EP0340704A2 - Compositions détergentes aqueuses acides - Google Patents
Compositions détergentes aqueuses acides Download PDFInfo
- Publication number
- EP0340704A2 EP0340704A2 EP89107879A EP89107879A EP0340704A2 EP 0340704 A2 EP0340704 A2 EP 0340704A2 EP 89107879 A EP89107879 A EP 89107879A EP 89107879 A EP89107879 A EP 89107879A EP 0340704 A2 EP0340704 A2 EP 0340704A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- bis
- weight
- fatty
- atoms
- reacting
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- OBMBUODDCOAJQP-UHFFFAOYSA-N 2-chloro-4-phenylquinoline Chemical compound C=12C=CC=CC2=NC(Cl)=CC=1C1=CC=CC=C1 OBMBUODDCOAJQP-UHFFFAOYSA-N 0.000 title 1
- 239000011260 aqueous acid Substances 0.000 title 1
- 238000009472 formulation Methods 0.000 claims abstract description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- 229920005862 polyol Polymers 0.000 claims abstract description 25
- 230000002378 acidificating effect Effects 0.000 claims abstract description 24
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 20
- 150000003077 polyols Chemical class 0.000 claims abstract description 19
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 18
- -1 alkenyl glycidyl ethers Chemical class 0.000 claims abstract description 18
- 229920000570 polyether Polymers 0.000 claims abstract description 18
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 14
- 239000000194 fatty acid Substances 0.000 claims abstract description 14
- 229930195729 fatty acid Natural products 0.000 claims abstract description 14
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 14
- 150000001298 alcohols Chemical class 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 15
- 238000004140 cleaning Methods 0.000 claims description 13
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 description 20
- 239000002562 thickening agent Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 2
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 235000013365 dairy product Nutrition 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- MCWZNJNWGQPUGL-UHFFFAOYSA-N 1-methyl-1-phenylthiourea Chemical compound NC(=S)N(C)C1=CC=CC=C1 MCWZNJNWGQPUGL-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- GTTITHACWAWITC-UHFFFAOYSA-N 2-(2-octyldodecoxymethyl)oxirane Chemical compound CCCCCCCCCCC(CCCCCCCC)COCC1CO1 GTTITHACWAWITC-UHFFFAOYSA-N 0.000 description 1
- DDHJMUWKDMGQFH-KTKRTIGZSA-N 2-[[(z)-octadec-9-enoxy]methyl]oxirane Chemical group CCCCCCCC\C=C/CCCCCCCCOCC1CO1 DDHJMUWKDMGQFH-KTKRTIGZSA-N 0.000 description 1
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 1
- MBJVZMPEPVSKAS-UHFFFAOYSA-N 2-hexacosyloxirane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC1CO1 MBJVZMPEPVSKAS-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CVLHGLWXLDOELD-UHFFFAOYSA-N 4-(Propan-2-yl)benzenesulfonic acid Chemical compound CC(C)C1=CC=C(S(O)(=O)=O)C=C1 CVLHGLWXLDOELD-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- 241001012508 Carpiodes cyprinus Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000001204 arachidyl 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])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- NYTBHLJJQXOHJR-UHFFFAOYSA-N hept-3-ene-1,2,6,7-tetrol Chemical compound OCC(O)CC=CC(O)CO NYTBHLJJQXOHJR-UHFFFAOYSA-N 0.000 description 1
- TUYVVZNULFVBEZ-UHFFFAOYSA-N hex-4-ene-1,3,6-triol Chemical compound OCCC(O)C=CCO TUYVVZNULFVBEZ-UHFFFAOYSA-N 0.000 description 1
- ZJUFPQDVIGUBQX-UHFFFAOYSA-N hex-4-yne-1,3,6-triol Chemical compound OCCC(O)C#CCO ZJUFPQDVIGUBQX-UHFFFAOYSA-N 0.000 description 1
- KUQWZSZYIQGTHT-UHFFFAOYSA-N hexa-1,5-diene-3,4-diol Chemical compound C=CC(O)C(O)C=C KUQWZSZYIQGTHT-UHFFFAOYSA-N 0.000 description 1
- TZQPAZWGRJYTLN-UHFFFAOYSA-N hexane-2,3,4,5-tetrol Chemical compound CC(O)C(O)C(O)C(C)O TZQPAZWGRJYTLN-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001421 myristyl 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])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NXBZOSIUSIHMDY-UHFFFAOYSA-N oct-4-yne-1,2,7,8-tetrol Chemical compound OCC(O)CC#CCC(O)CO NXBZOSIUSIHMDY-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000000913 palmityl 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])([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
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 125000004079 stearyl 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])([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])C([H])([H])[H] 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- C11D3/02—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
- 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
-
- 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
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
-
- 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
- C11D3/3707—Polyethers, e.g. polyalkyleneoxides
Definitions
- Aqueous acidic cleaner formulations are known. They contain tensides and acids as essential components.
- the known acidic technical cleaners are used, for example, in dairies to remove deposits of lactic acid. They are also used to clean pipelines in which deposits of calcium and magnesium carbonates have formed.
- the cleaning agent formulations In order to extend the exposure time of these technical cleaning systems when cleaning hard surfaces and thus to ensure optimal cleaning performance, the cleaning agent formulations must have a minimum viscosity so that the formulation cannot run off too quickly from the surface to be cleaned.
- the viscosity of the known cleaner formulations is adjusted by using mixtures of different alkylphenol ethoxylates with different degrees of ethoxylation.
- nonionic surfactants based on alkoxylated fatty alcohols, fatty acids, fatty amines, fatty acid amides or alkanesulfonamides are now used. However, the viscosity of such aqueous acidic cleaning formulations is not yet sufficient.
- the present invention has for its object to provide aqueous acidic cleaner formulations which have an increased viscosity compared to the known acidic technical cleaners.
- the cleaner formulations should also be stable in storage.
- the detergent formulations can optionally contain further, conventional constituents, such as solubilizers, corrosion inhibitors and builders.
- the aqueous acidic cleaning formulations contain, as an essential component (a), at least one nonionic surfactant based on alkoxylated fatty alcohols, fatty acids, fatty amines, fatty acid amides or alkanesulfonamides. These compounds are addition products of 3 to 40 moles of ethylene oxide with 1 mole of fatty alcohols, fatty acids, fatty amines, fatty acid amides or alkanesulfonamides each containing at least 8 carbon atoms.
- the adducts of 3 to 20 moles of ethylene oxide with 1 mole of at least one alcohol having 10 to 18 carbon atoms are particularly preferred for use in the preparation of the aqueous acidic cleaner formulations.
- Suitable alcohols are preferably coconut oil or tallow fatty alcohols, oleyl alcohol or synthetically produced alcohols with 8 to 18 carbon atoms.
- the synthetic alcohols are produced, for example, by the Oxo process or the Ziegler process.
- Preferred alcohols are, for example, isodecanol, decanol, isotridekanol and mixtures of C13 / C15 fatty alcohol mixtures and C16 / C16 fatty alcohol mixtures.
- the ethoxylated fatty alcohols used with particular preference contain 3 to 16 moles of ethylene oxide per mole of alcohol.
- the amount of nonionic surfactants in the aqueous acidic cleaning formulations is 1 to 20, preferably 5 to 15% by weight.
- the aqueous acidic cleaning formulations contain, as a further essential component, at least one polyether polyol which can be obtained by reacting 2 to 6-valent alcohols which have 2 to 10 C atoms with alkylene oxides containing 2 to 4 C atoms and reacting these reaction products with 8 up to 30 carbon atoms containing 1,2-alkylene oxides, alkyl or alkenyl glycidyl ethers.
- polyether polyols of component (b) are prepared in an at least two-stage process.
- ethylene oxide or first ethylene oxide and then an alkylene oxide with 3 or 4 carbon atoms are added to a polyfunctional alcohol with 2 to 10 carbon atoms and 2 to 6 hydroxyl groups.
- at least 1 alkylene oxide having 8 to 30 carbon atoms or an alkyl or alkenyl glycidyl ether having 8 to 30 carbon atoms in the alkyl or alkylene radical is added to the reaction product thus obtained. If mixtures of alkylene oxides with 2 to 4 carbon atoms are used in the first reaction stage, either statistical copolymers can be used (ie the reaction is carried out with mixtures of alkylene oxides carried out) or block copolymers.
- the block copolymers are formed by first reacting the compounds to be alkoxylated, for example, with ethylene oxide and then with propylene oxide or a butylene oxide.
- the alkylene oxides are added in a known manner to 2- to 6-valent alcohols.
- These polyfunctional alcohols can be alkane polyols, alkene polyols, alkyne polyols or oxialkylene polyols.
- alkane polyols are ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, trimethylolpropane, pentaerythritol, glycerol, 2,3,4,5- Hexantetrol, glucose and similarly structured sugars.
- alkene polyols are 2-butene-1,4-diol, 2-hexene-1,4,6-triol, 1,5-hexadiene-3,4-diol, 3-heptene-1,2,6,7- tetrol.
- alkyne polyols examples include 2-butyne-1,4-diol, 2-hexyne-1,4,6-triol and 4-octyne-1,2,7,8-tetrol.
- oxyalkylene glycols are said to include diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol and the like. Connections are understood.
- trimethylolpropane, pentaerythritol, ethylene glycol and diethylene glycol are preferably suitable for the preparation of the polyether polyols according to (b).
- At least one sufficient amount of an alkylene oxide with 2 to 4 carbon atoms is added to 1 mol of the polyhydric alcohol to produce products which contain up to 90% by weight of oxyalkylene units of alkylene oxides containing 2 to 4 carbon atoms.
- the alkylene oxide addition product produced in the first stage of the reaction can also consist entirely of oxyethylene units.
- those reaction products of the polyhydric alcohols with ethylene oxide and propylene oxide which contain ethylene oxide and propylene oxide in a weight ratio of 70:30 to 95: 5 added to a polyhydric alcohol are of interest. This can be either statistical polymers or block copolymers.
- the polyhydric alcohols prepared in the first process stage and reacted with C2- to C4-alkylene oxides are reacted with 1,2-alkylene oxides containing 8 to 30 C atoms.
- 1,2-alkylene oxides 1,2-alkyl or 1,2-alkenyl glycidyl ether can also be used.
- the preparation of such glycidyl ethers is known, for example, from US Pat. No. 4,086,279.
- Suitable long-chain alkylene oxides are, for example, 1,2-epoxyoctane, 1,2-epoxydodecane, 1,2-epoxyhexadecane, 1,2-epoxyoctacosane as well as mixtures of the epoxides mentioned and the commercially available mixtures of epoxides which have 10 to 20 carbon atoms.
- alkyl glycidyl ethers examples include dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, 2-methyldodecyl and 2-methyl tetradecyl, 2-methylpentadecyl, 2-hexyldecyl or 2-octyldodecylglycidyl ether.
- Alkenyl glycidyl ether is preferably oleyl glycidyl ether.
- the alkoxylations in the first and second reaction stages for the preparation of the polyether polyols are preferably carried out in the presence of bases such as sodium hydroxide solution or potassium hydroxide solution, at higher temperatures, e.g. up to temperatures of 160 ° C.
- the reaction products obtained in the second stage contain the long-chain 1,2-alkylene oxide or the long-chain glycidyl ether in an amount of 0.5 to 75, preferably 1 to 20% by weight in the attached form.
- Amounts of 1,2-alkylene oxides having 8 to 30 carbon atoms or the corresponding glycidyl ethers in the polyether polyol are particularly preferred such that the average molar ratio of longer-chain epoxide or glycidyl ether to each individual hydroxyl group of the polyhydric alcohol is preferably between 0.5 and 5 0.5 to 1.5.
- the molecular weight of the polyether polyols of component (b) of the detergent formulations is 1000 to 75,000 and is preferably in the range from 5000 to 25,000.
- the polyether polyols described are used in amounts of 0.1 to 15, preferably 0.15 to 10,% by weight in aqueous acidic cleaner formulations. In such formulations, together with the nonionic surfactants specified under (a), they produce a synergistic effect with regard to the increase in viscosity.
- the viscosities of the aqueous acidic cleaning formulations are 100 to 19000 mPa.s.
- inorganic or organic acids are suitable, e.g. Hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, oxalic acid and citric acid or dicarboxylic acid mixtures (e.g. from succinic acid, glutaric acid and adipic acid). Acidic phosphoric acid esters as well as amidosulfonic acid and propanesulfonic acid are also suitable.
- the cleaning formulations contain 1 to 40, preferably 5 to 20% by weight of at least one acid.
- the acidic cleaning formulations contain water to make up to 100% by weight.
- the cleaner formulations may also contain other constituents, such as solubilizers, corrosion inhibitors or builders.
- Solubilizers are, for example, compounds such as isopropanol, glycol ether, cumene sulfonic acid or their alkali salts.
- the solubilizers are used in an amount of up to 10% by weight, based on the overall formulation.
- the cleaner formulations can also contain corrosion inhibitors, which may be used in amounts of up to 1% by weight. Suitable corrosion inhibitors are, for example, for HCl / H2SO4, 1,4-butynediol with application amounts of 0.1 to 0.2% for 10% effectively present acid or for H3PO4 methylphenylthiourea with 0.5%, based on 20% effectively present acid.
- the cleaner formulations may also contain builders if necessary. These are, for example, compounds such as acidic salts of phosphoric acid, sulfuric acid etc. (sodium hydrophosphate, sodium bisulfate).
- the amount of builders in the detergent formulation is up to 20% by weight.
- aqueous acidic cleaner formulations described above are used to clean hard surfaces.
- the removal of calcium and magnesium carbonate deposits from pipelines or heat exchangers which are operated with hard water may be mentioned as an example.
- the acidic cleaner formulations are also used in dairies, for example to remove lactic acid deposits from objects made of metal, porcelain or ceramics.
- the parts given in the following examples are parts by weight, the data in% relate to the weight of the substances.
- the viscosities were measured in a Couette rotary viscometer at 20 ° C and a shear of 150 seconds ⁇ 1.
- the molecular weights of the substances are average molecular weights after the number average.
- polyether polyols were used as thickeners (component (b)):
- Polyether polyol with a molecular weight of approx. 17,000 which can be obtained by reacting 1 mol of trimethylolpropane with a mixture of 102 mol of ethylene oxide and 19 mol of propylene oxide and then further reacting the alkoxylation product with 3 mol of a 1,2-alkylene oxide with 16 carbon atoms.
- the proportion of long-chain alkylene oxide was 4.06% by weight.
- the proportion of longer-chain bound alkylene oxide was 4.18% by weight.
- the built-in C18 alkylene oxide content was 4.55% by weight.
- surfactant I Addition product of 7 moles of ethylene oxide with 1 mole of isodecanol.
- Surfactant II Addition product of 8 moles of ethylene oxide with 1 mole of isotridecanol.
- Surfactant III Addition product of 7 moles of ethylene oxide with 1 mole of a C13 / C15 fatty alcohol mixture.
- Surfactant IV Addition product of 3 moles of ethylene oxide with 1 mole of a C13 / C15 fatty alcohol mixture.
- surfactant V Addition product of 5 moles of ethylene oxide with 1 mole of a C13 / C15 fatty alcohol mixture.
- Surfactant VI Addition product of 11 moles of ethylene oxide with 1 mole of a C13 / C15 fatty alcohol mixture.
- Surfactant VII Addition product of 11 moles of ethylene oxide with 1 mole of a C16 / C18 fatty alcohol mixture.
- Surfactant VIII Addition product of 5 moles of ethylene oxide with 1 mole of isotridecanol.
- Surfactant IX Addition product of 10 moles of ethylene oxide with 1 mole of C9-alkylphenol.
- Surfactant X Addition product of 8 moles of ethylene oxide with 1 mole of a C13- / C15 fatty alcohol.
- aqueous acidic cleaner formulations were prepared by mixing the surfactant, thickener, acid and water: 10% surfactant X% thickener 20% acid 70-X% water.
- a thickener-free formulation of the following composition was examined as a comparison: 15% surfactant 20% acid and 65% water.
- composition of the aqueous acidic cleaner formulations produced in each case and the viscosity of these formulations is given in Table 1.
- aqueous acidic cleaner formulations are obtained according to the invention which have greatly increased viscosities compared to the corresponding thickener-free cleaner formulations.
- Aqueous acidic cleaner formulations were prepared in accordance with the standard formulation given in Example 1. The table also provides information about the viscosity of the detergent formulations.
- Table 2 No. Surfactant (a) Concentration of surfactant [%] Thickener (b) Concentration of thickener [%] Acid 20% (c) Viscosity of the detergent formulation [mPa.s] 1 (compare) IX 10th - - H3PO4 18th 2 (compare) IX 10th A 1 " 40 3 (compare) III 10th - - " 90 4th III 10th A 1 " 2598 5 (compare) X 10th - - " 15 6 X 10th A 1 " 1082 7 VII 10th - - " 12 8th VII 10th A 1 " 865
- compositions given in Table 2 under Nos. 4, 6 and 8 are examples according to the invention, the other compositions are used for comparison.
- Table 2 the selection of the surfactant plays a decisive role for the desired high viscosity of a detergent formulation.
- An ethoxylated alkylphenol as a surfactant does not give the desired increase in viscosity, while the surfactants III, X and VII on the other hand lead to a surprisingly increased viscosity of the detergent formulation.
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- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT89107879T ATE98293T1 (de) | 1988-05-05 | 1989-04-29 | Waessrige saure reinigerformulierungen. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3815291 | 1988-05-05 | ||
| DE3815291A DE3815291A1 (de) | 1988-05-05 | 1988-05-05 | Waessrige saure reinigerformulierungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0340704A2 true EP0340704A2 (fr) | 1989-11-08 |
| EP0340704A3 EP0340704A3 (en) | 1990-05-02 |
| EP0340704B1 EP0340704B1 (fr) | 1993-12-08 |
Family
ID=6353685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89107879A Expired - Lifetime EP0340704B1 (fr) | 1988-05-05 | 1989-04-29 | Compositions détergentes aqueuses acides |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4965009A (fr) |
| EP (1) | EP0340704B1 (fr) |
| AT (1) | ATE98293T1 (fr) |
| DE (2) | DE3815291A1 (fr) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0523681A3 (en) * | 1991-07-17 | 1993-05-05 | Johannes Dr. Behrensdorf | Automatic dishwashing detergent composition and method for producing the same |
| EP0598692A1 (fr) * | 1992-11-16 | 1994-05-25 | The Procter & Gamble Company | Compositions de nettoyage pseudoplastiques et thixotropiques |
| EP0616028A1 (fr) * | 1993-03-19 | 1994-09-21 | The Procter & Gamble Company | Compositions de nettoyage comprenant des agents tensioactifs non-ioniques à chaînes courtes |
| TR26294A (tr) * | 1991-11-20 | 1995-03-15 | Alsthom Gec | ORTA GERILIMLI OTOMATIK KESICI SALTER VE BIR HüCRE ILE ORTA GERILIMLI AYGITLARDA KULLANIMI. |
| WO1998003243A1 (fr) * | 1996-07-19 | 1998-01-29 | Henkel Kommanditgesellschaft Auf Aktien | Utilisation comme agents antimousse de composes d'addition oxyde d'ethylene/oxyde de propylene de glycerine ou de polyglycerine mis a reagir avec des alpha-epoxydes d'olefine |
| EP0875554A1 (fr) * | 1997-04-30 | 1998-11-04 | The Procter & Gamble Company | Compositions acides pour enlever le tartre |
| EP0894849A1 (fr) * | 1997-07-29 | 1999-02-03 | Basf Corporation | Composition détergente à base de l'eau sans solvant contenant deux dérivés tensioactifs nonioniques |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4028138A1 (de) * | 1990-09-05 | 1992-03-12 | Huels Chemische Werke Ag | Viskose saeurehaltige reinigungsmittel |
| WO1993014181A1 (fr) * | 1992-01-06 | 1993-07-22 | Olin Corporation | Composition nettoyante, aqueuse et biodegradable pour filtres contenant un agent tensioactif ethoxyle/propoxyle, de l'acide carboxylique et un solvant |
| US5279707A (en) * | 1992-10-23 | 1994-01-18 | Time Savers | Die discoloration remover solution and method |
| US5851979A (en) * | 1992-11-16 | 1998-12-22 | The Procter & Gamble Company | Pseudoplastic and thixotropic cleaning compositions with specifically defined viscosity profile |
| US5981455A (en) * | 1993-03-19 | 1999-11-09 | The Procter & Gamble Company | Cleaning compositions with short chain nonionic surfactants |
| US5384063A (en) * | 1993-03-19 | 1995-01-24 | The Procter & Gamble Company | Acidic liquid detergent compositions for bathrooms |
| JP2947695B2 (ja) * | 1993-07-30 | 1999-09-13 | 日本ペイント株式会社 | アルミニウム系金属の酸性洗浄水溶液及びその洗浄方法 |
| US5736174A (en) * | 1994-03-14 | 1998-04-07 | Arco Chemical Technology, L.P. | Alkoxylated alcohol fat substitutes |
| US5801133A (en) * | 1995-05-08 | 1998-09-01 | Buckman Laboratories International Inc. | Effective alternative filter cleaner for biguanide treated recreational water systems |
| DE19525604C2 (de) * | 1995-07-16 | 1998-09-03 | Yankee Polish Lueth Gmbh & Co | Flüssiger Reiniger und dessen Verwendung |
| DE29511365U1 (de) * | 1995-07-16 | 1995-11-23 | Yankee Polish Lüth GmbH + Co, 21465 Reinbek | Flüssiger Reiniger |
| DE19545808C2 (de) * | 1995-12-08 | 1999-03-11 | Harald Baumgaertner | Verfahren zur Vorbehandlung von einer mit einer Silikonbeschichtung zu versehenden Glasscheibe |
| US5776876A (en) * | 1996-07-18 | 1998-07-07 | Bio-Lab, Inc. | Aqueous acidic filter cleaning composition for removing organic biguanide deposits |
| US5880078A (en) * | 1997-09-04 | 1999-03-09 | The United States Of America As Represented By The Secretary Of The Navy | Non-solvent, general use exterior aircraft cleaner |
| DE60124906T2 (de) | 2000-06-05 | 2007-05-24 | S.C. Johnson & Son, Inc., Racine | Biozide reinigungsmittel |
| DE102005034752A1 (de) * | 2005-07-21 | 2007-01-25 | Henkel Kgaa | Reinigungs- und Pflegemittel mit verbesserter Emulgierfähigkeit |
| US7741265B2 (en) * | 2007-08-14 | 2010-06-22 | S.C. Johnson & Son, Inc. | Hard surface cleaner with extended residual cleaning benefit |
| US8993502B2 (en) | 2008-02-21 | 2015-03-31 | S. C. Johnson & Son, Inc. | Cleaning composition having high self-adhesion to a vertical hard surface and providing residual benefits |
| US8980813B2 (en) | 2008-02-21 | 2015-03-17 | S. C. Johnson & Son, Inc. | Cleaning composition having high self-adhesion on a vertical hard surface and providing residual benefits |
| US9481854B2 (en) | 2008-02-21 | 2016-11-01 | S. C. Johnson & Son, Inc. | Cleaning composition that provides residual benefits |
| US8143206B2 (en) | 2008-02-21 | 2012-03-27 | S.C. Johnson & Son, Inc. | Cleaning composition having high self-adhesion and providing residual benefits |
| US9410111B2 (en) | 2008-02-21 | 2016-08-09 | S.C. Johnson & Son, Inc. | Cleaning composition that provides residual benefits |
| BRPI0908179A2 (pt) | 2008-02-21 | 2015-11-24 | Johnson & Son Inc S C | composição de limpeza possuindo alta auto-adesão e provendo benefícios residuais |
| US9404069B1 (en) | 2015-06-12 | 2016-08-02 | Crossford International, Llc | Systems and methods for cooling tower fill cleaning with a chemical gel |
| US10030216B2 (en) | 2015-06-12 | 2018-07-24 | Crossford International, Llc | Systems and methods for cooling tower fill cleaning with a chemical gel |
| US11421191B1 (en) | 2018-11-15 | 2022-08-23 | Ecolab Usa Inc. | Acidic cleaner |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3427248A (en) * | 1965-10-22 | 1969-02-11 | Lever Brothers Ltd | Detergent |
| DE2224992A1 (de) * | 1972-05-23 | 1973-12-06 | Henkel & Cie Gmbh | Klarspuelmittel fuer das maschinelle spuelen von geschirr |
| FR2407979A1 (fr) * | 1977-11-04 | 1979-06-01 | Basf Wyandotte Corp | Derives de polyglycerols a proprietes tensio-actives et procede pour leur preparation |
| US4709099A (en) * | 1979-10-22 | 1987-11-24 | Basf Corporation | Polyethers modified with alpha olefin oxides |
| US4665239A (en) * | 1979-10-22 | 1987-05-12 | Basf Corporation | Polyethers modified with alpha olefin oxides |
| US4649224A (en) * | 1979-10-22 | 1987-03-10 | Basf Corporation | Polyethers modified with alpha olefin oxides |
| US4587030A (en) * | 1983-07-05 | 1986-05-06 | Economics Laboratory, Inc. | Foamable, acidic cleaning compositions |
| US4759867A (en) * | 1983-07-07 | 1988-07-26 | The Clorox Company | Hard surface acid cleaner |
| US4501680A (en) * | 1983-11-09 | 1985-02-26 | Colgate-Palmolive Company | Acidic liquid detergent composition for cleaning ceramic tiles without eroding grout |
| GB8511305D0 (en) * | 1985-05-03 | 1985-06-12 | Procter & Gamble | Liquid detergent compositions |
| DE3607193A1 (de) * | 1986-03-05 | 1987-10-01 | Henkel Kgaa | Fluessige tensidmischungen |
| JP2710052B2 (ja) * | 1988-06-23 | 1998-02-10 | 東和化成工業株式会社 | コードファクター関連化合物及びその製造法並びに該化合物を含有する免疫増強剤 |
-
1988
- 1988-05-05 DE DE3815291A patent/DE3815291A1/de not_active Withdrawn
-
1989
- 1989-04-27 US US07/343,664 patent/US4965009A/en not_active Expired - Fee Related
- 1989-04-29 AT AT89107879T patent/ATE98293T1/de active
- 1989-04-29 DE DE89107879T patent/DE58906336D1/de not_active Expired - Lifetime
- 1989-04-29 EP EP89107879A patent/EP0340704B1/fr not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0523681A3 (en) * | 1991-07-17 | 1993-05-05 | Johannes Dr. Behrensdorf | Automatic dishwashing detergent composition and method for producing the same |
| TR26294A (tr) * | 1991-11-20 | 1995-03-15 | Alsthom Gec | ORTA GERILIMLI OTOMATIK KESICI SALTER VE BIR HüCRE ILE ORTA GERILIMLI AYGITLARDA KULLANIMI. |
| EP0598692A1 (fr) * | 1992-11-16 | 1994-05-25 | The Procter & Gamble Company | Compositions de nettoyage pseudoplastiques et thixotropiques |
| EP0616028A1 (fr) * | 1993-03-19 | 1994-09-21 | The Procter & Gamble Company | Compositions de nettoyage comprenant des agents tensioactifs non-ioniques à chaînes courtes |
| WO1998003243A1 (fr) * | 1996-07-19 | 1998-01-29 | Henkel Kommanditgesellschaft Auf Aktien | Utilisation comme agents antimousse de composes d'addition oxyde d'ethylene/oxyde de propylene de glycerine ou de polyglycerine mis a reagir avec des alpha-epoxydes d'olefine |
| EP0875554A1 (fr) * | 1997-04-30 | 1998-11-04 | The Procter & Gamble Company | Compositions acides pour enlever le tartre |
| EP0894849A1 (fr) * | 1997-07-29 | 1999-02-03 | Basf Corporation | Composition détergente à base de l'eau sans solvant contenant deux dérivés tensioactifs nonioniques |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0340704B1 (fr) | 1993-12-08 |
| EP0340704A3 (en) | 1990-05-02 |
| DE3815291A1 (de) | 1989-11-23 |
| US4965009A (en) | 1990-10-23 |
| ATE98293T1 (de) | 1993-12-15 |
| DE58906336D1 (de) | 1994-01-20 |
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