CA2324470A1 - Liquid laundry detergent compositions comprising hedp and polyamines - Google Patents
Liquid laundry detergent compositions comprising hedp and polyamines Download PDFInfo
- Publication number
- CA2324470A1 CA2324470A1 CA002324470A CA2324470A CA2324470A1 CA 2324470 A1 CA2324470 A1 CA 2324470A1 CA 002324470 A CA002324470 A CA 002324470A CA 2324470 A CA2324470 A CA 2324470A CA 2324470 A1 CA2324470 A1 CA 2324470A1
- Authority
- CA
- Canada
- Prior art keywords
- units
- polyamine
- alkylene
- mixtures
- alkyl
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 197
- 229920000768 polyamine Polymers 0.000 title claims abstract description 104
- 239000003599 detergent Substances 0.000 title claims abstract description 76
- 239000007788 liquid Substances 0.000 title claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 15
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 90
- -1 -(R1O)x B Substances 0.000 claims description 80
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 239000004094 surface-active agent Substances 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 150000001204 N-oxides Chemical class 0.000 claims description 17
- 239000005977 Ethylene Substances 0.000 claims description 16
- 230000004048 modification Effects 0.000 claims description 13
- 238000012986 modification Methods 0.000 claims description 13
- 150000001768 cations Chemical class 0.000 claims description 12
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 9
- 239000003945 anionic surfactant Substances 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 235000019256 formaldehyde Nutrition 0.000 claims 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- 229920002873 Polyethylenimine Polymers 0.000 description 47
- 102000004190 Enzymes Human genes 0.000 description 42
- 108090000790 Enzymes Proteins 0.000 description 42
- 229940088598 enzyme Drugs 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 35
- 108091005804 Peptidases Proteins 0.000 description 35
- 102000035195 Peptidases Human genes 0.000 description 35
- 125000000217 alkyl group Chemical group 0.000 description 34
- 239000000463 material Substances 0.000 description 34
- 239000000243 solution Substances 0.000 description 27
- 150000001412 amines Chemical class 0.000 description 26
- 108010065511 Amylases Proteins 0.000 description 25
- 102000013142 Amylases Human genes 0.000 description 25
- 235000019418 amylase Nutrition 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 25
- 239000000194 fatty acid Substances 0.000 description 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000004365 Protease Substances 0.000 description 21
- 235000014113 dietary fatty acids Nutrition 0.000 description 21
- 229930195729 fatty acid Natural products 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 19
- 239000011734 sodium Substances 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 229940025131 amylases Drugs 0.000 description 18
- 239000000975 dye Substances 0.000 description 18
- 239000002689 soil Substances 0.000 description 18
- 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 17
- 229920001296 polysiloxane Polymers 0.000 description 17
- 229920005646 polycarboxylate Polymers 0.000 description 16
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 16
- 238000012546 transfer Methods 0.000 description 16
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 15
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 15
- 150000004665 fatty acids Chemical class 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 230000003287 optical effect Effects 0.000 description 15
- 229920001223 polyethylene glycol Polymers 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 239000002202 Polyethylene glycol Substances 0.000 description 13
- 239000002738 chelating agent Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- 108090001060 Lipase Proteins 0.000 description 12
- 102000004882 Lipase Human genes 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000002270 dispersing agent Substances 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000004367 Lipase Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 238000004140 cleaning Methods 0.000 description 11
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 11
- 230000002401 inhibitory effect Effects 0.000 description 11
- 235000019421 lipase Nutrition 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 229910000323 aluminium silicate Inorganic materials 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 239000004382 Amylase Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 235000010338 boric acid Nutrition 0.000 description 9
- 108010020132 microbial serine proteinases Proteins 0.000 description 9
- 229920001451 polypropylene glycol Polymers 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000007844 bleaching agent Substances 0.000 description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 8
- 239000004327 boric acid Substances 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 230000001590 oxidative effect Effects 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 150000003335 secondary amines Chemical class 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 108010084185 Cellulases Proteins 0.000 description 7
