TWI278470B - Method of preparing transparent silicone-containing copolycarbonates - Google Patents
Method of preparing transparent silicone-containing copolycarbonates Download PDFInfo
- Publication number
- TWI278470B TWI278470B TW092122010A TW92122010A TWI278470B TW I278470 B TWI278470 B TW I278470B TW 092122010 A TW092122010 A TW 092122010A TW 92122010 A TW92122010 A TW 92122010A TW I278470 B TWI278470 B TW I278470B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- polycarbonate
- copolycarbonate
- weight
- phenol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 58
- 229920001296 polysiloxane Polymers 0.000 title abstract 5
- -1 siloxane chains Chemical group 0.000 claims abstract description 75
- 239000004417 polycarbonate Substances 0.000 claims abstract description 68
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 67
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 49
- 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 claims abstract description 27
- 238000010406 interfacial reaction Methods 0.000 claims abstract description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 33
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 32
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 150000002923 oximes Chemical class 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 20
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims description 18
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 17
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 16
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 150000002576 ketones Chemical class 0.000 claims description 12
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 claims description 11
- 150000001491 aromatic compounds Chemical class 0.000 claims description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002981 blocking agent Substances 0.000 claims description 8
- 239000001294 propane Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 229930004069 diterpene Natural products 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000004141 diterpene derivatives Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical group CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 229930013930 alkaloid Natural products 0.000 claims description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 claims 2
- YWCLFFKWGMUSPB-UHFFFAOYSA-N 4-cyclohexyl-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2CCCCC2)=C1 YWCLFFKWGMUSPB-UHFFFAOYSA-N 0.000 claims 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims 1
- LSMSSYSRCUNIFX-ONEGZZNKSA-N 1-methyl-4-[(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=C(C)C=C1 LSMSSYSRCUNIFX-ONEGZZNKSA-N 0.000 claims 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 claims 1
- SPDODUOTLRAEOR-UHFFFAOYSA-N 2,6-dimethyl-4-phenylphenol Chemical compound CC1=C(O)C(C)=CC(C=2C=CC=CC=2)=C1 SPDODUOTLRAEOR-UHFFFAOYSA-N 0.000 claims 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 claims 1
- WOGWYSWDBYCVDY-UHFFFAOYSA-N 2-chlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=CC(=O)C=CC1=O WOGWYSWDBYCVDY-UHFFFAOYSA-N 0.000 claims 1
- VWCDBDPQUBJQDU-UHFFFAOYSA-N 2-methyl-4-(2-phenylpropan-2-yl)phenol Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=CC=CC=2)=C1 VWCDBDPQUBJQDU-UHFFFAOYSA-N 0.000 claims 1
- WWDJZBIPKJNQBZ-UHFFFAOYSA-N 2-methyl-4-phenylphenol Chemical compound C1=C(O)C(C)=CC(C=2C=CC=CC=2)=C1 WWDJZBIPKJNQBZ-UHFFFAOYSA-N 0.000 claims 1
- PGJXFACHLLIKFG-UHFFFAOYSA-N 2-methyl-6-phenylphenol Chemical compound CC1=CC=CC(C=2C=CC=CC=2)=C1O PGJXFACHLLIKFG-UHFFFAOYSA-N 0.000 claims 1
- 229940061334 2-phenylphenol Drugs 0.000 claims 1
- BIOIMCYUMXGFMM-UHFFFAOYSA-N 4-(4-hydroxy-3-octylphenyl)-2-octylphenol Chemical group C1=C(O)C(CCCCCCCC)=CC(C=2C=C(CCCCCCCC)C(O)=CC=2)=C1 BIOIMCYUMXGFMM-UHFFFAOYSA-N 0.000 claims 1
- ZLVFYUORUHNMBO-UHFFFAOYSA-N 4-bromo-2,6-dimethylphenol Chemical compound CC1=CC(Br)=CC(C)=C1O ZLVFYUORUHNMBO-UHFFFAOYSA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- MEPYMUOZRROULQ-UHFFFAOYSA-N 4-tert-butyl-2,6-dimethylphenol Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1O MEPYMUOZRROULQ-UHFFFAOYSA-N 0.000 claims 1
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims 1
- VGBFJBZMHYAOQC-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)[Ru] Chemical compound C(CCCCCCCCCCCCCCCCC)[Ru] VGBFJBZMHYAOQC-UHFFFAOYSA-N 0.000 claims 1
- DXEFREBWYDZERU-UHFFFAOYSA-N CC1(C=C(CC(C1)C)C1=CC=C(C=C1)O)C Chemical compound CC1(C=C(CC(C1)C)C1=CC=C(C=C1)O)C DXEFREBWYDZERU-UHFFFAOYSA-N 0.000 claims 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims 1
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 claims 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000009830 intercalation Methods 0.000 claims 1
- 235000010292 orthophenyl phenol Nutrition 0.000 claims 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims 1
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims 1
