EP0000732A1 - Mélanges de polyarylsulfones réticulées avec des polycarbonates et leur utilisation dans la préparation de feuilles extrudées - Google Patents
Mélanges de polyarylsulfones réticulées avec des polycarbonates et leur utilisation dans la préparation de feuilles extrudées Download PDFInfo
- Publication number
- EP0000732A1 EP0000732A1 EP7878100509A EP78100509A EP0000732A1 EP 0000732 A1 EP0000732 A1 EP 0000732A1 EP 7878100509 A EP7878100509 A EP 7878100509A EP 78100509 A EP78100509 A EP 78100509A EP 0000732 A1 EP0000732 A1 EP 0000732A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- bis
- hydroxyphenyl
- weight
- polycarbonate
- polycarbonates
- 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
Links
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 36
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 36
- 239000000203 mixture Substances 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 238000001125 extrusion Methods 0.000 claims abstract description 14
- 150000003457 sulfones Chemical class 0.000 claims description 6
- 230000007797 corrosion Effects 0.000 abstract description 4
- 238000005260 corrosion Methods 0.000 abstract description 4
- 229920006337 unsaturated polyester resin Polymers 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 description 18
- 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 16
- 229920000110 poly(aryl ether sulfone) Polymers 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- -1 haloaryl compound Chemical class 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000002367 halogens Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 229920002492 poly(sulfone) Polymers 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 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 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 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 2
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 2
- 239000006085 branching agent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005027 hydroxyaryl group Chemical group 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000090 poly(aryl ether) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KPRRZWRPYOEXGI-UHFFFAOYSA-N 1,3,5-tris[(4-chlorophenyl)sulfonyl]benzene Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 KPRRZWRPYOEXGI-UHFFFAOYSA-N 0.000 description 1
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 1
- KYGLCUAXJICESS-UHFFFAOYSA-N 2-[2,3-di(propan-2-yl)phenyl]phenol Chemical class CC(C)C1=CC=CC(C=2C(=CC=CC=2)O)=C1C(C)C KYGLCUAXJICESS-UHFFFAOYSA-N 0.000 description 1
- WYCSOUAFIFIEMA-UHFFFAOYSA-N 2-chloro-1,3-bis[(4-chlorophenyl)sulfonyl]benzene Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1Cl WYCSOUAFIFIEMA-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
- 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 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
- AZZWZMUXHALBCQ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C=C(C)C(O)=C(C)C=2)=C1 AZZWZMUXHALBCQ-UHFFFAOYSA-N 0.000 description 1
- RSSGMIIGVQRGDS-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-phenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 RSSGMIIGVQRGDS-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
- BWCAVNWKMVHLFW-UHFFFAOYSA-N 4-[1-(4-hydroxy-3,5-dimethylphenyl)cyclohexyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C2(CCCCC2)C=2C=C(C)C(O)=C(C)C=2)=C1 BWCAVNWKMVHLFW-UHFFFAOYSA-N 0.000 description 1
- RIBPTGQSXYJRBQ-UHFFFAOYSA-N 4-[2,5-di(propan-2-yl)phenyl]phenol Chemical compound CC(C)C1=CC=C(C(C)C)C(C=2C=CC(O)=CC=2)=C1 RIBPTGQSXYJRBQ-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
- QFZPRQBHIIKVQT-UHFFFAOYSA-N 4-[3-(4-hydroxy-3,5-dimethylphenyl)-3-methylbutyl]-2,6-dimethylphenol;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.CC1=C(O)C(C)=CC(CCC(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 QFZPRQBHIIKVQT-UHFFFAOYSA-N 0.000 description 1
- PBJXNIRVJFJFPL-UHFFFAOYSA-N 4-[3-(4-hydroxyphenyl)butyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)CCC1=CC=C(O)C=C1 PBJXNIRVJFJFPL-UHFFFAOYSA-N 0.000 description 1
- CIEGINNQDIULCT-UHFFFAOYSA-N 4-[4,6-bis(4-hydroxyphenyl)-4,6-dimethylheptan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)CC(C)(C=1C=CC(O)=CC=1)CC(C)(C)C1=CC=C(O)C=C1 CIEGINNQDIULCT-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
- 244000198134 Agave sisalana Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- IEPIYXWWJPPIEM-UHFFFAOYSA-N benzene-1,3-diol;benzene-1,4-diol Chemical compound OC1=CC=C(O)C=C1.OC1=CC=CC(O)=C1 IEPIYXWWJPPIEM-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 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
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/06—Polysulfones; Polyethersulfones
Definitions
- polyarylsulfone-polycarbonate mixtures according to the invention provide extrusion films with an excellent property profile, even though they contain a polycarbonate component which is not extrudable without molecular weight degradation.
