EP0184099A2 - Moyen et procédé pour le post-traitement du linge lavé - Google Patents
Moyen et procédé pour le post-traitement du linge lavé Download PDFInfo
- Publication number
- EP0184099A2 EP0184099A2 EP85114926A EP85114926A EP0184099A2 EP 0184099 A2 EP0184099 A2 EP 0184099A2 EP 85114926 A EP85114926 A EP 85114926A EP 85114926 A EP85114926 A EP 85114926A EP 0184099 A2 EP0184099 A2 EP 0184099A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- percent
- salts
- quaternary ammonium
- composition according
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 5
- 230000008569 process Effects 0.000 title claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 36
- -1 hexafluorosilicic acid Chemical compound 0.000 claims abstract description 25
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 239000002535 acidifier Substances 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 9
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 159000000003 magnesium salts Chemical class 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 17
- 239000004753 textile Substances 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 229910001385 heavy metal Inorganic materials 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 239000008139 complexing agent Substances 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 8
- 239000002270 dispersing agent Substances 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000003599 detergent Substances 0.000 claims description 6
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000000845 anti-microbial effect Effects 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- 239000004902 Softening Agent Substances 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 230000002378 acidificating effect Effects 0.000 abstract description 5
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 6
- 235000011007 phosphoric acid Nutrition 0.000 description 6
- 239000000470 constituent Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000004599 antimicrobial Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 150000008043 acidic salts Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- GPCTYPSWRBUGFH-UHFFFAOYSA-N (1-amino-1-phosphonoethyl)phosphonic acid Chemical compound OP(=O)(O)C(N)(C)P(O)(O)=O GPCTYPSWRBUGFH-UHFFFAOYSA-N 0.000 description 1
- LNPHVNNRZGCOBK-UHFFFAOYSA-N 2-(dodecylazaniumyl)acetate Chemical compound CCCCCCCCCCCCNCC(O)=O LNPHVNNRZGCOBK-UHFFFAOYSA-N 0.000 description 1
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 description 1
- PTFSLTXIXFNFSI-UHFFFAOYSA-N 2-[bis(2-aminoethyl)amino]tetradecanoic acid Chemical compound CCCCCCCCCCCCC(C(O)=O)N(CCN)CCN PTFSLTXIXFNFSI-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical group OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical group NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 1
- 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 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- XJOBGSAVAQWWLT-UHFFFAOYSA-M [Cl-].C(C)[N+](CCCCCCCCCCCC)(CCN(CC)CC)CC=CC Chemical compound [Cl-].C(C)[N+](CCCCCCCCCCCC)(CCN(CC)CC)CC=CC XJOBGSAVAQWWLT-UHFFFAOYSA-M 0.000 description 1
- DORXOBNHTCLHGA-UHFFFAOYSA-N [Cl-].[NH4+].Cl.C(C)NCC Chemical compound [Cl-].[NH4+].Cl.C(C)NCC DORXOBNHTCLHGA-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- KXEMXOYVVPLGSD-UHFFFAOYSA-N benzene-1,3-dicarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC(C(=O)OO)=C1 KXEMXOYVVPLGSD-UHFFFAOYSA-N 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- HUSDIEGEFWRTIN-UHFFFAOYSA-M benzyl-decyl-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 HUSDIEGEFWRTIN-UHFFFAOYSA-M 0.000 description 1
- OCBHHZMJRVXXQK-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 OCBHHZMJRVXXQK-UHFFFAOYSA-M 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- LUNQZVCDZKODKF-PFVVTREHSA-L copper acetic acid (2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoate (2S)-6-amino-2-[[(2S)-2-[(2-amino-1-oxidoethylidene)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoate hydron Chemical compound [Cu+2].CC(O)=O.CC(O)=O.NCCCC[C@@H](C([O-])=O)NC(=O)[C@@H](NC(=O)CN)CC1=CN=CN1.NCCCC[C@@H](C([O-])=O)NC(=O)[C@@H](NC(=O)CN)CC1=CN=CN1 LUNQZVCDZKODKF-PFVVTREHSA-L 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- VECSBAZNSDLLDQ-UHFFFAOYSA-M dodecyl-dimethyl-(1-phenylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C(CC)C1=CC=CC=C1 VECSBAZNSDLLDQ-UHFFFAOYSA-M 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 108010038983 glycyl-histidyl-lysine Proteins 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical compound OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- SXLLDUPXUVRMEE-UHFFFAOYSA-N nonanediperoxoic acid Chemical compound OOC(=O)CCCCCCCC(=O)OO SXLLDUPXUVRMEE-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical class OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 150000003751 zinc Chemical class 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
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3947—Liquid 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
- C11D1/38—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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/042—Acids
-
- 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
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/046—Salts
-
- 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
- C11D3/3937—Stabilising agents
Definitions
- the laundry treatment generally requires several operations for "acidifying” (neutralizing) and “antichlorinating” (reducing) as well as softening or antibacterial treatment.
- Agents and processes with which acidification and antichlorination of freshly washed laundry * as well as post-treatment with textile softeners or antibacterial agents can be carried out in a single operation are therefore a considerable disadvantage of the post-washing treatment for commercial laundries.
- liquid aftertreatment agents which can be produced, for example, by dissolving powdery agents into a stock solution, usually fails because of the poor solubility or the insufficient stability of the solution or dispersion of the - because of the metering devices for liquid agents usually present on commercial washing machines known aftertreatment agents intended for use in commercial laundries.
- Known liquid agents do not have acidifying, antichlorinating and softening properties at the same time.
- DE-OS 32 05 317 describes a liquid laundry aftertreatment agent which simultaneously combines textile softening, acidifying and antichlorinating properties.
- the textile treatment agents disclosed here contain, in addition to quaternary ammonium compounds with textile softening action, hydrogen peroxide or organic percarboxylic acids as reducing agents for chlorine and chlorine compounds with positive value and additionally stabilizers for the peroxy compounds, especially the hydrogen peroxide.
- acidifying agents in particular phosphoric acid or acidic salts of phosphoric acid, but also other inorganic and / or organic acids or salts
- the pH of the agent is lowered so that it is at most 4.
- These agents of DE-OS 32 05 317 can also contain other usual additives, for example antibacterial agents. Examples of other additives are dispersants, foam regulators, and colorants and fragrances. Water may be used as the liquid carrier, with additions of organic water-miscible solvents.
- the invention is based on the task of further improving the means described last.
- the invention aims to extend the shelf life and thus the useful life of such agents.
- the substance mixtures of the type described contain per-compounds, in particular hydrogen peroxide, as an essential constituent.
- hydrogen peroxide quaternary ammonium compounds and an acidic agent, in particular phosphoric acid or phosphoric acid salts
- an acidic agent in particular phosphoric acid or phosphoric acid salts
- the invention relates in a first embodiment to liquid laundry aftertreatment agents with textile-softening, acidifying and antichlorizing properties, containing hydrogen peroxide or an organic percarboxylic acid, stabilizers for peroxy compounds, textile-softening quaternary ammonium compounds and acidifying agents and, if desired, other additives which are customary .
- the new teaching is characterized in that hexafluorosilicic acid and / or its water-soluble salts are present at least partially as acidifying agents.
- the amount of hexafluorosilicic acid and / or its water-soluble salts in the laundry treatment composition is preferably about 1 to 25 percent by weight, in particular about 5 to 20 percent by weight.
- the hexafluorosilicic acid or its salts are the sole or predominant constituent for acidifying the treatment agent, it also being preferred here not to set pH values above 4 in the aqueous aftertreatment agent.
- Suitable water-soluble salts of hexafluorosilicic acid are, for example, corresponding salts from the first to third groups of the periodic system, the ammonium salt of the acid mentioned or the corresponding amine and / or quaternary ammonium salts.
- particularly suitable acidifying components can be their sodium, potassium and / or ammonium salts, the magnesium and / or zinc salt, the magnesium salt being preferred because of its excellent acidifying and peroxide-stabilizing action.
- Particularly suitable amounts of these acidifying agents are in the range from about 8 to 18 weight percent.
- the quaternary ammonium compounds with preferably two long-chain, preferably saturated aliphatic radicals each having 14 to 26, preferably 16 to 20 carbon atoms and at least one quaternary nitrogen atom in the molecule are suitable as fabric softening agents.
