－３以下であることがさらに好ましく、３．０×１０－３以下であることが最も好ましい。配向複屈折｜Δｎ｜が上記範囲内だと、色収差に大きな影響を与えないため、光学設計通りの性能を維持することができる。配向複屈折｜Δｎ｜は、その熱可塑性樹脂から得られる厚さ１００μｍのキャストフィルムをＴｇ＋１０℃で２倍延伸した後に、波長５８９ｎｍにおいて測定した位相差値とフィルム厚みから求める。 The thermoplastic resin composition of the present invention has a low orientation birefringence |Δn|. The absolute value of the orientation birefringence |Δn| of the thermoplastic resin composition of the present invention is preferably 6.0×10 −3 or less, more preferably 5.0×10 −3 or less, even more preferably 4.0×10 −3 or less, and most preferably 3.0×10 −3 or less. If the orientation birefringence |Δn| is within the above range, it does not have a significant effect on chromatic aberration, so that the performance as per the optical design can be maintained. The orientation birefringence |Δn| is obtained from the retardation value measured at a wavelength of 589 nm and the film thickness after stretching a cast film having a thickness of 100 μm obtained from the thermoplastic resin twice at Tg+10 ° C.
本発明における熱可塑性樹脂組成物の粘度平均分子量Ｍｖは、実施例に記載した方法によって測定した場合に、５，０００以上、６，０００以上、又は７，０００以上であってもよく、２５，０００以下、２０，０００以下、又は１５，０００以下であってもよい。例えば、本発明の熱可塑性樹脂組成物の粘度平均分子量Ｍｖは、６，０００～２０，０００であってもよく、７，０００～１５，０００であってもよい。 The viscosity average molecular weight Mv of the thermoplastic resin composition of the present invention, when measured by the method described in the Examples, may be 5,000 or more, 6,000 or more, or 7,000 or more, and may be 25,000 or less, 20,000 or less, or 15,000 or less. For example, the viscosity average molecular weight Mv of the thermoplastic resin composition of the present invention may be 6,000 to 20,000, or 7,000 to 15,000.
初期色相ＹＩは、熱可塑性樹脂組成物を射出成形し、得られた成形物のＹＩを測定することで評価することができる。本発明の熱可塑性樹脂組成物の２ｍｍ厚成形物の初期色相ＹＩは、７．０以下であることが好ましく、６．０以下であることがより好ましく、５．５以下であることがさらに好ましく、５．０以下であることが特に好ましく、４．５以下であることが最も好ましい。初期色相ＹＩが上記範囲内であると各種透明部材としての使用範囲が限定されず好ましい。 The initial hue YI can be evaluated by injection molding the thermoplastic resin composition and measuring the YI of the resulting molded product. The initial hue YI of a 2 mm thick molded product of the thermoplastic resin composition of the present invention is preferably 7.0 or less, more preferably 6.0 or less, even more preferably 5.5 or less, particularly preferably 5.0 or less, and most preferably 4.5 or less. If the initial hue YI is within the above range, the range of use as various transparent components is not limited, which is preferable.
（２）光学部材
本発明の光学部材は、上記の熱可塑性樹脂組成物を含む。そのような光学部材としては、上記の熱可塑性樹脂組成物が有用となる光学用途であれば、特に限定されないが、光ディスク、透明導電性基板、光カード、シート、フィルム、光ファイバー、レンズ、プリズム、光学膜、基盤、光学フィルター、ハードコート膜等を挙げることができる。
(2) Optical Member The optical member of the present invention contains the above-mentioned thermoplastic resin composition. Such optical members are not particularly limited as long as they are used for optical applications in which the above-mentioned thermoplastic resin composition is useful, and examples of such optical members include optical disks, transparent conductive substrates, optical cards, sheets, films, optical fibers, lenses, prisms, optical films, substrates, optical filters, and hard coat films.
また、本発明の光学部材には、上記の熱可塑性樹脂組成物を含む樹脂組成物から構成されていてもよく、その樹脂組成物には、必要に応じて熱安定剤、酸化防止剤、可塑剤、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、紫外線吸収剤、離型剤等の添加剤を配合することができる。 The optical member of the present invention may be composed of a resin composition containing the above-mentioned thermoplastic resin composition, and the resin composition may contain additives such as heat stabilizers, antioxidants, plasticizers, light stabilizers, polymerized metal deactivators, flame retardants, lubricants, antistatic agents, surfactants, antibacterial agents, ultraviolet absorbers, and mold release agents, as necessary.
（３）光学レンズ
本発明の光学部材として、特に光学レンズを挙げることができる。このような光学レンズとしては、携帯電話、スマートフォン、タブレット端末、パソコン、デジタルカメラ、ビデオカメラ、車載カメラ、監視カメラ等のための撮像レンズや、ＴＯＦカメラ等のセンシングカメラ、さらにＡＲ／ＶＲ機器のためのレンズを挙げることができる。
(3) Optical Lens The optical member of the present invention may be, in particular, an optical lens. Examples of such an optical lens include imaging lenses for mobile phones, smartphones, tablet terminals, personal computers, digital cameras, video cameras, vehicle-mounted cameras, and surveillance cameras, as well as lenses for sensing cameras such as TOF cameras, and lenses for AR/VR devices.
本発明の光学レンズを射出成型で製造する場合、シリンダー温度２３０～３５０℃、金型温度７０～１８０℃の条件にて成形することが好ましい。さらに好ましくは、シリンダー温度２５０～３００℃、金型温度８０～１７０℃の条件にて成形することが好ましい。シリンダー温度が３５０℃より高い場合では、熱可塑性樹脂組成物が分解着色し、２３０℃より低い場合では、溶融粘度が高く成形が困難になりやすい。また金型温度が１８０℃より高い場合では、熱可塑性樹脂組成物から成る成形片が金型から取り出すことが困難になりやすい。他方、金型温度が、７０℃未満では、成型時の金型内で樹脂が早く固まり過ぎて成形片の形状が制御しにくくなったり、金型に付された賦型を十分に転写することが困難になりやすい。 When the optical lens of the present invention is manufactured by injection molding, it is preferable to mold the lens under the conditions of a cylinder temperature of 230 to 350°C and a mold temperature of 70 to 180°C. More preferably, it is preferable to mold the lens under the conditions of a cylinder temperature of 250 to 300°C and a mold temperature of 80 to 170°C. If the cylinder temperature is higher than 350°C, the thermoplastic resin composition decomposes and discolors, and if it is lower than 230°C, the melt viscosity is high and molding is likely to be difficult. If the mold temperature is higher than 180°C, it is likely to be difficult to remove the molded piece made of the thermoplastic resin composition from the mold. On the other hand, if the mold temperature is lower than 70°C, the resin hardens too quickly in the mold during molding, making it difficult to control the shape of the molded piece, and it is likely to be difficult to fully transfer the shape applied to the mold.
本発明の光学レンズは、必要に応じて非球面レンズの形を用いることが好適に実施される。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で球面収差を取り除く必要が無く、軽量化及び成形コストの低減化が可能になる。したがって、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。 The optical lens of the present invention is preferably implemented in the form of an aspherical lens as necessary. Aspherical lenses can reduce spherical aberration to essentially zero with a single lens, making it unnecessary to remove spherical aberration by combining multiple spherical lenses, and making it possible to reduce weight and molding costs. Aspherical lenses are therefore particularly useful as camera lenses among optical lenses.
また、本発明の熱可塑性樹脂組成物は、成形流動性が高いため、薄肉小型で複雑な形状である光学レンズの材料として特に有用である。具体的なレンズサイズとして、中心部の厚みが０．０５～１０．０ｍｍ、より好ましくは０．０５～８．０ｍｍ、さらに好ましくは０．１～６．０ｍｍである。また、直径が１．０ｍｍ～１００．０ｍｍ、より好ましくは１．０～８０．０ｍｍ、さらに好ましくは、１．０～６０．０ｍｍである。また、その形状として片面が凸、片面が凹であるメニスカスレンズであることが好ましい。 The thermoplastic resin composition of the present invention has high molding fluidity and is therefore particularly useful as a material for optical lenses that are thin, small, and have complex shapes. Specific lens sizes include a central thickness of 0.05 to 10.0 mm, more preferably 0.05 to 8.0 mm, and even more preferably 0.1 to 6.0 mm. Also, the diameter is 1.0 mm to 100.0 mm, more preferably 1.0 to 80.0 mm, and even more preferably 1.0 to 60.0 mm. The lens shape is preferably a meniscus lens with one convex side and the other concave side.
本発明の熱可塑性樹脂からなるレンズは、金型成形、切削、研磨、レーザー加工、放電加工、エッチングなど任意の方法により成形される。この中でも、製造コストの面から金型成形がより好ましい。 Lenses made of the thermoplastic resin of the present invention can be molded by any method, such as mold molding, cutting, polishing, laser processing, electric discharge processing, and etching. Among these, mold molding is more preferable in terms of manufacturing costs.
本発明を以下の実施例でさらに具体的に説明をするが、本発明はこれによって限定されるものではない。
《評価方法》
〈屈折率ｎｄ〉
各熱可塑性樹脂組成物の３ｍｍ厚板を作製し、切削、研磨した後、（株）島津製作所製のカルニュー精密屈折計ＫＰＲ－２０００を使用して、屈折率ｎｄ（５８７．５６ｎｍ）を測定した。
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.
