BE1012881A5 - Composition stabilisee et procede pour stabiliser des polycarbonates, polyesters et polycetones. - Google Patents
Composition stabilisee et procede pour stabiliser des polycarbonates, polyesters et polycetones. Download PDFInfo
- Publication number
- BE1012881A5 BE1012881A5 BE9800154A BE9800154A BE1012881A5 BE 1012881 A5 BE1012881 A5 BE 1012881A5 BE 9800154 A BE9800154 A BE 9800154A BE 9800154 A BE9800154 A BE 9800154A BE 1012881 A5 BE1012881 A5 BE 1012881A5
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- BE
- Belgium
- Prior art keywords
- sep
- group
- alkyl
- substituted
- hydrogen
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 95
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 51
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 51
- 229920000728 polyester Polymers 0.000 title claims abstract description 47
- 229920001470 polyketone Polymers 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 7
- 230000003019 stabilising effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 239000003381 stabilizer Substances 0.000 claims abstract description 45
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 230000003647 oxidation Effects 0.000 claims abstract description 12
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 12
- 230000015556 catabolic process Effects 0.000 claims abstract description 11
- 238000006731 degradation reaction Methods 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 7
- -1 thianthenyl Chemical group 0.000 claims description 318
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 44
- 239000001301 oxygen Substances 0.000 claims description 44
- 229910052760 oxygen Inorganic materials 0.000 claims description 44
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 41
- 229910052717 sulfur Inorganic materials 0.000 claims description 41
- 239000011593 sulfur Substances 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001544 thienyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 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 15
- 239000000654 additive Substances 0.000 claims description 13
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 11
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 11
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 11
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004957 naphthylene group Chemical group 0.000 claims description 6
- 230000000087 stabilizing effect Effects 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000002530 phenolic antioxidant Substances 0.000 claims description 4
- 125000005954 phenoxathiinyl group Chemical group 0.000 claims description 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 4
- 239000006096 absorbing agent Substances 0.000 claims description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000003838 furazanyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 239000004611 light stabiliser Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 claims description 2
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 claims description 2
- 229920002215 polytrimethylene terephthalate Polymers 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 229920003023 plastic Polymers 0.000 abstract description 9
- 239000004033 plastic Substances 0.000 abstract description 9
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 423
- 150000003254 radicals Chemical class 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 23
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 230000006641 stabilisation Effects 0.000 description 15
- 238000011105 stabilization Methods 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001291 vacuum drying Methods 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 125000004414 alkyl thio group Chemical group 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- 238000004383 yellowing Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 9
- 230000004075 alteration Effects 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 150000001991 dicarboxylic acids Chemical class 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 125000004956 cyclohexylene group Chemical group 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 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 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 125000003302 alkenyloxy group Chemical group 0.000 description 5
- 125000005133 alkynyloxy group Chemical group 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000001746 injection moulding Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
- 229940117969 neopentyl glycol Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 4
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 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
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- 239000011732 tocopherol Substances 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 3
- 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 3
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
- YEXOWHQZWLCHHD-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1O YEXOWHQZWLCHHD-UHFFFAOYSA-N 0.000 description 3
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920004142 LEXAN™ Polymers 0.000 description 3
- 239000004418 Lexan Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 3
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- 230000009466 transformation Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- SHEXSXZCZQBTFI-UHFFFAOYSA-N tridecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)-2-sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)C(S)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SHEXSXZCZQBTFI-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])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 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH52697 | 1997-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE1012881A5 true BE1012881A5 (fr) | 2001-05-08 |
Family
ID=4189028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE9800154A BE1012881A5 (fr) | 1997-03-06 | 1998-02-27 | Composition stabilisee et procede pour stabiliser des polycarbonates, polyesters et polycetones. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6310220B1 (enExample) |
| JP (1) | JP4217926B2 (enExample) |
| KR (1) | KR100530094B1 (enExample) |
| BE (1) | BE1012881A5 (enExample) |
| DE (1) | DE19808938A1 (enExample) |
| ES (1) | ES2149678B1 (enExample) |
| FR (1) | FR2760460B1 (enExample) |
| GB (1) | GB2322861B (enExample) |
| IT (1) | IT1298340B1 (enExample) |
| NL (1) | NL1008496C2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6485657B1 (en) * | 1998-06-11 | 2002-11-26 | Teijin, Limited | Gamma-ray stabilizer and thermoplastic polymer compound including the said stabilizer |
| GB2343007B (en) | 1998-10-19 | 2001-11-07 | Ciba Sc Holding Ag | Colour photographic material |
| DE19853707A1 (de) * | 1998-11-20 | 2000-05-25 | Basf Ag | Stabilisierte Kohlenmonoxidcopolymerisate |
| AU3727300A (en) * | 1999-03-15 | 2000-10-04 | Bayer Corporation | Melt-stable, pigmented polycarbonate molding composition |
| US6069225A (en) * | 1999-03-17 | 2000-05-30 | Bayer Corporation | Polycarbonate composition useful in optical storage applications |
| WO2000077084A1 (en) * | 1999-06-14 | 2000-12-21 | Clariant Finance (Bvi) Limited | Stabilization of plastics and articles produced or coated therewith |
| CN100366678C (zh) * | 1999-09-01 | 2008-02-06 | 陶氏环球技术公司 | 含有氰基丙烯酸酯稳定剂化合物的聚碳酸酯树脂组合物 |
| US7083743B2 (en) | 1999-12-20 | 2006-08-01 | Clariant Finance (Bvi) Limited | Mixture of phosphanes and chromane derivatives |
| DE19961464A1 (de) * | 1999-12-20 | 2001-06-21 | Clariant Internat Ltd Muttenz | Mischungen aus Phosphanen und Chroman-Derivaten |
| US6197854B1 (en) * | 2000-04-03 | 2001-03-06 | Bayer Corporation | Polycarbonate composition resistant to gamma radiation |
| DE60104313T2 (de) * | 2000-05-19 | 2005-08-25 | Dow Global Technologies, Inc., Midland | Polycarbonatzusammensetzungen enthaltend schwerflüchtige uv-absorbierende verbindungen |
| US6986340B2 (en) * | 2001-02-20 | 2006-01-17 | Briggs & Stratton Corporation | Automatic fuel vent closure and fuel shutoff apparatus having mechanical actuation |
| DE10114803A1 (de) | 2001-03-26 | 2002-10-10 | Bayer Ag | Neue Polymergemische |
| JP2002322264A (ja) * | 2001-04-26 | 2002-11-08 | Mitsubishi Gas Chem Co Inc | 芳香族―脂肪族共重合ポリカーボネートの製造方法 |
| JP2002322265A (ja) * | 2001-04-26 | 2002-11-08 | Mitsubishi Gas Chem Co Inc | 芳香族―脂肪族共重合ポリカーボネートの製造方法 |
| GB0119136D0 (en) * | 2001-08-06 | 2001-09-26 | Clariant Int Ltd | Phenolfree stabilizaton of polyolefins |
| DE10360367A1 (de) * | 2003-12-22 | 2005-07-21 | Bayer Materialscience Ag | Stabilisierte thermoplastische Zusammensetzungen |
| US7611829B2 (en) | 2004-01-30 | 2009-11-03 | Fujifilm Corporation | Silver halide color photographic light-sensitive material and color image-forming method |
| US7390912B2 (en) * | 2004-12-17 | 2008-06-24 | Milliken & Company | Lactone stabilizing compositions |
| JP5309429B2 (ja) * | 2006-06-06 | 2013-10-09 | 三菱瓦斯化学株式会社 | ポリエステル樹脂組成物 |
| JP2009040866A (ja) * | 2007-08-08 | 2009-02-26 | Unitika Ltd | ポリアリレート樹脂組成物 |
| EP2406320A1 (en) * | 2009-03-13 | 2012-01-18 | Basf Se | Stabilized blends of polyester and polyamide |
| KR20120014888A (ko) * | 2009-03-13 | 2012-02-20 | 바스프 에스이 | 폴리에스테르 및 폴리아미드의 안정화된 블렌드 |
| EP3168253B1 (de) | 2015-11-13 | 2018-04-11 | Ems-Patent Ag | Flammgeschützte, aliphatische polyketonmassen, hieraus hergestellte formkörper sowie verfahren zu deren herstellung |
| EP3168252B1 (de) * | 2015-11-13 | 2019-01-09 | Ems-Patent Ag | Polyketon-formmassen mit verbesserten eigenschaften, hieraus hergestellter formkörper sowie verfahren zu dessen herstellung |
| KR102278533B1 (ko) | 2016-12-27 | 2021-07-16 | 주식회사 엘지화학 | 폴리알킬렌 카보네이트계 수지 필름 |
| KR20180085847A (ko) | 2017-01-19 | 2018-07-30 | 주식회사 효성 | 폴리에스터 수지, 열가소성 엘라스토머를 포함하는 폴리케톤 조성물 |
| KR102448024B1 (ko) | 2017-03-29 | 2022-09-28 | 에스케이이노베이션 주식회사 | 고분자 조성물 및 이를 이용한 필름 |
| KR102560650B1 (ko) * | 2017-11-14 | 2023-07-28 | 바스프 에스이 | 폴리카보네이트 조성물 |
| KR102042496B1 (ko) * | 2018-01-22 | 2019-11-08 | 효성화학 주식회사 | 기계적 물성과 자외선에 대한 내광성이 향상된 폴리케톤 블렌드 |
| JP7731760B2 (ja) * | 2021-10-22 | 2025-09-01 | 三菱瓦斯化学株式会社 | 樹脂シート |
| EP4407000A1 (en) | 2023-01-24 | 2024-07-31 | Seal for Life Global Dutch Holding B.V. | Composition for the protection of an article against corrosion |
| EP4442756A1 (en) | 2023-04-04 | 2024-10-09 | Seal for Life Global Dutch Holding B.V. | Composition for the protection of a shaped article against corrosion |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1980001566A1 (fr) * | 1979-02-05 | 1980-08-07 | Sandoz Ag | Composes benzofuran-2-oniques ou indolin-2-oniques en tant que stabilisateurs de polymeres |
| FR2710063A1 (fr) * | 1993-09-17 | 1995-03-24 | Ciba Geigy Ag | 3-Aryl-benzofurannones, utilisées en tant que stabilisants, compositions les contenant, et leur utilisation. |
| FR2746805A1 (fr) * | 1996-03-29 | 1997-10-03 | Ciba Geigy Ag | Stabilisation de polyamides, de polyesters et de polycetones avec un phosphite organique et un phenol steriquement encombre |
| EP0857765A2 (de) * | 1997-02-05 | 1998-08-12 | Ciba SC Holding AG | Stabilisatoren für Pulverlacke |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH178414A (de) | 1934-12-22 | 1935-07-15 | Ig Farbenindustrie Ag | Verfahren zur Herstellung eines kupferhaltigen Farbstoffes. |
| CH335547A (de) | 1954-02-13 | 1959-01-15 | Bayer Ag | Verfahren zur Herstellung eines braunen Tetrakisazofarbstoffes |
| CH531032A (de) | 1969-05-23 | 1972-11-30 | Sandoz Ag | Verfahren zur Herstellung von Polyazoverbindungen und ihrer Metallkomplexverbindungen |
| JPS5144156A (en) | 1974-07-26 | 1976-04-15 | Eastman Kodak Co | Shigaisennyoru retsukanitaishitekaizensaretaanteiseiojusuru horimaasoseibutsu |
| DE2926761A1 (de) | 1979-07-03 | 1981-01-22 | Bayer Ag | Metallkomplexfarbstoffe |
| DE3212240A1 (de) | 1982-04-02 | 1983-10-06 | Basf Ag | Dis- und trisazofarbstoffe |
| DE3428836A1 (de) | 1983-08-09 | 1985-02-21 | Basf Ag, 6700 Ludwigshafen | Azoverbindungen |
| EP0152012A3 (en) | 1984-02-10 | 1986-03-12 | General Electric Company | Method for enhancing ionizing radiation resistance of polymer compositions |
| DE3601900A1 (de) | 1986-01-23 | 1987-07-30 | Bayer Ag | Verwendung von 3-benzalphthaliden als uv-stabilisatoren fuer thermoplastische, aromatische polyester, polycarbonate und polyestercarbonate |
| DE3827447A1 (de) | 1988-08-12 | 1990-04-26 | Basf Ag | Polyazofarbstoffe und deren zwischenprodukte |
| US5175312A (en) | 1989-08-31 | 1992-12-29 | Ciba-Geigy Corporation | 3-phenylbenzofuran-2-ones |
| EP0415887B1 (de) * | 1989-08-31 | 1994-10-05 | Ciba-Geigy Ag | 3-Phenylbenzofuran-2-one |
| TW206220B (enExample) | 1991-07-01 | 1993-05-21 | Ciba Geigy Ag | |
| US5252643A (en) | 1991-07-01 | 1993-10-12 | Ciba-Geigy Corporation | Thiomethylated benzofuran-2-ones |
| GB2267490B (en) | 1992-05-22 | 1995-08-09 | Ciba Geigy Ag | 3-(Carboxymethoxyphenyl)benzofuran-2-one stabilisers |
| TW260686B (enExample) | 1992-05-22 | 1995-10-21 | Ciba Geigy | |
| NL9300801A (nl) | 1992-05-22 | 1993-12-16 | Ciba Geigy | 3-(acyloxyfenyl)benzofuran-2-on als stabilisatoren. |
| TW255902B (enExample) * | 1992-09-23 | 1995-09-01 | Ciba Geigy | |
| MX9305489A (es) | 1992-09-23 | 1994-03-31 | Ciba Geigy Ag | 3-(dihidrobenzofuran-5-il)benzofuran-2-onas, estabilizadores. |
| CA2218286A1 (en) | 1995-04-19 | 1996-10-24 | Shell Internationale Research Maatschappij B.V. | Polyketone polymer composition |
| US5763512A (en) | 1996-03-29 | 1998-06-09 | Ciba Specialty Chemicals Corporation | Stabilization of polyamide, polyester and polyketone |
-
1998
- 1998-02-25 ES ES009800395A patent/ES2149678B1/es not_active Expired - Lifetime
- 1998-02-27 GB GB9804057A patent/GB2322861B/en not_active Expired - Fee Related
- 1998-02-27 BE BE9800154A patent/BE1012881A5/fr active
- 1998-03-03 DE DE19808938A patent/DE19808938A1/de not_active Ceased
- 1998-03-04 JP JP06941998A patent/JP4217926B2/ja not_active Expired - Fee Related
- 1998-03-05 IT IT98MI000445A patent/IT1298340B1/it active IP Right Grant
- 1998-03-05 FR FR9802697A patent/FR2760460B1/fr not_active Expired - Fee Related
- 1998-03-05 NL NL1008496A patent/NL1008496C2/nl not_active IP Right Cessation
- 1998-03-06 KR KR1019980007415A patent/KR100530094B1/ko not_active Expired - Fee Related
-
2000
- 2000-03-02 US US09/517,261 patent/US6310220B1/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1980001566A1 (fr) * | 1979-02-05 | 1980-08-07 | Sandoz Ag | Composes benzofuran-2-oniques ou indolin-2-oniques en tant que stabilisateurs de polymeres |
| FR2710063A1 (fr) * | 1993-09-17 | 1995-03-24 | Ciba Geigy Ag | 3-Aryl-benzofurannones, utilisées en tant que stabilisants, compositions les contenant, et leur utilisation. |
| FR2746805A1 (fr) * | 1996-03-29 | 1997-10-03 | Ciba Geigy Ag | Stabilisation de polyamides, de polyesters et de polycetones avec un phosphite organique et un phenol steriquement encombre |
| EP0857765A2 (de) * | 1997-02-05 | 1998-08-12 | Ciba SC Holding AG | Stabilisatoren für Pulverlacke |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2149678A1 (es) | 2000-11-01 |
| ITMI980445A1 (it) | 1999-09-05 |
| NL1008496A1 (nl) | 1998-09-08 |
| FR2760460B1 (fr) | 2003-09-12 |
| IT1298340B1 (it) | 1999-12-20 |
| GB9804057D0 (en) | 1998-04-22 |
| ES2149678B1 (es) | 2001-05-16 |
| US6310220B1 (en) | 2001-10-30 |
| DE19808938A1 (de) | 1998-10-08 |
| GB2322861B (en) | 2001-04-18 |
| NL1008496C2 (nl) | 1998-11-13 |
| JP4217926B2 (ja) | 2009-02-04 |
| FR2760460A1 (fr) | 1998-09-11 |
| KR100530094B1 (ko) | 2006-03-09 |
| KR19980079962A (ko) | 1998-11-25 |
| GB2322861A (en) | 1998-09-09 |
| JPH10306209A (ja) | 1998-11-17 |
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