- the long-chain aliphatic radicals can be straight-chain or branched and can accordingly be derived from fatty acids, or from fatty amines, Guerbetamines, or from the alkylamines obtainable by reduction of nitroparaffins.
- These quaternary ammonium compounds are, in particular, derivatives of ammonia, ie the quaternary salts obtainable by alkylation of long-chain secondary amines, such as, for. B. the compounds distearyldimethylammonium chloride or di.
- the tallow alkyl dimethyl ammonium chloride or the imidazoline compounds obtainable by reacting 1 mole of an aminoalkyl ethylenediamine or hydroxyalkyl ethylenediamine with 2 moles of a long-chain C 12 -C 26 fatty acid or its ester, which are then converted into the quaternary imidazolinium compounds by alkylation.
- the anion generally consists of the acid residue which has arisen from the alkylating agent used in the quaternization.
- chloride, bromide, methyl sulfate, ethyl sulfate, methane, ethane or toluenesulfonate are suitable as anions.
- the condensates of 1-3 mols of fatty acid alkyl ester or 1/3-1 mol of fatty acid triglyceride with 1Nol of a hydroxyalkylpolyamine, for example hydroxyethylethylenediamine or hydroxyethyldiethyle-n-triamine are also suitable as fabric softeners. Particularly suitable is obtained by reacting 1 mol of a fatty acid triglyceride, particularly hydrogenated tallow, with 1 mol of hydroxyethylethylene d.iamin at 90-150 C d available product.
- These active ingredients lead to a uniform, striking improvement in the treated textiles with simultaneous antistatic finishing without staining.
- the agent according to the invention preferably contains hydrogen peroxide (H 2 O 2 ) as an antichlorinating component.
- H 2 O 2 acts as a reducing agent compared to the stronger oxidizing agent hypochlorite.
- organic percarboxylic acids such as. B. diperazelaic acid or diperisophthalic acid can be used.
- the hydrogen peroxide is preferred because of its easy accessibility and because it is converted to the water which is present anyway upon reduction. Another advantage of H 2 O 2 is that it cannot form any solid deposits.
- the agent contains a heavy metal complexing agent.
- Suitable complexing agents are e.g. B. alkane polyphosphonic acids, amino and hydroxyalkane polyphosphonic acids and phosphonocarboxylic acids, such as. B. the compounds methanediphosphonic acid, 1-aminoethane-1,1-diphosphonic acid, aminotrimethylene triphosphonic acid, 2-phosphonobutane-1,2,4-tricarboxylic acid and 1-hydroxyethane-1,1-diphosphonic acid or aminopolycarboxylic acids such as. B.
- nitrilotriacetic acid ethylenediaminetetraacetic acid or hydroxyethylethylenediaminetriacetic acid or its alkali metal salts.
- Such heavy metal complexing agents also counteract a yellowing tendency of the laundry caused by heavy metal ions in the rinse water.
- 1-Hydroxyethane-1,1-diphosphonic acid and its alkali salts have a particularly good stabilizing effect.
- inorganic and / or organic acids or corresponding acid salts can also be used. Especially when working with hydrogen peroxide, the choice of additional acids or acid salts is preferred, which do not in turn interact with the peroxide.
- Orthophosphoric acid and / or its acidic salts for example sodium dihydrogen phosphate, are particularly suitable.
- the agents according to the invention can contain customary further additives.
- Antimicrobial agents are an example of this.
- bactericidal or bacteriostatic or fungicidal or fungistatic compounds are understood. These active ingredients are said to be water-soluble either as such or in the form of their salts.
- the antimicrobial agents suitable as additives are e.g. For example, such quaternary ammonium compounds which, in addition to a long-chain aliphatic and two short-chain aliphatic hydrocarbon radicals, contain an aromatic radical linked via an aliphatic carbon atom to the nitrogen atom, or an aliphatic organic radical having double bonds in the molecule.
- antimicrobial quaternary ammonium compounds are the following: dimethyl-benzyl-dodecylammonium chloride, dimethyl-benzyl-tetradecylammonium chloride, dimethyl- (ethylbenzyl) -dodecyl-ammonium chloride, dimethyl-benzyl-decylammonium bromide, diethyl-benzyl-dodecylammylium diethylammonium ammonium chloride, dibutylallyl, methyl-ethyl-benzyl, ethyl-cyclohexyl-allyl, ethyl-crotyl-diethylaminoethyl-dodecyl-ammonium chloride and in particular cocoalkyldimethylbenzylammonium chloride. Dimethyldidecylammonium chloride is also effective.
- antimicrobial agents can also be used, provided they are stable in the presence of per compounds in an acidic medium.
- betaines such as. B. Dodecyl-di (aminoethyl) glycine.
- Other useful antimicrobial agents are e.g. B. hexamethylene bis (chlorophenyl) biguanide digluconate or dihydrochloride and dodecylglycine.
- nonionic surfactants are particularly suitable as dispersants, as they can be contained in liquid textile aftertreatment agents according to the invention. These include products that owe their hydrophilic properties to the presence of polyether chains, amine oxide, sulfoxide or phosphine oxide groups, alkylolar groups or, in general, an accumulation of hydroxyl groups.
- nonionics contain at least one hydrophobic radical with 8-26, preferably 10-20 and in particular 12-18 carbon atoms in the molecule, and at least one nonionic, water-solubilizing group.
- the preferably saturated hydrophobic residue is usually aliphatic, possibly also alicyclic in nature; it can be connected to the water-solubilizing groups directly or via intermediate links.
- intermediate links come z. B. benzene rings, carboxylic acid ester or carbonamide groups, ether or ester-bonded residues of polyhydric alcohols, such as. B. that of ethylene glycol, propylene glycol, glycerol or corresponding polyether radicals in question.
- Typical nonionics preferred as dispersants are e.g. B. the adducts of about 9 moles of ethylene oxide with N o -nylphenol or with dodecyl alcohol, polyethylene glycols up to 50-ethoxy units or polyethoxy-polypropoxy-glycols with up to 20 ethoxy or propoxy units.
- quaternary ammonium compound which softens the textile preference is given in particular to the compounds which are used to a large extent, dimethylditalgalkylammonium chloride or dimethyldistearylammonium chloride, of which dirzethyldistearylammonium chloride is particularly preferred.
- Quaternary ammonium compounds are preferred as antibacterial active substances, in particular coconut alkyldimethylbenzylammonium chloride.
- Hydrogen peroxide which has sufficient stability in the presence of heavy metal complexing agents, is used in particular for the antichlorination.
- Suitable heavy metal complexing agents by means of which both the hydrogen peroxide is stabilized and discoloration of the laundry is counteracted by the use of washing water and rinsing water with an intrinsically disruptive content of heavy metal ions, are above all alkane polyphosphonic acids and aminopolycarboxylic acids, especially hydroxyethylenediamino-t R acetic acid and / or 1-hydroxyethanl, 1-diphosphonic acid b between their alkali salts.
- Agents according to the invention contain especially when large amounts of textile-softening quaternary ammonium compounds are used to achieve a pronounced softening effect, expediently small amounts, for example 0.5-5% by weight of nonionic surfactants as dispersants.
- This substance mixture which corresponds to the teaching of DE-OS 32 05 317, is compared with regard to its degree of hydrogen peroxide conservation during storage for 12 weeks at 40 ° C. compared to the active substance mixtures according to the invention summarized in the following table under numbers 2 to 5.
- magnesium hexafluorosilicate! Is used as an acidifying agent.
- the superior effect of the active ingredient mixtures according to the invention with regard to the degree of H 2 0 2 conservation after storage at 40 ° C. for 12 weeks can be seen from the corresponding numerical values.
- the numerical values of the mixtures according to 2, 4, 5 and 6 are in the range 79-88% H 2 0 2 Conservation compared to 28.5% for the active ingredient mixture according to the prior art.
- Even the active ingredient mixture 3 used for comparison which contains no complexing agent but contains magnesium fluorosilicate, is still significantly better in terms of the H 2 0 2 degree of preservation than the substance mixture of the prior art used for comparison.