"Evaluation method"
<Refractive index nd>
A 3 mm thick plate was prepared from each thermoplastic resin composition, cut and polished, and then the refractive index nd (587.56 nm) was measured using a Kalnew precision refractometer KPR-2000 manufactured by Shimadzu Corporation.
〈アッベ数νｄ〉
アッベ数の測定波長は、４８６．１３ｎｍ、５８７．５６ｎｍ、６５６．２７ｎｍの屈折率から下記の式を用いて算出した。
νｄ＝（ｎｄ－１）／（ｎＦ－ｎＣ）
ｎｄ：波長５８７．５６ｎｍでの屈折率、
ｎＦ：波長４８６．１３ｎｍでの屈折率、
ｎＣ：波長６５６．２７ｎｍでの屈折率を意味する。
<Abbe number νd>
The Abbe number was calculated from the refractive indexes at 486.13 nm, 587.56 nm, and 656.27 nm using the following formula.
νd=(nd−1)/(nF−nC)
nd: refractive index at a wavelength of 587.56 nm,
nF: refractive index at a wavelength of 486.13 nm,
nC: refers to the refractive index at a wavelength of 656.27 nm.
〈初期色相ＹＩ〉
各熱可塑性樹脂組成物の２ｍｍ厚板を作製し、日本電色工業（株）製 色彩・濁度同時測定器ＣＯＨ ４００（Ｄ６５光源、１０°視野）により、ＹＩを測定した。
<Initial hue YI>
A 2 mm thick plate was prepared from each thermoplastic resin composition, and the YI was measured using a color/turbidity simultaneous measuring instrument COH 400 (D65 light source, 10° field of view) manufactured by Nippon Denshoku Industries Co., Ltd.
〈乾熱黄変ΔＹＩ〉
各熱可塑性樹脂組成物の２ｍｍ厚板を作製し、乾燥雰囲気下１２０℃に５００時間暴露する乾熱試験を行い、試験前後でのＹＩを日本電色工業（株）製 色彩・濁度同時測定器ＣＯＨ ４００（Ｄ６５光源、１０°視野）で測定した後、以下の式を用いて乾熱黄変ΔＹＩを算出した。
乾熱黄変ΔＹＩ＝乾熱試験後ＹＩ―乾熱試験前ＹＩ
<Dry heat yellowing ΔYI>
A 2 mm thick plate of each thermoplastic resin composition was prepared and subjected to a dry heat test in which it was exposed to 120°C in a dry atmosphere for 500 hours. The YI before and after the test was measured using a color and turbidity simultaneous measuring instrument COH 400 (D65 light source, 10° field of view) manufactured by Nippon Denshoku Industries Co., Ltd., and then the dry heat yellowing ΔYI was calculated using the following formula.
Dry heat yellowing ΔYI = YI after dry heat test - YI before dry heat test
〈粘度平均分子量Ｍｖ〉
熱可塑性樹脂組成物の粘度平均分子量を、以下の方法で測定した。熱可塑性樹脂組成物０．７ｇを塩化メチレン１００ｍｌに溶解した溶液から、その溶液の２０℃における比粘度（ηｓｐ）を測定した。そして、下記式により算出されるＭｖを粘度平均分子量とした。
ηｓｐ／ｃ＝［η］＋０．４５×［η］２ｃ
［η］＝１．２３×１０－４Ｍｖ０．８３
ηｓｐ：比粘度
η：極限粘度
ｃ：定数（＝０．７）
Ｍｖ：粘度平均分子量
Viscosity average molecular weight Mv
The viscosity average molecular weight of the thermoplastic resin composition was measured by the following method. 0.7 g of the thermoplastic resin composition was dissolved in 100 ml of methylene chloride to measure the specific viscosity (ηsp) of the solution at 20° C. Then, Mv calculated by the following formula was taken as the viscosity average molecular weight.
ηsp/c=[η]+0.45×[η] 2c
[η] = 1.23 × 10 −4 Mv 0.83
ηsp: specific viscosity η: intrinsic viscosity c: constant (=0.7)
Mv: Viscosity average molecular weight
〈配向複屈折の絶対値｜Δｎ｜〉
熱可塑性樹脂組成物を塩化メチレンに溶解した後、ガラスシャーレ上にキャストし、十分乾燥することで厚さ１００μｍのキャストフィルムを作製した。該フィルムをＴｇ＋１０℃で２倍延伸し、日本分光（株）製エリプソメーターＭ－２２０を用いて５８９ｎｍにおける位相差（Ｒｅ）を測定し、下記式より配向複屈折の絶対値（｜Δｎ｜）を求めた。
｜Δｎ｜＝｜Ｒｅ／ｄ｜
Δｎ：配向複屈折
Ｒｅ：位相差（ｎｍ）
ｄ：厚さ（ｎｍ）
<Absolute value of orientation birefringence |Δn|>
The thermoplastic resin composition was dissolved in methylene chloride, cast on a glass petri dish, and thoroughly dried to prepare a cast film having a thickness of 100 μm. The film was stretched twice at Tg+10° C., and the retardation (Re) at 589 nm was measured using an Ellipsometer M-220 manufactured by JASCO Corporation. The absolute value of the orientation birefringence (|Δn|) was calculated from the following formula.
|Δn|=|Re/d|
Δn: Orientation birefringence
Re: phase difference (nm)
d: thickness (nm)
〈合成例１〉（ポリエステルカーボネート樹脂（ＰＥＣ１）の製造）
９，９－ビス（４－（２－ヒドロキシエトキシ）フェニル）フルオレン（以下、ＢＰＥＦと省略することがある）８２．０ｍｏｌ、テレフタル酸ジメチル（以下、ＤＭＴと省略することがある）１８．０ｍｏｌ、ジフェニルカーボネート（以下、ＤＰＣと省略することがある）７１．０ｍｏｌ、アルミニウムアセチルアセトネート（以下、Ｃａｔ．Ａｌと省略することがある）１．５×１０－２ｍｏｌ及び３，５－ジ－ｔｅｒｔ－ブチル－４－ヒドロキシベンジルホスホン酸ジエチル（以下、Ｃａｔ．Ｐと省略することがある）３．０×１０－２ｍｏｌを攪拌機および留出装置付きの反応釜に入れ、窒素置換を３度行った後、ジャケットを２００℃に加熱し、原料を溶融させた。
Synthesis Example 1 (Production of Polyester Carbonate Resin (PEC1))
82.0 mol of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (hereinafter sometimes abbreviated as BPEF), 18.0 mol of dimethyl terephthalate (hereinafter sometimes abbreviated as DMT), 71.0 mol of diphenyl carbonate (hereinafter sometimes abbreviated as DPC), 1.5×10 −2 mol of aluminum acetylacetonate (hereinafter sometimes abbreviated as Cat.Al), and 3.0×10 −2 mol of diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate (hereinafter sometimes abbreviated as Cat.P) were placed in a reaction kettle equipped with a stirrer and a distillation device, and the inside of the reaction kettle was purged with nitrogen three times, after which the jacket was heated to 200° C. to melt the raw materials.
完全溶解後、２０分かけて４０ｋＰａまで減圧した。その後、２６０℃まで昇温、０．１３ｋＰａ以下まで減圧し、所定の撹拌トルクに到達するまで重合反応を行った。反応終了後、生成した樹脂をペレタイズしながら抜き出し、ポリエステルカーボネート樹脂（ＰＥＣ１）のペレットを得た。得られたポリエステルカーボネート樹脂（ＰＥＣ１）のＭｖは１０，１００であった。 After complete dissolution, the pressure was reduced to 40 kPa over 20 minutes. The temperature was then raised to 260°C, the pressure was reduced to 0.13 kPa or less, and the polymerization reaction was carried out until the specified stirring torque was reached. After the reaction was completed, the resulting resin was pelletized and extracted to obtain pellets of polyester carbonate resin (PEC1). The Mv of the resulting polyester carbonate resin (PEC1) was 10,100.
〈合成例２〉（ポリエステルカーボネート樹脂（ＰＥＣ２）の製造）
特許文献１の実施例４を参考に、ＢＰＥＦ９０．０ｍｏｌ、ＤＭＴ１０．０ｍｏｌ、ＤＰＣ８４．０ｍｏｌ及びチタンテトラブトキシド（以下、Ｃａｔ．Ｔｉと省略することがある）１．０×１０－２ｍｏｌを攪拌機および留出装置付きの反応釜に入れ、窒素置換を３度行った後、ジャケットを１８０℃に加熱し、原料を溶融させた。
Synthesis Example 2 (Production of polyester carbonate resin (PEC2))
Referring to Example 4 of Patent Document 1, 90.0 mol of BPEF, 10.0 mol of DMT, 84.0 mol of DPC, and 1.0 × 10 -2 mol of titanium tetrabutoxide (hereinafter, sometimes abbreviated as Cat.Ti) were placed in a reaction kettle equipped with a stirrer and a distillation device, and after nitrogen replacement was performed three times, the jacket was heated to 180°C to melt the raw materials.
