AU2003278117B2 - Use of metal complex compounds as oxidation catalysts - Google Patents
Use of metal complex compounds as oxidation catalysts Download PDFInfo
- Publication number
- AU2003278117B2 AU2003278117B2 AU2003278117A AU2003278117A AU2003278117B2 AU 2003278117 B2 AU2003278117 B2 AU 2003278117B2 AU 2003278117 A AU2003278117 A AU 2003278117A AU 2003278117 A AU2003278117 A AU 2003278117A AU 2003278117 B2 AU2003278117 B2 AU 2003278117B2
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- Australia
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- phenyl
- hydrogen
- Prior art date
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- -1 metal complex compounds Chemical class 0.000 title claims abstract description 261
- 239000003054 catalyst Substances 0.000 title claims abstract description 61
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 54
- 230000003647 oxidation Effects 0.000 title claims description 42
- 239000003446 ligand Substances 0.000 claims abstract description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 281
- 229910052739 hydrogen Inorganic materials 0.000 claims description 238
- 239000001257 hydrogen Substances 0.000 claims description 235
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 178
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 150
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 140
- 150000001875 compounds Chemical class 0.000 claims description 128
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 112
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 102
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 102
- 125000002947 alkylene group Chemical group 0.000 claims description 99
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 94
- 150000002431 hydrogen Chemical class 0.000 claims description 85
- 229910052757 nitrogen Inorganic materials 0.000 claims description 85
- 239000000203 mixture Substances 0.000 claims description 67
- 125000003725 azepanyl group Chemical class 0.000 claims description 52
- 125000003107 substituted aryl group Chemical group 0.000 claims description 49
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 239000003599 detergent Substances 0.000 claims description 40
- 150000001768 cations Chemical class 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 238000004061 bleaching Methods 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 239000011572 manganese Substances 0.000 claims description 29
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 229910052742 iron Inorganic materials 0.000 claims description 25
- 150000002978 peroxides Chemical class 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 18
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 18
- 238000009472 formulation Methods 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 18
- 229910052748 manganese Inorganic materials 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 17
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- 125000004193 piperazinyl group Chemical group 0.000 claims description 16
- 150000003235 pyrrolidines Chemical class 0.000 claims description 16
- 239000010949 copper Substances 0.000 claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 14
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 14
- 238000004140 cleaning Methods 0.000 claims description 14
- 229910017052 cobalt Inorganic materials 0.000 claims description 14
- 239000010941 cobalt Substances 0.000 claims description 14
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 14
- 229910052802 copper Inorganic materials 0.000 claims description 14
- 229910052759 nickel Inorganic materials 0.000 claims description 14
- 229910052719 titanium Inorganic materials 0.000 claims description 14
- 239000010936 titanium Substances 0.000 claims description 14
- 125000006414 CCl Chemical group ClC* 0.000 claims description 12
- 239000007844 bleaching agent Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical group [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 10
- 150000004696 coordination complex Chemical class 0.000 claims description 10
- 230000000249 desinfective effect Effects 0.000 claims description 7
- 239000002736 nonionic surfactant Substances 0.000 claims description 7
- 239000003945 anionic surfactant Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000012459 cleaning agent Substances 0.000 claims description 3
- 239000000645 desinfectant Substances 0.000 claims description 3
- 229910052702 rhenium Inorganic materials 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 121
- 150000003254 radicals Chemical class 0.000 description 64
- 239000000243 solution Substances 0.000 description 37
- 238000000034 method Methods 0.000 description 29
- 229910052783 alkali metal Inorganic materials 0.000 description 24
- 238000005406 washing Methods 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000008187 granular material Substances 0.000 description 21
- 230000008569 process Effects 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 15
- 239000002270 dispersing agent Substances 0.000 description 15
- 239000000975 dye Substances 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
- 230000009471 action Effects 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000004753 textile Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000000129 anionic group Chemical group 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 8
- 239000001913 cellulose Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- 150000002085 enols Chemical class 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 7
- 150000002191 fatty alcohols Chemical class 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 238000001694 spray drying Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000002696 manganese Chemical class 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 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 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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Classifications
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/168—Organometallic compounds or orgometallic complexes
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3932—Inorganic compounds or complexes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Detergent Compositions (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405929.7 | 2002-10-30 | ||
| EP02405929 | 2002-10-30 | ||
| PCT/EP2003/011636 WO2004039934A1 (en) | 2002-10-30 | 2003-10-21 | Use of metal complex compounds as oxidation catalysts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003278117A1 AU2003278117A1 (en) | 2004-05-25 |
| AU2003278117B2 true AU2003278117B2 (en) | 2009-07-30 |
Family
ID=32187291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003278117A Ceased AU2003278117B2 (en) | 2002-10-30 | 2003-10-21 | Use of metal complex compounds as oxidation catalysts |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US7138363B2 (enExample) |
| EP (1) | EP1556467B1 (enExample) |
| JP (1) | JP4538797B2 (enExample) |
| KR (1) | KR101004084B1 (enExample) |
| CN (1) | CN1711347B (enExample) |
| AT (1) | ATE332356T1 (enExample) |
| AU (1) | AU2003278117B2 (enExample) |
| BR (1) | BR0315869A (enExample) |
| DE (1) | DE60306672T2 (enExample) |
| ES (1) | ES2268440T3 (enExample) |
| MX (1) | MXPA05004167A (enExample) |
| WO (1) | WO2004039934A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7259122B1 (en) * | 2004-08-30 | 2007-08-21 | John Lombardi | Chemically-resistant shelter coating |
| EP1703976A2 (en) * | 2004-01-12 | 2006-09-27 | Ciba Specialty Chemicals Holding Inc. | Use of metal complex compounds comprising pyridine, pyrimidine or s-triazine derived ligands as catalysts for oxidations with organic peroxy acids and/or precursors of organic peroxy acids and h2o2 |
| CN1929921A (zh) * | 2004-01-12 | 2007-03-14 | 西巴特殊化学制品控股公司 | 包含金属络合物和聚磷酸酯的组合物作为过氧化合物用催化剂的用途 |
| EP1742634B1 (en) * | 2004-04-13 | 2010-10-27 | ICAgen, Inc. | Polycyclic pyrimidines as potassium ion channel modulators |
| KR20070004963A (ko) * | 2004-04-29 | 2007-01-09 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | 경질 표면 상의 착색 얼룩을 표백하기 위한 퍼옥시화합물과의 반응에 대한 촉매로서 비스피리딜피리미딘 또는비스피리딜트리아진 리간드를 갖는 금속 착물의 용도 |
| DE102004024816A1 (de) * | 2004-05-17 | 2005-12-15 | Henkel Kgaa | Bleichverstärkerkombination für den Einsatz in Wasch- und Reinigungsmitteln |
| US20090044345A1 (en) * | 2006-02-06 | 2009-02-19 | Gunther Schlingloff | Use of Metal Complex Compounds as Oxidation Catalysts |
| EP1840198A1 (en) * | 2006-03-30 | 2007-10-03 | Unilever Plc | Bleaching composition |
| EP2173484A1 (en) * | 2007-07-23 | 2010-04-14 | Basf Se | Use of metal complex compounds as oxidation catalysts |
| EP2103735A1 (en) | 2008-03-18 | 2009-09-23 | Unilever PLC | Catalytic bleaching of substrates |
| CN103174006A (zh) * | 2011-11-24 | 2013-06-26 | 东华大学 | 双吡啶嘧啶金属配合物在纺织品低温练漂助剂中的应用 |
| CN107617418A (zh) * | 2016-07-16 | 2018-01-23 | 天津师范大学 | 基于3‑(5‑甲基‑1,3,4‑噁二唑)吡啶的硫氰酸根‑Co(II)配合物在吸附染料中的应用 |
| CN111479913B (zh) * | 2017-12-15 | 2021-12-21 | 罗地亚经营管理公司 | 含有镧系金属络合物的组合物 |
| JP7145802B2 (ja) * | 2019-03-27 | 2022-10-03 | 大阪ガスケミカル株式会社 | ２－アミノ－１，３，５－トリアジン化合物の製造方法 |
| CN115999640B (zh) * | 2023-02-06 | 2024-05-17 | 广西大学 | 一种蔗渣纤维素基-异质结有机复合光催化剂制备方法及其应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5362421A (en) * | 1993-06-16 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Electrically conductive adhesive compositions |
| US5453450A (en) * | 1993-06-16 | 1995-09-26 | Minnesota Mining And Manufacturing Company | Stabilized curable adhesives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH11999002188B1 (en) | 1998-09-01 | 2007-08-06 | Unilever Nv | Method of treating a textile |
| AU4109100A (en) | 1999-04-01 | 2000-10-23 | Unilever Plc | Composition and method for bleaching a substrate |
| ATE300604T1 (de) | 1999-04-01 | 2005-08-15 | Unilever Nv | Zusammensetzung und verfahren zum bleichen eines substrats |
| DE60211884T2 (de) * | 2001-04-30 | 2006-11-23 | Ciba Speciality Chemicals Holding Inc. | Verwendung von metallkomplexverbindungen als oxidationskatalysatoren |
-
2003
- 2003-10-21 US US10/531,906 patent/US7138363B2/en not_active Expired - Fee Related
- 2003-10-21 AU AU2003278117A patent/AU2003278117B2/en not_active Ceased
- 2003-10-21 KR KR1020057007419A patent/KR101004084B1/ko not_active Expired - Fee Related
- 2003-10-21 AT AT03769428T patent/ATE332356T1/de not_active IP Right Cessation
- 2003-10-21 ES ES03769428T patent/ES2268440T3/es not_active Expired - Lifetime
- 2003-10-21 US US11/520,398 patent/US7291584B2/en not_active Expired - Fee Related
- 2003-10-21 JP JP2004547539A patent/JP4538797B2/ja not_active Expired - Fee Related
- 2003-10-21 BR BR0315869-1A patent/BR0315869A/pt not_active Application Discontinuation
- 2003-10-21 CN CN2003801026668A patent/CN1711347B/zh not_active Expired - Fee Related
- 2003-10-21 EP EP03769428A patent/EP1556467B1/en not_active Expired - Lifetime
- 2003-10-21 WO PCT/EP2003/011636 patent/WO2004039934A1/en not_active Ceased
- 2003-10-21 MX MXPA05004167A patent/MXPA05004167A/es active IP Right Grant
- 2003-10-21 DE DE60306672T patent/DE60306672T2/de not_active Expired - Lifetime
-
2007
- 2007-09-18 US US11/901,660 patent/US7612010B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5362421A (en) * | 1993-06-16 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Electrically conductive adhesive compositions |
| US5453450A (en) * | 1993-06-16 | 1995-09-26 | Minnesota Mining And Manufacturing Company | Stabilized curable adhesives |
Also Published As
| Publication number | Publication date |
|---|---|
| US7612010B2 (en) | 2009-11-03 |
| US20070032656A1 (en) | 2007-02-08 |
| KR20050065636A (ko) | 2005-06-29 |
| DE60306672T2 (de) | 2007-06-28 |
| CN1711347B (zh) | 2010-05-26 |
| US7291584B2 (en) | 2007-11-06 |
| KR101004084B1 (ko) | 2010-12-27 |
| WO2004039934A1 (en) | 2004-05-13 |
| US20060052265A1 (en) | 2006-03-09 |
| JP2006504517A (ja) | 2006-02-09 |
| US7138363B2 (en) | 2006-11-21 |
| ES2268440T3 (es) | 2007-03-16 |
| CN1711347A (zh) | 2005-12-21 |
| JP4538797B2 (ja) | 2010-09-08 |
| BR0315869A (pt) | 2005-09-27 |
| ATE332356T1 (de) | 2006-07-15 |
| MXPA05004167A (es) | 2005-06-08 |
| DE60306672D1 (de) | 2006-08-17 |
| EP1556467B1 (en) | 2006-07-05 |
| US20080081908A1 (en) | 2008-04-03 |
| AU2003278117A1 (en) | 2004-05-25 |
| EP1556467A1 (en) | 2005-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: BASF SE Free format text: FORMER APPLICANT(S): CIBA HOLDING INC. |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |