WO2022038883A1 - ポリカーボネート－ポリシロキサン樹脂 - Google Patents
ポリカーボネート－ポリシロキサン樹脂 Download PDFInfo
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- WO2022038883A1 WO2022038883A1 PCT/JP2021/023099 JP2021023099W WO2022038883A1 WO 2022038883 A1 WO2022038883 A1 WO 2022038883A1 JP 2021023099 W JP2021023099 W JP 2021023099W WO 2022038883 A1 WO2022038883 A1 WO 2022038883A1
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- Prior art keywords
- group
- carbon atoms
- polycarbonate
- polysiloxane
- polysiloxane resin
- Prior art date
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- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 162
- 229920005989 resin Polymers 0.000 title claims abstract description 143
- 239000011347 resin Substances 0.000 title claims abstract description 143
- -1 polysiloxane Polymers 0.000 claims abstract description 105
- 230000009477 glass transition Effects 0.000 claims abstract description 27
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 26
- 239000004417 polycarbonate Substances 0.000 claims abstract description 26
- 230000005484 gravity Effects 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 122
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 238000000465 moulding Methods 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 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 description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 238000002834 transmittance Methods 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 7
- 125000003172 aldehyde group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- XEWPEIOKCHAXBH-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexyl]-2-methylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C)C(O)=CC=1)C1=CC=C(O)C(C)=C1 XEWPEIOKCHAXBH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 claims description 3
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 description 45
- 238000000034 method Methods 0.000 description 34
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 32
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical class CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000004205 dimethyl polysiloxane Substances 0.000 description 15
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 15
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 15
- 229920005668 polycarbonate resin Polymers 0.000 description 13
- 239000004431 polycarbonate resin Substances 0.000 description 13
- HSQWCQQAYCHINS-UHFFFAOYSA-N BPC Chemical compound BPC HSQWCQQAYCHINS-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003063 flame retardant Substances 0.000 description 11
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 11
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000001746 injection moulding Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 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 description 5
- 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 description 5
- 239000010408 film Substances 0.000 description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000006085 branching agent Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000005027 hydroxyaryl group Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000004381 surface treatment Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 238000012696 Interfacial polycondensation Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 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 3
- 239000001294 propane Substances 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- SICLLPHPVFCNTJ-UHFFFAOYSA-N 1,1,1',1'-tetramethyl-3,3'-spirobi[2h-indene]-5,5'-diol Chemical compound C12=CC(O)=CC=C2C(C)(C)CC11C2=CC(O)=CC=C2C(C)(C)C1 SICLLPHPVFCNTJ-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- CUAWUNQAIYJWQT-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxy-3,5-dimethylphenyl)ethyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C=2C=C(C)C(O)=C(C)C=2)C=2C=C(C)C(O)=C(C)C=2)=C1 CUAWUNQAIYJWQT-UHFFFAOYSA-N 0.000 description 2
- ICYDRUIZSPKQOH-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)decyl]phenol Chemical compound C=1C=C(O)C=CC=1C(CCCCCCCCC)C1=CC=C(O)C=C1 ICYDRUIZSPKQOH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 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 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 2
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000013585 weight reducing agent Substances 0.000 description 2
- YVUIBEQQQMVVKZ-UHFFFAOYSA-N 1,1,1',1',4,4'-hexamethyl-3,3'-spirobi[2h-indene]-5,5'-diol Chemical compound C1C(C)(C)C2=CC=C(O)C(C)=C2C21CC(C)(C)C1=CC=C(O)C(C)=C21 YVUIBEQQQMVVKZ-UHFFFAOYSA-N 0.000 description 1
- RCWLSFRWEVSXFT-UHFFFAOYSA-N 1,1,1',1'-tetramethyl-4,4'-diphenyl-3,3'-spirobi[2H-indene]-5,5'-diol Chemical compound C1(=CC=CC=C1)C=1C(=CC=C2C(CC3(C=12)CC(C1=CC=C(C(=C13)C1=CC=CC=C1)O)(C)C)(C)C)O RCWLSFRWEVSXFT-UHFFFAOYSA-N 0.000 description 1
- RKIMETXDACNTIE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorocyclohexane Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F RKIMETXDACNTIE-UHFFFAOYSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- OUCSIUCEQVCDEL-UHFFFAOYSA-N 2,3,4-tribromophenol Chemical class OC1=CC=C(Br)C(Br)=C1Br OUCSIUCEQVCDEL-UHFFFAOYSA-N 0.000 description 1
- MAQOZOILPAMFSW-UHFFFAOYSA-N 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=C(CC=3C(=CC=C(C)C=3)O)C=C(C)C=2)O)=C1 MAQOZOILPAMFSW-UHFFFAOYSA-N 0.000 description 1
- DNCLEPRFPJLBTQ-UHFFFAOYSA-N 2-cyclohexyl-4-[1-(3-cyclohexyl-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound OC1=CC=C(C2(CCCCC2)C=2C=C(C(O)=CC=2)C2CCCCC2)C=C1C1CCCCC1 DNCLEPRFPJLBTQ-UHFFFAOYSA-N 0.000 description 1
- WKVWOPDUENJKAR-UHFFFAOYSA-N 2-cyclohexyl-4-[2-(3-cyclohexyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(C2CCCCC2)=CC=1C(C)(C)C(C=1)=CC=C(O)C=1C1CCCCC1 WKVWOPDUENJKAR-UHFFFAOYSA-N 0.000 description 1
- LXBMIVXYYFHKNI-UHFFFAOYSA-N 2-fluoro-4-[1,1,1,3,3,3-hexafluoro-2-(3-fluoro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(F)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(F)=C1 LXBMIVXYYFHKNI-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- ZDRSNHRWLQQICP-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 ZDRSNHRWLQQICP-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- CKNCVRMXCLUOJI-UHFFFAOYSA-N 3,3'-dibromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C(Br)=C1 CKNCVRMXCLUOJI-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- MLDIQALUMKMHCC-UHFFFAOYSA-N 4,4-Bis(4-hydroxyphenyl)heptane Chemical compound C=1C=C(O)C=CC=1C(CCC)(CCC)C1=CC=C(O)C=C1 MLDIQALUMKMHCC-UHFFFAOYSA-N 0.000 description 1
- RMFKONDLPMDUJM-UHFFFAOYSA-N 4-(2,6-difluoro-4-hydroxyphenyl)-3,5-difluorophenol Chemical compound FC1=CC(O)=CC(F)=C1C1=C(F)C=C(O)C=C1F RMFKONDLPMDUJM-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 description 1
- QIOCFZAEFQTCSO-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C=2C=C(C)C(O)=C(C)C=2)(C(F)(F)F)C(F)(F)F)=C1 QIOCFZAEFQTCSO-UHFFFAOYSA-N 0.000 description 1
- QGYQHGIANHIZJN-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-methylphenyl)propan-2-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C(C=2C=C(C)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QGYQHGIANHIZJN-UHFFFAOYSA-N 0.000 description 1
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 1
- MFTVULTZXLPBEK-UHFFFAOYSA-N 4-[1-(4-hydroxy-2,3-dimethylphenyl)decyl]-2,3-dimethylphenol Chemical compound C=1C=C(O)C(C)=C(C)C=1C(CCCCCCCCC)C1=CC=C(O)C(C)=C1C MFTVULTZXLPBEK-UHFFFAOYSA-N 0.000 description 1
- GFZVSEXTFJACGS-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-methylphenyl)decyl]-2-methylphenol Chemical compound C=1C=C(O)C(C)=CC=1C(CCCCCCCCC)C1=CC=C(O)C(C)=C1 GFZVSEXTFJACGS-UHFFFAOYSA-N 0.000 description 1
- UJCYBTZHUJWCMB-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-4-propan-2-ylcyclohexyl]phenol Chemical compound C1CC(C(C)C)CCC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UJCYBTZHUJWCMB-UHFFFAOYSA-N 0.000 description 1
- OVVCSFQRAXVPGT-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)cyclopentyl]phenol Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCC1 OVVCSFQRAXVPGT-UHFFFAOYSA-N 0.000 description 1
- ZBMWIKZBITYTCF-UHFFFAOYSA-N 4-[2,3-di(propan-2-yl)phenyl]phenol Chemical compound CC(C)C1=CC=CC(C=2C=CC(O)=CC=2)=C1C(C)C ZBMWIKZBITYTCF-UHFFFAOYSA-N 0.000 description 1
- WJZHBPSXJJQGJO-UHFFFAOYSA-N 4-[2,6-di(propan-2-yl)phenyl]phenol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C1=CC=C(O)C=C1 WJZHBPSXJJQGJO-UHFFFAOYSA-N 0.000 description 1
- GNEPQVKRIYTVIE-UHFFFAOYSA-N 4-[2-(3,5-difluoro-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2,6-difluorophenol Chemical compound C1=C(F)C(O)=C(F)C=C1C(C(F)(F)F)(C(F)(F)F)C1=CC(F)=C(O)C(F)=C1 GNEPQVKRIYTVIE-UHFFFAOYSA-N 0.000 description 1
- BKTRENAPTCBBFA-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-phenylphenyl)propan-2-yl]-2-phenylphenol Chemical compound C=1C=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC=C(O)C=1C1=CC=CC=C1 BKTRENAPTCBBFA-UHFFFAOYSA-N 0.000 description 1
- IJWIRZQYWANBMP-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-propan-2-ylphenyl)propan-2-yl]-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)C)=C1 IJWIRZQYWANBMP-UHFFFAOYSA-N 0.000 description 1
- QHJPJZROUNGTRJ-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)octan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCCCCC)C1=CC=C(O)C=C1 QHJPJZROUNGTRJ-UHFFFAOYSA-N 0.000 description 1
- WCUDAIJOADOKAW-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)pentan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCC)C1=CC=C(O)C=C1 WCUDAIJOADOKAW-UHFFFAOYSA-N 0.000 description 1
- RQTDWDATSAVLOR-UHFFFAOYSA-N 4-[3,5-bis(4-hydroxyphenyl)phenyl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC(C=2C=CC(O)=CC=2)=CC(C=2C=CC(O)=CC=2)=C1 RQTDWDATSAVLOR-UHFFFAOYSA-N 0.000 description 1
- BOCLKUCIZOXUEY-UHFFFAOYSA-N 4-[tris(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 BOCLKUCIZOXUEY-UHFFFAOYSA-N 0.000 description 1
- KNDDEFBFJLKPFE-UHFFFAOYSA-N 4-n-Heptylphenol Chemical compound CCCCCCCC1=CC=C(O)C=C1 KNDDEFBFJLKPFE-UHFFFAOYSA-N 0.000 description 1
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 0 CC(C)(*[C@]1C=CC=CC1)[S+]OC(C)(*)S*c1ccccc1 Chemical compound CC(C)(*[C@]1C=CC=CC1)[S+]OC(C)(*)S*c1ccccc1 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 description 1
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical group OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010097 foam moulding Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000008096 xylene 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
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
Definitions
- the present invention relates to a polycarbonate-polysiloxane resin.
- the resin glazing that replaces glass uses a polycarbonate resin that has excellent transparency, heat resistance, and impact resistance, and has a lower specific gravity than glass.
- Patent Document 1 examines a polycarbonate resin having a specific structural unit.
- the impact resistance at low temperatures is insufficient, and there is a problem that sufficient impact resistance is not exhibited especially in cold regions such as high latitudes and mountainous areas.
- An object of the present invention is to provide a polycarbonate-polysiloxane resin having excellent transparency, impact resistance, heat resistance, moldability, pencil hardness, and low specific gravity.
- a polycarbonate-polysiloxane resin containing a polycarbonate block containing a specific structural unit and a polysiloxane block has transparency, impact resistance, heat resistance, moldability, and pencil hardness.
- the present invention has been completed by finding that it is excellent in both properties and has low specific gravity. That is, according to the present invention, the subject of the invention is achieved by the following.
- Polycarbonate-polysiloxane resin containing a polycarbonate block (A-1) and a polysiloxane block (A-2), wherein the specific gravity of the resin is 1.10 or less, and the glass transition temperature of the resin is 100 to 190 ° C.
- R 1 and R 2 are independent of each other, a hydrogen atom, a halogen atom, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, and 6 to 6 carbon atoms.
- cycloalkyl groups 6 to 20 carbon atoms cycloalkoxy groups, 2 to 10 carbon atoms alkenyl groups, 6 to 14 carbon atoms aryl groups, 6 to 14 carbon atoms aryloxy groups, carbon atoms
- R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 are independently hydrogen atoms, alkyl groups having 1 to 18 carbon atoms, and carbon.
- R 23 , R 24 , R 25 and R 26 are independently substituted or unsubstituted with a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, and 6 to 12 carbon atoms.
- polycarbonate-polysiloxane resin according to any one of the above items 1 to 3, wherein the polycarbonate block (A-1) contains a structural unit represented by the following formula (4).
- R 27 and R 28 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and if there are a plurality of each, they may be the same or different, i. And j are integers of 1 to 4, respectively, and Y is at least one group selected from the group consisting of the groups represented by the following formula (5).
- R 29 , R 30 , and R 31 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and if there are a plurality of each, they may be the same or different.
- k is an integer from 1 to 3.
- polycarbonate block (A-1) 2,2-bis (4-hydroxy-3-methylphenyl) propane and 1,1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane , 1,1-bis (3-methyl-4-hydroxyphenyl) -3,3,5-trimethylcyclohexane, 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane from at least one
- the polycarbonate-polysiloxane resin according to any one of the above items 1 to 4, which comprises a unit to be induced.
- polycarbonate-polysiloxane resin according to any one of the above items 1 to 5, wherein the content of the polysiloxane block (A-2) is 5 to 50% by weight based on the entire polycarbonate-polysiloxane resin.
- the structural unit of the polycarbonate block (A-1) contains a unit derived from 2,2-bis (4-hydroxyphenyl) propane, and the content of the polysiloxane block (A-2) is polycarbonate-poly.
- polycarbonate-polysiloxane resin according to any one of the above items 1 to 8, wherein the polysiloxane domain of the polycarbonate-polysiloxane resin has an average size of 1 to 20 nm.
- the polycarbonate-polysiloxane resin of the present invention is excellent in transparency, impact resistance, heat resistance, moldability, and pencil hardness, and also has low specific gravity, so that it can be suitably used as a member for a vehicle body.
- the industrial effect it produces is exceptional.
- the polycarbonate-polysiloxane resin contains a polycarbonate block (A-1) and a polysiloxane block (A-2).
- the polycarbonate-polysiloxane resin of the present invention is characterized by having a specific gravity of 1.10 or less and a glass transition temperature of 100 to 190 ° C.
- the specific gravity of the polycarbonate-polysiloxane resin of the present invention is 1.10 or less, preferably 1.09 or less, more preferably 1.08 or less, still more preferably 1.07 or less.
- the specific gravity is measured according to the method for measuring the density and specific gravity of JIS K7112 plastic-non-foamed plastic (method C floating and sinking method).
- the glass transition temperature of the polycarbonate-polysiloxane resin of the present invention is in the range of 90 to 190 ° C, preferably in the range of 100 to 180 ° C, more preferably in the range of 110 to 175 ° C, and even more preferably 120. It is in the range of ⁇ 170 ° C. When it is in the range of the lower limit or more, the heat stability is good and preferable when used as a molded product.
- the glass transition temperature is measured at a heating rate of 20 ° C./min using a 2910 type DSC manufactured by TA Instruments Japan Co., Ltd.
- the polycarbonate block (A-1) is a portion of the polycarbonate polymer contained in the polycarbonate-polysiloxane resin. Specifically, the polycarbonate block (A-1) preferably contains a structural unit represented by the following formula (1).
- R 1 and R 2 are independently hydrogen atom, halogen atom, alkyl group having 1 to 18 carbon atoms, alkoxy group having 1 to 18 carbon atoms, and 6 to 20 carbon atoms.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and the like.
- alkyl group having 1 to 18 carbon atoms examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a dodecyl group and a tetradecyl group. .. It is preferably an alkyl group having 1 to 6 carbon atoms.
- alkoxy group having 1 to 18 carbon atoms examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a hexoxy group, and an octoxy group.
- An alkoxy group having 1 to 6 carbon atoms is preferable.
- Examples of the cycloalkyl group having 6 to 20 carbon atoms include a cyclohexyl group and a cyclooctyl group.
- a cycloalkyl group having 6 to 12 carbon atoms is preferable.
- Examples of the cycloalkoxy group having 6 to 20 carbon atoms include a cyclohexyloxy group and a cyclooctyloxy group.
- a cycloalkoxy group having 6 to 12 carbon atoms is preferable.
- alkenyl group having 2 to 10 carbon atoms examples include a metenyl group, an ethenyl group, a propenyl group, a butenyl group, a pentenyl group and the like.
- An alkenyl group having 2 to 6 carbon atoms is preferable.
- Examples of the aryl group having 6 to 14 carbon atoms include a phenyl group and a naphthyl group.
- Examples of the aryloxy group having 6 to 14 carbon atoms include a phenyloxy group and a naphthyloxy group.
- Examples of the aralkyl group having 7 to 20 carbon atoms include a benzyl group and a phenylethyl group.
- Examples of the aralkyloxy group having 7 to 20 carbon atoms include a benzyloxy group and a phenylethyloxy group.
- e and f are each independently an integer of 1 to 4.
- W is at least one group selected from the group consisting of a single bond or a group represented by the following formula (2).
- R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 are independently hydrogen atoms, alkyl groups having 1 to 18 carbon atoms, and carbon atoms.
- alkyl group having 1 to 18 carbon atoms examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group and a dodecyl group. It is preferably an alkyl group having 1 to 6 carbon atoms.
- Examples of the aryl group having 6 to 14 carbon atoms include a phenyl group and a naphthyl group. These may be substituted.
- Examples of the substituent include an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group and a butyl group.
- Examples of the aralkyl group having 7 to 20 carbon atoms include a benzyl group and a phenylethyl group.
- R 19 and R 20 are independently hydrogen atom, halogen atom, alkyl group having 1 to 18 carbon atoms, alkoxy group having 1 to 10 carbon atoms, cycloalkyl group having 6 to 20 carbon atoms, and carbon atom.
- Cycloalkoxy group with 6 to 20, alkoxy group with 2 to 10 carbon atoms, aryl group with 6 to 14 carbon atoms, aryloxy group with 6 to 10 carbon atoms, aralkyl group with 7 to 20 carbon atoms It represents at least one group selected from the group consisting of an alkoxyloxy group, a nitro group, an aldehyde group, a cyano group and a carboxyl group having 7 to 20 carbon atoms. If there are multiple, they may be the same or different.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and the like.
- alkyl group having 1 to 18 carbon atoms examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a dodecyl group and a tetradecyl group. .. It is preferably an alkyl group having 1 to 6 carbon atoms.
- alkoxy group having 1 to 10 carbon atoms examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group and the like.
- An alkoxy group having 1 to 6 carbon atoms is preferable.
- Examples of the cycloalkyl group having 6 to 20 carbon atoms include a cyclohexyl group and a cyclooctyl group.
- a cycloalkyl group having 6 to 12 carbon atoms is preferable.
- Examples of the cycloalkoxy group having 6 to 20 carbon atoms include a cyclohexyloxy group and a cyclooctyl group.
- a cycloalkoxy group having 6 to 12 carbon atoms is preferable.
- alkenyl group having 2 to 10 carbon atoms examples include a metenyl group, an ethenyl group, a propenyl group, a butenyl group, a pentenyl group and the like.
- Alkyl groups having 1 to 6 carbon atoms are preferable.
- Examples of the aryl group having 6 to 14 carbon atoms include a phenyl group and a naphthyl group.
- Examples of the aryloxy group having 6 to 14 carbon atoms include a phenyloxy group and a naphthyloxy group.
- Examples of the aralkyl group having 7 to 20 carbon atoms include a benzyl group and a phenylethyl group.
- Examples of the aralkyloxy group having 7 to 20 carbon atoms include a benzyloxy group and a phenylethyloxy group.
- G is an integer of 1 to 10, preferably an integer of 1 to 6.
- h is an integer of 4 to 7, preferably an integer of 4 to 5.
- the polycarbonate block (A-1) is particularly preferably one containing a structural unit represented by the following formula (4).
- R 27 and R 28 are each independently an alkyl group having a hydrogen atom or a carbon atom number of 1 to 4. When there are a plurality of R 27 and R 28 , they may be the same or different. i and j are integers of 1 to 4, respectively.
- Y is at least one group selected from the group consisting of the groups represented by the following formula (5).
- R 29 , R 30 , and R 31 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- k is an integer of 1 to 3.
- the polysiloxane block (A-2) is a polysiloxane-based portion contained in the polycarbonate-polysiloxane resin, and the type thereof is not particularly limited.
- the polysiloxane block preferably contains a structural unit represented by the following formula (3).
- R 23 , R 24 , R 25 and R 26 are independently substituted or unsubstituted with a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, and 6 to 12 carbon atoms. It is at least one group selected from the group consisting of aryl groups.
- alkyl group having 1 to 12 carbon atoms examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group and a dodecyl group. It is preferably an alkyl group having 1 to 6 carbon atoms.
- Examples of the substituted or unsubstituted aryl group having 6 to 12 carbon atoms include a phenyl group and a naphthyl group.
- Examples of the substituent include an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group and a hexyl group. It is particularly preferable that R 23 , R 24 , R 25 and R 26 are methyl groups.
- R 21 and R 22 are each independently at least one group selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms, and halogen.
- the atom include a fluorine atom, a chlorine atom, a bromine atom and the like.
- alkyl group having 1 to 10 carbon atoms examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group and a dodecyl group. It is preferably an alkyl group having 1 to 6 carbon atoms.
- alkoxy group having 1 to 10 carbon atoms examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a hexoxy group, a heptoxy group, and an octoxy group. It is preferably an alkoxy group having 1 to 6 carbon atoms. It is particularly preferable that R 21 and R 22 are hydrogen atoms or methoxy groups.
- P is a natural number of 1 to 150, preferably a natural number of 5 to 100, more preferably a natural number of 10 to 80, and particularly preferably a natural number of 20 to 50.
- the average chain length p is calculated by nuclear magnetic resonance (NMR) measurement.
- the repeating unit of p may include a number of units having different R 23 and R 24 .
- the unit may be random.
- hydroxyaryl-terminated polysiloxane raw materials having two or more different average chain lengths p may be mixed and prepared.
- a method for mixing and preparing polysiloxane raw materials even in a method of mixing appropriate polysiloxane raw materials having hydroxyaryl-modified ends, polysiloxane precursors having an appropriate average chain length before hydroxyaryl-denaturing the ends are used. Either of the methods of premixing the above and then denaturing the terminal with hydroxyaryl may be used.
- X is a divalent aliphatic group having 2 to 8 carbon atoms.
- the divalent aliphatic group include an alkylene group having 2 to 8 carbon atoms.
- the alkylene group include an ethylene group, a trimethylene group and a tetramethylene group.
- the polycarbonate-polysiloxane resin of the present invention may contain other resins as long as the effects of the present invention are not impaired.
- the polycarbonate resin is particularly preferable from the viewpoint of compatibility with the polycarbonate-polysiloxane resin of the present invention.
- the polycarbonate-polysiloxane resin in the present invention can be produced by the steps (I) and (II).
- step (I) a dihydric phenol represented by the following formula (7) is reacted with phosgene in a mixed solution of an organic solvent insoluble in water and an alkaline aqueous solution to obtain a carbonate oligomer having a terminal chlorohomate group. This is a step of preparing a solution to be contained.
- Examples of the divalent phenol represented by the above formula (7) include 4,4'-biphenol, 3,3', 5,5'-tetrafluoro-4,4'-biphenol, ⁇ , ⁇ '-bis. (4-Hydroxyphenyl) -o-diisopropylbenzene, ⁇ , ⁇ '-bis (4-hydroxyphenyl) -m-diisopropylbenzene (hereinafter sometimes abbreviated as "BPM”), ⁇ , ⁇ '-bis (4) -Hydroxyphenyl) -p-diisopropylbenzene, ⁇ , ⁇ '-bis (4-hydroxyphenyl) -m-bis (1,1,1,3,3,3-hexafluoroisopropyl) benzene, 1,1-bis (4-Hydroxyphenyl) cyclohexane (hereinafter sometimes abbreviated as "BPZ”), 1,1-bis (4-hydroxyphenyl)
- BPC 4-Hydroxy-3-methylphenyl) propane
- BP26XA 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane
- BP26XA 2,2-bis (4-hydroxyphenyl) butane
- BP26XA 2,2-bis (4-hydroxyphenyl) pentane
- 2,2-bis (4-hydroxy-3-phenylphenyl) propane 2,2-bis (3-isopropyl-4-hydroxyphenyl) propane
- 2,2-bis (3-t-butyl-4-hydroxyphenyl) propane 2,2-bis (4-hydroxyphenyl) butane, 4,4-bis (4-Hydroxyphenyl) heptane
- 1,1-bis (4-hydroxyphenyl) decane 1,1-bis (3-methyl-4-hydroxyphenyl) decane
- 1,1-bis (2,3-dimethyl-4-hydroxyphenyl) decane 1,1-bis (2,3-d
- BPM, BPZ, BPTMC, BPOCTMC, 3,3'-dimethyl-4,4'-dihydroxydiphenylsulfide, BPA, BPC, BP26XA, BPAF, 6,6'-dihydroxy-3,3,3', 3'-tetramethyl-1,1'-spirobiindan and 1,1-bis (4-hydroxyphenyl) decane are preferred.
- BPTMC, BPOCTMC, BPA, BPC, BP26XA and BPAF are more preferable, and BPTCC, BPOCTMC, BPA, BPC and BP26XA are particularly preferable.
- These divalent phenols may be used alone or in combination of two or more.
- Step (II) is a step of interfacially polymerizing the hydroxyaryl-terminated polysiloxane represented by the following formula (8) and the carbonate oligomer prepared in the step (I) to obtain the polycarbonate-polysiloxane resin of the present invention.
- hydroxyaryl-terminated polysiloxane represented by the above formula (8) for example, the following compounds are preferably used.
- the hydroxyaryl-terminated polysiloxane contains phenols having an olefinic unsaturated carbon-carbon bond, preferably vinylphenol, 2-allylphenol, isopropenylphenol, and 2-methoxy-4-allylphenol at a predetermined degree of polymerization. It is easily produced by subjecting the terminal of the polysiloxane chain to undergo a hydrosyllation reaction.
- (2-allylphenol) -terminated polysiloxane (2-methoxy-4-allylphenol) -terminated polysiloxane, in particular (2-allylphenol) -terminated polydimethylsiloxane, and (2-methoxy-4-allyphenol) -terminated polysiloxane.
- Allylphenol) -terminated polydimethylsiloxane is preferred.
- the hydroxyaryl terminal polysiloxane only one type may be used, or two or more types may be used in combination.
- the average siloxane repetition number p of the hydroxyaryl-terminated polysiloxane is preferably 1 to 150, more preferably 5 to 100, still more preferably particularly preferably 10 to 80, and particularly preferably 20. ⁇ 50. Above the lower limit of the suitable range, the impact resistance is excellent, and above the upper limit of the suitable range, the transparency is excellent.
- the average chain length p can be calculated by 1H-NMR measurement.
- Resins above the above lower limit have a high rheological property modification effect by introducing a polysiloxane moiety with low cohesive force, and tend to increase the structural viscosity index. As a result, high fluidity during shear flow is maintained and moldability is good. Resins below the above upper limit tend to reduce the average size of the polysiloxane domain. As a result, it is possible to obtain a resin molded product having excellent transparency even under molding conditions in which the product stays in the cylinder for a long time at a high temperature. The number of moles per unit weight of the polysiloxane unit below the upper limit increases, and the unit can be easily incorporated evenly into the polycarbonate.
- the polysiloxane domain refers to a domain containing polysiloxane as a main component dispersed in a matrix of polycarbonate, and may contain other components.
- the polysiloxane domain is not necessarily composed of a single component because the structure is formed by phase separation from the polycarbonate as a matrix.
- the content of the polysiloxane component in the total weight of the resin is preferably 1 to 70% by weight.
- the lower limit of the content of the polysiloxane component is preferably 3% by weight or more, 5% by weight or more, 8% by weight or more, 10% by weight or more, 20% by weight or more, 30% by weight or more, 35% by weight or more, 40% by weight. It may be included in the above.
- the upper limit may preferably include 60% by weight or less, 50% by weight or less, 45% by weight or less, 40% by weight or less, 30% by weight or less, and 20% by weight or less. Above the lower limit of the suitable range, impact resistance is excellent, and above the upper limit of the suitable range, stable transparency that is not easily affected by molding conditions can be easily obtained.
- the polysiloxane content can be calculated by 1H-NMR measurement.
- a comonomer other than the above-mentioned divalent phenol and hydroxyaryl-terminated polysiloxane can be used in combination as long as it does not interfere with the production method of the present invention.
- the polycarbonate-polysiloxane resin of the present invention can be a branched polycarbonate resin by using a branching agent in combination with the above-mentioned divalent phenolic compound.
- Examples of the trifunctional or higher polyfunctional aromatic compound used in such a branched polycarbonate resin include fluoroglucolcin, fluoroglucolside, or 4,6-dimethyl-2,4,6-tris (4-hydrochidiphenyl) hepten-2, 2.
- the branching agent is used during the interfacial polycondensation reaction after the completion of the production reaction. It may be a method of addition.
- the ratio of the carbonate constituent units derived from the branching agent is preferably 0.005 to 1.5 mol%, more preferably 0.01 to 1.2 mol%, and particularly preferably 0.01 to 1.2 mol%, based on the total amount of the carbonate constituent units constituting the resin. Is 0.05 to 1.0 mol%.
- the amount of the branched structure can be calculated by 1H-NMR measurement.
- step (I) a mixed solution containing an oligomer of a dihydric phenol having a terminal chloroformate group is obtained, and then the hydroxyaryl-terminated polysiloxane represented by the above formula (8) is subjected to divalent phenol while stirring the mixed solution.
- a polycarbonate-polysiloxane resin is obtained by polycondensing the hydroxyaryl-terminated polysiloxane and the oligomer at a rate of 0.004 mol equivalent / min or less with respect to the charged amount of the above.
- a solvent inert to various reactions such as those used in the production of known polycarbonate may be used alone or as a mixed solvent.
- Typical examples include hydrocarbon solvents such as xylene and halogenated hydrocarbon solvents such as methylene chloride and chlorobenzene.
- a halogenated hydrocarbon solvent such as methylene chloride is preferably used.
- the concentration of divalent phenol is preferably 500 g / L or less, more preferably 450 g / L or less, still more preferably 300 g / L or less.
- the lower limit of the concentration of divalent phenol is preferably 150 g / L or more from the viewpoint of production efficiency.
- an acid binder may be added as appropriate in consideration of the stoichiometric ratio (equivalent) of the reaction.
- the acid binder for example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, organic bases such as pyridine, and mixtures thereof are used.
- the post-added divalent phenol is used. It is preferable to use 2 equivalents or an excess amount of alkali with respect to the total number of moles with the hydroxyaryl-terminated polysiloxane (usually 1 mol corresponds to 2 equivalents).
- Polycondensation by the interfacial polycondensation reaction between the divalent phenol oligomer and the hydroxyaryl terminal polysiloxane is performed by vigorously stirring the above mixture.
- a terminal terminator or a molecular weight modifier is usually used.
- the terminal terminator include compounds having a monovalent phenolic hydroxyl group, and in addition to ordinary phenols, p-tert-butylphenols, p-cumylphenols, tribromophenols, etc., long-chain alkylphenols and aliphatic carboxylic acids Examples thereof include chloride, aliphatic carboxylic acid, hydroxybenzoic acid alkyl ester, hydroxyphenyl alkyl acid ester, and alkyl ether phenol.
- the amount used is in the range of 100 to 0.5 mol, preferably 50 to 2 mol, with respect to 100 mol of all the divalent phenolic compounds used, and it is naturally possible to use two or more kinds of compounds in combination. be.
- a catalyst such as a tertiary amine such as triethylamine or a quaternary ammonium salt may be added to promote the polycondensation reaction.
- the reaction time of the polymerization reaction needs to be relatively long in order to reduce the unreacted polysiloxane component. It is preferably 30 minutes or longer, more preferably 50 minutes or longer. On the other hand, since precipitation of the polymer may occur by stirring the reaction solution for a long time, it is preferably 180 minutes or less, more preferably 90 minutes or less.
- the reaction pressure can be reduced pressure, normal pressure, or pressurization, but usually, normal pressure or the self-pressure of the reaction system can be preferably used.
- the reaction temperature is selected from the range of -20 to 50 ° C, and in many cases, heat is generated due to polymerization, so it is desirable to cool with water or ice.
- an antioxidant such as sodium sulfite or hydrosulfide may be added.
- the viscosity average molecular weight of the polycarbonate-polysiloxane resin of the present invention is preferably 15,000 to 40,000, more preferably 16,000 to 35,000, still more preferably 17,000 to 30,000, and particularly preferably 18. It is 000 to 25,000. Within the above range, it is easy to obtain practical mechanical strength in many fields, and since it has an appropriate melt viscosity during molding, problems such as thermal deterioration are suppressed and it is mixed with the polycarbonate resin as needed. The difference in melt viscosity is small and the kneadability is good. Furthermore, the efficiency of the water washing process at the time of resin production is good, and the productivity is excellent.
- the viscosity average molecular weight of the polycarbonate resin in the present invention was first determined by using an Ostwald viscometer from a solution in which 0.7 g of the resin was dissolved in 100 ml of methylene chloride at 20 ° C. for the specific viscosity ( ⁇ SP) calculated by the following formula.
- Specific viscosity ( ⁇ SP) (tt 0 ) / t 0 [T0 is the number of seconds for methylene chloride to fall, and t is the number of seconds for the sample solution to fall]
- the viscosity average molecular weight Mv was calculated from the obtained specific viscosity ( ⁇ SP) by the following mathematical formula.
- the pencil hardness of the polycarbonate-polysiloxane resin of the present invention is preferably 2B or more. In terms of excellent scratch resistance, it is more preferably HB or higher, and even more preferably F or higher.
- the pencil hardness is 4H or less and has a sufficient function.
- the pencil hardness is a hardness that does not leave scratch marks even when the resin of the present invention is rubbed with a pencil having a specific pencil hardness, and is measured according to JIS K-5600. It is preferable to use the pencil hardness used for the surface hardness test of the resulting coating film as an index.
- Pencil hardness becomes softer in the order of 9H, 8H, 7H, 6H, 5H, 4H, 3H, 2H, H, F, HB, B, 2B, 3B, 4B, 5B, 6B, the hardest is 9H, and the hardest.
- the soft one is 6B.
- the polycarbonate-polysiloxane resin of the present invention preferably has a ductile fracture form.
- the value of the total light transmittance of the polycarbonate-polysiloxane resin of the present invention is preferably 80% or more, more preferably 85% or more, still more preferably 88% or more.
- the haze value is preferably 5.0 or less, more preferably 3.0 or less, and even more preferably 2.0 or less. By setting the above values, the appearance of the molded product is excellent and preferable.
- the total light transmittance and the haze can be measured in accordance with ASTM D1003 using Haze Meter NDH 2000 manufactured by Nippon Denshoku Kogyo Co., Ltd. in a thickness of 2.0 mm of the obtained resin plate.
- the average size of the polysiloxane domain is preferably in the range of 1 to 20 nm, more preferably in the range of 2 to 15 nm. If it is less than the lower limit of such a range, impact resistance is not sufficiently exhibited, and if it exceeds the upper limit of such a range, transparency is not stably exhibited.
- 2,2-bis (4-hydroxy-3-methylphenyl) propane and 1,1-bis (4-) are the structural units of the polycarbonate block (A-1). Hydroxyphenyl) -3,3,5-trimethylcyclohexane, 1,1-bis (3-methyl-4-hydroxyphenyl) -3,3,5-trimethylcyclohexane, 2,2-bis (4-hydroxy-3, It preferably contains a unit derived from at least one of 5-dimethylphenyl) propane.
- the content of the polysiloxane block (A-2) is preferably 1 to 70% by weight based on the entire polycarbonate-polysiloxane resin. It is more preferably from 60% by weight, still more preferably from 5 to 50% by weight.
- a preferred embodiment (2) includes a unit derived from 2,2-bis (4-hydroxyphenyl) propane as the structural unit of the polycarbonate block (A-1), and the polysiloxane block (2).
- the content of A-2) is preferably 30 to 70% by weight, more preferably 35 to 60% by weight, still more preferably 40 to 50% by weight, based on the entire polycarbonate-polysiloxane resin.
- the polycarbonate-polysiloxane resin of the present invention can contain various flame retardants, reinforced fillers, and additives that are usually blended with the polycarbonate resin as long as the effects of the present invention are not impaired.
- the polycarbonate-polysiloxane resin can be pelletized by melt-kneading using an extruder such as a single-screw extruder or a twin-screw extruder. In producing such pellets, various flame retardants, strengthening fillers and additives can also be blended.
- thermoplastic resins particularly aromatic polycarbonate resins
- organic metal salt-based flame retardants for example, organic sulfonic acid alkali (soil)
- C Metal salts, brate metal salt flame retardants, tinic acid metal salt flame retardants, etc.), organic phosphorus flame retardants (eg, monophosphate compounds, phosphate oligomer compounds, phosphonate oligomer compounds, phosphonitrile oligomer compounds, phosphons, etc.) Acid amide compounds, phosphazene, etc.), silicone flame retardants made of silicone compounds, fibrillated PTFE and the like.
- organometallic salt flame retardants and organophosphorus flame retardants are particularly preferable.
- the compounding of such a compound brings about improvement of flame retardancy, but in addition to that, improvement of antistatic property, fluidity, rigidity, thermal stability and the like is brought about based on the property of each compound.
- the polycarbonate-polysiloxane resin can be manufactured by injection molding pellets usually produced as described above to produce various molded products. Further, it is also possible to directly convert the resin melt-kneaded by the extruder into a sheet, a film, a modified extrusion-molded product, a direct blow-molded product, and an injection-molded product without passing through pellets.
- injection molding not only ordinary molding methods, but also injection compression molding, injection press molding, gas-assisted injection molding, foam molding (including those by injecting supercritical fluid), insert molding, and insert molding, depending on the intended purpose.
- Molded products can be obtained using injection molding methods such as in-mold coating molding, heat insulating mold molding, rapid heating and cooling mold molding, two-color molding, sandwich molding, and ultra-high speed injection molding.
- injection molding methods such as in-mold coating molding, heat insulating mold molding, rapid heating and cooling mold molding, two-color molding, sandwich molding, and ultra-high speed injection molding.
- injection molding methods such as in-mold coating molding, heat insulating mold molding, rapid heating and cooling mold molding, two-color molding, sandwich molding, and ultra-high speed injection molding.
- the advantages of these various molding methods are already widely known.
- either a cold runner method or a hot runner method can be selected for molding.
- the polycarbonate-polysiloxane resin can also be used in the form of various deformed extruded products, sheets, films and the like by extrusion molding. Inflation method, calendar method, casting method, etc. can also be used for forming sheets and films. Further, it can be molded as a heat-shrinkable tube by applying a specific stretching operation. Further, the polycarbonate-polysiloxane resin of the present invention can be made into a molded product by rotary molding, blow molding or the like.
- various surface treatments can be applied to the molded product made of polycarbonate-polysiloxane resin.
- Surface treatment here means a new layer on the surface layer of resin molded products such as thin-film deposition (physical vapor deposition, chemical vapor deposition, etc.), plating (electroplating, electroless plating, hot-dip plating, etc.), painting, coating, printing, etc. It is formed, and the method used for ordinary polycarbonate resin can be applied.
- Specific examples of the surface treatment include various surface treatments such as a hard coat, a water / oil repellent coat, an ultraviolet absorption coat, an infrared absorption coat, and metallizing (vapor deposition, etc.).
- the polycarbonate-polysiloxane resin of the present invention has a high degree of compatibility with transparency, impact resistance, heat resistance, moldability, pencil hardness, and low specific gravity, and is widely used in the fields of optical components, electrical / electronic equipment, and mobility. Can be used. In particular, it is suitably used for automobile lamp lenses and automobile interior / exterior members mainly formed by injection molding or the like, lighting covers mainly formed by extrusion molding or the like, resin windows or front panel applications.
- a resin is injected by an injection molding machine (J-75E3 manufactured by Japan Steel Works, Ltd.) under the conditions of a cylinder temperature of 300 ° C. and a mold temperature of 80 ° C., with a holding time of 20 seconds and a cooling time of 20 seconds, and a width of 50 mm.
- a three-stage resin plate having a length of 90 mm and a thickness of 3 mm (length 20 mm), 2 mm (length 45 mm), and 1 mm (length 25 mm) from the gate side was molded and various evaluations were carried out.
- Vacuum heat press molding (Comparative Examples 5, 6, 12) Using a vacuum heat press forming machine (compression forming machine: SFV-10, vacuum pump unit: GXD-360) manufactured by Kondo Metal Industry Co., Ltd., a disk-shaped resin plate with a thickness of 2 mm and a diameter of 5 cm is formed. , Various evaluations were carried out. The press molding conditions were a mold temperature of 300 ° C., a primary pressure of 1 MPa (30 seconds), and a secondary pressure of 1.5 MPa (5 minutes).
- Total light transmittance and haze Total light transmittance (%) and haze (%) at a thickness of 2.0 mm are based on ASTM D1003 using Haze Meter NDH 2000 manufactured by Nippon Denshoku Kogyo Co., Ltd. And measured.
- Image analysis software Win ROOF Ver. Particle analysis was performed using 6.6 (Mitani Shoji Co., Ltd.) to obtain the average size and particle size distribution (frequency distribution) of the polysiloxane domain in the sample flakes.
- the maximum major axis (the length when any two points on the outer contour line of the particle are selected so that the length between them is maximized) is used as the size of each domain.
- the same analysis was performed on 5 sample sections, and the average value was taken as the value of each sample.
- Pencil hardness Based on JIS K5600, draw a line on the surface of the resin plate in a constant temperature room with an ambient temperature of 23 ° C while keeping an angle of 45 degrees and apply a load of 750 g to the surface condition. It was evaluated visually. Load: 750g Measurement speed: 50 mm / min Measurement distance: 7 mm Pencil: Hi-uni made by Mitsubishi Pencil
- polydimethylsiloxane 1031 parts of a 25% sodium hydroxide aqueous solution was added, and a solution in which 83.2 parts of p-tert-butylphenol was dissolved in 5477 parts of methylene chloride was added, and the polydimethylsiloxane (hereinafter referred to as “polydimethylsiloxane”) was used as a hydroxyaryl-terminated polysiloxane while stirring.
- polydimethylsiloxane polydimethylsiloxane
- the divalent phenol was changed to 2355 parts of BPC, 810 parts of BPOCTMC, and 74.3 parts of p-tert-butylphenol, and was produced by the same method as in Production Example 1 except that hydroxyaryl-terminated polysiloxane was not used.
- the viscosity average molecular weight of the obtained resin was 19,100, and the glass transition temperature was 181 ° C.
- Example 1 The resins obtained in Production Examples 1 to 6 were injection-molded to prepare a three-stage resin plate, and the moldability, specific gravity, total light transmittance, haze, impact resistance, domain size, and pencil hardness were evaluated. .. The evaluation results are shown in Table 1.
- the polycarbonate-polysiloxane resin of the present invention has a high degree of compatibility with transparency, impact resistance, heat resistance, moldability, pencil hardness, and low specific gravity.
- the polycarbonate-polysiloxane resin of the present invention has a high degree of compatibility with transparency, impact resistance, heat resistance, moldability, pencil hardness, and low specific gravity, and is widely used in the fields of optical components, electrical / electronic equipment, and mobility. Can be used.
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| JPH06174945A (ja) * | 1992-12-10 | 1994-06-24 | Idemitsu Petrochem Co Ltd | プラスチック光電送性繊維 |
| JP2003529637A (ja) * | 2000-03-23 | 2003-10-07 | バイエル アクチェンゲゼルシャフト | ポリエステルカーボネートおよびそれを用いて製造されるデータキャリア |
| US20080081884A1 (en) * | 2006-09-29 | 2008-04-03 | General Electric Company | Polycarbonate-polysiloxane copolymer compositions and articles formed therefrom |
| JP2011046911A (ja) * | 2009-07-29 | 2011-03-10 | Teijin Chem Ltd | ポリカーボネート−ポリジオルガノシロキサン共重合体、成形品およびその製造方法 |
| JP2012153824A (ja) * | 2011-01-27 | 2012-08-16 | Teijin Chem Ltd | ポリカーボネート樹脂組成物および成形品 |
| JP2018510953A (ja) * | 2015-04-07 | 2018-04-19 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | ポリシロキサンおよびジヒドロキシジフェニルシクロアルカン（コ）ポリカーボネートのブロック共縮合物 |
| JP2020114893A (ja) * | 2019-01-17 | 2020-07-30 | 帝人株式会社 | 食品冷凍冷却機械用樹脂部品 |
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| JP5680886B2 (ja) | 2009-06-26 | 2015-03-04 | 出光興産株式会社 | ポリカーボネート共重合体、それを用いた塗工液、及び電子写真感光体 |
| JP2012108298A (ja) * | 2010-11-17 | 2012-06-07 | Teijin Chem Ltd | 輝度上昇フィルム |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06174945A (ja) * | 1992-12-10 | 1994-06-24 | Idemitsu Petrochem Co Ltd | プラスチック光電送性繊維 |
| JP2003529637A (ja) * | 2000-03-23 | 2003-10-07 | バイエル アクチェンゲゼルシャフト | ポリエステルカーボネートおよびそれを用いて製造されるデータキャリア |
| US20080081884A1 (en) * | 2006-09-29 | 2008-04-03 | General Electric Company | Polycarbonate-polysiloxane copolymer compositions and articles formed therefrom |
| JP2011046911A (ja) * | 2009-07-29 | 2011-03-10 | Teijin Chem Ltd | ポリカーボネート−ポリジオルガノシロキサン共重合体、成形品およびその製造方法 |
| JP2011046913A (ja) * | 2009-07-29 | 2011-03-10 | Teijin Chem Ltd | ポリカーボネート−ポリジオルガノシロキサン共重合体 |
| JP2012153824A (ja) * | 2011-01-27 | 2012-08-16 | Teijin Chem Ltd | ポリカーボネート樹脂組成物および成形品 |
| JP2018510953A (ja) * | 2015-04-07 | 2018-04-19 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | ポリシロキサンおよびジヒドロキシジフェニルシクロアルカン（コ）ポリカーボネートのブロック共縮合物 |
| JP2020114893A (ja) * | 2019-01-17 | 2020-07-30 | 帝人株式会社 | 食品冷凍冷却機械用樹脂部品 |
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| JP7515599B2 (ja) | 2024-07-12 |
| JP2024009163A (ja) | 2024-01-19 |
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