CN115926135A - Thermoplastic resin composition for optical forming body and manufacturing method thereof - Google Patents
Thermoplastic resin composition for optical forming body and manufacturing method thereof Download PDFInfo
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- CN115926135A CN115926135A CN202211459624.0A CN202211459624A CN115926135A CN 115926135 A CN115926135 A CN 115926135A CN 202211459624 A CN202211459624 A CN 202211459624A CN 115926135 A CN115926135 A CN 115926135A
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- 239000011342 resin composition Substances 0.000 title claims abstract description 34
- 229920005992 thermoplastic resin Polymers 0.000 title claims abstract description 34
- 230000003287 optical effect Effects 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 239000012788 optical film Substances 0.000 claims description 2
- 125000003375 sulfoxide group Chemical group 0.000 claims description 2
- 239000004973 liquid crystal related substance Substances 0.000 claims 1
- 238000000465 moulding Methods 0.000 abstract description 4
- 238000005452 bending Methods 0.000 abstract description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 16
- 238000004821 distillation Methods 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- -1 dicarboxylic acid ester Chemical class 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 150000004650 carbonic acid diesters Chemical class 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 229910052746 lanthanum Inorganic materials 0.000 description 4
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 4
- 229920005668 polycarbonate resin Polymers 0.000 description 4
- 239000004431 polycarbonate resin Substances 0.000 description 4
- 239000004246 zinc acetate Substances 0.000 description 4
- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 3
- DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 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 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- PYPNFSVOZBISQN-LNTINUHCSA-K cerium acetylacetonate Chemical compound [Ce+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O PYPNFSVOZBISQN-LNTINUHCSA-K 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 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 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- DEBLRFTYCRWXLV-UHFFFAOYSA-N (2,3-diethylphenyl) hydrogen carbonate Chemical compound CCC1=CC=CC(OC(O)=O)=C1CC DEBLRFTYCRWXLV-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
- OZGFLBCWIQDWLO-UHFFFAOYSA-N 2-[1-[2-(carboxymethoxy)naphthalen-1-yl]naphthalen-2-yl]oxyacetic acid Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3OCC(=O)O)=C(OCC(O)=O)C=CC2=C1 OZGFLBCWIQDWLO-UHFFFAOYSA-N 0.000 description 1
- DZTMOJWISKAOML-UHFFFAOYSA-N 2-hydroxyethyl phenylmethanesulfonate Chemical compound OCCOS(=O)(=O)CC1=CC=CC=C1 DZTMOJWISKAOML-UHFFFAOYSA-N 0.000 description 1
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 1
- ZKSBIVRPWSVSEK-UHFFFAOYSA-N COC(=O)C1(C(=CC=CC1)C1=CC=CC=C1)C(=O)OC Chemical compound COC(=O)C1(C(=CC=CC1)C1=CC=CC=C1)C(=O)OC ZKSBIVRPWSVSEK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- VKDPSTNROWSESS-UHFFFAOYSA-N OCCOC1(C(=C2C=CC=CC2=CC1)C1=CC=CC2=CC=CC=C12)OCCO Chemical group OCCOC1(C(=C2C=CC=CC2=CC1)C1=CC=CC2=CC=CC=C12)OCCO VKDPSTNROWSESS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GPGJRMGFEBAHDT-UHFFFAOYSA-N [2,3-di(propan-2-yl)phenyl] hydrogen carbonate Chemical compound CC(C)C1=C(C(=CC=C1)OC(=O)O)C(C)C GPGJRMGFEBAHDT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- UCVMQZHZWWEPRC-UHFFFAOYSA-L barium(2+);hydrogen carbonate Chemical compound [Ba+2].OC([O-])=O.OC([O-])=O UCVMQZHZWWEPRC-UHFFFAOYSA-L 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- FLLNLJJKHKZKMB-UHFFFAOYSA-N boron;tetramethylazanium Chemical compound [B].C[N+](C)(C)C FLLNLJJKHKZKMB-UHFFFAOYSA-N 0.000 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 235000010237 calcium benzoate Nutrition 0.000 description 1
- 239000004301 calcium benzoate Substances 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- HZQXCUSDXIKLGS-UHFFFAOYSA-L calcium;dibenzoate;trihydrate Chemical compound O.O.O.[Ca+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HZQXCUSDXIKLGS-UHFFFAOYSA-L 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000003484 crystal nucleating agent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 1
- OCSXMIBZIHMVCP-UHFFFAOYSA-N dimethyl naphthalene-1,4-dicarboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC=C(C(=O)OC)C2=C1 OCSXMIBZIHMVCP-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- JGIZKLDQCIOYLH-UHFFFAOYSA-L magnesium;phenyl phosphate Chemical compound [Mg+2].[O-]P([O-])(=O)OC1=CC=CC=C1 JGIZKLDQCIOYLH-UHFFFAOYSA-L 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- IIJQXSWPACKCHL-UHFFFAOYSA-N methyl 1-(2-methoxycarbonylnaphthalen-1-yl)naphthalene-2-carboxylate Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3C(=O)OC)=C(C(=O)OC)C=CC2=C1 IIJQXSWPACKCHL-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000006082 mold release agent Substances 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- WJMMDJOFTZAHHS-UHFFFAOYSA-L strontium;carbonic acid;carbonate Chemical compound [Sr+2].OC([O-])=O.OC([O-])=O WJMMDJOFTZAHHS-UHFFFAOYSA-L 0.000 description 1
- RXSHXLOMRZJCLB-UHFFFAOYSA-L strontium;diacetate Chemical compound [Sr+2].CC([O-])=O.CC([O-])=O RXSHXLOMRZJCLB-UHFFFAOYSA-L 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
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- Polyesters Or Polycarbonates (AREA)
Abstract
The present invention relates to a thermoplastic resin composition containing a structural unit derived from a compound represented by the general formula (a), a structural unit derived from a compound represented by the general formula (B), and a structural unit derived from a compound represented by the general formula (C), and having advantages such as a high refractive index, a low molding shrinkage rate, and good bending resistance.
Description
Technical Field
The present invention relates to the field of optical resins, and more particularly to a thermoplastic resin composition for optical forming bodies and a method for producing the same.
Background
The permeability of global smart phones is very high, and the photographing function is regarded as a function which is highly concerned by users, so that the optical lens becomes a main position for upgrading the smart phones. The industry is faced with multi-dimensional upgrading such as high-definition, multi-lens, multi-camera, periscope and TOF in the future. In addition, intelligent driving is taken as a competition focus of a vehicle and an enterprise, the military supply competition of hardware is continuously upgraded, and the configuration that a new vehicle issued recently is provided with 5 cameras on average compared with the configuration that the new vehicle carries the 5 cameras on the last round of intelligent vehicle models is obviously improved. The automatic driving environment sensing needs higher definition of the camera to acquire longer detection distance and more information. Along with the development trend of light weight of camera equipment, no matter in the fields of mobile phones, vehicles and security protection, plastic lenses gradually replace glass lenses.
Optical resin is the first choice for manufacturing plastic lenses because of its advantages of high refractive index, easy molding, high production efficiency, etc. Patent US4810771 proposes a high refractive polyester resin material for optical lenses, which is prepared by using 9,9-bis- (4-hydroxyphenyl) fluorene as a monomer and has a refractive index of about 1.64. Konika patent JP2001072872 discloses a thermoplastic resin material for optical lenses and a manufacturing method thereof, mainly adopts 2, 2-bis- (2-hydroxyethoxy) -1, 1-binaphthyl as a polymerization monomer, can be used for preparing optical resin materials such as polyester, polycarbonate, polyurethane, sulfone polymer and the like, and has higher refractive index which can reach about 1.66. However, the refractive index of these resin materials cannot meet the use requirement of a higher definition camera, and it is necessary to develop a monomer having a higher molar refractive index to prepare a copolymer resin. In addition, for mobile phones and vehicle-mounted lenses, real scenes of vibration, collision and falling exist, and the plastic lenses are required to have high bending strength in a vibration falling test, so that the lenses are guaranteed not to deform.
Disclosure of Invention
The invention aims to provide a thermoplastic resin composition, a manufacturing method thereof and application thereof in the field of optical forming bodies.
To achieve the above object, the present invention provides a thermoplastic resin composition, which in one embodiment comprises a structural unit derived from a compound represented by the general formula (A), a structural unit derived from a compound represented by the general formula (B), and a structural unit derived from a compound represented by the general formula (C),
in the general formula (A), X represents an alkylene group having 1 to 4 carbon atoms, and a and b each independently represent an integer of 1 to 10; r 1 ～R 4 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms,
in the general formula (B), Y represents an alkylene group having 1 to 4 carbon atoms, and c and d each independently represents an integer of 1 to 10; r 5 ～R 8 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms; m represents a direct bond, -O-, -S-, -NH-, a sulfone or sulfoxide group an alkylene group having 1 to 6 carbon atoms, a cycloalkylene group having 5 to 20 carbon atoms,
in the general formula (C), Z represents an alkylene group having 1 to 4 carbon atoms, and e and f each independently represent an integer of 1 to 10; r is 9 ～R 12 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms,
the thermoplastic resin composition, wherein the proportion of the structural unit represented by the general formula (A) is 0.1 to 9.9 mol%,
the proportion of the structural unit represented by the general formula (B) is 6 to 90 mol%,
the proportion of the structural unit represented by the general formula (C) is 5 to 85 mol%.
Preferably, the thermoplastic resin composition,
the proportion of the structural unit represented by the general formula (A) is 3 to 9 mol%,
the proportion of the structural unit represented by the general formula (B) is 30 to 80 mol%,
the proportion of the structural unit represented by the general formula (C) is 15 to 65 mol%.
The thermoplastic resin composition of the present invention, in another embodiment, comprises a structural unit derived from a compound represented by the general formula (A) and a structural unit derived from a compound represented by the general formula (C),
wherein the proportion of the structural unit represented by the general formula (A) is 10 to 90 mol%,
the proportion of the structural unit represented by the general formula (C) is 10 to 90 mol%.
Preferably, the thermoplastic resin composition has, in addition to the above-mentioned components,
the proportion of the structural unit represented by the general formula (A) is 40 to 70 mol%,
the proportion of the structural unit represented by the general formula (C) is 30 to 60 mol%.
The form in which the structural unit derived from the compound represented by the general formula (a), the general formula (B), and the general formula (C) described in the present invention is contained in the resin is not particularly limited. For example, in the present invention, the thermoplastic resin composition may contain a copolymer containing structural units derived from the compounds represented by the general formulae (a), (B), and (C), or may be a binary resin composition containing a homopolymer composed of each structural unit; alternatively, the blend may be one obtained by blending a homopolymer containing a structural unit derived from a compound represented by the general formula (a), a structural unit derived from a compound represented by the general formula (B), and a homopolymer containing a structural unit derived from a compound represented by the general formula (C), or one obtained by blending a homopolymer containing a structural unit derived from a compound represented by the general formula (a) and a copolymer containing a structural unit derived from a compound represented by the general formula (B).
The thermoplastic resin composition of the present invention may have any structure of random, block and alternating copolymer structures.
The thermoplastic resin composition of the present invention may contain additives such as a mold release agent, an ultraviolet absorber, a fluidity improver, a crystal nucleating agent, a reinforcing agent, a dye, an antistatic agent, or an antibacterial agent.
The thermoplastic resin composition of the present invention can be prepared by reacting a dihydroxy compound represented by the general formula (A), the general formula (B) and the general formula (C) with a carbonic diester and/or a dicarboxylic acid and/or a dicarboxylic ester.
Preferably, the dihydroxy compound and the carbonic acid diester and/or the dicarboxylic acid ester are produced by a melt transesterification polycondensation method in the presence of a basic compound catalyst, a transesterification catalyst, or a mixed catalyst composed of both of them, or in the absence of a catalyst.
Preferably, the dihydroxy compound represented by formula (a) is at least one of the following structures:
preferably, the dihydroxy compound represented by formula (B) is at least one of the following structures:
preferably, the dihydroxy compound represented by formula (C) is at least one of the following structures:
in the present invention, the above-mentioned carbonic acid diester is one or more of diphenyl carbonate, ditolyl carbonate, diethylphenyl carbonate, diisopropylphenyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, etc., preferably diphenyl carbonate;
the dicarboxylic acid is any one or the combination of at least two of terephthalic acid, 1, 4-naphthalenedicarboxylic acid, 2, 6-naphthalenedicarboxylic acid, 2-biphenyldicarboxylic acid, 1, 4-cyclohexanedicarboxylic acid and 2,2 '-bis (carboxymethoxy) -1,1' -binaphthyl, preferably terephthalic acid and/or 2, 6-naphthalenedicarboxylic acid;
the dicarboxylic acid ester is any one or combination of at least two of dimethyl terephthalate, diethyl terephthalate, dimethyl terephthalate diacetate, dimethyl 1, 4-naphthalenedicarboxylate, dimethyl 2, 6-naphthalenedicarboxylate, dimethyl 2, 2-biphenyldicarboxylate, dimethyl 1, 4-cyclohexanedicarboxylate, and 2,2 '-bis (carbomethoxy) -1,1' -binaphthyl, preferably dimethyl terephthalate and/or dimethyl 2, 6-naphthalenedicarboxylate.
The molar ratio of the carbonic acid diester and/or dicarboxylic acid ester to the sum of the dihydroxy compounds of the general formulae (a), (B) and (C) added is from 0.97 to 1.1, preferably from 1.01 to 1.08.
The basic compound catalyst is one or more of lithium chloride, sodium chloride, potassium chloride, cesium chloride, lanthanum acetylacetonate, cerium acetylacetonate, sodium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, lithium bicarbonate, sodium bicarbonate, potassium bicarbonate, magnesium bicarbonate, calcium bicarbonate, strontium bicarbonate, barium bicarbonate, sodium carbonate, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium benzoate, magnesium phenylphosphate, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide, triethylamine, dimethylbenzylamine, triphenylamine, diethylamine, tetramethylammonium borohydride, tetrabutylammonium tetrabuty-tetrabenzoate, ammonium tetraphenylborate and the like, preferably one or more of sodium hydroxide, sodium bicarbonate and cesium carbonate.
The transesterification catalyst of the present invention may be one or more selected from zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin chloride, tin acetate, cerium acetylacetonate, zirconium acetate, tetrabutoxy zirconium, etc., preferably one or more selected from lanthanum acetylacetonate, zirconium acetate, and zinc acetate.
The molar ratio of the total of the basic compound catalyst and/or the transesterification catalyst of the present invention to the total of the dihydroxy compounds is 1X 10 -8 ～5×10 -4 The preferred ratio is 1X 10 -6 ～2×10 -4 。
In some preferred embodiments of the present invention, the method for preparing the thermoplastic resin composition comprises: dihydroxy compounds represented by general formula (A), optional general formula (B) and general formula (C), carbonic acid diesters and/or dicarboxylic acids and/or dicarboxylic acid esters, catalysts and optional auxiliaries are added into a reactor, the air in the reactor is sufficiently replaced by nitrogen for 3 to 5 times, and then the temperature is increased to melt the materials in the reactor, wherein the melting temperature is 180 to 210 ℃, preferably 190 to 200 ℃, and the retention time of the stage is 40 to 100min, preferably 50 to 80min. After the materials are melted, starting stirring, starting pressure reduction or pressure increase control, raising the temperature to the transesterification reaction temperature, wherein the transesterification reaction temperature is 210-250 ℃, preferably 220-240 ℃, and the retention time of the stage is 60-320 min, preferably 150-240 min. Then, the pressure is continuously reduced and the temperature is increased, and the polycondensation reaction is started, wherein the system pressure of the stage is 10-500 Pa (A), preferably 50-100 Pa (A), the reaction temperature of the stage is 230-270 ℃, preferably 230-255 ℃, and the residence time of the stage is 10-120 min, preferably 20-60 min. During the reaction, the small molecular compounds formed are immediately removed by distillation, and a thermoplastic resin composition of high molecular weight is obtained in the final reactor.
