DE2709419A1 - Farbstabilisierte halogenbisphenolaethylen-polycarbonate - Google Patents
Farbstabilisierte halogenbisphenolaethylen-polycarbonateInfo
- Publication number
- DE2709419A1 DE2709419A1 DE19772709419 DE2709419A DE2709419A1 DE 2709419 A1 DE2709419 A1 DE 2709419A1 DE 19772709419 DE19772709419 DE 19772709419 DE 2709419 A DE2709419 A DE 2709419A DE 2709419 A1 DE2709419 A1 DE 2709419A1
- Authority
- DE
- Germany
- Prior art keywords
- deep
- hydrogen
- value
- polycarbonate
- ethylene
- 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.)
- Withdrawn
Links
- 229920000515 polycarbonate Polymers 0.000 title claims description 71
- 239000004417 polycarbonate Substances 0.000 title claims description 70
- -1 aliphatic epoxides Chemical class 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 25
- 239000005977 Ethylene Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000003381 stabilizer Substances 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 150000002118 epoxides Chemical class 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052788 barium Inorganic materials 0.000 claims description 12
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052793 cadmium Inorganic materials 0.000 claims description 12
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 238000000354 decomposition reaction Methods 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 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 7
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 3
- 229930185605 Bisphenol Natural products 0.000 claims 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 150000002989 phenols Chemical class 0.000 description 15
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000001294 propane Substances 0.000 description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000000087 stabilizing effect Effects 0.000 description 5
- RKWLLKDPLBNLOK-UHFFFAOYSA-N OC1(C=CC=CC1)C(C1(C=CC=CC1)O)=C(Cl)Cl Chemical group OC1(C=CC=CC1)C(C1(C=CC=CC1)O)=C(Cl)Cl RKWLLKDPLBNLOK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical group C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QUWGNYVHIGWIKU-UHFFFAOYSA-N carbonic acid;styrene Chemical group OC(O)=O.C=CC1=CC=CC=C1 QUWGNYVHIGWIKU-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- XCPFSALHURPPJE-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XCPFSALHURPPJE-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- VDWZARQSXFKCPV-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid 2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)CO.CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O VDWZARQSXFKCPV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical class O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229940050390 benzoate Drugs 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 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
- 229940106691 bisphenol a Drugs 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- PFWVNWPDTPFDTR-UHFFFAOYSA-N (2,3-dipropylphenyl) dihydrogen phosphite Chemical compound CCCC1=CC=CC(OP(O)O)=C1CCC PFWVNWPDTPFDTR-UHFFFAOYSA-N 0.000 description 1
- GYBMIYGFXBQLQF-UHFFFAOYSA-N (3,5-ditert-butyl-1-hydroxycyclohexa-2,4-dien-1-yl) acetate Chemical compound CC(=O)OC1(O)CC(C(C)(C)C)=CC(C(C)(C)C)=C1 GYBMIYGFXBQLQF-UHFFFAOYSA-N 0.000 description 1
- IFANDYITEICIKO-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxy-2-octadecylphenyl) acetate Chemical compound CCCCCCCCCCCCCCCCCCC1=C(OC(C)=O)C=C(C(C)(C)C)C(O)=C1C(C)(C)C IFANDYITEICIKO-UHFFFAOYSA-N 0.000 description 1
- YCAIEJOMDICRGU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl) 2-methylpropanoate Chemical compound CC(C)C(=O)OC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 YCAIEJOMDICRGU-UHFFFAOYSA-N 0.000 description 1
- AWCHONBUIHCDMW-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl) acetate Chemical compound CC(=O)OC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 AWCHONBUIHCDMW-UHFFFAOYSA-N 0.000 description 1
- LFOZRUYRWISVSO-UHFFFAOYSA-N 1,2-dimethyl-6-(4-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)cyclohexane-1-carboxylic acid Chemical compound O1C2CC(C(CC21)C)C2C(C(CCC2)C)(C(=O)O)C LFOZRUYRWISVSO-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- DVAXOVZBOHTDAJ-UHFFFAOYSA-N 1-ethenylcyclohexa-2,4-dien-1-ol Chemical group C=CC1(O)CC=CC=C1 DVAXOVZBOHTDAJ-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- GMKFVAQTCWISMX-UHFFFAOYSA-N 12,12-diphenyldodecyl dihydrogen phosphite Chemical compound C=1C=CC=CC=1C(CCCCCCCCCCCOP(O)O)C1=CC=CC=C1 GMKFVAQTCWISMX-UHFFFAOYSA-N 0.000 description 1
- CBQXCOJLWWSCQI-UHFFFAOYSA-N 2,3,6-trichloro-4-[2,2-dichloro-1-(2,3,5-trichloro-4-hydroxyphenyl)ethenyl]phenol Chemical group ClC1=C(Cl)C(O)=C(Cl)C=C1C(=C(Cl)Cl)C1=CC(Cl)=C(O)C(Cl)=C1Cl CBQXCOJLWWSCQI-UHFFFAOYSA-N 0.000 description 1
- JGLRZMXYGZLAEN-UHFFFAOYSA-N 2,3-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]butyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1CCC(=O)OCC(OC(=O)CCC=1C=C(C(O)=C(C=1)C(C)(C)C)C(C)(C)C)C(C)OC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 JGLRZMXYGZLAEN-UHFFFAOYSA-N 0.000 description 1
- PNZLJNVUTPFUIE-UHFFFAOYSA-N 2,3-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]propyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)OC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 PNZLJNVUTPFUIE-UHFFFAOYSA-N 0.000 description 1
- SJSZGSQQPBNXPY-UHFFFAOYSA-N 2,3-dibromo-4-[2-bromo-1-(2,3-dibromo-4-hydroxyphenyl)ethenyl]phenol Chemical group BrC1=C(Br)C(O)=CC=C1C(=CBr)C1=CC=C(O)C(Br)=C1Br SJSZGSQQPBNXPY-UHFFFAOYSA-N 0.000 description 1
- ZFTQHXQXEAKZRD-UHFFFAOYSA-N 2,5-dibromo-4-[2,2-dibromo-1-(2,5-dibromo-4-hydroxyphenyl)ethenyl]phenol Chemical group C1=C(Br)C(O)=CC(Br)=C1C(=C(Br)Br)C1=CC(Br)=C(O)C=C1Br ZFTQHXQXEAKZRD-UHFFFAOYSA-N 0.000 description 1
- UZRXVQQOYCIJJA-UHFFFAOYSA-N 2,5-dibromo-4-[2-chloro-1-(2,5-dibromo-4-hydroxyphenyl)ethenyl]phenol Chemical group C1=C(Br)C(O)=CC(Br)=C1C(=CCl)C1=CC(Br)=C(O)C=C1Br UZRXVQQOYCIJJA-UHFFFAOYSA-N 0.000 description 1
- VFVQBJRXXCJYIK-UHFFFAOYSA-N 2,6-dibromo-4-[2,2-dichloro-1-(3,5-dibromo-4-hydroxyphenyl)ethenyl]phenol Chemical group C1=C(Br)C(O)=C(Br)C=C1C(=C(Cl)Cl)C1=CC(Br)=C(O)C(Br)=C1 VFVQBJRXXCJYIK-UHFFFAOYSA-N 0.000 description 1
- JHVGTIVDWHIVQW-UHFFFAOYSA-N 2,6-dichloro-4-[2,2-dichloro-1-(3,5-dichloro-4-hydroxyphenyl)ethenyl]phenol Chemical group C1=C(Cl)C(O)=C(Cl)C=C1C(=C(Cl)Cl)C1=CC(Cl)=C(O)C(Cl)=C1 JHVGTIVDWHIVQW-UHFFFAOYSA-N 0.000 description 1
- MLSPENRYOBVDKN-UHFFFAOYSA-N 2,6-ditert-butyl-1-methylcyclohexa-2,4-dien-1-ol Chemical compound CC(C)(C)C1C=CC=C(C(C)(C)C)C1(C)O MLSPENRYOBVDKN-UHFFFAOYSA-N 0.000 description 1
- IJKFGMGAWRWWKN-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)-3-dodecylbenzoic acid Chemical compound CCCCCCCCCCCCC1=CC=CC(C(O)=O)=C1C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 IJKFGMGAWRWWKN-UHFFFAOYSA-N 0.000 description 1