- 102000005575 Cellulases Human genes 0.000 description 7
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 102000003992 Peroxidases Human genes 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000004927 clay Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- YGUMVDWOQQJBGA-VAWYXSNFSA-N 5-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C=1C=C(\C=C\C=2C(=CC(NC=3N=C(N=C(NC=4C=CC=CC=4)N=3)N3CCOCC3)=CC=2)S(O)(=O)=O)C(S(=O)(=O)O)=CC=1NC(N=C(N=1)N2CCOCC2)=NC=1NC1=CC=CC=C1 YGUMVDWOQQJBGA-VAWYXSNFSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 150000001413 amino acids Chemical group 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000002736 nonionic surfactant Substances 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
- 238000005956 quaternization reaction Methods 0.000 description 6
- 150000004760 silicates Chemical class 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910001424 calcium ion Inorganic materials 0.000 description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 238000007046 ethoxylation reaction Methods 0.000 description 5
- 230000002538 fungal effect Effects 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 5
- 239000002516 radical scavenger Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
- 150000003512 tertiary amines Chemical group 0.000 description 5
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical group NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000010457 zeolite Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241000193830 Bacillus <bacterium> Species 0.000 description 4
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 108700020962 Peroxidase Proteins 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 108010056079 Subtilisins Proteins 0.000 description 4
- 102000005158 Subtilisins Human genes 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 229910021536 Zeolite Inorganic materials 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
- 239000002979 fabric softener Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 238000003760 magnetic stirring Methods 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 239000002304 perfume Substances 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 150000003333 secondary alcohols Chemical class 0.000 description 4
- 229920002545 silicone oil Polymers 0.000 description 4
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 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
- 229910052720 vanadium Inorganic materials 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000194108 Bacillus licheniformis Species 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 102000004157 Hydrolases Human genes 0.000 description 3
- 108090000604 Hydrolases Proteins 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
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- BCXBKOQDEOJNRH-UHFFFAOYSA-N NOP(O)=O Chemical class NOP(O)=O BCXBKOQDEOJNRH-UHFFFAOYSA-N 0.000 description 3
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- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
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- 108090000637 alpha-Amylases Proteins 0.000 description 3
- 102000004139 alpha-Amylases Human genes 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229960001484 edetic acid Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004900 laundering Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910001425 magnesium ion Inorganic materials 0.000 description 3
- 159000000003 magnesium salts Chemical class 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 108010075550 termamyl Proteins 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
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- 239000011574 phosphorus Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 235000019351 sodium silicates Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 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
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical compound CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/36—Organic compounds containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3723—Polyamines or polyalkyleneimines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/36—Organic compounds containing phosphorus
- C11D3/361—Phosphonates, phosphinates or phosphonites
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3792—Amine oxide containing polymers
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98870057.1 | 1998-03-23 | ||
| EP98870057A EP0945500A1 (en) | 1998-03-23 | 1998-03-23 | Liquid laundry detergent compositions comprising HEDP and polyamines |
| PCT/IB1999/000470 WO1999049009A1 (en) | 1998-03-23 | 1999-03-22 | Liquid laundry detergent compositions comprising hedp and polyamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2324470A1 true CA2324470A1 (en) | 1999-09-30 |
Family
ID=8237011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002324470A Abandoned CA2324470A1 (en) | 1998-03-23 | 1999-03-22 | Liquid laundry detergent compositions comprising hedp and polyamines |
Country Status (11)
| Country | Link |
|---|---|
| EP (2) | EP0945500A1 (cs) |
| JP (1) | JP2002507659A (cs) |
| KR (1) | KR100386760B1 (cs) |
| CN (1) | CN1227344C (cs) |
| AR (1) | AR019013A1 (cs) |
| AU (1) | AU750087B2 (cs) |
| BR (1) | BR9908963B1 (cs) |
| CA (1) | CA2324470A1 (cs) |
| CZ (1) | CZ20003296A3 (cs) |
| MA (1) | MA24784A1 (cs) |
| WO (1) | WO1999049009A1 (cs) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1408103A1 (en) * | 2002-10-10 | 2004-04-14 | N.V. Solutia Europe S.A. | Detergent composition exhibiting enhanced stain removal |
| US7018968B2 (en) | 2003-09-17 | 2006-03-28 | Unilever Home & Personal Care Usa | Liquid laundry detergent with polyanionic ammonium surfactant |
| US7037883B2 (en) | 2003-09-17 | 2006-05-02 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Process of making a liquid laundry detergent with polyanionic ammonium surfactant |
| US6969700B2 (en) | 2004-02-12 | 2005-11-29 | Unilever Home & Personal Care, Usa Division Of Conopco, Inc | Liquid detergent with polyanionic ammonium surfactant and a high pKa solid inorganic base |
| DE102004015401A1 (de) | 2004-03-26 | 2005-10-20 | Henkel Kgaa | Maschinelles Geschirrspülmittel |
| US7387992B2 (en) | 2005-03-15 | 2008-06-17 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Laundry detergent with polyamine mono-anionic surfactant |
| US9376648B2 (en) | 2008-04-07 | 2016-06-28 | The Procter & Gamble Company | Foam manipulation compositions containing fine particles |
| BR112013001221A2 (pt) * | 2010-07-01 | 2016-06-07 | Unilever Nv | produto embalado para limpeza de tecidos e método para limpar um tecido |
| EP2794833B1 (en) | 2011-12-20 | 2016-02-03 | Unilever Plc. | Isotropic aqueous liquid laundry detergent comprising sequestrant |
| US10060073B2 (en) * | 2013-05-23 | 2018-08-28 | Washing Systems, Llc | Method of laundering industrial garments |
| CN103704264B (zh) * | 2014-01-09 | 2016-04-20 | 南通思锐生物科技有限公司 | 一种消毒清洁剂 |
| WO2016069774A1 (en) | 2014-10-28 | 2016-05-06 | Agrivida, Inc. | Methods and compositions for stabilizing trans-splicing intein modified proteases |
| US12116193B2 (en) * | 2015-12-02 | 2024-10-15 | Nippon Shokubai Co., Ltd. | Water-soluble film and manufacturing method therefor |
| CN109563452B (zh) * | 2016-09-07 | 2021-11-30 | 埃科莱布美国股份有限公司 | 含有由膦酸稳定的酶的洗涤剂组合物 |
| DE102018217984A1 (de) | 2018-10-22 | 2020-04-23 | Henkel Ag & Co. Kgaa | Neuartige Polyalkyleniminderivate und Wasch- und Reinigungsmittel, die solche enthalten |
| US12281283B2 (en) * | 2019-10-11 | 2025-04-22 | The Procter & Gamble Company | Method of laundering fabric |
| DE102020212099A1 (de) * | 2020-09-25 | 2022-03-31 | Henkel Ag & Co. Kgaa | Konzentrierte fließfähige Waschmittelzubereitung mit verbesserten Eigenschaften |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2285052A (en) * | 1993-12-23 | 1995-06-28 | Procter & Gamble | Detergent composition |
| WO1997042291A1 (en) * | 1996-05-03 | 1997-11-13 | The Procter & Gamble Company | Detergent compositions comprising modified polyamines as dye transfer inhibitors |
| US5858948A (en) * | 1996-05-03 | 1999-01-12 | Procter & Gamble Company | Liquid laundry detergent compositions comprising cotton soil release polymers and protease enzymes |
| CA2252883A1 (en) * | 1996-05-03 | 1997-11-13 | Chanchal Kumar Ghosh | Detergent compositions comprising polyamine scavenger agents and enzymes |
| BR9710658A (pt) * | 1996-05-03 | 1999-08-17 | Procter & Gamble | Composi-{es detergentes l¡quidas de lavanderia compreendendo pol¡meros de libera-Æo de sujeira de algodÆo |
| EP0924293B2 (en) * | 1997-11-24 | 2009-11-11 | The Procter & Gamble Company | Use of a crystal growth inhibitor to reduce fabric abrasion |
-
1998
- 1998-03-23 EP EP98870057A patent/EP0945500A1/en not_active Withdrawn
-
1999
- 1999-03-22 CA CA002324470A patent/CA2324470A1/en not_active Abandoned
- 1999-03-22 CN CNB998043672A patent/CN1227344C/zh not_active Expired - Fee Related
- 1999-03-22 EP EP99942590A patent/EP1086200A1/en not_active Withdrawn
- 1999-03-22 WO PCT/IB1999/000470 patent/WO1999049009A1/en active IP Right Grant
- 1999-03-22 BR BRPI9908963-7A patent/BR9908963B1/pt not_active IP Right Cessation
- 1999-03-22 JP JP2000537971A patent/JP2002507659A/ja active Pending
- 1999-03-22 KR KR10-2000-7010527A patent/KR100386760B1/ko not_active Expired - Fee Related
- 1999-03-22 CZ CZ20003296A patent/CZ20003296A3/cs unknown
- 1999-03-22 AU AU32697/99A patent/AU750087B2/en not_active Ceased
- 1999-03-23 MA MA25505A patent/MA24784A1/fr unknown
- 1999-03-23 AR ARP990101283A patent/AR019013A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999049009A1 (en) | 1999-09-30 |
| CN1294627A (zh) | 2001-05-09 |
| AR019013A1 (es) | 2001-12-26 |
| BR9908963B1 (pt) | 2010-07-13 |
| JP2002507659A (ja) | 2002-03-12 |
| KR20010034635A (ko) | 2001-04-25 |
| MA24784A1 (fr) | 1999-10-01 |
| BR9908963A (pt) | 2000-12-05 |
| CN1227344C (zh) | 2005-11-16 |
| EP0945500A1 (en) | 1999-09-29 |
| AU750087B2 (en) | 2002-07-11 |
| KR100386760B1 (ko) | 2003-06-09 |
| CZ20003296A3 (cs) | 2001-10-17 |
| EP1086200A1 (en) | 2001-03-28 |
| AU3269799A (en) | 1999-10-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |