CA2292598C - Flame retardant compositions - Google Patents
Flame retardant compositions Download PDFInfo
- Publication number
- CA2292598C CA2292598C CA002292598A CA2292598A CA2292598C CA 2292598 C CA2292598 C CA 2292598C CA 002292598 A CA002292598 A CA 002292598A CA 2292598 A CA2292598 A CA 2292598A CA 2292598 C CA2292598 C CA 2292598C
- Authority
- CA
- Canada
- Prior art keywords
- flame
- hindered amine
- flame retardant
- test
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 94
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 61
- -1 amine compounds Chemical class 0.000 claims abstract description 165
- 150000001412 amines Chemical class 0.000 claims abstract description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 45
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 229920000642 polymer Polymers 0.000 claims abstract description 26
- 239000000758 substrate Substances 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 14
- 239000011574 phosphorus Substances 0.000 claims abstract description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229920000098 polyolefin Polymers 0.000 claims abstract description 8
- 230000002195 synergetic effect Effects 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract description 6
- 229920000307 polymer substrate Polymers 0.000 claims abstract description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 5
- 125000005647 linker group Chemical group 0.000 claims abstract description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001408 amides Chemical class 0.000 claims abstract description 3
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims abstract description 3
- 150000001463 antimony compounds Chemical class 0.000 claims abstract description 3
- 229910052796 boron Inorganic materials 0.000 claims abstract description 3
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 3
- 239000010703 silicon Substances 0.000 claims abstract description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229920001577 copolymer Polymers 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 20
- 230000000979 retarding effect Effects 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical group CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 77
- 238000009472 formulation Methods 0.000 description 49
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 47
- 150000001875 compounds Chemical class 0.000 description 43
- 239000000835 fiber Substances 0.000 description 33
- HCUOEKSZWPGJIM-IYNMRSRQSA-N (e,2z)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N\O)\C(N)=O HCUOEKSZWPGJIM-IYNMRSRQSA-N 0.000 description 31
- 101100162200 Aspergillus parasiticus (strain ATCC 56775 / NRRL 5862 / SRRC 143 / SU-1) aflD gene Proteins 0.000 description 31
- 239000004743 Polypropylene Substances 0.000 description 28
- 239000000654 additive Substances 0.000 description 28
- 229920001155 polypropylene Polymers 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 25
- 239000001257 hydrogen Substances 0.000 description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 21
- 239000005977 Ethylene Substances 0.000 description 21
- 239000004698 Polyethylene Substances 0.000 description 21
- 229920000573 polyethylene Polymers 0.000 description 21
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 17
- 239000008188 pellet Substances 0.000 description 16
- DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 description 15
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 15
- 239000000523 sample Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 229920002397 thermoplastic olefin Polymers 0.000 description 15
- 229910019142 PO4 Inorganic materials 0.000 description 14
- 235000021317 phosphate Nutrition 0.000 description 14
- 239000006260 foam Substances 0.000 description 13
- 229920001684 low density polyethylene Polymers 0.000 description 13
- 239000004702 low-density polyethylene Substances 0.000 description 13
- 239000010452 phosphate Substances 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 238000007906 compression Methods 0.000 description 10
- 230000006835 compression Effects 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 238000010998 test method Methods 0.000 description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 9
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
- 239000004114 Ammonium polyphosphate Substances 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 8
- 229920001276 ammonium polyphosphate Polymers 0.000 description 8
- 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 8
- 239000012796 inorganic flame retardant Substances 0.000 description 8
- 239000004745 nonwoven fabric Substances 0.000 description 8
- 229920002857 polybutadiene Polymers 0.000 description 8
- YUAPUIKGYCAHGM-UHFFFAOYSA-N 1,2-dibromo-3-(2,3-dibromopropoxy)propane Chemical compound BrCC(Br)COCC(Br)CBr YUAPUIKGYCAHGM-UHFFFAOYSA-N 0.000 description 7
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 239000006096 absorbing agent Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 238000002485 combustion reaction Methods 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 229920005669 high impact polystyrene Polymers 0.000 description 6
- 239000004700 high-density polyethylene Substances 0.000 description 6
- 239000004797 high-impact polystyrene Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 5
- SCSMZMBYJMIJTK-UHFFFAOYSA-N 2,4,9,10,11-pentaoxa-5,8-diaza-1lambda5,3lambda5-diphosphatricyclo[6.1.1.13,5]undecane 1,3-dioxide Chemical compound O1P(=O)(O2)ON2CCN2OP1(=O)O2 SCSMZMBYJMIJTK-UHFFFAOYSA-N 0.000 description 5
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 229910000410 antimony oxide Inorganic materials 0.000 description 5
- OSIVCXJNIBEGCL-UHFFFAOYSA-N bis(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(OCCCCCCCC)C(C)(C)C1 OSIVCXJNIBEGCL-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000004786 cone calorimetry Methods 0.000 description 5
- 239000000446 fuel Substances 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 5
- VVISQEKWYPFFLK-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetrabutyl-6-chloro-1,3,5-triazine-2,4-diamine Chemical compound CCCCN(CCCC)C1=NC(Cl)=NC(N(CCCC)CCCC)=N1 VVISQEKWYPFFLK-UHFFFAOYSA-N 0.000 description 4
- YZXTWMQYSSMUFH-UHFFFAOYSA-N 4-[6-(1-amino-2,2,6,6-tetramethylpiperidin-4-yl)hexyl]-2,2,6,6-tetramethylpiperidin-1-amine Chemical compound C1C(C)(C)N(N)C(C)(C)CC1CCCCCCC1CC(C)(C)N(N)C(C)(C)C1 YZXTWMQYSSMUFH-UHFFFAOYSA-N 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- ZEFSGHVBJCEKAZ-UHFFFAOYSA-N bis(2,4-ditert-butyl-6-methylphenyl) ethyl phosphite Chemical compound CC=1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1OP(OCC)OC1=C(C)C=C(C(C)(C)C)C=C1C(C)(C)C ZEFSGHVBJCEKAZ-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 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
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920002959 polymer blend Polymers 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KJYSXRBJOSZLEL-UHFFFAOYSA-N (2,4-ditert-butylphenyl) 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KJYSXRBJOSZLEL-UHFFFAOYSA-N 0.000 description 3
- ISWYKPNDQAPSER-UHFFFAOYSA-N 3,4a,5a,7-tetratert-butyl-11-fluoro-5-methyl-9a,12a-dihydro-5h-benzo[d][1,3,2]benzodioxaphosphocine Chemical compound O1P(F)OC2C=CC(C(C)(C)C)=CC2(C(C)(C)C)C(C)C2(C(C)(C)C)C=C(C(C)(C)C)C=CC21 ISWYKPNDQAPSER-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000005262 alkoxyamine group Chemical group 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 239000012496 blank sample Substances 0.000 description 3
- 125000006309 butyl amino group Chemical group 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 229940105305 carbon monoxide Drugs 0.000 description 3
- 230000001627 detrimental effect Effects 0.000 description 3
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 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 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 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 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- PDLPMGPHYARAFP-UHFFFAOYSA-N (3-hydroxy-2-phenylphenyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C=1C(O)=CC=CC=1C(=O)C1=CC=CC=C1 PDLPMGPHYARAFP-UHFFFAOYSA-N 0.000 description 2
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical class [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- BUZHLYBJNNZTPL-UHFFFAOYSA-N pentane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CC(C(O)=O)CC(O)=O BUZHLYBJNNZTPL-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical class NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical class OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 1
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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- 238000012216 screening Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
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- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
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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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
-
- 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
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
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)
- Paper (AREA)
- Printing Methods (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5133197P | 1997-06-30 | 1997-06-30 | |
| US60/051,331 | 1997-06-30 | ||
| PCT/US1998/013469 WO1999000450A1 (en) | 1997-06-30 | 1998-06-25 | Flame retardant compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2292598A1 CA2292598A1 (en) | 1999-01-07 |
| CA2292598C true CA2292598C (en) | 2008-03-18 |
Family
ID=21970653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002292598A Expired - Lifetime CA2292598C (en) | 1997-06-30 | 1998-06-25 | Flame retardant compositions |
Country Status (12)
| Country | Link |
|---|---|
| EP (2) | EP0996669B1 (enExample) |
| JP (1) | JP4378574B2 (enExample) |
| KR (1) | KR100540156B1 (enExample) |
| CN (1) | CN1178978C (enExample) |
| AU (1) | AU735643B2 (enExample) |
| BR (1) | BR9810957A (enExample) |
| CA (1) | CA2292598C (enExample) |
| DE (2) | DE69841728D1 (enExample) |
| ES (1) | ES2227855T3 (enExample) |
| RU (1) | RU2207352C2 (enExample) |
| TW (1) | TW480276B (enExample) |
| WO (1) | WO1999000450A1 (enExample) |
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| CA2329724C (en) * | 1998-04-20 | 2005-06-07 | Bba Nonwovens Simpsonville, Inc. | Nonwoven fabric having both uv stability and flame retardancy and related method for its manufacture |
| DE60017790T2 (de) * | 1999-12-09 | 2005-06-30 | Ciba Specialty Chemicals Holding Inc. | Verwendung von einer zusatzzusammensetzung zur erhöhung der lagerstabilität von äthylenischen ungesättigten harzen |
| JP2004083913A (ja) * | 2000-04-06 | 2004-03-18 | Mitsubishi Rayon Co Ltd | 難燃性ポリプロピレンフィルム |
| JP3540759B2 (ja) | 2000-04-06 | 2004-07-07 | 三菱レイヨン株式会社 | 難燃性ポリプロピレン繊維及びその製造方法 |
| JP3822046B2 (ja) * | 2000-10-11 | 2006-09-13 | 大和紡績株式会社 | 繊維およびその繊維組成物 |
| JP2002121333A (ja) * | 2000-10-13 | 2002-04-23 | Daiwabo Co Ltd | ポリオレフィン樹脂成形物及びそれからなるフィルム |
| TWI273115B (en) * | 2000-12-12 | 2007-02-11 | Ciba Sc Holding Ag | Improved weatherability of flame retardant polyolefin |
| GB2386901B (en) * | 2000-12-12 | 2004-03-31 | Ciba Sc Holding Ag | Improved weatherability of flame retardant polyolefin |
| JP2002322322A (ja) † | 2001-02-27 | 2002-11-08 | Bromine Compounds Ltd | 難燃性ポリオレフィン組成物 |
| ES2247332T3 (es) | 2001-03-20 | 2006-03-01 | Ciba Specialty Chemicals Holding Inc. | Composiciones ignifugantes. |
| US6465645B1 (en) | 2001-04-17 | 2002-10-15 | Ciba Specialty Chemicals Corporation | Long chain hindered amines and compositions stabilized therewith |
| JP3679738B2 (ja) * | 2001-07-16 | 2005-08-03 | 三菱レイヨン株式会社 | 難燃性ポリプロピレン繊維及びその製造方法 |
| US6822023B2 (en) * | 2001-12-03 | 2004-11-23 | Kaneka Corporation | Flame retardant polyolefin resin pre-expanded particles and in-mold foamed articles prepared therefrom |
| JP4406869B2 (ja) * | 2001-12-10 | 2010-02-03 | チバ ホールディング インコーポレーテッド | 難燃性組成物 |
| ATE439401T1 (de) | 2001-12-21 | 2009-08-15 | Basf Se | Neue flammhemmer |
| JP2004315544A (ja) * | 2002-02-28 | 2004-11-11 | Hagihara Industries Inc | ポリオレフィンフイルムまたはラミネートシート |
| JP2003251767A (ja) * | 2002-02-28 | 2003-09-09 | Hagihara Industries Inc | 不織布補強用ポリオレフィンクロスシート |
| JP4091317B2 (ja) * | 2002-02-28 | 2008-05-28 | 萩原工業株式会社 | 光透過性を有するクロスシート |
| JP2003251771A (ja) * | 2002-02-28 | 2003-09-09 | Hagihara Industries Inc | ポリオレフィン防炎性ラミネートシート |
| JP2003251748A (ja) * | 2002-02-28 | 2003-09-09 | Hagihara Industries Inc | 膜材料ラミネートシート |
| JP4009117B2 (ja) * | 2002-03-06 | 2007-11-14 | 大和紡績株式会社 | オレフィン複合シートおよび強化複合不織布 |
| US7323502B2 (en) | 2002-03-12 | 2008-01-29 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| JP2004000173A (ja) * | 2002-03-28 | 2004-01-08 | Hagihara Industries Inc | 防草シート |
| JP3895207B2 (ja) * | 2002-03-29 | 2007-03-22 | 大和紡績株式会社 | 難燃性ポリオレフィン繊維およびこれを用いた繊維組成物と繊維積層体 |
| CN1646615A (zh) * | 2002-04-10 | 2005-07-27 | 西巴特殊化学品控股有限公司 | 阻燃涂料 |
| US7230042B2 (en) | 2002-04-17 | 2007-06-12 | Ciba Specialty Chemicals Corp. | Flame retardant polymer compositions containing hydroxylamine esters |
| JP2003313737A (ja) * | 2002-04-24 | 2003-11-06 | Hagihara Industries Inc | パイル糸 |
| JP2004019074A (ja) * | 2002-06-19 | 2004-01-22 | Hagihara Industries Inc | 防虫網 |
| JP4016123B2 (ja) * | 2002-07-22 | 2007-12-05 | 平岡織染株式会社 | 難燃化ポリプロピレン系樹脂膜材 |
| AU2003270264A1 (en) * | 2002-10-03 | 2004-04-23 | Ciba Specialty Chemicals Holding Inc. | Flame retardant compositions |
| JP2004131869A (ja) * | 2002-10-10 | 2004-04-30 | Mitsubishi Rayon Co Ltd | 難燃性を有するポリプロピレン系熱接着性複合繊維及びその製造方法 |
| CN100352852C (zh) * | 2002-10-17 | 2007-12-05 | 西巴特殊化学品控股有限公司 | 阻燃聚合物电气部件 |
| MY139230A (en) * | 2002-10-17 | 2009-08-28 | Ciba Holding Inc | Flame retardant polymeric electrical parts |
| US7109260B2 (en) * | 2002-10-17 | 2006-09-19 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| US7138448B2 (en) * | 2002-11-04 | 2006-11-21 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| JP2004161850A (ja) * | 2002-11-12 | 2004-06-10 | Mitsubishi Rayon Co Ltd | 難燃性シート状物 |
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| US4978699A (en) * | 1988-10-24 | 1990-12-18 | Atochem North America, Inc. | Light stabilizing flame retardants |
| US5393812A (en) * | 1993-08-31 | 1995-02-28 | Hercules Incorporated | Flame retardant, light stable composition |
| EP0792911A3 (en) * | 1996-02-27 | 1998-01-14 | Fmc Corporation | Flame resistant polyolefin compositions |
-
1998
- 1998-06-25 KR KR10-1999-7012483A patent/KR100540156B1/ko not_active Expired - Lifetime
- 1998-06-25 DE DE69841728T patent/DE69841728D1/de not_active Expired - Lifetime
- 1998-06-25 AU AU81749/98A patent/AU735643B2/en not_active Expired
- 1998-06-25 RU RU2000102671/04A patent/RU2207352C2/ru active
- 1998-06-25 BR BR9810957-0A patent/BR9810957A/pt not_active IP Right Cessation
- 1998-06-25 EP EP98931701A patent/EP0996669B1/en not_active Expired - Lifetime
- 1998-06-25 EP EP04013753A patent/EP1462481B1/en not_active Expired - Lifetime
- 1998-06-25 CN CNB988067269A patent/CN1178978C/zh not_active Expired - Lifetime
- 1998-06-25 WO PCT/US1998/013469 patent/WO1999000450A1/en not_active Ceased
- 1998-06-25 ES ES98931701T patent/ES2227855T3/es not_active Expired - Lifetime
- 1998-06-25 DE DE69826477T patent/DE69826477T2/de not_active Expired - Lifetime
- 1998-06-25 JP JP50584099A patent/JP4378574B2/ja not_active Expired - Lifetime
- 1998-06-25 CA CA002292598A patent/CA2292598C/en not_active Expired - Lifetime
- 1998-08-29 TW TW087114386A patent/TW480276B/zh not_active IP Right Cessation
Also Published As
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|---|---|
| CA2292598A1 (en) | 1999-01-07 |
| WO1999000450A1 (en) | 1999-01-07 |
| EP1462481B1 (en) | 2010-06-16 |
| JP4378574B2 (ja) | 2009-12-09 |
| RU2207352C2 (ru) | 2003-06-27 |
| KR20010014333A (ko) | 2001-02-26 |
| CN1178978C (zh) | 2004-12-08 |
| TW480276B (en) | 2002-03-21 |
| AU8174998A (en) | 1999-01-19 |
| ES2227855T3 (es) | 2005-04-01 |
| CN1261904A (zh) | 2000-08-02 |
| KR100540156B1 (ko) | 2005-12-29 |
| AU735643B2 (en) | 2001-07-12 |
| EP1462481A2 (en) | 2004-09-29 |
| EP0996669B1 (en) | 2004-09-22 |
| EP1462481A3 (en) | 2004-10-13 |
| DE69826477D1 (de) | 2004-10-28 |
| EP0996669A1 (en) | 2000-05-03 |
| JP2002507238A (ja) | 2002-03-05 |
| DE69841728D1 (de) | 2010-07-29 |
| BR9810957A (pt) | 2000-09-26 |
| DE69826477T2 (de) | 2005-11-17 |
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