- DIQZGCCQHMIOLR-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enoic acid;methane Chemical compound C.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O DIQZGCCQHMIOLR-UHFFFAOYSA-N 0.000 description 1
- RPJLPEUNIGUTJT-UHFFFAOYSA-N 2-[2-(3,5-ditert-butyl-4-hydroxyphenyl)acetyl]oxyethyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)acetate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC(=O)OCCOC(=O)CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 RPJLPEUNIGUTJT-UHFFFAOYSA-N 0.000 description 1
- BBDGBZSSDZTJCW-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethoxy]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCOCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BBDGBZSSDZTJCW-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- RNVAPPWJCZTWQL-UHFFFAOYSA-N octadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RNVAPPWJCZTWQL-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-M phenyl carbonate Chemical compound [O-]C(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-M 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/668,858 US4118370A (en) | 1976-03-22 | 1976-03-22 | Color-stabilized halobisphenol ethylene polycarbonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2709419A1 true DE2709419A1 (de) | 1977-10-06 |
Family
ID=24684021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772709419 Withdrawn DE2709419A1 (de) | 1976-03-22 | 1977-03-04 | Farbstabilisierte halogenbisphenolaethylen-polycarbonate |
Country Status (14)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4294954A (en) * | 1979-12-13 | 1981-10-13 | General Electric Company | Polycarbonate copolymers |
| NL8302686A (nl) * | 1983-07-28 | 1983-11-01 | Gen Electric | Informatiedrager voor optisch uitleesbare informatie. |
| US4647288A (en) * | 1985-08-30 | 1987-03-03 | Union Oil Company Of California | Hydrocarbon fuel composition containing orthoester and cyclic aldehyde polymer |
| US5037889A (en) * | 1986-12-23 | 1991-08-06 | General Electric Company | Resin blends exhibiting improved impact properties |
| KR900701959A (ko) * | 1988-08-31 | 1990-12-05 | 호이만, 쉬틀러 | 열색 혼합물 |
| US5225526A (en) * | 1989-08-17 | 1993-07-06 | Asahi Kasei Kogyo Kabushiki Kaisha | Stabilized aromatic polycarbonate composition and process for producing same |
| JPH08118394A (ja) * | 1994-10-27 | 1996-05-14 | Fuji Photo Film Co Ltd | 写真感光材料用射出成形品及びその成形方法並びにそれを用いた包装体 |
| US6448334B1 (en) * | 2000-12-19 | 2002-09-10 | General Electric Company | Translucent polycarbonate composition, method for preparation thereof, and articles derived therefrom |
| US7940605B2 (en) * | 2005-04-29 | 2011-05-10 | Prasidiux, Llc | Stimulus indicating device employing polymer gels |
| US9182292B2 (en) | 2005-04-29 | 2015-11-10 | Prasidiux, Llc | Stimulus indicating device employing polymer gels |
| WO2006119141A2 (en) * | 2005-04-29 | 2006-11-09 | Ambrozy Rel S | Stimulus indication employing polymer gels |
| US8077554B2 (en) | 2005-04-29 | 2011-12-13 | Ambrozy Rel S | Stimulus indicating device employing polymer gels |
| US8166906B2 (en) * | 2005-04-29 | 2012-05-01 | Ambrozy Rel S | Stimulus indicating device employing polymer gels |
| US20120032117A1 (en) | 2005-04-29 | 2012-02-09 | Ambrozy Rel S | Stimulus indicating device employing polymer gels |
| US7297381B2 (en) * | 2005-05-20 | 2007-11-20 | General Electric Company | Light diffusing films, methods of making the same, and articles using the same |
| US20060263546A1 (en) * | 2005-05-20 | 2006-11-23 | General Electric Company | Light Diffusing Films, Methods of Making The Same, And Articles Using The Same |
| US7297380B2 (en) * | 2005-05-20 | 2007-11-20 | General Electric Company | Light-diffusing films, backlight display devices comprising the light-diffusing films, and methods of making the same |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3779945A (en) * | 1961-10-30 | 1973-12-18 | Geigy Ag J R | Mixtures of 3-(3,5-dialkyl-4-hydroxyphenyl)-propionic acid esters of alkanediols |
| US3285855A (en) * | 1965-03-11 | 1966-11-15 | Geigy Chem Corp | Stabilization of organic material with esters containing an alkylhydroxy-phenyl group |
| US3305520A (en) * | 1965-04-06 | 1967-02-21 | Bayer Ag | Polycarbonates stabilized by phosphites |
| US3498946A (en) * | 1965-08-03 | 1970-03-03 | Gen Electric | Pigmented polycarbonate stabilized with phosphites and ion epoxidized carboxylate |
| FR1488636A (fr) * | 1965-08-03 | 1967-07-13 | Gen Electric | Perfectionnements aux compositions polymères pigmentées stables à base de polycarbonate, et aux procédés pour leur préparation |
| US3489716A (en) * | 1968-01-10 | 1970-01-13 | Gen Electric | Aromatic polycarbonate resins stabilized with cycloaliphatic epoxy compounds |
| US3673146A (en) * | 1971-02-24 | 1972-06-27 | Gen Electric | Method for stabilizing pigmented polycarbonate resins |
| US3869423A (en) * | 1971-12-23 | 1975-03-04 | Argus Chem | Ortho-substituted hydroxyphenyl alkylene-carboxy-alkylene-1,3,5-triazines and antioxidant and synthetic resin compositions |
| US3763063A (en) * | 1972-06-14 | 1973-10-02 | Gen Electric | Color stabilized polycarbonate composition containing a cadmium or cerium salt of an alkanoic acid an alkanoic acid and an organic phosphite |
| US3839247A (en) * | 1973-01-05 | 1974-10-01 | Gen Electric | Water-clear hydrolytically stable polycarbonate composition containing an aromatic or aliphatic epoxy stabilizer |
-
1976
- 1976-03-22 US US05/668,858 patent/US4118370A/en not_active Expired - Lifetime
-
1977
- 1977-02-28 IN IN285/CAL/77A patent/IN145597B/en unknown
- 1977-03-03 CA CA273,068A patent/CA1101593A/en not_active Expired
- 1977-03-04 DE DE19772709419 patent/DE2709419A1/de not_active Withdrawn
- 1977-03-21 NL NL7703067A patent/NL7703067A/xx not_active Application Discontinuation
- 1977-03-21 GB GB11789/77A patent/GB1568648A/en not_active Expired
- 1977-03-21 FR FR7708376A patent/FR2345487A1/fr not_active Withdrawn
- 1977-03-21 DD DD7700197960A patent/DD129797A5/xx unknown
- 1977-03-22 AU AU23492/77A patent/AU510277B2/en not_active Expired
- 1977-03-22 JP JP3052777A patent/JPS52138544A/ja active Pending
- 1977-03-22 PL PL1977196823A patent/PL102955B1/pl unknown
- 1977-03-22 BE BE176006A patent/BE852746A/xx unknown
- 1977-03-22 MX MX168462A patent/MX145261A/es unknown
- 1977-03-22 BR BR7701778A patent/BR7701778A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE852746A (fr) | 1977-07-18 |
| AU510277B2 (en) | 1980-06-19 |
| DD129797A5 (de) | 1978-02-08 |
| PL102955B1 (pl) | 1979-05-31 |
| GB1568648A (en) | 1980-06-04 |
| BR7701778A (pt) | 1978-01-17 |
| JPS52138544A (en) | 1977-11-18 |
| CA1101593A (en) | 1981-05-19 |
| IN145597B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-11-18 |
| MX145261A (es) | 1982-01-18 |
| FR2345487A1 (fr) | 1977-10-21 |
| NL7703067A (nl) | 1977-09-26 |
| AU2349277A (en) | 1978-09-28 |
| US4118370A (en) | 1978-10-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |