EP1863894B1 - Utilisation des acetales dans des detergents et nettoyants - Google Patents

Utilisation des acetales dans des detergents et nettoyants Download PDF

Info

Publication number
EP1863894B1
EP1863894B1 EP06723223A EP06723223A EP1863894B1 EP 1863894 B1 EP1863894 B1 EP 1863894B1 EP 06723223 A EP06723223 A EP 06723223A EP 06723223 A EP06723223 A EP 06723223A EP 1863894 B1 EP1863894 B1 EP 1863894B1
Authority
EP
European Patent Office
Prior art keywords
cleaners
formula
alkyl
washing
phenyl
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
EP06723223A
Other languages
German (de)
English (en)
Other versions
EP1863894A1 (fr
Inventor
Frank-Peter Lang
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.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant Produkte Deutschland GmbH
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 Clariant Produkte Deutschland GmbH filed Critical Clariant Produkte Deutschland GmbH
Publication of EP1863894A1 publication Critical patent/EP1863894A1/fr
Application granted granted Critical
Publication of EP1863894B1 publication Critical patent/EP1863894B1/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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/264—Aldehydes; Ketones; Acetals or ketals
    • 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
    • C11D3/2068—Ethers
    • 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
    • C11D3/43—Solvents

Definitions

  • Organic, water-soluble, partially water-soluble or water-insoluble solvents are used in a variety of detergents and cleaners. These include products for household use as well as products for commercial, industrial or institutional use.
  • the solvents can perform very different functions in the formulations. These include, for example, the reinforcement of the cleaning performance, in particular with regard to greasy and oily soiling, caused by, for example, food, (machine) oil, shoe polish, ointments, vaseline and cosmetics. In the case of specific stain remover, the removal of very special soiling is to be made possible by, for example, adhesives, chewing gum, nail polish, floor wax, resins, waxes and tar. Furthermore, the stabilization of formulations, an action as solubilizers, in particular also for highly concentrated or polymer-containing formulations, the improvement in the low-temperature stability and the "clarification" of opaque and slightly cloudy formulations should be mentioned.
  • Stain remover also called “stain water”
  • stain water can be used e.g. consist exclusively of aliphatic n- and / or iso-alkanes. In this case, one speaks of "benzine”.
  • solvents such as alcohols
  • Solvent-based softener for textiles composition (%) Distearyl dimethyl ammonium chloride 17.2 Polyethylene glycol 400 6.1 Stearylamine ethoxylate with 25EO 1.7 1,2-propanediol 7.5 MgCl 2 , 10% 1.5 HCI, 5N 0.25 Perfume 1.0 dye q.s. water ad 100
  • the following general-purpose cleaners can be used in the household for cleaning various surfaces made of plastic, linoleum, ceramic, stone, enamel, stainless steel, glass and other hard surfaces.
  • Table 6 Solvent-containing general-purpose cleaner A for hard surfaces composition (%) C 12/14 alkyl 5EO ether-Na-carboxylate, 90% 2.3 C 11 oxo alcohol 8EO polyglycol ether 2.5 Propylene glycol n-butyl ether 2.0 water ad 100 composition (%) Sec. Alkanesulfonate, 60% 1.7 C 11 oxo alcohol 8EO polyglycol ether 4.0 polycarboxylate 2.0 Propylene glycol n-butyl ether 0.5 water ad 100 composition (%) Sec. Alkanesulfonate, 30% 11.7 C 12/15 oxo alcohol EO / PO adduct 1.5 ethanol 2.5 Hydrogen peroxide, 35%, stabilized 2.0 Na-hydroxide solution qs water ad 100
  • Table 9 Solvent-containing hand dishwashing detergent composition (%) Sec. Alkanesulfonate, 60% 43.8% C 12/14 alkyl 2EO ether sulfate, Na salt, 27% 32.4% C 11 oxo alcohol 8EO polyglycol ether 1.0% terpenes , 4.0% Polyglycol 400 4.0% Perfume, dye, preservative q.s. water ad 100
  • Table 10 Solvent-based cleaning tablets for machine washing of dishes composition (%) C 8/10 -alcohol alkoxylate with 6 ethylene oxide and 2 propylene oxide 7.0 hydrocarbons 4.0 Na 5 P 3 O 10 55.0 soda 19.0 Na 2 O_2SiO 2 3.5 Zeolite A 0.4 borax 0.6 Hydroxyethane diphosphonic acid 0.2 protease 0.1 amylase 0.2 water 10.0
  • Glass cleaners are used to clean large areas of glass. These include, for example, windows, mirrors and glass tables. The cleaner must not leave any residue, eg in the form of stripes.
  • Table 12 Solvent-based glass cleaner A composition (%) C 12/14 alkyl 2EO ether sulfate, Na salt, 27% 0.5 Ammonia water, 25% 0.5 ethanol 29.0 water ad 100 composition (%) C 12/14 alkyl polyglycoside 0.5 Ammonia water, 25% 0.2 isopropanol 5.0 water ad 100 composition (%) Phosphorklamonomethylester 2.0 Oleyl-8EO polyglykolether 0.3 C 12/15 oxo alcohol 8EO polyglycol ether 0.3 isopropanol 10.0 water ad 100
  • Bathroom cleaners are used, for example, to remove limescale or lime soap residue from sanitary objects, tiles and fittings. You can also include organic solvents. Table 16: Solvent-based bathroom cleaner composition (%) Fettalkoholpolyglykosid 2.0 Octanol-4EO polyglykolether 3.0 Citric acid, 50% 0.5 isopropanol 3.0 water ad 100
  • the prior art solvents have their own specific disadvantages.
  • the flash point of ethanol or isopropanol at 12 ° C is very low, which also limits the use concentrations in detergents and cleaners.
  • the fat-solubility of these alcohols is limited.
  • glycol ethers have a high flash point, which is, for example, about 80 ° C. for dipropylene glycol monomethyl ether, the solubility for fats and oils is also limited here.
  • aliphatic hydrocarbons which due to their lipophilic properties have a very good dissolving power for greasy and oily stains, can only be incorporated to a limited extent in the aqueous surfactant systems.
  • the object of the present invention is to provide organic solvents which have a very good dissolving power for fats and oils and at the same time a sufficient polarity, so that the incorporation into aqueous preparations in wide concentration ranges is possible without any problems.
  • EP 1 184 448 aqueous fluids containing an acetal and a surfactant are described. These liquids, in contrast to the washing and cleaning agents according to the invention described below, are present only in the form of microemulsions or as liquid crystalline phases.
  • the acetals serve in EP 1 184 448 only as a solubilizer. The actual cleaning performance is provided by conventional surfactants.
  • radicals R 1 to R 4 are, for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-amyl iso-amyl, tert-amyl, neopentyl, cyclopentyl, n-hexyl, iso-hexyl, cyclohexyl, octyl, decyl, isotridecyl, phenyl, benzyl, phenylethyl, nonylphenyl.
  • the compounds of the general formula (1) are acetals. Acetals are generally obtained by the reaction of aldehydes with 2 moles of an alcohol per carbonyl group in the presence of catalysts such as dry hydrogen chloride.
  • dialdehydes must be used. Preferred dialdehydes for the synthesis of compounds of formula (1) are glyoxal, malondialdehyde (1,3-propanedial, 1,3-propanedialeddehyde), 1,4-butanedial and terephthalaldehyde. A most preferred dialdehyde is glyoxal.
  • a particularly preferred compound for the described application is tetramethoxyethane (2).
  • the invention also provides the use of the compounds of the formula (2) for cleaning and loosening soiling of solid surfaces.
  • Solid surfaces which can be cleaned with the acetals of the formula (1) or (2) are especially textile fibers but also metallic or ceramic surfaces, glass, porcelain or plastics.
  • the solvents of formula (1) and especially tetramethoxyethane (2) can be used in liquid detergents, washing pastes, washing gels, prewash sprays, washing boosters, stain sprays, stain removers, fabric softeners, all-purpose cleaners, hand dishwashing detergents, automatic dishwashing detergents, dishwashing rinse aids, oven cleaners, grill cleaners , Glass cleaners, stainless steel cleaners, bathroom cleaners, kitchen cleaners, carpet cleaners, cold cleaners (engine cleaners), tar removers, insect removers, auto dryers for Car washes, car window cleaners, car shampoos, wax film removers, rim cleaners, spray extraction cleaners, brush cleaners, polishing pastes and plastic cleaners.
  • acetals of the formula (1) have a low volatility, which can be achieved by the choice of the radicals R1 to R4, for example by the choice of long alkyl radicals, these can also be used in solid detergents and cleaners which For example, as a powder, granules, pellets, wax, as a wash or in the form of tablets may be present.
  • the acetals of formula (1) can be successfully used in those washing, cleaning and care products, as described initially in Tables 1 to 26, which is incorporated herein by reference.
  • the acetals of the formula (1) can completely or partially replace the organic solvents specified therein in these agents.
  • the amount of acetal of formula (1) in detergents and cleaners can vary widely and depends on the specific composition of such detergents and cleaners in each particular case.
  • Prewash sprays, wash enhancers and stain sprays may contain alcohols such as ethanol and isopropanol, glycol ethers such as dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, isoalkanes, N-methylpyrrolidone, anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, soap, water and 1 to 90%, preferably 5 to 80%, particularly preferably 10 to 60% and very particularly preferably 11 to 40% of the solvents of the formula (1), in particular tetramethoxyethane (2).
  • alcohols such as ethanol and isopropanol
  • glycol ethers such as dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, isoalkanes, N-methylpyrrolidone
  • anionic surfactants nonionic surfactants
  • cationic surfactants cationic surfactants
  • amphoteric surfactants soap
  • the stain sprays also support the removal of bleachable stains such as red wine stains, fruit juice stains, etc.
  • they may also contain hydrogen peroxide or other bleaching agents.
  • the application of the solvents of the formula (1) and the bleaching agent, for example hydrogen peroxide can then be carried out from two separate chambers, wherein the solvent of the formula (1) and the bleaching agent with each other and with the surface to be cleaned only when applied , eg of a textile.
  • Stain removers may contain from 1 to 100%, preferably from 1 to 80%, more preferably from 1 to 60% and particularly preferably from 1 to 40% of the solvents of the formula (1), in particular tetramethoxyethane (2).
  • other volatile organic solvents may be included, e.g. Alcohols and hydrocarbons.
  • Liquid detergents may include: anionic surfactants, nonionic surfactants, cationic surfactants (eg in the case of wool detergents) and amphoteric surfactants, soap, builders, enzymes, optical brighteners, polymers such as soil release polymers (especially those produced by the reaction of dicarboxylic acids such as terephthalic acid and Diols are obtained), color transfer inhibitors (for example polyvinylpyrrolidone) and polycarboxylates, complexing agents, water, dyes, perfume, and 0.5 to 20%, preferably 1 to 10% and particularly preferably 2 to 5% of the solvent of formula (1), in particular Tetramethoxyethane (2).
  • anionic surfactants eg in the case of wool detergents
  • cationic surfactants eg in the case of wool detergents
  • amphoteric surfactants soap, builders, enzymes, optical brighteners
  • polymers such as soil release polymers (especially those produced by the reaction of dicarboxylic acids such as ter
  • All-purpose cleaners may contain: anionic surfactants, nonionic surfactants, amphoteric surfactants, soap, phosphates, phosphonic acids and / or citric acid in free form or as salt, urea, hydrotrope (cumene sulfonate), polymers such as polycarboxylates, dyes, perfume, water and 0.1 to 20%, preferably 0.2 to 15%, particularly preferably 0.5 to 10% and very particularly preferably 1 to 5% of the solvents of the formula (1), in particular tetramethoxyethane (2).
  • Glass cleaners may contain: anionic surfactants, nonionic surfactants, amphoteric surfactants, ammonia water, phosphoric acid esters, water and 1 to 99%, preferably 2 to 50%, more preferably 3 to 40% and most preferably 5 to 30% of the solvents of formula (1 ), in particular tetramethoxyethane (2).
  • Cold cleaners may contain: hydrocarbons, anionic surfactants, nonionic surfactants, amphoteric surfactants, water in very small amounts and 1 to 99%, preferably 2 to 50%, more preferably 3 to 40% and most preferably 5 to 30% of Solvents of the formula (1), in particular tetramethoxyethane (2).
  • Car dryers for carwashes may contain: cationic surfactants, amphoteric surfactants, nonionic surfactants, siloxanes, hydrocarbons, water, and 0.5 to 20%, preferably 1 to 15%, more preferably 2 to 10% and most preferably 3 to 6% of the Solvents of the formula (1), in particular tetramethoxyethane (2).
  • Windscreen cleaners for cars may contain: anionic surfactants, amphoteric surfactants, nonionic surfactants, water and 1 to 99%, preferably 2 to 50%, more preferably 3 to 40% and most preferably 5 to 30% of the solvents of formula (1), in particular Tetramethoxyethane (2).
  • Hand dishwashing detergents may contain: anionic surfactants, nonionic surfactants, betaines, amine oxides, pearlescers, pH regulators such as citric acid, dyes, fragrances, water and 0.1 to 10%, preferably 0.5 to 7% and most preferably 1 to 5% of Solvent of formula (1).
  • Dishwashing rinse aids may contain: low-foaming nonionic surfactants, solubilizers / hydrotropes such as cumene sulfonate, citric acid and 0.5 to 10%, preferably 0.5 to 5% of solvent of formula (1).
  • Detergents and cleaners which contain the compounds of the formula (1) according to the invention may also contain further constituents. These are described below.
  • Suitable anionic surfactants are sulfates, sulfonates, carboxylates, phosphates and mixtures thereof.
  • Suitable cations here are alkali metals, e.g. Sodium or potassium or alkaline earth metals, e.g. Calcium or magnesium and ammonium, substituted ammonium compounds, including mono-, di- or triethanolammonium cations, and mixtures thereof.
  • the following types of anionic surfactants are particularly preferred: alkanesulfonates, alkyl sulfates, alkyl ether sulfates, alkylbenzenesulfonates, alkyl ester sulfonates and soaps, as described below.
  • Preferred alkyl ester sulfonates are compounds of the formula wherein R 1 is a C 8 -C 20 hydrocarbon radical, preferably alkyl, and R is a C 1 -C 6 hydrocarbon radical, preferably alkyl.
  • M represents a cation which forms a water-soluble salt with the alkyl ester sulfonate, for example sodium, potassium, lithium or ammonium cations, such as monoethanolamine, diethanolamine and triethanolamine.
  • Alkyl sulfates have the formula ROSO 3 M, wherein R is a C 10 -C 24 hydrocarbon radical, more preferably a C 12 -C 18 alkyl radical.
  • M is hydrogen or a cation, for example an alkali metal cation or ammonium or substituted ammonium.
  • Alkyl ether sulfates have the formula RO (A) m SO 3 M, where R is an unsubstituted C 10 -C 24 -alkyl or hydroxyalkyl radical, more preferably C 12 -C 18 -alkyl radical.
  • A is an ethoxy or propoxy moiety
  • m is a number preferably between about 0.5 and about 3
  • M is a hydrogen atom or a cation.
  • the preferred secondary alkanesulfonates contain linear alkyl chains of about 9 to 25 carbon atoms, preferably about 10 to about 20 carbon atoms, and more preferably about 13 to 17 carbon atoms.
  • the sulfo group can be attached to any secondary C atom.
  • the cation is preferably sodium.
  • the preferred alkylbenzenesulfonates contain linear alkyl chains preferably having from about 10 to about 13 carbon atoms, the cation being preferably sodium.
  • Olefinsulfonates are obtained by sulfonation of C 8 -C 24 -, preferably C 14 -C 16 - ⁇ -olefins with sulfur trioxide and subsequent neutralization.
  • anionic surfactants are salts of acylaminocarboxylic acids, acylsarcosinates, fatty acid-protein condensation products, salts of alkylsulfamidocarboxylic acids, salts of alkyl- and alkylarylethercarboxylic acids, alkyl and alkenyl glycerol sulfates, alkylphenol ether sulfates, alkyl phosphates, alkyl ether phosphates, isethionates, N-acyl taurides, alkyl succinates, sulfosuccinates, Monoesters of sulfosuccinates (especially saturated and unsaturated C 12 -C 18 monoesters) and diesters of sulfosuccinates (especially saturated and unsaturated C 12 -C 18 diesters), acyl sarcosinates, sulfates of alkyl polysaccharides such as sulfates of alkyl polyg
  • Nonionic surfactants are condensation products of native or synthetic, straight-chain or branched alcohols with about 1 to about 25 moles of ethylene oxide, mixed alkoxylates of these alcohols with ethylene oxide and propylene oxide or alcohol ethoxylates which are end-capped with an alkyl group such as butyl; Condensation products of ethylene oxide having a hydrophobic base formed by condensation of propylene oxide with propylene glycol; Condensation products of ethylene oxide with a reaction product of propylene oxide and ethylenediamine; Polyethylene, polypropylene and polybutylene oxide condensates of alkylphenols.
  • surfactants are amine oxides, fatty acid amides such as coconut fatty acid diethanolamide, alkyl and alkenyl oligoglycosides, fatty acid polyglycol esters, fatty amine polyglycol esters, alkyl oligoglycosides, alkenyl oligoglycosides, fatty acid N-alkylglucamides, betaines, e.g. Alkyldimethylammonium betaines, alkylamide betaines such as e.g. Cocoamidopropyl betaine, aminopropionates, aminoglycinates, or amphoteric imidazolinium compounds, aminopropionates, aminoglycinates, or amphoteric imidazolinium compounds.
  • Suitable cationic surfactants are substituted or unsubstituted straight-chain or branched quaternary ammonium salts of the type R 1 N (CH 3 ) 3 ⁇ X ⁇ , R 1 R 2 N (CH 3 ) 2 ⁇ X ⁇ , R 1 R 2 R 3 N (CH 3 ) ⁇ X ⁇ or R 1 R 2 R 3 R 4 N ⁇ X ⁇ .
  • the radicals R 1 , R 2 , R 3 and R 4 may preferably independently of one another unsubstituted alkyl having a chain length between 8 and 24 carbon atoms, in particular between 10 and 18 carbon atoms, hydroxyalkyl having from about 1 to about 4 C Atoms, phenyl, C 2 - to C 18 -alkenyl, C 7 - to C 24 -aralkyl, (C 2 H 4 O) x H, where x is from about 1 to about 3, one or more ester groups-containing alkyl radicals or cyclic quaternary ammonium salts.
  • X is a suitable anion.
  • detergent ingredients which may be included in the detergents and cleaners are alkali, ammonium and alkanolammonium salts of polyphosphates such as sodium tripolyphosphate; Phosphonates such as ethane-1-hydroxy-1,1-diphosphonate; Citric acid and its soluble salts; Carbonates (soda); Salts of polyacetic acids such as ethylenediaminetetraacetic acid and nitrilotriacetic acid; Polycarboxylates based on acrylic acid and maleic acid; Copolymers of maleic anhydride with ethylene or vinyl methyl ether; Soil Release Polymers, in particular Soll Release Polyester based on dicarboxylic acids and diols; Cellulose ethers such as methyl-hydroxyethyl or methyl-hydroxypropylcelluloses; Enzymes, in particular proteases, lipases, cellulases and amylases, mannanases; gall; Enzyme stabilizers, foam boosters, foam brakes
  • Example 1 Dissolving power of tetramethoxyethane for oil and grease dirt
  • Test fabric was dried after rinsing with clear water and then determined as a measure of the stain removal whiteness. The higher the whiteness, the better the red oil stain was washed out.
  • Table 1 Removal of paraffin oil from cotton / polyester fabric wfk 20A by tetramethoxyethane compared to reference solvents. Quantification about the whiteness.
  • Oil stain pretreated with test solvent Whiteness (%) tetramethoxyethane 82.5 and pretreated with reference solvents: Centralin 81.0 isopropanol 79.7 diglycol 81.1 dipropylene 74.3 tripropylene 74.4 Ethylene glycol phenyl ether 80.2 Propylene glycol phenyl ether 80.1
  • the color difference dE of the soiled and then washed fabric was determined to be the non-soiled tissue.
  • dE is equal to zero.
  • Table 2 Removal of paraffin oil from cotton / polyester fabric wfk 20A by tetramethoxyethane compared to reference solvents.
  • Example 2 Liquid detergent containing tetramethoxyethane
  • Table 3 Liquid detergent liquid detergent composition Hostapur SAS 60 13% Potassium coconut soap (27%) 10% Genapol LA-070 23% tetramethoxyethane 5% citric acid 1 % Dequest 2010 0.3% enzymes q.s. dye q.s. Perfume q.s. water ad 100%
  • Example 3 stain sprays, prewash sprays or washing intensifiers for textiles
  • Table 4 stain sprays Composition (%) Formulation: A B tetramethoxyethane 25 35 hydrocarbons 45 35 Genapol OX-030 15 15 refpagen HY 5 5 ethanol 10 10
  • Table 5 Prewash sprays Composition (%) Formulation: A B tetramethoxyethane 10 20 diglycol 10 10 isopropanol 10 5 Genapol UD-050 5 5 Hostapur SAS 30 3.5 - water ad 100 ad 100
  • Table 6 Wash booster Composition (%) tetramethoxyethane 5 Potassium coconut soap (27%) 10 Genapol LA-070 23 Hostapur SAS 60 13 citric acid 1 water ad 100
  • Table 8 Glass cleaner Composition (%) Formulation: A B tetramethoxyethane .29 14.5 ammonia water 0.5 0.5 ethanol - 14.5 Genapol LRO liq. 0.5 0.5 water ad 100 ad 100
  • Table 9 All-Purpose Cleaner Composition (%) Formulation: A B Hostapur SAS 60 1.7 1.7 Genapol UD-080 4 4 Sokalan CP 5 2 - Na citrate - 2 tetramethoxyethane 2 2 water ad 100 ad 100

Landscapes

  • 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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Cleaning By Liquid Or Steam (AREA)

Claims (8)

  1. Utilisation des composés de formule (1)
    Figure imgb0006
     dans laquelle
    A représente (CH2)a ou phénylène,
    R1, R2, R3 et R4, identiques ou indépendants les uns des autres, représentent n-et/ou iso-alkyle en C1 à C22, cycloalkyle en C5 ou C6, phényl-C1-C4-alkyle, alkylphényle en C1 à C13 ou phényle,
    et a est un nombre entier entre 0 et 6, pour le nettoyage et le détachage des salissures sur des surfaces solides.
  2. Utilisation selon la revendication 1, caractérisée en ce que l'on utilise un composé de formule (1), dans laquelle R1, R2, R3 et R4, identiques ou indépendants les uns des autres, représentent n- et/ou iso-alkyle en C1 à C13, cycloalkyle en C5 ou C6, phényl-C1-C2-alkyle, alkylphényle en C1 à C9 ou phényle et a est égal à un nombre entre 0 et 2.
  3. Utilisation selon la revendication 1, caractérisée en ce que l'on utilise un composé de formule (1), dans laquelle R1, R2, R3 et R4, identiques ou indépendants les uns des autres, représentent n- et/ou iso-alkyle en C1 à C8, cyclohexyle, benzyle ou phényle, et a est égal à 0 ou 1.
  4. Utilisation selon la revendication 1, caractérisée en ce que l'on utilise un composé de formule (1), dans laquelle R1, R2, R3 et R4, identiques ou indépendants les uns des autres, représentent n- et/ou iso-alkyle en C1 à C6, et a est égal à 0.
  5. Utilisation selon la revendication 1, caractérisée en ce que l'on utilise un composé de formule (1), dans laquelle R1, R2, R3 et R4, identiques ou indépendants les uns des autres, représentent méthyle et/ou éthyle et a est égal à 0.
  6. Utilisation selon la revendication 1, caractérisée en ce que l'on utilise un composé de formule (1), dans laquelle R1, R2, R3 et R4 se distinguent sur le plan de leur nombre d'atomes de C.
  7. Utilisation selon la revendication 1, caractérisée en ce que l'on utilise les composés de formule 1 dans une lessive liquide, des pâtes de lavage, des gels de lavage, des sprays avant lavage, des activateurs de lavage, des sprays détachants, des détachants, des adoucissants de rinçage, des détergents tous usages, des liquides vaisselles pour le lavage à la main, des détergents vaisselles pour le lavage en machine, des liquides de rinçage pour les lave-vaisselle, des produits nettoyants pour les fours, des produits nettoyants pour les grills, des détergents pour le verre, des détergents pour l'inox, des détergents pour la salle de bain, des détergents pour la cuisine, des détergents pour les tapis, des détergents à froid, des détergents dégoudronnants, des insecticides, des agents séchants automobiles pour les stations de lavage, des liquides lave-glace, des shampooings auto, des détergents enlevant les pellicules de cire, des nettoyeurs de jante, des nettoyeurs par extraction pulvérisation, des détergents applicables au pinceau, des pâtes de polish ou des nettoyants plastiques.
  8. Utilisation selon la revendication 1, caractérisée en ce que l'on utilise les composés de formule (1) dans un produit de lavage et de nettoyage qui se présente sous forme de poudre, de granulés, de granule, de cire, de pastille de lavage ou de comprimés.
EP06723223A 2005-03-15 2006-03-06 Utilisation des acetales dans des detergents et nettoyants Expired - Lifetime EP1863894B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005011719A DE102005011719A1 (de) 2005-03-15 2005-03-15 Wasch- und Reinigungsmittel enthaltend Acetale als organische Lösemittel
PCT/EP2006/002015 WO2006097214A1 (fr) 2005-03-15 2006-03-06 Detergents et nettoyants contenant des acetals comme solvants organiques