- Branched polyarylsulfones which are suitable according to the invention are in particular the branched polyaryl sulfones according to US Pat. No. 3,960,815 or DT-OS 2,305,413 (Le A 14 799), whose Mw (weight average molecular weight, measured for example by means of light scattering) between about 15,000 and about 55,000, preferably between are around 20,000 and 40,000.
- tri- or more than trihydric phenols which can be prepared by reacting p-alkyl-substituted monophenols with unsubstituted o-positions with compounds providing formaldehyde or formaldehyde, such as for example the triephenol from p-kreeol and formaldehyde, the 2,6-bis- (2 'hydroxy-5'-methyl-beazyl) -4-methyl-phenol. 2,6-bis- (2'- hydroxy-5'-iaopropyl-benzyl) -4-iaopropenyl-phenol and Bie [2-hydroxy-3- (2'-hydroxy5'-methylbeneyl-5-methyl-phenyl] methane.
- the halogen substituents can also be activated by other electronically attractive groups, that is to say those with a positive sigma value. (See Chem. Rev. 49 (1951) page. 273 ff. And Quart. Rev. 12 (1958) 1 ff.); preferred are substituents whose sigma values are greater than +1.
- Alkali metal hydroxylates derived from the aromatic compounds containing two, three or more than three hydroxyl groups may be mentioned, for example, the corresponding sodium hydroxylates or potassium hydroxylates.
- the branched aromatic polyether sulfones also contain in amounts between 0.01 mol% and 2 mol% of trishydroxylate residues or hydroxylate residues resulting from the incorporation of the branching components and having more than three hydroxylate groups and / or three- or more than three-bonded, from the haloaryl compounds, which have three or more than three aryl-bonded halogen substituents which can be substituted under the reaction conditions of polyaryl ether sulfone production, resulting aryl branching residues.
- the aromatic polycarbonates can be branched through the incorporation of small amounts, preferably amounts between 0.05 and 2.0 mol% (based on the diphenols used), of three- or more than three-functional compounds, in particular those with three or more than three phenolic hydroxyl groups.
- Polycarbonates of this type are e.g. in German laid-open publications 1 570 533, 1 595 762, 2 116 974, 2 113 347 and 2 500 092, British patent 1,079,821 and US patent 3,544,514.
- the weight average molecular weights of the polycarbonates suitable according to the invention should be above 60,000, preferably between 65,000 and 120,000 and in particular between 75,000 and 95,000. (Determined from the intrinsic viscosity, measured in CH 2 Cl 2 solution).
- Aromatic polycarbonates for the purposes of the invention are, in particular, homopolycarbonates from bis-2- (4-hydroxyphenyl) propane (bisphenol-A) and copolycarbonates from at least 30 mol%, preferably at least 60 mol% and in particular at least 80 mol% of bisphenol A and up to 70 mol -.%, preferably up to 40 mol% and in particular up to 20 mol% of other diphenols (The mole percentages are each based on total molar amount of co-condensed diphenols).
- bisphenol-A bis-2- (4-hydroxyphenyl) propane
- copolycarbonates from at least 30 mol%, preferably at least 60 mol% and in particular at least 80 mol% of bisphenol A and up to 70 mol -.%, preferably up to 40 mol% and in particular up to 20 mol% of other diphenols (The mole percentages are each based on total molar amount of co-condensed diphenols).
- diphenols bis (4-hydroxyphenyl) methane (bisphenol F), 2,4-bis (4-hydroxyphenyl) butane, 1,1-bis (4-hydroxyphenyl) cyclohexane, 2,2 Bis (3-methyl-4-hydroxyphenyl) propane, bis (3,5-dimethyl-4-hydroxyphenyl) methane, 2,2-bis (3,5-dimethyl-4-hydroxyphenyl) propane 2,4-bis (3,5-dimethyl-4-hydroxyphenyl) -2-methylbutane and 1,1-bis (3,5-dimethyl-4-hydroxyphenyl) cyclohexane are suitable.
- Copolycarbonates preferred according to the invention contain bisphenol A and 1,1-bis (4-hydroxyphenyl) cyclohexane (bisphenol Z).
- Preferred mixing processes are processes 2 to 4, and mixing process 4 is particularly preferred.
- Rollers, kneading machines and screw machines are to be understood as suitable apparatus for the production of the mixtures according to the invention.
- Preferred apparatus are screw machines, in particular twin-screw machines.
- the production of the extrusion films from the blends according to the invention can be carried out in a known manner e.g. take place on normal, state-of-the-art, catchy three-zone screws, the deformation into foils being able to take place both via wide-slot nozzles to form foils, and also via blown film heads to blown foils.
- the extrusion films according to the invention have a particularly advantageous property profile, which makes them suitable, for example, for use in the electrical sector.
- the extrusion films according to the invention have high mechanical strength, high resistance to stress corrosion cracking in the heat and to organic liquids, high heat resistance and long-term heat resistance. In particular, they are characterized by their resistance to unsaturated polyester resin solutions.
- additives or fillers known in polycarbonate and polysulfone chemistry can also be added to the mixtures according to the invention.
- dyes such as dyes, pigments, mold release agents, stabilizers against the effects of moisture, heat and UV, lubricants, fillers, such as glass powder, quartz products, graphite, molybdenum sulfide, metal powder, powders of high-melting plastics, e.g. Polytetrafluoroethylene powder, natural fibers such as cotton, sisal and asbestos, furthermore glass fibers of all kinds, metal threads as well as fibers which are stable and do not noticeably damage the polycarbonates while they are in the melt of the polycarbonates.
- fillers such as glass powder, quartz products, graphite, molybdenum sulfide, metal powder, powders of high-melting plastics, e.g. Polytetrafluoroethylene powder, natural fibers such as cotton, sisal and asbestos, furthermore glass fibers of all kinds, metal threads as well as fibers which are stable and do not noticeably damage the polycarbonates while they are in the melt of the polycarbonates.
- a branched polyarylsulfone which is obtained by reacting 0.25 mol of 2,2-bis (4-hydroxyphenyl) propane with 0.0025 mol of 2,6-bis (2'-hydroxy-5'-methylbenzyl ) -4-methyl-phenol and 0.25375 mol of 4,4'-dichlorodiphenyl sulfone was produced (see US Pat. No. 3,960,815, Example 1), with a M w of 30,000 and 20 wt .-% of a polycarbonate based on bisphenol A with a M w of 95,000 are melted together in a 2-screw shaft, wherein the cylinder tempera - tures 340 ° C. The melt is pressed out as a strand. The strand is cooled and granulated.
- the granules obtained are melted on a single screw with a degassing zone, and the melt is expressed through a BreitschlitzdUse and drawn off via a chill-roll system to approximately 40 / um thick films.
- the property values obtained are listed in the table below.
- Example 1 Production of foils acc. Example 1, but using 70 wt .-% of a branched polyarylsulfone acc. Example 1 and 30 wt .-% of a bisphenol A polycarbonate, the M w is 75,000.
- the property values of the film obtained are listed in the table below.
- Example 1 From 80 wt .-% of a branched polysulfone acc.
- the polysulfone obtained is dissolved in methylene chloride, filtered and in an excess. poured quickly stirred methanol. The polysulfone separates in white flakes. It is filtered off and dried.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772735092 DE2735092A1 (de) | 1977-08-04 | 1977-08-04 | Abmischungen von verzweigtem polyarylsulfon-polycarbonat sowie ihre verwendung zur herstellung von extrusionsfolien |
| DE2735092 | 1977-08-04 | ||
| DE2755026 | 1977-12-09 | ||
| DE19772755026 DE2755026A1 (de) | 1977-12-09 | 1977-12-09 | Abmischungen von verzweigtem polyarylsulfon-polycarbonat sowie ihre verwendung zur herstellung von extrusionsfolien |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000732A1 true EP0000732A1 (fr) | 1979-02-21 |
| EP0000732B1 EP0000732B1 (fr) | 1980-07-23 |
Family
ID=25772463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100509A Expired EP0000732B1 (fr) | 1977-08-04 | 1978-07-26 | Mélanges de polyarylsulfones réticulées avec des polycarbonates et leur utilisation dans la préparation de feuilles extrudées |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4152367A (fr) |
| EP (1) | EP0000732B1 (fr) |
| JP (1) | JPS6040473B2 (fr) |
| DE (1) | DE2860069D1 (fr) |
| IT (1) | IT1106864B (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030326B1 (fr) * | 1979-12-04 | 1983-09-21 | Bayer Ag | Procédé de fabrication de feuilles coulées |
| EP0276285A4 (fr) * | 1986-08-07 | 1988-09-07 | Amoco Corp | Article façonne à partir d'un mélange d'un poly (aryle ether)et un polycarbonate. |
| EP0365916A1 (fr) * | 1988-10-24 | 1990-05-02 | Bayer Ag | Mélanges de polymères |
| DE4208341A1 (de) * | 1992-03-16 | 1993-09-23 | Basf Ag | Thermoplastische formmassen aus copolyarylenethern und polycarbonaten |
| EP0845501A1 (fr) * | 1996-11-29 | 1998-06-03 | Sumitomo Chemical Company, Limited | Composition de résine thermoplastique et article moulé |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1982000468A1 (fr) * | 1980-08-11 | 1982-02-18 | Gen Electric | Compositions de polycarbonate ignifuges |
| US4477637A (en) * | 1980-08-27 | 1984-10-16 | Mobay Chemical Corporation | Flame retardant alkylated polycarbonate compositions |
| US4358569A (en) * | 1980-12-31 | 1982-11-09 | General Electric Company | Blends of copolyester-carbonate with polysulfone |
| US5633331A (en) * | 1996-05-02 | 1997-05-27 | The Dow Chemical Company | Blends of polysulfone with diaryl fluorene carbonate polymer |
| US7754807B2 (en) * | 1999-04-20 | 2010-07-13 | Stratasys, Inc. | Soluble material and process for three-dimensional modeling |
| US6776602B2 (en) * | 1999-04-20 | 2004-08-17 | Stratasys, Inc. | Filament cassette and loading system |
| US7314591B2 (en) * | 2001-05-11 | 2008-01-01 | Stratasys, Inc. | Method for three-dimensional modeling |
| US6722872B1 (en) * | 1999-06-23 | 2004-04-20 | Stratasys, Inc. | High temperature modeling apparatus |
| DE10149871A1 (de) * | 2001-10-10 | 2003-04-17 | Basf Ag | Thermoplastische Formmassen mit verbesserter Schmelzstabilität auf Basis von Polyarylenethersulfonen |
| US6869559B2 (en) * | 2003-05-05 | 2005-03-22 | Stratasys, Inc. | Material and method for three-dimensional modeling |
| US7067608B2 (en) * | 2003-11-25 | 2006-06-27 | Xerox Corporation | Process for preparing branched polyarylene ethers |
