CN108884040A - Novel dihydroxy compounds - Google Patents
Novel dihydroxy compounds Download PDFInfo
- Publication number
- CN108884040A CN108884040A CN201780022066.2A CN201780022066A CN108884040A CN 108884040 A CN108884040 A CN 108884040A CN 201780022066 A CN201780022066 A CN 201780022066A CN 108884040 A CN108884040 A CN 108884040A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- carbon atom
- general formula
- reaction
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 229910052799 carbon Inorganic materials 0.000 claims description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000001118 alkylidene group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 239000002994 raw material Substances 0.000 abstract description 22
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 abstract description 8
- 229920005989 resin Polymers 0.000 abstract description 8
- 239000011347 resin Substances 0.000 abstract description 8
- 125000003118 aryl group Chemical group 0.000 abstract description 6
- -1 benzene oxygen alcohols Chemical class 0.000 description 80
- 238000006243 chemical reaction Methods 0.000 description 64
- 150000001721 carbon Chemical group 0.000 description 48
- 229920000515 polycarbonate Polymers 0.000 description 33
- 239000004417 polycarbonate Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000002585 base Substances 0.000 description 23
- 239000003054 catalyst Substances 0.000 description 23
- 238000000034 method Methods 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 238000002425 crystallisation Methods 0.000 description 17
- 230000008025 crystallization Effects 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 229930185605 Bisphenol Natural products 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 239000003377 acid catalyst Substances 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000005809 transesterification reaction Methods 0.000 description 9
- 150000005690 diesters Chemical class 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 150000003951 lactams Chemical class 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000003252 repetitive effect Effects 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 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 4
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000036632 reaction speed Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
- YBFCBQMICVOSRW-UHFFFAOYSA-N 1-phenylindole Chemical class C1=CC2=CC=CC=C2N1C1=CC=CC=C1 YBFCBQMICVOSRW-UHFFFAOYSA-N 0.000 description 2
- UWCPWBIMRYXUOU-UHFFFAOYSA-N 1-phenylindole-2,3-dione Chemical compound C12=CC=CC=C2C(=O)C(=O)N1C1=CC=CC=C1 UWCPWBIMRYXUOU-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229940061334 2-phenylphenol Drugs 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
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- 229910052796 boron Inorganic materials 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- XHXXWWGGXFUMAJ-UHFFFAOYSA-N methanethiol;sodium Chemical compound [Na].SC XHXXWWGGXFUMAJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 235000010292 orthophenyl phenol Nutrition 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 159000000000 sodium salts Chemical class 0.000 description 2
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- GCLVVFYKIZYIIL-UHFFFAOYSA-N (2-butylphenyl)-diphenylborane Chemical compound CCCCC1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 GCLVVFYKIZYIIL-UHFFFAOYSA-N 0.000 description 1
- PILLNYIUKQDCTC-UHFFFAOYSA-N (4-indol-1-ylphenyl)methanamine Chemical class NCC1=CC=C(C=C1)N1C=CC2=CC=CC=C12 PILLNYIUKQDCTC-UHFFFAOYSA-N 0.000 description 1
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- LXQKTJLIXLCKKL-UHFFFAOYSA-N 2,3-dimethyl-6-phenylphenol Chemical compound OC1=C(C)C(C)=CC=C1C1=CC=CC=C1 LXQKTJLIXLCKKL-UHFFFAOYSA-N 0.000 description 1
- ATGFTMUSEPZNJD-UHFFFAOYSA-N 2,6-diphenylphenol Chemical compound OC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 ATGFTMUSEPZNJD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NKCAOSUQIZMVEC-UHFFFAOYSA-N 2-[3-(aminomethyl)phenyl]phenol Chemical compound NCC1=CC=CC(C=2C(=CC=CC=2)O)=C1 NKCAOSUQIZMVEC-UHFFFAOYSA-N 0.000 description 1
- RVZLNAFRTQWDFX-UHFFFAOYSA-N 2-[4-(aminomethyl)phenyl]phenol Chemical compound C1=CC(CN)=CC=C1C1=CC=CC=C1O RVZLNAFRTQWDFX-UHFFFAOYSA-N 0.000 description 1
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- PGJXFACHLLIKFG-UHFFFAOYSA-N 2-methyl-6-phenylphenol Chemical compound CC1=CC=CC(C=2C=CC=CC=2)=C1O PGJXFACHLLIKFG-UHFFFAOYSA-N 0.000 description 1
- VVUFNNMGVNCTED-UHFFFAOYSA-N 3,6-dimethyl-2-phenylphenol Chemical compound CC1=CC=C(C)C(C=2C=CC=CC=2)=C1O VVUFNNMGVNCTED-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- ACJDNWDUPUMBEW-UHFFFAOYSA-N NCC1=C(C=CC=C1)N1C=CC2=CC=CC=C12 Chemical class NCC1=C(C=CC=C1)N1C=CC2=CC=CC=C12 ACJDNWDUPUMBEW-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000005010 aminoquinolines Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000004637 bakelite Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- PDYNXWPJDVOHDW-UHFFFAOYSA-N bis(3-methylphenyl) carbonate Chemical compound CC1=CC=CC(OC(=O)OC=2C=C(C)C=CC=2)=C1 PDYNXWPJDVOHDW-UHFFFAOYSA-N 0.000 description 1
- PACOTQGTEZMTOT-UHFFFAOYSA-N bis(ethenyl) carbonate Chemical compound C=COC(=O)OC=C PACOTQGTEZMTOT-UHFFFAOYSA-N 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WLFOHIVICZSIKG-UHFFFAOYSA-N n,n-dimethyl-1h-imidazol-2-amine Chemical class CN(C)C1=NC=CN1 WLFOHIVICZSIKG-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 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
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/12—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Indole Compounds (AREA)
Abstract
The raw materials such as aromatic copolycarbonate oligomer or resin, novel dihydroxy compounds with indoline skeleton are suitable as the subject of the invention is to provide a kind of.The above subject can be solved by dihydroxy compounds shown in the following general formula (1).
Description
Technical field
The present invention relates to novel dihydroxy compounds.In particular it relates to being suitable as aromatic copolycarbonate oligomer
Or the raw materials such as resin, dihydroxy compounds with indoline skeleton.
Background technique
In the past, double benzene oxygen alcohols (hydrogen atom of the hydroxyl of bisphenols is substituted by the compound of hydroxy alkyl) were used for poly- carbon
The thermosetting resins raw materials such as the thermoplastic synthetic resins such as acid ester resin raw material, epoxy resin, antioxidant raw material, thermosensitive recording body
The purposes such as raw material, photoresists raw material become higher and higher to performance required by these double benzene oxygen alcohols in recent years.
Further, it has been known that there is bis- (4- (2- hydroxyl-oxethyl) benzene of 3, the 3- with isoindoline skeleton for double benzene oxygen alcohols
Base) -2- phenyl benzyl first lactams (non-patent literature 1).But the heat resistance of the compound, optical characteristics etc. and insufficient, it
Ask further improvement.
Existing technical literature
Non-patent literature
Non-patent literature 1：Izvestiya Akademii Nauk Gruzinskoi SSR,Seriya
Khimicheskaya,1985,vol.11,p.78-80
Summary of the invention
Problems to be solved by the invention
The present invention completed using above situation as background, project be high-fire resistance is provided, high refractive index has
The novel dihydroxy compounds of indoline skeleton.
