CA1109757A - Detergent a faible teneur en phosphate - Google Patents
Detergent a faible teneur en phosphateInfo
- Publication number
- CA1109757A CA1109757A CA323,240A CA323240A CA1109757A CA 1109757 A CA1109757 A CA 1109757A CA 323240 A CA323240 A CA 323240A CA 1109757 A CA1109757 A CA 1109757A
- Authority
- CA
- Canada
- Prior art keywords
- moles
- composition according
- ethylene oxide
- alcohol
- condensation product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 242
- 239000003599 detergent Substances 0.000 title claims abstract description 43
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 22
- 239000010452 phosphate Substances 0.000 title claims abstract description 19
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000004744 fabric Substances 0.000 claims abstract description 61
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 60
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 59
- 239000000463 material Substances 0.000 claims abstract description 49
- 125000002091 cationic group Chemical group 0.000 claims abstract description 32
- 230000008901 benefit Effects 0.000 claims abstract description 30
- 230000003068 static effect Effects 0.000 claims abstract description 21
- 230000005764 inhibitory process Effects 0.000 claims abstract description 17
- 238000012546 transfer Methods 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 71
- 239000007859 condensation product Substances 0.000 claims description 65
- 239000004094 surface-active agent Substances 0.000 claims description 37
- -1 acetate anions Chemical group 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000001408 amides Chemical class 0.000 claims description 21
- 238000004140 cleaning Methods 0.000 claims description 17
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000000129 anionic group Chemical group 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 13
- WWYHAQDAMPXWSI-UHFFFAOYSA-N dodecan-1-ol;methane Chemical compound C.CCCCCCCCCCCCO WWYHAQDAMPXWSI-UHFFFAOYSA-N 0.000 claims description 11
- 229940096386 coconut alcohol Drugs 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- 239000003760 tallow Substances 0.000 claims description 8
- 238000010494 dissociation reaction Methods 0.000 claims description 7
- 230000005593 dissociations Effects 0.000 claims description 7
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- IYAQFFOKAFGDKE-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-3-ium;methyl sulfate Chemical compound C1CN=CN1.COS(O)(=O)=O IYAQFFOKAFGDKE-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 4
- 102000035195 Peptidases Human genes 0.000 claims description 4
- 108091005804 Peptidases Proteins 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 150000002193 fatty amides Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 239000010695 polyglycol Substances 0.000 claims description 4
- 229940120146 EDTMP Drugs 0.000 claims description 3
- 150000001450 anions Chemical group 0.000 claims description 3
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 claims description 3
- 229920000151 polyglycol Polymers 0.000 claims description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- KIDJHPQACZGFTI-UHFFFAOYSA-N [6-[bis(phosphonomethyl)amino]hexyl-(phosphonomethyl)amino]methylphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCCCCCN(CP(O)(O)=O)CP(O)(O)=O KIDJHPQACZGFTI-UHFFFAOYSA-N 0.000 claims description 2
- YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000001669 calcium Chemical class 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 229940090960 diethylenetriamine pentamethylene phosphonic acid Drugs 0.000 claims description 2
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 238000013019 agitation Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000002689 soil Substances 0.000 abstract description 30
- 238000004900 laundering Methods 0.000 abstract description 10
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 37
- 239000000975 dye Substances 0.000 description 19
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 16
- 229920001296 polysiloxane Polymers 0.000 description 14
- 235000021317 phosphate Nutrition 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 239000002304 perfume Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 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 5
- 238000009472 formulation Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 230000003750 conditioning effect Effects 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- 239000004064 cosurfactant Substances 0.000 description 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000004264 Petrolatum Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000004115 Sodium Silicate Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical class OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000004200 microcrystalline wax Substances 0.000 description 3
- 235000019808 microcrystalline wax Nutrition 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 229940066842 petrolatum Drugs 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 3
- 229910052911 sodium silicate Inorganic materials 0.000 description 3
- 235000019832 sodium triphosphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 241001553290 Euphorbia antisyphilitica Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 102000005158 Subtilisins Human genes 0.000 description 2
- 108010056079 Subtilisins Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000004203 carnauba wax Substances 0.000 description 2
- 235000013869 carnauba wax Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- AFYCEAFSNDLKSX-UHFFFAOYSA-N coumarin 460 Chemical compound CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 AFYCEAFSNDLKSX-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 239000003752 hydrotrope Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000012170 montan wax Substances 0.000 description 2
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 2
- 239000003605 opacifier Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 1
- GJFNNZBYCMUAHY-UHFFFAOYSA-N 2-(2-phenylethenyl)-1,3-benzoxazole Chemical class N=1C2=CC=CC=C2OC=1C=CC1=CC=CC=C1 GJFNNZBYCMUAHY-UHFFFAOYSA-N 0.000 description 1
- ABEOQSWLOAHSPF-UHFFFAOYSA-N 2-[2-(1,3-benzoxazol-2-yl)ethenyl]-1,3-benzoxazole Chemical class C1=CC=C2OC(C=CC=3OC4=CC=CC=C4N=3)=NC2=C1 ABEOQSWLOAHSPF-UHFFFAOYSA-N 0.000 description 1
- WFYSPVCBIJCZPX-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-yl)naphthalen-1-yl]-1,3-benzoxazole Chemical class C12=CC=CC=C2C(C=2OC3=CC=CC=C3N=2)=CC=C1C1=NC2=CC=CC=C2O1 WFYSPVCBIJCZPX-UHFFFAOYSA-N 0.000 description 1
- ORACIQIJMCYPHQ-UHFFFAOYSA-N 2-[4-[2-[4-(1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical class C1=CC=C2OC(C3=CC=C(C=C3)C=CC=3C=CC(=CC=3)C=3OC4=CC=CC=C4N=3)=NC2=C1 ORACIQIJMCYPHQ-UHFFFAOYSA-N 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
- SZWQPAIKUHNUMM-UHFFFAOYSA-N 5-tert-butyl-2-[4-[2-(4-phenylphenyl)ethenyl]phenyl]-1,3-benzoxazole Chemical compound N=1C2=CC(C(C)(C)C)=CC=C2OC=1C(C=C1)=CC=C1C=CC(C=C1)=CC=C1C1=CC=CC=C1 SZWQPAIKUHNUMM-UHFFFAOYSA-N 0.000 description 1
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- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- BJZLNMXZKIZLAW-UHFFFAOYSA-N C1CO1.[Na] Chemical compound C1CO1.[Na] BJZLNMXZKIZLAW-UHFFFAOYSA-N 0.000 description 1
- KUHLCPCIQYTVNN-UHFFFAOYSA-M CCO.C(C1=CC=CC=C1)S(=O)(=O)[O-].[Na+] Chemical compound CCO.C(C1=CC=CC=C1)S(=O)(=O)[O-].[Na+] KUHLCPCIQYTVNN-UHFFFAOYSA-M 0.000 description 1
- 101100489581 Caenorhabditis elegans par-5 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000004965 Silica aerogel Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002359 Tetronic® Polymers 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical group [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229940116335 lauramide Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FFJMLWSZNCJCSZ-UHFFFAOYSA-N n-methylmethanamine;hydrobromide Chemical compound Br.CNC FFJMLWSZNCJCSZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011012 sanitization Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 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
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000010457 zeolite Substances 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic compounds
- C11D1/8355—Mixtures of non-ionic with cationic compounds containing a combination of non-ionic compounds differently alcoxylised or with different alkylated chains
-
- 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
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic compounds
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0021—Dye-stain or dye-transfer inhibiting compositions
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
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)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88593178A | 1978-03-13 | 1978-03-13 | |
| US94341978A | 1978-09-18 | 1978-09-18 | |
| US943,419 | 1978-09-18 | ||
| US94918278A | 1978-10-06 | 1978-10-06 | |
| US949,182 | 1978-10-06 | ||
| US96282278A | 1978-11-22 | 1978-11-22 | |
| US962,822 | 1978-11-22 | ||
| US885,931 | 1992-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1109757A true CA1109757A (fr) | 1981-09-29 |
Family
ID=27505975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA323,240A Expired CA1109757A (fr) | 1978-03-13 | 1979-03-12 | Detergent a faible teneur en phosphate |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0004121A1 (fr) |
| AT (1) | ATA183079A (fr) |
| BE (1) | BE59T1 (fr) |
| BR (1) | BR7901558A (fr) |
| CA (1) | CA1109757A (fr) |
| CH (1) | CH644891A5 (fr) |
| DE (1) | DE2948921A1 (fr) |
| FR (1) | FR2446314A1 (fr) |
| GB (1) | GB2041968B (fr) |
| GR (1) | GR73580B (fr) |
| IT (1) | IT1148286B (fr) |
| NL (1) | NL7915015A (fr) |
| SE (1) | SE439494B (fr) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304610A (en) * | 1979-06-22 | 1981-12-08 | S. C. Johnson & Son, Inc. | Carpet cleaning method |
| EP0094118B2 (fr) * | 1982-05-10 | 1993-04-21 | THE PROCTER & GAMBLE COMPANY | Compositions détergentes pour le linge à faible teneur en phosphate |
| JPS598795A (ja) * | 1982-07-05 | 1984-01-18 | ライオン株式会社 | 粒状洗剤用添加剤 |
| EP0106692A1 (fr) * | 1982-10-18 | 1984-04-25 | THE PROCTER & GAMBLE COMPANY | Détergent liquide contenant du polyéthylène glycol |
| US4873002A (en) * | 1982-11-23 | 1989-10-10 | Beecham Inc. | Liquid detergent fabric conditioning compositions |
| US4497716A (en) * | 1982-12-23 | 1985-02-05 | Lever Brothers Company | Fabric softening composition |
| US4511490A (en) * | 1983-06-27 | 1985-04-16 | The Clorox Company | Cooperative enzymes comprising alkaline or mixtures of alkaline and neutral proteases without stabilizers |
| DE3402437A1 (de) | 1984-01-25 | 1985-07-25 | Rewo Chemische Werke Gmbh, 6497 Steinau | Pulverfoermiges waescheweichspuelmittel, verfahren zu seiner herstellung und diese enthaltendes waschmittel |
| GB8410320D0 (en) * | 1984-04-19 | 1984-05-31 | Unilever Plc | Aqueous fabric softening composition |
| GB8410321D0 (en) * | 1984-04-19 | 1984-05-31 | Unilever Plc | Aqueous concentrated fabric softening composition |
| GB2163771B (en) * | 1984-08-31 | 1989-01-18 | Colgate Palmolive Co | Wash cycle detergent-softener compositions |
| JPH02139480A (ja) * | 1988-11-21 | 1990-05-29 | Kao Corp | 柔軟仕上剤 |
| US5279772A (en) * | 1989-04-28 | 1994-01-18 | Ciba-Geigy Corporation | Liquid detergents containing specifically disulfonated dibenzofuranyl-biphenyls as flourescent whitening agents |
| DE4334368C2 (de) * | 1993-10-08 | 1995-12-14 | Henkel Kgaa | Schwach schäumende polymerfreie Reinigungsmittel |
| CA2132811A1 (fr) * | 1993-11-01 | 1995-05-02 | Beth T. G. Graubart | Liquide antimicrobien pour laver la vaisselle |
| CA2132274A1 (fr) * | 1993-11-01 | 1995-05-02 | Janet G. Gardella | Formulation liquide moussante antibacterienne pour le nettoyage des surfaces dans les cuisines |
| EP0687727B1 (fr) * | 1994-06-17 | 2001-01-17 | The Procter & Gamble Company | Compositions de blanchiment à base de mélanges d'agents tensio-actifs cationiques et non-ioniques |
| WO1999013833A1 (fr) * | 1997-09-17 | 1999-03-25 | The Procter & Gamble Company | Compositions pour le soin des cheveux comprenant des agents optiques de brillance et des composes cationiques |
| AU4419097A (en) * | 1997-09-17 | 1999-04-05 | Procter & Gamble Company, The | Hair care compositions comprising polystyrylstilbenes |
| WO1999013828A1 (fr) * | 1997-09-17 | 1999-03-25 | The Procter & Gamble Company | Compositions de schampooings comprenant des azurants optiques et une matrice de tensioactif doux |
| AU4483797A (en) * | 1997-09-17 | 1999-04-05 | Procter & Gamble Company, The | Shampoo compositions comprising optical brighteners and polyvalent cations |
| DE10059340A1 (de) * | 2000-11-29 | 2002-06-20 | Henkel Kgaa | Teilchenförmiges Textilnachbehandlungsmittel |
| GB0208696D0 (en) | 2002-04-16 | 2002-05-29 | Unilever Plc | Fabric treatment composition |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3812046A (en) * | 1970-11-18 | 1974-05-21 | Colgate Palmolive Co | Germicidal liquid cleaner |
| CA1059865A (fr) * | 1974-03-21 | 1979-08-07 | The Procter And Gamble Company | Detergents |
| JPS5914077B2 (ja) * | 1976-10-01 | 1984-04-03 | 花王株式会社 | 液体軽質洗剤組成物 |
| IT1097290B (it) * | 1977-06-29 | 1985-08-31 | Procter & Gamble | Composizioni detergenti per lavanderia |
| US4141841A (en) * | 1977-07-18 | 1979-02-27 | The Procter & Gamble Company | Antistatic, fabric-softening detergent additive |
-
1979
- 1979-03-10 BE BE79200120A patent/BE59T1/fr active
- 1979-03-10 EP EP79200120A patent/EP0004121A1/fr not_active Withdrawn
- 1979-03-10 DE DE19792948921 patent/DE2948921A1/de not_active Withdrawn
- 1979-03-10 NL NL7915015A patent/NL7915015A/nl unknown
- 1979-03-10 CH CH339080A patent/CH644891A5/de not_active IP Right Cessation
- 1979-03-10 GB GB8010130A patent/GB2041968B/en not_active Expired
- 1979-03-12 GR GR58583A patent/GR73580B/el unknown
- 1979-03-12 CA CA323,240A patent/CA1109757A/fr not_active Expired
- 1979-03-12 AT AT0183079A patent/ATA183079A/de unknown
- 1979-03-13 BR BR7901558A patent/BR7901558A/pt unknown
-
1980
- 1980-01-21 FR FR8001481A patent/FR2446314A1/fr active Granted
- 1980-02-13 SE SE8001135A patent/SE439494B/sv not_active IP Right Cessation
- 1980-03-18 IT IT86220/80A patent/IT1148286B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GB2041968A (en) | 1980-09-17 |
| IT1148286B (it) | 1986-11-26 |
| IT8086220A0 (it) | 1980-03-18 |
| GB2041968B (en) | 1982-11-03 |
| NL7915015A (nl) | 1980-05-30 |
| EP0004121A1 (fr) | 1979-09-19 |
| DE2948921A1 (de) | 1980-11-06 |
| FR2446314A1 (fr) | 1980-08-08 |
| SE439494B (sv) | 1985-06-17 |
| ATA183079A (de) | 1986-12-15 |
| BE59T1 (fr) | 1980-04-18 |
| FR2446314B1 (fr) | 1984-05-04 |
| GR73580B (fr) | 1984-03-21 |
| CH644891A5 (de) | 1984-08-31 |
| BR7901558A (pt) | 1979-10-16 |
| SE8001135L (sv) | 1980-02-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |