OA10962A - Metal ligand containing bleaching compositions - Google Patents

Metal ligand containing bleaching compositions Download PDF

Info

Publication number: OA10962A
Authority: OA; OAPI
Prior art keywords: amide; bleaching composition; bleaching; lignin; compound
Prior art date: 1996-07-22

Application number

OA9900013A

Other languages

English (en)

Inventor

Terrence J Collins

Colin P Horwitz

Original Assignee

Univ Carnegie Mellon

Priority date (The priority date 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 date listed.)

1996-07-22

Filing date

1999-01-20

Publication date

2001-10-30

1999-01-20 Application filed by Univ Carnegie Mellon filed Critical Univ Carnegie Mellon

2001-10-30 Publication of OA10962A publication Critical patent/OA10962A/en

Links

238000004061 bleaching Methods 0.000 claims abstract description 45
239000000203 mixture Substances 0.000 claims abstract description 42
150000001875 compounds Chemical class 0.000 claims abstract description 36
239000003446 ligand Substances 0.000 claims abstract description 29
229910052799 carbon Inorganic materials 0.000 claims abstract description 23
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 22
230000001590 oxidative effect Effects 0.000 claims abstract description 21
125000001424 substituent group Chemical group 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims abstract description 17
238000007254 oxidation reaction Methods 0.000 claims abstract description 16
125000004429 atom Chemical group 0.000 claims abstract description 15
239000007844 bleaching agent Substances 0.000 claims abstract description 15
230000003647 oxidation Effects 0.000 claims abstract description 14
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 12
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 11
125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 7
125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
230000000737 periodic effect Effects 0.000 claims abstract description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 47
-1 peroxy compound Chemical class 0.000 claims description 42
229920005610 lignin Polymers 0.000 claims description 33
238000000034 method Methods 0.000 claims description 32
239000007800 oxidant agent Substances 0.000 claims description 22
229960002163 hydrogen peroxide Drugs 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000004094 surface-active agent Substances 0.000 claims description 10
230000007704 transition Effects 0.000 claims description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
239000000463 material Substances 0.000 claims description 9
239000001913 cellulose Substances 0.000 claims description 8
229920002678 cellulose Polymers 0.000 claims description 8
229910052742 iron Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
125000002091 cationic group Chemical group 0.000 claims description 4
229920001131 Pulp (paper) Polymers 0.000 claims description 3
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 3
150000001451 organic peroxides Chemical class 0.000 claims description 2
125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 2
125000005342 perphosphate group Chemical group 0.000 claims description 2
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
229940001981 carac Drugs 0.000 claims 1
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 1
239000012190 activator Substances 0.000 abstract description 18
238000006467 substitution reaction Methods 0.000 abstract description 8
125000003545 alkoxy group Chemical group 0.000 abstract description 7
125000004432 carbon atom Chemical group C* 0.000 abstract description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract description 5
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 abstract description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
150000001721 carbon Chemical group 0.000 abstract 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
229910052723 transition metal Inorganic materials 0.000 abstract 1
150000003624 transition metals Chemical class 0.000 abstract 1
150000001408 amides Chemical class 0.000 description 76
239000000543 intermediate Substances 0.000 description 38
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 29
229910001868 water Inorganic materials 0.000 description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
238000007792 addition Methods 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 20
239000000460 chlorine Substances 0.000 description 19
235000002639 sodium chloride Nutrition 0.000 description 19
239000000243 solution Substances 0.000 description 19
150000004985 diamines Chemical class 0.000 description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
239000003054 catalyst Substances 0.000 description 16
238000002835 absorbance Methods 0.000 description 15
150000002500 ions Chemical class 0.000 description 15
239000000123 paper Substances 0.000 description 15
238000005481 NMR spectroscopy Methods 0.000 description 14
239000011780 sodium chloride Substances 0.000 description 14
238000012512 characterization method Methods 0.000 description 12
OSVXSBDYLRYLIG-UHFFFAOYSA-N dioxidochlorine(.) Chemical compound O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
238000005710 macrocyclization reaction Methods 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
102000004190 Enzymes Human genes 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000003513 alkali Substances 0.000 description 7
239000002738 chelating agent Substances 0.000 description 7
229940088598 enzyme Drugs 0.000 description 7
230000001965 increasing effect Effects 0.000 description 7
239000000523 sample Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000004155 Chlorine dioxide Substances 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
235000019398 chlorine dioxide Nutrition 0.000 description 6
229940099041 chlorine dioxide Drugs 0.000 description 6
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000000975 dye Substances 0.000 description 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
HCZXHQADHZIEJD-CIUDSAMLSA-N Ala-Leu-Ala Chemical compound C[C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(O)=O HCZXHQADHZIEJD-CIUDSAMLSA-N 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
108091005804 Peptidases Proteins 0.000 description 5
239000004365 Protease Substances 0.000 description 5
230000010933 acylation Effects 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
150000002978 peroxides Chemical class 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
230000002459 sustained effect Effects 0.000 description 5
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
FWKCXFPQSXNCBW-UHFFFAOYSA-N 2,2-diethylpropanedioyl dichloride Chemical compound CCC(CC)(C(Cl)=O)C(Cl)=O FWKCXFPQSXNCBW-UHFFFAOYSA-N 0.000 description 4
102000013142 Amylases Human genes 0.000 description 4
108010065511 Amylases Proteins 0.000 description 4
229910016523 CuKa Inorganic materials 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
235000019418 amylase Nutrition 0.000 description 4
239000003945 anionic surfactant Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
150000001540 azides Chemical class 0.000 description 4
239000013522 chelant Substances 0.000 description 4
230000008878 coupling Effects 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
229940117927 ethylene oxide Drugs 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
150000002678 macrocyclic compounds Chemical class 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
239000002736 nonionic surfactant Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
235000012239 silicon dioxide Nutrition 0.000 description 4
239000011734 sodium Substances 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 4
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
IWFHBRFJOHTIPU-UHFFFAOYSA-N 4,5-dichlorobenzene-1,2-diamine Chemical compound NC1=CC(Cl)=C(Cl)C=C1N IWFHBRFJOHTIPU-UHFFFAOYSA-N 0.000 description 3
238000012935 Averaging Methods 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
102000035195 Peptidases Human genes 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229940025131 amylases Drugs 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
150000001555 benzenes Chemical group 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000001360 collision-induced dissociation Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
238000004042 decolorization Methods 0.000 description 3
YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 3
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
238000003780 insertion Methods 0.000 description 3
230000037431 insertion Effects 0.000 description 3
239000011159 matrix material Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
239000011591 potassium Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000010453 quartz Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000758 substrate Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,4-dimethylpentane Chemical compound CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 2
XNCSCQSQSGDGES-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]propyl-(carboxymethyl)amino]acetic acid Chemical class OC(=O)CN(CC(O)=O)C(C)CN(CC(O)=O)CC(O)=O XNCSCQSQSGDGES-UHFFFAOYSA-N 0.000 description 2
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229920003043 Cellulose fiber Polymers 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
206010053317 Hydrophobia Diseases 0.000 description 2
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 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
108010056079 Subtilisins Proteins 0.000 description 2
102000005158 Subtilisins Human genes 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000003868 ammonium compounds Chemical class 0.000 description 2
239000002280 amphoteric surfactant Substances 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
230000008901 benefit Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
239000003093 cationic surfactant Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
125000002993 cycloalkylene group Chemical group 0.000 description 2
230000006378 damage Effects 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
125000006575 electron-withdrawing group Chemical group 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
230000002708 enhancing effect Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000010265 fast atom bombardment Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000036541 health Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000010410 layer Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229910052750 molybdenum Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
230000008569 process Effects 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000004076 pulp bleaching Methods 0.000 description 2
230000005855 radiation Effects 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
150000004760 silicates Chemical class 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
ODBPOHVSVJZQRX-UHFFFAOYSA-M sodium;[2-[2-[bis(phosphonomethyl)amino]ethyl-(phosphonomethyl)amino]ethyl-(phosphonomethyl)amino]methyl-hydroxyphosphinate Chemical compound [Na+].OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)([O-])=O ODBPOHVSVJZQRX-UHFFFAOYSA-M 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
238000000547 structure data Methods 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
229910052721 tungsten Inorganic materials 0.000 description 2
239000002888 zwitterionic surfactant Substances 0.000 description 2
WGECXQBGLLYSFP-UHFFFAOYSA-N (+-)-2,3-dimethyl-pentane Natural products CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 1
FVMNARAKYNRZID-UHFFFAOYSA-M (2z)-1-ethyl-2-[(e)-3-(1-ethylquinolin-1-ium-2-yl)prop-2-enylidene]quinoline;chloride Chemical compound [Cl-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC FVMNARAKYNRZID-UHFFFAOYSA-M 0.000 description 1
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
WOXWUZCRWJWTRT-UHFFFAOYSA-N 1-amino-1-cyclohexanecarboxylic acid Chemical compound OC(=O)C1(N)CCCCC1 WOXWUZCRWJWTRT-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
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239000002243 precursor Substances 0.000 description 1
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MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
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Classifications

- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C9/00—After-treatment of cellulose pulp, e.g. of wood pulp, or cotton linters ; Treatment of dilute or dewatered pulp or process improvement taking place after obtaining the raw cellulosic material and not provided for elsewhere
- D21C9/10—Bleaching ; Apparatus therefor
- D21C9/1026—Other features in bleaching processes
- D21C9/1036—Use of compounds accelerating or improving the efficiency of the processes
- 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
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/006—Catalysts comprising hydrides, coordination complexes or organic compounds comprising organic radicals, e.g. TEMPO
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/10—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- 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
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
- B01J2531/72—Manganese
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/184—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine mixed aromatic/aliphatic ring systems, e.g. indoline

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Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Inorganic Chemistry (AREA)
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OA9900013A 1996-07-22 1999-01-20 Metal ligand containing bleaching compositions OA10962A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/684,670 US5876625A (en)	1996-07-22	1996-07-22	Metal ligand containing bleaching compositions
US08/804,776 US5853428A (en)	1996-07-22	1997-02-24	Metal ligand containing bleaching compositions

Publications (1)

Publication Number	Publication Date
OA10962A true OA10962A (en)	2001-10-30

Family

ID=24749062

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
OA9900013A OA10962A (en)	1996-07-22	1999-01-20	Metal ligand containing bleaching compositions
OA9900012A OA10961A (en)	1996-07-22	1999-01-20	Metal ligand containing bleaching compositions

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
OA9900012A OA10961A (en)	1996-07-22	1999-01-20	Metal ligand containing bleaching compositions

Country Status (22)

Country	Link
US (3)	US5876625A (fr)
EP (2)	EP0918840B1 (fr)
JP (2)	JP3623802B2 (fr)
KR (2)	KR20000067992A (fr)
CN (2)	CN100352902C (fr)
AP (2)	AP1013A (fr)
AT (2)	ATE225844T1 (fr)
AU (2)	AU730906B2 (fr)
BR (2)	BR9710538A (fr)
CA (2)	CA2261228C (fr)
DE (2)	DE69716275T2 (fr)
DK (1)	DK0923635T3 (fr)
ES (2)	ES2186906T3 (fr)
HK (2)	HK1020350A1 (fr)
IL (1)	IL128147A0 (fr)
NO (2)	NO326521B1 (fr)
NZ (2)	NZ333796A (fr)
OA (2)	OA10962A (fr)
PL (2)	PL188333B1 (fr)
PT (1)	PT923635E (fr)
RU (2)	RU2193050C2 (fr)
WO (2)	WO1998003625A1 (fr)

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1996
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1997
- 1997-02-24 US US08/804,776 patent/US5853428A/en not_active Expired - Fee Related
- 1997-07-21 JP JP50704898A patent/JP3623802B2/ja not_active Expired - Fee Related
- 1997-07-21 BR BR9710538A patent/BR9710538A/pt not_active IP Right Cessation
- 1997-07-21 IL IL12814797A patent/IL128147A0/xx unknown
- 1997-07-21 NZ NZ333796A patent/NZ333796A/xx unknown
- 1997-07-21 PL PL97331316A patent/PL188333B1/pl not_active IP Right Cessation
- 1997-07-21 EP EP97933485A patent/EP0918840B1/fr not_active Expired - Lifetime
- 1997-07-21 KR KR1019997000526A patent/KR20000067992A/ko not_active Application Discontinuation
- 1997-07-21 CA CA002261228A patent/CA2261228C/fr not_active Expired - Fee Related
- 1997-07-21 WO PCT/US1997/012358 patent/WO1998003625A1/fr active IP Right Grant
- 1997-07-21 DE DE69716275T patent/DE69716275T2/de not_active Expired - Fee Related
- 1997-07-21 AU AU36655/97A patent/AU730906B2/en not_active Ceased
- 1997-07-21 RU RU99103697/04A patent/RU2193050C2/ru not_active IP Right Cessation
- 1997-07-21 CN CNB971979782A patent/CN100352902C/zh not_active Expired - Fee Related
- 1997-07-21 AT AT97933485T patent/ATE225844T1/de not_active IP Right Cessation
- 1997-07-21 AP APAP/P/1999/001456A patent/AP1013A/en active
- 1997-07-21 ES ES97933485T patent/ES2186906T3/es not_active Expired - Lifetime
- 1997-07-22 RU RU99103691/04A patent/RU2193049C2/ru not_active IP Right Cessation
- 1997-07-22 NZ NZ333795A patent/NZ333795A/en unknown
- 1997-07-22 AT AT97934248T patent/ATE233312T1/de not_active IP Right Cessation
- 1997-07-22 CA CA002261229A patent/CA2261229C/fr not_active Expired - Fee Related
- 1997-07-22 DE DE69719337T patent/DE69719337T2/de not_active Expired - Fee Related
- 1997-07-22 KR KR1019997000531A patent/KR20000067996A/ko not_active Application Discontinuation
- 1997-07-22 ES ES97934248T patent/ES2197356T3/es not_active Expired - Lifetime
- 1997-07-22 EP EP97934248A patent/EP0923635B1/fr not_active Expired - Lifetime
- 1997-07-22 BR BR9710514-7A patent/BR9710514A/pt not_active IP Right Cessation
- 1997-07-22 AP APAP/P/1999/001449A patent/AP905A/en active
- 1997-07-22 AU AU37352/97A patent/AU720042B2/en not_active Ceased
- 1997-07-22 JP JP50716598A patent/JP3623803B2/ja not_active Expired - Fee Related
- 1997-07-22 PL PL97331352A patent/PL331352A1/xx unknown
- 1997-07-22 PT PT97934248T patent/PT923635E/pt unknown
- 1997-07-22 WO PCT/US1997/012744 patent/WO1998003626A2/fr active IP Right Grant
- 1997-07-22 DK DK97934248T patent/DK0923635T3/da active
- 1997-07-22 CN CNB971980942A patent/CN100390259C/zh not_active Expired - Fee Related
1998
- 1998-07-20 US US09/119,459 patent/US6099586A/en not_active Expired - Lifetime
1999
- 1999-01-20 OA OA9900013A patent/OA10962A/en unknown
- 1999-01-20 OA OA9900012A patent/OA10961A/en unknown
- 1999-01-21 NO NO19990267A patent/NO326521B1/no not_active IP Right Cessation
- 1999-01-21 NO NO990266A patent/NO990266L/no not_active Application Discontinuation
- 1999-11-29 HK HK99105541A patent/HK1020350A1/xx not_active IP Right Cessation
- 1999-12-21 HK HK99106004A patent/HK1020750A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
HK1020750A1 (en)	2000-05-19
ATE225844T1 (de)	2002-10-15
JP3623803B2 (ja)	2005-02-23
NZ333795A (en)	2000-07-28
WO1998003626A2 (fr)	1998-01-29
CN100390259C (zh)	2008-05-28
EP0918840B1 (fr)	2002-10-09
NO990266D0 (no)	1999-01-21
ES2197356T3 (es)	2004-01-01
OA10961A (en)	2001-10-30
HK1020350A1 (en)	2000-04-14
NZ333796A (en)	2000-09-29
CA2261229C (fr)	2007-01-09
PL331316A1 (en)	1999-07-05
EP0923635A2 (fr)	1999-06-23
RU2193049C2 (ru)	2002-11-20
NO326521B1 (no)	2008-12-22
IL128147A0 (en)	1999-11-30
PL331352A1 (en)	1999-07-05
NO990267D0 (no)	1999-01-21
AP9901456A0 (en)	1999-03-31
KR20000067996A (ko)	2000-11-25
AU720042B2 (en)	2000-05-25
KR20000067992A (ko)	2000-11-25
CN1230980A (zh)	1999-10-06
AP9901449A0 (en)	1999-03-31
RU2193050C2 (ru)	2002-11-20
CA2261228C (fr)	2007-01-09
US6099586A (en)	2000-08-08
WO1998003626A3 (fr)	1998-02-26
DE69719337T2 (de)	2004-04-08
PT923635E (pt)	2003-07-31
NO990266L (no)	1999-03-22
AU730906B2 (en)	2001-03-15
CA2261228A1 (fr)	1998-01-29
US5876625A (en)	1999-03-02
CN100352902C (zh)	2007-12-05
CN1230979A (zh)	1999-10-06
DK0923635T3 (da)	2003-06-23
CA2261229A1 (fr)	1998-01-29
NO990267L (no)	1999-03-15
WO1998003625A1 (fr)	1998-01-29
BR9710514A (pt)	2000-10-24
ATE233312T1 (de)	2003-03-15
AU3665597A (en)	1998-02-10
JP2001503073A (ja)	2001-03-06
DE69716275T2 (de)	2003-07-10
JP2000515194A (ja)	2000-11-14
DE69719337D1 (de)	2003-04-03
JP3623802B2 (ja)	2005-02-23
DE69716275D1 (de)	2002-11-14
AP905A (en)	2000-11-27
AU3735297A (en)	1998-02-10
EP0918840A1 (fr)	1999-06-02
PL188333B1 (pl)	2005-01-31
BR9710538A (pt)	1999-08-17
US5853428A (en)	1998-12-29
EP0923635B1 (fr)	2003-02-26
AP1013A (en)	2001-09-27
ES2186906T3 (es)	2003-05-16

Publication	Publication Date	Title
OA10962A (en)	2001-10-30	Metal ligand containing bleaching compositions
US6241779B1 (en)	2001-06-05	Metal ligand containing bleaching compositions
Sen et al.	2015	Functional zinc (II) phthalocyanines bearing Schiff base complexes as oxidation catalysts for bleaching systems
Robinson et al.	2025	Influence of a 2nd Sphere Hydrogen‐Bond Donor on the Reactivity of Non‐heme Fe (II) Complexes in Alkane, Alkene and Aromatic Oxidation with H2O2
MXPA00011039A (en)	2002-02-26	Metal ligand containing bleaching compositions
MXPA99000790A (es)	2002-05-09	Composiciones de blanqueo que contienen ligando metalico