DE60306672T2 - Verwendung von metallkomplexverbindungen als oxidationskatalysatoren - Google Patents
Verwendung von metallkomplexverbindungen als oxidationskatalysatoren Download PDFInfo
- Publication number
- DE60306672T2 DE60306672T2 DE60306672T DE60306672T DE60306672T2 DE 60306672 T2 DE60306672 T2 DE 60306672T2 DE 60306672 T DE60306672 T DE 60306672T DE 60306672 T DE60306672 T DE 60306672T DE 60306672 T2 DE60306672 T2 DE 60306672T2
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- alkylene
- hydrogen
- 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
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- -1 METAL COMPLEX COMPOUNDS Chemical class 0.000 title claims abstract description 222
- 239000003054 catalyst Substances 0.000 title claims abstract description 56
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 55
- 230000003647 oxidation Effects 0.000 title claims description 43
- 239000003446 ligand Substances 0.000 claims abstract description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 257
- 239000001257 hydrogen Substances 0.000 claims description 253
- 125000000217 alkyl group Chemical group 0.000 claims description 212
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 196
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 177
- 229910052757 nitrogen Inorganic materials 0.000 claims description 160
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 147
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 146
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 142
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 108
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 104
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 104
- 150000002431 hydrogen Chemical class 0.000 claims description 104
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 94
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 125000003725 azepanyl group Chemical group 0.000 claims description 46
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 46
- 125000003107 substituted aryl group Chemical group 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 150000001768 cations Chemical class 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 239000003599 detergent Substances 0.000 claims description 35
- 238000004061 bleaching Methods 0.000 claims description 33
- 125000005842 heteroatom Chemical group 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 239000008187 granular material Substances 0.000 claims description 22
- 229910052742 iron Inorganic materials 0.000 claims description 21
- 239000011572 manganese Substances 0.000 claims description 21
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- 238000009472 formulation Methods 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 18
- 150000002978 peroxides Chemical class 0.000 claims description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 16
- 125000004193 piperazinyl group Chemical group 0.000 claims description 16
- 238000004140 cleaning Methods 0.000 claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
- 239000010949 copper Substances 0.000 claims description 14
- 229910052748 manganese Inorganic materials 0.000 claims description 14
- 239000007844 bleaching agent Substances 0.000 claims description 12
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 11
- 150000004696 coordination complex Chemical class 0.000 claims description 11
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [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
- 239000010936 titanium Substances 0.000 claims description 11
- 229910052719 titanium Inorganic materials 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000002736 nonionic surfactant Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 6
- 239000003945 anionic surfactant Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 230000000249 desinfective effect Effects 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 229940095064 tartrate Drugs 0.000 claims description 5
- 229910001882 dioxygen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- IADUEWIQBXOCDZ-UHFFFAOYSA-N (2S)-azetidine-2-carboxylic acid Chemical group OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 54
- 239000000243 solution Substances 0.000 description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- 238000000034 method Methods 0.000 description 29
- 229910052783 alkali metal Inorganic materials 0.000 description 25
- 239000000460 chlorine Substances 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000975 dye Substances 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 238000005406 washing Methods 0.000 description 18
- 239000004753 textile Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-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
- 229910052708 sodium Inorganic materials 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 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 14
- 125000003277 amino group Chemical group 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 12
- 238000007792 addition Methods 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 150000003235 pyrrolidines Chemical class 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 10
- ZCXLNGDZBFZUGC-UHFFFAOYSA-N 6-[4-(4-methylpiperazin-1-yl)pyridin-2-yl]-2-pyridin-2-yl-1h-pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CC=NC(C=2N=C(N=C(O)C=2)C=2N=CC=CC=2)=C1 ZCXLNGDZBFZUGC-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
- 150000007513 acids Chemical class 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 9
- 229920002678 cellulose Polymers 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 125000000129 anionic group Chemical group 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 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
- 239000003795 chemical substances by application Substances 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
- 239000000155 melt Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 239000006185 dispersion Substances 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
- 238000001694 spray drying Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 239000012190 activator Substances 0.000 description 5
- 238000005054 agglomeration Methods 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000005840 aryl radicals Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 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
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 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
- 150000002696 manganese Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910021645 metal ion Inorganic materials 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 4
- KBWPFIVQVUQTPJ-UHFFFAOYSA-N 6-(4-chloropyridin-2-yl)-2-pyridin-2-yl-1h-pyrimidin-4-one Chemical compound N=1C(O)=CC(C=2N=CC=C(Cl)C=2)=NC=1C1=CC=CC=N1 KBWPFIVQVUQTPJ-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
- 102000005575 Cellulases Human genes 0.000 description 4
- 108010084185 Cellulases Proteins 0.000 description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 4
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000005538 encapsulation Methods 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- CNFDGXZLMLFIJV-UHFFFAOYSA-L manganese(II) chloride tetrahydrate Chemical compound O.O.O.O.[Cl-].[Cl-].[Mn+2] CNFDGXZLMLFIJV-UHFFFAOYSA-L 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920002689 polyvinyl acetate Polymers 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
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- 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
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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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405929 | 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 |
|---|---|
| DE60306672D1 DE60306672D1 (de) | 2006-08-17 |
| DE60306672T2 true DE60306672T2 (de) | 2007-06-28 |
Family
ID=32187291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60306672T Expired - Lifetime DE60306672T2 (de) | 2002-10-30 | 2003-10-21 | Verwendung von metallkomplexverbindungen als oxidationskatalysatoren |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US7138363B2 (https=) |
| EP (1) | EP1556467B1 (https=) |
| JP (1) | JP4538797B2 (https=) |
| KR (1) | KR101004084B1 (https=) |
| CN (1) | CN1711347B (https=) |
| AT (1) | ATE332356T1 (https=) |
| AU (1) | AU2003278117B2 (https=) |
| BR (1) | BR0315869A (https=) |
| DE (1) | DE60306672T2 (https=) |
| ES (1) | ES2268440T3 (https=) |
| MX (1) | MXPA05004167A (https=) |
| WO (1) | WO2004039934A1 (https=) |
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 |
| 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 |
| US20090189119A1 (en) * | 2004-01-12 | 2009-07-30 | Torsten Wieprecht | 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 h202 |
| WO2005099711A1 (en) * | 2004-04-13 | 2005-10-27 | Icagen, Inc. | Polycyclic pyrimidines as potassium ion channel modulators |
| US20080000032A1 (en) * | 2004-04-29 | 2008-01-03 | Torsten Wieprecht | Use of Metal Complexes Having Bispyridylpyrimidine or Bispyridyltriazine Ligands as Catalysts for Reactions With Peroxy Compounds for Bleaching Coloured Stains on Hard Surfaces |
| DE102004024816A1 (de) * | 2004-05-17 | 2005-12-15 | Henkel Kgaa | Bleichverstärkerkombination für den Einsatz in Wasch- und Reinigungsmitteln |
| CN101415493A (zh) * | 2006-02-06 | 2009-04-22 | 西巴控股公司 | 金属络合物作为氧化催化剂的用途 |
| EP1840198A1 (en) * | 2006-03-30 | 2007-10-03 | Unilever Plc | Bleaching composition |
| JP5270678B2 (ja) * | 2007-07-23 | 2013-08-21 | ビーエーエスエフ ソシエタス・ヨーロピア | 金属錯体化合物の酸化触媒としての使用 |
| 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 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5453450A (en) * | 1993-06-16 | 1995-09-26 | Minnesota Mining And Manufacturing Company | Stabilized curable adhesives |
| US5362421A (en) | 1993-06-16 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Electrically conductive adhesive compositions |
| 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 |
| CN1351646A (zh) * | 1999-04-01 | 2002-05-29 | 荷兰联合利华有限公司 | 用于底物漂白的组合物和方法 |
| DE60211884T2 (de) * | 2001-04-30 | 2006-11-23 | Ciba Speciality Chemicals Holding Inc. | Verwendung von metallkomplexverbindungen als oxidationskatalysatoren |
-
2003
- 2003-10-21 KR KR1020057007419A patent/KR101004084B1/ko not_active Expired - Fee Related
- 2003-10-21 EP EP03769428A patent/EP1556467B1/en not_active Expired - Lifetime
- 2003-10-21 MX MXPA05004167A patent/MXPA05004167A/es active IP Right Grant
- 2003-10-21 JP JP2004547539A patent/JP4538797B2/ja not_active Expired - Fee Related
- 2003-10-21 AT AT03769428T patent/ATE332356T1/de not_active IP Right Cessation
- 2003-10-21 AU AU2003278117A patent/AU2003278117B2/en not_active Ceased
- 2003-10-21 DE DE60306672T patent/DE60306672T2/de not_active Expired - Lifetime
- 2003-10-21 US US10/531,906 patent/US7138363B2/en not_active Expired - Fee Related
- 2003-10-21 BR BR0315869-1A patent/BR0315869A/pt not_active Application Discontinuation
- 2003-10-21 WO PCT/EP2003/011636 patent/WO2004039934A1/en not_active Ceased
- 2003-10-21 CN CN2003801026668A patent/CN1711347B/zh not_active Expired - Fee Related
- 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
-
2007
- 2007-09-18 US US11/901,660 patent/US7612010B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1711347B (zh) | 2010-05-26 |
| MXPA05004167A (es) | 2005-06-08 |
| US7138363B2 (en) | 2006-11-21 |
| EP1556467B1 (en) | 2006-07-05 |
| JP4538797B2 (ja) | 2010-09-08 |
| DE60306672D1 (de) | 2006-08-17 |
| KR101004084B1 (ko) | 2010-12-27 |
| EP1556467A1 (en) | 2005-07-27 |
| US20060052265A1 (en) | 2006-03-09 |
| US7612010B2 (en) | 2009-11-03 |
| JP2006504517A (ja) | 2006-02-09 |
| ATE332356T1 (de) | 2006-07-15 |
| AU2003278117B2 (en) | 2009-07-30 |
| US7291584B2 (en) | 2007-11-06 |
| BR0315869A (pt) | 2005-09-27 |
| US20070032656A1 (en) | 2007-02-08 |
| WO2004039934A1 (en) | 2004-05-13 |
| ES2268440T3 (es) | 2007-03-16 |
| CN1711347A (zh) | 2005-12-21 |
| AU2003278117A1 (en) | 2004-05-25 |
| KR20050065636A (ko) | 2005-06-29 |
| US20080081908A1 (en) | 2008-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CIBA HOLDING INC., BASEL, CH |
|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: MAIWALD PATENTANWALTSGESELLSCHAFT MBH, 80335 MUENC |