CN107849254A - 新型聚有机硅氧烷和使用该聚有机硅氧烷制备的共聚碳酸酯 - Google Patents
新型聚有机硅氧烷和使用该聚有机硅氧烷制备的共聚碳酸酯 Download PDFInfo
- Publication number
- CN107849254A CN107849254A CN201680043792.8A CN201680043792A CN107849254A CN 107849254 A CN107849254 A CN 107849254A CN 201680043792 A CN201680043792 A CN 201680043792A CN 107849254 A CN107849254 A CN 107849254A
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- China
- Prior art keywords
- polysiloxane
- chemical formula
- copolycarbonate
- hydrogen
- alkyl
- 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.)
- Granted
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- -1 polysiloxane Polymers 0.000 title claims abstract description 61
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 38
- 239000000126 substance Substances 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 230000000704 physical effect Effects 0.000 abstract description 6
- 239000004431 polycarbonate resin Substances 0.000 abstract description 3
- 229920005668 polycarbonate resin Polymers 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 13
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- 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 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229920005573 silicon-containing polymer Polymers 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZKGRRJAULWNS-UHFFFAOYSA-N Chavicol Natural products OC1=CC=C(CCC=C)C=C1 IAZKGRRJAULWNS-UHFFFAOYSA-N 0.000 description 2
- 238000005618 Fries rearrangement reaction Methods 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- 239000004425 Makrolon Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004035 construction material Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 230000000774 hypoallergenic effect Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- RGIBXDHONMXTLI-UHFFFAOYSA-N p-allylphenol Natural products OC1=CC=C(CC=C)C=C1 RGIBXDHONMXTLI-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- FDIPWBUDOCPIMH-UHFFFAOYSA-N 2-decylphenol Chemical compound CCCCCCCCCCC1=CC=CC=C1O FDIPWBUDOCPIMH-UHFFFAOYSA-N 0.000 description 1
- IEMXKEMFCFILAA-UHFFFAOYSA-N 2-docosylphenol Chemical compound CCCCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O IEMXKEMFCFILAA-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 1
- QEMHBAGGYKJNSS-UHFFFAOYSA-N 2-icosylphenol Chemical compound CCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O QEMHBAGGYKJNSS-UHFFFAOYSA-N 0.000 description 1
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 description 1
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 description 1
- OREKREJVUNVFJP-UHFFFAOYSA-N 2-triacontylphenol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O OREKREJVUNVFJP-UHFFFAOYSA-N 0.000 description 1
- FVKYHUBHBRJSDA-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol propane Chemical compound OC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)O.CCC FVKYHUBHBRJSDA-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive 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
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- ZQUZPFYNEARCQO-UHFFFAOYSA-N dinaphthalen-1-yl carbonate Chemical compound C1=CC=C2C(OC(OC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 ZQUZPFYNEARCQO-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 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
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000003717 m-cresyl group Chemical group [H]C1=C([H])C(O*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 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 description 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 125000005401 siloxanyl group Chemical group 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 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
- C08G64/18—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
- C08G64/04—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
- C08G64/085—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing silicon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si 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
- 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
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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Abstract
本发明提供一种能够制备具有改善的耐候性和流动性,同时保持聚碳酸酯树脂的固有物理性能的共聚碳酸酯的新型聚有机硅氧烷,以及使用该聚有机硅氧烷制备的共聚碳酸酯。
Description
技术领域
相关申请的交叉引用
本申请要求于2015年9月4日提交到韩国知识产权局的韩国专利申请No.10-2015-0125677的权益,该申请的公开内容通过引用全部并入本申请中。
本发明涉及一种能够制备具有改善的耐候性和流动性的共聚碳酸酯的新型聚有机硅氧烷,以及使用该聚有机硅氧烷制备的共聚碳酸酯。
背景技术
聚有机硅氧烷作为一种聚硅氧烷,是指具有被有机基团取代的硅氧烷键作为主链的聚合物。例如,聚有机硅氧烷由芳香族二醇如双酚A与碳酸酯前体如光气的缩合聚合制备,其无色、无味、耐氧化,是在室温下稳定的低变应原性(hypoallergenic)绝缘体,并且用于电气、电子、车辆、机械、药品、化妆品、润滑剂、粘合剂、垫圈、整形手术用人造辅助设备等中。
另外,聚有机硅氧烷具有优异的冲击强度、尺寸稳定性、耐热性、透明度等,并且应用于诸如电子电气产品的外部材料、车辆零部件、建筑材料、光学元件等的多种领域中。近来,已经进行许多研究以将共聚碳酸酯树脂应用于更多领域中,其中,通过使两种以上具有不同结构的芳香族二醇共聚合来在聚碳酸酯的主链中引入具有不同结构的单体,从而得到所期望的性能。
特别地,也在进行将聚硅氧烷结构引入聚碳酸酯的主链中的研究。然而,大多数技术具有生产成本高并且不能同时改善耐化学性和冲击强度的缺点。
然而,随着共聚碳酸酯的应用领域的扩大,要求共聚碳酸酯具有更高的耐候性和流动性,因此,需要一种新型结构的共聚碳酸酯,其能够改善耐候性和流动性,同时保持其固有物理性能。
发明内容
技术问题
本发明提供一种能够制备具有改善的耐候性和流动性的共聚碳酸酯的新型聚有机硅氧烷。
此外,本发明提供一种使用所述聚有机硅氧烷制备的共聚碳酸酯。
此外,本发明提供一种使用所述共聚碳酸酯制造的模制品。
技术方案
本发明提供一种由下面的化学式1表示的聚有机硅氧烷。
此外,本发明提供一种共聚碳酸酯,该共聚碳酸酯的重均分子量为1,000g/mol至100,000g/mol,并且包含由下面的化学式2表示的重复单元和由下面的化学式3表示的重复单元。
此外,本发明提供一种使用所述共聚碳酸酯制造的模制品。
下文中,将更详细地描述根据本发明的具体实施方案的聚有机硅氧烷、共聚碳酸酯和模制品。
根据本发明的一个实施方案,提供一种由下面的化学式1表示的聚有机硅氧烷:
[化学式1]
B-A-B
其中,A是
B是
R1至R4各自独立地是氢或C1-10烷基,
R5是氢、卤素、羟基、C1-10烷基、C1-10烷氧基或C6-10芳基,
R6至R9各自独立地是氢、C1-10烷基或卤素,
X是-CO-或-CO-(C6-10亚芳基)-CO-,
Y是C1-10亚烷基,
Z是键、-OCO-或-COO-,
W是含有-(C1-10亚烷基)-O-的二价官能团,
n是1至99的整数。
聚有机硅氧烷作为一种聚硅氧烷,是指具有被有机基团取代的硅氧烷键作为主链的聚合物。在聚有机硅氧烷中,特别地,一个实施方案的由化学式1表示的聚有机硅氧烷可以表现出由于硅氧烷单体而具有的效果以及由于由化学式1的A表示的连接体和酯结构而具有的效果两者。因此,所述聚有机硅氧烷的特征在于,由于弗里斯重排(Friesrearrangement)效应而具有改善的耐候性,由于酯结构和醚结构的内部链移动性的改善而具有改善的流动性,同时保持高延展性。
另外,化学式1中的W优选地是含有-(C1-10亚烷基)-COO-(C1-10亚烷基)-O-的二价官能团。
此外,A更优选地是
此外,在化学式1中,R1至R4优选地各自独立地是氢或C1-4烷基。
此外,R5优选地是氢或C1-4烷氧基。
此外,R6至R9优选地各自独立地是氢或C1-4烷基。
此外,X优选地是-CO-(亚苯基)-CO-。
此外,Y优选地是C1-5亚烷基。
另外,由化学式1表示的聚有机硅氧烷的具体实例可以是下面的化合物:
其中,A是
同时,一个实施方案的聚有机硅氧烷可以通过下面的反应图解1中的方法来合成,但是不限于此,由化学式1表示的化合物的制备方法将在下面描述的实施例中更详细地描述:
[反应图解1]
其中,R1至R5、X、Y、Z和n与在化学式1中定义的相同,R14是羟基或卤素,优选地是羟基或氯。
步骤1是通过使由化学式1-2表示的化合物与作为碳酸酯类化合物的由化学式1-3表示的化合物反应来制备由化学式1-4表示的化合物的步骤。在这方面,由化学式1-2表示的化合物与由化学式1-3表示的化合物的摩尔比优选地为1:1.1至1:5,更优选地为1:1.3至1:2.5,在所述反应中,优选使用氯仿作为溶剂。此外,所述反应优选地在室温下进行。
步骤2是通过使由化学式1-4表示的化合物与作为聚有机硅氧烷化合物的由化学式1-5表示的化合物反应来制备由化学式1表示的化合物的步骤。由化学式1-4表示的化合物与由化学式1-5表示的化合物的摩尔比优选地为1:1.1至1:5,更优选地为1:1.3至1:2.5,在所述反应中,优选使用氯仿作为溶剂。此外,所述反应优选地在室温下进行。
根据本发明的另一实施方案,提供一种共聚碳酸酯,其重均分子量为1,000g/mol至100,000g/mol,并且包含由下面的化学式2表示的重复单元和由下面的化学式3表示的重复单元:
[化学式2]
其中,A是
R1至R4各自独立地是氢或C1-10烷基,
R5是氢、卤素、羟基、C1-10烷基、C1-10烷氧基或C6-10芳基,
R6至R9各自独立地是氢、C1-10烷基或卤素,
X是-CO-或-CO-(C6-10亚芳基)-CO-,
Y是C1-10亚烷基,
Z是键、-OCO-或-COO-,
W是含有-(C1-10亚烷基)-O-的二价官能团,
n是1至99的整数,
[化学式3]
其中,X1是未被取代的或被苯基取代的C1-10亚烷基、C3-6亚环烷基、O、S、SO、SO2或CO,
R10至R13各自独立地是氢、C1-10烷基或卤素。
在化学式2中,A、R1至R9、X、Y、Z和n与在化学式1中描述的相同,而没有限制。
X1优选地是未被取代的或被苯基取代的C1-4亚烷基、C3-6亚环烷基、O、S、SO、SO2或CO。
此外,R10至R13优选地各自独立地是氢、C1-4烷基、氯或溴。
一个实施方案的共聚碳酸酯可以通过使由化学式1表示的聚有机硅氧烷、芳香族二醇化合物和碳酸酯前体聚合来制备,并且如上所述,所述共聚碳酸酯的特征在于,由于由化学式1表示的聚有机硅氧烷中的酯或醚结构引起内部移动性的改善,因此,具有改善的耐候性和流动性,同时保持共聚碳酸酯的延展性。
芳香族二醇化合物是由下面的化学式4表示的化合物,并且对应于化学式3:
[化学式4]
其中,X1和R10至R13与在化学式3中定义的相同。
芳香族二醇化合物的具体实例可以包括:双(4-羟苯基)甲烷、双(4-羟苯基)醚、双(4-羟苯基)砜、双(4-羟苯基)亚砜、双(4-羟苯基)硫化物、双(4-羟苯基)酮、1,1-双(4-羟苯基)乙烷、2,2-双(4-羟苯基)丙烷(双酚A)、2,2-双(4-羟苯基)丁烷、1,1-双(4-羟苯基)环己烷(双酚Z)、2,2-双(4-羟基-3,5-二溴苯基)丙烷、2,2-双(4-羟基-3,5-二氯苯基)丙烷、2,2-双(4-羟基-3-溴苯基)丙烷、2,2-双(4-羟基-3-氯苯基)丙烷、2,2-双(4-羟基-3-甲基苯基)丙烷、2,2-双(4-羟基-3,5-二甲基苯基)丙烷或1,1-双(4-羟苯基)-1-苯基乙烷。
碳酸酯前体用于连接由化学式1表示的化合物与由化学式4表示的化合物,其具体实例可以包括:光气、三光气、双光气、溴光气、碳酸二甲酯、碳酸二乙酯、碳酸二丁酯、碳酸二环己酯、碳酸二苯酯、碳酸二甲苯酯、碳酸双(氯苯基)酯、碳酸间甲苯酯、碳酸二萘酯、碳酸双(联苯)酯或双卤代甲酸酯(bishaloformate)。
另外,一个实施方案的共聚碳酸酯可以通过包括使包含由化学式1表示的聚有机硅氧烷、芳香族二醇化合物和碳酸酯前体的组合物聚合的步骤来制备。
在聚合时,基于100重量%的组合物,由化学式1表示的聚有机硅氧烷的用量可以为0.1重量%以上、1重量%以上或3重量%以上,且为20重量%以下、10重量%以下或7重量%以下。
此外,基于100重量%的组合物,芳香族二醇化合物的用量可以为40重量%以上、50重量%以上或55重量%以上,且为80重量%以下、70重量%以下或65重量%。
此外,基于100重量%的组合物,碳酸酯前体的用量可以为10重量%以上、20重量%以上或30重量%,且为60重量%以下、50重量%以下或40重量%以下。
在这方面,聚合可以优选地通过界面聚合进行。在界面聚合过程中,聚合反应可以在常压和低温下进行,并且容易控制分子量。
聚合温度优选地为0℃至40℃,反应时间优选地为10分钟至5小时。此外,在反应过程中,pH优选地保持在9以上或11以上。
对在聚合中可以使用的溶剂没有特别地限制,只要是本领域中通常用于共聚碳酸酯的聚合的溶剂即可,例如,诸如二氯甲烷、氯苯等的卤代烃。
此外,聚合优选地在酸粘合剂的存在下进行,并且酸粘合剂可以是诸如氢氧化钠、氢氧化钾等的碱金属氢氧化物,或者是诸如吡啶等的胺化合物。
另外,为了在聚合过程中控制共聚碳酸酯的分子量,聚合优选地在分子量调节剂的存在下进行。作为分子量调节剂,可以使用C1-20烷基酚。其具体实例可以包括:对叔丁基苯酚、对枯基苯酚、癸基苯酚、十二烷基苯酚、十四烷基苯酚、十六烷基苯酚、十八烷基苯酚、二十烷基苯酚、二十二烷基苯酚或三十烷基苯酚。分子量调节剂可以在聚合引发之前、聚合引发的过程中或聚合引发之后加入。基于100重量份的芳香族二醇化合物,分子量调节剂的含量可以为,例如,0.01重量份以上、0.1重量份以上或1重量份以上,且为10重量份以下、6重量份以下或5重量份以下。在所述范围内,可以得到所期望的分子量。
为了促进聚合反应,还可以使用反应促进剂,例如,诸如三乙胺、四正丁基溴化铵、四正丁基溴化鏻等的叔胺化合物、季铵化合物、季鏻化合物。
另外,本发明提供一种使用所述共聚碳酸酯制造的模制品。如上所述,由于衍生自化学式1表示的聚有机硅氧烷中的聚丙二醇的结构,流动性得到改善,同时保持了共聚碳酸酯的延展性,因此,与使用先前的共聚碳酸酯制造的模制品相比,所述模制品可以应用于多种领域。
除了根据本发明的共聚碳酸酯之外,根据需要,所述模制品还可以包含选自抗氧化剂、增塑剂、抗静电剂、成核剂、阻燃剂、润滑剂、冲击改性剂、荧光增白剂、紫外线吸收剂、颜料和染料中的一种或多种。
所述模制品的制造方法可以包括,例如,以下步骤:利用混合器将本发明的共聚碳酸酯和其它添加剂混合,用挤出机将混合物挤出成型来制备颗粒,干燥颗粒,然后用注塑机注射干燥后的颗粒。
有益效果
根据本发明的新型聚有机硅氧烷可以用作共聚碳酸酯的单体,并且可以具有改善的耐候性和流动性,同时保持了共聚碳酸酯的固有物理性能如延展性。
具体实施方式
将参照下面的实施例更详细地描述本发明。然而,下面的实施例仅用于说明的目的,并且本发明的公开内容不意在被下面的实施例所限制。
实施例1:
(步骤1)聚有机硅氧烷的制备
向2,000mL的三颈回流烧瓶中添加1,000mL(液态)的氯仿(CHCl3),在氮气气氛下,在室温下经1小时缓慢地溶解11.7g的Antioxidant-245(亚乙基双(氧亚乙基)双[3-(5-叔丁基-4-羟基-间甲苯基)丙酸酯],Mw:586g/mol)和7.1g的对苯二甲酰氯。然后,加入25g的三乙胺并使其反应1小时,加入210g的烯丙基苯酚聚二甲基硅氧烷(n:43,Mw:3,500g/mol)并充分反应来制备由上面的化学式表示的化合物,其1H NMR图示于图1中。
(步骤2)共聚碳酸酯树脂的制备
向聚合反应器中添加232g的双酚A、1,784g的蒸馏水和385g的氢氧化钠,并在氮气气氛下混合以完全溶解双酚A。然后,加入875g的二氯甲烷、4.3g的PTBP(对叔丁基苯酚)和7.0g(基于固体为5.2重量%的聚碳酸酯树脂)的在步骤1中制备的化合物并混合。向其中经1小时逐滴添加130g的溶解在920g二氯甲烷中的TPG(三光气),此时,使用氢氧化钠水溶液将pH保持为11。逐滴添加结束之后,将溶液老化15分钟,并向其中加入溶解有46g三乙胺的二氯甲烷。在总反应时间1小时30分钟之后,将pH降低至4,并使用蒸馏水进行三次洗涤来分离二氯甲烷相。将由此得到的聚合物在甲醇中沉淀,并在120℃下干燥,得到最终的粉末状共聚碳酸酯树脂。其1H NMR图示于图2中。
实施例2
除了使用120g的烯丙基苯酚聚二甲基硅氧烷(n:22,Mw:2,000g/mol)代替烯丙基苯酚聚二甲基硅氧烷(n:43,Mw:3,500g/mol)之外,以与实施例1中相同的方式制备共聚碳酸酯树脂。
实施例3
除了在步骤2中使用3.5g(基于固体为2.6重量%的聚碳酸酯树脂)而不是7.0g的在步骤1中制备的化合物之外,以与实施例1中相同的方式制备共聚碳酸酯树脂。
比较例1
除了在步骤2中不使用在步骤1中制备的化合物之外,以与实施例1中相同的方式制备共聚碳酸酯树脂。
试验例:共聚碳酸酯树脂的物理性能的评价
将在实施例1至3和比较例1中得到的共聚碳酸酯树脂颗粒化来制备用于评价物理性能的样品,并通过下面的方法测定样品的物理性能。结果示于下面的表1中。
(1)流动性(MFR,g/10分钟):根据标准ASTM D1238(300℃和1.2kg的条件下)使用样品测定。
(2)室温冲击强度和低温冲击强度(缺口悬臂梁式,J/m):根据ASTM D256(1/8英寸,缺口悬臂梁式)在23℃和-30℃下分别测定。
(3)耐候性(ΔYI,500小时):根据ASTM D4329,使用QUV-A加速老化试验机(Q-LAB)经500小时测量样品的黄度指数差(ΔYI)。
(4)重均分子量(Mw,g/mol):使用Agilent 12000系列GPC,通过用PC标准品进行称量来测定。
[表1]
如表1中所示,可以发现,与比较例1相比,在实施例中制备的共聚碳酸酯树脂具有相同或更高的流动性和室温冲击强度,同时具有非常优异的在-30℃下的低温冲击强度和耐候性。
实施例的共聚碳酸酯树脂具有优异的低温冲击强度以及经受各种天气时保持聚碳酸酯树脂的固有物理性能的耐候性,从而容易应用于各种领域,如电子电气产品的外部材料、车辆零部件和建筑材料。
Claims (12)
1.一种聚有机硅氧烷,该聚有机硅氧烷由下面的化学式1表示:
[化学式1]
B-A-B
其中,A是
B是
R1至R4各自独立地是氢或C1-10烷基,
R5是氢、卤素、羟基、C1-10烷基、C1-10烷氧基或C6-10芳基,
R6至R9各自独立地是氢、C1-10烷基或卤素,
X是-CO-或-CO-(C6-10亚芳基)-CO-,
Y是C1-10亚烷基,
Z是键、-OCO-或-COO-,
W是包含-(C1-10亚烷基)-O-的二价官能团,
n是1至99的整数。
2.根据权利要求1所述的聚有机硅氧烷,其中,W是包含-(C1-10亚烷基)-COO-(C1-10亚烷基)-O-的二价官能团。
3.根据权利要求1所述的聚有机硅氧烷,其中,A是
4.根据权利要求1所述的聚有机硅氧烷,其中,R1至R4各自独立地是氢或C1-4烷基。
5.根据权利要求1所述的聚有机硅氧烷,其中,R5是氢或C1-4烷氧基。
6.根据权利要求1所述的聚有机硅氧烷,其中,X是-CO-(亚苯基)-CO-。
7.根据权利要求1所述的聚有机硅氧烷,其中,Y是C1-5亚烷基。
8.根据权利要求1所述的聚有机硅氧烷,其中,所述聚有机硅氧烷具有下面的结构:
其中,A是
9.一种共聚碳酸酯,其重均分子量为1,000g/mol至100,000g/mol,并且包含由下面的化学式2表示的重复单元和由下面的化学式3表示的重复单元:
[化学式2]
其中,A是
R1至R4各自独立地是氢或C1-10烷基,
R5是氢、卤素、羟基、C1-10烷基、C1-10烷氧基或C6-10芳基,
R6至R9各自独立地是氢、C1-10烷基或卤素,
X是-CO-或-CO-(C6-10亚芳基)-CO-,
Y是C1-10亚烷基,
Z是键、-OCO-或-COO-,
W是包含-(C1-10亚烷基)-O-的二价官能团,
n是1至99的整数,
[化学式3]
其中,X1是未被取代的或被苯基取代的C1-10亚烷基、C3-6亚环烷基、O、S、SO、SO2或CO,
R10至R13各自独立地是氢、C1-10烷基或卤素。
10.根据权利要求9所述的共聚碳酸酯,其中,X1是未被取代的或被苯基取代的C1-4亚烷基、C3-6亚环烷基、O、S、SO、SO2或CO。
11.根据权利要求9所述的共聚碳酸酯,其中,R10至R13各自独立地是氢、C1-4烷基、氯或溴。
12.一种模制品,其使用权利要求9至11中任意一项所述的共聚碳酸酯制造。
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