BRPI0408492B1 - Processo para preparar ditioésteres - Google Patents
Processo para preparar ditioésteres Download PDFInfo
- Publication number
- BRPI0408492B1 BRPI0408492B1 BRPI0408492-6A BRPI0408492A BRPI0408492B1 BR PI0408492 B1 BRPI0408492 B1 BR PI0408492B1 BR PI0408492 A BRPI0408492 A BR PI0408492A BR PI0408492 B1 BRPI0408492 B1 BR PI0408492B1
- Authority
- BR
- Brazil
- Prior art keywords
- process according
- acid
- dithiocarboxylic
- group
- compound
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- -1 vinyl compound Chemical class 0.000 claims abstract description 55
- 239000012074 organic phase Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000008346 aqueous phase Substances 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- WREDNSAXDZCLCP-UHFFFAOYSA-N methanedithioic acid Chemical compound SC=S WREDNSAXDZCLCP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012988 Dithioester Substances 0.000 claims abstract description 12
- 125000005022 dithioester group Chemical group 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 10
- 239000012071 phase Substances 0.000 claims abstract description 5
- 230000002051 biphasic effect Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 44
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000002480 mineral oil Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 235000010446 mineral oil Nutrition 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 claims description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- 125000002577 pseudohalo group Chemical group 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 5
- ZGRWZUDBZZBJQB-UHFFFAOYSA-N benzenecarbodithioic acid Chemical compound SC(=S)C1=CC=CC=C1 ZGRWZUDBZZBJQB-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 5
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 5
- QNODUWNUZGTHCV-UHFFFAOYSA-M sodium;benzenecarbodithioate Chemical compound [Na+].[S-]C(=S)C1=CC=CC=C1 QNODUWNUZGTHCV-UHFFFAOYSA-M 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- KPJKMUJJFXZGAX-UHFFFAOYSA-N 2-chloropropan-2-ylbenzene Chemical compound CC(C)(Cl)C1=CC=CC=C1 KPJKMUJJFXZGAX-UHFFFAOYSA-N 0.000 description 4
- KOBJYYDWSKDEGY-UHFFFAOYSA-N 2-phenylpropan-2-yl benzenecarbodithioate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=S)C1=CC=CC=C1 KOBJYYDWSKDEGY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 150000002023 dithiocarboxylic acids Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- PGMMQIGGQSIEGH-UHFFFAOYSA-N 2-ethenyl-1,3-oxazole Chemical class C=CC1=NC=CO1 PGMMQIGGQSIEGH-UHFFFAOYSA-N 0.000 description 2
- JDCUKFVNOWJNBU-UHFFFAOYSA-N 2-ethenyl-1,3-thiazole Chemical class C=CC1=NC=CS1 JDCUKFVNOWJNBU-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N 4-isopropylbenzyl alcohol Chemical compound CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000003830 anthracite Substances 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000003077 lignite Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 description 1
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 1
- QSSAZDNARJWYEF-UHFFFAOYSA-N 1-(dibromomethyl)-2-methylbenzene Chemical group CC1=CC=CC=C1C(Br)Br QSSAZDNARJWYEF-UHFFFAOYSA-N 0.000 description 1
- CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 1
- GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-UHFFFAOYSA-N 0.000 description 1
- BDHGFCVQWMDIQX-UHFFFAOYSA-N 1-ethenyl-2-methylimidazole Chemical compound CC1=NC=CN1C=C BDHGFCVQWMDIQX-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- LEWNYOKWUAYXPI-UHFFFAOYSA-N 1-ethenylpiperidine Chemical compound C=CN1CCCCC1 LEWNYOKWUAYXPI-UHFFFAOYSA-N 0.000 description 1
- UDJZTGMLYITLIQ-UHFFFAOYSA-N 1-ethenylpyrrolidine Chemical compound C=CN1CCCC1 UDJZTGMLYITLIQ-UHFFFAOYSA-N 0.000 description 1
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- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical group C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- GDPGCHFFZZXKTQ-UHFFFAOYSA-N propyl 2-bromopropanoate Chemical compound CCCOC(=O)C(C)Br GDPGCHFFZZXKTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000010079 rubber tapping Methods 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
- 238000000926 separation method Methods 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000012546 transfer Methods 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
- 239000004711 α-olefin Substances 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/36—Esters of dithiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/18—Dithiocarboxylic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/390,015 US6841695B2 (en) | 2003-03-18 | 2003-03-18 | Process for preparing dithioesters |
| US10/390,015 | 2003-03-18 | ||
| PCT/EP2004/002058 WO2004083169A1 (en) | 2003-03-18 | 2004-03-02 | Process for preparing dithioesters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0408492A BRPI0408492A (pt) | 2006-04-04 |
| BRPI0408492B1 true BRPI0408492B1 (pt) | 2014-02-04 |
Family
ID=32987467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0408492-6A BRPI0408492B1 (pt) | 2003-03-18 | 2004-03-02 | Processo para preparar ditioésteres |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6841695B2 (https=) |
| EP (1) | EP1603873B1 (https=) |
| JP (1) | JP4653730B2 (https=) |
| KR (1) | KR100999315B1 (https=) |
| CN (1) | CN100360501C (https=) |
| AT (1) | ATE477238T1 (https=) |
| BR (1) | BRPI0408492B1 (https=) |
| CA (1) | CA2519426C (https=) |
| DE (1) | DE602004028586D1 (https=) |
| MX (1) | MXPA05009756A (https=) |
| WO (1) | WO2004083169A1 (https=) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8158725B2 (en) | 2005-08-22 | 2012-04-17 | Bridgestone Corporation | Functionalized polymers and tires therefrom |
| KR101001246B1 (ko) * | 2007-01-31 | 2010-12-17 | 주식회사 엘지화학 | 토너 제조 방법 |
| DE102007046223A1 (de) | 2007-09-26 | 2009-04-02 | Evonik Rohmax Additives Gmbh | Verwendung von Kammpolymeren zur Verringerung des Kraftstoffverbrauchs |
| DE102007032120A1 (de) | 2007-07-09 | 2009-01-15 | Evonik Rohmax Additives Gmbh | Verwendung von Kammpolymeren zur Verringerung des Kraftstoffverbrauchs |
| DE102007036856A1 (de) | 2007-08-06 | 2009-02-26 | Evonik Rohmax Additives Gmbh | Verwendung von Estergruppen-umfassenden Polymeren als Antifatigue-Additive |
| JP2008013777A (ja) * | 2007-08-29 | 2008-01-24 | Omniglow Japan Co Ltd | 化学発光用組成物および化学発光方法 |
| JP5114283B2 (ja) * | 2008-05-01 | 2013-01-09 | 三菱レイヨン株式会社 | ２−シアノプロプ−２−イルジチオベンゾアートの製造方法及びそれを用いる重合方法 |
| RU2011133876A (ru) | 2009-01-13 | 2013-02-20 | Эвоник РоМакс Эддитивс ГмбХ | Составы моторных топлив с улучшенной точкой помутнения и улучшенными свойствами при хранении |
| DE102009001446A1 (de) | 2009-03-10 | 2010-09-23 | Evonik Rohmax Additives Gmbh | Verwendung von Kammpolymeren als Antifatigue-Additive |
| DE102009001447A1 (de) | 2009-03-10 | 2010-09-16 | Evonik Rohmax Additives Gmbh | Verwendung von Kammpolymeren zur Verbesserung des Lasttragevermögens |
| DE102009002730A1 (de) | 2009-04-29 | 2010-11-04 | Evonik Rohmax Additives Gmbh | Verfahren zur Herstellung von polymeren (VI)-Verbesserern mit polaren Gruppen sowie deren Verwendung |
| KR20110030116A (ko) * | 2009-09-17 | 2011-03-23 | 에스케이케미칼주식회사 | 고순도의 ｎ,ｎ'-디치환-3,3`-디티오디프로피온아미드의 제조방법 |
| PL2305753T3 (pl) | 2009-09-25 | 2012-07-31 | Evonik Oil Additives Gmbh | Kompozycja poprawiająca płynność olejów pędnych na zimno |
| DE102010001040A1 (de) | 2010-01-20 | 2011-07-21 | Evonik RohMax Additives GmbH, 64293 | (Meth)acrylat-Polymere zur Verbesserung des Viskositätsindexes |
| US20110192076A1 (en) | 2010-02-05 | 2011-08-11 | Evonik Rohmax Additives Gmbh | Composition having improved filterability |
| DE102010028195A1 (de) | 2010-04-26 | 2011-10-27 | Evonik Rohmax Additives Gmbh | Schmiermittel für Getriebe |
| DE102010038615A1 (de) | 2010-07-29 | 2012-02-02 | Evonik Rohmax Additives Gmbh | Polyalkyl(meth)acrylat zur Verbesserung von Schmieröleigenschaften |
| US20130219868A1 (en) | 2010-10-29 | 2013-08-29 | Evonik Oil Additives Gmbh | Diesel motor having improved properties |
| WO2012076285A1 (en) | 2010-12-10 | 2012-06-14 | Evonik Rohmax Additives Gmbh | A lubricant composition |
| WO2012076676A1 (en) | 2010-12-10 | 2012-06-14 | Evonik Rohmax Additives Gmbh | A viscosity index improver comprising a polyalkyl(meth)acrylate polymer |
| DE102011003855A1 (de) | 2011-02-09 | 2012-08-09 | Evonik Rohmax Additives Gmbh | Verfahren zur Entparaffinierung von Mineralölzusammensetzungen |
| KR20140020933A (ko) | 2011-03-25 | 2014-02-19 | 에보니크 오일 아디티페스 게엠베하 | 연료 오일의 산화 안정성을 개선시키기 위한 조성물 |
| DE102011075969A1 (de) | 2011-05-17 | 2012-11-22 | Evonik Rohmax Additives Gmbh | Reibungsverbessernde Polymere für DLC-beschichtete Oberflächen |
| DE102011076364A1 (de) | 2011-05-24 | 2012-11-29 | Evonik Rohmax Additives Gmbh | Schmiermittelzusammensetzung mit phosphatfunktionalisierten Polymeren |
| CN102633234B (zh) * | 2012-04-06 | 2014-03-19 | 中国石油大学(华东) | 一种不溶性硫磺稳定剂及其制备方法 |
| WO2013182581A1 (en) | 2012-06-06 | 2013-12-12 | Evonik Oil Additives Gmbh | Fuel efficient lubricating oils |
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| US9186933B2 (en) | 2012-10-12 | 2015-11-17 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
| KR102038904B1 (ko) | 2013-02-04 | 2019-10-31 | 에보니크 오일 아디티페스 게엠베하 | 미네랄 디젤, 바이오디젤 및 그의 블렌드에서 폭넓은 적용가능성을 갖는 저온 유동 개선제 |
| WO2014152453A2 (en) * | 2013-03-14 | 2014-09-25 | Sigma-Aldrich Co. Llc | Continuous flow synthesis of dithioester compounds |
| SG11201901623TA (en) | 2016-08-31 | 2019-03-28 | Evonik Oil Additives Gmbh | Comb polymers for improving noack evaporation loss of engine oil formulations |
| RU2019121715A (ru) | 2016-12-19 | 2021-01-19 | Эвоник Оперейшнс Гмбх | Комопозиция смазочного масла, содержащая диспергирующие гребенчатые полимеры |
| JP7143395B2 (ja) | 2017-07-14 | 2022-09-28 | エボニック オペレーションズ ゲーエムベーハー | イミド官能性を有するくし型ポリマー |
| EP3450527B1 (en) | 2017-09-04 | 2020-12-02 | Evonik Operations GmbH | New viscosity index improvers with defined molecular weight distributions |
| EP3498808B1 (en) | 2017-12-13 | 2020-05-13 | Evonik Operations GmbH | Viscosity index improver with improved shear-resistance and solubility after shear |
| KR20190072779A (ko) | 2017-12-18 | 2019-06-26 | 주식회사 포스코 | 채취유닛 및 이를 포함하는 분석장치 |
| WO2020099078A1 (en) | 2018-11-13 | 2020-05-22 | Evonik Operations Gmbh | Random copolymers for use as base oils or lubricant additives |
| SG10202002189PA (en) | 2019-03-11 | 2020-10-29 | Evonik Operations Gmbh | Novel Viscosity Index Improvers |
| CN113597463B (zh) | 2019-03-20 | 2022-08-02 | 赢创运营有限公司 | 用于改进燃料经济性、分散性和沉积物性能的聚(甲基)丙烯酸烷基酯 |
| EP3778839B1 (en) | 2019-08-13 | 2021-08-04 | Evonik Operations GmbH | Viscosity index improver with improved shear-resistance |
| US11685874B2 (en) | 2019-12-16 | 2023-06-27 | Infineum International Limited | High viscosity index comb polymer viscosity modifiers and methods of modifying lubricant viscosity using same |
| US11365273B2 (en) | 2019-12-16 | 2022-06-21 | Infineum International Limited | High viscosity index comb polymer viscosity modifiers and methods of modifying lubricant viscosity using same |
| US11384311B2 (en) | 2019-12-16 | 2022-07-12 | Infineum International Limited | High viscosity index comb polymer viscosity modifiers and methods of modifying lubricant viscosity using same |
| ES2950909T3 (es) | 2020-05-05 | 2023-10-16 | Evonik Operations Gmbh | Copolímeros de polidieno lineales hidrogenados como material base o aditivos lubricantes para composiciones lubricantes |
| EP4060009B1 (en) | 2021-03-19 | 2023-05-03 | Evonik Operations GmbH | Viscosity index improver and lubricant compositions thereof |
| EP4119640B1 (en) | 2021-07-16 | 2023-06-14 | Evonik Operations GmbH | Lubricant additive composition containing polyalkylmethacrylates |
| WO2023006322A1 (en) | 2021-07-29 | 2023-02-02 | Evonik Operations Gmbh | Process for preparing low molecular weight polyacrylates and products thereof |
| WO2023099635A1 (en) | 2021-12-03 | 2023-06-08 | Totalenergies Onetech | Lubricant compositions |
| EP4441177B1 (en) | 2021-12-03 | 2025-08-06 | Evonik Operations GmbH | Boronic ester modified polyalkyl(meth)acrylate polymers |
| EP4441176B1 (en) | 2021-12-03 | 2025-10-01 | Evonik Operations GmbH | Boronic ester modified polyalkyl(meth)acrylate polymers |
| EP4441180A1 (en) | 2021-12-03 | 2024-10-09 | TotalEnergies OneTech | Lubricant compositions |
| EP4441178B1 (en) | 2021-12-03 | 2025-05-14 | TotalEnergies OneTech | Lubricant compositions |
