ES2259771T3 - Uso de compuestos de complejo metalico como catalizadores de oxidacion. - Google Patents
Uso de compuestos de complejo metalico como catalizadores de oxidacion.Info
- Publication number
- ES2259771T3 ES2259771T3 ES03763699T ES03763699T ES2259771T3 ES 2259771 T3 ES2259771 T3 ES 2259771T3 ES 03763699 T ES03763699 T ES 03763699T ES 03763699 T ES03763699 T ES 03763699T ES 2259771 T3 ES2259771 T3 ES 2259771T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- substituted
- unsubstituted
- 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
Links
- -1 METAL COMPLEX COMPOUNDS Chemical class 0.000 title claims abstract description 116
- 239000003054 catalyst Substances 0.000 title claims abstract description 44
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 29
- 230000003647 oxidation Effects 0.000 title claims abstract description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 111
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 239000003446 ligand Substances 0.000 claims abstract description 46
- 238000004061 bleaching Methods 0.000 claims abstract description 39
- 238000005406 washing Methods 0.000 claims abstract description 39
- 239000000975 dye Substances 0.000 claims abstract description 27
- 150000002978 peroxides Chemical class 0.000 claims abstract description 27
- 150000001768 cations Chemical class 0.000 claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 20
- 238000004140 cleaning Methods 0.000 claims abstract description 18
- 239000004753 textile Substances 0.000 claims abstract description 14
- 239000007844 bleaching agent Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 194
- 229910052739 hydrogen Inorganic materials 0.000 claims description 123
- 239000001257 hydrogen Substances 0.000 claims description 121
- 125000002947 alkylene group Chemical group 0.000 claims description 104
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
- 229910001868 water Inorganic materials 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 48
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 239000003795 chemical substances by application Substances 0.000 claims description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 34
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 32
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 31
- 125000004429 atom Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 239000008187 granular material Substances 0.000 claims description 24
- 239000011572 manganese Substances 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
- 150000004696 coordination complex Chemical class 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 13
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052742 iron Inorganic materials 0.000 claims description 12
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 10
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 9
- 238000004659 sterilization and disinfection Methods 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 8
- 239000001913 cellulose Substances 0.000 claims description 8
- 150000002696 manganese Chemical class 0.000 claims description 8
- 229910052748 manganese Inorganic materials 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000003945 anionic surfactant Substances 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 239000002736 nonionic surfactant Substances 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 150000002505 iron Chemical class 0.000 claims description 5
- 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 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 2
- 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 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 5
- 239000008393 encapsulating agent Substances 0.000 claims 1
- 239000008188 pellet Substances 0.000 claims 1
- 238000004065 wastewater treatment Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 30
- 230000008569 process Effects 0.000 abstract description 20
- 150000003839 salts Chemical class 0.000 abstract description 13
- 230000009471 action Effects 0.000 abstract description 12
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 abstract description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 9
- 230000004913 activation Effects 0.000 abstract description 5
- 238000009472 formulation Methods 0.000 abstract description 5
- 239000000835 fiber Substances 0.000 abstract description 4
- 229910001428 transition metal ion Inorganic materials 0.000 abstract description 4
- 102000016938 Catalase Human genes 0.000 abstract description 2
- 108010053835 Catalase Proteins 0.000 abstract description 2
- 238000007323 disproportionation reaction Methods 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 239000002253 acid Substances 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- 239000003599 detergent Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 15
- 239000002270 dispersing agent Substances 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
- 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 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- FKOZFYFYRABEQG-UHFFFAOYSA-N 2,6-bis[4-(4-methylpiperazin-1-yl)pyridin-2-yl]-1h-pyridin-4-one Chemical compound C1CN(C)CCN1C1=CC=NC(C=2NC(=CC(=O)C=2)C=2N=CC=C(C=2)N2CCN(C)CC2)=C1 FKOZFYFYRABEQG-UHFFFAOYSA-N 0.000 description 9
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 9
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- 229940088598 enzyme Drugs 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 238000005469 granulation Methods 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- VAVWNMRTAFGXDL-UHFFFAOYSA-N 2,6-bis(4-chloropyridin-2-yl)-1h-pyridin-4-one Chemical compound ClC1=CC=NC(C=2NC(=CC(=O)C=2)C=2N=CC=C(Cl)C=2)=C1 VAVWNMRTAFGXDL-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012190 activator Substances 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- NNMYRMGMVLMQAY-UHFFFAOYSA-N 4-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CC=N1 NNMYRMGMVLMQAY-UHFFFAOYSA-N 0.000 description 5
- 102000005575 Cellulases Human genes 0.000 description 5
- 108010084185 Cellulases Proteins 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
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- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 230000003179 granulation Effects 0.000 description 5
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- 238000005956 quaternization reaction Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical class [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000005054 agglomeration Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000011449 brick Substances 0.000 description 4
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- 150000007942 carboxylates Chemical class 0.000 description 4
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- 230000003197 catalytic effect Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
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- XYUWADASSSSEBX-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-5-pyridin-2-ylpentane-1,3,5-trione Chemical compound ClC1=CC=NC(C(=O)CC(=O)CC(=O)C=2N=CC=CC=2)=C1 XYUWADASSSSEBX-UHFFFAOYSA-N 0.000 description 3
- ZKPDXFCMHFRNQC-UHFFFAOYSA-N 1-pyridin-2-ylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=N1 ZKPDXFCMHFRNQC-UHFFFAOYSA-N 0.000 description 3
- WPWAOJIHYPBHLG-UHFFFAOYSA-N 2,6-bis[4-[2-(dimethylamino)ethyl-methylamino]pyridin-2-yl]-1h-pyridin-4-one Chemical compound CN(C)CCN(C)C1=CC=NC(C=2NC(=CC(=O)C=2)C=2N=CC=C(C=2)N(C)CCN(C)C)=C1 WPWAOJIHYPBHLG-UHFFFAOYSA-N 0.000 description 3
- QCJANIZZPUPSRJ-UHFFFAOYSA-N 2-(4-chloropyridin-2-yl)-6-pyridin-2-yl-1h-pyridin-4-one Chemical compound ClC1=CC=NC(C=2NC(=CC(=O)C=2)C=2N=CC=CC=2)=C1 QCJANIZZPUPSRJ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 3
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 3
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
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- 239000003352 sequestering agent Substances 0.000 description 1
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- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
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- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
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- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000012859 tissue stain Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
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- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
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Classifications
-
- 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
-
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- C11D3/395—Bleaching agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Detergent Compositions (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405591 | 2002-07-11 | ||
| EP02405591 | 2002-07-11 |
Publications (1)
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| ES2259771T3 true ES2259771T3 (es) | 2006-10-16 |
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| JP (1) | JP4643259B2 (enExample) |
| KR (1) | KR101018716B1 (enExample) |
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| AT (1) | ATE321117T1 (enExample) |
| AU (1) | AU2003253026B2 (enExample) |
| BR (1) | BR0312694B1 (enExample) |
| DE (1) | DE60304200T2 (enExample) |
| ES (1) | ES2259771T3 (enExample) |
| MX (1) | MXPA05000483A (enExample) |
| TW (1) | TWI311924B (enExample) |
| WO (1) | WO2004007657A1 (enExample) |
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| EP1383857B1 (en) * | 2001-04-30 | 2006-05-31 | Ciba SC Holding AG | Use of metal complex compounds as oxidation catalysts |
| WO2004039933A1 (en) * | 2002-10-29 | 2004-05-13 | Ciba Specialty Chemicals Holding Inc. | Use of metal complex compounds as catalysts for oxidation using molecular oxygen or air |
| GB2394720A (en) * | 2002-10-30 | 2004-05-05 | Reckitt Benckiser Nv | Metal complex compounds in dishwasher formulations |
| GB2409207B (en) * | 2003-12-20 | 2006-08-09 | Reckitt Benckiser Nv | Use of metal complex compounds as oxidation catalysts |
| EP1703977A1 (en) * | 2004-01-12 | 2006-09-27 | Ciba SC Holding AG | Use of a composition comprising metal complex compounds and polyphosphonates as catalysts for oxidations |
| BRPI0509457A (pt) * | 2004-04-29 | 2007-09-04 | Ciba Sc Holding Ag | uso de complexos de manganês tendo ligantes de bispiridilpirimidina ou bispiridiltriazina como catalisadores para reações com compostos do tipo peróxi para clarear manchas de cor em superfìcies duras |
| DE102004024816A1 (de) * | 2004-05-17 | 2005-12-15 | Henkel Kgaa | Bleichverstärkerkombination für den Einsatz in Wasch- und Reinigungsmitteln |
| WO2005116179A1 (de) * | 2004-05-17 | 2005-12-08 | Henkel Kommanditgesellschaft Auf Aktien | Waschmittel mit gegebenenfalls in situ erzeugtem bleichverstärkendem übergangsmetallkomplex |
| JP2008545624A (ja) * | 2005-05-13 | 2008-12-18 | チバ ホールディング インコーポレーテッド | 金属錯体を含むケラチン繊維を着色するための方法 |
| WO2009109533A1 (en) * | 2008-03-07 | 2009-09-11 | Basf Se | Bleach catalysts and their use as teeth whitening agents |
| EP2103735A1 (en) | 2008-03-18 | 2009-09-23 | Unilever PLC | Catalytic bleaching of substrates |
| US8492324B2 (en) * | 2008-04-09 | 2013-07-23 | Basf Se | Use of metal hydrazide complex compounds as oxidation catalysts |
| WO2010020583A1 (en) * | 2008-08-20 | 2010-02-25 | Basf Se | Improved bleach process |
| DE102008045207A1 (de) * | 2008-08-30 | 2010-03-04 | Clariant International Limited | Bleichkatalysatormischungen bestehend aus Mangansalzen und Oxalsäure oder deren Salze |
| US8415443B2 (en) * | 2009-07-10 | 2013-04-09 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| ES2533072T3 (es) * | 2009-09-18 | 2015-04-07 | Weylchem Switzerland Ag | Procedimiento para la preparación de compuestos complejos de manganeso puenteados del triazaciclononano |
| TWI551551B (zh) * | 2010-04-30 | 2016-10-01 | 三菱瓦斯化學股份有限公司 | 過氧化物活性化劑以及土壤及／或地下水之淨化方法 |
| RU2570902C2 (ru) | 2010-06-28 | 2015-12-20 | Басф Се | Отбеливающая композиция, не содержащая металл |
| ES2576504T3 (es) | 2010-12-13 | 2016-07-07 | Basf Se | Catalizadores de blanqueo |
| WO2013060706A1 (en) | 2011-10-25 | 2013-05-02 | Basf Se | Use of acrylate copolymers as soil antiredeposition agents and soil release agents in laundry processes |
| KR102004562B1 (ko) | 2011-10-25 | 2019-07-26 | 헨켈 아게 운트 코 카게아아 | 세탁 과정에서의 오염 재부착방지제 및 방오제로서의 빗살형 또는 블록 공중합체의 용도 |
| AU2014243274B2 (en) | 2013-03-27 | 2017-10-12 | Henkel Ag & Co. Kgaa | Block copolymers as soil release agents in laundry processes |
| WO2014193915A1 (en) * | 2013-05-28 | 2014-12-04 | Sigma-Aldrich Co. Llc | Manganese complexes and use thereof for preparing thin films |
| MX375951B (es) | 2013-11-27 | 2025-03-07 | Basf Se | Copolimeros aleatorios como agentes de liberacion de suciedad en procesos de lavado. |
| WO2017076771A1 (en) | 2015-11-03 | 2017-05-11 | Basf Se | Bleach catalysts |
| EP3176157A1 (en) | 2015-12-01 | 2017-06-07 | Basf Se | Bleach catalysts |
| WO2017182295A1 (en) | 2016-04-18 | 2017-10-26 | Basf Se | Liquid cleaning compositions |
| WO2017186480A1 (en) | 2016-04-26 | 2017-11-02 | Basf Se | Metal free bleaching composition |
| EP3372663A1 (en) | 2017-03-10 | 2018-09-12 | Basf Se | Bleach catalysts |
| CN111875624B (zh) * | 2020-06-06 | 2022-06-14 | 桂林理工大学 | 一种基于bteb的四核锌配合物的制备、结构和荧光应用 |
| CN120731240A (zh) | 2023-02-21 | 2025-09-30 | 巴斯夫欧洲公司 | 改性的烷氧基化聚亚烷基亚胺或改性的烷氧基化多胺 |
| WO2024175401A1 (en) | 2023-02-21 | 2024-08-29 | Basf Se | Modified alkoxylated polyalkylene imines or modified alkoxylated polyamines |
| WO2024175409A1 (en) | 2023-02-21 | 2024-08-29 | Basf Se | Modified hyperbranched alkoxylated polyalkylene imines |
| WO2024188713A1 (en) | 2023-03-13 | 2024-09-19 | Basf Se | Alkoxylated nitrogen containing polymers and their use |
| WO2024231110A1 (en) | 2023-05-05 | 2024-11-14 | Basf Se | Biodegradable polyol propoxylates, their preparation, uses, and compositions comprising them |
| WO2024256175A1 (en) | 2023-06-13 | 2024-12-19 | Basf Se | Stabilized cleaning compositions comprising edds and enzymes and their use |
| WO2025125117A1 (en) | 2023-12-15 | 2025-06-19 | Basf Se | Biodegradable propoxylated ethylenediamines, their preparation, uses, and compositions comprising them |
| WO2025131888A1 (en) | 2023-12-19 | 2025-06-26 | Basf Se | Modified alkoxylated polyalkylene imines or modified alkoxylated polyamines |
| WO2025180874A1 (en) | 2024-02-27 | 2025-09-04 | Basf Se | Substituted 1,3-dioxolane sulfates and their use |
| WO2025195856A1 (en) | 2024-03-19 | 2025-09-25 | Basf Se | Compositions of guerbet alkyl sulfates and their use |
| WO2025202032A1 (en) | 2024-03-26 | 2025-10-02 | Basf Se | Biodegradable alkoxylated polyols, their preparation, uses, and compositions comprising them |
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| JPH082878B2 (ja) * | 1988-02-12 | 1996-01-17 | 富士写真フイルム株式会社 | ４’−アルコキシ−２，２’：６’，２〃−デルピリジン誘導体及びその金属錯体 |
| FR2677766B1 (fr) * | 1991-06-14 | 1994-11-10 | Asulab Sa | Capteur de mesure de la quantite d'un composant en solution. |
| JP3852044B2 (ja) * | 1999-05-10 | 2006-11-29 | 独立行政法人科学技術振興機構 | 三脚型（トリポーダル）ピリジルアミン配位子を用いたアルキルパーオキソ単核鉄（ｉｉｉ）錯体のエポキシ化触媒 |
| GB9930248D0 (en) | 1999-12-22 | 2000-02-09 | Johnson Matthey Plc | Surface cleaner |
| EP1217056A1 (en) | 2000-12-21 | 2002-06-26 | Johnson Matthey Public Limited Company | Photocatalytic material |
| EP1383857B1 (en) * | 2001-04-30 | 2006-05-31 | Ciba SC Holding AG | Use of metal complex compounds as oxidation catalysts |
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2003
- 2003-07-03 CN CNB038164892A patent/CN1306017C/zh not_active Expired - Fee Related
- 2003-07-03 DE DE60304200T patent/DE60304200T2/de not_active Expired - Lifetime
- 2003-07-03 EP EP03763699A patent/EP1521820B1/en not_active Expired - Lifetime
- 2003-07-03 US US10/520,841 patent/US7494964B2/en not_active Expired - Fee Related
- 2003-07-03 JP JP2004520474A patent/JP4643259B2/ja not_active Expired - Fee Related
- 2003-07-03 ES ES03763699T patent/ES2259771T3/es not_active Expired - Lifetime
- 2003-07-03 BR BRPI0312694-3B1A patent/BR0312694B1/pt not_active IP Right Cessation
- 2003-07-03 WO PCT/EP2003/007121 patent/WO2004007657A1/en not_active Ceased
- 2003-07-03 AT AT03763699T patent/ATE321117T1/de not_active IP Right Cessation
- 2003-07-03 KR KR1020057000337A patent/KR101018716B1/ko not_active Expired - Fee Related
- 2003-07-03 AU AU2003253026A patent/AU2003253026B2/en not_active Ceased
- 2003-07-03 MX MXPA05000483A patent/MXPA05000483A/es active IP Right Grant
- 2003-07-09 TW TW092118692A patent/TWI311924B/zh not_active IP Right Cessation
- 2003-07-10 AR AR20030102484A patent/AR040480A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| TWI311924B (en) | 2009-07-11 |
| BR0312694A (pt) | 2005-04-26 |
| CN1668730A (zh) | 2005-09-14 |
| US7494964B2 (en) | 2009-02-24 |
| WO2004007657A1 (en) | 2004-01-22 |
| DE60304200D1 (de) | 2006-05-11 |
| MXPA05000483A (es) | 2005-03-23 |
| KR101018716B1 (ko) | 2011-03-04 |
| AU2003253026A1 (en) | 2004-02-02 |
| JP4643259B2 (ja) | 2011-03-02 |
| DE60304200T2 (de) | 2006-08-17 |
| US20060100123A1 (en) | 2006-05-11 |
| TW200404605A (en) | 2004-04-01 |
| ATE321117T1 (de) | 2006-04-15 |
| AR040480A1 (es) | 2005-04-06 |
| AU2003253026B2 (en) | 2009-05-14 |
| EP1521820B1 (en) | 2006-03-22 |
| KR20050017091A (ko) | 2005-02-21 |
| JP2005532158A (ja) | 2005-10-27 |
| CN1306017C (zh) | 2007-03-21 |
| EP1521820A1 (en) | 2005-04-13 |
| BR0312694B1 (pt) | 2013-11-05 |
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