- the active ingredient mixtures according to the invention are generally placed in the last rinsing bath of a commercial washing machine - depending on the implementation of the previous washing process, i.e. of the remaining residual alkali or the desired softening or microbicidal effect - in an amount of 1 to 5 g / l to the rinse water (temperature approx. 25 ° C) and treat the washed and bleached with hypochlorite laundry for approx. 2 minutes. After this treatment liquor has been spun off, it can be determined by measuring the pH of the adhering moisture that alkaline detergent residues on the laundry are neutralized. The laundry does not smell of chlorine. After drying, it has a soft full grip.
Landscapes
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
- Treatment Of Fiber Materials (AREA)
- Devices For Medical Bathing And Washing (AREA)
- Inorganic Insulating Materials (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Control Of Washing Machine And Dryer (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT85114926T ATE59677T1 (de) | 1984-12-03 | 1985-11-25 | Mittel und verfahren zum nachbehandeln gewaschener waesche. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3444068 | 1984-12-03 | ||
DE19843444068 DE3444068A1 (de) | 1984-12-03 | 1984-12-03 | Mittel und verfahren zum nachbehandeln gewaschener waesche |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0184099A2 true EP0184099A2 (fr) | 1986-06-11 |
EP0184099A3 EP0184099A3 (en) | 1988-05-25 |
EP0184099B1 EP0184099B1 (fr) | 1991-01-02 |
Family
ID=6251782
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP85114926A Expired - Lifetime EP0184099B1 (fr) | 1984-12-03 | 1985-11-25 | Moyen et procédé pour le post-traitement du linge lavé |
Country Status (7)
Country | Link |
---|---|
US (1) | US4704212A (fr) |
EP (1) | EP0184099B1 (fr) |
JP (1) | JPS61138770A (fr) |
AT (1) | ATE59677T1 (fr) |
DE (2) | DE3444068A1 (fr) |
DK (1) | DK551885A (fr) |
ES (1) | ES8706811A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0288812B1 (fr) * | 1987-04-30 | 1991-08-07 | Hoechst Aktiengesellschaft | Usage d'un inhibiteur de corrosion sur les surfaces céramiques |
WO1994000548A1 (fr) * | 1992-06-19 | 1994-01-06 | Laporte E.S.D. Limited | Compositions contenant un peracide organique et un compose d'ammonium quaternaire |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8822206D0 (en) * | 1988-09-21 | 1988-10-26 | Unilever Plc | Fabric treatment composition |
US5173214A (en) * | 1989-02-01 | 1992-12-22 | Union Oil Company Of California | Precursor composition for sols and gels |
DE4111040C1 (fr) * | 1991-04-05 | 1992-06-17 | Deutsche Granini Gmbh & Co Kg, 4800 Bielefeld, De | |
GB2285051A (en) * | 1993-12-23 | 1995-06-28 | Procter & Gamble | Rinse aid composition |
US5460736A (en) * | 1994-10-07 | 1995-10-24 | The Procter & Gamble Company | Fabric softening composition containing chlorine scavengers |
BR9612623A (pt) * | 1995-06-07 | 1999-05-25 | Bio Lab Inc | Tratamento de água com peróxide de hidrogênio e um estabilizador de amônio quaternário |
US6262013B1 (en) | 1999-01-14 | 2001-07-17 | Ecolab Inc. | Sanitizing laundry sour |
US6436445B1 (en) | 1999-03-26 | 2002-08-20 | Ecolab Inc. | Antimicrobial and antiviral compositions containing an oxidizing species |
US6855328B2 (en) * | 2002-03-28 | 2005-02-15 | Ecolab Inc. | Antimicrobial and antiviral compositions containing an oxidizing species |
BRPI0416067A (pt) * | 2003-10-29 | 2007-01-02 | Mallinckrodt Baker Inc | removedores alcalinos de resìduo de cinza/gravação pós-plasma e composições de descascamento de fotorresistes contendo inibidores de corrosão de haleto de metal |
