EP0876460A1 - Agent de nettoyage pour surfaces dures - Google Patents

Agent de nettoyage pour surfaces dures

Info

Publication number
EP0876460A1
EP0876460A1 EP96942274A EP96942274A EP0876460A1 EP 0876460 A1 EP0876460 A1 EP 0876460A1 EP 96942274 A EP96942274 A EP 96942274A EP 96942274 A EP96942274 A EP 96942274A EP 0876460 A1 EP0876460 A1 EP 0876460A1
Authority
EP
European Patent Office
Prior art keywords
weight
cleaning agent
agent according
formula
cleaning
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
Application number
EP96942274A
Other languages
German (de)
English (en)
Other versions
EP0876460B1 (fr
Inventor
Rainer Jeschke
Ludwig Schieferstein
Katica Bocarac
Paul Birnbrich
Herbert Fischer
Rainer Kade
Eva Kiewert
Dieter Nickel
Horst-Dieter Speckmann
Juan-Carlos Wuhrmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0876460A1 publication Critical patent/EP0876460A1/fr
Application granted granted Critical
Publication of EP0876460B1 publication Critical patent/EP0876460B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • 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
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0036—Soil deposition preventing compositions; Antiredeposition agents
    • 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
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
    • 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
    • C11D1/75—Amino oxides