完全溶解後、２０分かけて３０ｋＰａまで減圧した。その後、２５０℃まで昇温、０．１３ｋＰａ以下まで減圧し、所定の撹拌トルクに到達するまで重合反応を行った。反応終了後、生成した樹脂をペレタイズしながら抜き出し、ポリエステルカーボネート樹脂（ＰＥＣ２）のペレットを得た。得られたポリエステルカーボネート樹脂（ＰＥＣ２）のＭｖは１０，８００であった。 After complete dissolution, the pressure was reduced to 30 kPa over 20 minutes. The temperature was then raised to 250°C, the pressure was reduced to 0.13 kPa or less, and the polymerization reaction was carried out until the specified stirring torque was reached. After the reaction was completed, the resulting resin was pelletized and extracted to obtain pellets of polyester carbonate resin (PEC2). The Mv of the resulting polyester carbonate resin (PEC2) was 10,800.
〈合成例３〉（ポリカーボネート樹脂（ＰＣ１）の製造）
ＢＰＥＦ１００．０ｍｏｌ、ＤＰＣ１０４．０ｍｏｌ及び炭酸水素ナトリウム（以下、Ｃａｔ．Ｎａと省略することがある）６．０×１０－４ｍｏｌ（炭酸水素ナトリウムは０．１ｗｔ％水溶液の状態で添加した）を攪拌機および留出装置付きの反応釜に入れ、窒素置換を３度行った後、ジャケットを２００℃に加熱し、原料を溶融させた。
Synthesis Example 3 (Production of Polycarbonate Resin (PC1))
100.0 mol of BPEF, 104.0 mol of DPC, and 6.0 × 10 -4 mol of sodium hydrogen carbonate (hereinafter sometimes abbreviated as Cat.Na) (sodium hydrogen carbonate was added in the form of a 0.1 wt % aqueous solution) were placed in a reaction kettle equipped with a stirrer and a distillation device, and after nitrogen replacement was performed three times, the jacket was heated to 200°C to melt the raw materials.
完全溶解後、２０分かけて４０ｋＰａまで減圧した。その後、２４０℃まで昇温、０．１３ｋＰａ以下まで減圧し、所定の撹拌トルクに到達するまで重合反応を行った。反応終了後、生成した樹脂をペレタイズしながら抜き出し、ポリカーボネート樹脂（ＰＣ１）のペレットを得た。得られたポリカーボネート樹脂（ＰＣ１）のＭｖは９，８００であった。 After complete dissolution, the pressure was reduced to 40 kPa over 20 minutes. The temperature was then raised to 240°C, the pressure was reduced to 0.13 kPa or less, and the polymerization reaction was carried out until the specified stirring torque was reached. After the reaction was completed, the resulting resin was pelletized and extracted to obtain pellets of polycarbonate resin (PC1). The Mv of the resulting polycarbonate resin (PC1) was 9,800.
〈実施例１〉
合成例１で得られたポリエステルカーボネート樹脂（ＰＥＣ１）と離型剤としてステアリン酸モノグリセリド［製品名：理研ビタミン株式会社製のリケマールＳ－１００Ａ］を表１に示す質量比で配合し、よく混合した後、押出機（日本製鋼所製 ＴＥＸ３０α ３０ｍｍφ二軸押出機）により２７０℃、ベント圧力３０ｍｍＨｇで溶融混練した。溶融混錬によって得られた熱可塑性樹脂組成物をストランド状に押出した後、ペレタイザーを用いてペレット化して、熱可塑性樹脂組成物のペレットを得た。該ペレットのＭｖは９，８００であった。該ペレットを２８０℃で射出成型して２ｍｍ厚及び３ｍｍ厚の板状成型片を得た。成型体は透明であった。評価結果を表１に示す。
Example 1
The polyester carbonate resin (PEC1) obtained in Synthesis Example 1 and stearic acid monoglyceride as a mold release agent [product name: Rikemal S-100A manufactured by Riken Vitamin Co., Ltd.] were blended in the mass ratio shown in Table 1, mixed well, and then melt-kneaded at 270 ° C. and vent pressure of 30 mmHg using an extruder (TEX30α 30 mmφ twin-screw extruder manufactured by Japan Steel Works, Ltd.). The thermoplastic resin composition obtained by melt-kneading was extruded into a strand shape and then pelletized using a pelletizer to obtain pellets of the thermoplastic resin composition. The Mv of the pellets was 9,800. The pellets were injection molded at 280 ° C. to obtain plate-shaped molded pieces with a thickness of 2 mm and 3 mm. The molded bodies were transparent. The evaluation results are shown in Table 1.
