JP3793950B2 - 安定剤としてのベンゾフラン−２−オン - Google Patents
安定剤としてのベンゾフラン−２−オン Download PDFInfo
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- JP3793950B2 JP3793950B2 JP24735594A JP24735594A JP3793950B2 JP 3793950 B2 JP3793950 B2 JP 3793950B2 JP 24735594 A JP24735594 A JP 24735594A JP 24735594 A JP24735594 A JP 24735594A JP 3793950 B2 JP3793950 B2 JP 3793950B2
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- 239000003381 stabilizer Substances 0.000 title abstract description 16
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 19
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims abstract description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
- 230000015556 catabolic process Effects 0.000 claims abstract description 7
- 238000006731 degradation reaction Methods 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 319
- 125000000217 alkyl group Chemical group 0.000 claims description 129
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 30
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 27
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 21
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000004434 sulfur atom Chemical group 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
- 150000001721 carbon Chemical group 0.000 claims description 15
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000004820 halides Chemical class 0.000 claims description 14
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 229920001059 synthetic polymer Polymers 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- -1 phenylsulphonyl Chemical group 0.000 abstract description 238
- 239000011368 organic material Substances 0.000 abstract description 15
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 47
- 229920001577 copolymer Polymers 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 26
- 229920000642 polymer Polymers 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- 239000004743 Polypropylene Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000005977 Ethylene Substances 0.000 description 11
- 239000004952 Polyamide Substances 0.000 description 11
- 229920002647 polyamide Polymers 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229920001684 low density polyethylene Polymers 0.000 description 9
- 239000004702 low-density polyethylene Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229910052615 phyllosilicate Inorganic materials 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920000098 polyolefin Polymers 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- OFQJSKKMBIPWPB-UHFFFAOYSA-N 7-tert-butyl-3-hydroxy-5-methyl-3h-1-benzofuran-2-one Chemical compound CC(C)(C)C1=CC(C)=CC2=C1OC(=O)C2O OFQJSKKMBIPWPB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 239000004700 high-density polyethylene Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
- 229920000915 polyvinyl chloride Polymers 0.000 description 5
- 239000004800 polyvinyl chloride Substances 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-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
- 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 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-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
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 4
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 4
- 239000005038 ethylene vinyl acetate Substances 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 229920000620 organic polymer Polymers 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 3
- 150000002815 nickel Chemical class 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- FQFKTKUFHWNTBN-UHFFFAOYSA-N trifluoro-$l^{3}-bromane Chemical compound FBr(F)F FQFKTKUFHWNTBN-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-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
- 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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000005406 washing Methods 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
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 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
- C08K5/15—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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Furan Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fireproofing Substances (AREA)
- Table Devices Or Equipment (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2811/93-9 | 1993-09-17 | ||
| CH281193 | 1993-09-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07247278A JPH07247278A (ja) | 1995-09-26 |
| JP3793950B2 true JP3793950B2 (ja) | 2006-07-05 |
Family
ID=4242127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24735594A Expired - Lifetime JP3793950B2 (ja) | 1993-09-17 | 1994-09-14 | 安定剤としてのベンゾフラン−２−オン |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US5614572A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0644190B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP3793950B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100361629B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1052230C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE177740T1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR9403592A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2132134C (cg-RX-API-DMAC7.html) |
| CZ (1) | CZ289139B6 (cg-RX-API-DMAC7.html) |
| DE (1) | DE59407946D1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2130385T3 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2135489C1 (cg-RX-API-DMAC7.html) |
| SK (1) | SK280591B6 (cg-RX-API-DMAC7.html) |
| TW (1) | TW270133B (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA947184B (cg-RX-API-DMAC7.html) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW270133B (cg-RX-API-DMAC7.html) * | 1993-09-17 | 1996-02-11 | Ciba Geigy | |
| TW416970B (en) * | 1995-05-31 | 2001-01-01 | Ciba Sc Holding Ag | Carrier-bound light stabilizers and antioxidants as fillers and stabilizers |
| EP0839623B1 (de) * | 1996-10-30 | 2001-01-31 | Ciba SC Holding AG | Stabilisatorkombination für das Rotomolding-Verfahren |
| WO1998055543A1 (en) * | 1997-06-05 | 1998-12-10 | Dyneon Llc | Polymer stabilization |
| AU8399398A (en) | 1997-07-14 | 1999-02-10 | Dover Chemical Corporation | Lactone/phosphite blends |
| JP2001515942A (ja) | 1997-09-10 | 2001-09-25 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 着色剤として有用なイソキシンジゴ及びそれらの製造 |
| DE19801462A1 (de) | 1998-01-16 | 1999-07-22 | Basf Ag | Katalysator und Verfahren zur Herstellung von Polytetrahydrofuran |
| CN1125072C (zh) | 1998-04-08 | 2003-10-22 | 西巴特殊化学品控股有限公司 | 二苯并二氧杂萘二酮及制备方法和在染色／着色中的应用 |
| CN1899246A (zh) * | 1998-11-02 | 2007-01-24 | 西巴特殊化学品控股有限公司 | 抗氧化剂的用途、身体护理品、家庭清洁剂和处理剂 |
| JP5313419B2 (ja) | 1999-03-10 | 2013-10-09 | チバ ホールディング インコーポレーテッド | 有機材料用着色剤としてのベンゾフラン−２−オン |
| US6664317B2 (en) * | 2000-02-18 | 2003-12-16 | Ciba Specialty Chemicals Corporation | Stabilized gamma irradiated polyolefins |
| CN1182127C (zh) * | 2000-06-28 | 2004-12-29 | 中国医学科学院药物研究所 | 新的取代的2-苯并[c]呋喃酮化合物,其制备方法以及包含它们的药物组合物 |
| CN1145671C (zh) * | 2000-08-09 | 2004-04-14 | A&M苯乙烯株式会社 | 芳族单乙烯基树脂组合物 |
| US6569927B1 (en) | 2000-10-06 | 2003-05-27 | Uniroyal Chemical Company, Inc. | Thermoplastic resins stabilized by blends of sterically hindered phenols, secondary amines, and lactones |
| US7084196B2 (en) * | 2001-03-20 | 2006-08-01 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| TW593303B (en) * | 2001-09-11 | 2004-06-21 | Ciba Sc Holding Ag | Stabilization of synthetic polymers |
| DE602006011278D1 (de) * | 2005-02-25 | 2010-02-04 | Basf Se | Fluorierte verbindungen |
| US20070049666A1 (en) * | 2005-08-30 | 2007-03-01 | James Haworth | Tocopherol compositions and uses |
| CN100345836C (zh) * | 2005-10-17 | 2007-10-31 | 湘潭大学 | 一种苯并呋喃酮类稳定剂及其应用 |
| KR101365834B1 (ko) | 2006-05-01 | 2014-02-21 | 이데미쓰 고산 가부시키가이샤 | 광반도체 밀봉 재료 |
| WO2007132615A1 (ja) * | 2006-05-12 | 2007-11-22 | Konica Minolta Opto, Inc. | セルロースアシレートフィルムの製造方法、セルロースアシレートフィルム、偏光板及び液晶表示装置 |
| CN101688004B (zh) | 2007-06-29 | 2013-11-20 | 巴塞尔聚烯烃意大利有限责任公司 | 含非酚稳定剂的受辐射聚合物组合物 |
| US7988881B2 (en) * | 2008-09-30 | 2011-08-02 | E. I. Du Pont De Nemours And Company | Multilayer laminates comprising chiral nematic liquid crystals |
| CN105646782A (zh) | 2008-12-09 | 2016-06-08 | 出光兴产株式会社 | 光学部件用树脂原料组合物、光学部件用树脂和光学部件 |
| US8286405B1 (en) * | 2009-08-11 | 2012-10-16 | Agp Plastics, Inc. | Fire and impact resistant window and building structures |
| US20130237660A1 (en) | 2010-10-25 | 2013-09-12 | Idemitsu Kosan Co. Ltd | (meth)acrylate composition |
| AU2015299175B2 (en) * | 2014-08-05 | 2018-12-20 | Basf Se | 3-phenyl-benzofuran-2-one diphosphite derivatives as stabilizers |
| WO2022215715A1 (ja) | 2021-04-07 | 2022-10-13 | 出光興産株式会社 | 射出成形用熱硬化性組成物、それを用いた成形品の製造方法、及び硬化物 |
| JPWO2022215711A1 (cg-RX-API-DMAC7.html) | 2021-04-07 | 2022-10-13 | ||
| KR20240088675A (ko) * | 2021-10-22 | 2024-06-20 | 미츠비시 가스 가가쿠 가부시키가이샤 | 열가소성 수지 조성물, 성형체, 열가소성 수지 조성물의 제조 방법 및 투과율 향상 방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2044272B (en) * | 1979-02-05 | 1983-03-16 | Sandoz Ltd | Stabilising polymers |
| US5175312A (en) * | 1989-08-31 | 1992-12-29 | Ciba-Geigy Corporation | 3-phenylbenzofuran-2-ones |
| ES2062486T3 (es) * | 1989-08-31 | 1994-12-16 | Ciba Geigy Ag | 3-fenilbenzofuran-2-onas. |
| GB2252325A (en) * | 1991-01-31 | 1992-08-05 | Ciba Geigy Ag | Stabilised polyolefin |
| TW206220B (cg-RX-API-DMAC7.html) * | 1991-07-01 | 1993-05-21 | Ciba Geigy Ag | |
| GB2267490B (en) * | 1992-05-22 | 1995-08-09 | Ciba Geigy Ag | 3-(Carboxymethoxyphenyl)benzofuran-2-one stabilisers |
| CH686306A5 (de) * | 1993-09-17 | 1996-02-29 | Ciba Geigy Ag | 3-Aryl-benzofuranone als Stabilisatoren. |
| TW270133B (cg-RX-API-DMAC7.html) * | 1993-09-17 | 1996-02-11 | Ciba Geigy |
-
1994
- 1994-08-30 TW TW083107936A patent/TW270133B/zh active
- 1994-09-08 DE DE59407946T patent/DE59407946D1/de not_active Expired - Lifetime
- 1994-09-08 AT AT94810520T patent/ATE177740T1/de not_active IP Right Cessation
- 1994-09-08 ES ES94810520T patent/ES2130385T3/es not_active Expired - Lifetime
- 1994-09-08 EP EP94810520A patent/EP0644190B1/de not_active Expired - Lifetime
- 1994-09-12 US US08/304,470 patent/US5614572A/en not_active Expired - Fee Related
- 1994-09-14 JP JP24735594A patent/JP3793950B2/ja not_active Expired - Lifetime
- 1994-09-14 SK SK1103-94A patent/SK280591B6/sk unknown
- 1994-09-14 KR KR1019940023791A patent/KR100361629B1/ko not_active Expired - Lifetime
- 1994-09-15 CZ CZ19942261A patent/CZ289139B6/cs not_active IP Right Cessation
- 1994-09-15 CA CA002132134A patent/CA2132134C/en not_active Expired - Fee Related
- 1994-09-16 RU RU94033474A patent/RU2135489C1/ru not_active IP Right Cessation
- 1994-09-16 CN CN94115267A patent/CN1052230C/zh not_active Expired - Lifetime
- 1994-09-16 BR BR9403592A patent/BR9403592A/pt not_active IP Right Cessation
- 1994-09-16 ZA ZA947184A patent/ZA947184B/xx unknown
-
1996
- 1996-09-17 US US08/715,057 patent/US5693829A/en not_active Expired - Lifetime
-
1997
- 1997-06-25 US US08/881,977 patent/US5807505A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BR9403592A (pt) | 1995-05-16 |
| RU94033474A (ru) | 1996-07-20 |
| ES2130385T3 (es) | 1999-07-01 |
| KR950008500A (ko) | 1995-04-17 |
| CN1106032A (zh) | 1995-08-02 |
| US5614572A (en) | 1997-03-25 |
| ATE177740T1 (de) | 1999-04-15 |
| CA2132134C (en) | 2006-04-04 |
| CN1052230C (zh) | 2000-05-10 |
| RU2135489C1 (ru) | 1999-08-27 |
| TW270133B (cg-RX-API-DMAC7.html) | 1996-02-11 |
| JPH07247278A (ja) | 1995-09-26 |
| ZA947184B (en) | 1995-03-17 |
| US5807505A (en) | 1998-09-15 |
| EP0644190A1 (de) | 1995-03-22 |
| DE59407946D1 (de) | 1999-04-22 |
| EP0644190B1 (de) | 1999-03-17 |
| CZ226194A3 (en) | 1995-04-12 |
| SK110394A3 (en) | 1995-06-07 |
| CZ289139B6 (cs) | 2001-11-14 |
| KR100361629B1 (ko) | 2003-02-05 |
| US5693829A (en) | 1997-12-02 |
| SK280591B6 (sk) | 2000-04-10 |
| CA2132134A1 (en) | 1995-03-18 |
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