- 229940032091 stigmasterol Drugs 0.000 claims 1
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims 1
- 235000016831 stigmasterol Nutrition 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 230000009747 swallowing Effects 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 229930185605 Bisphenol Natural products 0.000 abstract description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 100
- 239000000243 solution Substances 0.000 description 84
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 57
- 239000000047 product Substances 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 32
- 239000005770 Eugenol Substances 0.000 description 32
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 32
- 229960002217 eugenol Drugs 0.000 description 32
- 239000000203 mixture Substances 0.000 description 31
- 238000007792 addition Methods 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 21
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000052 vinegar Substances 0.000 description 18
- 235000021419 vinegar Nutrition 0.000 description 18
- 239000007789 gas Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 14
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 239000008367 deionised water Substances 0.000 description 12
- 229910021641 deionized water Inorganic materials 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 244000223014 Syzygium aromaticum Species 0.000 description 10
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229910052707 ruthenium Inorganic materials 0.000 description 7
- 230000003068 static effect Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 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 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 125000005702 oxyalkylene group Chemical group 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000001117 sulphuric acid Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- CTNHHQQQYSIJTM-UHFFFAOYSA-N NN.C(O)(=O)Cl Chemical compound NN.C(O)(=O)Cl CTNHHQQQYSIJTM-UHFFFAOYSA-N 0.000 description 3
- 206010036790 Productive cough Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000000889 atomisation Methods 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000003221 ear drop Substances 0.000 description 3
- 229940047652 ear drops Drugs 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000003544 oxime group Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 210000003802 sputum Anatomy 0.000 description 3
- 208000024794 sputum Diseases 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VLHWNGXLXZPNOO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(2-morpholin-4-ylethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CCN1CCOCC1 VLHWNGXLXZPNOO-UHFFFAOYSA-N 0.000 description 2
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 2
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 2
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 2
- JEVVKJMRZMXFBT-XWDZUXABSA-N Lycophyll Natural products OC/C(=C/CC/C(=C\C=C\C(=C/C=C/C(=C\C=C\C=C(/C=C/C=C(\C=C\C=C(/CC/C=C(/CO)\C)\C)/C)\C)/C)\C)/C)/C JEVVKJMRZMXFBT-XWDZUXABSA-N 0.000 description 2
- 240000000233 Melia azedarach Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OAIJSZIZWZSQBC-GYZMGTAESA-N lycopene Chemical compound CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C OAIJSZIZWZSQBC-GYZMGTAESA-N 0.000 description 2
- 229960004999 lycopene Drugs 0.000 description 2
- 235000012661 lycopene Nutrition 0.000 description 2
- 239000001751 lycopene Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 2
- URZZPDIVHLEKAQ-UHFFFAOYSA-N 1,1,2,2-tetramethylhydrazine hydrate Chemical compound O.CN(N(C)C)C URZZPDIVHLEKAQ-UHFFFAOYSA-N 0.000 description 1
- JCMVPOVHKWWBAU-UHFFFAOYSA-N 1,2-dichlorohydrazine Chemical compound ClNNCl JCMVPOVHKWWBAU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OEAJNZQFAHZXAB-UHFFFAOYSA-N 1,4-dioxane;methane Chemical compound C.C1COCCO1 OEAJNZQFAHZXAB-UHFFFAOYSA-N 0.000 description 1
- AQDUJQUHCZDQBC-UHFFFAOYSA-N 1-azidodecane Chemical compound CCCCCCCCCCN=[N+]=[N-] AQDUJQUHCZDQBC-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- ONRLWIDOLZZIAG-UHFFFAOYSA-N 2,3-dimethyl-4-nonylphenol Chemical compound CC=1C(=C(C=CC1CCCCCCCCC)O)C ONRLWIDOLZZIAG-UHFFFAOYSA-N 0.000 description 1
- RGHWQVGKWVTRJV-UHFFFAOYSA-N 2-O-chloro 1-O-decyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCl RGHWQVGKWVTRJV-UHFFFAOYSA-N 0.000 description 1
- UFUBQDNODUUQTD-UHFFFAOYSA-N 2-bromo-4-propylphenol Chemical compound CCCC1=CC=C(O)C(Br)=C1 UFUBQDNODUUQTD-UHFFFAOYSA-N 0.000 description 1
- WRLVTKZXVVEUPL-UHFFFAOYSA-N 2-chloro-4-propylphenol Chemical compound CCCC1=CC=C(O)C(Cl)=C1 WRLVTKZXVVEUPL-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- FLYFXPODDPEONH-UHFFFAOYSA-N 2-chloroacetic acid oxalic acid Chemical compound C(C(=O)O)(=O)O.ClCC(=O)O FLYFXPODDPEONH-UHFFFAOYSA-N 0.000 description 1