US9228158B2 (en) * | 2012-02-01 | 2016-01-05 | Gurtler Industries, Inc. | Composition and method for removing stains derived from chlorhexidine gluconate |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3329609A (en) * | 1965-03-22 | 1967-07-04 | Wyandotte Chemicals Corp | Compositions containing quaternary ammonium salts |
US4115281A (en) * | 1975-01-30 | 1978-09-19 | Basf Wyandotte Corporation | Compositions for souring and softening laundered textile materials, method of preparing the same, and stock solutions prepared therefrom |
DE3142767A1 (de) * | 1980-10-28 | 1982-07-08 | Société d'Applications de Procédés Industriels et Chimiques S.A.P.I.C., 92600 Asnières, Seine | Stabilisierte waessrige wasserstoffperoxidloesungen und verfahren zu ihrer herstellung |
EP0086423A2 (fr) * | 1982-02-15 | 1983-08-24 | Henkel Kommanditgesellschaft auf Aktien | Moyen et procédé pour le posttraitement du linge lavé |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3193505A (en) * | 1961-09-20 | 1965-07-06 | Wyandotte Chemicals Corp | Antimicrobial laundry sour composition |
US3676353A (en) * | 1971-02-16 | 1972-07-11 | Basf Wyandotte Corp | Nonflouride laundry sour containing fumaric acid |
US3925230A (en) * | 1973-12-26 | 1975-12-09 | Procter & Gamble | Non-caking laundry sour |
US3984335A (en) * | 1975-01-16 | 1976-10-05 | Basf Wyandotte Corporation | Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom |
DE2904876A1 (de) * | 1979-02-09 | 1980-08-21 | Henkel Kgaa | Mittel und verfahren zum nachbehandeln gewaschener waesche |
-
1984
- 1984-12-03 DE DE19843444068 patent/DE3444068A1/de not_active Withdrawn
-
1985
- 1985-11-25 AT AT85114926T patent/ATE59677T1/de active
- 1985-11-25 DE DE8585114926T patent/DE3581068D1/de not_active Expired - Fee Related
- 1985-11-25 EP EP85114926A patent/EP0184099B1/fr not_active Expired - Lifetime
- 1985-11-28 DK DK551885A patent/DK551885A/da not_active Application Discontinuation
- 1985-12-02 US US06/803,363 patent/US4704212A/en not_active Expired - Fee Related
- 1985-12-03 ES ES549515A patent/ES8706811A1/es not_active Expired
- 1985-12-03 JP JP60273180A patent/JPS61138770A/ja active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3329609A (en) * | 1965-03-22 | 1967-07-04 | Wyandotte Chemicals Corp | Compositions containing quaternary ammonium salts |
US4115281A (en) * | 1975-01-30 | 1978-09-19 | Basf Wyandotte Corporation | Compositions for souring and softening laundered textile materials, method of preparing the same, and stock solutions prepared therefrom |
DE3142767A1 (de) * | 1980-10-28 | 1982-07-08 | Société d'Applications de Procédés Industriels et Chimiques S.A.P.I.C., 92600 Asnières, Seine | Stabilisierte waessrige wasserstoffperoxidloesungen und verfahren zu ihrer herstellung |
EP0086423A2 (fr) * | 1982-02-15 | 1983-08-24 | Henkel Kommanditgesellschaft auf Aktien | Moyen et procédé pour le posttraitement du linge lavé |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0288812B1 (fr) * | 1987-04-30 | 1991-08-07 | Hoechst Aktiengesellschaft | Usage d'un inhibiteur de corrosion sur les surfaces céramiques |
WO1994000548A1 (fr) * | 1992-06-19 | 1994-01-06 | Laporte E.S.D. Limited | Compositions contenant un peracide organique et un compose d'ammonium quaternaire |
Also Published As
Publication number | Publication date |
---|---|
JPS61138770A (ja) | 1986-06-26 |
DK551885A (da) | 1986-06-04 |
ATE59677T1 (de) | 1991-01-15 |
ES8706811A1 (es) | 1987-07-01 |
EP0184099B1 (fr) | 1991-01-02 |
DK551885D0 (da) | 1985-11-28 |
US4704212A (en) | 1987-11-03 |
EP0184099A3 (en) | 1988-05-25 |
DE3581068D1 (de) | 1991-02-07 |
DE3444068A1 (de) | 1986-06-05 |
ES549515A0 (es) | 1987-07-01 |
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