〈実施例２〉
合成例１で得られたポリエステルカーボネート樹脂（ＰＥＣ１）と離型剤リケマールＳ－１００Ａを表１に示す質量比で配合し、よく混合した後、押出機（日本製鋼所製 ＴＥＸ３０α ３０ｍｍφ二軸押出機）により２７０℃、ベント圧力３０ｍｍＨｇで溶融混練した。溶融混錬によって得られた熱可塑性樹脂組成物をストランド状に押出した後、ペレタイザーを用いてペレット化して、熱可塑性樹脂組成物のペレットを得た。該ペレットのＭｖは９，８００であった。該ペレットを２８０℃で射出成型して２ｍｍ厚及び３ｍｍ厚の板状成型片を得た。成型体は透明であった。評価結果を表１に示す。
Example 2
The polyester carbonate resin (PEC1) obtained in Synthesis Example 1 and the release agent Rikemal S-100A were blended in the mass ratio shown in Table 1, mixed thoroughly, and then melt-kneaded at 270°C and a vent pressure of 30 mmHg using an extruder (TEX30α 30 mmφ twin-screw extruder manufactured by Japan Steel Works, Ltd.). The thermoplastic resin composition obtained by melt-kneading was extruded into a strand shape and then pelletized using a pelletizer to obtain pellets of the thermoplastic resin composition. The Mv of the pellets was 9,800. The pellets were injection molded at 280°C to obtain plate-shaped molded pieces having a thickness of 2 mm and 3 mm. The molded bodies were transparent. The evaluation results are shown in Table 1.
〈実施例３〉
合成例１で得られたポリエステルカーボネート樹脂（ＰＥＣ１）と離型剤リケマールＳ－１００Ａを表１に示す質量比で配合し、よく混合した後、押出機（日本製鋼所製 ＴＥＸ３０α ３０ｍｍφ二軸押出機）により２７０℃、ベント圧力３０ｍｍＨｇで溶融混練した。溶融混錬によって得られた熱可塑性樹脂組成物をストランド状に押出した後、ペレタイザーを用いてペレット化して、熱可塑性樹脂組成物のペレットを得た。該ペレットのＭｖは９，９００であった。該ペレットを２８０℃で射出成型して２ｍｍ厚及び３ｍｍ厚の板状成型片を得た。成型体は透明であった。評価結果を表１に示す。
Example 3
The polyester carbonate resin (PEC1) obtained in Synthesis Example 1 and the release agent Rikemal S-100A were blended in the mass ratio shown in Table 1, mixed thoroughly, and then melt-kneaded at 270°C and a vent pressure of 30 mmHg using an extruder (TEX30α 30 mmφ twin-screw extruder manufactured by Japan Steel Works, Ltd.). The thermoplastic resin composition obtained by melt-kneading was extruded into a strand shape and then pelletized using a pelletizer to obtain pellets of the thermoplastic resin composition. The Mv of the pellets was 9,900. The pellets were injection molded at 280°C to obtain plate-shaped molded pieces having a thickness of 2 mm and 3 mm. The molded bodies were transparent. The evaluation results are shown in Table 1.
〈実施例４〉
合成例１で得られたポリエステルカーボネート樹脂（ＰＥＣ１）と離型剤リケマールＳ－１００Ａを表１に示す質量比で配合し、よく混合した後、押出機（日本製鋼所製 ＴＥＸ３０α ３０ｍｍφ二軸押出機）により２７０℃、ベント圧力３０ｍｍＨｇで溶融混練した。溶融混錬によって得られた熱可塑性樹脂組成物をストランド状に押出した後、ペレタイザーを用いてペレット化して、熱可塑性樹脂組成物のペレットを得た。該ペレットのＭｖは９，８００であった。該ペレットを２８０℃で射出成型して２ｍｍ厚及び３ｍｍ厚の板状成型片を得た。成型体は透明であった。評価結果を表１に示す。
Example 4
The polyester carbonate resin (PEC1) obtained in Synthesis Example 1 and the release agent Rikemal S-100A were blended in the mass ratio shown in Table 1, mixed thoroughly, and then melt-kneaded at 270°C and a vent pressure of 30 mmHg using an extruder (TEX30α 30 mmφ twin-screw extruder manufactured by Japan Steel Works, Ltd.). The thermoplastic resin composition obtained by melt-kneading was extruded into a strand shape and then pelletized using a pelletizer to obtain pellets of the thermoplastic resin composition. The Mv of the pellets was 9,800. The pellets were injection molded at 280°C to obtain plate-shaped molded pieces having a thickness of 2 mm and 3 mm. The molded bodies were transparent. The evaluation results are shown in Table 1.