Means for solving the problems
The inventors of the present invention make great efforts discussion in order to solve the above problems, as a result, it has been found that (3,3- is bis- compared to previous compound
(4- (2- hydroxyl-oxethyl) phenyl) -2- phenyl benzyl first lactams), in bis- (4- (the 2- hydroxyl second of 3, the 3- with indoline skeleton
Oxygroup) phenyl) -1- phenyl -1H- indole-2-ketone hydroxy phenyl skeleton on compound made of substituted-phenyl with more height
Heat resistance, high refractive index, so as to complete the present invention.
The present invention is as described below.
1. dihydroxy compounds shown in the following general formula (1)：
(in formula, R each independently represents the alkylidene of carbon atom number 2 to 6, R1Each independently represent carbon atom number 1 to
Alkoxy, phenyl or the halogen atom of 8 alkyl, carbon atom number 1 to 8, R2Each independently represent hydrogen atom, carbon atom number 1
To 8 alkyl, carbon atom number 1 to 8 alkoxy or halogen atom, R3Indicate the alkyl of carbon atom number 1 to 8, carbon atom number 1 to
8 alkoxy or halogen atom, m indicate that 0 to 2 integer, n indicate 0 to 2 integer, still, R when m is 21It can be identical or not
Together, R when n is 23It may be the same or different).
Invention effect
It is high-fire resistance by the dihydroxy compounds that the present invention obtains and there is high refractive index, therefore it can be expected that as optics material
Expect the excellent effect of the resin raw materials such as polycarbonate, polyester, epoxy resin, the acrylic resin of purposes.
Further, the polycarbonate using dihydroxy compounds of the invention as starting monomer is high-purity and it can be expected that tool
There are a high-fire resistance, high refractive index, especially it can be expected that excellent effect in terms of optical material polycarbonate.
Specific embodiment
Hereinafter, the present invention will be described in detail.
Dihydroxy compounds of the invention is indicated by the following general formula (1)：
(in formula, R each independently represents the alkylidene of carbon atom number 2 to 6, R1Each independently represent carbon atom number 1 to
Alkoxy, phenyl or the halogen atom of 8 alkyl, carbon atom number 1 to 8, R2Each independently represent hydrogen atom, carbon atom number 1
To 8 alkyl, carbon atom number 1 to 8 alkoxy or halogen atom, R3Indicate the alkyl of carbon atom number 1 to 8, carbon atom number 1 to
8 alkoxy or halogen atom, m indicate that 0 to 2 integer, n indicate 0 to 2 integer, wherein R when m is 21It can be identical or not
Together, R when n is 23It may be the same or different).
In above-mentioned general formula (1), R is each independently the alkylidene of carbon atom number 2 to 6, and alkylidene can specifically be enumerated
Such as 1, the Asia 2- second diyl, 1,2- propane diyl, 1,3- propane diyl, pentamethylene, hexa-methylene etc., but preferably carbon atom
The straight-chain or branched alkylidene of number 2 to 4, the particularly preferably alkylidene of carbon atom number 2 or 3.Illustrate above-mentioned general formula herein
(1) hydroxy alkoxy base shown in "-the O-R-OH " in, the bonding position for being bonded to the hydroxyl of alkylidene R are not to be bonded to composition
With the carbon atom (1 carbon atom) of the alkylidene R of ether Direct Bonding.When R is the alkylidene of 3 or more carbon atom number, hydroxyl
Bonding position is preferably the two or three-digit of alkylidene " R ", wherein more preferably 2.Such as 2- hydroxyl second can specifically be enumerated
Oxygroup, 2- hydroxy propyloxy group, 2- hydroxyl -1- methyl ethoxy, 3- hydroxy propyloxy group etc..
R1It is each independently the alkyl of carbon atom number 1 to 8, the alkoxy of carbon atom number 1 to 8, phenyl or halogen atom,
R1For carbon atom number 1 to 8 alkyl when, alkyl is preferably the straight-chain or branched-chain alkyl of carbon atom number 1 to 4, specifically
It can enumerate such as methyl, ethyl, n-propyl, isopropyl, isobutyl group.In the range of not undermining effect of the present invention, like this
Alkyl can have the substituent group such as phenyl, alkoxy.
In addition, R1For carbon atom number 1 to 8 alkoxy when, alkoxy is preferably the straight-chain or branch of carbon atom number 1 to 4
Chain alkoxy can specifically be enumerated such as methoxyl group, ethyoxyl, positive propoxy, isopropoxy.Do not undermining the present invention
In the range of effect, such a alkoxy can have the substituent group such as phenyl, alkoxy.
In addition, R1When for phenyl, in the range of not undermining effect of the present invention, phenyl can have such as alkyl, alkoxy
Equal substituent groups, but preferably unsubstituted phenyl.
In addition, R1When for halogen atom, it is former that halogen atom can specifically enumerate fluorine atom, chlorine atom, bromine atom or iodine
Son.
R1Preferably methyl or phenyl.
R2It is former to be each independently hydrogen atom, the alkyl of carbon atom number 1 to 8, the alkoxy or halogen of carbon atom number 1 to 8
Son, R3For the alkyl of carbon atom number 1 to 8, the alkoxy or halogen atom of carbon atom number 1 to 8, R2、R3For carbon atom number 1 to 8
When alkyl, preferred group or concrete example are and R1Carbon atom number 1 to 8 alkyl preferred group or the identical phase of concrete example
Together, R2、R3For the alkoxy or halogen atomic time of carbon atom number 1 to 8, similarly preferred group or concrete example be respectively and R1's
The preferred group or concrete example of the alkoxy or halogen atom of carbon atom number 1 to 8 are identical.R2Preferably hydrogen atom or first
Base, R3Preferably methyl.
Further, in above-mentioned general formula (1), m 0,1 or 2, preferably 0 or 1, particularly preferably 0, n 0,1 or 2, preferably
It is 0 or 1, particularly preferably 0.
In addition, in above-mentioned general formula (1), about replace with the phenyl of 3 carbon atom Direct Bondings of indoline skeleton "-
O-R-OH " base and phenyl and R1The position of substitution, firstly, "-O-R-OH " base preferably relative to 3 with indoline skeleton
Replaced for the phenyl carbon atom of position carbon atom Direct Bonding in 4 or 2, is more preferably replaced at 4.
In addition, phenyl is replaced preferably for above-mentioned "-O-R-OH " base at ortho position or contraposition, as "-O-R-
OH " base phase for the phenyl carbon atom of the 3 of indoline skeleton carbon atom Direct Bonding when replacing for 4, it is excellent
It is selected as being replaced in 3 or 5, when "-O-R-OH " base is in 2 substitutions, preferably be replaced in 3 or 5.
Further, in above-mentioned general formula (1), R1Preferably for above-mentioned "-O-R-OH " base ortho position or align into
Row replaces, when "-O-R-OH " base for aforementioned and 3 carbon atom Direct Bondings of indoline skeleton phenyl carbon atoms
4 replace and phenyl in 3 substitution, preferably replaced at 5, when "-O-R-OH " base 2 substitutions and phenyl exist
When 3 substitutions, preferably replaced at 5, when "-O-R-OH " base 2 replace and phenyl in 5 substitutions, preferably
Replaced at 3.