- NOJIVXPLDDHVSU-UHFFFAOYSA-N 2-decoxyphenol Chemical compound CCCCCCCCCCOC1=CC=CC=C1O NOJIVXPLDDHVSU-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- ZNVLKMKGFWEUPV-UHFFFAOYSA-N 2-propan-2-yl-4-propylphenol Chemical compound CCCC1=CC=C(O)C(C(C)C)=C1 ZNVLKMKGFWEUPV-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical group C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- NDUMSJWWRWOBDX-UHFFFAOYSA-N 3-methyl-4-propylphenol Chemical compound CCCC1=CC=C(O)C=C1C NDUMSJWWRWOBDX-UHFFFAOYSA-N 0.000 description 1
- ASURBSPIYIISGI-UHFFFAOYSA-N 4-(3,3,5-trimethylcyclohexyl)phenol Chemical compound C1C(C)(C)CC(C)CC1C1=CC=C(O)C=C1 ASURBSPIYIISGI-UHFFFAOYSA-N 0.000 description 1
- WUGKVYDVIGOPSI-UHFFFAOYSA-N 4-(4-hydroxy-3-methylphenyl)-2-methylphenol Chemical group C1=C(O)C(C)=CC(C=2C=C(C)C(O)=CC=2)=C1 WUGKVYDVIGOPSI-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 1
- WRPQACICCKFGJO-UHFFFAOYSA-N C1=CC=CC=C1.O.Cl.Cl Chemical compound C1=CC=CC=C1.O.Cl.Cl WRPQACICCKFGJO-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- ILLREIIRUBCTMC-UHFFFAOYSA-N CCCCCCCCCCN(N)Cl Chemical compound CCCCCCCCCCN(N)Cl ILLREIIRUBCTMC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IMXSCCDUAFEIOE-UHFFFAOYSA-N D-Octopin Natural products OC(=O)C(C)NC(C(O)=O)CCCN=C(N)N IMXSCCDUAFEIOE-UHFFFAOYSA-N 0.000 description 1
- IMXSCCDUAFEIOE-RITPCOANSA-N D-octopine Chemical compound [O-]C(=O)[C@@H](C)[NH2+][C@H](C([O-])=O)CCCNC(N)=[NH2+] IMXSCCDUAFEIOE-RITPCOANSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-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
- 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
- 206010021703 Indifference Diseases 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 1
- NCRSOPWSHUELID-UHFFFAOYSA-N OC(Cl)=O.[O] Chemical compound OC(Cl)=O.[O] NCRSOPWSHUELID-UHFFFAOYSA-N 0.000 description 1
- OOVLMFMECLBCJR-UHFFFAOYSA-K O[Sb](O)(Cl)=O Chemical compound O[Sb](O)(Cl)=O OOVLMFMECLBCJR-UHFFFAOYSA-K 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 description 1
- 244000297179 Syringa vulgaris Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- UBMMSPUYJSLCNW-UHFFFAOYSA-N [O].C1COC1 Chemical compound [O].C1COC1 UBMMSPUYJSLCNW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000012801 analytical assay Methods 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- AEETWQIZFGAMIM-UHFFFAOYSA-K azane;trichlororuthenium;dihydrochloride Chemical compound [NH4+].[NH4+].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Ru+3] AEETWQIZFGAMIM-UHFFFAOYSA-K 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000005586 carbonic acid group Chemical group 0.000 description 1
- HUGJLQDIAQYJEV-UHFFFAOYSA-N carbonochloridic acid hydrate Chemical compound O.OC(Cl)=O HUGJLQDIAQYJEV-UHFFFAOYSA-N 0.000 description 1
- MAWQEIYFMMWJQO-UHFFFAOYSA-N carbonochloridic acid sulfuric acid Chemical compound S(=O)(=O)(O)O.C(O)(=O)Cl MAWQEIYFMMWJQO-UHFFFAOYSA-N 0.000 description 1
- DNBASDSRFRZPQT-UHFFFAOYSA-N carbonochloridic acid;oxane Chemical compound OC(Cl)=O.C1CCOCC1 DNBASDSRFRZPQT-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-O dodecylazanium Chemical compound CCCCCCCCCCCC[NH3+] JRBPAEWTRLWTQC-UHFFFAOYSA-O 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- ROBANYUFXBOZJF-UHFFFAOYSA-N ethyl 2-chlorodecanoate Chemical compound CCCCCCCCC(Cl)C(=O)OCC ROBANYUFXBOZJF-UHFFFAOYSA-N 0.000 description 1
- 230000008713 feedback mechanism Effects 0.000 description 1
- TWVBEFREQNKFGN-UHFFFAOYSA-N formic acid;hydrazine Chemical compound NN.OC=O TWVBEFREQNKFGN-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000008241 heterogeneous mixture 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
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- QEVULWLKZSZUIB-UHFFFAOYSA-N oxalic acid;phenol Chemical compound OC(=O)C(O)=O.OC1=CC=CC=C1 QEVULWLKZSZUIB-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- KTJVTXXYLUAKDI-UHFFFAOYSA-N oxirane phenol Chemical compound C1(=CC=CC=C1)O.C1(=CC=CC=C1)O.O1CC1.O1CC1 KTJVTXXYLUAKDI-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- CJJMLLCUQDSZIZ-UHFFFAOYSA-N oxobismuth Chemical group [Bi]=O CJJMLLCUQDSZIZ-UHFFFAOYSA-N 0.000 description 1
- YVQBOKCDPCUWSP-UHFFFAOYSA-N oxonane Chemical compound C1CCCCOCCC1 YVQBOKCDPCUWSP-UHFFFAOYSA-N 0.000 description 1
- 229960002085 oxycodone Drugs 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- KJSVAZNPHAQRIM-UHFFFAOYSA-N phenol;prop-1-ene Chemical compound CC=C.OC1=CC=CC=C1 KJSVAZNPHAQRIM-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 159000000008 strontium salts Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/26—General preparatory processes using halocarbonates
-
- 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
- C08G64/18—Block or graft polymers
- C08G64/186—Block or graft polymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
- C08G64/1616—Aliphatic-aromatic or araliphatic polycarbonates saturated containing a chain-terminating or -crosslinking agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