〈実施例５〉
合成例３で得られたポリカーボネート樹脂（ＰＣ１）と離型剤リケマールＳ－１００Ａを表１に示す質量比で配合し、よく混合した後、押出機（日本製鋼所製 ＴＥＸ３０α ３０ｍｍφ二軸押出機）により２７０℃、ベント圧力３０ｍｍＨｇで溶融混練した。溶融混錬によって得られた熱可塑性樹脂組成物をストランド状に押出した後、ペレタイザーを用いてペレット化して、熱可塑性樹脂組成物のペレットを得た。該ペレットのＭｖは９，６００であった。該ペレットを２８０℃で射出成型して２ｍｍ厚及び３ｍｍ厚の板状成型片を得た。成型体は透明であった。評価結果を表１に示す。
Example 5
The polycarbonate resin (PC1) obtained in Synthesis Example 3 and the release agent Rikemal S-100A were blended in the mass ratio shown in Table 1, mixed thoroughly, and then melt-kneaded at 270°C and a vent pressure of 30 mmHg using an extruder (TEX30α 30 mmφ twin-screw extruder manufactured by Japan Steel Works, Ltd.). The thermoplastic resin composition obtained by melt-kneading was extruded into a strand shape and then pelletized using a pelletizer to obtain pellets of the thermoplastic resin composition. The Mv of the pellets was 9,600. The pellets were injection molded at 280°C to obtain plate-shaped molded pieces having a thickness of 2 mm and 3 mm. The molded bodies were transparent. The evaluation results are shown in Table 1.
〈実施例６〉
合成例１で得られたポリエステルカーボネート樹脂（ＰＥＣ１）と離型剤リケマールＳ－１００Ａ及び酸化防止剤として環状ネオペンタンテトライルビス（２，６－ジ－ｔｅｒｔ－ブチル－４－メチルフェニルホスファイト）［製品名：株式会社ＡＤＥＫＡ製のアデカスタブＰＥＰ－３６］を表１に示す質量比で配合し、よく混合した後、押出機（日本製鋼所製 ＴＥＸ３０α ３０ｍｍφ二軸押出機）により２７０℃、ベント圧力３０ｍｍＨｇで溶融混練した。溶融混錬によって得られた熱可塑性樹脂組成物をストランド状に押出した後、ペレタイザーを用いてペレット化して、熱可塑性樹脂組成物のペレットを得た。該ペレットのＭｖは９，９００であった。該ペレットを２８０℃で射出成型して２ｍｍ厚及び３ｍｍ厚の板状成型片を得た。成型体は透明であった。評価結果を表１に示す。
Example 6
The polyester carbonate resin (PEC1) obtained in Synthesis Example 1 was blended with the release agent Rikemal S-100A and cyclic neopentanetetraylbis(2,6-di-tert-butyl-4-methylphenylphosphite) [product name: Adeka STAB PEP-36 manufactured by ADEKA CORPORATION] as an antioxidant in the mass ratios shown in Table 1, mixed well, and then melt-kneaded at 270 ° C. and vent pressure of 30 mmHg using an extruder (TEX30α 30 mmφ twin-screw extruder manufactured by Japan Steel Works, Ltd.). The thermoplastic resin composition obtained by melt-kneading was extruded into a strand shape and then pelletized using a pelletizer to obtain pellets of the thermoplastic resin composition. The Mv of the pellets was 9,900. The pellets were injection molded at 280 ° C. to obtain plate-shaped molded pieces having a thickness of 2 mm and 3 mm. The molded bodies were transparent. The evaluation results are shown in Table 1.
〈比較例１〉
合成例１で得られたポリエステルカーボネート樹脂（ＰＥＣ１）と離型剤リケマールＳ－１００Ａ及び酸化防止剤ＰＥＰ－３６を表１に示す質量比で配合し、よく混合した後、押出機（日本製鋼所製 ＴＥＸ３０α ３０ｍｍφ二軸押出機）により２７０℃、ベント圧力３０ｍｍＨｇで溶融混練した。溶融混錬によって得られた熱可塑性樹脂組成物をストランド状に押出した後、ペレタイザーを用いてペレット化して、熱可塑性樹脂組成物のペレットを得た。該ペレットのＭｖは９，９００であった。該ペレットを２８０℃で射出成型して２ｍｍ厚及び３ｍｍ厚の板状成型片を得た。成型体は透明であった。評価結果を表１に示す。
Comparative Example 1
The polyester carbonate resin (PEC1) obtained in Synthesis Example 1 was blended with the release agent Rikemal S-100A and the antioxidant PEP-36 in the mass ratio shown in Table 1, mixed thoroughly, and then melt-kneaded at 270 ° C. and vent pressure of 30 mmHg using an extruder (TEX30α 30 mmφ twin-screw extruder manufactured by Japan Steel Works, Ltd.). The thermoplastic resin composition obtained by melt-kneading was extruded into a strand shape and then pelletized using a pelletizer to obtain pellets of the thermoplastic resin composition. The Mv of the pellets was 9,900. The pellets were injection molded at 280 ° C. to obtain plate-shaped molded pieces having a thickness of 2 mm and 3 mm. The molded bodies were transparent. The evaluation results are shown in Table 1.