Further, when m is 2, R1The position of substitution be preferably：Relative to aforementioned straight with 3 carbon atoms of indoline skeleton
For connecing the phenyl carbon atom of bonding, "-O-R-OH " base is in 4, phenyl in 3, R1Replaced in 5 and 6；Or "-O-
R-OH " base is in 4, phenyl in 3, R1Replaced in 2 and 5.
Therefore, dihydroxy compounds shown in above-mentioned general formula (1) is preferably shown in the following general formula (3)：
(in formula, R1、R2、R3, m, n and formula (1) R1、R2、R3, m, n it is identical, R4Each independently represent hydrogen atom or carbon
The alkyl of atomicity 1 to 4, wherein in the R that each hydroxyl-oxethyl is replaced4Carbon atom number add up to 4 or less).
In above-mentioned general formula (3), R1、R2、R3, the preference of m, n or the R of concrete example and general formula (1)1、R2、R3, m, n it is preferred
Example or concrete example are identical.Further, R4For carbon atom number 1 to 4 alkyl when, can specifically enumerate such as methyl, second
Base, n-propyl etc..Wherein, R4In preferably hydrogen atom or methyl.
In dihydroxy compounds shown in above-mentioned general formula (3), when m is 1, R1The position of substitution preferably relative to indoles
At 5 for the phenyl carbon atom of 3 carbon atom Direct Bondings of quinoline skeleton, when m is 2, R1The position of substitution it is preferably opposite
In with for the phenyl carbon atom of the 3 of indoline skeleton carbon atom Direct Bonding at 5 and 6 or 2 and 5.
Dihydroxy compounds shown in general formula (1) of the invention can specifically be enumerated for example：
Bis- (4- (2- hydroxyl-oxethyl) -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- (2- hydroxy-2-methyl ethyoxyl) -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- (2- hydroxyl -1- methyl ethoxy) -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- (2- hydroxyl-oxethyl) -5- methyl -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (5- ethyl -4- (2- hydroxyl-oxethyl) -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- (2- hydroxyl-oxethyl) -3,5- diphenyl the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- (2- hydroxyl-oxethyl) -5,6- dimethyl -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- (2- hydroxyl-oxethyl) -2,5- dimethyl -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- (2- hydroxyl-oxethyl) -3- (4- aminomethyl phenyl) the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- (2- hydroxyl-oxethyl) -3- (3- aminomethyl phenyl) the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (2- (2- hydroxyl-oxethyl) -5- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (2- (2- hydroxyl-oxethyl) -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- (2- hydroxyl-oxethyl) -3- phenyl) -1- (4- the aminomethyl phenyl) -1H- indol-2-ones of 3,3-；
Bis- (4- (2- hydroxyl-oxethyl) -3- phenyl) -1- (2- the aminomethyl phenyl) -1H- indol-2-ones of 3,3-；And
Bis- (4- (2- hydroxyl-oxethyl) -3- phenyl) -1- (4- methoxyphenyl) -1H- indol-2-ones of 3,3- etc..
There is no particular restriction for its manufacturing method of dihydroxy compounds shown in above-mentioned general formula (1) of the invention, preferably will
Phenylphenol compound shown in N- phenylisatin compound shown in the following general formula (5) and the following general formula (6) as raw material,
Them are made to react in the presence of acid catalyst, thus to obtain bisphenol with indoline skeleton shown in the following general formula (7)
Object is closed, resulting bisphenol compound is reacted with any one of alkylene carbonate esters, alkylene oxides and halogenation alcohols and can get.
(in formula, R3, n and general formula (1) R3, n it is identical).
R3, n preference or the concrete example also R with general formula (1)3, n preference or concrete example it is identical.
N- phenylisatin compound shown in such a above-mentioned general formula (5) can specifically be enumerated for example：
1- phenyl -1H- indoles -2,3- diketone；
1- (4- aminomethyl phenyl) -1H- indoles -2,3- diketone；
1- (2- aminomethyl phenyl) -1H- indoles -2,3- diketone；And
1- (4- methoxyphenyl) -1H- indoles -2,3- diketone etc..
In addition,
(in formula, R1、R2, m and general formula (1) R1、R2, m it is identical).
R1、R2, m preference or the concrete example also R with general formula (1)1、R2, m preference or concrete example it is identical.
Phenylphenol compound shown in such a above-mentioned general formula (6) specifically can be such as：
2- phenylphenol；
6- methyl -2- phenylphenol；
6- ethyl -2- phenylphenol；
2,6- diphenyl phenol；
5,6- dimethyl -2- phenylphenol；
3,6- dimethyl -2- phenylphenol；
2- (4- aminomethyl phenyl) phenol；And
2- (3- aminomethyl phenyl) phenol etc..
In addition,
(in formula, R1、R2、R3, m, n and general formula (1) R1、R2、R3, m, n it is identical).
R1、R2、R3, m, n preference or the concrete example also R with formula (1)1、R2、R3, m, n preference or concrete example phase
Together.
Bisphenol compound shown in above-mentioned general formula (7) is preferably bisphenol compound shown in the following general formula (8)：
(in formula, R1、R2、R3, m, n and general formula (1) R1、R2、R3, m, n it is identical).
R1、R2、R3, m, n preference or the concrete example also R with formula (1)1、R2、R3, m, n preference or concrete example phase
Together.
Bisphenol compound shown in such a above-mentioned general formula (8) can specifically be enumerated for example：
Bis- (4- hydroxyl -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- hydroxy-5-methyl base -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (5- ethyl -4- hydroxyl -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- hydroxyl -3,5- diphenyl the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- hydroxyl -5,6- dimethyl -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- hydroxyl -2,5- dimethyl -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- hydroxyl -3- (4- aminomethyl phenyl) the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- hydroxyl -3- (3- aminomethyl phenyl) the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (2- hydroxyl -5- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (2- hydroxyl -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-；
Bis- (4- hydroxyl -3- phenyl) -1- (4- the aminomethyl phenyl) -1H- indol-2-ones of 3,3-；
Bis- (4- hydroxyl -3- phenyl) -1- (2- the aminomethyl phenyl) -1H- indol-2-ones of 3,3-；And
Bis- (4- hydroxyl -3- phenyl) -1- (4- methoxyphenyl) -1H- indol-2-ones of 3,3- etc..
In addition, above-mentioned alkylene carbonate esters are preferably shown in the following general formula (10)：
(in formula, R4With the R of general formula (3)4It is identical).
R4Preference or the concrete example also R with general formula (3)4Preference or concrete example it is identical.
Alkylene carbonate esters shown in such a above-mentioned general formula (10) can specifically be enumerated for example：
Ethylene carbonate；
Propylene carbonate；And
1,2- butylene carbonate etc..
Further, above-mentioned alkylene oxides are preferably shown in the following general formula (11)：
(in formula, R4With the R of general formula (3)4It is identical).
R4Preference or the concrete example also R with general formula (3)4Preference or concrete example it is identical.
Alkylene oxides shown in such a above-mentioned general formula (11) can specifically be enumerated for example：
Ethylene oxide；
Propylene oxide；And
1,2- epoxy butane etc..
In addition, above-mentioned halogenation alcohols is shown in the following general formula (12)：
X-R-OH general formula (12)
(in formula, R is identical as the R of general formula (1), and X indicates halogen atom, wherein X is not on the carbon atom replaced through hydroxyl
Replaced).
The preference or concrete example of R is also identical as the preference of the R of general formula (1) or concrete example.
Halogenation alcohols shown in such a above-mentioned general formula (12) specifically can be such as：
Ethylene chlorhydrin；
Ethylene bromohyrin；
The chloro- 1- methyl ethanol of 2-；
The bromo- 1- methyl ethanol of 2-；And
2- chloro-2-methyl ethyl alcohol etc..
The manufacturing method of dihydroxy compounds of the invention is not particularly limited, but is described in detail as an example to be condensed
Bisphenol compound shown in reaction synthesis aforementioned formula (7), and using alkylene carbonate esters shown in general formula (10), and manufacture logical
The method of the dihydroxy compounds of formula (1).
Condensation reaction is generally to make N- phenylisatin compound shown in above-mentioned general formula (5) in presence of an acid catalyst and lead to
Phenylphenol compound shown in formula (6) reacts and carries out.Make N- phenylisatin compound and phenylphenol chemical combination first
Object reacts in presence of an acid catalyst, after the resulting reaction mixture of alkali neutralization, carries out partial crystallization, mistake according to known method
Filter, and obtain target product.
When reaction, if as long as the addition molar ratio of the phenylphenol compound relative to N- phenylisatin compound is theory
It is worth (2.0) or more, is not particularly limited, but usually using more than 2.5 times of mole, preferably 2.5 to 20 times of moles
Range, the range of particularly preferably 3 to 10 times moles.
Acid catalyst can enumerate the inorganic acid such as hydrochloric acid, hydrogen chloride gas, 60 to 98% sulfuric acid, 85% phosphoric acid；To first
The organic acids such as benzene sulfonic acid, methanesulfonic acid, oxalic acid, formic acid, trichloroacetic acid or trifluoroacetic acid；Solid acids such as heteropoly acid etc..Preferably chlorine
Change hydrogen.Such a acid catalyst it is different because of reaction condition it is preferable to use measuring, for example, hydrogen chloride gas when, can will be anti-
After answering the air of system to replace with inert gases such as nitrogen, being blown into hydrogen chloride gas makes hydrogen chloride gas in reaction vessel in gas phase
Bulk concentration becomes 75 to 100 capacity %, and the hydrogen cloride concentration in reaction solution is made to become saturated concentration.When for 35% hydrochloric acid, phase
For 100 parts by weight of phenylphenol compound, used with the range of 5 to 70 parts by weight, preferably the range of 10 to 40 parts by weight,
The more preferably range of 20 to 30 parts by weight.
When reaction, optionally cocatalyst can be used together with acid catalyst.Such as use hydrogen chloride gas as
When catalyst, use thio-alcohol as cocatalyst, thus can accelerate reaction speed.Such a thio-alcohol can enumerate alkyl
Mercaptan carboxylic acid's class of thio-alcohol, mercaptan carboxylic acid, preferably the alkyl sulfide alcohols of carbon atom number 1 to 12, carbon atom number 1 to 12, can
Enumerate such as methyl mercaptan, ethanethio, n octylmercaptan, n-laurylmercaptan, the alkali metal salt of classes such as their sodium salt,
Thioacetic acid, β-mercaptopropionic acid etc..Further, it is used above to may be used alone or in combination two types for they.
Relative to the N- phenylisatin compound of raw material, the thio-alcohol usage amount as cocatalyst is usually with 1 to 30
The range of mole % uses, the range of preferably 2 to 10 moles %.
In addition, when reaction, related reaction dissolvent, as long as the N- phenylisatin compound of raw material and phenylphenol compound
Fusing point is low and operational no problem, then without the necessity for using solvent, but to improve operability, the reaction speed etc. when industrial production
It also can be used for reason.As long as reaction dissolvent will not distillate from reactor in reaction temperature and be inertia, nothing to reaction
Especially limitation, but the aromatic hydrocarbon such as toluene, dimethylbenzene can be enumerated；The aliphatic alcohols such as methanol, normal propyl alcohol, isobutanol；Hexane,
The aliphatic hydrocarbons such as heptane, hexamethylene；The carboxylic acid esters such as ethyl acetate, butyl acetate；Or their mixture.In these preferably
To use aliphatic alcohol.
In addition, in order to reduce the freezing point of phenylphenol compound and acid catalyst be promoted to react, therefore can optionally add
A small amount of water.When especially acid catalyst is hydrogen chloride gas, because water can promote the absorption of the hydrogen chloride gas of catalyst, therefore it is preferred that.
When adding water, relative to 100 parts by weight of phenylphenol compound, additive amount is preferably the range of 0.5 to 5.0 parts by weight.
Reaction temperature is different due to the conditions such as the catalyst that uses, but usually 10 to 60 DEG C, preferably 25 to 50 DEG C of model
It encloses.Reaction pressure usually carries out under normal pressure, but according to the boiling point of workable organic solvent, and can also be in pressure or decompression
It is lower to carry out so that reaction temperature becomes in aforementioned range.If being reacted under the conditions of such a, react usually 1 to 30
Or so hour terminates.
Reaction end can confirm via liquid chromatography or gas chromatographic analysis.Preferably with unreacted N- phenylisatin
Object is closed to disappear and can not confirm that target product increased time point is reaction end.
Reaction yield relative to phenylphenol compound is usually 75 to 95 moles of % or so.
After reaction, the aqueous slkalis such as ammonium hydroxide, sodium hydrate aqueous solution are added into resulting reaction mixture to neutralize
Acid catalyst, and obtaining the reaction containing bisphenol compound shown in general formula (7) of the invention terminates mixed liquor.
Known method can be used in the method for terminating mixture separation and purification target product from the reaction.Such as it can will be neutralized
Reaction terminate mixed liquor it is directly cooling or be temporarily heated as it is cooling after uniform solution, or after the partial crystallizations solvents such as methanol are added
It is cooling that crystallization is precipitated and filters the crystallization being precipitated, thus to obtain crude or high-purity target product.
Such resulting bisphenol compound optionally can further be refined into high-purity product.Especially with as poly- carbon
When the raw material dihydroxy phenol of acid esters, high-purity product are preferably formed.Such as again by the crystallization of above-mentioned resulting target product
Be dissolved in suitable solvent (such as the aliphatic ketones solvent such as the aromatic solvents such as toluene, methyl ethyl ketone equal solvent), it is cooling or
The partial crystallizations solvents such as methanol, water are added and cool down again, partial crystallization, filtering, drying.Or replace above-mentioned partial crystallization operation, and reacting
After, autoreaction terminates mixture and is concentrated under reduced pressure reaction dissolvent etc., its residue is refined with col-umn chromatography etc., thus
It can get the high-purity product of target product.
Manufacturing method other than the above-mentioned preferable production process of dihydroxy compounds shown in above-mentioned general formula (1) of the invention
Example, can enumerate N- phenylisatin compound shown in the following general formula (5) and phenyl benzene oxygen alcohols is anti-in presence of an acid catalyst
The method answered and obtained.
Then explanation manufactures the hydroxy alkylated of the dihydroxy compounds of general formula (1) using alkylene carbonate esters.
Hydroxy alkylated usually carries out in the presence of base catalyst.Base catalyst can enumerate such as sodium hydroxide, hydroxide
The base catalysts such as potassium, sodium carbonate, potassium carbonate；The quaternary ammonium phosphonium halides such as bromination tetra-n-butyl ammonium, etamon chloride, tetramethyl ammonium chloride
Object etc., further, it is used above that these base catalysts may be used alone or in combination two types.Base catalyst is preferred like this
Usage amount is different because of reaction condition, but is usually used relative to 1 mole of bisphenol compound with 0.005 to 0.5 mole of range, excellent
It is selected as 0.01 to 0.4 mole of range.
When reaction, the alkylene carbonate esters usage amount relative to bisphenol compound is usual relative to 1 mole of bisphenol compound
For 2 to 10 moles of range, preferably 2.5 to 5 moles of range.Reaction temperature is usually 100 to 150 DEG C, preferably 120 to
130 DEG C of range.
In addition, being carried out when reaction usually using reaction dissolvent.Reaction dissolvent can enumerate the aromatic series such as toluene, dimethylbenzene
Hydrocarbon；The aliphatic alcohols such as n-butyl alcohol, 2- butanol, ethylene glycol；The ketones such as acetone, methyl iso-butyl ketone (MIBK)；Tetrahydrofuran, dioxanes, 1,
The ethers such as 2- diethoxyethane；The aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide or their mixture.
Relative to 100 parts by weight of bisphenol compound, these reaction dissolvent usage amounts are preferably the model of 50 to 300 parts by weight
It encloses, more preferably the range of 100 to 200 parts by weight.
The method of the hydroxy alkylated is not particularly limited, and known method can be used, but for example can be by reaction raw materials, catalysis
Reaction vessel is added together and is warming up to reaction temperature for agent, reaction dissolvent etc., further, can also be molten by bisphenol compound, reaction
Agent, catalyst mixed liquor be warming up to predetermined temperature and thereto instill alkylene carbonate esters.
After reaction, mixed liquor can be terminated in the form of coarse crystallization or high-purity product from reaction known refining methd
Take out target product.Such as after the completion of reaction, terminate that water is added in mixture to reaction, with the excessive alkylene carbonate of water decomposition
Ester.When using base catalyst, acid can be added and neutralized.Then after the solvent being separated from water optionally is added, water washed reservoir
And it removes catalyst or neutralizes salt.Thereafter can oil reservoir be optionally concentrated and is cooled down, or solvent is added simultaneously after concentration oil reservoir
Cooling, partial crystallization, filtering after dissolution, thus to obtain target product.It can get the target product of higher purity if being recrystallized.
Then illustrate the purposes of dihydroxy compounds of the invention.
Explanation is using dihydroxy compounds shown in above-mentioned general formula (1) as the polycarbonate of raw material first.
The polycarbonate is indicated by the following general formula (2)：
(in formula, R each independently represents the alkylidene of carbon atom number 2 to 6, R1Each independently represent carbon atom number 1 to
Alkoxy, phenyl or the halogen atom of 8 alkyl, carbon atom number 1 to 8, R2Each independently represent hydrogen atom, carbon atom number 1
To 8 alkyl, carbon atom number 1 to 8 alkoxy or halogen atom, R3Indicate the alkyl of carbon atom number 1 to 8, carbon atom number 1 to
8 alkoxy or halogen atom, m indicate that 0 to 2 integer, n indicate 0 to 2 integer, wherein R when m is 21It can be identical or not
Together, R when n is 23It may be the same or different).
In above-mentioned general formula (2), R, R in formula1、R2、R3Shown in substituent group preference or concrete example and m, n shown in take
R, R of the regulation of algebra and preferably the position of substitution and general formula (1)1、R2、R3Shown in substituent group preference or concrete example,
And replace the regulation of number and preferably the position of substitution identical shown in m, n.
Therefore, preferably poly- containing repetitive unit in the polycarbonate containing repetitive unit shown in above-mentioned general formula (2)
Carbonic ester is by shown in the following general formula (13)：
(in formula, R1、R2、R3, m, n and general formula (2) R1、R2、R3, m, n it is identical, R4With the R of general formula (3)4It is identical)
R1、R2、R3, the preference of m, n or the R of concrete example and general formula (1)1、R2、R3, m, n preference or concrete example phase
Together, R4Preference or the concrete example also R with general formula (3)4Preference or concrete example it is identical.
There is no particular restriction for polycarbonate its manufacturing method containing repetitive unit shown in above-mentioned general formula (2), can be used
Known any means.Interfacial polymerization, melt transesterification process, solid phase polymerization method, cyclic carbonate can specifically be enumerated
Ring-opening polymerisation method, pyridine method of ester compounds etc., but wherein preferably using dihydroxy compounds and carbonic acid ester precursor as former
Interfacial polymerization, the melt transesterification process of material, particularly preferably by dihydroxy compounds and diphenyl carbonate shown in general formula (1)
Equal carbonates carry out melting state transesterification reaction in the presence of ester exchange catalyst and manufacture.
In the range of not interfering effect of the present invention, as the aromatic series containing repetitive unit shown in above-mentioned general formula (2)
The raw material of polycarbonate and the dihydroxy compounds used, it is possible to use other than dihydroxy compounds shown in above-mentioned general formula (1)
Other dihydroxy compounds (such as bisphenol-A etc.) be used as copolymeric material.
When using copolymeric material, in the limit for not interfering effect of the present invention, in full dihydroxy compounds, master is to be used
There is no particular restriction for the ratio of dihydroxy compounds copolymeric material other than dihydroxy compounds shown in above-mentioned general formula (1), but
The range of preferably 0 to 20 mole %, the range of more preferably 0 to 10 mole %, and the range of more preferably 0 to 5 mole %,
The range of particularly preferably 0 to 2 mole %.
It is further described the polycarbonate containing repetitive unit shown in above-mentioned general formula (2) to melt polycondensation system
The melt transesterification process made.Here, previous known method can be used in melt transesterification process.
Such as raw material dihydroxy compounds is bis- (4- (2- hydroxyl-oxethyl) -3- the phenyl) -1- phenyl -1H- of 3,3-
Reacting on for the above-mentioned aromatic copolycarbonate of acquisition when indol-2-one and oxide spinel diester are diphenyl carbonate is following with anti-
Formula is answered to indicate：
Melting state transesterification reaction is to make dihydroxy compounds and carbonic diester in the presence of a catalyst, together with carbonic diester
It is stirred while being heated in normal pressure or reduced pressure of inert gas atmosphere, phenol generated is made to distillate and carry out.
The carbonic diester for just making dihydroxy compounds react with it can specifically enumerate such as diphenyl carbonate, carbonic acid
Bis- (m-cresol base) esters of two (tolyl) esters (ditolyl carbonate), carbonic acid (bis (m-cresyl) carbonate)
Equal diaryl carbonates；The dialkyl carbonates such as dimethyl carbonate, diethyl carbonate, dicyclohexyl carbonate；Methyl phenyl ester, carbonic acid
The alkyl carbonates aromatic ester such as ethyl phenyl ester, carbonic acid cyclohexyl benzene ester；Or divinyl carbonate, carbonic acid diisopropyl enester, carbonic acid dipropyl
Two enester of the carbonic acid such as enester etc..Preferably diaryl carbonate, particularly preferably diphenyl carbonate.
Degree of decompression when blending ratio, the ester exchange reaction of usual adjustment dihydroxy compounds and carbonic diester, and can obtain
It obtains desired molecular weight and has had adjusted the aromatic copolycarbonate of terminal hydroxyl amount.
In order to obtain the dihydroxy compounds of above-mentioned polycarbonate and the blending ratio of carbonic diester, for relative to dihydroxy
1 mole of compound, carbonic diester is usually using 0.5 to 1.5 mole times, preferably 0.6 to 1.2 mole times.
When melting state transesterification reaction, ester exchange catalyst is optionally used in order to improve reaction speed.
There is no particular restriction for ester exchange catalyst, such as can be used：Lithium, sodium, the hydroxide of caesium, carbonate, bicarbonate
The alkali metal compounds such as the organic alkali metal compounds such as the inorganic alkali metal compounds such as compound, alcoholates, organic carboxylate；
Organic alkaline-earth metal such as the inorganic alkali-earth metals such as hydroxide, carbonate of beryllium, magnesium etc. compound, alcoholates, organic carboxylate
The alkaline earth metal compounds such as compound；The alkalinity such as sodium salt, calcium salt, the magnesium salts of tetramethyl boron, tetraethyl boron, butyl triphenyl boron etc.
Boron compound；The alkalinity such as trivalents phosphorus compound or the quaternary alkylphosphonium salt as derived from these compounds such as triethyl phosphine, three n-propyl phosphines
Phosphorus compound；The alkaline ammonium compounds such as tetramethyl ammonium hydroxide, tetraethyl ammonium hydroxide, tetrabutylammonium；Or 4- amino
Ester exchange catalyst well known to amine compounds such as pyridine, 2- dimethylamino imidazoles, aminoquinoline etc..It is wherein preferably alkali gold
Belong to compound, the particularly preferably cesium compounds such as cesium carbonate, cesium hydroxide.
Catalyst usage amount by with catalyst residue will not to generation polycarbonate cause the range of quality problems to make
It is also different and different because of catalyst type with, suitable additive amount, therefore can not lump together, but generally for example opposite
1 mole of the dihydroxy compounds shown in above-mentioned general formula (1), usually 0.05 to 100 micromole, preferably 0.08 to 50 micro- rubs
You, more preferably 0.1 to 20 micromole, and more preferably 0.1 to 5 micromole.Catalyst directly can add or be dissolved in solvent
And add, it is preferably the solvent for not influencing reaction such as water, phenol as solvent.
In the reaction condition of melting state transesterification reaction, temperature is usually 120 to 360 DEG C of range, preferably 150 to 280
DEG C range, more preferably 180 to 270 DEG C of range.Ester exchange reaction can not be carried out if reaction temperature is too low, if reaction temperature
Degree height then will do it the side reactions such as decomposition reaction, and it is not preferable.Reaction preferably carries out under reduced pressure, and reaction pressure preferably exists
It will not be distillated as the carbonic diester of raw material to outside system and pressure that the phenol of by-product can distillate in reaction temperature.As this
In the reaction condition of sample, reaction would generally terminate at 0.5 to 10 hour or so.
Then optionally, the reaction by so resulting containing polycarbonate terminates the separation that object carries out low molecular weight compositions
After reduction processing, process is dried, thus to obtain the polycarbonate containing repetitive unit shown in above-mentioned general formula (2).
Terminating object by the resulting reaction containing polycarbonate of above-mentioned reaction process is usually melting near reaction temperature
The clear viscous object of state, is solids near room temperature.
The separation reduction for the low molecular weight compositions that can optionally carry out is handled, for for example such as Japanese Unexamined Patent Publication 7-192310
As bulletin is recorded, polycarbonate is dissolved in suitable good solvent, then, poly- carbonic acid is made in the poor solvents such as methanol
Ester precipitating, it is dry, it thus can get the above-mentioned fragrant adoption carbon of graininess, powdery, flake that low molecular weight compositions reduce etc.
Acid esters.
In addition, the more preferable method to obtain high-molecular-weight polycarbonate is such as Japanese Unexamined Patent Publication 3-223330 public affairs
As report, WO00/18822 bulletin are recorded, in the reaction, carries out prepolymerization (first step) and obtain polycarbonate oligomerization
The polycarbonate oligomer is carried out solid phase or swelling solid phase (the second step), thus by object in the presence of a catalyst
It can get high-molecular-weight polycarbonate.
Pre-polymerization in above-mentioned first step is combined into be carried out by melting state transesterification reaction, by dihydroxy compounds and carbonic acid
Diphenyl ester exists while distillating phenol 120 to 360 DEG C of temperature, preferably 150 to 280 DEG C in the presence of a catalyst, especially excellent
It is selected as reacting 0.5 to 10 hour in 180 to 270 DEG C, thus to obtain polycarbonate oligomer.From the side of the operability of the second step
From the point of view of face, polycarbonate oligomer obtained in above-mentioned first step preferably according to known method formed flake, powder or
The solids such as particle.
In the second step, under reduced pressure, optionally into the polycarbonate oligomer obtained in first step, addition adds
The suitable aforementioned ester exchange catalyst such as Jia quaternary alkylphosphonium salt, and inert gas is imported, under stiring, turn in the vitrifying of polycarbonate
It crystallizes under the solid state shape or swelling solid state shape that oligomer will not melt more than temperature and in solid phase, distillates on one side
Remaining phenol is reacted on one side, thus to obtain high-molecular-weight polycarbonate.
The reaction of first step and the reaction of the second step can be carried out or are carried out continuously respectively.
Here, it is 500 to 15000 or so that polycarbonate oligomer, which typically refers to such as weight average molecular weight,.Further, high score
It is 15000 to 100000 or so that son amount polycarbonate, which typically refers to such as weight average molecular weight,.But with dihydroxy chemical combination of the invention
Object is that the polycarbonate of raw material is not limited to such a molecular weight.
In the above described manner resulting polycarbonate be by being set as high-molecular-weight polycarbonate, thus the transparency, heat resistance,
Mechanical property, impact resistance, mobility etc. are excellent, it can be expected that being used in optics used in CD, smartphone etc.
The optical applications such as optical film used in lens, flat-panel monitor etc., or it can be expected that as engineering plastics be used in automotive field,
The various fields such as electrical/electronic field, various containers.
When further, polycarbonate oligomer can be used not only as with various polymerizations manufacture high-molecular-weight polycarbonate
Raw material is also widely used as surface modifier, fire retardant, ultraviolet absorbing agent, mobility modifying agent, plasticiser, resin alloy
With additives such as the polymer modifiers such as solubilizer.
Further, as other purposes, dihydroxy compounds of the invention be using terminal hydroxyl, in addition to polycarbonate with
It is outer also it can be expected that be used as epoxy resin, oxetane resin, acrylic resin, polyester, polyarylate, polyether-ether-ketone, polysulfones,
The resin raw materials such as novolaks, bakelite (resol), other light sensitivity form raw material, agent addition agent against corrosion, colour developing
Agent, antioxidant.
Especially it can be expected that reacting by dihydroxy compounds of the invention and acrylic acid etc. and obtaining diacrylate etc. and be used as
Acrylic monomers or acrylic resin raw material, and it can be expected that as using optics made of them to apply using for material firmly.
Embodiment
The present invention is further illustrated by the following examples, but the present invention is not limited to these embodiments.
In addition, softening point, refractive index in embodiment, purity measure by the following method.
[analysis method]
1. softening point measurement
Device：Shimadzu Scisakusho Ltd (Zhu formula Hui She Island Jin System makees institute) DSC-60 DIFFERENTIAL processed
SCANNING CALORIMETER。
Elevated Temperature Conditions：10 DEG C/min (30 DEG C → 200 DEG C).
Atmosphere gas：Nitrogen (flow：50ml/ minutes).
Measuring method：
The 1st measurement is carried out with above-mentioned Elevated Temperature Conditions, and fusing point is measured by its wave crest that absorbs heat.
Thereafter identical sample is cooled to room temperature and carries out the 2nd measurement in the same terms, be softening with its wave crest that absorbs heat
Point.
2. detecting refractive index
Device：Capital of a country electronics industry Co., Ltd. (capital of a country Electricity Industrial Co., Ltd) Refractometer RA- processed
500N。
Measuring method：
The THF solution (THF refractive index 1.40) for preparing concentration 10,15,30%, by extrapolation by its solution index meter
Calculate the refractive index of measurement compound.
3. purity testing
Device：Shimadzu Scisakusho Ltd CLASS-LC10.
Pump：LC-10ATvp.
Column oven：CTO-10Avp.
Detector：SPD-10Avp.
Tubing string：Shim-pack CLC-ODS internal diameter 6mm, length 150mm.
Oven temperature：50℃.
Flow：1.0ml/min.
Mobile phase：(A) acetonitrile, (B) 0.2vol% acetic acid aqueous solution.
Gradient condition：(A) volume % (time started away from analysis)
60% (0min) → 60% (20min) → 100% (40min) → 100% (50min).
Sample injection rate：20μl.
Detection wavelength：280nm.
1 > of < reference example
The manufacture of bis- (4- hydroxyl -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-
Into the four-hole boiling flask for having thermometer, blender, cooling tube be added 2- phenylphenol 680.4g (4.00 moles),
1- phenyl -1H-Indole-2,3-dione 223g (1.00 moles) after replacing with nitrogen to reaction vessel, is blown into chlorination with 40 DEG C
Hydrogen simultaneously replaces internal system.Thereafter adding 15% methyl mercaptan sodium water solution 22.3g, (methyl mercaptan sodium is 0.05
Mole), it is stirred 19 hours at 40 DEG C.16% sodium hydrate aqueous solution 409.4g (sodium hydroxide 1.64 is added after reaction
Mole) neutralized.After resulting solution is warming up to 78 DEG C, methanol 612.0g is added, is cooled to 35 DEG C.The knot that will be precipitated
Crystalline substance filters and obtains white crystals 691.7g.
To resulting white crystals addition toluene 2026.2g, methyl ethyl ketone 675.4g and after dissolving, water 675.4g is added
And be stirred at 80 DEG C, stand after remove water layer, repeat the water washing operations of 2 removal water layers.Oil reservoir is heated up
To 107 DEG C, after removing solvent 919.3g by distillation, 25 DEG C are cooled to, the crystallization being precipitated is filtered.Under reduced pressure by gained
Crystallizing and drying, thus to obtain bis- (4- hydroxyl -3- the phenyl) -1- phenyl -1H- indol-2-one 417.6g of 3,3-.
Purity：99.0% (high performance liquid chroma- tography area %).
Yield：77% (relative to 1- phenyl -1H- indoles -2,3- diketone).
Fusing point：180 DEG C/218 DEG C (Differential Scanning Calorimetry analysis).
Proton NMR spectral (400MHz, solvent DMSO-D6, standard TMS)
Chemical shift (signal shape, proton number)
6.8ppm (d, 1H), 7.0ppm (d, 2H), 7.1ppm (dd, 2H), 7.2ppm (m, 3H), 7.2 to 7.3ppm (m,
3H), 7.4ppm (t, 4H), 7.4 to 7.5ppm (m, 8H), 7.5 to 7.6ppm (m, 2H), 9.7ppm (s, 2H).
1 > of < embodiment
The manufacture of bis- (4- (2- hydroxyl-oxethyl) -3- the phenyl) -1- phenyl -1H- indol-2-ones of 3,3-
Bis- (the 4- hydroxyls of 3,3- obtained in reference example 1 are added into the four-hole boiling flask for having thermometer, blender, cooling tube
Base -3- phenyl) -1- phenyl -1H- indol-2-one 208.5g (0.38 mole), ethylene carbonate 97.6g (1.11 moles),
Bromination tetra-n-butyl ammonium 1.23g (0.004 mole), 48% sodium hydrate aqueous solution 2.23g (sodium hydroxide is 0.03 mole), 1-
Butanol 312.7g after being replaced with nitrogen to reaction vessel, is stirred 15 hours in 120 DEG C.Water 121.3g is added after reaction,
It stirs 6 hours in 95 DEG C and is stirred 1 hour in 105 DEG C.Then acetic acid 1.0g (0.22 mole) is added, so that the pH of water layer is adjusted
As 5 to 6.Water further is added to oil reservoir, water layer is removed after 80 DEG C of stirrings, after adding n-butyl alcohol 728.6g, passes through distillation
Distillate distillation part 615.6g.Resulting solution is cooled to 25 DEG C, the crystallization being precipitated is filtered.By resulting crystallizing and drying,
Thus to obtain bis- (4- (2- hydroxyl-oxethyl) -3- the phenyl) -1- phenyl -1H- indol-2-one 209.7g of 3,3-.
Purity：99.2% (high performance liquid chroma- tography area %).
Yield：87% (relative to bis-phenol).
Fusing point：185 DEG C (Differential Scanning Calorimetry analysis).
Softening point：93 DEG C (Differential Scanning Calorimetry analysis).
Refractive index (nD20)：1.63.
Proton NMR spectral (400MHz, solvent DMSO-D6, standard TMS)
Chemical shift (signal shape, proton number)
3.7ppm (m, 4H), 4.1ppm (t, 4H), 4.8ppm (m, 2H), 6.8ppm (d, 1H), 7.1 to 7.2ppm (m,
3H), 7.2 to 7.3ppm (m, 7H), 7.4ppm (t, 4H), 7.5ppm (m, 8H), 7.6ppm (m, 8H).
1 > of < comparative example
The manufacture of bis- (4- (2- hydroxyl-oxethyl) the phenyl) -2- phenyl benzyl first lactams of 3,3-
(process 1)
Aniline 902.5g (9.70 moles) are added into the four-hole boiling flask for having thermometer, blender, cooling tube, with nitrogen pair
After reaction vessel is replaced, methanesulfonic acid 192.7g is instilled in system while being maintained at 85 to 95 DEG C.Thereafter 90
To 100 DEG C of addition phenolphthalein 385.4g (1.21 moles), after addition, it is small while being maintained at 147 to 153 DEG C to stir 21.5
When.After reaction, it cools down and is cooled to 30 DEG C after 90 DEG C of addition water 1480.6g in 110 DEG C of addition toluene 1480.6g,
The crystallization being precipitated is filtered, thus to obtain coarse crystallization 481.6g.
Toluene 913.4g, methanol 228.4g are added to above-mentioned resulting coarse crystallization, after 71 DEG C are stirred 5 hours, is cooled to
30 DEG C, the crystallization being precipitated is filtered.Under reduced pressure by resulting crystallizing and drying, thus to obtain 3,3- bis- (4- hydroxy phenyls)-
2- phenyl benzyl first lactams 347.2g.
Purity：99.6% (high performance liquid chroma- tography area %).
Yield：75% (relative to phenolphthalein).
Fusing point：291.5 DEG C (Differential Scanning Calorimetry analysis).
(process 2)
Bis- (the 4- hydroxyls of 3,3- obtained in process 1 are added into the four-hole boiling flask for having thermometer, blender, cooling tube
Phenyl) -2- phenyl benzyl first lactams 30.0g (0.076 mole), ethylene carbonate 19.5g (0.22 mole), 48% potassium hydroxide
Aqueous solution 0.44g (potassium hydroxide is 0.0038 mole), n-butyl alcohol 45.0g, after being replaced with nitrogen to reaction vessel, in 115
It is stirred 11 hours to 118 DEG C.After reaction, water 2.7g is added, is stirred 3 hours in 106 to 109 DEG C.Then 10% second is added
Sour 2.2g, so that the pH adjustment of water layer becomes 4 to 5.To resulting oil reservoir add methyl iso-butyl ketone (MIBK), further add water and in
Water layer is removed after 80 to 85 DEG C of stirrings, carries out the operation of 2 removal water layers.Resulting oil reservoir is warming up to 125 DEG C, passes through steaming
Distillate distillation part 50.0g.After adding acetone and water to resulting solution, 30 DEG C are cooled to, the crystallization being precipitated is filtered.It will
Resulting crystallizing and drying, thus to obtain bis- (4- (2- hydroxyl-oxethyl) the phenyl) -2- phenyl benzyl first lactams 28.5g of 3,3-.
Purity：96.7% (high performance liquid chroma- tography area %).
Yield：78% (relative to bis- (4- the hydroxy phenyl) -2- phenyl benzyl first lactams of 3,3-).
Fusing point：155 DEG C (Differential Scanning Calorimetry analysis).
Softening point：68 DEG C (Differential Scanning Calorimetry analysis).
Refractive index (nD20)：1.60.
1 resulting compound and fusing point, softening point, folding by comparing the resulting compound of example 1 through the foregoing embodiment
Rate is penetrated to be recorded in respectively in table 1.
[table 1]
| The compound of embodiment 1 | The compound of comparative example 1 | |
| Fusing point (DEG C) | 185 | 155 |
| Softening point (DEG C) | 93 | 68 |
| Refractive index (nD20) | 1.63 | 1.60 |
Compared with the compound of well known comparative example 1, (the softening of the compound heat resistance as obtained by the embodiment of the present invention 1
Point temperature) it is higher and there is higher refractive index, therefore it is able to confirm that as the polycarbonate starting material as optical material purposes.
Claims (1)
1. a kind of dihydroxy compounds is indicated by the following general formula (1)：
In formula, R each independently represents the alkylidene of carbon atom number 2 to 6, R1Each independently represent the alkane of carbon atom number 1 to 8
Base, the alkoxy of carbon atom number 1 to 8, phenyl or halogen atom, R2Each independently represent hydrogen atom, carbon atom number 1 to 8
The alkoxy or halogen atom of alkyl, carbon atom number 1 to 8, R3Indicate the alkyl of carbon atom number 1 to 8, the alkane of carbon atom number 1 to 8
Oxygroup or halogen atom, m indicate that 0 to 2 integer, n indicate 0 to 2 integer, wherein R when m is 21It may be the same or different, n 2
When R3It may be the same or different.
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| PCT/JP2017/011625 WO2017170094A1 (en) | 2016-03-28 | 2017-03-23 | Novel dihydroxy compound |
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| US5914431A (en) * | 1996-09-23 | 1999-06-22 | Bayer Ag | Cocatalysts for the synthesis of bisphenols |
| JP2001206863A (en) * | 2000-01-25 | 2001-07-31 | Osaka Gas Co Ltd | Fluorene compound and method for the same |
| US20090131599A1 (en) * | 2004-06-28 | 2009-05-21 | Vinod Kumar Rai | Methods for producing and purifying 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine monomers and polycarbonates derived therefrom |
| JP2009155252A (en) * | 2007-12-26 | 2009-07-16 | Osaka Gas Co Ltd | Alcohol having fluorene skeleton |
| JP2009256342A (en) * | 2008-03-27 | 2009-11-05 | Osaka Gas Co Ltd | Method for producing alcohol having fluorene skeleton |
| CN101805501A (en) * | 2009-02-17 | 2010-08-18 | 三菱瓦斯化学株式会社 | Poly carbonate resin composition and manufacture method thereof |
| CN102741318A (en) * | 2010-02-03 | 2012-10-17 | 沙伯基础创新塑料知识产权有限公司 | Copolycarrbonate-polyesters and uses thereof |
| WO2016014536A1 (en) * | 2014-07-22 | 2016-01-28 | Sabic Global Technologies B.V. | High heat monomers and methods of use thereof |
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|---|---|---|---|---|
| JPH08183853A (en) * | 1994-12-28 | 1996-07-16 | Nippon G Ii Plast Kk | Polycarbonate, polycarbonate composition and production thereof |
| DE102006046330A1 (en) * | 2006-09-28 | 2008-04-03 | Bayer Materialscience Ag | Polycarbonates and copolycarbonates with improved metal adhesion |
| JP2015000549A (en) | 2013-06-17 | 2015-01-05 | 富士ゼロックス株式会社 | Light irradiation device, and image forming apparatus |
| JP6155999B2 (en) * | 2013-09-13 | 2017-07-05 | Jsr株式会社 | Resin molded body, film / lens, transparent conductive film, resin composition, polymer |
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2017
- 2017-03-23 KR KR1020187029622A patent/KR102263143B1/en active Active
- 2017-03-23 CN CN201780022066.2A patent/CN108884040A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5914431A (en) * | 1996-09-23 | 1999-06-22 | Bayer Ag | Cocatalysts for the synthesis of bisphenols |
| JP2001206863A (en) * | 2000-01-25 | 2001-07-31 | Osaka Gas Co Ltd | Fluorene compound and method for the same |
| US20090131599A1 (en) * | 2004-06-28 | 2009-05-21 | Vinod Kumar Rai | Methods for producing and purifying 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine monomers and polycarbonates derived therefrom |
| JP2009155252A (en) * | 2007-12-26 | 2009-07-16 | Osaka Gas Co Ltd | Alcohol having fluorene skeleton |
| JP2009256342A (en) * | 2008-03-27 | 2009-11-05 | Osaka Gas Co Ltd | Method for producing alcohol having fluorene skeleton |
| CN101805501A (en) * | 2009-02-17 | 2010-08-18 | 三菱瓦斯化学株式会社 | Poly carbonate resin composition and manufacture method thereof |
| CN102741318A (en) * | 2010-02-03 | 2012-10-17 | 沙伯基础创新塑料知识产权有限公司 | Copolycarrbonate-polyesters and uses thereof |
| WO2016014536A1 (en) * | 2014-07-22 | 2016-01-28 | Sabic Global Technologies B.V. | High heat monomers and methods of use thereof |
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| TWI712587B (en) | 2020-12-11 |
| WO2017170094A1 (en) | 2017-10-05 |
| JPWO2017170094A1 (en) | 2019-02-07 |
| JP7267008B2 (en) | 2023-05-01 |
| TW201802069A (en) | 2018-01-16 |
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