- C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
- C08G64/1666—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/22—General preparatory processes using carbonyl halides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/38—General preparatory processes using other monomers
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
- C08G77/448—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences containing polycarbonate sequences
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/223,037 US6833422B2 (en) | 2002-08-16 | 2002-08-16 | Method of preparing transparent silicone-containing copolycarbonates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200404084A TW200404084A (en) | 2004-03-16 |
| TWI278470B true TWI278470B (en) | 2007-04-11 |
Family
ID=31886637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092122010A TWI278470B (en) | 2002-08-16 | 2003-08-11 | Method of preparing transparent silicone-containing copolycarbonates |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6833422B2 (enExample) |
| EP (1) | EP1543061B1 (enExample) |
| JP (1) | JP5052751B2 (enExample) |
| KR (1) | KR100946844B1 (enExample) |
| CN (1) | CN100383173C (enExample) |
| AT (1) | ATE338081T1 (enExample) |
| AU (1) | AU2003247594A1 (enExample) |
| DE (1) | DE60308041T2 (enExample) |
| TW (1) | TWI278470B (enExample) |
| WO (1) | WO2004016674A1 (enExample) |
Families Citing this family (126)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7169859B2 (en) * | 1999-05-18 | 2007-01-30 | General Electric Company | Weatherable, thermostable polymers having improved flow composition |
| US7605221B2 (en) * | 1999-05-18 | 2009-10-20 | Sabic Innovative Plastics Ip B.V. | Weatherable, thermostable polymers having improved flow composition |
| US7790292B2 (en) | 1999-05-18 | 2010-09-07 | Sabic Innovative Plastics Ip B.V. | Polysiloxane copolymers, thermoplastic composition, and articles formed therefrom |
| US7799855B2 (en) * | 2001-11-12 | 2010-09-21 | Sabic Innovative Plastics Ip B.V. | Flame retardant thermoplastic polycarbonate compositions, use and method thereof |
| US6870013B2 (en) * | 2003-08-08 | 2005-03-22 | General Electric Company | Method for preparation of copolyorganosiloxanecarbonates of high clarity |
| WO2005113638A1 (ja) | 2004-05-20 | 2005-12-01 | Idemitsu Kosan Co., Ltd. | ポリカーボネート樹脂およびこれを用いた電子写真感光体 |
| JP4644442B2 (ja) * | 2004-05-24 | 2011-03-02 | 出光興産株式会社 | 分岐状ポリカーボネート樹脂の製造方法 |
| US7638091B2 (en) * | 2004-07-02 | 2009-12-29 | Sabic Innovative Plastics Ip B. V. | Methods of sterilizing polycarbonate articles and methods of manufacture |
| US20060030647A1 (en) * | 2004-08-05 | 2006-02-09 | Thomas Ebeling | Flame retardant thermoplastic polycarbonate compositions, use, and method of manufacture thereof |
| US7365125B2 (en) * | 2004-08-16 | 2008-04-29 | General Electric Company | Polycarbonate compositions, articles, and method of manufacture |
| US20060142486A1 (en) * | 2004-12-23 | 2006-06-29 | Derudder James L | Thermoplastic polycarbonate compositions, articles made therefrom and method of manufacture |
| US7321014B2 (en) * | 2004-12-29 | 2008-01-22 | General Electric Company | Transparent compositions, methods for the preparation thereof, and articles derived therefrom |
| US7432327B2 (en) * | 2004-12-30 | 2008-10-07 | Sabic Innovative Plastics Ip B.V. | Transparent polymeric compositions comprising polysiloxane-polycarbonate copolymer, articles made therefrom and methods of making same |
| US7498401B2 (en) * | 2005-03-03 | 2009-03-03 | Sabic Innovative Plastics Ip B.V. | Thermoplastic polycarbonate compositions, articles made therefrom and method of manufacture |
| US20070060716A1 (en) * | 2005-09-13 | 2007-03-15 | Bala Ambravaneswaran | Fatigue resistant thermoplastic composition, method of making, and articles formed therefrom |
| US20070093629A1 (en) * | 2005-09-14 | 2007-04-26 | General Electric Company | Siloxane bishchloroformates |
| US7652107B2 (en) * | 2005-10-31 | 2010-01-26 | Sabic Innovative Plastics Ip B.V. | Flame resistant polymer blends |
| US7498388B2 (en) * | 2006-04-10 | 2009-03-03 | Sabic Innovative Plastics Ip B.V. | Polysiloxane-polycarbonate copolymer article |
| US20080081895A1 (en) * | 2006-09-29 | 2008-04-03 | General Electric Company | Polycarbonate-polysiloxane copolymers, method of making, and articles formed therefrom |
| US7524919B2 (en) * | 2006-09-29 | 2009-04-28 | Sabic Innovative Plastics Ip B.V. | Polycarbonate-polysiloxane copolymers, method of making, and articles formed therefrom |
| US7709581B2 (en) * | 2006-09-29 | 2010-05-04 | Sabic Innovative Plastics Ip B.V. | Polycarbonate-polysiloxane copolymer compositions and articles formed therefrom |
| US7888447B2 (en) * | 2007-03-29 | 2011-02-15 | Sabic Innovative Plastics Ip B.V. | Polycarbonate-polysiloxane copolymers, methods for the preparation thereof, and articles derived therefrom |
| US9168696B2 (en) | 2012-06-04 | 2015-10-27 | Sabic Global Technologies B.V. | Marked thermoplastic compositions, methods of making and articles comprising the same, and uses thereof |
| DE102008019503A1 (de) * | 2008-04-18 | 2009-10-22 | Bayer Materialscience Ag | Polycarbonate mit Umlagerungsstrukturen, cyclischen und linearen Oligomeren sowie verbessertem Fließverhalten |
| KR101723699B1 (ko) | 2009-07-29 | 2017-04-05 | 테이진 카세이 가부시키가이샤 | 폴리카보네이트-폴리디오르가노실록산 공중합체 |
| JP5547953B2 (ja) | 2009-12-10 | 2014-07-16 | 出光興産株式会社 | ポリカーボネート−ポリオルガノシロキサン共重合体、その製造方法及び該共重合体を含むポリカーボネート樹脂 |
| US9487646B2 (en) | 2010-08-06 | 2016-11-08 | Nec Corporation | Cellulose resin composition |
| KR101362875B1 (ko) * | 2010-12-30 | 2014-02-14 | 제일모직주식회사 | 폴리카보네이트-폴리실록산 공중합체 및 그의 제조 방법 |
| KR101335290B1 (ko) * | 2010-12-30 | 2013-12-02 | 제일모직주식회사 | 내화학성이 우수한 폴리카보네이트 수지 조성물 |
| JP5684588B2 (ja) * | 2011-01-27 | 2015-03-11 | 帝人株式会社 | ポリカーボネート樹脂組成物および成形品 |
| US8674008B2 (en) | 2011-03-31 | 2014-03-18 | Sabic Innovative Plastics Ip B.V. | Electrical tracking resistance compositions, methods and articles of manufacture |
| US9115283B2 (en) | 2011-03-31 | 2015-08-25 | Sabic Global Technologies B.V. | Heat resistant clear polycarbonate-polysiloxane compounds |
| US8703855B2 (en) | 2011-03-31 | 2014-04-22 | Sabic Innovative Plastics Ip B.V. | Electrical tracking resistance compositions, methods and articles of manufacture |
| US8981015B2 (en) | 2011-03-31 | 2015-03-17 | Sabic Global Technologies B.V. | Flame retardant poly(siloxane) copolymer compositions, methods of manufacture, and articles formed therefrom |
| US9006324B2 (en) | 2011-03-31 | 2015-04-14 | Sabic Global Technologies B.V. | Flame retardant polycarbonate compositions, methods of manufacture, and articles formed therefrom |
| US8703856B2 (en) | 2011-03-31 | 2014-04-22 | Sabic Innovative Plastics Ip B.V. | Electrical tracking resistance compositions, methods and articles of manufacture |
| US9102832B2 (en) | 2011-03-31 | 2015-08-11 | Sabic Global Technologies B.V. | Aircraft component comprising flame retardant compositions and methods of manufacture |
| US8466249B2 (en) | 2011-05-13 | 2013-06-18 | Sabic Innovative Plastics Ip Bv | Clear silicone polycarbonate elastomeric copolymers |
| US8937127B2 (en) | 2011-09-30 | 2015-01-20 | Sabic Global Technologies B.V. | Flame retardant poly(siloxane-etherimide) copolymer compositions, methods of manufacture, and articles formed therefrom |
| IN2014CN02931A (enExample) | 2011-10-18 | 2015-07-03 | Idemitsu Kosan Co | |
| US8993671B2 (en) | 2011-11-24 | 2015-03-31 | Sabic Global Technolgies B.V. | Poly(aliphatic ester)-polycarbonate copolymer/polylactic acid blend |
| US9023922B2 (en) | 2012-05-24 | 2015-05-05 | Sabic Global Technologies B.V. | Flame retardant compositions, articles comprising the same and methods of manufacture thereof |
| US20130317142A1 (en) | 2012-05-24 | 2013-11-28 | Sabic Innovative Plastics Ip B.V. | Flame retardant thermoplastic compositions, methods of manufacture thereof and articles comprising the same |
| US20130313493A1 (en) | 2012-05-24 | 2013-11-28 | Sabic Innovative Plastics Ip B.V. | Flame retardant polycarbonate compositions, methods of manufacture thereof and articles comprising the same |
| US9662833B2 (en) | 2012-06-04 | 2017-05-30 | Sabic Global Technologies B.V. | Marked thermoplastic compositions, methods of making and articles comprising the same, and uses thereof |
| US9303120B2 (en) * | 2012-12-20 | 2016-04-05 | Sabic Global Technologies B.V. | Cross-linked polycarbonate resin with improved chemical and flame resistance |
| US9328240B2 (en) | 2012-12-21 | 2016-05-03 | Sabic Global Technologies B.V. | Polycarbonate compositions, articles formed therefrom, and methods of manufacture thereof |
| US9209443B2 (en) | 2013-01-10 | 2015-12-08 | Sabic Global Technologies B.V. | Laser-perforated porous solid-state films and applications thereof |
| WO2014144438A1 (en) | 2013-03-15 | 2014-09-18 | Sabic Innovative Plastics Ip B.V. | Blends containing photoactive additive |
| US9266541B2 (en) | 2013-05-01 | 2016-02-23 | Sabic Global Technologies B.V. | Interior train components having low smoke and low heat release, and methods of their manufacture |
| US9309407B2 (en) | 2013-05-02 | 2016-04-12 | Sabic Global Technologies B.V. | Polycarbonate-siloxane copolymer flame retarded with a silicone based core shell modifier |
| US20160168334A1 (en) * | 2013-07-24 | 2016-06-16 | Sabic Global Technologies B.V. | Phenolic compounds as end-capping agents for polysiloxanes in polycarbonate-polysiloxane block copolymers |
| US9365720B2 (en) | 2014-01-14 | 2016-06-14 | Sabic Global Technologies B.V. | Interior train components having low smoke and low heat release, and methods of their manufacture |
| US9718956B2 (en) | 2014-01-14 | 2017-08-01 | Sabic Global Technologies B.V. | Interior aircraft components and methods of manufacture |
| JP5878941B2 (ja) * | 2014-02-06 | 2016-03-08 | 出光興産株式会社 | ポリマーの製造方法 |
| CN106232719B (zh) | 2014-04-15 | 2020-05-29 | 沙特基础工业全球技术有限公司 | 高耐热聚碳酸酯组合物 |
| CN106232718A (zh) | 2014-04-15 | 2016-12-14 | 沙特基础工业全球技术有限公司 | 高热聚碳酸酯组合物 |
| CN106255722B (zh) | 2014-04-15 | 2019-04-26 | 沙特基础工业全球技术有限公司 | 高热聚碳酸酯组合物 |
| US20170037243A1 (en) | 2014-04-15 | 2017-02-09 | Sabic Global Technologies B.V. | High heat polycarbonate compositions |
| US20170022359A1 (en) | 2014-04-15 | 2017-01-26 | Sabic Global Technologies B.V. | High heat polycarbonate compositions |
| WO2015160965A1 (en) | 2014-04-15 | 2015-10-22 | Sabic Global Technologies B.V. | High heat polycarbonate compositions |
| KR101837613B1 (ko) * | 2014-05-21 | 2018-03-13 | 주식회사 삼양사 | 투명성 및 내충격성이 향상된 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법 |
| EP3154785A1 (en) | 2014-06-16 | 2017-04-19 | SABIC Global Technologies B.V. | Process for additive manufacturing using thermoplastic materials having selected melt indexes |
| EP3161055B1 (en) | 2014-06-26 | 2021-06-16 | SHPP Global Technologies B.V. | Flame retardant thermally conductive polymer compositions with good flow property and uses thereof |
| WO2016011332A1 (en) | 2014-07-17 | 2016-01-21 | Sabic Global Technologies B.V. | High flow, high heat polycarbonate compositions |
| EP3194472B1 (en) * | 2014-09-18 | 2018-07-11 | Momentive Performance Materials Inc. | Functionalized polyoxyalkylene-siloxane polymers and copolymers made therefrom |
| US10414874B2 (en) * | 2014-10-16 | 2019-09-17 | Sabic Global Technologies B.V. | Polysiloxane-polycarbonate copolymers and method for production thereof |
| US20180282520A1 (en) | 2014-11-25 | 2018-10-04 | Sabic Global Technologies B.V. | Polycarbonate compositions comprising photochromic dyes |
| CN107250275A (zh) | 2015-02-20 | 2017-10-13 | 沙特基础工业全球技术公司 | 具有激光标记功能的浅色导热聚合物组合物 |
| US20180030265A1 (en) | 2015-03-24 | 2018-02-01 | Sabic Global Technologies B.V. | Polysiloxane-polycarbonate copolymer compositions |
| US10196485B2 (en) | 2015-04-07 | 2019-02-05 | Sabic Global Technologies B.V. | Chemical-resistant thermoplastic compositions, articles formed therefrom, and methods of manufacture thereof |
| EP3317325B1 (en) | 2015-06-30 | 2021-06-02 | SHPP Global Technologies B.V. | Thermoplastic composition with balanced chemical resistance and impact properties |
| EP3317352B1 (en) | 2015-06-30 | 2019-04-03 | SABIC Global Technologies B.V. | Compatibilized compositions, articles formed therefrom, and methods of manufacture thereof |
| WO2017051305A1 (en) | 2015-09-21 | 2017-03-30 | Sabic Global Technologies B.V. | Flame retardant polycarbonate composition, a method of making and of using the same |
| US9688855B2 (en) * | 2015-11-17 | 2017-06-27 | Sabic Global Technologies B.V. | Polycarbonate-polysiloxane copolymer compositions for mobile phone housing applications |
| US9598577B1 (en) | 2015-11-17 | 2017-03-21 | Sabic Global Technologies B.V. | Polycarbonate-polysiloxane copolymer compositions, articles formed therefrom, and methods of manufacture thereof |
| US9598578B1 (en) * | 2015-11-17 | 2017-03-21 | SABIC Global Technologies B.V | Polycarbonate-polysiloxane copolymer compositions, articles formed therefrom, and methods of manufacture thereof |
| WO2017149457A1 (en) | 2016-02-29 | 2017-09-08 | Sabic Global Technologies B.V. | Chemically resistant polycarbonate-polyester compositions, methods of manufacture, and articles thereof |
| KR20190008856A (ko) | 2016-05-16 | 2019-01-25 | 사빅 글로벌 테크놀러지스 비.브이. | 열가소성 조성물, 이의 제조 방법 및 이로부터 제조된 물품 |
| CN109415532A (zh) | 2016-06-21 | 2019-03-01 | 沙特基础工业全球技术公司 | 表现出反射性和导热性的聚合物组合物 |
| CN109789632A (zh) | 2016-09-12 | 2019-05-21 | 沙特基础工业全球技术公司 | 用于增材制造工艺的牺牲高热支架材料 |
| ES2889475T3 (es) | 2016-12-19 | 2022-01-12 | Covestro Intellectual Property Gmbh & Co Kg | Producción de copolicarbonatos de bloques que contienen siloxano mediante compatibilizadores |
| US20190330468A1 (en) | 2016-12-30 | 2019-10-31 | Sabic Global Technologies B.V. | High flow, ductile poly(aliphatic ester-carbonate) compositions |
| CN109836565B (zh) * | 2017-11-29 | 2022-01-07 | 万华化学集团股份有限公司 | 一种硅氧烷共聚碳酸酯及其制备方法 |
| US11193025B2 (en) | 2017-12-21 | 2021-12-07 | Shpp Global Technologies B.V. | Thermoplastic composition including passivated chromophore |
| EP3643747A1 (en) | 2018-10-22 | 2020-04-29 | SABIC Global Technologies B.V. | Transparent and flexible blends of pmma and polycarbonate-siloxane copolymer |
| EP3643493A1 (en) | 2018-10-24 | 2020-04-29 | SABIC Global Technologies B.V. | Co-polycarbonate resin materials and materials made therefrom |
| US12180365B2 (en) | 2018-11-14 | 2024-12-31 | Shpp Global Technologies B.V. | Extruded capacitor films with high temperature performance, methods of manufacture, and articles containing the same |
| EP3660075B1 (en) | 2018-11-30 | 2022-06-08 | SHPP Global Technologies B.V. | Endcapped polycarbonates, methods of manufacture, and articles formed therefrom |
| EP3719077B1 (de) | 2019-04-02 | 2022-09-21 | Covestro Deutschland AG | Siloxan-haltige blockcopolycarbonate mit geringer domänengrösse |
| EP3783058A1 (en) | 2019-08-22 | 2021-02-24 | SABIC Global Technologies B.V. | Compositions with improved dielectric strength |
| US20220372280A1 (en) | 2019-09-30 | 2022-11-24 | Shpp Global Technologies B.V. | Flame retardant polycarbonate compositions and thin-wall articles made therefrom |
| EP3808802A1 (en) | 2019-10-14 | 2021-04-21 | SHPP Global Technologies B.V. | Compositions of improved through-plane thermal conductivity using foam injection molding with core-back technology |
| KR102292023B1 (ko) * | 2019-10-30 | 2021-08-24 | 주식회사 삼양사 | 폴리카보네이트 수지 및 그 제조 방법 |
| KR20220117248A (ko) | 2019-12-16 | 2022-08-23 | 에스에이치피피 글로벌 테크놀러지스 비.브이. | 소비자 사용 후 재활용 폴리카보네이트를 포함하는 성형 물품 및 이의 제조 방법 |
| CN114641536B (zh) | 2019-12-16 | 2023-07-18 | 高新特殊工程塑料全球技术有限公司 | 具有改进的熔体体积速率的增强的阻燃聚碳酸酯组合物 |
| EP3845587A1 (en) | 2019-12-31 | 2021-07-07 | SHPP Global Technologies B.V. | Microwave absorbing materials and molded articles for automotive radar sensor applications |
| EP3868820A1 (en) | 2020-02-20 | 2021-08-25 | SHPP Global Technologies B.V. | Articles and structures with laser breakable and platable compounds |
| CN116057111A (zh) | 2020-07-30 | 2023-05-02 | 高新特殊工程塑料全球技术有限公司 | 含玻璃的阻燃聚碳酸酯组合物 |
| US20240010832A1 (en) | 2020-12-15 | 2024-01-11 | Shpp Global Technologies B.V. | Fire retardant polycarbonate compositions for transparent thin-wall applications |
| EP4015579B1 (en) | 2020-12-16 | 2025-01-29 | SHPP Global Technologies B.V. | Polycarbonate copolymer formulation with improved heat, excellent impact and flame retardant performance |
| EP4036170A1 (en) | 2021-01-29 | 2022-08-03 | SHPP Global Technologies B.V. | Moldable composition and molded articles made therefrom |
| US20240150573A1 (en) | 2021-02-26 | 2024-05-09 | Shpp Global Technologies B.V. | Polycarbonate compositions |
| EP4056603B1 (en) | 2021-03-08 | 2025-12-03 | SHPP Global Technologies B.V. | Composition of methacrylate (co)polymer and poly(carbonate-siloxane) blockcopolymer and its use in scratch and impact resitant articles |
| CN116848192A (zh) | 2021-03-12 | 2023-10-03 | 高新特殊工程塑料全球技术有限公司 | 热塑性组合物 |
| WO2022238960A1 (en) | 2021-05-13 | 2022-11-17 | Shpp Global Technologies B.V. | Thermoplastic compositions and uses thereof |
| EP4101893B1 (en) | 2021-06-08 | 2025-07-09 | SHPP Global Technologies B.V. | Thermoplastic compositions and shaped articles thereof |
| CN117999309A (zh) | 2021-09-27 | 2024-05-07 | 高新特殊工程塑料全球技术有限公司 | 膜挤出组合物和相关的挤出膜、金属化膜和电容器 |
| US20250051563A1 (en) | 2021-12-07 | 2025-02-13 | Shpp Global Technologies B.V. | Polycarbonate compositions |
| WO2023166427A1 (en) | 2022-03-01 | 2023-09-07 | Shpp Global Technologies B.V. | Transparent polycarbonate compositions |
| EP4499751A1 (en) | 2022-03-24 | 2025-02-05 | SHPP Global Technologies B.V. | Composition, method for the manufacture thereof, and article comprising the composition |
| CN119213058A (zh) | 2022-05-17 | 2024-12-27 | 科思创德国股份有限公司 | 由特殊封端的硅氧烷嵌段制成的聚硅氧烷-聚碳酸酯-嵌段共缩合物 |
| CN119301199A (zh) | 2022-05-25 | 2025-01-10 | 高新特殊工程塑料全球技术有限公司 | 抗滴落聚碳酸酯组合物 |
| US20250320358A1 (en) | 2022-05-25 | 2025-10-16 | Shpp Global Technologies B.V. | Anti-drip polycarbonate compositions |
| EP4282919B1 (en) | 2022-05-25 | 2025-04-16 | SHPP Global Technologies B.V. | Transparent flame retardant ductile compositions and thin-wall articles thereof |
| EP4547736A1 (en) | 2022-06-30 | 2025-05-07 | SHPP Global Technologies B.V. | Chemically resistant ultrasonically weldable parts and ultrasonically welded articles thereof |
| CN115612108B (zh) * | 2022-10-11 | 2023-10-31 | 沧州大化股份有限公司 | 一种聚硅氧烷共聚聚碳酸酯的连续化生产工艺及其生产装置 |
| EP4619474A1 (en) | 2022-11-16 | 2025-09-24 | SHPP Global Technologies B.V. | Chemically resistant polycarbonate compositions and articles made therefrom |
| WO2024252358A1 (en) | 2023-06-07 | 2024-12-12 | Shpp Global Technologies B.V. | Glass-filled flame retardant polycarbonate compositions |
| WO2024252357A1 (en) | 2023-06-07 | 2024-12-12 | Shpp Global Technologies B.V. | Flame retardant polycarbonate compositions |
| WO2025074279A1 (en) | 2023-10-06 | 2025-04-10 | Shpp Global Technologies B.V. | Anti-scratch compositions and articles comprising the same |
| WO2025074278A1 (en) | 2023-10-06 | 2025-04-10 | Shpp Global Technologies B.V. | Anti-scratch compositions and articles comprising the same |
| EP4578914A1 (en) | 2023-12-26 | 2025-07-02 | SHPP Global Technologies B.V. | Flame retardant polycarbonate compositions |
| WO2025158329A1 (en) | 2024-01-24 | 2025-07-31 | Shpp Global Technologies B.V. | Copolycarbonates and compositions thereof with high refractive index and low birefringence |
| WO2025177115A1 (en) | 2024-02-23 | 2025-08-28 | Shpp Global Technologies B.V. | Flame retardant polycarbonate compositions |
