AU2003219043B2 - Ammonium nitriles and the use thereof as hydrophobic bleaching activators - Google Patents
Ammonium nitriles and the use thereof as hydrophobic bleaching activators Download PDFInfo
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- AU2003219043B2 AU2003219043B2 AU2003219043A AU2003219043A AU2003219043B2 AU 2003219043 B2 AU2003219043 B2 AU 2003219043B2 AU 2003219043 A AU2003219043 A AU 2003219043A AU 2003219043 A AU2003219043 A AU 2003219043A AU 2003219043 B2 AU2003219043 B2 AU 2003219043B2
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- Australia
- Prior art keywords
- alkyl
- acid
- compound
- formula
- hydrogen
- Prior art date
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- -1 Ammonium nitriles Chemical class 0.000 title claims description 67
- 238000004061 bleaching Methods 0.000 title claims description 42
- 239000012190 activator Substances 0.000 title description 39
- 230000002209 hydrophobic effect Effects 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims description 94
- 150000001875 compounds Chemical class 0.000 claims description 35
- 238000005406 washing Methods 0.000 claims description 28
- 238000004140 cleaning Methods 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 238000009472 formulation Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
- 238000004851 dishwashing Methods 0.000 claims description 7
- 239000004753 textile Substances 0.000 claims description 7
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 6
- 229940077388 benzenesulfonate Drugs 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229940071118 cumenesulfonate Drugs 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 125000005011 alkyl ether group Chemical group 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 2
- 150000001450 anions Chemical group 0.000 claims description 2
- 150000001805 chlorine compounds Chemical group 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- 235000011180 diphosphates Nutrition 0.000 claims description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims description 2
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
- 125000005341 metaphosphate group Chemical group 0.000 claims description 2
- OPUAWDUYWRUIIL-UHFFFAOYSA-L methanedisulfonate Chemical compound [O-]S(=O)(=O)CS([O-])(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-L 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 230000000249 desinfective effect Effects 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 18
- 235000014113 dietary fatty acids Nutrition 0.000 description 17
- 239000000194 fatty acid Substances 0.000 description 17
- 229930195729 fatty acid Natural products 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- 150000004665 fatty acids Chemical class 0.000 description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000003945 anionic surfactant Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000002091 cationic group Chemical group 0.000 description 8
- 239000002736 nonionic surfactant Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 150000002191 fatty alcohols Chemical class 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- BGRWYDHXPHLNKA-UHFFFAOYSA-N Tetraacetylethylenediamine Chemical compound CC(=O)N(C(C)=O)CCN(C(C)=O)C(C)=O BGRWYDHXPHLNKA-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229940088598 enzyme Drugs 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 238000004508 fractional distillation Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000003760 tallow Substances 0.000 description 5
- LRPJNWSVHROUBK-UHFFFAOYSA-N 2-(dioctylamino)acetonitrile Chemical compound CCCCCCCCN(CC#N)CCCCCCCC LRPJNWSVHROUBK-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 244000060011 Cocos nucifera Species 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 108010064470 polyaspartate Proteins 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- PTMNLAPQVWUAFM-UHFFFAOYSA-N 2-(dihexylamino)acetonitrile Chemical compound CCCCCCN(CC#N)CCCCCC PTMNLAPQVWUAFM-UHFFFAOYSA-N 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 108010084185 Cellulases Proteins 0.000 description 3
- 102000005575 Cellulases Human genes 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 229920000805 Polyaspartic acid Polymers 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UAOKXEHOENRFMP-ZJIFWQFVSA-N [(2r,3r,4s,5r)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate Chemical compound CC(=O)OC[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)C=O UAOKXEHOENRFMP-ZJIFWQFVSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 3
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 235000021438 curry Nutrition 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- COHOXCGHYWNNFN-UHFFFAOYSA-N methyl 2-propan-2-ylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1C(C)C COHOXCGHYWNNFN-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
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- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 3
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
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- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
-
- 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
- C11D3/3925—Nitriles; Isocyanates or quarternary ammonium nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
- C07C255/25—Aminoacetonitriles
-
- 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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10211389A DE10211389A1 (de) | 2002-03-15 | 2002-03-15 | Ammoniumnitrile und deren Verwendung als hydrophobe Bleichaktivatoren |
| DE10211389.0 | 2002-03-15 | ||
| PCT/EP2003/002543 WO2003078561A1 (de) | 2002-03-15 | 2003-03-12 | Ammoniumnitrile und deren verwendung als hydrophobe bleichaktivatoren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003219043A1 AU2003219043A1 (en) | 2003-09-29 |
| AU2003219043B2 true AU2003219043B2 (en) | 2008-06-12 |
Family
ID=27771315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003219043A Ceased AU2003219043B2 (en) | 2002-03-15 | 2003-03-12 | Ammonium nitriles and the use thereof as hydrophobic bleaching activators |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7015185B2 (enExample) |
| EP (1) | EP1487955B1 (enExample) |
| JP (1) | JP2005527531A (enExample) |
| KR (1) | KR20050002804A (enExample) |
| AU (1) | AU2003219043B2 (enExample) |
| BR (1) | BR0305214A (enExample) |
| CA (1) | CA2456927A1 (enExample) |
| DE (2) | DE10211389A1 (enExample) |
| ES (1) | ES2303895T3 (enExample) |
| WO (1) | WO2003078561A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004028494A1 (de) * | 2004-06-11 | 2005-12-29 | Clariant Gmbh | Mischungen von Ammoniumnitril-Bleichaktivatoren und Aminosäuren |
| DE102005005016A1 (de) | 2005-02-03 | 2006-08-10 | Basf Ag | Polymere hydrophobe Aminonitrilquats zur Bleichaktivierung |
| DE102005009136A1 (de) * | 2005-03-01 | 2006-09-07 | Clariant Produkte (Deutschland) Gmbh | Verbessertes Verfahren zur Herstellung von bifunktionellen Ammoniumnitrilen |
| DE102005009137A1 (de) * | 2005-03-01 | 2006-09-07 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von bifunktionellen Ammoniumnitrilen |
| JP2007172716A (ja) * | 2005-12-20 | 2007-07-05 | Sony Corp | 再生装置、再生方法および再生プログラム、記録媒体およびデータ構造、ならびに、オーサリング装置、オーサリング方法およびオーサリングプログラム |
| ATE530628T1 (de) * | 2006-03-22 | 2011-11-15 | Procter & Gamble | Waschzusammensetzung |
| DE102006013666A1 (de) * | 2006-03-24 | 2007-09-27 | Clariant International Limited | Verbessertes Verfahren zur Herstellung von natriumchloridfreien Ammoniumnitrilen |
| DE102006013665A1 (de) * | 2006-03-24 | 2007-09-27 | Clariant International Limited | Verbessertes Verfahren zur Herstellung von natriumchloridfreien Ammoniumnitrilen |
| DE102006028032A1 (de) * | 2006-06-14 | 2007-12-20 | Henkel Kgaa | Aufhell- und/oder Färbemittel mit Nitrilen |
| US8338353B2 (en) * | 2007-08-07 | 2012-12-25 | Arkema Inc. | Hard surface cleaner containing polysulfonic acid |
| US8124793B2 (en) * | 2007-11-27 | 2012-02-28 | Gail Marie Cronyn, legal representative | Derivatives of ethylene methanedisulfonate as cancer chemotherapeutic agents |
| WO2010118323A1 (en) * | 2009-04-10 | 2010-10-14 | Danisco Us Inc. | Cellulase-containing dish detergents |
| CN115494184B (zh) * | 2022-05-09 | 2023-07-28 | 浙江海正药业股份有限公司 | 一种同时检测药物中异丙苯磺酸甲酯、异丙苯磺酸乙酯的方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0303520A2 (en) * | 1987-08-14 | 1989-02-15 | Kao Corporation | Bleaching composition |
| EP0464880A1 (en) * | 1990-05-30 | 1992-01-08 | Unilever N.V. | Bleaching composition |
| CA2299437A1 (en) * | 1999-02-25 | 2000-08-25 | Henkel Kommanditgesellschaft Auf Aktien | Compounded acetonitrile derivatives as bleach activators in detergents |
| US6174853B1 (en) * | 1996-11-29 | 2001-01-16 | Basf Aktiengesellschaft | Textile detergent formulation on the basis of quaternized glycine nitriles, bleaching agents, nonionic and/or anionic tensides and calcium ion and/or magnesium ion sequestering compounds |
| US6225274B1 (en) * | 1996-11-29 | 2001-05-01 | Henkel Kommandigesellschaft Auf Aktien | Acetonitrile derivatives as bleaching activators in detergents |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1382594A (en) | 1971-06-04 | 1975-02-05 | Unilever Ltd | Quaternary ammonium compounds for use in bleaching systems |
| US4144226A (en) | 1977-08-22 | 1979-03-13 | Monsanto Company | Polymeric acetal carboxylates |
| US4146495A (en) | 1977-08-22 | 1979-03-27 | Monsanto Company | Detergent compositions comprising polyacetal carboxylates |
| US4751015A (en) | 1987-03-17 | 1988-06-14 | Lever Brothers Company | Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions |
| US4933103A (en) | 1987-03-23 | 1990-06-12 | Kao Corporation | Bleaching composition |
| GB9011618D0 (en) | 1990-05-24 | 1990-07-11 | Unilever Plc | Bleaching composition |
| DE4041752A1 (de) | 1990-12-24 | 1992-06-25 | Henkel Kgaa | Enzymzubereitung fuer wasch- und reinigungsmittel |
| DE4216774A1 (de) | 1992-05-21 | 1993-11-25 | Henkel Kgaa | Verfahren zur kontinuierlichen Herstellung eines granularen Wasch und/oder Reinigungsmittels |
| DE4310506A1 (de) | 1993-03-31 | 1994-10-06 | Cognis Bio Umwelt | Enzymzubereitung für Wasch- und Reinigungsmittel |
| US5856165A (en) | 1995-04-28 | 1999-01-05 | Genencor International | Alkaline cellulase and method of producing same |
| US6313081B1 (en) | 1995-04-28 | 2001-11-06 | Henkel Kommanditgesellschaft Auf Aktien (Kgaa) | Detergents comprising cellulases |
| DE19605526A1 (de) | 1996-02-15 | 1997-08-21 | Hoechst Ag | Ammoniumnitrile und deren Verwendung als Bleichaktivatoren |
| JP2002532615A (ja) * | 1998-12-15 | 2002-10-02 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | 漂白活性剤としてのアセトニトリル誘導体 |
| US20010046951A1 (en) * | 2000-02-02 | 2001-11-29 | Kao Corporation | Bleaching detergent composition |
-
2002
- 2002-03-15 DE DE10211389A patent/DE10211389A1/de not_active Withdrawn
-
2003
- 2003-03-12 ES ES03714809T patent/ES2303895T3/es not_active Expired - Lifetime
- 2003-03-12 EP EP03714809A patent/EP1487955B1/de not_active Expired - Lifetime
- 2003-03-12 WO PCT/EP2003/002543 patent/WO2003078561A1/de not_active Ceased
- 2003-03-12 AU AU2003219043A patent/AU2003219043B2/en not_active Ceased
- 2003-03-12 JP JP2003576556A patent/JP2005527531A/ja active Pending
- 2003-03-12 BR BR0305214-1A patent/BR0305214A/pt not_active IP Right Cessation
- 2003-03-12 US US10/486,939 patent/US7015185B2/en not_active Expired - Fee Related
- 2003-03-12 DE DE50309882T patent/DE50309882D1/de not_active Expired - Fee Related
- 2003-03-12 KR KR10-2004-7003126A patent/KR20050002804A/ko not_active Ceased
- 2003-03-12 CA CA002456927A patent/CA2456927A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0303520A2 (en) * | 1987-08-14 | 1989-02-15 | Kao Corporation | Bleaching composition |
| EP0464880A1 (en) * | 1990-05-30 | 1992-01-08 | Unilever N.V. | Bleaching composition |
| US6174853B1 (en) * | 1996-11-29 | 2001-01-16 | Basf Aktiengesellschaft | Textile detergent formulation on the basis of quaternized glycine nitriles, bleaching agents, nonionic and/or anionic tensides and calcium ion and/or magnesium ion sequestering compounds |
| US6225274B1 (en) * | 1996-11-29 | 2001-05-01 | Henkel Kommandigesellschaft Auf Aktien | Acetonitrile derivatives as bleaching activators in detergents |
| CA2299437A1 (en) * | 1999-02-25 | 2000-08-25 | Henkel Kommanditgesellschaft Auf Aktien | Compounded acetonitrile derivatives as bleach activators in detergents |
Non-Patent Citations (1)
| Title |
|---|
| DAVID B. LUTEN, JR: 'The preparation of Aminonitriles and their Quaternary Ammonium derivatives'. Journal of Organic Chemistry, no. 3, 1938, pages 588- 597. XP002245667. Page 592, example 28, table II. * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1487955B1 (de) | 2008-05-21 |
| KR20050002804A (ko) | 2005-01-10 |
| ES2303895T3 (es) | 2008-09-01 |
| CA2456927A1 (en) | 2003-09-25 |
| EP1487955A1 (de) | 2004-12-22 |
| US20040266644A1 (en) | 2004-12-30 |
| DE10211389A1 (de) | 2003-09-25 |
| US7015185B2 (en) | 2006-03-21 |
| BR0305214A (pt) | 2004-10-19 |
| AU2003219043A1 (en) | 2003-09-29 |
| DE50309882D1 (de) | 2008-07-03 |
| JP2005527531A (ja) | 2005-09-15 |
| WO2003078561A1 (de) | 2003-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TC | Change of applicant's name (sec. 104) |
Owner name: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH Free format text: FORMER NAME: CLARIANT GMBH |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |