EP1075502B1 - Geschirrspülmittel mit antibakterieller wirkung - Google Patents
Geschirrspülmittel mit antibakterieller wirkung Download PDFInfo
- Publication number
- EP1075502B1 EP1075502B1 EP98924255A EP98924255A EP1075502B1 EP 1075502 B1 EP1075502 B1 EP 1075502B1 EP 98924255 A EP98924255 A EP 98924255A EP 98924255 A EP98924255 A EP 98924255A EP 1075502 B1 EP1075502 B1 EP 1075502B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- detergent
- alkyl
- quantities
- salts
- 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 - Lifetime
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- 239000003599 detergent Substances 0.000 title claims abstract description 37
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 23
- 238000004851 dishwashing Methods 0.000 title claims abstract description 22
- -1 alkylbenzene sulfonates Chemical class 0.000 claims abstract description 35
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 18
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- 239000004094 surface-active agent Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 229960003237 betaine Drugs 0.000 claims description 9
- 239000002736 nonionic surfactant Substances 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004615 ingredient Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 claims 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 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 239000002304 perfume Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 239000003755 preservative agent Substances 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000012963 UV stabilizer Substances 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims 5
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 2
- 235000010237 calcium benzoate Nutrition 0.000 claims 1
- 239000004301 calcium benzoate Substances 0.000 claims 1
- HZQXCUSDXIKLGS-UHFFFAOYSA-L calcium;dibenzoate;trihydrate Chemical compound O.O.O.[Ca+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HZQXCUSDXIKLGS-UHFFFAOYSA-L 0.000 claims 1
- GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 6
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 150000002191 fatty alcohols Chemical class 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000010348 incorporation Methods 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 230000003385 bacteriostatic effect Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 230000002147 killing effect Effects 0.000 description 3
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940091250 magnesium supplement Drugs 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229960003500 triclosan Drugs 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical class C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical class CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- LOJHHQNEBFCTQK-UHFFFAOYSA-N 2-phenoxypropan-1-ol Chemical compound OCC(C)OC1=CC=CC=C1 LOJHHQNEBFCTQK-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical class CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- ZZXDRXVIRVJQBT-UHFFFAOYSA-M Xylenesulfonate Chemical compound CC1=CC=CC(S([O-])(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Chemical class OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000003876 biosurfactant Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- 229940071118 cumenesulfonate Drugs 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000774 hypoallergenic effect Effects 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000020995 raw meat Nutrition 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229960001479 tosylchloramide sodium Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229940071104 xylenesulfonate Drugs 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
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial 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
- 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
- C11D3/34—Organic compounds containing sulfur
- C11D3/3409—Alkyl -, alkenyl -, cycloalkyl - or terpene sulfates or sulfonates
Definitions
- the invention relates to alkylbenzenesulfonate-containing dishwashing detergent, concentrated at Application show an antibacterial effect, i. with undiluted application one Inhibition of bacterial growth and, in addition, a number of Kill bacteria to a considerable extent.
- the object of the invention was now to formulate a hand dishwashing detergent, that too at 50% dilution still a significant inhibition of bacterial growth and also causes a high degree of germ killing.
- a modern hand dishwashing detergent must also have a special property spectrum have very good cleaning, skin compatibility, temperature and storage stability and ecological compatibility.
- Antibacterial rinsing agents are known in the art.
- a bacteriostatic component be u.a. Triclosan (2,4,4'-trichloro-2'-hydroxydiphenyl ether), natural or naturally identical extracts, e.g. Extracts of orange shark, pine oil, geraniol, nerol etc. used.
- a use of ecologically and economically acceptable triclosan amounts leads to a sufficient antibacterial effect at 100% use concentration, at Testing of antibacterial properties at a use concentration of 50% but no sufficient inhibitory effect on bacterial growth more.
- the bacteriostatic effect is not enough to even a sufficient inhibition of bacterial growth when using the hand dishwashing detergent using damp dish cloths, sponges or brushes.
- Chloramine-T toluenesulphonylchloramide-sodium salt
- Germall 115 imidazolidinyl urea
- sodium formate 2-phenoxyethanol, 1-phenoxy-2-propanol, 2-Phenoxy-1-propanol
- 2-Phenoxy-1-propanol showed in particular at 50% use concentration no adequate antibacterial effect.
- Dishwashing liquid containing benzoic acid or its salts are known from US-A-39 6317 and US-A-5 510 052.
- compositions proposed in the prior art is therefore suitable as arbitrarily perfumable, very good cleansing, hypoallergenic, temperature and storage-stable and ecologically compatible hand dishwashing detergent with specific antibacterial Efficacy for concentrated use on wet work surfaces, kitchen appliances using damp dishcloths, sponges and brushes.
- the present invention is therefore a hand dishwashing detergent with good antibacterial activity containing anionic surfactants, wherein the agent is an or several alkylbenzenesulfonates and as antibacterial active component benzoic acid and / or one or more of its salts in amounts of 1 to 8 wt .-%.
- benzoic acid and / or one or more of their salts as an antibacterial component in alkylbenzenesulfonate-containing Hand dishwashing detergents.
- Benzoic acid salts in the context of the present invention are in particular the sodium, potassium, Magnesium or calcium salts and mixtures thereof, alone or together can be used with benzoic acid in the inventive compositions.
- benzoic acid salts or benzoic acid optionally together with the corresponding hydroxides, i. Sodium, potassium, magnesium or calcium hydroxide used.
- the highest possible germ killing rate is a content of benzoic acid and / or its content Salts preferably from 9 to 6% by weight and more preferably from 1 to 4% wt.
- a benzoic acid and / or benzoic acid salt-containing rinse aid formulation at a pH in the finished product between 4 and 6, preferably between 4.5 and 5.5, in particular between 4.9 and 5.3, the strongest antibacterial activity paired with the most favorable storage stability having.
- the pH of the compositions according to the invention can be determined by means of customary pH regulators, For example, citric acid or sodium hydroxide can be adjusted.
- Alkylbenzenesulfonates in the context of the teaching according to the invention are alkylbenzenesulfonates with straight-chain or branched, saturated or unsaturated C 6-22- alkyl radicals, preferably C 8-18 -alkyl radicals, in particular C 9-14- alkyl radicals, most preferably C 10-13 -alkyl radicals.
- alkali metal and / or alkaline earth metal salts in particular sodium, potassium, magnesium and / or calcium salts, as well as ammonium salts or mono-, di- or triethanolammonium salts but also as alkylbenzenesulfonic acid together with the corresponding alkali metal or alkaline earth metal hydroxide and / or ammonia or mono-, di- or triethanolamine.
- alkylbenzenesulfonate-containing Due to the pronounced electrolyte sensitivity of alkylbenzenesulfonate-containing, In particular, alkylbenzenesulfonate sodium salt-containing agents, the incorporation of the for a sufficient antibacterial effect required amount of benzoic acid or Benzoic acid salts cause their expulsion or separation.
- benzoic acid or benzoic acid salts succeeds problem-free, if the alkylbenzenesulphonates are partially or completely converted in the form of their mono-, di- or trialkanolammonium salts, in particular triethanolammonium salts.
- the means include Alkylbenzenesulfonates excluding mono-, di- and / or trialkanolammonium alkylbenzenesulfonate, in particular triethanolammonium alkylbenzenesulfonate.
- benzoic acid or benzoates also succeeds when the means a Combination of alkylbenzenesulfonates with one or more fatty alcohol ether sulfates contain.
- alkylbenzenesulfonates exclusively mono-, di- or Trialkanolammoniumalkylbenzolsulfonate included on average.
- anionic surfactants according to the present invention may be other than the alkylbenzenesulfonates and the aforementioned fatty alcohol ether sulfates aliphatic sulfates such as fatty alcohol sulfates, dialkyl ether sulfates, monoglyceride sulfates and aliphatic sulfonates such as alkanesulfonates, olefin sulfonates, ether sulfonates, n-alkyl ether sulfonates, ester sulfonates, and Lingninsulfonate.