Publications (2)

Publication Number Publication Date
EP1863894A1 EP1863894A1 (fr) 2007-12-12
EP1863894B1 true EP1863894B1 (fr) 2008-08-13

Family

ID=36218428

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06723223A Expired - Lifetime EP1863894B1 (fr) 2005-03-15 2006-03-06 Utilisation des acetales dans des detergents et nettoyants

Country Status (6)

Country Link
US (1) US7632793B2 (fr)
EP (1) EP1863894B1 (fr)
JP (1) JP2008533253A (fr)
DE (2) DE102005011719A1 (fr)
ES (1) ES2312123T3 (fr)
WO (1) WO2006097214A1 (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006006022A1 (de) * 2006-02-08 2007-08-09 Clariant International Limited Verfahren zur Reinigung von Metallteilen
EP2431469A3 (fr) 2006-05-15 2012-05-30 Paratek Pharmaceuticals, Inc. Procédés de régulation de l'expression des gènes ou produits génétiques utilisant des composés tétracyclines substitués
US20080096785A1 (en) * 2006-10-19 2008-04-24 Air Products And Chemicals, Inc. Stripper Containing an Acetal or Ketal for Removing Post-Etched Photo-Resist, Etch Polymer and Residue
US9828597B2 (en) 2006-11-22 2017-11-28 Toyota Motor Engineering & Manufacturing North America, Inc. Biofunctional materials
US7828907B2 (en) * 2007-05-09 2010-11-09 Ecolab Inc. Detergent component for preventing precipitation of water hardness and providing soil removal properties
EP2367921B1 (fr) 2008-12-02 2020-02-05 Diversey, Inc. Nettoyage d'un dispositif ou d'un appareil de cuisson avec une composition comprenant un adjuvant de rinçage intégré
CA2745181C (fr) 2008-12-02 2017-09-26 Diversey, Inc. Systeme de lavage d'articles contenant un amidon cationique
US8470756B2 (en) * 2009-03-17 2013-06-25 S.C. Johnson & Son, Inc. Eco-friendly laundry pretreatment compositions
ES2378495T3 (es) 2009-07-17 2012-04-13 Clariant Finance (Bvi) Limited Composición de limpieza que cambia de color
US20110136715A1 (en) * 2009-12-07 2011-06-09 The Dial Corporation Color-changing pre-treatment stain removers and methods for fabricating the same
US9109191B2 (en) * 2009-12-15 2015-08-18 Invista North America S.A.R.L. Emulsion compositions and a method for selecting surfactants
JP5710229B2 (ja) * 2009-12-19 2015-04-30 ローム アンド ハース カンパニーＲｏｈｍ Ａｎｄ Ｈａａｓ Ｃｏｍｐａｎｙ フロアポリッシュ組成物
US8394618B2 (en) 2010-06-21 2013-03-12 Toyota Motor Engineering & Manufacturing North America, Inc. Lipase-containing polymeric coatings for the facilitated removal of fingerprints
US8796009B2 (en) 2010-06-21 2014-08-05 Toyota Motor Engineering & Manufacturing North America, Inc. Clearcoat containing thermolysin-like protease from Bacillus stearothermophilus for cleaning of insect body stains
US11015149B2 (en) 2010-06-21 2021-05-25 Toyota Motor Corporation Methods of facilitating removal of a fingerprint
US10988714B2 (en) 2010-06-21 2021-04-27 Regents Of The University Of Minnesota Methods of facilitating removal of a fingerprint from a substrate or a coating
US9121016B2 (en) 2011-09-09 2015-09-01 Toyota Motor Engineering & Manufacturing North America, Inc. Coatings containing polymer modified enzyme for stable self-cleaning of organic stains
US9388370B2 (en) 2010-06-21 2016-07-12 Toyota Motor Engineering & Manufacturing North America, Inc. Thermolysin-like protease for cleaning insect body stains
JP5242656B2 (ja) * 2010-10-08 2013-07-24 エバーライト ユーエスエー、インク 洗浄剤組成物
DE102017113141A1 (de) * 2017-06-14 2018-12-20 Westfälische Wilhelms-Universität Münster Elektrolyt für Lithium-Ionen-Batterien
IT202100032414A1 (it) 2021-12-23 2023-06-23 Andrea Macchia Composizione green pulente per la rimozione di vernici invecchiate da opere policrome di interesse storico artistico.

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2194405A (en) 1940-03-19 Process of producing tetba-acetals
GB559362A (fr) 1900-01-01
US2321094A (en) 1941-03-18 1943-06-08 Carbide & Carbon Chem Corp Tetraacetals of glyoxal with glycol monoethers and process of making them
US2591289A (en) * 1948-08-17 1952-04-01 Roger F Powell Frothing agents for use in froth flotation processes
GB701821A (en) * 1950-07-05 1954-01-06 Distillers Co Yeast Ltd Froth flotation process
BE534688A (fr) 1954-01-08
DE1225800B (de) * 1964-01-11 1966-09-29 Henkel & Cie Gmbh Schaumarme Spuel- und Reinigungsmittel
DE2132898A1 (de) * 1971-07-02 1973-01-18 Henkel & Cie Gmbh Schwachschaeumendes wasch-, reinigungsund enthaertungsmittel
US4216105A (en) * 1972-07-26 1980-08-05 Hickson & Welch Limited Compositions for the optical whitening of organic materials and use thereof
US4541837A (en) 1979-12-11 1985-09-17 Aeci Limited Fuels
US4619668A (en) 1985-09-11 1986-10-28 The United States Of America As Represented By The Secretary Of Agriculture Dyed wrinkle-resistant and durable-press cotton fabrics
US5191127A (en) 1991-08-13 1993-03-02 Loyola University Of Chicago Glyoxal derivatives and method for making the same
US5269958A (en) 1993-01-13 1993-12-14 S. C. Johnson & Son, Inc. Self-pressurized aerosol spot dry cleaning compositions
EP0801157B1 (fr) 1996-03-27 2003-01-29 Kuraray Co., Ltd. Fibres de copolymères d'éthylène-alcool polyvinylique et leur fabrication
DE19651325A1 (de) 1996-12-11 1998-06-18 Basf Ag Verfahren zur Herstellung von Glyoxalmonoacetalen
US7008458B2 (en) 1997-04-04 2006-03-07 Hayday William A Biodegradable ether dry cleaning solvent
GB9714707D0 (en) 1997-07-11 1997-09-17 Johnson & Son Inc S C Compositions suitable for use in aerosol dispensers
JPH1143818A (ja) * 1997-07-23 1999-02-16 Kuraray Co Ltd 保湿性繊維、その製造方法およびその染色方法
US6177070B1 (en) * 1998-01-05 2001-01-23 Una E. Lynch Deodorant composition
FR2792648B1 (fr) * 1999-04-22 2001-06-08 Atochem Elf Sa COMPOSITIONS DE NETTOYAGE OU DE SECHAGE A BASE DE 43-10mee ET DE TRICHLORETHYLENE
DE10042514A1 (de) * 2000-08-30 2002-03-14 Clariant Gmbh Wässerige Flüssigkeiten enthaltend ein Tensid und ein Acetal
DE10312562A1 (de) 2003-03-21 2004-09-30 Degussa Ag Verfahren zur kontinuierlichen Herstellung von Acetalen von α,β-Dicarbonylverbindungen
FR2855171B1 (fr) * 2003-05-22 2005-08-05 Clariant Procede de separation d'un diacetal du glyoxal d'un melange brut le contenant par extraction liquide-liquide a contre-courant
DE102005011722B4 (de) * 2005-03-15 2010-04-08 Clariant Produkte (Deutschland) Gmbh Verfahren zur chemischen Reinigung von Textilmaterial
DE102005011720A1 (de) 2005-03-15 2006-09-21 Clariant Produkte (Deutschland) Gmbh Neue amphiphile Acetale
DE102006006022A1 (de) * 2006-02-08 2007-08-09 Clariant International Limited Verfahren zur Reinigung von Metallteilen
US20080096785A1 (en) * 2006-10-19 2008-04-24 Air Products And Chemicals, Inc. Stripper Containing an Acetal or Ketal for Removing Post-Etched Photo-Resist, Etch Polymer and Residue
FR2910784B1 (fr) * 2006-12-27 2009-02-20 Arkema France Utilisation de composes pour la conservation du corps humain ou animal et compositions les comprenant
WO2008154617A2 (fr) * 2007-06-12 2008-12-18 Rhodia Inc. Composition de nettoyage pour surface dure avec agent d'hydrophilisation et procédé pour nettoyer des surfaces dures
DE602007013890D1 (de) * 2007-07-26 2011-05-26 Procter & Gamble Reinigungszusammensetzung für harte Oberflächen

Also Published As

Publication number Publication date
JP2008533253A (ja) 2008-08-21
DE102005011719A1 (de) 2006-09-28
ES2312123T3 (es) 2009-02-16
WO2006097214A1 (fr) 2006-09-21
DE502006001336D1 (de) 2008-09-25
EP1863894A1 (fr) 2007-12-12
US7632793B2 (en) 2009-12-15
US20080194453A1 (en) 2008-08-14

Similar Documents

Publication Publication Date Title
EP1863894B1 (fr) Utilisation des acetales dans des detergents et nettoyants
EP0808354B1 (fr) Detergents aqueux s'epaississant pour surfaces dures
CN103228667B (zh) 新水溶助长剂、其使非离子型表面活性剂可溶的用途和含有它的组合物
US11555164B2 (en) Alkaline hard surface cleaners comprising alkylpyrrolidones
EP3015540B1 (fr) Nettoyants de surfaces dures comprenant des tensioactifs non ioniques alcoxylés éthoxylés
JP2021528542A (ja) 液体洗濯洗剤組成物
DE69603162T3 (de) Reinigungsmittel enthaltend ein quaternisiertes polydimethylsiloxan und ein nichtionisches tensid
EP3835399B1 (fr) Agent de nettoyage pour surfaces dures
DE102005027605A1 (de) Geschirrspülmittelformulierungen enthaltend Oligoester
DE102005027604A1 (de) Reinigungsmittel für harte Oberflächen
US9957467B2 (en) Hard surface cleaners comprising ethoxylated alkoxylated nonionic surfactants
US20170369817A1 (en) Hard surface cleaning compositions
EP1409624B1 (fr) Detergents pour lave-vaisselle comportant des tensioactifs a tension superficielle dynamique basse
EP1229103B1 (fr) Hydroxyéthers mixtes à haut degré d'éthoxylation
EP1308499A1 (fr) Melangé tensioactif avec hydroxy-ethers mixtes et polyméres
EP1904613B1 (fr) Produits de nettoyage et d'entretien presentant une emulsibilite amelioree
EP3250668B1 (fr) Lessive liquide acide à faible teneur en eau, contenant de l'acide hydroxycarboxylique, un tensioactif neutre et une -amylase
DE19504006A1 (de) Hochalkalisches Waschmittel mit schmutzablösevermögendem Polymer
EP4053254B1 (fr) Composition de nettoyage de surfaces dures comprenant de polyalkylèneglycol
EP2904084A1 (fr) Détergents dotés d'agents complexants ii, de performance améliorée
DE102009002020A1 (de) Reinigungsmittel für Böden
WO2014056743A1 (fr) Compositions détergentes liquides contenant du savon, un tensioactif de type sulfo-estolide et une cellulase
WO2026012805A1 (fr) Détergent, procédés correspondants, kit correspondant et utilisations correspondantes
WO2015104162A1 (fr) Détergents contenant un alcanolamide
DE102011086639A1 (de) Nichtionische Tenside als Soil-Release-Wirkstoffe

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20071015

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

RTI1 Title (correction)

Free format text: USE OF ACETALES IN WASHING AND CLEANING AGENTS

DAX Request for extension of the european patent (deleted)
GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

RBV Designated contracting states (corrected)

Designated state(s): BE CH DE ES FR GB IE IT LI

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE CH DE ES FR GB IE IT LI

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Free format text: NOT ENGLISH

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

Free format text: LANGUAGE OF EP DOCUMENT: GERMAN

REF Corresponds to:

Ref document number: 502006001336

Country of ref document: DE

Date of ref document: 20080925

Kind code of ref document: P

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2312123

Country of ref document: ES

Kind code of ref document: T3

REG Reference to a national code

Ref country code: IE

Ref legal event code: FD4D

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080813

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20090514

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20130220

Year of fee payment: 8

REG Reference to a national code

Ref country code: CH

Ref legal event code: PCOW

Free format text: NEW ADDRESS: PATENT MANAGEMENT INDUSTRIEPARK HOECHST / G 860, 65926 FRANKFURT AM MAIN (DE)

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20140319

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20140328

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20140319

Year of fee payment: 9

REG Reference to a national code

Ref country code: DE

Ref legal event code: R082

Ref document number: 502006001336

Country of ref document: DE

Representative=s name: ACKERMANN, JOACHIM KARL WILHELM, DIPL.-CHEM. D, DE

REG Reference to a national code

Ref country code: DE

Ref legal event code: R082

Ref document number: 502006001336

Country of ref document: DE

Representative=s name: ACKERMANN, JOACHIM KARL WILHELM, DIPL.-CHEM. D, DE

Effective date: 20140905

Ref country code: DE

Ref legal event code: R081

Ref document number: 502006001336

Country of ref document: DE

Owner name: WEYLCHEM WIESBADEN GMBH, DE

Free format text: FORMER OWNER: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH, 65929 FRANKFURT, DE

Effective date: 20140905

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 10

REG Reference to a national code

Ref country code: ES

Ref legal event code: PC2A

Owner name: WEYLCHEM WIESBADEN GMBH

Effective date: 20150408

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20150320

Year of fee payment: 10

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20150319

Year of fee payment: 10

Ref country code: FR

Payment date: 20150319

Year of fee payment: 10

REG Reference to a national code

Ref country code: GB

Ref legal event code: 732E

Free format text: REGISTERED BETWEEN 20150730 AND 20150805

REG Reference to a national code

Ref country code: FR

Ref legal event code: TP

Owner name: WEYLCHEM WIESBADEN GMBH, DE

Effective date: 20150908

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20150306

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20150331

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20150331

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20160428

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20150307

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 502006001336

Country of ref document: DE

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20160306

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20161130

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20160306

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20161001

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20160331

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20150331