DE2246106C2 - s-Triazinringe enthaltende hochmolekulare Polycarbonate - Google Patents
s-Triazinringe enthaltende hochmolekulare PolycarbonateInfo
- Publication number
- DE2246106C2 DE2246106C2 DE2246106A DE2246106A DE2246106C2 DE 2246106 C2 DE2246106 C2 DE 2246106C2 DE 2246106 A DE2246106 A DE 2246106A DE 2246106 A DE2246106 A DE 2246106A DE 2246106 C2 DE2246106 C2 DE 2246106C2
- Authority
- DE
- Germany
- Prior art keywords
- triazine
- mol
- carbon atoms
- dichloro
- radical
- 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.)
- Expired
Links
- 239000004417 polycarbonate Substances 0.000 title claims description 75
- 229920000515 polycarbonate Polymers 0.000 title claims description 74
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 title claims description 35
- -1 p-phenylene radical Chemical class 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 119
- 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 96
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 45
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 42
- 239000000460 chlorine Substances 0.000 description 36
- 238000004519 manufacturing process Methods 0.000 description 35
- 239000000203 mixture Substances 0.000 description 31
- 239000001294 propane Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- UIKAQTBBQJSDQE-UHFFFAOYSA-N 4,6-dichloro-n,n-diphenyl-1,3,5-triazin-2-amine Chemical compound ClC1=NC(Cl)=NC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 UIKAQTBBQJSDQE-UHFFFAOYSA-N 0.000 description 17
- 238000010992 reflux Methods 0.000 description 15
- 239000012071 phase Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 238000007710 freezing Methods 0.000 description 10
- 230000008014 freezing Effects 0.000 description 10
- 229930185605 Bisphenol Natural products 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 8
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 7
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 241000251730 Chondrichthyes Species 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001447 alkali salts Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- 238000009864 tensile test Methods 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UIGMDMOGAQFIQT-UHFFFAOYSA-N 2,4-dichloro-6-(2,6-dimethylphenoxy)-1,3,5-triazine Chemical compound CC1=CC=CC(C)=C1OC1=NC(Cl)=NC(Cl)=N1 UIGMDMOGAQFIQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical compound ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 description 2
- MUEJUOUFUTUSED-UHFFFAOYSA-N 2,4-dichloro-6-piperidin-1-yl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(N2CCCCC2)=N1 MUEJUOUFUTUSED-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- MCLXKFUCPVGZEN-UHFFFAOYSA-N 4,6-dichloro-1,3,5-triazin-2-amine Chemical compound NC1=NC(Cl)=NC(Cl)=N1 MCLXKFUCPVGZEN-UHFFFAOYSA-N 0.000 description 2
- HYWCPNMPNFJCMD-UHFFFAOYSA-N 4,6-dichloro-n,n-diethyl-1,3,5-triazin-2-amine Chemical compound CCN(CC)C1=NC(Cl)=NC(Cl)=N1 HYWCPNMPNFJCMD-UHFFFAOYSA-N 0.000 description 2
- SACFASUHQGNXOD-UHFFFAOYSA-N 4,6-dichloro-n-phenyl-1,3,5-triazin-2-amine Chemical compound ClC1=NC(Cl)=NC(NC=2C=CC=CC=2)=N1 SACFASUHQGNXOD-UHFFFAOYSA-N 0.000 description 2
- UQAMDAUJTXFNAD-UHFFFAOYSA-N 4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine Chemical compound ClC1=NC(Cl)=NC(N2CCOCC2)=N1 UQAMDAUJTXFNAD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 230000016507 interphase Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 1
- XNENFVLWGQMFFY-UHFFFAOYSA-N 2,4-dichloro-6-(2-methylphenoxy)-1,3,5-triazine Chemical compound CC1=CC=CC=C1OC1=NC(Cl)=NC(Cl)=N1 XNENFVLWGQMFFY-UHFFFAOYSA-N 0.000 description 1
- OSBNIDJUMJLHPX-UHFFFAOYSA-N 2,4-dichloro-6-(3-methylphenoxy)-1,3,5-triazine Chemical compound CC1=CC=CC(OC=2N=C(Cl)N=C(Cl)N=2)=C1 OSBNIDJUMJLHPX-UHFFFAOYSA-N 0.000 description 1
- YZMWCUDWOQOYKY-UHFFFAOYSA-N 2,4-dichloro-6-(4-methylphenoxy)-1,3,5-triazine Chemical compound C1=CC(C)=CC=C1OC1=NC(Cl)=NC(Cl)=N1 YZMWCUDWOQOYKY-UHFFFAOYSA-N 0.000 description 1
- RNUNMDBBXRZXFA-UHFFFAOYSA-N 2,4-dichloro-6-cyclohexyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C2CCCCC2)=N1 RNUNMDBBXRZXFA-UHFFFAOYSA-N 0.000 description 1
- BFPUNEGIVJHEFS-UHFFFAOYSA-N 2,4-dichloro-6-cyclohexyloxy-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(OC2CCCCC2)=N1 BFPUNEGIVJHEFS-UHFFFAOYSA-N 0.000 description 1
- HMSBXLTWCMFPDZ-UHFFFAOYSA-N 2,4-dichloro-6-ethoxy-1,3,5-triazine Chemical compound CCOC1=NC(Cl)=NC(Cl)=N1 HMSBXLTWCMFPDZ-UHFFFAOYSA-N 0.000 description 1
- ZCZJJJXYLSCYII-UHFFFAOYSA-N 2,4-dichloro-6-ethylsulfanyl-1,3,5-triazine Chemical compound CCSC1=NC(Cl)=NC(Cl)=N1 ZCZJJJXYLSCYII-UHFFFAOYSA-N 0.000 description 1
- JKAPWXKZLYJQJJ-UHFFFAOYSA-N 2,4-dichloro-6-methoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(Cl)=N1 JKAPWXKZLYJQJJ-UHFFFAOYSA-N 0.000 description 1
- BFUGAHPTVMZLAC-UHFFFAOYSA-N 2,4-dichloro-6-methyl-1,3,5-triazine Chemical compound CC1=NC(Cl)=NC(Cl)=N1 BFUGAHPTVMZLAC-UHFFFAOYSA-N 0.000 description 1
- MWPZLWRHHPWTFS-UHFFFAOYSA-N 2,4-dichloro-6-methylsulfanyl-1,3,5-triazine Chemical compound CSC1=NC(Cl)=NC(Cl)=N1 MWPZLWRHHPWTFS-UHFFFAOYSA-N 0.000 description 1
- ACMVCGAZNQJQFJ-UHFFFAOYSA-N 2,4-dichloro-6-phenoxy-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(OC=2C=CC=CC=2)=N1 ACMVCGAZNQJQFJ-UHFFFAOYSA-N 0.000 description 1
- AMEVJOWOWQPPJQ-UHFFFAOYSA-N 2,4-dichloro-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=CC=CC=2)=N1 AMEVJOWOWQPPJQ-UHFFFAOYSA-N 0.000 description 1
- AHKWZLWMIZHTLU-UHFFFAOYSA-N 2,4-dichloro-6-phenylsulfanyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(SC=2C=CC=CC=2)=N1 AHKWZLWMIZHTLU-UHFFFAOYSA-N 0.000 description 1
- PFMRZZXGXJJZHY-UHFFFAOYSA-N 2,4-dichloro-6-propan-2-yloxy-1,3,5-triazine Chemical compound CC(C)OC1=NC(Cl)=NC(Cl)=N1 PFMRZZXGXJJZHY-UHFFFAOYSA-N 0.000 description 1
- BHWWVJLPSHEQBF-UHFFFAOYSA-N 2,4-dichloro-6-pyrrolidin-1-yl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(N2CCCC2)=N1 BHWWVJLPSHEQBF-UHFFFAOYSA-N 0.000 description 1
- HRJUNDFYEFTHIW-UHFFFAOYSA-N 2-(4-tert-butylphenoxy)-4,6-dichloro-1,3,5-triazine Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1=NC(Cl)=NC(Cl)=N1 HRJUNDFYEFTHIW-UHFFFAOYSA-N 0.000 description 1
- KYGLCUAXJICESS-UHFFFAOYSA-N 2-[2,3-di(propan-2-yl)phenyl]phenol Chemical compound CC(C)C1=CC=CC(C=2C(=CC=CC=2)O)=C1C(C)C KYGLCUAXJICESS-UHFFFAOYSA-N 0.000 description 1
- FRCJZVRRIQZXBL-UHFFFAOYSA-N 2-butylsulfanyl-4,6-dichloro-1,3,5-triazine Chemical compound CCCCSC1=NC(Cl)=NC(Cl)=N1 FRCJZVRRIQZXBL-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
- WFZXIHBXPFGXBN-UHFFFAOYSA-N 4,6-dichloro-2-methyl-N-phenyl-1H-triazin-5-amine Chemical compound CN1NC(=C(C(=N1)Cl)NC1=CC=CC=C1)Cl WFZXIHBXPFGXBN-UHFFFAOYSA-N 0.000 description 1
- WUIDKVCYKAPOKI-UHFFFAOYSA-N 4,6-dichloro-2-methylsulfanyl-1h-triazine Chemical compound CSN1NC(Cl)=CC(Cl)=N1 WUIDKVCYKAPOKI-UHFFFAOYSA-N 0.000 description 1
- OPFSBBBDOCTPCC-UHFFFAOYSA-N 4,6-dichloro-n-(2-methylphenyl)-1,3,5-triazin-2-amine Chemical compound CC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 OPFSBBBDOCTPCC-UHFFFAOYSA-N 0.000 description 1
- PFXOXPWDWFPCOT-UHFFFAOYSA-N 4,6-dichloro-n-(3-methylphenyl)-1,3,5-triazin-2-amine Chemical compound CC1=CC=CC(NC=2N=C(Cl)N=C(Cl)N=2)=C1 PFXOXPWDWFPCOT-UHFFFAOYSA-N 0.000 description 1
- TYGVZWLFENCCCW-UHFFFAOYSA-N 4,6-dichloro-n-(4-methylphenyl)-1,3,5-triazin-2-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 TYGVZWLFENCCCW-UHFFFAOYSA-N 0.000 description 1
- CWKXMUIHCFFUSG-UHFFFAOYSA-N 4,6-dichloro-n-dodecyl-1,3,5-triazin-2-amine Chemical compound CCCCCCCCCCCCNC1=NC(Cl)=NC(Cl)=N1 CWKXMUIHCFFUSG-UHFFFAOYSA-N 0.000 description 1
- ACAHVXOSWOUZAB-UHFFFAOYSA-N 4,6-dichloro-n-ethyl-1,3,5-triazin-2-amine Chemical compound CCNC1=NC(Cl)=NC(Cl)=N1 ACAHVXOSWOUZAB-UHFFFAOYSA-N 0.000 description 1
- QEIGXPSVULXMGM-UHFFFAOYSA-N 4,6-dichloro-n-hexyl-1,3,5-triazin-2-amine Chemical compound CCCCCCNC1=NC(Cl)=NC(Cl)=N1 QEIGXPSVULXMGM-UHFFFAOYSA-N 0.000 description 1
- QRTBWWIIFMMESL-UHFFFAOYSA-N 4,6-dichloro-n-methyl-1,3,5-triazin-2-amine Chemical compound CNC1=NC(Cl)=NC(Cl)=N1 QRTBWWIIFMMESL-UHFFFAOYSA-N 0.000 description 1
- POWUTOPVEGZOSU-UHFFFAOYSA-N 4,6-dichloro-n-octadecyl-1,3,5-triazin-2-amine Chemical compound CCCCCCCCCCCCCCCCCCNC1=NC(Cl)=NC(Cl)=N1 POWUTOPVEGZOSU-UHFFFAOYSA-N 0.000 description 1
- MXCZYRJBEZWBSA-UHFFFAOYSA-N 4,6-dichloro-n-prop-2-enyl-1,3,5-triazin-2-amine Chemical compound ClC1=NC(Cl)=NC(NCC=C)=N1 MXCZYRJBEZWBSA-UHFFFAOYSA-N 0.000 description 1
- JDAPQMINSZDTBM-UHFFFAOYSA-N 4,6-dichloro-n-propan-2-yl-1,3,5-triazin-2-amine Chemical compound CC(C)NC1=NC(Cl)=NC(Cl)=N1 JDAPQMINSZDTBM-UHFFFAOYSA-N 0.000 description 1
- JXMNIFBDZUCJHU-UHFFFAOYSA-N 4,6-dichloro-n-propyl-1,3,5-triazin-2-amine Chemical compound CCCNC1=NC(Cl)=NC(Cl)=N1 JXMNIFBDZUCJHU-UHFFFAOYSA-N 0.000 description 1
- WICKKKBLCOHNLT-UHFFFAOYSA-N 4-(4,6-dichloro-1,3,5-triazin-2-yl)thiomorpholine Chemical compound ClC1=NC(Cl)=NC(N2CCSCC2)=N1 WICKKKBLCOHNLT-UHFFFAOYSA-N 0.000 description 1
- WYCCBNGHFYBVOM-UHFFFAOYSA-N 4-(4-chloro-6-morpholin-4-yl-1,3,5-triazin-2-yl)morpholine Chemical compound N=1C(Cl)=NC(N2CCOCC2)=NC=1N1CCOCC1 WYCCBNGHFYBVOM-UHFFFAOYSA-N 0.000 description 1
- 101100007300 Caenorhabditis elegans coq-2 gene Proteins 0.000 description 1
- UKOWTAIHIAMFQD-UHFFFAOYSA-N ClC(C=C(N1)Cl)=NN1N(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound ClC(C=C(N1)Cl)=NN1N(C1=CC=CC=C1)C1=CC=CC=C1 UKOWTAIHIAMFQD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- WWACVBYOEOGPPO-UHFFFAOYSA-N N,N-diphenyltriazin-4-amine Chemical compound C1(=CC=CC=C1)N(C1=CC=NN=N1)C1=CC=CC=C1 WWACVBYOEOGPPO-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QFEAITOMWXXDME-UHFFFAOYSA-N n-benzyl-4,6-dichloro-1,3,5-triazin-2-amine Chemical compound ClC1=NC(Cl)=NC(NCC=2C=CC=CC=2)=N1 QFEAITOMWXXDME-UHFFFAOYSA-N 0.000 description 1
- ASPFUMMXOGOLNI-UHFFFAOYSA-N n-tert-butyl-4,6-dichloro-1,3,5-triazin-2-amine Chemical compound CC(C)(C)NC1=NC(Cl)=NC(Cl)=N1 ASPFUMMXOGOLNI-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
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)
- Fireproofing Substances (AREA)
- Polyesters Or Polycarbonates (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2246106A DE2246106C2 (de) | 1972-09-20 | 1972-09-20 | s-Triazinringe enthaltende hochmolekulare Polycarbonate |
| CA181,152A CA1028095A (en) | 1972-09-20 | 1973-09-12 | High molecular polycarbonates containing s-triazine rings |
| US397502A US3894991A (en) | 1972-09-20 | 1973-09-14 | High molecular polycarbonates containing s-triazine rings |
| JP10463273A JPS5533736B2 (en:Method) | 1972-09-20 | 1973-09-18 | |
| IT52571/73A IT1000072B (it) | 1972-09-20 | 1973-09-18 | Policarbonati di alto peso moleco lare contenenti anelli di s triazi na e procedimento per produrli |
| GB4397373A GB1430281A (en) | 1972-09-20 | 1973-09-19 | High molecular weight polycarbonates containing s-triazine rings |
| BE135829A BE805069A (fr) | 1972-09-20 | 1973-09-20 | Polycarbonates a haut poids moleculaire contenant des cycles s-triaziniques |
| FR7333816A FR2200308B1 (en:Method) | 1972-09-20 | 1973-09-20 | |
| NL7312996A NL7312996A (en:Method) | 1972-09-20 | 1973-09-20 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2246106A DE2246106C2 (de) | 1972-09-20 | 1972-09-20 | s-Triazinringe enthaltende hochmolekulare Polycarbonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2246106A1 DE2246106A1 (de) | 1974-03-28 |
| DE2246106C2 true DE2246106C2 (de) | 1983-02-24 |
Family
ID=5856834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2246106A Expired DE2246106C2 (de) | 1972-09-20 | 1972-09-20 | s-Triazinringe enthaltende hochmolekulare Polycarbonate |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3894991A (en:Method) |
| JP (1) | JPS5533736B2 (en:Method) |
| BE (1) | BE805069A (en:Method) |
| CA (1) | CA1028095A (en:Method) |
| DE (1) | DE2246106C2 (en:Method) |
| FR (1) | FR2200308B1 (en:Method) |
| GB (1) | GB1430281A (en:Method) |
| IT (1) | IT1000072B (en:Method) |
| NL (1) | NL7312996A (en:Method) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2419767A1 (de) * | 1974-04-24 | 1975-12-11 | Bayer Ag | Thermoplastische formmassen aus triazinhaltigen polykondensaten und pfropfpolymerisaten |
| JPS51150598A (en) * | 1975-06-19 | 1976-12-24 | Mitsubishi Gas Chem Co Inc | Preparation of crosslinked polycarbonate |
| IT1052501B (it) * | 1975-12-04 | 1981-07-20 | Chimosa Chimica Organica Spa | Composti politriazinici utilizzabili per la stabilizzazione di polimeri sintetici e procedimento per la loro preparazione |
| US4737570A (en) * | 1983-06-20 | 1988-04-12 | Eastman Kodak Company | Polycarbonate having tertiary amine acid addition salt moieties |
| US4608310A (en) * | 1983-06-20 | 1986-08-26 | Eastman Kodak Company | Polycarbonate, latex compositions comprising such |
| IT1207057B (it) * | 1985-07-10 | 1989-05-17 | Sassari A | Policarbonati ramificati contenenti 2,4,6-tris(4'-idrossiaril)-ammino-s-triazine. |
| US4680370A (en) * | 1985-09-30 | 1987-07-14 | The Dow Chemical Company | Branched polycarbonate composition from tris(hydroxyaryl)phosphorus compound |
| US4855392A (en) * | 1987-08-31 | 1989-08-08 | Eastman Kodak Company | Photographic element comprising polycarbonate having tertiary amine acid addition salt |
| US4824902A (en) * | 1987-08-31 | 1989-04-25 | Eastman Kodak Company | Latex composition comprising polycarbonate having tertiary amine acid addition moiety |
| US5030693A (en) * | 1990-03-19 | 1991-07-09 | General Electric Company | Copolymer compositions prepared from triazine derivatives of polycarbonates |
| US20030078347A1 (en) * | 2001-08-28 | 2003-04-24 | General Electric Company | Triazine compounds, polymers comprising triazine structural units, and method |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1495141A1 (de) * | 1963-09-14 | 1969-03-27 | Basf Ag | Verfahren zum Herstellen von Triazinringe enthaltenden Polymeren |
| US3525712A (en) * | 1965-09-01 | 1970-08-25 | Gen Electric | Process for preparing thermoplastic polycarbonates |
| US3541049A (en) * | 1969-08-21 | 1970-11-17 | Mobay Chemical Corp | Cyanuric chloride branched polycarbonates |
-
1972
- 1972-09-20 DE DE2246106A patent/DE2246106C2/de not_active Expired
-
1973
- 1973-09-12 CA CA181,152A patent/CA1028095A/en not_active Expired
- 1973-09-14 US US397502A patent/US3894991A/en not_active Expired - Lifetime
- 1973-09-18 IT IT52571/73A patent/IT1000072B/it active
- 1973-09-18 JP JP10463273A patent/JPS5533736B2/ja not_active Expired
- 1973-09-19 GB GB4397373A patent/GB1430281A/en not_active Expired
- 1973-09-20 FR FR7333816A patent/FR2200308B1/fr not_active Expired
- 1973-09-20 NL NL7312996A patent/NL7312996A/xx unknown
- 1973-09-20 BE BE135829A patent/BE805069A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3894991A (en) | 1975-07-15 |
| JPS4971087A (en:Method) | 1974-07-09 |
| DE2246106A1 (de) | 1974-03-28 |
| NL7312996A (en:Method) | 1974-03-22 |
| JPS5533736B2 (en:Method) | 1980-09-02 |
| FR2200308B1 (en:Method) | 1977-03-11 |
| IT1000072B (it) | 1976-03-30 |
| CA1028095A (en) | 1978-03-14 |
| FR2200308A1 (en:Method) | 1974-04-19 |
| GB1430281A (en) | 1976-03-31 |
| BE805069A (fr) | 1974-03-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |