AU699018B2 - Quarternary oxaziridinium salts as bleaching compounds - Google Patents
Quarternary oxaziridinium salts as bleaching compoundsInfo
- Publication number
- AU699018B2 AU699018B2 AU80608/94A AU8060894A AU699018B2 AU 699018 B2 AU699018 B2 AU 699018B2 AU 80608/94 A AU80608/94 A AU 80608/94A AU 8060894 A AU8060894 A AU 8060894A AU 699018 B2 AU699018 B2 AU 699018B2
- Authority
- AU
- Australia
- Prior art keywords
- group
- cycloalkyl
- alkyl
- radical selected
- aryl
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims description 37
- 238000004061 bleaching Methods 0.000 title claims description 21
- SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical class C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 title claims description 16
- 239000000203 mixture Substances 0.000 claims description 37
- -1 polycyclo Chemical group 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- 238000012546 transfer Methods 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000003599 detergent Substances 0.000 claims description 15
- 125000001475 halogen functional group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 239000007844 bleaching agent Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000004744 fabric Substances 0.000 claims description 7
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 7
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- 229930194542 Keto Natural products 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000468 ketone group Chemical group 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 238000004140 cleaning Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical compound C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 claims description 3
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 claims description 2
- KYXSVGVQGFPNRQ-UHFFFAOYSA-N 2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC=C2CN(C)CCC2=C1 KYXSVGVQGFPNRQ-UHFFFAOYSA-N 0.000 claims description 2
- 102000005575 Cellulases Human genes 0.000 claims description 2
- 108010084185 Cellulases Proteins 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108091005804 Peptidases Proteins 0.000 claims description 2
- 102000035195 Peptidases Human genes 0.000 claims description 2
- 239000004365 Protease Substances 0.000 claims description 2
- JHUXOSATQXGREM-UHFFFAOYSA-N dodecanediperoxoic acid Chemical compound OOC(=O)CCCCCCCCCCC(=O)OO JHUXOSATQXGREM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000005342 perphosphate group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- 239000012736 aqueous medium Substances 0.000 claims 5
- 239000002609 medium Substances 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 229910010272 inorganic material Inorganic materials 0.000 claims 1
- 239000011147 inorganic material Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 claims 1
- 125000005208 trialkylammonium group Chemical group 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 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
- 239000000463 material Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000344 soap Substances 0.000 description 7
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- QSKQNALVHFTOQX-UHFFFAOYSA-M sodium nonanoyloxybenzenesulfonate Chemical compound [Na+].CCCCCCCCC(=O)OC1=CC=CC=C1S([O-])(=O)=O QSKQNALVHFTOQX-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical compound CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 description 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical class COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000010936 aqueous wash Methods 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- CIOXZGOUEYHNBF-UHFFFAOYSA-N (carboxymethoxy)succinic acid Chemical compound OC(=O)COC(C(O)=O)CC(O)=O CIOXZGOUEYHNBF-UHFFFAOYSA-N 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GHPCICSQWQDZLM-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-1-methyl-3-propylurea Chemical compound CCCNC(=O)N(C)S(=O)(=O)C1=CC=C(Cl)C=C1 GHPCICSQWQDZLM-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- CFPOJWPDQWJEMO-UHFFFAOYSA-N 2-(1,2-dicarboxyethoxy)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)OC(C(O)=O)CC(O)=O CFPOJWPDQWJEMO-UHFFFAOYSA-N 0.000 description 1
- BPCGXWWABACQKS-UHFFFAOYSA-N 2-carboxyoxycarbonylbutanoic acid Chemical compound CCC(C(O)=O)C(=O)OC(O)=O BPCGXWWABACQKS-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- LDCLYCYEPBDTIV-UHFFFAOYSA-N 6-[[4-[(6-hydroperoxy-6-oxohexyl)carbamoyl]benzoyl]amino]hexaneperoxoic acid Chemical compound OOC(=O)CCCCCNC(=O)C1=CC=C(C(=O)NCCCCCC(=O)OO)C=C1 LDCLYCYEPBDTIV-UHFFFAOYSA-N 0.000 description 1
- KCAZSAYYICOMMG-UHFFFAOYSA-N 6-hydroperoxy-6-oxohexanoic acid Chemical compound OOC(=O)CCCCC(O)=O KCAZSAYYICOMMG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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- 108010065511 Amylases Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
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- 238000002835 absorbance Methods 0.000 description 1
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- 150000001450 anions Chemical class 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
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- ADKBGLXGTKOWIU-UHFFFAOYSA-N butanediperoxoic acid Chemical compound OOC(=O)CCC(=O)OO ADKBGLXGTKOWIU-UHFFFAOYSA-N 0.000 description 1
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- 238000005100 correlation spectroscopy Methods 0.000 description 1
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- 238000010168 coupling process Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- UNWDCFHEVIWFCW-UHFFFAOYSA-N decanediperoxoic acid Chemical compound OOC(=O)CCCCCCCCC(=O)OO UNWDCFHEVIWFCW-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- BRDYCNFHFWUBCZ-UHFFFAOYSA-N dodecaneperoxoic acid Chemical compound CCCCCCCCCCCC(=O)OO BRDYCNFHFWUBCZ-UHFFFAOYSA-N 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
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- 229940045996 isethionic acid Drugs 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- FBDWCTWJJMORIU-UHFFFAOYSA-N magnesium;hexahydrate Chemical compound O.O.O.O.O.O.[Mg] FBDWCTWJJMORIU-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- 230000003472 neutralizing effect Effects 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000005650 substituted phenylene group Chemical group 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 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
- 150000003852 triazoles Chemical class 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
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed 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
- C11D3/3907—Organic compounds
- C11D3/3917—Nitrogen-containing compounds
- C11D3/392—Heterocyclic compounds, e.g. cyclic imides or lactames
-
- 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
- C11D3/3907—Organic compounds
- C11D3/3917—Nitrogen-containing compounds
- C11D3/3927—Quarternary ammonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Detergent Compositions (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/151,483 US5370826A (en) | 1993-11-12 | 1993-11-12 | Quaternay oxaziridinium salts as bleaching compounds |
| US08/151483 | 1993-11-12 | ||
| PCT/EP1994/003655 WO1995013351A1 (en) | 1993-11-12 | 1994-11-03 | Quarternary oxaziridinium salts as bleaching compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU8060894A AU8060894A (en) | 1995-05-29 |
| AU699018B2 true AU699018B2 (en) | 1998-11-19 |
Family
ID=22538970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU80608/94A Ceased AU699018B2 (en) | 1993-11-12 | 1994-11-03 | Quarternary oxaziridinium salts as bleaching compounds |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US5370826A (ref) |
| EP (1) | EP0728181B1 (ref) |
| JP (1) | JPH09505333A (ref) |
| AU (1) | AU699018B2 (ref) |
| BR (1) | BR9408037A (ref) |
| CA (1) | CA2176226A1 (ref) |
| DE (1) | DE69417435T2 (ref) |
| ES (1) | ES2129143T3 (ref) |
| TW (1) | TW264513B (ref) |
| WO (1) | WO1995013351A1 (ref) |
| ZA (1) | ZA948976B (ref) |
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|---|---|---|---|---|
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| US6034048A (en) * | 1995-03-01 | 2000-03-07 | Charvid Limited Liability Co. | Non-caustic cleaning composition using an alkali salt |
| US6194367B1 (en) | 1995-03-01 | 2001-02-27 | Charvid Limited Liability Co. | Non-caustic cleaning composition comprising peroxygen compound and specific silicate and method of making the same in free-flowing, particulate form |
| US5898024A (en) * | 1995-03-01 | 1999-04-27 | Charvid Limited Liability | Non-caustic cleaning composition comprising peroxygen compound and specific silicate, and method of making the same in free-flowing, particulate form |
| US5653910A (en) * | 1995-06-07 | 1997-08-05 | Lever Brothers Company, Division Of Conopco Inc. | Bleaching compositions containing imine, hydrogen peroxide and a transition metal catalyst |
| US5576282A (en) * | 1995-09-11 | 1996-11-19 | The Procter & Gamble Company | Color-safe bleach boosters, compositions and laundry methods employing same |
| GB2311078A (en) * | 1996-03-16 | 1997-09-17 | Procter & Gamble | Bleaching composition containing cellulolytic enzyme |
| US5817614A (en) * | 1996-08-29 | 1998-10-06 | Procter & Gamble Company | Color-safe bleach boosters, compositions and laundry methods employing same |
| US5755991A (en) * | 1997-04-03 | 1998-05-26 | Lever Brothers Company, Division Of Conopco, Inc. | N-acyl oxaziridines as bleach agents |
| GB9707719D0 (en) * | 1997-04-16 | 1997-06-04 | Unilever Plc | Improvements relating to bleaching compositions comprising hypochlorite |
| ATE284945T1 (de) * | 1999-04-12 | 2005-01-15 | Unilever Nv | Mehrkomponentenbleichmittelzusammensetzungen |
| US7109156B1 (en) | 1999-08-27 | 2006-09-19 | Procter & Gamble Company | Controlled availability of formulation components, compositions and laundry methods employing same |
| TR200200459T2 (tr) * | 1999-08-27 | 2002-06-21 | The Procter & Gamble Company | Aromatizasyon ile ayrışmaya karşı dirençli formülasyon bileşenleri, bileşimler ve bunların kullanıldığı çamaşır yıkama yöntemleri. |
| BR0013616B1 (pt) * | 1999-08-27 | 2011-12-27 | composiÇço de alvejamento e composto catalisador orgÂnico de lavanderia. | |
| US6821935B1 (en) | 1999-08-27 | 2004-11-23 | Procter & Gamble Company | Color safe laundry methods employing zwitterionic formulation components |
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| ATE311432T1 (de) * | 1999-08-27 | 2005-12-15 | Procter & Gamble | Stabile substanzen, zusammensetzungen und waschverfahren zu deren verwendung |
| CN1165525C (zh) * | 1999-08-27 | 2004-09-08 | 宝洁公司 | 漂白增效剂组分、组合物及洗涤方法 |
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| JP2003508588A (ja) * | 1999-08-27 | 2003-03-04 | ザ、プロクター、エンド、ギャンブル、カンパニー | 陽イオン系処方成分を使用する、色に対して安全な洗濯方法 |
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| EP1341513B1 (en) * | 2000-12-15 | 2006-05-24 | Unilever N.V. | Oral bleaching composition |
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| US20050113246A1 (en) * | 2003-11-06 | 2005-05-26 | The Procter & Gamble Company | Process of producing an organic catalyst |
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| EP0446981A1 (en) * | 1990-03-16 | 1991-09-18 | Unilever N.V. | Bleaching compounds and compositions |
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| US3796715A (en) * | 1967-08-30 | 1974-03-12 | Hoffmann La Roche | 8-alkoxy-3,4-dihydroisoquinolines |
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| DE3407955A1 (de) * | 1984-03-03 | 1985-09-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Arzneimittel, enthaltend quartaere 3,4-dihydroisochinoliniumsalze |
| DE3938526A1 (de) * | 1989-11-21 | 1991-05-23 | Basf Ag | Verwendung von heterocyclischen verbindungen als bleichaktivatoren oder optische aufheller in wasch- und reinigungsmitteln |
| US5041232A (en) * | 1990-03-16 | 1991-08-20 | Lever Brothers Company, Division Of Conopco, Inc. | Sulfonimines as bleach catalysts |
| US5047163A (en) * | 1990-03-16 | 1991-09-10 | Lever Brothers Company, Division Of Conopco, Inc. | Activation of bleach precursors with sulfonimines |
-
1993
- 1993-11-12 US US08/151,483 patent/US5370826A/en not_active Expired - Lifetime
-
1994
- 1994-09-02 US US08/300,833 patent/US5442066A/en not_active Expired - Fee Related
- 1994-11-03 BR BR9408037A patent/BR9408037A/pt not_active Application Discontinuation
- 1994-11-03 ES ES94931578T patent/ES2129143T3/es not_active Expired - Lifetime
- 1994-11-03 DE DE69417435T patent/DE69417435T2/de not_active Expired - Fee Related
- 1994-11-03 CA CA002176226A patent/CA2176226A1/en not_active Abandoned
- 1994-11-03 AU AU80608/94A patent/AU699018B2/en not_active Ceased
- 1994-11-03 EP EP94931578A patent/EP0728181B1/en not_active Expired - Lifetime
- 1994-11-03 WO PCT/EP1994/003655 patent/WO1995013351A1/en not_active Ceased
- 1994-11-03 JP JP7513581A patent/JPH09505333A/ja active Pending
- 1994-11-11 ZA ZA948976A patent/ZA948976B/xx unknown
- 1994-12-12 TW TW083111564A patent/TW264513B/zh active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0446981A1 (en) * | 1990-03-16 | 1991-09-18 | Unilever N.V. | Bleaching compounds and compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2176226A1 (en) | 1995-05-18 |
| US5370826A (en) | 1994-12-06 |
| DE69417435T2 (de) | 1999-07-08 |
| JPH09505333A (ja) | 1997-05-27 |
| BR9408037A (pt) | 1996-12-24 |
| TW264513B (ref) | 1995-12-01 |
| ZA948976B (en) | 1996-05-13 |
| EP0728181B1 (en) | 1999-03-24 |
| WO1995013351A1 (en) | 1995-05-18 |
| AU8060894A (en) | 1995-05-29 |
| US5442066A (en) | 1995-08-15 |
| EP0728181A1 (en) | 1996-08-28 |
| ES2129143T3 (es) | 1999-06-01 |
| DE69417435D1 (de) | 1999-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |