EP0783560B1 - Desinfizierende reinigungsmittel für harte oberflächen - Google Patents

Desinfizierende reinigungsmittel für harte oberflächen Download PDF

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Publication number
EP0783560B1
EP0783560B1 EP95934068A EP95934068A EP0783560B1 EP 0783560 B1 EP0783560 B1 EP 0783560B1 EP 95934068 A EP95934068 A EP 95934068A EP 95934068 A EP95934068 A EP 95934068A EP 0783560 B1 EP0783560 B1 EP 0783560B1
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EP
European Patent Office
Prior art keywords
alkyl
formula
weight
carbon atoms
disinfectant
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
Application number
EP95934068A
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German (de)
English (en)
French (fr)
Other versions
EP0783560A1 (de
Inventor
Gregory Van Buskirk
Eva Kiewert
Birgit Middelhauve
Karl-Heinz Disch
Carsten Friese
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Ecolab GmbH and Co OHG
Original Assignee
Henkel Ecolab GmbH and Co KG
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Filing date
Publication date
Application filed by Henkel Ecolab GmbH and Co KG filed Critical Henkel Ecolab GmbH and Co KG
Priority to EP00108422A priority Critical patent/EP1018542A1/de
Publication of EP0783560A1 publication Critical patent/EP0783560A1/de
Application granted granted Critical
Publication of EP0783560B1 publication Critical patent/EP0783560B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • C11D1/8355—Mixtures of non-ionic with cationic compounds containing a combination of non-ionic compounds differently alcoxylised or with different alkylated chains
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/40—Monoamines or polyamines; 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups

Definitions

  • the invention relates to the use of alkyl glycosides and alkyl ethers to strengthen the germ-reducing effect of disinfectant-containing Hard surface cleaners and disinfectant cleaners for hard surfaces with selected disinfectants. All non-textile that occur in the household are hard surfaces Understand surfaces, e.g. B. floors, work surfaces, kitchen appliances, Sinks, shower and bath tubs, toilet bowls, dishes etc.
  • Disinfectant cleaning agents are known; so far, however, it is not successful, optimal cleaning performance and optimal disinfection effect connect with each other.
  • Common disinfectant detergents included e.g. quaternary ammonium compounds in connection with nonionic surfactants; such cleaning agents have sufficient disinfectants Effect, their cleaning performance leaves something to be desired.
  • a replacement of the non-ionic surfactants by cleaning agents anionic surfactants have the disadvantage that the disinfectant effect wears off strongly.
  • the object of the present invention is based on disinfectant-containing Prior art cleaning agents such surfactant combinations to find the - in addition to good cleaning performance - for an increase in the germ-reducing effect of the detergents disinfectant contained.
  • Another job is to use detergents for hard surfaces to develop selected disinfectant agents that both have a good cleaning performance as well as a good disinfectant effect.
  • German published documents DE 34 44 958 and DE 36 19 375 describe the use of alkyl glycosides as potentiating agents Increasing the microbicidal activity of biguanide compounds or Alcohols and carboxylic acids, especially in personal care products.
  • European patent application EP-A-0 106 692 discloses cleaning agents which contain polyethylene glycol, nonionic surfactants, polysaccharides (preferably with a C 12 -C 14 alkyl chain) and quaternary ammonium compounds.
  • German patent application DE 40 07 758 disinfectants Detergent for automatically operated systems for Spray disinfection of hospital furnishings described a quaternary ammonium compound and the reaction product as disinfectant of N-substituted propylenediamines with glutamic acid or Contain glutamic acid esters.
  • Alkyl and / or alkenyl oligoglycosides are known substances that obtained according to the relevant procedures of preparative organic chemistry can be. Representing the extensive literature referred to the documents EP-A1-0 301 298 and WO 90/3977.
  • the alkyl and / or alkenyl oligoglycosides can differ from aldoses or Derive ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or Alkenyloligoglycosides.
  • the alkyl or alkenyl radical R 1 can be derived from primary alcohols with preferably 8 to 11 carbon atoms. Typical examples are caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, Palmoleyla alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and their technical mixtures.
  • the alkyl ethers of the formula II are known nonionic surfactants which are obtained by adding initially propylene oxide and then ethylene oxide or exclusively ethylene oxide to fatty alcohols.
  • Typical examples are alkyl ethers of the formula (II) in which R 2 represents an alkyl radical having 12 to 18 carbon atoms, x represents 0 or 1 and y represents numbers from 2 to 5.
  • the indices x and y represent mean values.
  • alkyl ethers of the formula II are, for. B. C 12-14 fatty alcohol x 6 E0, octanol x 4 E0 and C 10-14 fatty alcohol x 1 P0 x 6 E0; E0 stands for ethylene oxide, P0 stands for propylene oxide.
  • the alkyl ethers of the formula II can preferably have a narrow homolog distribution; in these cases, formulations with particularly advantageous physical properties are obtained.
  • the nitrogenous substances listed under A) are compounds whose antimicrobial effectiveness is known; in the patent US 4,652,585 describes several synthesis possibilities in detail.
  • the aliphatic amines mentioned under B) are tertiary amines, which are at least carry one, but preferably two, aminoalkyl groups, where it is linear alkyl groups with 2 to 6 carbon atoms, preferably the Propyl group.
  • Such substances are commercially available, e.g. N, N-bis (3-aminopropyl) dodecylamine, which is sold under the name Lonzabac 12 is offered by Lonza.
  • the quaternary ammonium compounds mentioned under C) are also commercially available Substances. Examples include dimethyldioctyl ammonium chloride, Didecyl-dimethyl-ammonium chloride, didodecyl-dimethyl-ammonium chloride, Dimethyl-ditetradecyl-ammonium chloride, dihexadecyl-dimethylammonium chloride, Decyl-dimethyl-octyl-ammonium chloride, dimethyl-dodecyloctylammonium chloride, Benzyl-decyl-dimethyl-ammonium chloride, benzyl-dimethyl-dodecyl-ammonium chloride, Benzyl-dimethyl-tetradecylammoniumchlorid, Decyl-dimethyl- (ethylbenzyl) -ammonium chloride, decyl-dimethyl- (dimethylbenzyl) -ammoni
  • alkyl and / or alkenyl oligoglycosides of the formula I in an amount of 0.1 to 20% by weight is particularly preferred, especially in an amount of 0.2 to 10 wt .-%, based on the total detergent;
  • Alkyl ethers of formula II are preferably in an amount of 0.05 up to 20 wt .-%, in particular 0.1 to 10 wt .-%, based on the total Detergent included.
  • An increase in the germ-reducing effect of the detergents Disinfectant contained is particularly with disinfectant quantities from 0.01 to 5% by weight, in particular 0.02 to 3% by weight on all detergents.
  • Another object of the invention are disinfectant cleaning agents for hard surfaces, good cleaning performance and good disinfectant effect connect with each other in a very special way.
  • Such cleaning agents are obtained if alkyl and / or alkenyl oligoglycosides of the formula I with an alkyl chain length limited to C 8 to C 10 are used, otherwise the alkyl ethers of the formula II already described above are used, alkyl chain lengths of C 8 to C 14 being preferred , and used as disinfectant one or more of the compounds listed above under A, B or C.
  • the cleaning agents according to the invention have very particularly positive properties if the disinfectant is selected from the substances mentioned under A above and the substances mentioned above under B, where V n in the formula is 3, R 6 is an alkyl radical with 12 to 16 carbon atoms. Represents atoms and R 7 is an aminopropyl radical.
  • All substances used in the cleaning agents can of course not only be used as pure substances, but also in the form of mixtures of different representatives of a compound class; for example, the simultaneous use of a C 8-10 alkyl glycoside and a C 12-16 alkyl glycoside is possible (e.g. in a ratio of 10: 1 to 1: 2), or the simultaneous use of an ethoxylated alkyl ether and an alkyl ether which both propoxylates and is also ethoxylated.
  • Mixtures of disinfectants can also be used, e.g. a disinfectant named under A together with one under B disinfectants mentioned.
  • alkyl and / or alkenyl oligoglycosides of the formula I and the alkyl ethers of formula II can optionally other nonionic surfactants in amounts of up to 20% by weight, based on the total cleaning agent, be included.
  • nonionic surfactants include e.g. Ethylene oxide addition products Fatty acids, fatty amines or fatty acid amides.
  • end group-locked Derivatives of such alkoxylation products, preferably with end groups, that contain 2 to 10 carbon atoms are possible.
  • amphoteric or zwitterionic surfactants can optionally be present in an amount of up to 10% by weight, based on the total cleaning agent.
  • Suitable amphoteric surfactants include derivatives of tertiary aliphatic amines or quaternary aliphatic ammonium compounds, the aliphatic radicals of which can be straight-chain or branched and one of which carries a carboxy, sulfo, phosphono, sulfato or phosphato group.
  • amphoteric surfactants are dimethyl-tetradecyl-glycine, dimethyl-hexadecyl-glycine, dimethyl-octadecyl-glycine, 3- (dimethyl-dodecylammonio) -1-propanesulfonate and those under the names Dehyton (R) AB, CB, K and G (Supplier Henkel) distributed amphoteric surfactants.
  • Anionic surfactants such as Fatty alcohol sulfates, fatty alcohol ether sulfates, In principle, ⁇ -olefin sulfonates can be used in small amounts of 10 % By weight, in particular up to 5% by weight, based on the total cleaning agent, be included, preferably in the cleaning agents described however contain at most 2% by weight of anionic surfactants.
  • anionic surfactants there it is self-evident for the expert that he the compatibility of the anionic surfactants with the disinfectants contained in the cleaning agents Verify agents for the germ-reducing effect got to.
  • the cleaning agents described can be water-soluble organic Solvents, preferably from the groups of alcohols with 1 to 4 carbon atoms, the glycols with 2 to 4 carbon atoms and the derivable from these Diglycols and diglycol ethers.
  • solvents are for example methanol, ethanol, propanol, isopropanol, tert-butanol, Ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, dipropylene glycol, Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Diethylene glycol monopropyl ether and diethylene glycol monobutyl ether.
  • organic Solvents can be used in amounts of about 5 to 40, preferably about 10 to 20 wt .-% can be used.
  • the detergents can contain conventional additives, e.g. dyes or fragrances, thickeners, hydrotropes, opacifiers etc. contain.
  • Amine oxides are preferably contained at most in amounts of up to 2% by weight, in particular, disinfectant cleaning agents are according to the invention but free of amine oxides.
  • Another object of the invention is a method for disinfecting Cleaning hard surfaces, characterized in that one of the like Detergent-containing cleaning agents described above in undiluted Form or in the form of a preparation diluted with water on a hard surface is applied and then the surface in the usual Way is cleaned.
  • the content is of disinfectant 0.01 to 5 wt .-%, based on the total cleaning agent.
  • the detergent is diluted with water, there is an application concentration from 0.001 to less than 5% by weight, in particular from 0.001 up to 0.05 wt .-%, advantageous.
  • the detergent can form complexing agents contain.
  • Examples include the sodium salts of methane diphosphonic acid, Hydroxyethane-1,1-diphosphonic acid, 1-aminoethane-1,1-diphosphonic acid, Amino-trimethylenephosphonic acid, ethylenediamine-tetra (methylenephosphonic acid), Diethylenetriamine penta (methylenephosphonic acid), 2-phosphonobutane-1,2,4-tricarboxylic acid and nitrilotriacetic acid (NTA).
  • NTA 2-phosphonobutane-1,2,4-tricarboxylic acid
  • Such complexing agents are preferably in the cleaning agents Quantities not exceeding 10% by weight, in particular approximately 0.5% by weight to 4% by weight, contain.
  • Dodigen TM 1611 (Hoechst) Coconut alkyl dimethyl benzyl ammonium chloride Lonzabac TM 12 (from Lonza) N, N-bis (3-aminopropyl) -C 12 alkylamine Bardac TM 22 (from Lonza) Didecyl dimethyl ammonium chloride Disinfectant I Reaction product of cocospropylene-1,3-diamine with L-glutamic acid prepared according to US 4,652,585 Fettalkoholoxylate: the alkyl chain of the fatty alcohol (FA) and the molar ethylene oxide (EO) or propylene oxide (PO) components are indicated.
  • FA fatty alcohol
  • EO molar ethylene oxide
  • PO propylene oxide
  • NRE denotes FA alkoxylates with narrow homolog distribution (narrow range ethoxylated)
  • Glucopon TM 225 Henkel
  • Glucopon TM 600 Henkel
  • C 12-16 alkyl 1,4-glucoside Sokalan TM DCS from BASF
  • Sodium salt of a dicarboxylic acid mixture adipic, glutaric, succinic acid
  • the germ-reducing effectiveness of the cleaning agents was tested in a quantitative suspension test based on the guidelines for the testing and evaluation of chemical disinfection processes of the German Society for Hygiene and Microbiology (DGHM), status 1981, against the bacterial strain Pseudomonas aeruginosa.
  • 10 ml of the cleaning agent to be tested was mixed with 0.1 ml of a germ suspension (approx. 10 8 - 10 9 germs per ml) at 20 ° C.
  • test method described below according to "Seifen- ⁇ le-Fette-Wwachs", 112 , 371, (1986) was used to test the cleaning ability and provides very reproducible results.
  • the cleaning agent to be tested was then placed on an artificially soiled plastic surface.
  • a mixture of carbon black, machine oil, triglyceride, saturated fatty acids and low-boiling aliphatic hydrocarbon was used as artificial soiling for the dilute use of the cleaning agent.
  • the test area of 26 x 28 cm was evenly coated with 2 g of the artificial soiling with the aid of a surface coater.
  • a plastic sponge was each with 10 ml of a 1 wt .-% aqueous Solution of the cleaning agent to be tested soaked and mechanically on the also with 10 ml of a 1% by weight aqueous solution of the test Detergent coated test area moves.
  • the cleaned test area was covered with flowing Water is kept and the loose dirt is removed.
  • the cleaning effect i.e. the whiteness of the plastic surface cleaned in this way measured with a color difference measuring device "Microcolor" (Dr. B. Lange).
  • the clean white plastic surface served as the white standard.
  • Disinfectant cleaning agents of the following compositions were produced (figures in% by weight): 1 2 (V) 3 (V) Glucopon 225 5 - 5 C 12-14 -FA + 6 E0 5 10 - C 12-14 -FA + 5 E0 + 5 P0 - - 5 Disinfectant I 1 1 1 Sokalan DCS 5 5 5 water ad 100 ad 100 ad 100
  • composition 1 has a germ reduction which is two orders of magnitude better than that of compositions 2 (V) and 3 (V). 4 5 (V) Glucopon 225 6 8th C 8 -FA + 1 P0 + 9 E0 2 - Disinfectant I 0.5 0.5 Bardac 22 0.5 0.5 Sokalan DCS 5 5 water ad 100 ad 100
  • Composition 4 is according to the invention, 5 (V) is a comparative example.
  • compositions have sufficient disinfectant properties; it turns out, however, that the joint use of APG 225 and C 8 -FA + 1 P0 + 9 E0 according to the invention leads to an increase in cleaning power.
  • compositions 6 to 18 used according to the invention have good cleaning ability and good germ-reducing effect.
  • Comparative composition 19 shows a significantly worse one Detergency.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Apparatus For Disinfection Or Sterilisation (AREA)
EP95934068A 1994-09-26 1995-09-18 Desinfizierende reinigungsmittel für harte oberflächen Expired - Lifetime EP0783560B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP00108422A EP1018542A1 (de) 1994-09-26 1995-09-18 Desinfizierende Reinigungsmittel für harte Oberflächen

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/312,354 US5576284A (en) 1994-09-26 1994-09-26 Disinfecting cleanser for hard surfaces
PCT/EP1995/003666 WO1996010069A1 (de) 1994-09-26 1995-09-18 Desinfizierende reinigungsmittel für harte oberflächen
US312354 1999-05-14

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP00108422A Division EP1018542A1 (de) 1994-09-26 1995-09-18 Desinfizierende Reinigungsmittel für harte Oberflächen

Publications (2)

Publication Number Publication Date
EP0783560A1 EP0783560A1 (de) 1997-07-16
EP0783560B1 true EP0783560B1 (de) 2002-04-10

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Application Number Title Priority Date Filing Date
EP95934068A Expired - Lifetime EP0783560B1 (de) 1994-09-26 1995-09-18 Desinfizierende reinigungsmittel für harte oberflächen
EP00108422A Withdrawn EP1018542A1 (de) 1994-09-26 1995-09-18 Desinfizierende Reinigungsmittel für harte Oberflächen

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Application Number Title Priority Date Filing Date
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Country Status (8)

Country Link
US (2) US5576284A (es)
EP (2) EP0783560B1 (es)
JP (1) JPH10506143A (es)
AT (1) ATE215983T1 (es)
DE (1) DE59510159D1 (es)
ES (1) ES2174961T3 (es)
PL (1) PL181663B1 (es)
WO (1) WO1996010069A1 (es)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2963101A1 (en) 2014-07-04 2016-01-06 Kolb Distribution Ltd. Hard surface cleaners

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ATE215983T1 (de) 2002-04-15
JPH10506143A (ja) 1998-06-16
PL318765A1 (en) 1997-07-07
DE59510159D1 (de) 2002-05-16
EP1018542A1 (de) 2000-07-12
EP0783560A1 (de) 1997-07-16
PL181663B1 (pl) 2001-08-31
ES2174961T3 (es) 2002-11-16
US5576284A (en) 1996-11-19
US5856290A (en) 1999-01-05
WO1996010069A1 (de) 1996-04-04

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