| EP4656674A1 (en) | 2024-05-31 | 2025-12-03 | SHPP Global Technologies B.V. | Extruded films with high temperature performance, and articles containing the same |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991000885A1 (fr) | 1989-07-07 | 1991-01-24 | Idemitsu Petrochemical Co., Ltd. | Copolymere de polycarbonate-polydimethylsiloxane et son procede de production |
| US5214118A (en) * | 1990-10-05 | 1993-05-25 | General Electric Company | Process for synthesis of polyestercarbonate-siloxane copolymers |
| EP0500131B1 (en) | 1991-02-22 | 2001-01-10 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin solution for film formation by casting |
| EP0633292B1 (en) * | 1993-07-09 | 1998-12-30 | General Electric Company | Compositions of siloxane polyestercarbonate block terpolymers and high heat polycarbonates |
| US5616674A (en) | 1994-05-10 | 1997-04-01 | General Electric Company | Method of preparing polycarbonate-polysiloxane block copolymers |
| US5530083A (en) | 1994-07-21 | 1996-06-25 | General Electric Company | Silicone-polycarbonate block copolymers and polycarbonate blends having reduced haze, and method for making |
| JPH09265663A (ja) | 1996-03-28 | 1997-10-07 | Idemitsu Petrochem Co Ltd | デジタルビデオディスク基板 |
| US6103855A (en) | 1999-03-30 | 2000-08-15 | General Electric Company | Batch process for the production of polycarbonate by interfacial polymerization |
| US6392079B1 (en) | 1999-03-30 | 2002-05-21 | General Electric Company | Method and apparatus for preparing monofunctional aromatic chloroformates suitable for use as chainstopping agents |
| US6268461B1 (en) | 1999-11-02 | 2001-07-31 | General Electric Company | Method for preparing hydroxyaromatic chloroformates |
| US6492481B1 (en) * | 2000-07-10 | 2002-12-10 | General Electric Company | Substantially single phase silicone copolycarbonates, methods, and optical articles made therefrom |
| US6630525B2 (en) * | 2001-10-09 | 2003-10-07 | General Electric Company | Polycarbonate-siloxane copolymers |
-
2002
- 2002-08-16 US US10/223,037 patent/US6833422B2/en not_active Expired - Lifetime
-
2003
- 2003-06-17 JP JP2004529081A patent/JP5052751B2/ja not_active Expired - Fee Related
- 2003-06-17 WO PCT/US2003/019596 patent/WO2004016674A1/en not_active Ceased
- 2003-06-17 KR KR1020057002665A patent/KR100946844B1/ko not_active Expired - Lifetime
- 2003-06-17 CN CNB038238705A patent/CN100383173C/zh not_active Expired - Fee Related
- 2003-06-17 EP EP03788237A patent/EP1543061B1/en not_active Expired - Lifetime
- 2003-06-17 AU AU2003247594A patent/AU2003247594A1/en not_active Abandoned
- 2003-06-17 AT AT03788237T patent/ATE338081T1/de not_active IP Right Cessation
- 2003-06-17 DE DE60308041T patent/DE60308041T2/de not_active Expired - Lifetime
- 2003-08-11 TW TW092122010A patent/TWI278470B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050048609A (ko) | 2005-05-24 |
| TW200404084A (en) | 2004-03-16 |
| JP5052751B2 (ja) | 2012-10-17 |
| EP1543061A1 (en) | 2005-06-22 |
| CN1688630A (zh) | 2005-10-26 |
| WO2004016674A1 (en) | 2004-02-26 |
| DE60308041D1 (de) | 2006-10-12 |
| DE60308041T2 (de) | 2007-04-05 |
| US6833422B2 (en) | 2004-12-21 |
| AU2003247594A1 (en) | 2004-03-03 |
| ATE338081T1 (de) | 2006-09-15 |
| US20040039145A1 (en) | 2004-02-26 |
| JP2005535761A (ja) | 2005-11-24 |
| KR100946844B1 (ko) | 2010-03-09 |
| CN100383173C (zh) | 2008-04-23 |
| EP1543061B1 (en) | 2006-08-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI278470B (en) | Method of preparing transparent silicone-containing copolycarbonates | |
| EP2712880A1 (en) | Polycarbonate copolymer having high fluidity, method for producing aromatic polycarbonate resin having high molecular weight, and aromatic polycarbonate compound | |
| KR101109925B1 (ko) | 고투명도 코폴리오가노실록세인카보네이트의 제조방법 | |
| KR100979584B1 (ko) | 폴리카보네이트의 제조방법 | |
| CN102822241A (zh) | 羟基-封端的硅氧烷,聚硅氧烷-聚碳酸酯共聚物,及其制备方法 | |
| TW200307704A (en) | Method of preparing polyestercarbonates | |
| JPH0149730B2 (enExample) | ||
| JP2005517782A (ja) | ポリ（カーボネート−コ−エステル）コポリマーの製造方法 | |
| CN111560117B (zh) | 一种硅氧烷共聚碳酸酯的制备方法 | |
| JP2556517B2 (ja) | スピロビインダンビスフェノ−ル類からの環状ポリカ−ボネ−トオリゴマ− | |
| CA1127795A (en) | Method for manufacture of aromatic polyester-polycarbonate | |
| TW200932782A (en) | Copolymers comprising a trimethylene carbonate and poly (trimethylene ether) glycols | |
| CN109836565B (zh) | 一种硅氧烷共聚碳酸酯及其制备方法 | |
| JP3047955B2 (ja) | 難燃性ポリカーボネートの製造方法 | |
| JPH0747628B2 (ja) | オリゴマー性のカーボネート連鎖停止剤 | |
| JP2011032433A (ja) | ポリカーボネート−ポリジオルガノシロキサン共重合体の製造方法 | |
| CN116096781A (zh) | 聚碳酸酯及其制备方法 | |
| JP2005511811A (ja) | ポリカーボネート樹脂の末端封鎖法及び当該方法に用いられる組成物 | |
| JPH06329786A (ja) | 芳香族ポリカーボネートの製造方法 | |
| JP3395436B2 (ja) | 芳香族ポリカーボネートの製造方法 | |
| US4921975A (en) | Cyclic monocarbonate bishaloformates | |
| TWI675863B (zh) | 分枝聚碳酸酯之製造方法 | |
| WO2009020967A1 (en) | Activated esters for synthesis of sulfonated telechelic polycarbonates | |
| JP2012509958A (ja) | 耐衝撃性が向上した線状ポリカーボネートの製造方法 | |
| JP5480514B2 (ja) | 高分子量ハロゲン化ポリカーボネート化合物およびその製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Expiration of patent term of an invention patent |