| EP4441175B1 (en) | 2021-12-03 | 2025-08-27 | Evonik Operations GmbH | Boronic ester modified polyalkyl(meth)acrylate polymers |
| CN119630768A (zh) | 2022-08-08 | 2025-03-14 | 赢创运营有限公司 | 具有改进的低温性质的聚(甲基)丙烯酸烷基酯基聚合物 |
| EP4321602B1 (en) | 2022-08-10 | 2024-09-11 | Evonik Operations GmbH | Sulfur free poly alkyl(meth)acrylate copolymers as viscosity index improvers in lubricants |
| WO2025176598A1 (en) | 2024-02-19 | 2025-08-28 | Evonik Operations Gmbh | Low volatility comb polymer composition for engine oils |
| WO2025176603A1 (en) | 2024-02-19 | 2025-08-28 | Evonik Operations Gmbh | Low volatility comb polymer composition for engine oils |
| US20260035493A1 (en) | 2024-08-01 | 2026-02-05 | Infineum International Limited | Amine containing copolymers via radical polymerization and methods of use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2504131B1 (fr) | 1981-04-15 | 1988-03-04 | Elf Aquitaine | Procede de production de dithioacides organiques et leur application |
| JPS6168464A (ja) * | 1984-09-10 | 1986-04-08 | Nippon Nohyaku Co Ltd | チオカルボニルマロン酸エステル誘導体およびその製法 |
| CA2259559C (en) | 1996-07-10 | 2004-11-09 | E.I. Du Pont De Nemours And Company | Polymerization with living characteristics |
| JP2000198769A (ja) * | 1999-01-07 | 2000-07-18 | Ube Ind Ltd | Ｓ―ジフルオロアルケニル芳香族チオ（ジチオ）カルボン酸エステル誘導体、その製法及び農園芸用の有害生物防除剤 |
| US6458968B2 (en) | 2000-06-09 | 2002-10-01 | Rensselaer Polytechnic Institute | Dithiocarboxylic ester synthetic process |
| JP2005515261A (ja) * | 2002-01-25 | 2005-05-26 | エルジー ケミカル エルティーディー． | 水溶性ジチオエステル系化合物およびその製造方法 |
-
2003
- 2003-03-18 US US10/390,015 patent/US6841695B2/en not_active Expired - Lifetime
-
2004
- 2004-03-02 KR KR1020057017442A patent/KR100999315B1/ko not_active Expired - Lifetime
- 2004-03-02 EP EP04716228A patent/EP1603873B1/en not_active Expired - Lifetime
- 2004-03-02 CN CNB2004800071463A patent/CN100360501C/zh not_active Expired - Lifetime
- 2004-03-02 WO PCT/EP2004/002058 patent/WO2004083169A1/en not_active Ceased
- 2004-03-02 CA CA2519426A patent/CA2519426C/en not_active Expired - Lifetime
- 2004-03-02 BR BRPI0408492-6A patent/BRPI0408492B1/pt not_active IP Right Cessation
- 2004-03-02 DE DE602004028586T patent/DE602004028586D1/de not_active Expired - Lifetime
- 2004-03-02 MX MXPA05009756A patent/MXPA05009756A/es active IP Right Grant
- 2004-03-02 JP JP2006504496A patent/JP4653730B2/ja not_active Expired - Lifetime
- 2004-03-02 AT AT04716228T patent/ATE477238T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1761647A (zh) | 2006-04-19 |
| ATE477238T1 (de) | 2010-08-15 |
| KR20050111385A (ko) | 2005-11-24 |
| JP2006520339A (ja) | 2006-09-07 |
| CA2519426C (en) | 2011-09-20 |
| MXPA05009756A (es) | 2005-10-26 |
| US20040186302A1 (en) | 2004-09-23 |
| BRPI0408492A (pt) | 2006-04-04 |
| CA2519426A1 (en) | 2004-09-30 |
| KR100999315B1 (ko) | 2010-12-09 |
| JP4653730B2 (ja) | 2011-03-16 |
| EP1603873A1 (en) | 2005-12-14 |
| US6841695B2 (en) | 2005-01-11 |
| CN100360501C (zh) | 2008-01-09 |
| DE602004028586D1 (de) | 2010-09-23 |
| WO2004083169A1 (en) | 2004-09-30 |
| EP1603873B1 (en) | 2010-08-11 |
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