Definitions

  • the present invention relates to the use of cationic polymers as soil release compounds in cleaning agents for hard surfaces.
  • the invention relates to cleaning agents for hard surfaces, which contain these cationic polymers as soil release compounds.
  • cleaning agents For cleaning hard surfaces that occur in the household and in the commercial sector, different cleaning agents are used, which differ both in the concentration of the cleaning agents and in the form of supply, e.g. B. concentrates, spray cleaners, gels, powders, as well as in pH, e.g. B. differentiate between acidic, neutral and alkaline cleaners.
  • the cleaning agents are essentially aqueous solutions of surfactants, which can contain builders, water-soluble solvents, solubilizers, water-soluble abrasives, etc. as additives. In order to be able to meet the requirements of the consumer, these cleaning agents should be effective against all types of soiling that occur.
  • the cleaning agents contained components which make it easier to remove dirt during the second and subsequent uses of the agents.
  • Such components are referred to as soil release connections.
  • Most of these are polymeric compounds. These polymers influence the surface of the objects to be cleaned in such a way that they have a positive effect on the detachment of dirt during the second and all further cleaning processes. They act in such a way that during the first cleaning cycle they have a certain tendency to settle on the cleaned surfaces (substantivity) and thus to change their surface properties.
  • the polymers do not form permanent films, but they can be mixed with aqueous solutions such. B. in the subsequent cleaning under certain circumstances very easily.
  • European patent application EP-A 0 467 472 describes a cleaning agent for hard surfaces which contains, as soil-release compounds, water-soluble anionic, cationic or nonionic polymers. Polymers which contain quaternized ammonium alkyl methacrylate groups in the molecule are given in particular as examples of such polymers.
  • the cleaning agents described in this document only have their dirt-repellent effect when the agent has already been applied to the hard surface.
  • the present invention is based on the object of providing compounds which, when used in aqueous surfactant solutions for manual cleaning of hard surfaces, act as soil-release compounds, the dirt detachment and stabilization of the detached dirt in the cleaning liquor already positive on first use influence or at least do not lower them, and show an increased substantivity to the surface compared to aqueous solutions, whereby the cleaning ability of the cleaning agent is improved with repeated use.
  • the invention relates to the use of cationic polymers, the monomer units of the formula I.
  • n is a number between 2 and 4, preferably 3, R 1 is hydrogen or a methyl group and
  • R 2 , R 3 and R A may be the same or different and represent hydrogen or a C - M alk (en) yl group
  • X represents an anion from the group of halide anions or a monoalkyl anion of sulfuric acid semiesters, contained as soil release compounds in cleaning agents for hard surfaces.
  • the cationic polymers of the invention act as soil release compounds in hard surface cleaners. Especially when cleaning hard surfaces manually, the dirt detachment and the stabilization of the detached dirt in the cleaning liquor is positively influenced and an improved substantivity on surfaces is achieved.
  • the polymers contain the monomer units of the formula I preferably in a proportion of 40 mol% to 100 mol%, particularly preferably more than 50 mol%. As a result, the polymers have a significant soil release effect.
  • unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid and the like
  • olefins such as ethylene, propylene and butene
  • alkyl esters of unsaturated carboxylic acids in particular esters of acrylic acid and methacrylic acid, and their alcohol components, of alkyl groups from 1 to 6
  • C atoms such as methyl acrylate, ethyl acrylate, methyl methacrylate, and their hydroxy derivatives such as 2-hydroxyethyl methacrylate
  • unsaturated groups such as styrene, methyl styrene, vinyl styrene and
  • the polymers used according to the invention can be present in the cleaning agents in an amount of 0.01 to 10% by weight, preferably 0.05 to 2% by weight, based on the total cleaning agent.
  • Another object of the present invention are aqueous cleaning agents for hard surfaces, the a) from 0.01 to 10 wt .-%, preferably from 0.05 to 2 wt .-%, cationic polymers, the monomer units with the formula I.
  • n is a number between 2 and 4, preferably 3, R 1 is hydrogen or a methyl group and R 2 , R 3 and R 4 can be the same or different and is hydrogen or a C 1 ⁇ -alk (s) yl group stand,
  • X represents an anion from the group of halide anions or a monoalkyl anion of sulfuric acid semiesters, and b) 0.1 to 50% by weight of one or more nonionic surfactants
  • nonionic surfactants which may be contained in the agents according to the invention, z. B. alkyl polyglycosides and C 8 -C 18 alkyl alcohol ethers and nitrogenous surfactants.
  • Alkyl polyglycosides are known nonionic surfactants and can be described by formula II
  • R 5 is an alkyl radical having 8 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms, preferably a glucose radical
  • p are numbers from 1 to 10.
  • Alkyl polyglycosides (APG) with the formula II can be obtained by the relevant methods of preparative organic chemistry. Representative of the extensive literature, reference is made here to the documents EP-A1-0 301 298 and WO 90/3977.
  • the alkyl polyglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl polyglycosides are thus alkyl polyglucosides.
  • R 6 is a linear or branched, aliphatic alkyl and / or alkenyl radical having 8 to 18 carbon atoms, c is 0 or numbers from 1 to 3 and d is numbers from 1 to 20.
  • the C 8 -C 18 alkyl alcohol polypropylene / polyethylene glycol ether with the formula III can be obtained by addition of propylene oxide and / or ethylene oxide to alkyl alcohols, preferably to fatty alcohols.
  • Typical examples are polyglycol ethers of the formula III, in which R 6 for an alkyl radical having 8 to 18 carbon atoms, c for 0 to 2 and d for numbers from 2 to
  • end-capped C 8 -C 8 -alkyl alcohol polyglycol ethers ie compounds in which the free OH group in the formula III is etherified.
  • the end-capped C ⁇ -Cis-alkyl alcohol polyglycol ethers can be obtained by the relevant methods of preparative organic chemistry.
  • C 8 -C 8 -alkyl alcohol polyglycol ethers are preferably reacted in the presence of bases with alkyl halides, in particular butyl or benzyl chloride.
  • Typical examples are mixed ethers of the formula III in which R 6 represents a technical " fatty alcohol radical, preferably C 1 -C 4 cocoalkyl radical, c represents 0 and d represents 5 to 10, which are sealed with a butyl group.
  • nonionic surfactants nitrogen-containing surfactants z.
  • the particularly suitable compounds include the lauric acid, myristic acid and palmitic acid monoethanolamides.
  • amphoteric or zwitterionic surfactants e.g. B. Beta surfactants or fatty amine oxides to mention.
  • the cleaning agents according to the invention can contain anionic surfactants as additional surfactant components.
  • the anionic surfactants can be present in amounts of 0.1 to 10% by weight, preferably 0.1 to 7.0% by weight, based on the total agent.
  • Anionic surfactants and cationic polymers are preferably present in a ratio of 20: 1 to 1:20, in particular 10: 1 to 1:10.
  • Suitable anionic surfactants are e.g. C 8 -C 18 alkyl sulfates, C ⁇ -Cm-alkyl ether sulfates, C 8 -C 8 -alkanesulfonates, C 8 -C 8 - ⁇ -olefin sulfonates, sulfonated C 8 -C 8 fatty acids, C 8 -C 8 alkylbenzene - Sulfonates, sulfonic succinic acid mono- and -di -CC- 2 -alkyl esters, C 8 -C 8 -alkyl polyglycol ether carboxylates, C 8 -C 8 -N-acyl taurides, C 8 -C 8 -N-sarcosinates and C 8 -C ⁇ 8 alkyl isethionates.
  • C 8 -C 18 alkyl sulfates C ⁇ -Cm-alkyl ether sulfates, C
  • inventive compositions may -F r ETT acids, also contain soaps, ie alkali metal or ammonium salts of saturated or unsaturated C 6 -C 22nd
  • soaps can be used in an amount of up to 5% by weight, preferably from 0.1 to 2% by weight.
  • the liquid cleaning agents for hard surfaces e.g. B. All-purpose cleaners and manual dishwashing detergents, contained conventional auxiliaries ent.
  • These substances are builders, such as. B. salts of glutaric acid, succinic acid, adipic acid, tartaric acid, benzene hexacarboxylic acid, gluconic acid, citric acid; Solvents such as B. ethanol, isopropanol, glycol ether; Hydrotropes such as B. cumene sulfonate, octyl sulfate, butyl glucoside, butyl glycol; Cleaning booster; Viscosity regulators, such as B.
  • the cleaning agent according to the invention is in the form of a ready-to-use solution which can be used in particular as a spray cleaner.
  • the cleaning agent according to the invention is in the form of a pourable cleaning agent concentrate which can additionally contain a water-soluble abrasive component.
  • Such cleaning agents contain a water-soluble salt, and are suitable in concentrated form as scouring agents and diluted as general-purpose cleaning agents.
  • the agents according to the invention are suitable both as aluminum-purpose cleaners and for manual cleaning of dishes, in particular of heavily soiled cookware
  • Suitable water-soluble abrasive components are in particular alkali metal carbonates, preferably sodium bicarbonate, which have an average grain size of approximately 200 ⁇ m ⁇ 100 ⁇ m.
  • the abrasive component is present in an amount of preferably more than 50% by weight, particularly preferably 50 to 65% by weight, based on the agent according to the invention
  • the agent according to the invention is preferably in the form of a gel.
  • the viscosity and thus the flow properties of the cleaning agents according to the invention can be increased by adding up to 5% by weight, preferably from about 0.3 to 3% by weight, of polyols of the formula HO-R-OH, in which R is an alkyl radical which is optionally substituted by hydroxyl groups with about 2 to 6, preferably 2 to 4 carbon atoms means positively influence.
  • the polyols include, for example, ethylene glycol, n- and iso-propylene glycols and glycine
  • Another possible additive consists of naturally occurring polymers and their derivatives such as xanthan gum, other polysaccharides and / or gelatin in amounts of up to 2% by weight, preferably about 0.1 to 1.0% by weight.
  • the agents according to the invention are particularly suitable for cleaning hard surfaces such as. B. Enamel, glass, porcelain, PVC and other plastics, linoleum, ceramic tiles, marble and metals.
  • the hand dishwashing detergents which are usually used for cleaning dishes, glasses, cutlery, pots, bowls etc.
  • the all-purpose cleaners which are usually used to clean larger areas in the household.
  • Polymer a poly-methacrylamidopropyltrimethylammonium chloride
  • Polymer b poly-methacrylamidopropyltrimethylammonium chloride-co-
  • the dynamic interfacial tension ⁇ G was determined for various oils with the drop / volume tensiometer (TVT1, Fa. Lauda, in accordance with the operating instructions) in order to be able to investigate the short-term kinetics when reducing the interfacial tension .
  • the following is representative of the time course of the interfacial tension ⁇ G [mN / m] for Mazola, a commercially available vegetable oil.
  • the ingredients of the cleaning formulations are shown in Table 1 and the test results for Examples B1 to B5 are shown in Table 2.
  • test results show that the hydrophilizing effect of the drying layer on the PVC surface can still be clearly determined even after a rinsing process when polymer is added. This effect occurs to a significantly lesser extent in detergents which contain the polymers known from EP-A-467 472, after which a significantly better soil release effect of the polymers according to the invention can also be shown.
  • a plastic sponge was impregnated with 10 ml of the detergent solution to be tested and mechanically on the also with 10 ml of the detergent to be tested coated test surface moves. After 10 wiping movements, the cleaned test area was kept under running water and the loose dirt was removed. The cleaning effect, ie the degree of whiteness of the so-called plastic surface, was measured using a "Microcolor" color difference measuring device (Dr. Lange). The clean, untreated white plastic surface served as the white standard.
  • the measurement of the clean surface corresponded to 100% and that of the soiled surface to 0%, so that the read values of the cleaned plastic surfaces could be equated with the percentage cleaning capacity (% RV).
  • % RV values given are the values determined by this method for the cleaning ability of the cleaning agents examined. They represent mean values from three identical experiments.
  • the measured values were used as the standard, AZR recipe not containing the polymers according to the invention.
  • Measured values sample x 100 / measured value standard % RV relative

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Detergent Compositions (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Physical Vapour Deposition (AREA)
  • Crystals, And After-Treatments Of Crystals (AREA)
  • Glass Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP96942274A 1995-12-07 1996-11-28 Agent de nettoyage pour surfaces dures Expired - Lifetime EP0876460B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19545630A DE19545630A1 (de) 1995-12-07 1995-12-07 Reinigungsmittel für harte Oberflächen
DE19545630 1995-12-07
PCT/EP1996/005266 WO1997020908A1 (fr) 1995-12-07 1996-11-28 Agent de nettoyage pour surfaces dures

Publications (2)

Publication Number Publication Date
EP0876460A1 true EP0876460A1 (fr) 1998-11-11
EP0876460B1 EP0876460B1 (fr) 2001-01-17

Family

ID=7779422

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96942274A Expired - Lifetime EP0876460B1 (fr) 1995-12-07 1996-11-28 Agent de nettoyage pour surfaces dures

Country Status (8)

Country Link
US (1) US6251849B1 (fr)
EP (1) EP0876460B1 (fr)
AT (1) ATE198764T1 (fr)
BR (1) BR9611692A (fr)
DE (2) DE19545630A1 (fr)
ES (1) ES2154422T3 (fr)
PT (1) PT876460E (fr)
WO (1) WO1997020908A1 (fr)

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ES2154422T3 (es) 2001-04-01
DE59606352D1 (de) 2001-02-22
WO1997020908A1 (fr) 1997-06-12
US6251849B1 (en) 2001-06-26
BR9611692A (pt) 1999-02-17
DE19545630A1 (de) 1997-06-12
EP0876460B1 (fr) 2001-01-17
ATE198764T1 (de) 2001-02-15
PT876460E (pt) 2001-06-29

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