The blend of the present invention can be obtained by blending different thermoplastic resin compositions obtained by polymerization in an extruder, kneader, mixer or the like.
The thermoplastic resin composition of the present invention can be used in the field of optical formed articles, such as optical lenses, optical films, and the like.
The invention has the beneficial effects that:
the thermoplastic resin composition has the advantages of high refractive index, good fluidity, easy processing, high temperature resistance, yellowing resistance and high transparency, and can be used in the field of optical lenses. The optical lens adopting the thermoplastic resin composition can make the lens thinner, reduce the weight of the lens and reduce the number of the lens, thereby reducing the cost and having wide application prospect.
The thermoplastic resin composition of the present invention has a refractive index nD of 1.64 to 1.69 at 20 ℃ and a wavelength of 589nm, an Abbe number of not more than 25, and an oriented birefringence [ Delta ] n of 1.0X 10 -3 Below, the molding shrinkage is not higher than 0.6%;
the thermoplastic resin composition has a yellowness index (b) value of not more than 3.0 measured at a thickness of 1mm, an average transmittance at a wavelength of 780nm to 1000nm of 87% or more,
the thermoplastic resin composition has a flexural modulus of greater than 2800MPa and a flexural strength of greater than 90MPa, as determined in accordance with ISO 178.
Detailed Description
The present invention will now be described with reference to the following specific embodiments. It should be noted that the examples are given solely for the purpose of illustration and are not to be construed as limitations on the scope of the invention, as the invention is intended to be limited only by the appended claims, and all insubstantial modifications and variations thereof are intended to be covered by the claims.
1) Weight average molecular weight (Mw): a calibration curve was prepared using standard polystyrene of known molecular weight (molecular weight distribution = 1) using Gel Permeation Chromatography (GPC) with tetrahydrofuran as a developing solvent. Based on the standard curve, mw was calculated from the retention time of GPC.
2) Refractive index (nD): a film having a thickness of 1mm, which was composed of the thermoplastic resin compositions obtained in the examples, was measured for the refractive index (nD) at 20 ℃ and a wavelength of 589nm of the thermoplastic resin composition of the present invention by using an Abbe refractometer according to the method of JIS-K-7142.
3) Abbe number: refractive indices of a film having a thickness of 0.1mm and comprising the polycarbonate resin obtained in examples were measured at 20 ℃ for 486nm (F light), 589nm (D light) and 656nm (C light) using an Abbe refractometer, and Abbe number ν was calculated using the following formula,
ν＝(nD－1)/(nF－nC)。
4) Oriented birefringence (Δ n): after a casting film having a thickness of 0.1mm was cut into a square of 5.0cm square, both ends of the film were inserted into chucks (3.0 cm between the chucks), and stretched 1.5 times at Tg +5 ℃ of a polycarbonate resin. The retardation (Re) at 589nm was measured using an ellipsometer, and the orientation birefringence (. DELTA.n) was determined from the following equation.
Δn＝Re/d
Δ n: oriented birefringence; re: phase difference; d: and (4) thickness.
5) Bending resistance: flexural modulus and flexural strength determined according to ISO 178.
6) Light transmittance: a sample having a thickness of 1mm, which was composed of the polycarbonate resin obtained in the examples, was measured by a haze meter according to JIS-K-7361-1.
7) b value: the obtained polycarbonate resin was vacuum-dried at 120 ℃ for 4 hours, and then injection-molded using an injection molding machine at a cylinder temperature of 270 ℃ and a mold temperature of Tg-10 ℃ to obtain a disk-shaped test sheet having a diameter of 50mm and a thickness of 1 mm. Using the plate piece, the b value was measured in accordance with JIS K7105.
8) Molding shrinkage rate: the test was carried out according to ISO 294-4 standard method.
Some of the raw materials of the reagents used in the examples and comparative examples of the present invention are obtained as follows, and the rest of the raw materials of the reagents are all commercially available products unless otherwise specified:
a-1 and A-2 can be prepared by the method disclosed in patent JP 2009155253A. The nuclear magnetic results of the A-2 compound are as follows: 1H-NMR (400MHz, CDCl) 3 )/δ×10 -6 ：7.90-7.87(m,6H),7.43-7.18(m,14H),4.41(m,4H),3.79(m,4H),3.65-3.56(m,6H),3.44(m,4H)。
B-1 can be prepared by methods disclosed in Japanese patent laid-open Nos. 2014-227387, 2014-227388, and 2015-168658, including (1) a method of reacting 1, 1-binaphthol with ethylene glycol monotoluenesulfonate, (2) a method of reacting binaphthol with a halogenated alkanol or alkylene carbonate, and (3) a method of reacting 1, 1-binaphthol with ethylene carbonate or propylene carbonate.
The B-2 compound can be prepared by the method disclosed in patent RO105571B 1. B-2 CompoundsThe nuclear magnetic results of (a) were as follows: 1H-NMR (400MHz, CDCl 3) delta/. Times.10 -6 ：8.11-8.02(m,4H),7.65(m,2H),7.54-7.41(m,4H),6.92(m,2H),4.84(s,2H),4.43(t,4H),3.69-3.65(m,6H)。
Example 1
0.054g (0.0001 mol) of A1, 33.67g (0.09 mol) of B1, 4.62g (0.0099 mol) of C2, 20.78g (0.097 mol) of diphenyl carbonate, and 3.258. Mu.g (1.0X 10 mol) -8 mol) cesium carbonate is put into a 200ml four-neck flask with a stirrer and a distillation device, nitrogen is substituted for 4 times, the temperature is heated to 190 ℃ under nitrogen atmosphere 101Kpa (A), heating is started for 60min, then the raw materials are confirmed to be completely dissolved, then stirring is started, the pressure is adjusted to 26Kpa (A), simultaneously the temperature is increased to 230 ℃ at the speed of 30 ℃/hr, at the same time, the phenol generated as a byproduct is confirmed to start distilling, the temperature is maintained at 230 ℃ for reaction for 180min, then the temperature is increased to 250 ℃ at the speed of 60 ℃/hr, after the temperature reaches 250 ℃, the pressure is gradually reduced to 50Pa (A) within 1 hour, the reaction is stirred for 60min under the condition, and the reaction is ended. After the reaction was completed, nitrogen gas was introduced into the four-neck flask to return to normal pressure, and the resulting thermoplastic resin composition was taken out, pelletized, molded and subjected to performance evaluation, and the results are shown in table 1.
Example 2
6.2g (0.0099 mol) of A2, 33.03g (0.0851 mol) of B2, 2.95g (0.005 mol) of C1, 23.56g (0.11 mol) of diphenyl carbonate and 2mg (5.0X 10 mol) -5 The same operation as in example 1 was carried out except that mol) of sodium hydroxide was placed in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Example 3
4.84g (0.009 mol) of A1, 2.24g (0.006 mol) of B1, 50.17g (0.085 mol) of C1, 21.64g (0.101 mol) of diphenyl carbonate and 32.74. Mu.g (1.0X 10 mol) -7 The same operation as in example 1 was carried out except that mol) of zirconium acetate was placed in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Example 4
1.88g (0.003 mol) of A2, 31.05g (0.08 mol) of B2, 7.93g (0.017 mol) of C2, 23.14g (0.108 mol) of diphenyl carbonate and 6.806mg (2.0X 10 mol) -5 mol) tetrabutyl titanate is put into a distillation device with a stirrerThe same operation as in example 1 was carried out except that the flask was changed to a 200ml four-necked flask, and the results are shown in Table 1.
Example 5
4.84g (0.009 mol) of A1, 29.50g (0.076 mol) of B2, 8.85g (0.015 mol) of C1, 21.64g (0.101 mol) of diphenyl carbonate and 25.20. Mu.g (3.0X 10 mol) -7 mol) sodium bicarbonate, 228.07. Mu.g (7.0X 10) -7 The same operation as in example 1 was carried out except that mol) cesium carbonate was put in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Example 6
3.13g (0.005 mol) of A2, 11.22g (0.03 mol) of B1, 38.37g (0.065 mol) of C1, 22.49g (0.105 mol) of diphenyl carbonate, and 13.08. Mu.g (3.0X 10 mol) -8 The same operation as in example 1 was carried out except that mol) of lanthanum acetylacetonate was placed in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Example 7
4.84g (0.009 mol) of A1, 19.08g (0.051 mol) of B1, 23.61g (0.04 mol) of C1, 22.71g (0.106 mol) of diphenyl carbonate and 340.32. Mu.g (1.0X 10 mol) -6 The same operation as in example 1 was carried out except that mol) of tetrabutyl titanate was placed in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Example 8
5.38g (0.01 mol) of A1, 41.96g (0.09 mol) of C2, 23.35g (0.109 mol) of diphenyl carbonate, and 9.18. Mu.g (5.0X 10 mol) -8 The same operation as in example 1 was carried out except that mol) of zinc acetate was put into a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Example 9
56.36g (0.09 mol) of A2, 4.66g (0.01 mol) of C2, 22.06g (0.103 mol) of diphenyl carbonate, and 400. Mu.g (1.0X 10 mol) -5 The same operation as in example 1 was carried out except that mol) of sodium hydroxide was placed in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Example 10
21.53g (0.04 mol) of A1, 27.97g (0.06 mol) of C2, 22.49g (0.105 mo)l) Diphenyl carbonate, 97.75. Mu.g (3.0X 10) -7 The same operation as in example 1 was carried out except that mol) cesium carbonate was put in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Example 11
18.79g (0.03 mol) of A2, 41.32g (0.07 mol) of C1, 21.74g (0.1015 mol) of diphenyl carbonate, 73.4. Mu.g (4.0X 10 mol) -7 The same operation as in example 1 was carried out except that mol) of zinc acetate was placed in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Example 12
26.91g (0.05 mol) of A1, 29.51g (0.05 mol) of C1, 22.28g (0.104 mol) of diphenyl carbonate, and 170.16. Mu.g (5.0X 10 mol) -7 The same operation as in example 1 was carried out except that mol) of tetrabutyl titanate was placed in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Comparative example 1
53.82g (0.1 mol) of A1, 22.71g (0.106 mol) of diphenyl carbonate, and 84.01. Mu.g (1.0X 10 mol) -6 The same operation as in example 1 was carried out except that mol) of sodium hydrogencarbonate was charged in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
Comparative example 2
18.71g (0.05 mol) of B1, 23.31g (0.05 mol) of C2, 22.28g (0.104 mol) of diphenyl carbonate, and 436.23. Mu.g (1.0X 10 mol) -6 The same operation as in example 1 was carried out except that mol) of lanthanum acetylacetonate was placed in a 200ml four-necked flask equipped with a stirrer and a distillation apparatus, and the results are shown in Table 1.
TABLE 1
Claims (7)
1. A thermoplastic resin composition comprising a structural unit derived from a compound represented by the general formula (A), a structural unit derived from a compound represented by the general formula (B), and a structural unit derived from a compound represented by the general formula (C),
in the general formula (A), X represents an alkylene group having 1 to 4 carbon atoms, and a and b each independently represent an integer of 1 to 10; r 1 ～R 4 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms,
in the general formula (B), Y represents an alkylene group having 1 to 4 carbon atoms, and c and d each independently represents an integer of 1 to 10; r 5 ～R 8 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms; m represents a direct bond, -O-, -S-, -NH-, a sulfone or sulfoxide group an alkylene group having 1 to 6 carbon atoms, a cycloalkylene group having 5 to 20 carbon atoms,
in the general formula (C), Z represents an alkylene group having 1 to 4 carbon atoms, and e and f each independently represent an integer of 1 to 10; r 9 ～R 12 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms.
2. The thermoplastic resin composition according to claim 1,
wherein the proportion of the structural unit represented by the general formula (A) is 0.1 to 9.9 mol%,
the proportion of the structural unit represented by the general formula (B) is 6 to 90 mol%,
the proportion of the structural unit represented by the general formula (C) is 5 to 85 mol%;
preferably, the first and second liquid crystal materials are,
the proportion of the structural unit represented by the general formula (A) is 3 to 9 mol%,
the proportion of the structural unit represented by the general formula (B) is 30 to 80 mol%,
the proportion of the structural unit represented by the general formula (C) is 15 to 65 mol%.
3. A thermoplastic resin composition comprising a structural unit derived from a compound represented by the general formula (A) and a structural unit derived from a compound represented by the general formula (C),
in the general formula (A), X represents an alkylene group having 1 to 4 carbon atoms, and a and b each independently represent an integer of 1 to 10; r 1 ～R 4 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms,
in the general formula (C), Z represents an alkylene group having 1 to 4 carbon atoms, and e and f each independently represent an integer of 1 to 10; r 9 ～R 12 Each independently represents a hydrogen atom or halogenAn alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, a cycloalkoxy group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms.
4. The thermoplastic resin composition according to claim 3,
wherein the proportion of the structural unit represented by the general formula (A) is 10 to 90 mol%,
the proportion of the structural unit represented by the general formula (C) is 10 to 90 mol%.
5. The thermoplastic resin composition according to claim 4,
the proportion of the structural unit represented by the general formula (A) is 40 to 70 mol%,
the proportion of the structural unit represented by the general formula (C) is 30 to 60 mol%.
6. Use of the thermoplastic resin composition according to any one of claims 1 to 5 for optical formed bodies.
7. The use according to claim 6, the thermoplastic resin composition being used for optical lenses and optical films.
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| CN202211459624.0A Pending CN115926135A (en) | 2022-11-17 | 2022-11-17 | Thermoplastic resin composition for optical forming body and manufacturing method thereof |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170044312A1 (en) * | 2014-05-07 | 2017-02-16 | Mitsubishi Gas Chemical Company, Inc. | Resin produced by polycondensation, and resin composition |
| CN112955422A (en) * | 2018-10-19 | 2021-06-11 | 三菱瓦斯化学株式会社 | Polycyclic compounds |
| CN112961336A (en) * | 2021-04-09 | 2021-06-15 | 万华化学集团股份有限公司 | Polycarbonate resin with stable high refractive index, preparation method and application thereof |
| CN113518934A (en) * | 2019-02-27 | 2021-10-19 | 三菱瓦斯化学株式会社 | Thermoplastic resin, method for producing same, and optical lens |
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- 2022-11-17 CN CN202211459624.0A patent/CN115926135A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170044312A1 (en) * | 2014-05-07 | 2017-02-16 | Mitsubishi Gas Chemical Company, Inc. | Resin produced by polycondensation, and resin composition |
| CN112955422A (en) * | 2018-10-19 | 2021-06-11 | 三菱瓦斯化学株式会社 | Polycyclic compounds |
| CN113518934A (en) * | 2019-02-27 | 2021-10-19 | 三菱瓦斯化学株式会社 | Thermoplastic resin, method for producing same, and optical lens |
| CN112961336A (en) * | 2021-04-09 | 2021-06-15 | 万华化学集团股份有限公司 | Polycarbonate resin with stable high refractive index, preparation method and application thereof |
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