〈比較例２〉
合成例３で得られたポリカーボネート樹脂（ＰＣ１）と離型剤リケマールＳ－１００Ａ及び酸化防止剤ＰＥＰ－３６を表１に示す質量比で配合し、よく混合した後、押出機（日本製鋼所製 ＴＥＸ３０α ３０ｍｍφ二軸押出機）により２７０℃、ベント圧力３０ｍｍＨｇで溶融混練した。溶融混錬によって得られた熱可塑性樹脂組成物をストランド状に押出した後、ペレタイザーを用いてペレット化して、熱可塑性樹脂組成物のペレットを得た。該ペレットのＭｖは９，７００であった。該ペレットを２８０℃で射出成型して２ｍｍ厚及び３ｍｍ厚の板状成型片を得た。成型体は透明であった。評価結果を表１に示す。
Comparative Example 2
The polycarbonate resin (PC1) obtained in Synthesis Example 3, the release agent Rikemal S-100A, and the antioxidant PEP-36 were blended in the mass ratios shown in Table 1, mixed thoroughly, and then melt-kneaded at 270 ° C. and vent pressure of 30 mmHg using an extruder (TEX30α 30 mmφ twin-screw extruder manufactured by Japan Steel Works, Ltd.). The thermoplastic resin composition obtained by melt-kneading was extruded into a strand shape, and then pelletized using a pelletizer to obtain pellets of the thermoplastic resin composition. The Mv of the pellets was 9,700. The pellets were injection molded at 280 ° C. to obtain plate-shaped molded pieces having a thickness of 2 mm and 3 mm. The molded bodies were transparent. The evaluation results are shown in Table 1.
〈比較例３〉
特許文献１の実施例４を参考に、合成例２で得られたポリエステルカーボネート樹脂（ＰＥＣ２）と離型剤としてペンタエリスリトールテトラステアレート及び酸化防止剤としてビス（２，４－ジクミルフェニル）ペンタエリスリトールジホスファイトを表１に示す質量比で配合し、よく混合した後、押出機（日本製鋼所製 ＴＥＸ３０α ３０ｍｍφ二軸押出機）により２７０℃、ベント圧力３０ｍｍＨｇで溶融混練した。溶融混錬によって得られた熱可塑性樹脂組成物をストランド状に押出した後、ペレタイザーを用いてペレット化して、熱可塑性樹脂組成物のペレットを得た。該ペレットのＭｖは１０，６００であった。該ペレットを２８０℃で射出成型して２ｍｍ厚及び３ｍｍ厚の板状成型片を得た。成型体は透明であった。評価結果を表１に示す。
Comparative Example 3
Referring to Example 4 of Patent Document 1, the polyester carbonate resin (PEC2) obtained in Synthesis Example 2 was blended with pentaerythritol tetrastearate as a release agent and bis(2,4-dicumylphenyl)pentaerythritol diphosphite as an antioxidant in the mass ratio shown in Table 1, mixed thoroughly, and then melt-kneaded at 270°C and vent pressure of 30 mmHg using an extruder (TEX30α 30 mmφ twin-screw extruder manufactured by Japan Steel Works, Ltd.). The thermoplastic resin composition obtained by melt-kneading was extruded into a strand shape and pelletized using a pelletizer to obtain pellets of the thermoplastic resin composition. The Mv of the pellets was 10,600. The pellets were injection molded at 280°C to obtain plate-shaped molded pieces with a thickness of 2 mm and 3 mm. The molded bodies were transparent. The evaluation results are shown in Table 1.
表１に示す結果より、実施例１～６の熱可塑性樹脂組成物は高屈折率、低複屈折で光学特性に優れることに加え、比較例１～３の熱可塑性樹脂組成物に比べ、長期耐熱性に優れることが分かった。本発明の熱可塑性樹脂組成物は優れた光学特性であるため光学材料、中でも光学レンズの用途として極めて有用であり、さらに長期耐熱性に優れることから広範な環境下に応用展開できる。 From the results shown in Table 1, it was found that the thermoplastic resin compositions of Examples 1 to 6 have excellent optical properties with a high refractive index and low birefringence, and also have excellent long-term heat resistance compared to the thermoplastic resin compositions of Comparative Examples 1 to 3. The thermoplastic resin composition of the present invention has excellent optical properties and is therefore extremely useful as an optical material, particularly for optical lenses, and furthermore, because of its excellent long-term heat resistance, it can be applied in a wide range of environments.
本発明の熱可塑性樹脂組成物は、高屈折率、低複屈折および長期耐熱性を有するため、レンズやフィルムなどの光学材料に好適に使用される。
The thermoplastic resin composition of the present invention has a high refractive index, low birefringence and long-term heat resistance, and is therefore suitable for use in optical materials such as lenses and films.
Claims (9)
The optical member according to claim 8 , which is an optical lens.
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