- fatty acid cyanamides also usable in the context of the present invention are fatty acid cyanamides, sulfosuccinic acid esters, fatty acid isethionates, acylaminoalkanesulfonates (Fatty acid taurides), fatty acid sarcosinates, ether carboxylic acids and alkyl (ether) phosphates.
- fatty alcohol ether sulfates Particularly preferred in the context of the present invention are the fatty alcohol ether sulfates. Also preferred are fatty alcohol sulfates and combinations of fatty alcohol ether sulfates and fatty alcohol sulfates.
- fatty acids or fatty alcohols or their derivatives - unless otherwise stated - representative of branched or unbranched carboxylic acids or alcohols or their derivatives having preferably 6 to 22 carbon atoms.
- the former are particularly preferred because of their vegetable base as based on renewable raw materials for environmental reasons, but without limiting the teaching of the invention to them.
- the oxo alcohols or their derivatives which are obtainable, for example, by the ROELEN 's oxo synthesis, can also be used correspondingly.
- Fatty alcohol ether sulfates are products of sulfation reactions on alkoxylated alcohols.
- the person skilled in the art generally understands the reaction products under alkoxylated alcohols of alkylene oxide, preferably ethylene oxide, with alcohols, preferably in the sense of the present invention Invention the longer chain alcohols. Usually arise from n moles Ethylene oxide and one mole of alcohol, depending on the reaction conditions a complex Mixture of addition products of different degrees of ethoxylation.
- a Another embodiment is preferred in the use of mixtures of the alkylene oxides the mixture of ethylene oxide and propylene oxide.
- Lower ethoxylated fatty alcohols (0.5 to 4 moles of EO) are preferred in the present invention 1 to 2.5 moles of EO).
- the anionic surfactants are preferably used in amounts of from 0.2 to 40% by weight, in particular from 3 to 35 wt .-%, particularly preferably from 5 to 30 wt .-%.
- Suitable surfactant mixtures are especially those of anionic in combination with one or more nonionic surfactants or betaine surfactants, the betaine surfactants in this context is to be equated with the class of amphoteric surfactants. Also the joint additional use of nonionic surfactants and betaine surfactants in Mixture may be advantageous for many applications.
- the surfactants are used in amounts of 0.2 to 50 wt .-%, preferably from 1 to 40 wt .-%, in particular of 3 to 35 wt .-% and most preferably from 5 to 30 wt .-%.
- Nonionic surfactants in the context of the present invention may be alkoxylates such as Polyglycol ethers, fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, end-capped Polyglycol ethers, mixed ethers and hydroxy mixed ethers and fatty acid polyglycol esters. Also useful are ethylene oxide, propylene oxide, block polymers and fatty acid alkanolamides and fatty acid polyglycol ethers.
- An important class of nonionic surfactants, which can be used in the invention are the polyol surfactants and especially here the glucosurfactants, such as alkylpolyglycoside and fatty acid glucamides. Especially preferred are the alkyl polyglucosides.
- Alkylpolyglycosides are surfactants which can be obtained by the reaction of sugars and alcohols according to the relevant processes of preparative organic chemistry, wherein, depending on the nature of the preparation, a mixture of monoalkylated, oligomeric or polymeric sugars is obtained.
- Preferred alkyl polyglycosides may be alkyl polyglucosides, the alcohol particularly preferably being a long-chain fatty alcohol or a mixture of long-chain fatty alcohols with branched or unbranched C 8 - to C 18 -alkyl chains and the degree of oligomerization (DP) of the sugars between 1 and 10, preferably 1 to 6, in particular 1.1 to 3, more preferably 1.1 to 1.7.
- compositions contain nonionic surfactants in amounts of from 0.1 to 14.9 wt .-%, in particular from 0.5 to 8 wt .-% and most preferably from 1 to 6% by weight.
- betaine surfactants which can be used according to the invention include the alkylbetaines, the alkylamidobetaines, the imidazolinium betaines and the aminopropionates as well such as the sulfobetaines and biosurfactants.
- a preferred ingredient here is alkylamidobetaine.
- these betaine surfactants in amounts of 0.05 to 10 wt .-%, in particular from 0.1 to 7 wt .-%, most preferably from 0.2 to 5 wt .-%, used.
- Advantages in terms of clarity of the products are also obtained - especially in mixtures containing high levels of surfactants - when the formulation contains one or more dicarboxylic acids and / or salts thereof, alone or in admixture, preferably a composition of sodium salts of adipic, succinic and glutaric acid, as it is available, for example, under the trade name Sokalan® DSC Na .
- solvents for example, alcohols, preferably low molecular weight alkanols having 1 to 4 carbon atoms in the molecule, especially ethanol and isopropanol. They contribute to the incorporation of perfume and dye, prevent the formation of liquid crystalline phases and improve the cold stability of the clear formulations.
- a solvent content of up to 8% by weight, preferably from 0.3 to 6% by weight, in particular from 0.5 to 5% by weight.
- solubilizers for example, alkanolamines, polyols such as Ethylene glycol, 1, 2-propylene glycol, glycerol and other monohydric and polyhydric alcohols and alkylbenzenesulfonates having 1 to 3 carbon atoms in the alkyl radical, in particular Cumene, toluene and xylene sulfonate, in amounts of up to 5 wt .-%, preferably 0.05 to 3 wt .-%, in particular 0.1 to 2 wt .-%, from.
- solubilizers for example, alkanolamines, polyols such as Ethylene glycol, 1, 2-propylene glycol, glycerol and other monohydric and polyhydric alcohols and alkylbenzenesulfonates having 1 to 3 carbon atoms in the alkyl radical, in particular Cumene, toluene and xylene sulfonate, in amounts of up
- ingredients e.g. UV stabilizers, defoamers (such as silicone oils, Paraffin oils or mineral oils), structuring agents, perfumes, dyes, corrosion inhibitors, Preservatives or the like, preferably in amounts of up to 5 wt .-%, included be.
- the hand dishwashing detergents according to the invention can be obtained by stirring together individual components in any order and leaving the mixture to stand until Create freedom from blisters.
- the order of attachment is not for the preparation of the agent crucial.
- compositions E1 to E5 according to the invention were prepared as described above and their pH, their viscosity, their clouding or clearing point and partly also their antibacterial activity and their rinsing power were determined.
- compositions of the compositions E1 to E5 according to the invention in% by weight and the specific properties are reproduced in Table 1.
- agents E1 to E5 according to the invention contained traces of dye.
- the pH of the agents E1 to E5 according to the invention was adjusted with citric acid.
- the viscosity was determined at 20 ° C. using a Brookfield LV DV II + viscometer (spindle 25, shear rate 30 min -1 ).
- the cold cloud point was determined by cooling a sample in the cryostat with a cooling rate of 0.2 ° C ⁇ min -1 , wherein as the cold cloud point is the temperature at which a slight turbidity was first detected. After the sample was completely clouded, heating was effected at a heating rate of 0.2 ° C.min -1 .
- the clear point is the temperature at which the sample was for the first time completely clear.
- the rinsing power of the agents E1 to E3 and E5 according to the invention was determined in a semi-automatic plate test apparatus using two different soils (beef tallow or olive oil / porcine grease stain). It was at a constant temperature of 40 or 45 ° C in 5 liters of water with 16 ° German hardness under constant conditions compared to a high-quality classical hand dishwashing detergent as a laboratory standard soiled with the test soil dish rinsed until the - formed before the start of foam - destroyed was and the plates were not clean anymore. The concentration of the agent was 4 ml per 5 liters of water. The number of rinsed plates is set in relation to the laboratory standard with a rinsing capacity of 100% (the average over both soils is indicated).
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
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- Detergent Compositions (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
| E1 | E2 | E3 | E4 | E5 | ||
| C10-13-ABS-Na-Salz | 9,4 | 9,1 | 8,5 | - | 8,5 | |
| C10-13-ABS-TEA-Salz | - | - | - | 9 | 9,5 | |
| C12/14-Alkoholethersulfat(2EO)-Na-Salz | 9,5 | 9 | 10,5 | 9 | 3,5 | |
| C12/16-Alkylpolyglucosid, DP = 1,4 | - | 4 | - | 4 | - | |
| Cocoamidopropylbetain | 0,3 | - | 0,3 | - | - | |
| Benzoesäure, techn. | 3 | 3 | - | - | 3 | |
| Na-Benzoat | - | - | 3,5 | 3,5 | - | |
| Ethanol | 0,9 | - | - | - | - | |
| Cumolsulfonat-Na-Salz | - | 1,5 | 0,2 | 0,9 | - | |
| Parfüm | 0,2 | 0,4 | 0,2 | 0,4 | 0,2 | |
| Wasser ad | 100 | 100 | 100 | 100 | 100 | |
| pH-Wert | 5,1 | 5,1 | 5,0 | 5,0 | 5,1 | |
| Viskosität bei 20 °C | [mPa·s] | 935 | 955 | 1175 | 1100 | 525 |
| Kältetrübungs-/Klarpunkt | [°C] | -3/+3 | -2/+5 | -3/+2 | +2/+5 | -3/+4 |
| Aussehen | klar | Klar | klar | Klar | Klar | |
| Spülvermögen | [%] | 97 | 102 | 93 | - | 102 |
| DGHM-Suspensionstest | > 5,08 | > 5,08 | - | - | - | |
| EN 1040 (best. = bestanden) | - | - | best. | best. | - |
Claims (18)
- Antibakterielles Handgeschirrspülmittel enthaltend anionische Tenside, dadurch gekennzeichnet, daß es ein oder mehrere Alkylbenzolsulfonate und als antibakterielle Wirkkomponente Benzoesäure und/oder eines oder mehrere ihrer Salze in Mengen von 1 bis 8 Gew.-% enthält.
- Mittel nach Anspruch 1, dadurch gekennzeichnet, daß es Mono-, Di- oder Trialkanolammonium-alkylbenzolsulfonat, insbesondere Triethanolammonium-alkylbenzolsulfonat, bevorzugt in Mengen von, bezogen auf die Gesamtgewichtsmenge an Alkylbenzolsulfonaten, von 10 bis 100 %, vorzugsweise von 30 bis 100 %, insbesondere von 50 bis 100 %, enthält.
- Mittel nach Anspruch 2, dadurch gekennzeichnet, daß es als Alkylbenzolsulfonate ausschließlich Mono-, Di- oder Trialkanolammonium-alkylbenzolsulfonat, insbesondere Triethanolammonium-alkylbenzolsulfonat enthält.
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es ein oder mehrere Fettalkoholethersulfate enthält.
- Mittel nach Anspruch 4, dadurch gekennzeichnet, daß es Alkylbenzolsulfonate und Fettalkoholethersulfate in einem Gewichtsmengenverhältnis von 10 : 1 bis 1 : 5, vorzugsweise von 5 : 1 bis 1 : 2, insbesondere von 2 : 1 bis 1 : 1,5, enthält.
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es einen pH-Wert zwischen 4,0 und 6,0, bevorzugt zwischen 4,5 und 5,5, besonders bevorzugt zwischen 4,9 und 5,3 aufweist.
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es anionische Tenside in Kombination mit einem oder mehreren nichtionischen Tensiden oder Betaintensiden enthält.
- Mittel nach Anspruch 7, dadurch gekennzeichnet, daß es nichtionische Tenside und Betaintenside enthält.
- Mittel nach Anspruch 7 oder 8, dadurch gekennzeichnet, daß es als eine nichtionische Tensidkomponente ein oder mehrere Alkylpolyglykoside, bevorzugt Alkylpolyglucoside, enthält.
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es Benzoesäure und/oder eines oder mehrere ihrer Salze in Mengen von 3 bis 8 Gew.-% enthält.
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es Natrium-, Kalium-, Magnesium- oder Calciumbenzoat oder deren Mischungen allein oder zusammen mit Benzoesäure enthält.
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es 0,2 bis 50 Gew.-%, bevorzugt 1 bis 40 Gew.-%, besonders bevorzugt 3 bis 35 Gew.-%, äußerst bevorzugt 5 bis 30 Gew.-% Tensidmischung enthält.
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß esenthält.(a) 0,2 bis 40 Gew.-%, vorzugsweise 1 bis 40 Gew.-%, besonders bevorzugt 3 bis 35 Gew.-%, anionische Tenside, insbesondere neben den Alkylbenzolsulfonaten Fettalkoholethersulfate,(b) 0,1 bis 14,9 Gew.-%, vorzugsweise 0,5 bis 8 Gew.-%, besonders bevorzugt 1 bis 6 Gew.-%, nichtionische Tenside, insbesondere Alkylpolyglucoside, und(c) 0,05 bis 10 Gew.-%, vorzugsweise 0,1 bis 7 Gew.-%, besonders bevorzugt 0,2 bis 5 Gew.-%, Betaintenside, insbesondere Alkylamidobetaine,
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es ein Lösungsmittel, vorzugsweise ein oder mehrere niedermolekulare Alkohole, insbesondere Ethanol, in Mengen von bis zu 8 Gew.-%, bevorzugt von 0,3 bis 6 Gew.-%, insbesondere von 0,5 bis 5 Gew.-%, enthält.
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es ein oder mehrere Lösungsvermittler aus der Gruppe der Alkanolamine, Polyole, insbesondere Ethylenglykol, 1,2-Propylenglykol, Glycerin, sowie Alkylbenzolsulfonate mit 1 bis 3 Kohlenstoffatomen im Alkylrest, insbesondere Cumol-, Toluol- und Xylolsulfonate, in Mengen von bis zu 5 Gew.-%, vorzugsweise 0,05 bis 3 Gew.-%, insbesondere 0,1 bis 2 Gew.-%, enthält.
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es als weiteren Inhaltsstoff eine oder mehrere Dicarbonsäuren und/oder deren Salze, allein oder in Mischung, in Mengen von 0,1 bis 8 Gew.-%, bevorzugt in Mengen zwischen 1 und 6 Gew.-%, insbesondere zwischen 2,5 und 5 Gew.-%, enthält.
- Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, daß es weiter in Handgeschirrspülmitteln übliche Inhaltstoffe, wie UV-Stabilisatoren, Entschäumer, Lösungsvermittler, Strukturierungsmittel, Parfumstoffe, Farbstoffe, Korrosionsinhibitoren oder Konservierungsmittel, enthält.
- Verwendung von Benzoesäure und/oder einem oder mehrerer ihrer Salze in Mengen von 1 bis 8 Gew.-% als antibakterielle Komponente in Alkylbenzolsulfonat-haltigen Handgeschirrspülmitteln.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP1998/002565 WO1999057235A1 (de) | 1998-04-30 | 1998-04-30 | Geschirrspülmittel mit antibakterieller wirkung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1075502A1 EP1075502A1 (de) | 2001-02-14 |
| EP1075502B1 true EP1075502B1 (de) | 2005-10-12 |
Family
ID=8166947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP98924255A Expired - Lifetime EP1075502B1 (de) | 1998-04-30 | 1998-04-30 | Geschirrspülmittel mit antibakterieller wirkung |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1075502B1 (de) |
| CN (1) | CN1291225A (de) |
| AT (1) | ATE306533T1 (de) |
| DE (1) | DE59813107D1 (de) |
| ES (1) | ES2249831T3 (de) |
| HU (1) | HUP0103189A2 (de) |
| SK (1) | SK16202000A3 (de) |
| TR (1) | TR200002723T2 (de) |
| WO (1) | WO1999057235A1 (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10023438A1 (de) * | 2000-05-12 | 2001-11-22 | Henkel Kgaa | Konzentrat zur Verdünnung unter Viskositätserhalt oder -erhöhung |
| DE10122380A1 (de) * | 2001-05-09 | 2002-11-28 | Schuelke & Mayr Gmbh | Alkoholfreies Flüssig-Konzentrat zur Konservierung von kosmetischen, Haushalts- und technischen Produkten |
| GB0112567D0 (en) * | 2001-05-24 | 2001-07-18 | Cussons Int Ltd | Bactericidal liquid detergent composition |
| EP1331261A1 (de) * | 2002-01-23 | 2003-07-30 | Chemische Fabrik Dr. Weigert GmbH & Co. KG. | Verfahren zum Reinigen und Desinfizieren von Geschirr |
| DE102009005791A1 (de) | 2009-01-22 | 2010-07-29 | Henkel Ag & Co. Kgaa | Handgeschirrspülmittel mit antibakterieller Wirkung |
| CN104194970A (zh) * | 2014-09-29 | 2014-12-10 | 镇江华域环保设备制造有限公司 | 一种餐具专用洗洁精 |
| CN105524731A (zh) * | 2014-09-30 | 2016-04-27 | 青岛康和食品有限公司 | 一种含有抗过敏成分的洗洁精 |
| CN106318678A (zh) * | 2016-07-25 | 2017-01-11 | 广州普爱生物科技有限公司 | 无水无防腐剂无酒精的蛋白酶超浓缩洗衣液 |
| CN117821177B (zh) * | 2023-12-29 | 2025-10-24 | 广东优凯科技有限公司 | 一种高效抑菌的餐具洗涤剂组合物及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2226988A1 (de) * | 1972-06-02 | 1973-12-20 | Henkel & Cie Gmbh | Geschirrspuel- und reinigungsmittel |
| US4867898A (en) * | 1987-03-23 | 1989-09-19 | American Cyanamid Company | Broad spectrum antimicrobial system for hard surface cleaners |
| NZ240355A (en) * | 1991-06-04 | 1994-09-27 | Ecolab Inc | Sanitising composition comprising sorbic and benzoic acids |
| DE4417809A1 (de) * | 1994-05-20 | 1995-11-23 | Becker Klaus | Verfahren zur Sanitärreinigung sowie ein Sanitärreiniger |
| US5510052A (en) * | 1994-08-25 | 1996-04-23 | Colgate-Palmolive Co. | Enzymatic aqueous pretreatment composition for dishware |
-
1998
- 1998-04-30 ES ES98924255T patent/ES2249831T3/es not_active Expired - Lifetime
- 1998-04-30 EP EP98924255A patent/EP1075502B1/de not_active Expired - Lifetime
- 1998-04-30 DE DE59813107T patent/DE59813107D1/de not_active Expired - Lifetime
- 1998-04-30 TR TR2000/02723T patent/TR200002723T2/xx unknown
- 1998-04-30 HU HU0103189A patent/HUP0103189A2/hu unknown
- 1998-04-30 SK SK1620-2000A patent/SK16202000A3/sk unknown
- 1998-04-30 WO PCT/EP1998/002565 patent/WO1999057235A1/de not_active Ceased
- 1998-04-30 CN CN98813991.XA patent/CN1291225A/zh active Pending
- 1998-04-30 AT AT98924255T patent/ATE306533T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE59813107D1 (de) | 2006-02-23 |
| TR200002723T2 (tr) | 2000-12-21 |
| HUP0103189A2 (hu) | 2002-01-28 |
| EP1075502A1 (de) | 2001-02-14 |
| ATE306533T1 (de) | 2005-10-15 |
| WO1999057235A1 (de) | 1999-11-11 |
| ES2249831T3 (es) | 2006-04-01 |
| SK16202000A3 (sk) | 2001-04-09 |
| CN1291225A (zh) | 2001-04-11 |
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