| US7396895B2 (en) * | 2003-11-25 | 2008-07-08 | Xerox Corporation | Branched polyarylene ethers and processes for the preparation thereof |
| US7236166B2 (en) * | 2005-01-18 | 2007-06-26 | Stratasys, Inc. | High-resolution rapid manufacturing |
| US7341214B2 (en) * | 2005-06-30 | 2008-03-11 | Stratasys, Inc. | Cassette spool lock |
| US7384255B2 (en) * | 2005-07-01 | 2008-06-10 | Stratasys, Inc. | Rapid prototyping system with controlled material feedstock |
| DE102007044146A1 (de) * | 2007-09-12 | 2009-03-19 | Bayer Materialscience Ag | Thermoplast mit Metallkennzeichnungsplättchen |
| CN102066125A (zh) * | 2008-02-05 | 2011-05-18 | 拜尔技术服务有限责任公司 | 安全元件 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3365517A (en) * | 1965-04-08 | 1968-01-23 | Union Carbide Corp | Mixtures of polycarbonates and polyarylene polyethers |
| DE1932067C3 (de) * | 1969-06-25 | 1979-09-06 | Bayer Ag, 5090 Leverkusen | Polyaryläthersulfone und Verfahren zu ihrer Herstellung |
| US3652715A (en) * | 1969-07-01 | 1972-03-28 | Gen Electric | Curable polycarbonate compositions |
| US3631222A (en) * | 1970-01-02 | 1971-12-28 | Minnesota Mining & Mfg | Polyarylsulfone graft and block copolymers with chains of polyamide acid or polyimide |
| US3689464A (en) * | 1970-12-18 | 1972-09-05 | Gen Electric | Imido-substituted polyamide compositions |
| JPS5027061B1 (fr) * | 1971-03-08 | 1975-09-04 | ||
| DE2305413C2 (de) * | 1973-02-03 | 1982-05-13 | Bayer Ag, 5090 Leverkusen | Verzweigte aromatische Polyaryläthersulfone |
-
1978
- 1978-07-25 US US05/927,808 patent/US4152367A/en not_active Expired - Lifetime
- 1978-07-26 EP EP78100509A patent/EP0000732B1/fr not_active Expired
- 1978-07-26 DE DE7878100509T patent/DE2860069D1/de not_active Expired
- 1978-08-02 IT IT50576/78A patent/IT1106864B/it active
- 1978-08-02 JP JP53093720A patent/JPS6040473B2/ja not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| Keine Entgegenhaltungen. * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030326B1 (fr) * | 1979-12-04 | 1983-09-21 | Bayer Ag | Procédé de fabrication de feuilles coulées |
| EP0276285A4 (fr) * | 1986-08-07 | 1988-09-07 | Amoco Corp | Article façonne à partir d'un mélange d'un poly (aryle ether)et un polycarbonate. |
| EP0365916A1 (fr) * | 1988-10-24 | 1990-05-02 | Bayer Ag | Mélanges de polymères |
| DE4208341A1 (de) * | 1992-03-16 | 1993-09-23 | Basf Ag | Thermoplastische formmassen aus copolyarylenethern und polycarbonaten |
| EP0845501A1 (fr) * | 1996-11-29 | 1998-06-03 | Sumitomo Chemical Company, Limited | Composition de résine thermoplastique et article moulé |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2860069D1 (en) | 1980-11-13 |
| JPS6040473B2 (ja) | 1985-09-11 |
| IT1106864B (it) | 1985-11-18 |
| US4152367A (en) | 1979-05-01 |
| IT7850576A0 (it) | 1978-08-02 |
| JPS5428362A (en) | 1979-03-02 |
| EP0000732B1 (fr) | 1980-07-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0000732A1 (fr) | Mélanges de polyarylsulfones réticulées avec des polycarbonates et leur utilisation dans la préparation de feuilles extrudées | |
| DE2503336C2 (de) | Polycarbonat-Formmassen | |
| EP0374656B1 (fr) | Polycarbonates à partir de bisphénols alcoylcyclohexylidéniques | |
| EP0087038B1 (fr) | Utilisation de polysulfides de phénylène à couleur claire en mélanges avec des polycarbonates thermoplastiques et/ou des polyesters thermoplastiques | |
| DE69505305T2 (de) | Copolycarbonat mit verbesserter Niedertemperatur-Schlagzähigkeit | |
| DE2500092A1 (de) | Verzweigte, hochmolekulare, thermoplastische polycarbonate | |
| DE4424105A1 (de) | Epoxigruppen enthaltende Siloxane und ihre Mischungen mit Polycarbonaten | |
| EP0040863A1 (fr) | Mélanges de polycarbonates à combustion retardée | |
| EP0000733B1 (fr) | Mélanges comprenant une polyarylsulfone linéaire et un polycarbonate et leur utilisation dans la préparation de feuilles extrudées | |
| DE2615038C3 (de) | l,lA4,6-Pentamethyl-3-(3^-dimethyl-4-hydroxyphenyl)- indan-5-ol - Polycarbonate | |
| EP0436186A2 (fr) | Masses de moulage de polycarbonate ayant une stabilité dimensionnelle à chaud et une bonne transformabilité, résistant à la chaleur | |
| DE60118394T2 (de) | Transparente Zusammensetzung enthaltend ein Polycarbonat und ein Methylmethacrylat-Copolymer | |
| WO2001005870A1 (fr) | Polycarbonates contenant des silicones a fonction d'ester d'acide aspartique | |
| EP0120296B1 (fr) | Masses à mouler difficilement inflammables, transparentes, de poly(aryléther-arylsulfone), procédé pour leur fabrication ainsi que leur utilisation | |
| DE19501501A1 (de) | Mischungen aus aromatischen Polycarbonaten und epoxyfunktionellen Terpolymeren | |
| EP0374623B1 (fr) | Polycarbonates à partir de biphénols cyclohexylidéniques polysubstitués | |
| EP0014412B1 (fr) | Compositions thermoplastiques et procédé pour leur préparation | |
| EP0472064A2 (fr) | Mélanges ternaires | |
| EP0423562B1 (fr) | Polycarbonates ayant une stabilité dimensionnelle à chaud plus élevée | |
| DE2735092A1 (de) | Abmischungen von verzweigtem polyarylsulfon-polycarbonat sowie ihre verwendung zur herstellung von extrusionsfolien | |
| EP0099990A1 (fr) | Procédé de préparation de polycarbonates renfermant des groupements terminaux N-alkylperfluoro alkylsulfonamides | |
| DE3906919A1 (de) | Flammwidrige polydiorganosiloxan-polycarbonat-blockcopolymere | |
| DE2735144A1 (de) | Polyarylsulfon-polycarbonat-abmischungen und ihre verwendung zur herstellung von extrusionsfolien | |
| EP0374630A2 (fr) | Polycarbonates à partir de bisphénols cyclohexylidéniques | |
| EP0040746B1 (fr) | Polycarbonate transparent, ignifuge |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed | ||
| AK | Designated contracting states |
Designated state(s): DE FR GB NL |
|
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| AK | Designated contracting states |
Designated state(s): DE FR GB NL |
|
| REF | Corresponds to: |
Ref document number: 2860069 Country of ref document: DE Date of ref document: 19801113 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19910619 Year of fee payment: 14 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19910705 Year of fee payment: 14 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 19910712 Year of fee payment: 14 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19910731 Year of fee payment: 14 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Effective date: 19920726 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Effective date: 19930201 |
|
| NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee | ||
| GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 19920726 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Effective date: 19930331 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19930401 |
|
| REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |
|
| PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |