WO2009115391A1 - Use of imidazolium salts in detergents and cleaning products - Google Patents

Use of imidazolium salts in detergents and cleaning products Download PDF

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Publication number
WO2009115391A1
WO2009115391A1 PCT/EP2009/052055 EP2009052055W WO2009115391A1 WO 2009115391 A1 WO2009115391 A1 WO 2009115391A1 EP 2009052055 W EP2009052055 W EP 2009052055W WO 2009115391 A1 WO2009115391 A1 WO 2009115391A1
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Prior art keywords
washing
cleaning agent
agent according
alkyl
cleaning
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PCT/EP2009/052055
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German (de)
French (fr)
Inventor
Mareile Job
Christian Kropf
Annemarie Krasemann
Ursula Huchel
Elke Veit
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Henkel Ag & Co. Kgaa
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Publication of WO2009115391A1 publication Critical patent/WO2009115391A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • 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
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • 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
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3281—Heterocyclic 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/34—Organic compounds containing sulfur

Definitions

  • the present invention relates to detergents and cleaning agents containing imidazolium salts and to the use of these detergents and cleaners for cleaning textiles and surfaces.
  • imidazolium salts in particular with respect to strongly baked-on dirt, allow a significant improvement in the cleaning performance of detergents and cleaners.
  • a first subject of the present invention are therefore detergents and cleaners containing at least one imidazolium salt.
  • Cleaning agents for hard surfaces in particular hand dishwashing detergents and automatic dishwasher detergents, are particularly preferred.
  • Another object of the present invention is therefore also the use of such imidazolium salts according to the invention and of detergents and cleaners containing such imidazolium salts, for the cleaning of surfaces, especially hard surfaces, as well as for the cleaning of textile fabrics.
  • a preferred object of the present invention is in particular the use of such imidazolium salts according to the invention and of detergents and cleaners which contain such imidazolium salts, for the removal of stubborn and / or baked-on, in particular strongly burned, stains.
  • a further preferred subject matter of the present application is furthermore a process for cleaning dishes in a dishwasher, in which a washing or cleaning agent according to the invention is metered into the interior of a dishwasher during the passage of a dishwashing program before the main wash cycle or during the main wash cycle.
  • the metering or the entry of the agent according to the invention into the interior of the dishwasher can be done manually, but preferably the agent is metered by means of the metering chamber into the interior of the dishwasher.
  • the imidazolium salt according to the invention is preferably a salt which contains as imidazolium cation a compound of general formula (I)
  • R1, R2, R3, R4 and R5 independently of one another represent trifluoromethyl, hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, heteroalkyl, heterocycloalkyl, alkoxy, alkoxyalkyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkanoyl, alkanoyloxy, alkoxycarbonyl, Alkylaminocarbonyl, alkylsulfanylcarbonyl, hydroxy, hydroxyalkyl, hydroxycarbonyl, amino, alkylamino, aryl, arylalkyl, aryloxy, arylamino, arylsulfanyl, arylsulfinyl, arylsulfonyl, arylcarbonyl, arylcarbonyloxy, aryloxycarbonyl, arylamino
  • R 1 and R 4 are independently optionally substituted alkyl, aryl, arylalkyl, alkylcarbonylalkyl or arylcarbonylalkyl, and R 2, R 4 and R 5 are independently hydrogen or optionally substituted alkyl.
  • R1 and / or R4 preferably both R1 and R4, comprise an aromatic radical.
  • R 1 and R 4 independently of one another are optionally substituted phenyl, phenyl-C 1-e-alkyl or phenylcarbonyl-C 1-e-alkyl and
  • Radicals R2, R4 and R5 are independently hydrogen or optionally substituted
  • R 1 is an optionally substituted phenacyl radical and / or R 4 is an optionally substituted phenylmethyl radical
  • the imidazohum cation is a compound according to formula (II) or formula (III)
  • said compounds may also be monosubstituted or polysubstituted.
  • substituents are preferably selected from alkyl, halogen, in particular chlorine, bromine, iodine or fluorine, hydroxypropyl, hydroxyalkyl, hydroxycarbonyl, alkoxy, alkoxyalkyl, alkoxycarbonyl, amino, alkylamino and dialkylamino.
  • the Anio ⁇ of the imidazolium salt is preferably selected from Haloge ⁇ id, in particular chloride, boron, iodide or fluoride. Sulfate, sulfite, nitrate, Hydrog ⁇ ncarbonat and deprotonated ⁇ n organic acids, more preferably it is a halide, especially bromide.
  • the washing performance can be further improved if the imidazolium salt is used in combination with salicylic acid (2-hydroxybenzoic acid), a salicylic acid or mixtures thereof.
  • the salicylic acid derivatives may be selected, in particular, from 2-hydroxybenzoic acid which is substituted by further radicals on the ring, the other radicals preferably being selected from hydroxyl, amino, halogen, in particular chlorine, bromine or fluorine, C 1 -b-alkyl, Ci- ⁇ -alkoxy, Cf- ⁇ -alkylamino and di (Ci-B-alkyl) amino.
  • the Ca rboxyl group and the hydroxy group of 2-Hydroxybenzoesä ⁇ re and salicylic acid derivatives may also be optionally esterified or etherified, in particular by optionally substituted Ci- ⁇ -Alka ⁇ ol.
  • Alkyl preferably represents C ⁇ . ie -alkyl. in accordance with the invention in each case independently of one another for all saturated linear and branched alkyl radicals having up to 18 C atoms, preference being given to C 1, B-alkyl radicals.
  • Ci "6-alkyl is according to the invention for all saturated linear and branched alkyl radicals having up to 6 C-Atom ⁇ n, i ⁇ sb ⁇ sond ⁇ re for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl and all isomers of pentyl and hexyl.
  • cycloalkyl is preferably Cs- ⁇ -cycloalkyl.
  • Cj- ⁇ -Cycloalkyl independently of one another in each case denotes all cyclic alkyl radicals having 3 to 6 C atoms, preferably 5 to 6 C atoms, where the radicals may be saturated or unsaturated, especially for cyclopentyl, cyclohexyl or cyclopentadienyl.
  • Alkenyl is C 2 -i erfindungsgem Kunststoff preferably a alkenyl.
  • C 2 -i fl -alkenyl erfi ⁇ du ⁇ gsgemad each independently for all linear and branched alkyl radicals having up to 18 carbon atoms, containing at least one double bond,
  • C 2-6 alkenyl radicals are preferably C 2 -.
  • Alkynyl is preferably ⁇ rfi ⁇ du ⁇ gsleton for in accordance with the invention, in each case independently of one another, denotes all linear and branched alkyl radicals having up to 18 C atoms which contain at least one triple bond, where C 2 . e- alkynyl radicals are preferred.
  • C 2 . 6 -Alkinyl stands erfindu ⁇ gsgemäl ⁇ for all linear and unbranched alkyl radicals having up to 6 carbon atoms which contain at least one triple bond, in particular ethynyl, propynyl, i-Propi ⁇ yl and all isomers of Butrnyl, Pe ⁇ tinyl and hexynyl.
  • Heteroalkyl according to the invention is in each case independently of one another for all saturated and mono- or polyunsaturated, linear or branched alkyl radicals which contain at least one, preferably exactly one heteroatom, in particular selected from O, S and N, where the sum of C and Hetero-Atome ⁇ preferably up to 18, more preferably up to 6 amounts.
  • Heterocycloalkyl according to the invention is in each case independently of one another for all cyclic alkyl radicals which contain at least one, preferably exactly one, heteroatom, in particular selected from O, S or N 1 , wherein the ring is preferably from three to eight membered, more preferably five to six membered , Examples of these are tetrahydrofuranyl, tetrahydrothiophenyl, pyrrolidinyl, 2-thiazolinyl, tetrahydrothiazolyl, tetrahydrooxazolyl, piperidinyl, pipazrazinyl, morpholinyl and thiomorpholmyl.
  • C 1-18 -alkoxy is preferably independently of each other all saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms which are bonded via an oxygen atom to C 1-16 -alkoxy.
  • C 1 -C alkoxy radicals are preferred, C 1-6 -alkoxy, according to the invention, in each case independently of one another for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 C atoms, which are bonded via an oxygen atom, in particular methoxy and ethoxy.
  • Ci-ie-alkylsulfanyl stands erfindu ⁇ gsge réelle preferably Ci_ig alkylsulfanyl.
  • Ci-ie-alkylsulfanyl is erfindu ⁇ gshack each independently, all saturated and unsaturated! Linear and branched alkyl radicals having up to 18 carbon atoms bonded via a sulfur atom, where C 1, ⁇ -alkylsulfinyl radicals are preferred
  • C 1 -alkylsulfanyl represents all saturated and unsaturated, linear and branched alkyl radicals having up to 6 C atoms which are bonded via a sulfur atom, in particular Methysulfanyl and Ethylsulfa ⁇ yl.
  • alkylsulfinyl is preferably C 1- al-alkynyl [sulfinyl.
  • C 1-6 -alkylsulfinyl according to the invention is, independently of one another, for all saturated and unsaturated, linear and branched alkyl radicals having up to 16 carbon atoms which have an SO group are bonded, said CI_ 6 -Alkylsulfo ⁇ yl radicals are preferred.
  • C ⁇ alkylsulfinyl stands according to the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 C-Atome ⁇ , which are bonded via an SO group, in particular for M ⁇ thylsulfi ⁇ yl and ethylsulfinyl.
  • alkylsulfonyl is preferably C 1 -C 4 -alkylsulfonyl.
  • C 1 -C 4 -alkylsulfonyl according to the invention in each case independently of one another for all saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms which are bonded via a SOjj group are, where C t - ⁇ -Alkylsulfoxidyl radicals are preferred.
  • C is preferably C 1 -C 4 -alkylsulfonyl.
  • 6 -AlkylsulFo ⁇ yl is erfindu ⁇ gsloom for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms which bound via a SO 2 group in particular for methylsulfonyl and ethylsulfonyl
  • C 1 -alkyl is in each case independently of each other saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms which, via a carbonyl radical, represent C 1-1 -alkanoyl.
  • Ci- 6 -alkanoyl is according to the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms, which are bonded via a carbonyl group , in particular For Methycarbo ⁇ yl and ethylcarbonyl.
  • alka ⁇ oyloxy is preferably Ci_is-alkanoyloxy.
  • Ci-i ⁇ -alkanoyloxy in accordance with the invention in each case independently represents all saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms which are bonded via a carboxyyloxy group, in which are preferred. is according to the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms, which are bonded via a Carbo ⁇ yloxy group, in particular for methanoyloxy, Etha ⁇ oyloxy, n-propanoyloxy and i-Propanoyloxy.
  • Alkoxycarbonyl means erfindungsgemafl preferably C ⁇ j -Alkcxvcarbonyl C 1-1 ⁇ -. Erfindu ⁇ gshunt alkoxycarbonyl in each case independently of one another for all saturated and unsaturated, linear and branched alkyl radicals having up to 18 carbon atoms, which has a group Oxycarbo ⁇ yl are attached, wherein Ci »a-Alkoxycarbo ⁇ yl radicals are preferred.
  • C- ⁇ . ⁇ - alkoxycarbonyl for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms which bound via an oxycarbonyl group are, in particular for methoxycarbonyl and ethoxycarbonyl
  • C 1-19 -alkylaminocarbonyl in each case independently of one another represents an aminocarbonyl group which is mono- or disubstituted by a saturated or unsaturated, linear or branched alkyl radical with up to 18 C atoms is substituted, wherein mono- or disubstituted by C ⁇ alkyl groups substituted aminocarbonyl radicals, in particular monomethylaminocarbonyl, Diemethylaminocarbonyl, Monoethylami ⁇ ocarbo ⁇ yl and Diethylami ⁇ ocarbo ⁇ yl, are preferred.
  • alkylsulfanylcarbonyl is preferably d-ie-alkylsulfanylcarbonyl.
  • Ci-m-Alkylsulfanylcarbonyl is according to the invention independently of each other for all saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms, which have a thiocarbony] group are attached, wherein C 1- ⁇ -Alkylsulfanylcarbonyl radicals are preferably C 1-6 -.
  • Alkylsulfanylcarbo ⁇ yl is according to the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms which bound via a group Thiocarbo ⁇ yl are, in particular for methylthiocarbonyl and ethylthiocarbonyl.
  • Alkylamino is erfind ungsgernäß preferably (Ci-ia alkyl) NH. ⁇ Fl CM alkyl) NH erfindungsgsmäß each independently, all saturated and unsaturated, linear and branched alkyl groups having up to 18 carbon atoms, which has a Hydrogenamino group are bonded, wherein (a CI_ alkyl) NH is preferred (Ci. alkyl a) NH according to the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms, which has a Hydrogenamino Group are bound, in particular for CH 3 NH and C 2 H S NH.
  • dialkylamine is preferably di (C 1 -alkyl) N
  • di- (C 1 -isalkyl) N is according to the invention in each case independently of each other all saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms which are bonded via a (C 1-10 -alkylamino group, preference being given to di- (C 1-8 -alkyl) N, where the two alkyl radicals may be identical or different from one another.
  • alkyl) N is according to the invention for all saturated and unsaturated, linear and branched alkyl groups having up to 6 C-atoms, which ami ⁇ o group are bonded via a (Ci- ⁇ - alkyl), especially for (CHj) 2 N and (C 2 H 6 ) 2 N.
  • aryl preferably represents C ⁇ . 1 [r aryl.
  • C 1-10 aryl is according to the invention, in particular also in C 6-10 aryl-C 1-12 -alkyl, C ⁇ -m-aryloxy, Ce.
  • Heteroaryl is erfg ⁇ dungsg ⁇ mäß, in particular also in heteroaryl-CM2-alkyl, heteroaryloxy, heteroarylamino, Heteroarylsulfa ⁇ yl, Heteroarylsulfonyl, Heteroarylsulfoxidyl, H ⁇ teroarylcarbonyl, Heteroarylcarbo ⁇ yloxy, Heteroaryloxycarbonyi, Heteroarylaminocarbo ⁇ yl and H ⁇ teroarylsulfanylcarbonyl, unless otherwise indicated, for at least one heteroatom selected from O, S and N.
  • aromatic radical having 5 to 10, preferably 5 or 6, ring members, preferably selected from furanyl, thienyl, thiophenyl, pyrrolyl, isopyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyi, Benzothiophenyl, indolyl, quinolinyl, isoquinolinyl, benzimidazolyl, indazolyl, pyridofuranyl and pyridothienyl.
  • alkyl radical may be saturated or unsaturated, branched or unbranched.
  • Preferred radicals are benzyl, phenylethyl, naphthylmethyl and naphthylethyl,
  • Amino stands for any substituted or unsubstituted amino group, in particular -NH 2 , -NH (C 1-1B -alkyl), -N (C 1-1 -alkyl) -alkyl, -NH 2 -alkyl-aryl) or -N (C 6-10 -AfyI) 2 , especially preferred for -NH £ .
  • ammonium represents any substituted or unsubstituted ammonium group, in particular -NH 3 W , -NH 2 (C 1 -18 -alkyl) -NH (C 1 -alkyl) 2 W or -N (C 1-18 -AikyI) 3 ",
  • “Sulfato” according to the invention is in particular Wr -OS (O) 2 -OR 1 "sulfo" for -S (O) 2 -OR, “amidosulfo” for -O-S (O) 2 -NR 2 , “phosphato” for 0-P (O) (OR) 2 , “phosphono” for -P (O) (OR) 2 "amidophosphono” for -O-P (O) (NRj) 2 or -OP (O) (OR) (NO 2) and "amidocarbonyl” -C (O) -NR 2 wherein each R is independently (H, M +) F Ci-ie-alkyl, Ce-io-aryl or Ci-is- alkyl-C e- 10 -aryl stands.
  • Imidazolium salts to be used according to the invention are preferably present in the inventive compositions in an amount of from 0.01 to 5.0% by weight, more preferably in an amount of from 0.1 to 3.0% by weight, especially in an amount from 0.2 to 2.0% by weight.
  • a washing or cleaning agent according to the invention and in particular a machine dishwashing detergent according to the invention may contain further washing or cleaning-active ingredients as well as other ingredients customary for detergents and cleaners.
  • Detergents or cleaners according to the invention generally contain one or more builders, in particular zeolites, silicates, carbonates, organic cobuilders and, where there are no ecological reasons against their use, the phosphates.
  • builders in particular zeolites, silicates, carbonates, organic cobuilders and, where there are no ecological reasons against their use, the phosphates.
  • the latter are particularly preferred builders to be used in automatic dishwashing detergents.
  • crystalline layered silicates of general formula NaMSi x O 2x + I ⁇ y H 2 O wherein M is sodium or hydrogen, x is a number from 1, 9 to 22, preferably from 1: 9 to 4, wherein particularly preferred Values for x are 2, 3 or 4, and y is a number from 0 to 33, preferably from 0 to 20.
  • the crystalline layered silicates of the formula NaMSi x O 2x + 1 ⁇ y H 2 O are sold for example by Clariant GmbH (Germany) under the trade name Na-SKS.
  • silicates Na-SKS-1 (Na2 Sb2 ⁇ 4 5 ⁇ x H 2 O, kenyaite), Na-SKS-2 (Na 2 Si 14 O 29 ⁇ x H 2 O, magadiite), Na-SKS 3 (Na 2 Si 8 O 17 .xH 2 O) or Na-SKS-4 (Na 2 Si 4 O 9 .H 2 O, makatite).
  • the agents according to the invention furthermore preferably contain surfactants, in particular selected from nonionic, anionic, cationic and amphoteric surfactants.
  • surfactants used according to the invention are preferably nonionic, anionic and / or amphoteric surfactants.
  • nonionic surfactants it is possible to use all nonionic surfactants known to the person skilled in the art.
  • Suitable nonionic surfactants are, for example, alkyl glycosides of the general formula RO (G) x in which R corresponds to a primary straight-chain or methyl-branched, in particular 2-methyl-branched aliphatic radical having 8 to 22, preferably 12 to 18 carbon atoms and G is the Is a symbol which represents a glycose unit having 5 or 6 C atoms, preferably glucose.
  • the degree of oligomerization x which indicates the distribution of monoglycosides and oligoglycosides, is an arbitrary number between 1 and 10; preferably x is 1, 2 to 1, 4.
  • nonionic surfactants used either as the sole nonionic surfactant or in combination with other nonionic surfactants are alkoxylated, preferably ethoxylated or ethoxylated and propoxylated fatty acid alkyl esters, preferably having from 1 to 4 carbon atoms in the alkyl chain.
  • Nonionic surfactants of the amine oxide type for example N-cocoalkyl-N, N-dimethylamine oxide and N-tallowalkyl-N, N-dihydroxyethylamine oxide, and the fatty acid alkanolamides may also be suitable.
  • the amount of these nonionic surfactants is preferably not more than that of the ethoxylated fatty alcohols, especially not more than half thereof.
  • surfactants are polyhydroxy fatty acid amides of the formula
  • R is an aliphatic acyl radical having 6 to 22 carbon atoms
  • R 1 is hydrogen, an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms
  • [Z] is a linear or branched polyhydroxyalkyl radical having 3 to 10 carbon atoms and 3 to 10 hydroxyl groups.
  • the polyhydroxy fatty acid amides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • the group of polyhydroxy fatty acid amides also includes compounds of the formula
  • R is a linear or branched alkyl or alkenyl radical having 7 to 12 carbon atoms
  • R 1 is a linear, branched or cyclic alkyl radical or an aryl radical having 2 to 8 carbon atoms
  • R 2 is a linear, branched or cyclic alkyl radical or an aryl radical or an oxy-alkyl radical having 1 to 8 carbon atoms
  • Cw-alkyl or phenyl radicals are preferred
  • [Z] is a linear polyhydroxyalkyl radical whose alkyl chain is substituted by at least two hydroxyl groups, or alkoxylated, preferably ethoxylated or propoxylated derivatives of this residue.
  • [Z] is preferably obtained by reductive amination of a reduced sugar, for example glucose, fructose, maltose, lactose, galactose, mannose or xylose.
  • a reduced sugar for example glucose, fructose, maltose, lactose, galactose, mannose or xylose.
  • the N-alkoxy- or N-aryloxy-substituted compounds can be converted into the desired polyhydroxy fatty acid amides by reaction with fatty acid methyl esters in the presence of an alkoxide as catalyst.
  • the detergents according to the invention also contain bleaches in a preferred embodiment. Among the compounds serving as bleaches in water H 2 O 2 , sodium percarbonate, sodium perborate tetrahydrate and sodium perborate monohydrate are of particular importance.
  • Further useful bleaching agents are, for example, peroxopyrophosphates, citrate perhydrates and peroxygenic salts or peracids which yield H 2 O 2 , such as persulfates or persulfuric acid.
  • the urea peroxohydrate percarbamide which can be described by the formula H 2 N-CO-NH 2 H 2 O 2 , is also useful , Especially when using the MiUeI for cleaning hard surfaces, for example with automatic dishwashing !
  • they may also contain bleaches from the group of organic bleaches, although their use is in principle also possible with detergents.
  • Typical organic bleaches are the diacyl peroxides. such as dibenzoyl peroxide.
  • organic bleaching agents are the peroxyacids, examples of which are the alkyl peroxyacids and the aryl peroxyacids.
  • Preferred representatives are (a) peroxybenzoic acid and its substituted derivatives, such as alkylperoxybenzoic acids, but also peroxy- ⁇ -naphthoic acid and magnesium monoperphthalate.
  • aliphatic or substituted aliphatic peroxyacids such as peroxylauric
  • bleaching agent and chlorine or bromine releasing substances can be used.
  • suitable chlorine or bromine-releasing materials are heterocyclic N-bromo and N-chloroamides, for example trichloroisocyanuric acid, tribromoisocyanuric acid B, dibromoisocyanuric acid and / or dichloroisocyanic acid (DICA) and / or their salts with cations such as potassium and sodium.
  • DICA dichloroisocyanic acid
  • Hydantoin compounds such as 1,3-dichloro-5,5-dimethylhydantoin are also suitable.
  • inventive replaceable further ingredients in particular with regard to inventively preferably usable Geruststoffen, surfactants, polymers, bleaching agents, especially Bieicheptatoren and / or bleach catalysts, enzymes, especially amylases, proteases and Amadoriasen, solvents, thickeners, sequestering agents, electrolytes, optical brighteners, grayness inhibitors, Glaskorrosionsi ⁇ hibitore ⁇ , Corrosio ⁇ sinhibitoren, Farbubertragungsinhibitorsen, Schaumi ⁇ hibitore ⁇ , Disintegrationswhisstoffn, abrasives, dyes or dyes, perfumes, perfume carriers, microbial agents, UV absorbents, enzyme stabilizers, "Soil-Release" -W rkstoffen, Acidifiziem ⁇ gsmiitel ⁇ and Propellants and with regard to their preferred ⁇ reference is made to Offenlegii ⁇ gsschnft WO2008 / 101810.
  • a separate subject matter of the invention is a process for the mechanical cleaning of textiles or of hard surfaces, in which at least in one of the process steps an imidazolium salt according to the invention, preferably in combination with salicylic acid or a salicylic acid derivative, is used.
  • Processes for the cleaning of textiles are generally distinguished by the fact that various cleaning-active substances are applied to the items to be cleaned in a plurality of process steps and washed off after the reaction time, or the product to be treated is otherwise treated with a detergent or a solution of this agent.
  • a separate subject of the invention is the use of imidazolium salts according to the invention, preferably in combination with salicylic acid or a salicylic acid derivative, for the purification of textiles or hard surfaces.
  • imidazolium salts and corresponding combinations with salicylic acid and salicylic acid derivatives can, in particular according to the properties described above and the methods described above, be used to remove stains from textiles or hard surfaces. Examples of embodiments include hand washing, manual removal of stains from textiles or hard surfaces, or use in conjunction with a machine process.
  • the imidazolium salts and salicylic acid derivatives according to the invention are in this case provided in the context of one of the above formulations for agents according to the invention, preferably detergents or cleaners.
  • Another object of the present invention is also a product comprising a composition according to the invention or a detergent or cleaning agent according to the invention, in particular a hard surface cleaner according to the invention, and a spray dispenser.
  • a spray dispenser In the case of the product, this can be both a chamber chamber and a multi-chamber container, in particular a two-chamber container.
  • the spray dispenser is preferably a manually activated spray dispenser, in particular selected from the group comprising aerosol sprayers (pressurized gas containers, also called spray cans), pressure-building spray dispensers, pump spray dispensers and trigger spray dispensers, in particular pump spray dispensers and trigger sprayers with a container made of transparent polyethylene or polyethylene terephthalate.
  • Spray dispensers are described in more detail in WO 96/04940 (Procter & Gamble) and the US patents cited therein on spray dispensers, to which reference is made in this regard and the contents of which are hereby incorporated by reference.
  • Triggersprühspender and pump sprayer have over compressed gas tanks the advantage that no propellant must be used.
  • suitable particles-passing attachments, nozzles, etc. so-called “nozzle valves”
  • enzyme in this embodiment can optionally also be added to the composition in a form immobilized on particles and thus metered in as a cleaning foam.
  • Machine dishwashing agents particularly preferred according to the invention comprise
  • surfactant preferably nonionic and / or amphoteric surfactant (s), more preferably nonionic (s) surfactant (s);
  • enzyme preferably selected from amylases, proteases and amadoriases;
  • bleaching agent preferably percarbonate
  • imidazolium salts such as optionally 0.01 to 5 wt .-%, preferably 0.02 to 4 wt .-% and in particular 0.05 to 3 wt .-% salicylic acid and / or salicylic acid derivatives.
  • Very particularly preferred automatic dishwashing detergents comprise
  • nonionic surfactant s
  • wt .-% 0.5 to 8 wt .-%, preferably 1 to 7 wt .-% and in particular 2 to 6 wt .-% enzyme (s) selected from amylases, proteases and amadoriases;
  • Bleach catalysts such as
  • Imidazolium salts and optionally 0.01 to 5 wt .-%, preferably 0.02 to 4 wt .-% and in particular 0.05 to 3 wt .-% salicylic acid and / or salicylic acid derivatives.
  • compositions according to the invention can take place in different ways.
  • the compositions according to the invention can be present in solid or liquid form as well as a combination of solid and liquid forms.
  • Powder, granules, extrudates or compactates, in particular tablets, are particularly suitable as firm supply forms.
  • the liquid supply forms based on water and / or organic solvents may be thickened, in the form of gels.
  • Inventive agents can be formulated in the form of single-phase or multi-phase products.
  • automatic dishwashing detergents with one, two, three or four phases are preferred.
  • Machine dishwashing detergent characterized in that it is in the form of a prefabricated dosing unit with two or more phases, are particularly preferred.
  • the individual phases of multiphase agents may have the same or different states of aggregation.
  • Machine dishwashing detergents which have at least two different solid phases and / or at least two liquid phases and / or at least one solid and at least one solid phase are preferred.
  • Automatic dishwasher detergents according to the invention are preferably prefabricated to form metering units. These metering units preferably comprise the necessary for a cleaning cycle amount of washing or cleaning-active substances. Preferred metering units have a weight between 12 and 30 g, preferably between 14 and 26 g and in particular between 16 and 22 g.
  • the volume of the aforementioned metering units and their spatial form are selected with particular preference so that a metering of the prefabricated units is ensured via the metering chamber of a dishwasher.
  • the volume of the dosing unit is therefore preferably between 10 and 35 ml, preferably between 12 and 30 ml and in particular between 15 and 25 ml.
  • the automatic dishwasher detergents according to the invention in particular the prefabricated metering units, have a water-soluble coating, with particular preference.
  • bromoacetophenone or chloroacetophenone are abs. In 60 ml. Under N 2 is heated to about 70 0 C and 0.06 mol of imidazole derivative in 15 ml of abs. Ethyl acetate was added dropwise.
  • test soil is obtained by baking a mixture of cream, whole egg and cornstarch on a glazed ceramic surface. This test dirt is then rinsed with a dishwasher G 698 SC Plus from sensor. Miele in Intensiv Strukturprogramm (50 0 C, 107 minutes). The amount of soil removed is determined gravimetrically and the result is expressed in percent based on the improvement in the washing result compared to a commercial reference dishwashing detergent.

Abstract

The present invention relates to detergents and cleaning products containing imidazolium salts and to the use of said detergents and cleaning products for cleaning textiles and surfaces.

Description

20.02.2009 20/02/2009
11
Verwendung von Imidazolium-Salzen in Wasch- und ReinigungsmittelnUse of imidazolium salts in detergents and cleaners
Die vorliegende Erfindung betrifft Wasch- und Reinigungsmittel enthaltend Imidazolium-Salze sowie die Verwendung dieser Wasch- und Reinigungsmittel zur Reinigung von Textilien und Oberflächen.The present invention relates to detergents and cleaning agents containing imidazolium salts and to the use of these detergents and cleaners for cleaning textiles and surfaces.
In Wasch- und Reinigungsmitteln wurde bereits eine Vielzahl von Wirksubstanzen eingesetzt, um deren Reinigungsleistung zu verbessern. Dennoch besteht insbesondere in Bezug auf besonders hartnäckige Anschmutzungen immer noch ein Bedarf an Mitteln mit verbesserter Wirksamkeit. Ein besonderes Problem stellt hierbei stark eingebrannter Schmutz dar, der in der Regel nach wie vor nur sehr mühsam und mit großem Zeitaufwand, wie etwa durch mehrstündiges Einweichen, entfernt werden kann.In washing and cleaning agents, a variety of active substances has already been used to improve their cleaning performance. Nevertheless, there is still a need for more effective agents, especially with regard to particularly stubborn stains. A particular problem in this case is strongly burned in dirt, which can be as a rule only with great difficulty and with great expenditure of time, such as by soaking for several hours, removed.
Überraschenderweise wurde nun herausgefunden, dass Imidazolium-Salze, insbesondere in Bezug auf stark eingebrannten Schmutz, eine deutliche Verbesserung der Reinigungsleistung von Wasch- und Reinigungsmitteln ermöglichen.Surprisingly, it has now been found that imidazolium salts, in particular with respect to strongly baked-on dirt, allow a significant improvement in the cleaning performance of detergents and cleaners.
Ein erster Gegenstand der vorliegenden Erfindung sind daher Wasch- und Reinigungsmittel enthaltend mindestens ein Imidazolium-Salz. Besonders bevorzugt sind hierbei Reinigungsmittel für harte Oberflächen, insbesondere Handgeschirrspülmittel und maschinelle Geschirrspülmittel.A first subject of the present invention are therefore detergents and cleaners containing at least one imidazolium salt. Cleaning agents for hard surfaces, in particular hand dishwashing detergents and automatic dishwasher detergents, are particularly preferred.
Ein weiterer Gegenstand der vorliegenden Erfindung ist daher ebenso die Verwendung von solchen erfindungsgemäßen Imidazolium-Salzen sowie von Wasch- und Reinigungsmitteln, die solche Imidazolium-Salze enthalten, zur Reinigung von Oberflächen, insbesondere harten Oberflächen, sowie zur Reinigung textiler Flächengebilde.Another object of the present invention is therefore also the use of such imidazolium salts according to the invention and of detergents and cleaners containing such imidazolium salts, for the cleaning of surfaces, especially hard surfaces, as well as for the cleaning of textile fabrics.
Ein bevorzugter Gegenstand der vorliegenden Erfindung ist hierbei insbesondere die Verwendung von solchen erfindungsgemäßen Imidazolium-Salzen sowie von Wasch- und Reinigungsmitteln, die solche Imidazolium-Salze enthalten, zur Entfernung von hartnäckigen und/oder eingebrannten, insbesondere stark eingebrannten, Anschmutzungen.A preferred object of the present invention is in particular the use of such imidazolium salts according to the invention and of detergents and cleaners which contain such imidazolium salts, for the removal of stubborn and / or baked-on, in particular strongly burned, stains.
Ein weiterer bevorzugter Gegenstand der vorliegenden Anmeldung ist weiterhin ein Verfahren zur Reinigung von Geschirr in einer Geschirrspülmaschine, bei welchem ein erfindungsgemäßes Wasch- oder Reinigungsmittel während des Durchlaufens eines Geschirrspülprogramms vor Beginn des Hauptspülgangs oder im Verlaufe des Hauptspülgangs in den Innenraum einer Geschirrspülmaschine eindosiert wird. Die Eindosierung bzw. der Eintrag des erfindungsgemäßen Mittels in den Innenraum der Geschirrspülmaschine kann manuell erfolgen, vorzugsweise wird das Mittel jedoch mittels der Dosierkammer in den Innenraum der Geschirrspülmaschine dosiert. Bei dem erfindungsgemäßen Imidazolium-Salz handelt es sich vorzugsweise um ein Salz, das als Imidazolium-Kation eine Verbindung der allgemeinen Formel (I) enthältA further preferred subject matter of the present application is furthermore a process for cleaning dishes in a dishwasher, in which a washing or cleaning agent according to the invention is metered into the interior of a dishwasher during the passage of a dishwashing program before the main wash cycle or during the main wash cycle. The metering or the entry of the agent according to the invention into the interior of the dishwasher can be done manually, but preferably the agent is metered by means of the metering chamber into the interior of the dishwasher. The imidazolium salt according to the invention is preferably a salt which contains as imidazolium cation a compound of general formula (I)
Figure imgf000003_0001
Figure imgf000003_0001
dadurch gekennzeichnet, dass R1 , R2, R3, R4 und R5 unabhängig voneinander für Trifluormethyl, Wasserstoff, Alkyl, Cycloalkyl, Cycloalkylalkyl, Alkenyl, Alkinyl, Heteroalkyl, Heterocycloalkyl, Alkoxy, Alkoxyalkyl, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Alkanoyl, Alkanoyloxy, Alkoxycarbonyl, Alkylaminocarbonyl, Alkylsulfanylcarbonyl, Hydroxy, Hydroxyalkyl, Hydroxycarbonyl, Amino, Alkylamino, Aryl, Arylalkyl, Aryloxy, Arylamino, Arylsulfanyl, Arylsulfinyl, Arylsulfonyl, Arylcarbonyl, Arylcarbonyloxy, Aryloxycarbonyl, Arylaminocarbonyl, Arylsulfanylcarbonyl, Heteroaryl, Heteroarylalkyl, Heteroaryloxy, Heteroarylamino, Heteroarylsulfanyl, Heteroarylsulfonyl, Heteroarylsulfoxidyl, Heteroarylcarbonyl, Heteroarylcarbonyloxy, Heteroaryloxycarbonyl, Heteroarylaminocarbonyl, Heteroarylsulfanylcarbonyl, Alkoxysulfonyl, Alkoxycarbinol, Sulfo, Sulfino, Sulfeno, Formyl oder Thioformyl stehen, wobei alle Reste des sich so ergebenden Moleküls jeweils unabhängig voneinander gegebenenfalls auch ein- oder mehrfach substituiert sein können.characterized in that R1, R2, R3, R4 and R5 independently of one another represent trifluoromethyl, hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, heteroalkyl, heterocycloalkyl, alkoxy, alkoxyalkyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkanoyl, alkanoyloxy, alkoxycarbonyl, Alkylaminocarbonyl, alkylsulfanylcarbonyl, hydroxy, hydroxyalkyl, hydroxycarbonyl, amino, alkylamino, aryl, arylalkyl, aryloxy, arylamino, arylsulfanyl, arylsulfinyl, arylsulfonyl, arylcarbonyl, arylcarbonyloxy, aryloxycarbonyl, arylaminocarbonyl, arylsulfanylcarbonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylamino, heteroarylsulfanyl, heteroarylsulfonyl, Heteroarylsulfoxidyl, heteroarylcarbonyl, heteroarylcarbonyloxy, heteroaryloxycarbonyl, heteroarylaminocarbonyl, heteroarylsulfanylcarbonyl, alkoxysulfonyl, alkoxycarbinol, sulfo, sulfino, sulfeno, formyl or thioformyl, all radicals of the resulting molecule in each case independently of one another optionally also auc h may be monosubstituted or polysubstituted.
In einer bevorzugten Ausführungsform stehen R1 und R4 unabhängig voneinander für gegebenenfalls substituiertes Alkyl, Aryl, Arylalkyl, Alkylcarbonylalkyl oder Arylcarbonylalkyl und R2, R4 und R5 unabhängig voneinander für Wasserstoff oder gegebenenfalls substituiertes Alkyl.In a preferred embodiment, R 1 and R 4 are independently optionally substituted alkyl, aryl, arylalkyl, alkylcarbonylalkyl or arylcarbonylalkyl, and R 2, R 4 and R 5 are independently hydrogen or optionally substituted alkyl.
In einer weiteren bevorzugten Ausführungsform umfassen hierbei R1 und/oder R4, vorzugsweise sowohl R1 als auch R4 einen aromatischen Rest.In a further preferred embodiment, in this case R1 and / or R4, preferably both R1 and R4, comprise an aromatic radical.
In einer besonders bevorzugten Ausführungsform stehen R1 und R4 unabhängig voneinander für gegebenenfalls substituiertes Phenyl, Phenyl-Ci-e-alkyl oder Phenylcarbonyl-Ci-e-alkyl und dieIn a particularly preferred embodiment, R 1 and R 4 independently of one another are optionally substituted phenyl, phenyl-C 1-e-alkyl or phenylcarbonyl-C 1-e-alkyl and
Reste R2, R4 und R5 unabhängig voneinander für Wasserstoff oder gegebenenfalls substituiertesRadicals R2, R4 and R5 are independently hydrogen or optionally substituted
C^-Alkyl.C ^ alkyl.
In ganz besonders bevorzugten Ausführungsformen steht R1 für einen gegebenenfalls substituierten Phenacyl-Rest und/oder R4 für einen gegebenenfalls substituierten Phenylmethyl-In very particularly preferred embodiments, R 1 is an optionally substituted phenacyl radical and / or R 4 is an optionally substituted phenylmethyl radical
Rest. In diesem Sinne handelt es sich bei dem Imidazohum-Kation in einer ganz besonders bevorzugten Ausführungsform um eine Verbindung gemäß Formel (N) oder Formel (IM)Rest. In this sense, in a very particularly preferred embodiment, the imidazohum cation is a compound according to formula (II) or formula (III)
Figure imgf000004_0001
wobei die genannten Verbindungen gegebenenfalls auch ein- oder mehrfach substituiert sein können.
Figure imgf000004_0001
where appropriate, said compounds may also be monosubstituted or polysubstituted.
Die zuvor genannten Substituenten sind vorzugsweise ausgewählt aus Alkyl, Halogen, insbesondere Chlor, Brom, lod oder Fluor, Hycfroxy, Hydroxyalkyl, Hydroxycarbonyl, Alkoxy, Alkoxyalkyl, Alkoxycarbonyl, Amino, Alkylamino und Dialkylamino.The abovementioned substituents are preferably selected from alkyl, halogen, in particular chlorine, bromine, iodine or fluorine, hydroxypropyl, hydroxyalkyl, hydroxycarbonyl, alkoxy, alkoxyalkyl, alkoxycarbonyl, amino, alkylamino and dialkylamino.
Das Anioπ des Imidazolium-Salzes ist vorzugsweise ausgewählt aus Halogeπid, insbesondere Chlorid, Bormid, lodid oder Fluorid. Sulfat, Sulfit, Nitrat, Hydrogβncarbonat und deprotoniertβn organischen Säuren, besonders bevorzugt handelt es sich um ein Halogenid, vor allem Bromid.The Anioπ of the imidazolium salt is preferably selected from Halogeπid, in particular chloride, boron, iodide or fluoride. Sulfate, sulfite, nitrate, Hydrogβncarbonat and deprotonatedβn organic acids, more preferably it is a halide, especially bromide.
Es hat sich erfindungsgemäß überraschenderweise herausgestellt, dass die Waschleistung noch weiter verbessert werden kann, wenn das Imidazolium-Salz in Kombination mit Salicylsäure (2- Hydroxy-Benzoesaure), einem SalicylsäurβOeπvat oder Mischungen davon eingesetzt wird.It has surprisingly been found according to the invention that the washing performance can be further improved if the imidazolium salt is used in combination with salicylic acid (2-hydroxybenzoic acid), a salicylic acid or mixtures thereof.
Die Salicylsäure-Derivate können erfindungsgemäß insbesondere ausgewählt sein aus 2- Hydroxybenzoesäure, die durch weitere Reste am Ring substituiert ist, wobei die weiteren Reste vorzugsweise ausgewählt sind aus Hydroxy, Amino, Halogen, insbesondere Chlor, Brom oder Fluor, Ci-B-Alkyl, Ci-β-Alkoxy, Cf-β-Alkylamino und Di-(Ci-B-Alkyl)amino. Die Ca rboxyl- Gruppe und die Hydroxy-Gruppe der 2-Hydroxybenzoesäυre und der Salicylsäure-Derivate können weiterhin gegebenenfalls auch verestert bzw. verethert sein, insbesondere durch gegebenenfalls substituiertes Ci-β-Alkaπol.According to the invention, the salicylic acid derivatives may be selected, in particular, from 2-hydroxybenzoic acid which is substituted by further radicals on the ring, the other radicals preferably being selected from hydroxyl, amino, halogen, in particular chlorine, bromine or fluorine, C 1 -b-alkyl, Ci-β-alkoxy, Cf-β-alkylamino and di (Ci-B-alkyl) amino. The Ca rboxyl group and the hydroxy group of 2-Hydroxybenzoesäυre and salicylic acid derivatives may also be optionally esterified or etherified, in particular by optionally substituted Ci-β-Alkaπol.
„Alkyl" steht erfindungsgemäß vorzugsweise für C
Figure imgf000004_0002
^.ie-Alkyl. steht erfindungsgemäß jeweils unabhängig voneinander für alle gesättigten linearen und verzweigten Alkyl-Reste mit bis zu 18 C-Atomen, wobei Ci,β-Alkyl-Reste bevorzugt sind. Ci„6-Alkyl steht erfindungsgemäß für alle gesättigten linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomθn, iπsbθsondθre für Methyl, Ethyl, n-Propyl, i-Propyl, n-Butyl, i-Butyl, t-Bυtyl sowie alle Isomere des Pentyl und des Hexyl."Alkyl" according to the invention preferably represents C
Figure imgf000004_0002
^. ie -alkyl. in accordance with the invention in each case independently of one another for all saturated linear and branched alkyl radicals having up to 18 C atoms, preference being given to C 1, B-alkyl radicals. Ci "6-alkyl is according to the invention for all saturated linear and branched alkyl radicals having up to 6 C-Atomθn, iπsbθsondθre for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl and all isomers of pentyl and hexyl.
„Cycloalkyl" steht erfind uπgsgemäfl vorzugsweise für Cs-β-Cycloalkyl. Cj-β-Cycloalkyl steht erfindungsgemäß jeweils unabhängig voneinander für alle cyclischen Alkyl-Reste mit 3 bis 6 C- Atomen, vorzugsweise mit 5 bis 6 C-Atomen, wobei die Reste gesättigt oder ungesättigt sein können, insbesondere für Cyclopentyl, Cyclohexyl oder Cyclopentadienyl.According to the invention, "cycloalkyl" is preferably Cs-β-cycloalkyl. Cj-β-Cycloalkyl independently of one another in each case denotes all cyclic alkyl radicals having 3 to 6 C atoms, preferably 5 to 6 C atoms, where the radicals may be saturated or unsaturated, especially for cyclopentyl, cyclohexyl or cyclopentadienyl.
„Alkenyl" steht erfindungsgemöß vorzugsweise für C2-ia-Alkenyl. C2-ifl-Alkenyl steht erfiπduπgsgemad jeweils unabhängig voneinander für alle linearen und verzweigten Alkyl-Reste mit bis zu 18 C-Atomen, die mindestens eine Doppelbindung enthalten, wobei C2-6-Alkenyl- Reste bevorzugt sind. C2-6-Alkenyl steht erfmduπgsgemaß für alle linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomen, die mindestens eine Doppelbindung enthalten, insbesondere für Ethenyl, Propenyl, i-Propenyl sowie alle Isomere des Butenyl, Pentenyl und Hexenyl."Alkenyl" is C 2 -i erfindungsgemöß preferably a alkenyl. C 2 -i fl -alkenyl erfiπduπgsgemad each independently for all linear and branched alkyl radicals having up to 18 carbon atoms, containing at least one double bond, C 2-6 alkenyl radicals are preferably C 2 -. 6 -alkenyl erfmduπgsgemaß for all linear and branched alkyl radicals having up to 6 carbon atoms, containing at least one double bond, in particular ethenyl, propenyl, i-propenyl and all isomers of butenyl, pentenyl and hexenyl.
„Alkinyl" steht θrfiπduπgsgemäß vorzugsweise für
Figure imgf000005_0001
steht erfindungsgemäß jeweils unabhängig voneinander für alle linearen und uπverzweigteπ Alkyl-Reste mit bis zu 18 C- Atomen, die mindestens eine Dreifachbindung enthalten, wobei C2.e-Alkinyl-Reste bevorzugt sind. C2.6-Alkinyl steht erfinduπgsgemälϊ für alle linearen und unverzweigten Alkyl-Reste mit bis zu 6 C- Atomen, die mindestens eine Dreifachbindung enthalten, insbesondere für Ethinyl, Propinyl, i- Propiπyl sowie alle Isomere des Butrnyl, Peπtinyl und Hexinyl."Alkynyl" is preferably θrfiπduπgsgemäß for
Figure imgf000005_0001
in accordance with the invention, in each case independently of one another, denotes all linear and branched alkyl radicals having up to 18 C atoms which contain at least one triple bond, where C 2 . e- alkynyl radicals are preferred. C 2 . 6 -Alkinyl stands erfinduπgsgemälϊ for all linear and unbranched alkyl radicals having up to 6 carbon atoms which contain at least one triple bond, in particular ethynyl, propynyl, i-Propiπyl and all isomers of Butrnyl, Peπtinyl and hexynyl.
Heteroalkyl steht erfindungsgemäß jeweils unabhängig voneinander für alle gesättigten und ein- oder mehrfach ungesättigten, linearen oder verzweigten Alkyl-Reste, die mindestens ein, bevorzugt genau ein Heteroatom, insbesondere ausgewählt aus O, S und N, enthalten, wobei die Summe aus C- Und Hetero-Atomeπ bevorzugt bis zu 18, besonders bevorzugt bis zu 6, betragt.Heteroalkyl according to the invention is in each case independently of one another for all saturated and mono- or polyunsaturated, linear or branched alkyl radicals which contain at least one, preferably exactly one heteroatom, in particular selected from O, S and N, where the sum of C and Hetero-Atomeπ preferably up to 18, more preferably up to 6 amounts.
Heterocycloalkyl steht erfindungsgemäß jeweils unabhängig voneinander für alle cyclischen Alkyl- Reste, die mindestens ein, bevorzugt genau ein, Heteroatom, insbesondere ausgewählt aus O, S oder N1 enthalten, wobei der Ring vorzugsweise drei- bis achtgliederig, besonders bevorzugt fünf- bis sechsgliedrig ist. Beispiele hierfür sind Tetrahydrofuranyl, Tetrahydrothiophenyl, Pyrrolidinyl, 2- Thiazolinyl, Tetrahydrothiazolyl, Tetrahydrooxazolyl, Piperidiπyl, Pipβrazinyl, Morpholinyl und Thiomorpholmyl.Heterocycloalkyl according to the invention is in each case independently of one another for all cyclic alkyl radicals which contain at least one, preferably exactly one, heteroatom, in particular selected from O, S or N 1 , wherein the ring is preferably from three to eight membered, more preferably five to six membered , Examples of these are tetrahydrofuranyl, tetrahydrothiophenyl, pyrrolidinyl, 2-thiazolinyl, tetrahydrothiazolyl, tetrahydrooxazolyl, piperidinyl, pipazrazinyl, morpholinyl and thiomorpholmyl.
„Alkoxy" steht erfinduhgsgemäß vorzugsweise für C1-16-AIkOXy. C1-18-AIkOXy steht erfmdungsgemäß jeweils unabhängig voneinander für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 18 C-Atomen, die über ein Sauerstoff-Atom gebunden sind, wobei C1^- Alkoxy-Reste bevorzugt sind. C1-6-AIkOXy steht erfinduπgsgemäß jeweils unabhängig voneinander für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomeπ, die über ein Sauerstoff-Atom gebunden sind, insbesondere für Methoxy und Ethoxy.According to the invention, C 1-18 -alkoxy is preferably independently of each other all saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms which are bonded via an oxygen atom to C 1-16 -alkoxy. When C 1 -C alkoxy radicals are preferred, C 1-6 -alkoxy, according to the invention, in each case independently of one another for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 C atoms, which are bonded via an oxygen atom, in particular methoxy and ethoxy.
„Alkylöulfanyl" steht erfinduπgsgemaß vorzugsweise für Ci_ig-Alkylsulfanyl. Ci-ie-Alkylsulfanyl steht erfinduπgsgemäß jeweils unabhängig voneinander für alle gesättigten und ungesättigten! linearen und verzweigten Alkyl-Reste mit bis zu 18 C-Atomen, die über ein Schwefel-Atom gebunden sind, wobei C1.β-Alkylsulfaπyl-Reste bevorzugt sind. Ci-e-Alkylsulfanyl steht erfindungsgemäß für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomen, die über ein Schwefel-Atom gebunden sind, insbesondere für Methysulfanyl und Ethylsulfaπyl."Alkylöulfanyl" stands erfinduπgsgemaß preferably Ci_ig alkylsulfanyl. Ci-ie-alkylsulfanyl is erfinduπgsgemäß each independently, all saturated and unsaturated! Linear and branched alkyl radicals having up to 18 carbon atoms bonded via a sulfur atom, where C 1, β -alkylsulfinyl radicals are preferred According to the invention, C 1 -alkylsulfanyl represents all saturated and unsaturated, linear and branched alkyl radicals having up to 6 C atoms which are bonded via a sulfur atom, in particular Methysulfanyl and Ethylsulfaπyl.
„Alkylsulfinyl" steht erfindungsgemäß vorzugsweise für C1-ia-Alky[sulfinyl. C^g-Alkylsulfiπyl steht erfindungsgemäß jeweils unabhängig voneinander Für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 16 C-Atomen, die über eine SO-Gruppe gebunden sind, wobei Ci_6-Alkylsulfoπyl-Reste bevorzugt sind. C^-Alkylsulfinyl steht erfindungsgemäß für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomeπ, die über eine SO-Gruppe gebunden sind, insbesondere Für Mβthylsulfiπyl und Ethylsulfinyl.According to the invention, "alkylsulfinyl" is preferably C 1- al-alkynyl [sulfinyl. C 1-6 -alkylsulfinyl according to the invention is, independently of one another, for all saturated and unsaturated, linear and branched alkyl radicals having up to 16 carbon atoms which have an SO group are bonded, said CI_ 6 -Alkylsulfoπyl radicals are preferred. C ^ alkylsulfinyl stands according to the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 C-Atomeπ, which are bonded via an SO group, in particular for Mβthylsulfiπyl and ethylsulfinyl.
„Alkylsulfonyl" steht erfindungsgemäß vorzugsweise für C^a-Alkylsulfonyl, C^a-Alkylsulfonyl steht erfindungsgemäß jeweils unabhängig voneinander für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 18 C-Atomen, die über eine SOjj-Gruppe gebunden sind, wobei Ct-β-Alkylsulfoxidyl-Reste bevorzugt sind. C,.6-AlkylsulFoπyl steht erfinduπgsgemäß für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomen, die über eine SO2-Gruppe gebunden sind, insbesondere für Methylsulfonyl und EthylsulfonylAccording to the invention, "alkylsulfonyl" is preferably C 1 -C 4 -alkylsulfonyl. C 1 -C 4 -alkylsulfonyl according to the invention in each case independently of one another for all saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms which are bonded via a SOjj group are, where C t -β-Alkylsulfoxidyl radicals are preferred. C ,. 6 -AlkylsulFoπyl is erfinduπgsgemäß for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms which bound via a SO 2 group in particular for methylsulfonyl and ethylsulfonyl
„Alkanoyl" steht erfindungsgemäß vorzugsweise für C1-1β-Alkanoyl. C|_1s-Alkanoyl steht erfindungsgemäß jeweils unabhängig voneinander für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 18 C-Atomen, die Über eine Carbonyl-Gruppe gebunden sind, wobei Ci.6-Alkanoyl-Reste bevorzugt sind. Ci-β-Alkanoyl steht erfindungsgemäß für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomen, die über eine Carbonyl-Gruppe gebunden sind, insbesondere Für Methycarboπyl und Ethylcarbonyl.According to the invention, C 1 -alkyl is in each case independently of each other saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms which, via a carbonyl radical, represent C 1-1 -alkanoyl. Ci- 6 -alkanoyl is according to the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms, which are bonded via a carbonyl group , in particular For Methycarboπyl and ethylcarbonyl.
„Alkaπoyloxy" steht erfindungsgemäß vorzugsweise für Ci_is-Alkanoyloxy. Ci-iβ-Alkanoyloxy steht erfindungsgemäß jeweils unabhängig voneinander für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 18 C-Atomen, die über eine Carboπyloxy-Gruppe gebunden sind, wobei
Figure imgf000006_0001
bevorzugt sind.
Figure imgf000006_0002
steht erfindungsgemäß für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomen, die über eine Carboπyloxy-Gruppe gebunden sind, insbesondere für Methanoyloxy, Ethaπoyloxy, n-Propanoyloxy und i-Propanoyloxy. „Alkoxycarbonyl" steht erfindungsgemafl vorzugsweise für C^j-Alkcxvcarbonyl. C1-1β- Alkoxycarbonyl steht erfinduπgsgemäß jeweils unabhängig voneinander für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 18 C-Atomen, die über eine Oxycarboπyl-Gruppe gebunden sind, wobei Ci»a-Alkoxycarboπyl-Reste bevorzugt sind. C-\.§- Alkoxycarbonyl steht erfindungsgemäß für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomen, die über eine Oxycarbonyl-Gruppe gebunden sind, insbesondere für Methoxycarbonyl und EthoxycarbonylAccording to the invention, "alkaπoyloxy" is preferably Ci_is-alkanoyloxy. Ci-iβ-alkanoyloxy in accordance with the invention in each case independently represents all saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms which are bonded via a carboxyyloxy group, in which
Figure imgf000006_0001
are preferred.
Figure imgf000006_0002
is according to the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms, which are bonded via a Carboπyloxy group, in particular for methanoyloxy, Ethaπoyloxy, n-propanoyloxy and i-Propanoyloxy. "Alkoxycarbonyl" means erfindungsgemafl preferably C ^ j -Alkcxvcarbonyl C 1-1β -. Erfinduπgsgemäß alkoxycarbonyl in each case independently of one another for all saturated and unsaturated, linear and branched alkyl radicals having up to 18 carbon atoms, which has a group Oxycarboπyl are attached, wherein Ci »a-Alkoxycarboπyl radicals are preferred. C- \ .§- alkoxycarbonyl accordance with the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms which bound via an oxycarbonyl group are, in particular for methoxycarbonyl and ethoxycarbonyl
„Alkylaminocarbonyl" steht erfindungsgemäß vorzugsweise für C^^-Aikylamiπocarboπyl. C1-19- Alkylaminocarbonyl steht erfindungsgemäß jeweils unabhängig voneinander für eine Aminocarbonyl- Gruppe, die ein- oder zweifach durch einen gesättigten oder ungesättigten, linearen oder verzweigten Alkyl-Rest mit bis zu 18 C-Atomen substituiert ist, wobei ein- oder zweifach durch C^-Alkyl-Gruppen substituierte Aminocarbonyl- Reste, insbesondere Monomethylaminocarbonyl, Diemethylaminocarbonyl, Monoethylamiπocarboπyl und Diethylamiπocarboπyl, bevorzugt sind.According to the invention, C 1-19 -alkylaminocarbonyl in each case independently of one another represents an aminocarbonyl group which is mono- or disubstituted by a saturated or unsaturated, linear or branched alkyl radical with up to 18 C atoms is substituted, wherein mono- or disubstituted by C ^ alkyl groups substituted aminocarbonyl radicals, in particular monomethylaminocarbonyl, Diemethylaminocarbonyl, Monoethylamiπocarboπyl and Diethylamiπocarboπyl, are preferred.
„Atkylsulfanylcarbonyl" steht erfindungsgemäß vorzugsweise für d-ie-Alkylsulfanylcarbonyl. Ci-m- Alkylsulfanylcarbonyl steht erfinduπgsgemäß jeweils unabhängig voneinander für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 18 C-Atomen, die über eine Thiocarboπy] -Gruppe gebunden sind, wobei C1-β-Alkylsulfanylcarbonyl-Reste bevorzugt sind. C1-6- Alkylsulfanylcarboπyl steht erfindungsgemäß für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomen, die über eine Thiocarboπyl-Gruppe gebunden sind, insbesondere für Methylthiocarbonyl und Ethylthiocarbonyl.According to the invention, "alkylsulfanylcarbonyl" is preferably d-ie-alkylsulfanylcarbonyl. Ci-m-Alkylsulfanylcarbonyl is according to the invention independently of each other for all saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms, which have a thiocarbony] group are attached, wherein C 1-β -Alkylsulfanylcarbonyl radicals are preferably C 1-6 -. Alkylsulfanylcarboπyl is according to the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms which bound via a group Thiocarboπyl are, in particular for methylthiocarbonyl and ethylthiocarbonyl.
„Alkylamino" steht erfind ungsgernäß vorzugsweise für (Ci-ia-Alkyl)NH. {C-Mfl-Alkyl)NH steht erfindungsgsmäß jeweils unabhängig voneinander für alle gesättigten und ungesättigten, linearen und verzweigten Alkylreste mit bis zu 18 C-Atomen, die über eine Hydrogenamino-Gruppe gebunden sind, wobei (Ci_a-Alkyl)NH bevorzugt ist (Ci.a-Alkyl)NH steht erfindungsgemäß für alle gesättigten und ungesättigten, linearen und verzweigten Alkyl-Reste mit bis zu 6 C-Atomen, die über eine Hydrogenamino-Gruppe gebunden sind, insbesondere für CH3NH und C2HSNH."Alkylamino" is erfind ungsgernäß preferably (Ci-ia alkyl) NH. {Fl CM alkyl) NH erfindungsgsmäß each independently, all saturated and unsaturated, linear and branched alkyl groups having up to 18 carbon atoms, which has a Hydrogenamino group are bonded, wherein (a CI_ alkyl) NH is preferred (Ci. alkyl a) NH according to the invention for all saturated and unsaturated, linear and branched alkyl radicals having up to 6 carbon atoms, which has a Hydrogenamino Group are bound, in particular for CH 3 NH and C 2 H S NH.
„Dialkylamiπo" steht erfindungsgemäß vorzugsweise für Di-(C1-Ia-AIKyI)N. Di-(C1-iβ-Alkyl)N steht erfindungsgemäli jeweils unabhängig voneinander für alle gesättigten und ungesättigten, linearen und verzweigten Alkylreste mit bis zu 18 C-Atomeπ, die über eine (C^^-Alkyljamino-Gruppe gebunden sind, wobei Di-(Ci.e-Alkyl)N bevorzugt ist. Die beiden Alkyl-Reste können hierbei gleich oder unterschiedlich voneinander sein. Di-(Ci_β-Alkyl)N steht erfindungsgemäß für alle gesättigten und ungesättigten, linearen und verzweigten Alkylreste mit bis zu 6 C-Atomen, die über eine (Ci-β- Alkyl)amiπo-Gruppe gebunden sind, insbesondere für (CHj)2N und (C2H6)2N. Aryl sieht erfindungsgemäß vorzugsweise für Cβ.1[rAryl. C^^-Aryl steht erfindungsgemäß, insbesondere auch in C6-10-Aryl-C1-12-alkyl, Cβ-m-Aryloxy, Ce.10-Arylamino, Ca-10-Arylβulfanyl, CM0- Arylsulfonyl, C6-io-Arylsulfoxidyl, Ce-io-Arylcarbonyl, C&io-Arylcarbonyloxy, C&io-Aryloxycarbonyl, Cβ-io-Arylamiπocarbonyl und
Figure imgf000008_0001
vorzugsweise für Phenyl oder Naphthyl, besonders bevorzugt für Phenyl.According to the invention, "dialkylamine" is preferably di (C 1 -alkyl) N, di- (C 1 -isalkyl) N is according to the invention in each case independently of each other all saturated and unsaturated, linear and branched alkyl radicals having up to 18 C atoms which are bonded via a (C 1-10 -alkylamino group, preference being given to di- (C 1-8 -alkyl) N, where the two alkyl radicals may be identical or different from one another. alkyl) N is according to the invention for all saturated and unsaturated, linear and branched alkyl groups having up to 6 C-atoms, which amiπo group are bonded via a (Ci-β- alkyl), especially for (CHj) 2 N and (C 2 H 6 ) 2 N. According to the invention, aryl preferably represents C β . 1 [r aryl. C 1-10 aryl is according to the invention, in particular also in C 6-10 aryl-C 1-12 -alkyl, Cβ-m-aryloxy, Ce. 10 arylamino, C a-10 -Arylβulfanyl, C M0 - arylsulfonyl, C 6- io-Arylsulfoxidyl, Ce-io-arylcarbonyl, C-io arylcarbonyloxy, C-io aryloxycarbonyl, Cβ-io-Arylamiπocarbonyl and
Figure imgf000008_0001
preferably phenyl or naphthyl, particularly preferably phenyl.
Heteroaryl steht erfiπdungsgβmäß, insbesondere auch in Heteroaryl-CM2-alkyl, Heteroaryloxy, Heteroarylamino, Heteroarylsulfaπyl, Heteroarylsulfonyl, Heteroarylsulfoxidyl, Hθteroarylcarbonyl, Heteroarylcarboπyloxy, Heteroaryloxycarbonyi, Heteroarylaminocarboπyl und Hθteroarylsulfanylcarbonyl, sofern nicht anders angegeben, für einen mindestens ein Heteroatom ausgewählt aus O, S und N enthaltenden aromatischen Rest mit 5 bis 10, vorzugsweise 5 oder 6, Ringgliedern, vorzugsweise ausgewählt aus Furanyl, Thienyl, Thiopheπyl, Pyrrolyl, Isopyrrolyl, Pyrazolyl, Imidazolyl, Oxazolyl, Thiazolyl, Isothiazolyl, Pyridinyl, Pyridazinyl, Pyrimidinyl, Pyraziπyl, Triazinyl, Benzofuranyi, Benzothiophenyl, Indolyl, Chinolinyl, Isochinolinyl, Benzimidazolyl, Indazolyl, Pyridofuranyl und Pyridothienyl.Heteroaryl is erfgπdungsgβmäß, in particular also in heteroaryl-CM2-alkyl, heteroaryloxy, heteroarylamino, Heteroarylsulfaπyl, Heteroarylsulfonyl, Heteroarylsulfoxidyl, Hθteroarylcarbonyl, Heteroarylcarboπyloxy, Heteroaryloxycarbonyi, Heteroarylaminocarboπyl and Hθteroarylsulfanylcarbonyl, unless otherwise indicated, for at least one heteroatom selected from O, S and N. containing aromatic radical having 5 to 10, preferably 5 or 6, ring members, preferably selected from furanyl, thienyl, thiophenyl, pyrrolyl, isopyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyi, Benzothiophenyl, indolyl, quinolinyl, isoquinolinyl, benzimidazolyl, indazolyl, pyridofuranyl and pyridothienyl.
In Arylalkyl, insbesondere C0-10-ArYl-C1-1S- alkyl, und Heteroarylalkyl kann der Alkyl-Rest gesättigt oder ungesättigt, verzweigt oder unverzweigt sein. Bevorzugte Reste sind Benzy], Phenylethyl, Naphthylmethyl und Naphthylethyl,In arylalkyl, in particular C 0-10 -aryl-C 1-1S -alkyl, and heteroarylalkyl, the alkyl radical may be saturated or unsaturated, branched or unbranched. Preferred radicals are benzyl, phenylethyl, naphthylmethyl and naphthylethyl,
„Amino" steht erfindungsgemäß für jede beliebige substituierte oder unsubstituierte Aminogruppe, insbesondere für -NH2, -NH(C1-1B-AIKyI), -N(C1-1θ^rkyl)2, -NH^^-Aryl) oder -N(C6-10-AFyI)2, besonders bevorzugt für -NH£."Amino" according to the invention stands for any substituted or unsubstituted amino group, in particular -NH 2 , -NH (C 1-1B -alkyl), -N (C 1-1 -alkyl) -alkyl, -NH 2 -alkyl-aryl) or -N (C 6-10 -AfyI) 2 , especially preferred for -NH £ .
„Ammonium" steht erfindungsgemäß für jede beliebige substituierte oder unsubstituierte Ammoniumgruppe, insbesondere für -NH3 w, -NH2(C1-I8-AIKyIf \ -NH(C1- irAlkyl)2 w oder -N(C1-18-AIKyI)3",According to the invention, "ammonium" represents any substituted or unsubstituted ammonium group, in particular -NH 3 W , -NH 2 (C 1 -18 -alkyl) -NH (C 1 -alkyl) 2 W or -N (C 1-18 -AikyI) 3 ",
„Sulfato" steht erfindungsgemäß insbesondere Wr -O-S(O)2-O-R1 „Sulfo" für -S(O)2-O-R, „AmidosulFo" für -0-S(O)2-NR2, „Phosphato" für -0-P(O)(OR)2, „Phosphono" für -P(O)(OR)2 „Amidophosphono" für -0-P(O)(NRj)2 oder -O-P(O)(OR)(NR2) und „Amidocarbonyl" für -C(O)-NR2, wobei R jeweils unabhängig voneinander für H, M(+) F Ci-ie-Alkyl, Ce-io-Aryl oder Ci-is- Alkyl-Ce-10-Aryl steht."Sulfato" according to the invention is in particular Wr -OS (O) 2 -OR 1 "sulfo" for -S (O) 2 -OR, "amidosulfo" for -O-S (O) 2 -NR 2 , "phosphato" for 0-P (O) (OR) 2 , "phosphono" for -P (O) (OR) 2 "amidophosphono" for -O-P (O) (NRj) 2 or -OP (O) (OR) (NO 2) and "amidocarbonyl" -C (O) -NR 2 wherein each R is independently (H, M +) F Ci-ie-alkyl, Ce-io-aryl or Ci-is- alkyl-C e- 10 -aryl stands.
Erfindungsgemäß einzusetzende Imidazolium-Salze sind in den erfindunsgβmaßen Mitteln vorzugsweise in einer Menge von 0,01 bis 5,0 Gew.-%, besonders bevorzugt in einer Menge von 0,1 bis 3,0 Gew. -%, vor allem in einer Menge von 0,2 bis 2,0 Gew,-%, enthalten. Ein erfindungsgemäßes Wasch- oder Reinigungsmittel und insbesondere ein erfindungsgemäßes maschinelles Geschirrspülmittel kann weitere wasch- oder reinigungsaktive Inhaltsstoffe sowie weitere für Wasch- und Reinigungsmittel übliche Inhaltsstoffe enthalten.Imidazolium salts to be used according to the invention are preferably present in the inventive compositions in an amount of from 0.01 to 5.0% by weight, more preferably in an amount of from 0.1 to 3.0% by weight, especially in an amount from 0.2 to 2.0% by weight. A washing or cleaning agent according to the invention and in particular a machine dishwashing detergent according to the invention may contain further washing or cleaning-active ingredients as well as other ingredients customary for detergents and cleaners.
Erfindungsgemäße Wasch- oder Reinigungsmittel enthalten in der Regel einen oder mehrere Gerüststoffe (Builder), insbesondere Zeolithe, Silikate, Carbonate, organische Cobuilder und - wo keine ökologischen Gründe gegen ihren Einsatz sprechen - auch die Phosphate. Letztere sind insbesondere in Reinigungsmitteln für das maschinelle Geschirrspülen bevorzugt einzusetzende Gerüststoffe.Detergents or cleaners according to the invention generally contain one or more builders, in particular zeolites, silicates, carbonates, organic cobuilders and, where there are no ecological reasons against their use, the phosphates. The latter are particularly preferred builders to be used in automatic dishwashing detergents.
Mit Vorzug werden kristalline schichtförmige Silikate der allgemeinen Formel NaMSixO2x+I ■ y H2O eingesetzt, worin M Natrium oder Wasserstoff darstellt, x eine Zahl von 1 ,9 bis 22, vorzugsweise von 1 ,9 bis 4, wobei besonders bevorzugte Werte für x 2, 3 oder 4 sind, und y für eine Zahl von 0 bis 33, vorzugsweise von 0 bis 20 steht. Die kristallinen schichtförmigen Silikate der Formel NaMSixO2x+1 ■ y H2O werden beispielsweise von der Firma Clariant GmbH (Deutschland) unter dem Handelsnamen Na-SKS vertrieben. Beispiele für diese Silikate sind Na-SKS-1 (Na2Sb2θ45 ■ x H2O, Kenyait), Na-SKS-2 (Na2Si14O29 ■ x H2O, Magadiit), Na-SKS-3 (Na2Si8O17 ■ x H2O) oder Na-SKS-4 (Na2Si4O9 x H2O, Makatit).With preferred crystalline layered silicates of general formula NaMSi x O 2x + I ■ y H 2 O are used, wherein M is sodium or hydrogen, x is a number from 1, 9 to 22, preferably from 1: 9 to 4, wherein particularly preferred Values for x are 2, 3 or 4, and y is a number from 0 to 33, preferably from 0 to 20. The crystalline layered silicates of the formula NaMSi x O 2x + 1 ■ y H 2 O are sold for example by Clariant GmbH (Germany) under the trade name Na-SKS. Examples of these silicates are Na-SKS-1 (Na2 Sb2θ 4 5 ■ x H 2 O, kenyaite), Na-SKS-2 (Na 2 Si 14 O 29 ■ x H 2 O, magadiite), Na-SKS 3 (Na 2 Si 8 O 17 .xH 2 O) or Na-SKS-4 (Na 2 Si 4 O 9 .H 2 O, makatite).
Die erfindungsgemäßen Mittel enthalten weiterhin vorzugsweise Tenside, insbesondere ausgewählt aus nichtionischen, anionischen, kationischen und amphoteren Tensiden Als Tenside werden erfindungsgemäß vorzugsweise nichtionische, anionische und/oder amphotere Tenside eingesetzt.The agents according to the invention furthermore preferably contain surfactants, in particular selected from nonionic, anionic, cationic and amphoteric surfactants. Surfactants used according to the invention are preferably nonionic, anionic and / or amphoteric surfactants.
Als nichtionische Tenside können alle dem Fachmann bekannten nichtionischen Tenside eingesetzt werden. Als nichtionische Tenside eignen sich beispielsweise Alkylglykoside der allgemeinen Formel RO(G)x, in der R einem primären geradkettigen oder methyl verzweigten, insbesondere in 2-Stellung methylverzweigten aliphatischen Rest mit 8 bis 22, vorzugsweise 12 bis 18 C-Atomen entspricht und G das Symbol ist, das für eine Glykoseeinheit mit 5 oder 6 C-Atomen, vorzugsweise für Glucose, steht. Der Oligomerisierungsgrad x, der die Verteilung von Mono- glykosiden und Oligoglykosiden angibt, ist eine beliebige Zahl zwischen 1 und 10; vorzugsweise liegt x bei 1 ,2 bis 1 ,4.As nonionic surfactants, it is possible to use all nonionic surfactants known to the person skilled in the art. Suitable nonionic surfactants are, for example, alkyl glycosides of the general formula RO (G) x in which R corresponds to a primary straight-chain or methyl-branched, in particular 2-methyl-branched aliphatic radical having 8 to 22, preferably 12 to 18 carbon atoms and G is the Is a symbol which represents a glycose unit having 5 or 6 C atoms, preferably glucose. The degree of oligomerization x, which indicates the distribution of monoglycosides and oligoglycosides, is an arbitrary number between 1 and 10; preferably x is 1, 2 to 1, 4.
Eine weitere Klasse bevorzugt eingesetzter nichtionischer Tenside, die entweder als alleiniges nichtionisches Tensid oder in Kombination mit anderen nichtionischen Tensiden eingesetzt werden, sind alkoxylierte, vorzugsweise ethoxylierte oder ethoxylierte und propoxylierte Fettsäurealkylester, vorzugsweise mit 1 bis 4 Kohlenstoffatomen in der Alkylkette. Auch nichtionische Tenside vom Typ der Aminoxide, beispielsweise N-Kokosalkyl-N,N- dimethylaminoxid und N-Talgalkyl-N,N-dihydroxyethylaminoxid, und der Fettsäurealkanolamide können geeignet sein. Die Menge dieser nichtionischen Tenside beträgt vorzugsweise nicht mehr als die der ethoxylierten Fettalkohole, insbesondere nicht mehr als die Hälfte davon.Another class of preferred nonionic surfactants used either as the sole nonionic surfactant or in combination with other nonionic surfactants are alkoxylated, preferably ethoxylated or ethoxylated and propoxylated fatty acid alkyl esters, preferably having from 1 to 4 carbon atoms in the alkyl chain. Nonionic surfactants of the amine oxide type, for example N-cocoalkyl-N, N-dimethylamine oxide and N-tallowalkyl-N, N-dihydroxyethylamine oxide, and the fatty acid alkanolamides may also be suitable. The amount of these nonionic surfactants is preferably not more than that of the ethoxylated fatty alcohols, especially not more than half thereof.
Weitere geeignete Tenside sind Polyhydroxyfettsäureamide der FormelFurther suitable surfactants are polyhydroxy fatty acid amides of the formula
Figure imgf000010_0001
Figure imgf000010_0001
in der R für einen aliphatischen Acylrest mit 6 bis 22 Kohlenstoffatomen, R1 für Wasserstoff, einen Alkyl- oder Hydroxyalkylrest mit 1 bis 4 Kohlenstoffatomen und [Z] für einen linearen oder verzweigten Polyhydroxyalkylrest mit 3 bis 10 Kohlenstoffatomen und 3 bis 10 Hydroxylgruppen steht. Bei den Polyhydroxyfettsäureamiden handelt es sich um bekannte Stoffe, die üblicherweise durch reduktive Aminierung eines reduzierenden Zuckers mit Ammoniak, einem Alkylamin oder einem Alkanolamin und nachfolgender Acylierung mit einer Fettsäure, einem Fettsäurealkylester oder einem Fettsäurechlorid erhalten werden können.wherein R is an aliphatic acyl radical having 6 to 22 carbon atoms, R 1 is hydrogen, an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms and [Z] is a linear or branched polyhydroxyalkyl radical having 3 to 10 carbon atoms and 3 to 10 hydroxyl groups. The polyhydroxy fatty acid amides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
Zur Gruppe der Polyhydroxyfettsäureamide gehören auch Verbindungen der FormelThe group of polyhydroxy fatty acid amides also includes compounds of the formula
Figure imgf000010_0002
Figure imgf000010_0002
in der R für einen linearen oder verzweigten Alkyl- oder Alkenylrest mit 7 bis 12 Kohlenstoffatomen, R1 für einen linearen, verzweigten oder zyklischen Alkylrest oder einen Arylrest mit 2 bis 8 Kohlenstoffatomen und R2 für einen linearen, verzweigten oder zyklischen Alkylrest oder einen Aryl rest oder einen Oxy-Alkylrest mit 1 bis 8 Kohlenstoffatomen steht, wobei C-w-Alkyl- oder Phenylreste bevorzugt sind und [Z] für einen linearen Polyhydroxyalkylrest steht, dessen Alkylkette mit mindestens zwei Hydroxylgruppen substituiert ist, oder alkoxylierte, vorzugsweise ethoxylierte oder propxylierte Derivate dieses Restes.in the R is a linear or branched alkyl or alkenyl radical having 7 to 12 carbon atoms, R 1 is a linear, branched or cyclic alkyl radical or an aryl radical having 2 to 8 carbon atoms and R 2 is a linear, branched or cyclic alkyl radical or an aryl radical or an oxy-alkyl radical having 1 to 8 carbon atoms, wherein Cw-alkyl or phenyl radicals are preferred and [Z] is a linear polyhydroxyalkyl radical whose alkyl chain is substituted by at least two hydroxyl groups, or alkoxylated, preferably ethoxylated or propoxylated derivatives of this residue.
[Z] wird vorzugsweise durch reduktive Aminierung eines reduzierten Zuckers erhalten, beispielsweise Glucose, Fructose, Maltose, Lactose, Galactose, Mannose oder Xylose. Die N- Alkoxy- oder N-Aryloxy-substituierten Verbindungen können durch Umsetzung mit Fettsäuremethylestern in Gegenwart eines Alkoxids als Katalysator in die gewünschten Polyhydroxyfettsäureamide überführt werden. Die erfinduπgsgemäßen Wasch- und Reinigungsmittel enthalten in einer bevorzugten Ausfuhrungsform weiterhin Bleichmittel. Unter den als Bleichmittel dienenden, in Wasser H2O2 liefernden Verbindungen haben das Natriumpercarbonat, das Natriumperborattetrahydrat und das Natriumperboratmonohydrat besondere Bedeutung. Weitere brauchbare Bleichmittel sind beispielsweise Peroxopyrophosphate, Citratperhydrate sowie H2O2 liefernde persaure Salze oder Persäuren, wie Persulfate beziehungsweise Perschwefelsäure, Brauchbar ist auch das Harπstoffperoxohydrat Percarbamid, das durch die Formel H2N-CO-NH2 H2O2 beschrieben werden kann. Insbesondere beim Einsatz der MiUeI für das Reinigen harter Oberflachen, zum Beispiel beim maschinellen Geschirrspülen! können sie gewünschteπfalls auch Bleichmittel aus der Gruppe der organischen Bleichmittel enthalten, obwohl deren Einsatz prinzipiell auch bei Mitteln für die Textilwäsche möglich ist. Typische organische Bleichmittel sind die Diacylperoxide. wie zum Beispiel Dibeπzoylperoxid. Weitere typische organische Bleichmittel sind die Peroxysäuren, wobei als Beispiele besonders die Alkylperoxysäuren und die Arylperoxysäuren genannt werden Bevorzugte Vertreter sind (a) die Peroxybeπzσesäure und ihre riπgsubstituierten Derivate, wie Alkylperoxybenzoesäuren, aber auch Peroxy-α-Naphthoesäure und Magnesiüm-monoperphthalat, (b) die aliphatischβn oder substituiert aliphatischeπ Peroxysauren, wie Peroxylauriπsäure, Peroxystearinsäure, ε-Phthalimidoperoxycapronsäure (Phthalimidoperoxyhexansäure, PAP), o- Carboxybenzamidoperoxycapronsaure, N-Nonenylamidopβradipinsäure und N-Nonenylamidoper- succinatθ, und (c) aliphatischθ und araliphatischβ Peroxydicarboπsaureπ, wie 1 ,12- Diperoxycarbonsöure. 1 ,9-Diperoxyazelainsäure. Diperoxysebacinsäure. Diperoxybrassylsäure. die Diperoxyphthalsäuren, 2-Decyldiperoxybutan-1 ,4-disäure, N,N-Terephthaloyl-di(6-aminopercapron- säure).[Z] is preferably obtained by reductive amination of a reduced sugar, for example glucose, fructose, maltose, lactose, galactose, mannose or xylose. The N-alkoxy- or N-aryloxy-substituted compounds can be converted into the desired polyhydroxy fatty acid amides by reaction with fatty acid methyl esters in the presence of an alkoxide as catalyst. The detergents according to the invention also contain bleaches in a preferred embodiment. Among the compounds serving as bleaches in water H 2 O 2 , sodium percarbonate, sodium perborate tetrahydrate and sodium perborate monohydrate are of particular importance. Further useful bleaching agents are, for example, peroxopyrophosphates, citrate perhydrates and peroxygenic salts or peracids which yield H 2 O 2 , such as persulfates or persulfuric acid. The urea peroxohydrate percarbamide, which can be described by the formula H 2 N-CO-NH 2 H 2 O 2 , is also useful , Especially when using the MiUeI for cleaning hard surfaces, for example with automatic dishwashing ! If desired, they may also contain bleaches from the group of organic bleaches, although their use is in principle also possible with detergents. Typical organic bleaches are the diacyl peroxides. such as dibenzoyl peroxide. Further typical organic bleaching agents are the peroxyacids, examples of which are the alkyl peroxyacids and the aryl peroxyacids. Preferred representatives are (a) peroxybenzoic acid and its substituted derivatives, such as alkylperoxybenzoic acids, but also peroxy-α-naphthoic acid and magnesium monoperphthalate. (B) the aliphatic or substituted aliphatic peroxyacids, such as peroxylauric acid, peroxystearic acid, ε-phthalimidoperoxycaproic acid (phthalimidoperoxyhexanoic acid, PAP), o-carboxybenzamidoperoxycaproic acid, N-nonenylamidopipradadic acid and N-nonenylamidoper succinate, and (c) aliphatic and araliphatic peroxydicarboxylic acid, such as 1,12-diperoxycarboxylic acid , 1,9-Diperoxyazelaic acid. Diperoxysebacic. Diperoxybrassylic. the diperoxyphthalic acids, 2-decyldiperoxybutane-1, 4-diacid, N, N-terephthaloyl-di (6-aminopercaproic acid).
Als Bleichmittel können auch Chlor oder Brom freisetzende Substanzen eingesetzt werden. Unter den geeigneten Chlor oder Brom freisetzenden Materialien kommen beispielsweise heterozykiische N- Brom- und N-Chloramide, beispielsweise Trichlorisocyanursäure, TribromisocyanursaurB, Dibromisocyanursaure und/oder Dichlorisocyaπursaure (DICA) und/oder deren Salze mit Kationen wie Kalium und Natrium in Betracht. Hydaπtoinverbindungen, wie 1,3-Dichlor"5,5-dimethylhydantoin sind ebenfalls geeignet.As a bleaching agent and chlorine or bromine releasing substances can be used. Examples of suitable chlorine or bromine-releasing materials are heterocyclic N-bromo and N-chloroamides, for example trichloroisocyanuric acid, tribromoisocyanuric acid B, dibromoisocyanuric acid and / or dichloroisocyanic acid (DICA) and / or their salts with cations such as potassium and sodium. Hydantoin compounds such as 1,3-dichloro-5,5-dimethylhydantoin are also suitable.
Hinsichtlich erfindungsgemaß ersetzbaren weiteren Inhaltsstoffen, insbesondere hinsichtlich erfindungsgemäß vorzugsweise einsetzbaren Geruststoffen, Tensiden, Polymeren, Bleichmitteln, insbesondere Bieichaktivatoren und/oder Bleichkatalysatoren, Enzymen, insbesondere Amylasen, Proteasen und Amadoriasen, Lösungsmitteln, Verdickern, Sequestrierungsmitteln, Elektrolyten, optischen Aufhellern, Vergrauungsinhibitoren, Glaskorrosionsiπhibitoreπ, Korrosioπsinhibitoren, Farbubertragungsinhibitoren, Schaumiπhibitoreπ, Desintegrationshilfsmitteln, Abrasivstoffen, Farbstoffen bzw. Färbemitteln, Duftstoffen, Parfümträgern, rnikrobiellen Wirkstoffen, UV- Absorbenzien, Enzymstabilisatoren, „Soil-Release"-W]rkstoffen, Acidifiziemπgsmiitelπ und Treibmitteln sowie hinsichtlich deren bevorzugten Einsatzmengeπ wird auf die Offenlegiiπgsschnft WO2008/101810 verwiesen.With regard to inventive replaceable further ingredients, in particular with regard to inventively preferably usable Geruststoffen, surfactants, polymers, bleaching agents, especially Bieichaktivatoren and / or bleach catalysts, enzymes, especially amylases, proteases and Amadoriasen, solvents, thickeners, sequestering agents, electrolytes, optical brighteners, grayness inhibitors, Glaskorrosionsiπhibitoreπ, Corrosioπsinhibitoren, Farbubertragungsinhibitorsen, Schaumiπhibitoreπ, Disintegrationshilfsmitteln, abrasives, dyes or dyes, perfumes, perfume carriers, microbial agents, UV absorbents, enzyme stabilizers, "Soil-Release" -W rkstoffen, Acidifiziemπgsmiitelπ and Propellants and with regard to their preferred Einsatzππ reference is made to Offenlegiiπgsschnft WO2008 / 101810.
Einen eigenen Erfindungsgegenstand steifen Verfahren zur maschinellen Reinigung von Textilien oder von harten Oberflächen dar, bei denen wenigstens in einem der Verfahrensschritte ein erfindungsgemäßes Imidazolium-Salz, vorzugsweise in Kombination mit Salicylsäure oder einem Salicylsäure-Deπvat, verwendet wird.A separate subject matter of the invention is a process for the mechanical cleaning of textiles or of hard surfaces, in which at least in one of the process steps an imidazolium salt according to the invention, preferably in combination with salicylic acid or a salicylic acid derivative, is used.
Hierunter fallen sowohl manuelle als auch maschinelle Verfahren, wobei maschinelle Verfahren aufgrund ihrer präziseren Steuerbarkeit, was beispielsweise die eingesetzten Mengen und Einwirkzeiten angeht, bevorzugt sind.This includes both manual and mechanical processes, with mechanical processes being preferred on account of their more precise controllability, for example with regard to the quantities and reaction times used.
Verfahren zur Reinigung von Textilien zeichnen sich im allgemeinen dadurch aus, dass in mehreren Verfahrensschritten verschiedene reinigungsaktive Substanzen auf das Reinigungsgut aufgebracht und nach der Einwirkzeit abgewaschen werden, odBr dass das Reiniguπgsgut in sonstiger Weise mit einem Waschmittel oder einer Lösung dieses Mittels behandelt wird. Das gleiche gilt für Verfahren zur Reinigung von allen anderen Materialien als Textilien, welche unter dem Begriff „harte Oberflächen" zusammengefasst werden. Alle denkbaren Wasch- oder Reinigungsverfahren können in wenigstens einem der Verfahrensschritte um ein erfjnduπgsgemüßes ImidazoliunvSalz, vorzugsweise in Kombination mit Salicylsäure oder einem Salicylsäure-Derivat, bereichert werden, und stellen dann Ausführungsformeπ der vorliegenden Erfindung dar.Processes for the cleaning of textiles are generally distinguished by the fact that various cleaning-active substances are applied to the items to be cleaned in a plurality of process steps and washed off after the reaction time, or the product to be treated is otherwise treated with a detergent or a solution of this agent. The same applies to processes for the purification of all materials other than textiles, which are summarized under the term "hard surfaces." All conceivable washing or cleaning processes can be carried out in at least one of the process steps around an inventive imidazolium salt, preferably in combination with salicylic acid or a salicylic acid Derivative, and then constitute embodiments of the present invention.
Einen eigenen Erfindungsgegenstand stellt die Verwendung von erfindungsgemäßen Imidazolium- Salzen, vorzugsweise in Kombination mit Salicylsäure oder einem Salicylsäure-Derivat, zur Reinigung von Textilien oder von harten Oberflächen dar.A separate subject of the invention is the use of imidazolium salts according to the invention, preferably in combination with salicylic acid or a salicylic acid derivative, for the purification of textiles or hard surfaces.
Entsprechend bevorzugt gelten für diese genannten Verwendungen die oben angeführten Konzentrationsbereiche.Accordingly, the above-mentioned concentration ranges apply correspondingly for these uses.
Denn erfiπduπgsgemälϊe Imidazolium-Salze und entsprechende Kombinationen mit Salicylsäure und Salicylsäure-Derivaten können, insbesondere entsprechend den oben beschriebenen Eigenschaften und den oben beschriebenen Verfahren dazu verwendet werden, um von Textilien oder von harten Oberflächen Anschmutzungen zu beseitigen. Ausführuπgsformeπ stellen beispielsweise die Handwäsche, die manuelle Entfernung von Flecken von Textilien oder von harten Oberflächen oder die Verwendung im Zusammenhang mit einem maschinellen Verfahren dar. In einer bevorzugten Ausführungsform dieser Verwendung werden die erfindungsgemäßen Imidazolium-Salze und Salicylsäure-Derivate hierbei im Rahmen einer der oben ausgeführten Rezepturen für erfindungsgemäße Mittel, vorzugsweise Wasch- beziehungsweise Reinigungsmittel, bereitgestellt.Because erfiπduπgsgemälϊe imidazolium salts and corresponding combinations with salicylic acid and salicylic acid derivatives can, in particular according to the properties described above and the methods described above, be used to remove stains from textiles or hard surfaces. Examples of embodiments include hand washing, manual removal of stains from textiles or hard surfaces, or use in conjunction with a machine process. In a preferred embodiment of this use, the imidazolium salts and salicylic acid derivatives according to the invention are in this case provided in the context of one of the above formulations for agents according to the invention, preferably detergents or cleaners.
Ein weiterer Gegenstand der vorliegenden Erfindung ist auch ein Erzeugnis, enthaltend eine erfindungsgemäße Zusammensetzung bzw. ein erfindungsgemäßes Wasch- oder Reinigungsmittel, insbesondere einen erfindungsgemäßen Reiniger für harte Oberflachen, und einen Sprühspender. Bei dem Erzeugnis kann es sich hierbei sowohl um ein Eiπkammer- als auch um ein Mehrkammerbehältπis, insbesondere ein Zweikammerbehältnis handeln. Bevorzugt ist der Sprühspender hierbei ein manuell aktivierter Sprühspender, insbesondere ausgewählt aus der Gruppe umfassend Aerosolsprühspeπder (Druckgasbehälter; auch u.a. als Spraydose bezeichnet), selbst Druck aufbauende Sprühspender, Pumpsprühspender und Triggersprühspender, insbesondere Pumpsprühspender und Triggersprühspeπder mit einem Behälter aus transparentem Polyethylen oder Polyethylenterephthalat. Sprühspender werden ausführlicher in der WO 96/04940 (Procter & Gamble) und den darin zu Sprühspendern zitierten US-Patenten, auf die in dieser Hinsicht samtlich Bezug genommen und deren Inhalt hiermit in diese Anmeldung aufgenommen wird, beschrieben. Triggersprühspender und Pumpzerstäuber besitzen gegenüber Druckgasbehältern den Vorteil, daß kein Treibmittel eingesetzt werden muß. Durch geeignete, partikelgängige Aufsätze, Düsen etc. (sog. "nozzle-Ventile") auf dem Sprühspender kann gegebenenfalls enthaltenes Enzym in dieser Ausführungsform optional auch in auf Partikeln immobilisierter Form dem Mittel beigefügt werden und so als Reinigungsschaum dosiert werden.Another object of the present invention is also a product comprising a composition according to the invention or a detergent or cleaning agent according to the invention, in particular a hard surface cleaner according to the invention, and a spray dispenser. In the case of the product, this can be both a chamber chamber and a multi-chamber container, in particular a two-chamber container. The spray dispenser is preferably a manually activated spray dispenser, in particular selected from the group comprising aerosol sprayers (pressurized gas containers, also called spray cans), pressure-building spray dispensers, pump spray dispensers and trigger spray dispensers, in particular pump spray dispensers and trigger sprayers with a container made of transparent polyethylene or polyethylene terephthalate. Spray dispensers are described in more detail in WO 96/04940 (Procter & Gamble) and the US patents cited therein on spray dispensers, to which reference is made in this regard and the contents of which are hereby incorporated by reference. Triggersprühspender and pump sprayer have over compressed gas tanks the advantage that no propellant must be used. By means of suitable particles-passing attachments, nozzles, etc. (so-called "nozzle valves") on the spray dispenser, optionally contained enzyme in this embodiment can optionally also be added to the composition in a form immobilized on particles and thus metered in as a cleaning foam.
Erfindungsgemali besonders bevorzugte maschinelle Geschirrspülmittel, umfassenMachine dishwashing agents particularly preferred according to the invention comprise
5 bis 70 Gew -%, vorzugsweise 10 bis 60 GΘW -% und insbesondere 20 bis 50 Gew.-% Gerüstoff(e), mit Ausnahme wasch- und reinigungsaktiver Polymere, vorzugsweise Phosphate, 2 bis 28 Gew.-%, vorzugsweise 4 bis 20 Gew.-% und insbesondere 6 bis 15 Gew.-% wasch- und rβinigungsaktivβ Polymere;From 5 to 70% by weight, preferably from 10 to 60% by weight and in particular from 20 to 50% by weight, of aggregate (s), with the exception of washing and cleaning-active polymers, preferably phosphates, from 2 to 28% by weight, preferably from 4 to 20 wt .-% and in particular 6 to 15 wt .-% washing and rÄinigungsaktivβ polymers;
0,5 bis 10 Gew -%, vorzugsweise 1 bis 9 Gew -% und insbesondere 2 bis 6 Gew.-% Tensid(e), vorzugsweise nichtionische(s) und/oder amphotere(s) Tensid(e), besonders bevorzugt nichtionische(s) Tensid(e);0.5 to 10% by weight, preferably 1 to 9% by weight and in particular 2 to 6% by weight of surfactant (s), preferably nonionic and / or amphoteric surfactant (s), more preferably nonionic (s) surfactant (s);
- 0,5 bis 8 Gew.-%, vorzugsweise 1. bis 7 Gew.-% und insbesondere 2 bis 6 Gew -% Enzym{e), vorzugsweise ausgewählt aus Amylasen, Proteasen und Amadoriaseπ;From 0.5 to 8% by weight, preferably from 1 to 7% by weight and in particular from 2 to 6% by weight of enzyme (s), preferably selected from amylases, proteases and amadoriases;
2 bis 20 Gew -%, vorzugsweise 4 bis 15 Gew -% und insbesondere 6 bis 12 Gew.-% Bleichmittel, vorzugsweise Percarbonat;From 2 to 20% by weight, preferably from 4 to 15% by weight and in particular from 6 to 12% by weight of bleaching agent, preferably percarbonate;
- 0,01 bis 5 Gew.-%, vorzugsweise 0.02 bis 4 Gew.-% und insbesondere 0,05 bis 3 Gew -% Bleichkatalysatoren;0.01 to 5% by weight, preferably 0.02 to 4% by weight and in particular 0.05 to 3% by weight of bleach catalysts;
- 0,01 bis 5 Gew -%, vorzugsweise 0,02 bis 4 Gθw.-% und insbesondere 0,05 bis 3 Gew.-% Imidazolium-Salze; sowie gegebenenfalls 0,01 bis 5 Gew.-%, vorzugsweise 0,02 bis 4 Gew.-% und insbesondere 0,05 bis 3 Gew.-% Salicylsäure und/oder Salicylsäure-Derivate.0.01 to 5% by weight, preferably 0.02 to 4% by weight, and in particular 0.05 to 3% by weight, of imidazolium salts; such as optionally 0.01 to 5 wt .-%, preferably 0.02 to 4 wt .-% and in particular 0.05 to 3 wt .-% salicylic acid and / or salicylic acid derivatives.
Ganz besonders bevorzugte maschinelle Geschirrspülmittel umfassenVery particularly preferred automatic dishwashing detergents comprise
5 bis 70 Gew.-%, vorzugsweise 10 bis 60 Gew.-% und insbesondere 20 bis 50 Gew.-%From 5 to 70% by weight, preferably from 10 to 60% by weight and in particular from 20 to 50% by weight
Phosphate;Phosphate;
2 bis 28 Gew.-%, vorzugsweise 4 bis 20 Gew.-% und insbesondere 6 bis 15 Gew.-% wasch- und reinigungsaktive Polymere;2 to 28 wt .-%, preferably 4 to 20 wt .-% and in particular 6 to 15 wt .-% washing and cleaning-active polymers;
0,5 bis 10 Gew.-%, vorzugsweise 1 bis 8 Gew.-% und insbesondere 2 bis 6 Gew.-% nichtionische(s) Tensid(e);0.5 to 10% by weight, preferably 1 to 8% by weight and in particular 2 to 6% by weight of nonionic surfactant (s);
0,5 bis 8 Gew.-%, vorzugsweise 1 , bis 7 Gew.-% und insbesondere 2 bis 6 Gew.-% Enzym(e) ausgewählt aus Amylasen, Proteasen und Amadoriasen;0.5 to 8 wt .-%, preferably 1 to 7 wt .-% and in particular 2 to 6 wt .-% enzyme (s) selected from amylases, proteases and amadoriases;
2 bis 20 Gew.-%, vorzugsweise 4 bis 15 Gew.-% und insbesondere 6 bis 12 Gew.-%2 to 20% by weight, preferably 4 to 15% by weight and in particular 6 to 12% by weight
Percarbonat;percarbonate;
0,01 bis 5 Gew.-%, vorzugsweise 0,02 bis 4 Gew.-% und insbesondere 0,05 bis 3 Gew.-%0.01 to 5 wt .-%, preferably 0.02 to 4 wt .-% and in particular 0.05 to 3 wt .-%
Bleich katalysatoren; sowieBleach catalysts; such as
0,01 bis 5 Gew.-%, vorzugsweise 0,02 bis 4 Gew.-% und insbesondere 0,05 bis 3 Gew.-%0.01 to 5 wt .-%, preferably 0.02 to 4 wt .-% and in particular 0.05 to 3 wt .-%
Imidazolium-Salze; sowie gegebenenfalls 0,01 bis 5 Gew.-%, vorzugsweise 0,02 bis 4 Gew.-% und insbesondere 0,05 bis 3 Gew.-% Salicylsäure und/oder Salicylsäure-Derivate.Imidazolium salts; and optionally 0.01 to 5 wt .-%, preferably 0.02 to 4 wt .-% and in particular 0.05 to 3 wt .-% salicylic acid and / or salicylic acid derivatives.
Die Konfektionierung erfindungsgemäßer maschineller Geschirrspülmittel kann in unterschiedlicher Weise erfolgen. Die erfindungsgemäßen Mittel können in fester oder flüssiger sowie als Kombination fester und flüssiger Angebotsformen vorliegen.The preparation of automatic dishwashing agents according to the invention can take place in different ways. The compositions according to the invention can be present in solid or liquid form as well as a combination of solid and liquid forms.
Als feste Angebotsformen eignen sich insbesondere Pulver, Granulate, Extrudate oder Kompaktate, insbesondere Tabletten. Die flüssigen Angebotsformen auf Basis von Wasser und/oder organischen Lösungsmitteln können verdickt, in Form von Gelen vorliegen.Powder, granules, extrudates or compactates, in particular tablets, are particularly suitable as firm supply forms. The liquid supply forms based on water and / or organic solvents may be thickened, in the form of gels.
Erfindungsgemäße Mittel können in Form einphasiger oder mehrphasiger Produkte konfektioniert werden. Bevorzugt werden insbesondere maschinelle Geschirrspülmittel mit einer, zwei, drei oder vier Phasen. Maschinelle Geschirrspülmittel, dadurch gekennzeichnet, dass es in Form einer vorgefertigten Dosiereinheit mit zwei oder mehr Phasen vorliegt, werden besonders bevorzugt.Inventive agents can be formulated in the form of single-phase or multi-phase products. In particular, automatic dishwashing detergents with one, two, three or four phases are preferred. Machine dishwashing detergent, characterized in that it is in the form of a prefabricated dosing unit with two or more phases, are particularly preferred.
Die einzelnen Phasen mehrphasiger Mittel können die gleiche oder unterschiedliche Aggregatzustände aufweisen. Bevorzugt werden insbesondere maschinelle Geschirrspül mittel, die mindestens zwei unterschiedliche feste Phasen und/oder mindestens zwei flüssige Phasen und/oder mindestens eine feste und mindestens eine feste Phase aufweisen. Erfindungsgemäße maschinelle Geschirrspülmittel werden vorzugsweise zu Dosiereinheiten vorkonfektioniert. Diese Dosiereinheiten umfassen vorzugsweise die für einen Reinigungsgang notwendige Menge an wasch- oder reinigungsaktiven Substanzen. Bevorzugte Dosiereinheiten weisen ein Gewicht zwischen 12 und 30 g, bevorzugt zwischen 14 und 26 g und insbesondere zwischen 16 und 22 g auf.The individual phases of multiphase agents may have the same or different states of aggregation. Machine dishwashing detergents which have at least two different solid phases and / or at least two liquid phases and / or at least one solid and at least one solid phase are preferred. Automatic dishwasher detergents according to the invention are preferably prefabricated to form metering units. These metering units preferably comprise the necessary for a cleaning cycle amount of washing or cleaning-active substances. Preferred metering units have a weight between 12 and 30 g, preferably between 14 and 26 g and in particular between 16 and 22 g.
Das Volumen der vorgenannten Dosiereinheiten sowie deren Raumform sind mit besonderem Vorzug so gewählt, dass eine Dosierbarkeit der vorkonfektionierten Einheiten über die Dosierkammer einer Geschirrspülmaschine gewährleistet ist. Das Volumen der Dosiereinheit beträgt daher bevorzugt zwischen 10 und 35 ml, vorzugsweise zwischen 12 und 30 ml und insbesondere zwischen 15 und 25 ml.The volume of the aforementioned metering units and their spatial form are selected with particular preference so that a metering of the prefabricated units is ensured via the metering chamber of a dishwasher. The volume of the dosing unit is therefore preferably between 10 and 35 ml, preferably between 12 and 30 ml and in particular between 15 and 25 ml.
Die erfindungsgemäßen maschinellen Geschirrspülmittel, insbesondere die vorgefertigten Dosiereinheiten weisen mit besonderem Vorzug eine wasserlösliche Umhüllung auf.The automatic dishwasher detergents according to the invention, in particular the prefabricated metering units, have a water-soluble coating, with particular preference.
Die nachfolgenden Beispiele erläutern die Erfindung weiter, ohne sie darauf zu beschränken.The following examples further illustrate the invention without being limited thereto.
Ausführungsbeispieleembodiments
Beispiel 1 : Synthese von Imidazolium-SalzenExample 1: Synthesis of imidazolium salts
Allgemeine Synthesevorschrift zur Darstellung von Imidazoliumsalzen AA1 :General procedure for the preparation of imidazolium salts AA1:
Reaktionsschema:Scheme:
Figure imgf000015_0001
Figure imgf000015_0001
0,1 mol Bromacetophenon bzw. Chloracetophenon werden in 60 ml abs. Ethylacetat gelöst .Unter N2 wird auf ca. 700C erwärmt und 0,06 mol Imidazol-Derivat in 15 ml abs. Ethylacetat zugetropft.0.1 mol bromoacetophenone or chloroacetophenone are abs. In 60 ml. Under N 2 is heated to about 70 0 C and 0.06 mol of imidazole derivative in 15 ml of abs. Ethyl acetate was added dropwise.
Rühren des Reaktionsgemisches für 3h am Rückfluß. Anschließend wird auf Raumtemperatur abgekühlt, wobei ein weißer Feststoff ausfällt. Dieser wird abgesaugt und mit wenig kaltem Ethylacetat gewaschen. Umkristallisation des Feststoffes aus 30 ml Ethanol liefert weißes Kristalle in ca. 80% Ausbeute.Stir the reaction mixture for 3h at reflux. It is then cooled to room temperature, whereby a white solid precipitates. This is filtered off with suction and washed with a little cold ethyl acetate. Recrystallization of the solid from 30 ml of ethanol gives white crystals in about 80% yield.
Nach dem oben beschriebenen Verfahren AA1 wurden die folgenden Verbindungen synthetisiert: Phenacylbenzylimidazoliumbromid Huc-Ve-9329-182Following procedure AA1 described above, the following compounds were synthesized: Phenacylbenzylimidazolium bromide Huc-Ve-9329-182
Figure imgf000016_0001
Figure imgf000016_0001
Formula Weight =3572438314Formula Weight = 3572438314
1H-NMR (400MHz, DMSO): δ= 10.04 (s, 1H), 7.98 (d, 2H), 7.68 (s, 1H), 7.55 (dd, 1H), 7.34 (m, 8H), 6.31 (s, 2H), 5,45 (s, 2H) 1 H-NMR (400MHz, DMSO): δ = 10.04 (s, 1H), 7.98 (d, 2H), 7.68 (s, 1H), 7.55 (dd, 1H), 7.34 (m, 8H), 6.31 (s , 2H), 5.45 (s, 2H)
Phenacylbenzylimidazoliumchlorid Huc-Ve-9329-184Phenacylbenzylimidazolium chloride Huc-Ve-9329-184
Figure imgf000016_0002
Figure imgf000016_0002
Formula Weight =3127928314Formula Weight = 3127928314
1H-NMR (400MHz, DMSO): δ= 10.32 (s, 1H), 8.00 (d, 2H), 7.60 (m, 2H), 7.38 (m, 7H), 7.24 (d, 1H), 6.32 (s, 2H), 5,44 (s, 2H) 1 H-NMR (400MHz, DMSO): δ = 10.32 (s, 1H), 8.00 (d, 2H), 7.60 (m, 2H), 7.38 (m, 7H), 7.24 (d, 1H), 6.32 (s , 2H), 5.44 (s, 2H)
Phenacylbenzylethylimidazoliumchlorid Huc-Ve-9329-195Phenacylbenzylethylimidazolium chloride Huc-Ve-9329-195
Figure imgf000016_0003
Figure imgf000016_0003
Formula Weight =3268194114Formula Weight = 3268194114
1H-NMR (400 MHz, DMSO): δ = 8,16 (m, 2H), 7,75 (s, 1H), 7,65 (m, 1H), 7,55 (m, 2H), 7, 42 (m, 2H), 7, 28 (m, 4H), 6,45 (s, 2H), 5,41 (s, 2H) Methylphenacylbenzylmethylimidazoliumbromid Huc-Ve-9660-035 1 H-NMR (400 MHz, DMSO): δ = 8.16 (m, 2H), 7.75 (s, 1H), 7.65 (m, 1H), 7.55 (m, 2H), 7 , 42 (m, 2H), 7, 28 (m, 4H), 6.45 (s, 2H), 5.41 (s, 2H) Methylphenacylbenzylmethylimidazolium bromide Huc-Ve-9660-035
Figure imgf000017_0001
Figure imgf000017_0001
Formula Weight = 385 2969914Formula Weight = 385 2969914
1H-NMR (400 MHz, DMSO): δ = 7,96 (d, 2H), 7,49 (m, 6H), 7,41 (s, 1 H), 7,34 (d, 2H), 5,47 (s, 2H), 2,52 (s, 3H), 2,45 (s, 3H). 1 H-NMR (400 MHz, DMSO): δ = 7.96 (d, 2H), 7.49 (m, 6H), 7.41 (s, 1H), 7.34 (d, 2H), 5.47 (s, 2H), 2.52 (s, 3H), 2.45 (s, 3H).
Beispiel 2: Überprüfung der Waschleistung an hartnäckigem TestschmutzExample 2: Checking the Washing Performance on Stubborn Test Dirt
Der Testschmutz wird durch Einbrennen einer Mischung aus Sahne, Vollei und Maisstärke auf einer glasierten Keramikoberfläche erhalten. Gespült wird dieser Testschmutz dann mit einer Spülmaschine G 698 SC Sensorplus der Fa. Miele im Intensivspülprogramm (500C, 107 Minuten). Die Menge entfernten Schmutzes wird gravimetrisch bestimmt und die Ergebnisangabe erfolgt in Prozent bezogen auf die Verbesserung des Spülergebnisses im Vergleich zu einem handelsüblichen Referenzgeschirrspülmittel .The test soil is obtained by baking a mixture of cream, whole egg and cornstarch on a glazed ceramic surface. This test dirt is then rinsed with a dishwasher G 698 SC Plus from sensor. Miele in Intensivspülprogramm (50 0 C, 107 minutes). The amount of soil removed is determined gravimetrically and the result is expressed in percent based on the improvement in the washing result compared to a commercial reference dishwashing detergent.
Die Zugabe der jeweiligen Waschkraftverstärker on-top zum Referenzmaschinengeschirrspülmittel (Referenz-MGSM) führt zu den in Tabelle 1 dargestellten verbesserten relativen Schmutzablösungen (bezogen auf das Referenz-MGSM).The addition of the respective detergency enhancers on-top to the reference machine dishwashing detergent (reference MGSM) results in the improved relative soil removals (relative to the reference MGSM) shown in Table 1.
Tabelle 1: Verbesserung der Schmutzablösung gegenüber Referenz-MGSMTable 1: Improvement of soil release over reference MGSM
Figure imgf000017_0002
Wie der Tabelle zu entnehmen führt die Zugabe von Imidazoliumsalzen zu einer deutlichen Verbesserung der Schmutzablösung von den Keramikflächen (Zeile 1 und 2). Die Schmutzablösung konnte jedoch durch zusätzliche Zugabe von Salicylsäure oder Salicylsäure- Derivaten nochmals deutlich verbessert werden (Zeile 4 und 5). Dies war vor allem insofern überraschend, als dass die Zugabe von Salicylsäure alleine zu keiner Verbesserung der Schmutzablösung führt (Zeile 3), so dass von einem synergistischen Effekt des Imidazolium-Salzes in Kombination mit Salicylsäure und/oder deren Derivat ausgegangen werden muss.
Figure imgf000017_0002
As shown in the table, the addition of imidazolium salts leads to a significant improvement in soil release from the ceramic surfaces (lines 1 and 2). However, the soil release could be significantly improved by additional addition of salicylic acid or salicylic acid derivatives (lines 4 and 5). This was surprising in particular insofar as the addition of salicylic acid alone does not lead to an improvement in soil release (line 3), so that a synergistic effect of the imidazolium salt in combination with salicylic acid and / or its derivative must be assumed.

Claims

Patentansprüche claims
1. Wasch- oder Reinigungsmittel enthaltend mindestens ein Imidazoliumsalz.1. washing or cleaning agent containing at least one imidazolium salt.
2. Wasch- oder Reinigungsmittel nach Anspruch 1 , dadurch gekennzeichnet, dass es sich bei dem Imidazolium-Kation des Imidazolium-Salzes um eine Verbindung der allgemeinen Formel (I)2. washing or cleaning agent according to claim 1, characterized in that it is the imidazolium cation of the imidazolium salt to a compound of general formula (I)
R4R4
Figure imgf000019_0001
Figure imgf000019_0001
handelt, dadurch gekennzeichnet, dass R1 , R2, R3, R4 und R5 unabhängig voneinander für Trifluormethyl, Wasserstoff, Alkyl, Cycloalkyl, Cycloalkylalkyl, Alkenyl, Alkinyl, Heteroalkyl, Heterocycloalkyl, Alkoxy, Alkoxyalkyl, Alkylsulfanyl, Alkylsulfinyl, Alkylsulfonyl, Alkanoyl, Alkanoyloxy, Alkoxycarbonyl, Alkylaminocarbonyl, Alkylsulfanylcarbonyl, Hydroxy, Hydroxyalkyl, Hydroxycarbonyl, Amino, Alkylamino, Aryl, Arylalkyl, Aryloxy, Arylamino, Arylsulfanyl, Arylsulfinyl, Arylsulfonyl, Arylcarbonyl, Arylcarbonyloxy, Aryloxycarbonyl, Arylaminocarbonyl, Arylsulfanylcarbonyl, Heteroaryl, Heteroarylalkyl, Heteroaryloxy, Heteroarylamino, Heteroarylsulfanyl, Heteroarylsulfonyl, Heteroarylsulfoxidyl, Heteroarylcarbonyl, Heteroarylcarbonyloxy, Heteroaryloxycarbonyl, Heteroarylaminocarbonyl, Heteroarylsulfanylcarbonyl, Alkoxysulfonyl, Alkoxycarbinol, Sulfo, Sulfino, Sulfeno, Formyl oder Thioformyl stehen, wobei alle Reste des sich so ergebenden Moleküls jeweils unabhängig voneinander gegebenenfalls auch ein- oder mehrfach substituiert sein können.characterized in that R 1, R 2, R 3, R 4 and R 5 independently of one another represent trifluoromethyl, hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, heteroalkyl, heterocycloalkyl, alkoxy, alkoxyalkyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkanoyl, alkanoyloxy, Alkoxycarbonyl, alkylaminocarbonyl, alkylsulfanylcarbonyl, hydroxy, hydroxyalkyl, hydroxycarbonyl, amino, alkylamino, aryl, arylalkyl, aryloxy, arylamino, arylsulfanyl, arylsulfinyl, arylsulfonyl, arylcarbonyl, arylcarbonyloxy, aryloxycarbonyl, arylaminocarbonyl, arylsulfanylcarbonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylamino, heteroarylsulfanyl, Heteroarylsulfonyl, heteroarylsulfoxide, heteroarylcarbonyl, heteroarylcarbonyloxy, heteroaryloxycarbonyl, heteroarylaminocarbonyl, heteroarylsulfanylcarbonyl, alkoxysulfonyl, alkoxycarbinol, sulfo, sulfino, sulfeno, formyl or thioformyl, all of the resulting molecule being independently given if one or more times can be substituted.
3. Wasch- oder Reinigungsmittel nach Anspruch 2, dadurch gekennzeichnet, dass R1 und R4 unabhängig voneinander für gegebenenfalls substituiertes Alkyl, Aryl, Arylalkyl, Alkylcarbonylalkyl oder Arylcarbonylalkyl stehen und R2, R3 und R5 unabhängig voneinander für Wasserstoff oder gegebenenfalls substituiertes Alkyl stehen.3. washing or cleaning agent according to claim 2, characterized in that R1 and R4 independently of one another represent optionally substituted alkyl, aryl, arylalkyl, Alkylcarbonylalkyl or Arylcarbonylalkyl and R2, R3 and R5 are independently hydrogen or optionally substituted alkyl.
4. Wasch- oder Reinigungsmittel nach Anspruch 2 oder 3, dadurch gekennzeichnet, dass R1 einen aromatischen Rest umfasst. 4. washing or cleaning agent according to claim 2 or 3, characterized in that R1 comprises an aromatic radical.
5. Wasch- oder Reinigungsmittel nach einem der Ansprüche 2 bis 4, dadurch gekennzeichnet, dass R4 einen aromatischen Rest umfasst.5. washing or cleaning agent according to one of claims 2 to 4, characterized in that R4 comprises an aromatic radical.
6. Wasch- oder Reinigungsmittel nach einem der Ansprüche 2 bis 5, dadurch gekennzeichnet, dass R1 und R4 unabhängig voneinander für gegebenenfalls substituiertes Phenyl, Phenyl-Ci-6-alkyl oder Phenylcarbonyl-Ci-e-alkyl stehen und die Reste R2, R3 und R5 unabhängig voneinander für Wasserstoff oder gegebenenfalls substituiertes C-ι_6-Alkyl stehen.6. washing or cleaning agent according to one of claims 2 to 5, characterized in that R1 and R4 independently of one another represent optionally substituted phenyl, phenyl-Ci-6-alkyl or phenylcarbonyl-Ci-e-alkyl and the radicals R2, R3 and R5 is hydrogen or optionally substituted C-ι_ 6 alkyl independently of one another.
7. Wasch- oder Reinigungsmittel nach einem der Ansprüche 2 bis 6, dadurch gekennzeichnet, dass R1 für einen gegebenenfalls substituierten Phenacyl-Rest steht.7. washing or cleaning agent according to one of claims 2 to 6, characterized in that R1 represents an optionally substituted phenacyl radical.
8. Wasch- oder Reinigungsmittel nach einem der Ansprüche 2 bis 7, dadurch gekennzeichnet, dass R4 für einen gegebenenfalls substituierten Phenylmethyl-Rest steht.8. washing or cleaning agent according to one of claims 2 to 7, characterized in that R4 is an optionally substituted phenylmethyl radical.
9. Wasch- oder Reinigungsmittel nach einem der Ansprüche 1 bis 8 , dadurch gekennzeichnet, dass es sich bei dem Imidazolium-Kation des Imidazolium-Salzes um eine Verbindung gemäß Formel (II) oder gemäß Formel (IM)9. washing or cleaning agent according to one of claims 1 to 8, characterized in that it is the imidazolium cation of the imidazolium salt to a compound of formula (II) or according to formula (IM)
Figure imgf000020_0001
Figure imgf000020_0001
handelt, wobei die genannten Verbindungen gegebenenfalls auch ein- oder mehrfach substituiert sein können.where appropriate, said compounds may also be monosubstituted or polysubstituted.
10. Wasch- oder Reinigungsmittel nach einem der Ansprüche 2 bis 9 , dadurch gekennzeichnet, dass die Substituenten ausgewählt sind aus Alkyl, Halogen, Hydroxy, Hydroxyalkyl, Hydroxycarbonyl, Alkoxy, Alkoxyalkyl, Alkoxycarbonyl, Amino und Alkylamino. 10. Washing or cleaning agent according to one of claims 2 to 9, characterized in that the substituents are selected from alkyl, halogen, hydroxy, hydroxyalkyl, hydroxycarbonyl, alkoxy, alkoxyalkyl, alkoxycarbonyl, amino and alkylamino.
11. Wasch- oder Reinigungsmittel nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass das Anion ausgewählt ist aus Chlorid, Bromid, lodid, Fluorid, Sulfat, Sulfit, Nitrat und Hydrogencarbonat.11. Washing or cleaning agent according to one of the preceding claims, characterized in that the anion is selected from chloride, bromide, iodide, fluoride, sulfate, sulfite, nitrate and bicarbonate.
12. Wasch- oder Reinigungsmittel nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass es Salicylsäure, ein Salicylsäure-Derivat oder Mischungen davon enthält.12. Washing or cleaning agent according to one of the preceding claims, characterized in that it contains salicylic acid, a salicylic acid derivative or mixtures thereof.
13. Wasch- oder Reinigungsmittel nach Anspruch 12, dadurch gekennzeichnet, dass es sich bei dem Salicylsäure-Derivat um 2-Hydroxybenzoesäure handelt, die durch mindestens einen weiteren Rest ausgewählt aus Hydroxy, Amino, Halogen, insbesondere Chlor, Brom oder Fluor, Ci-6-Alkyl, Ci-6-Alkoxy, Ci-6-Alkylamino oder Di-(Ci-6-Alkyl)amino substituiert ist.13. washing or cleaning agent according to claim 12, characterized in that it is the salicylic acid derivative is 2-hydroxybenzoic acid, which by at least one further radical selected from hydroxy, amino, halogen, in particular chlorine, bromine or fluorine, Ci- 6-alkyl, Ci-6-alkoxy, Ci-6-alkylamino or di- (Ci-6-alkyl) amino substituted.
14. Wasch- oder Reinigungsmittel nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass es mindestens ein Tensid enthält.14. Washing or cleaning agent according to one of the preceding claims, characterized in that it contains at least one surfactant.
15. Wasch- oder Reinigungsmittel nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass es mindestens ein Enzym ausgewählt aus Amylasen, Proteasen und Amadoriasen enthält.15. Washing or cleaning agent according to one of the preceding claims, characterized in that it contains at least one enzyme selected from amylases, proteases and amadoriases.
16. Wasch- oder Reinigungsmittel nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass es sich um ein Reinigungsmittel für harte Oberflächen handelt.16. Washing or cleaning agent according to one of the preceding claims, characterized in that it is a cleaning agent for hard surfaces.
17. Wasch- oder Reinigungsmittel nach Anspruch 16, dadurch gekennzeichnet, dass es sich um ein maschinelles Geschirrspülmittel oder um ein Handgeschirrspülmittel handelt.17. Washing or cleaning agent according to claim 16, characterized in that it is a machine dishwashing detergent or a hand dishwashing detergent.
18. Wasch- oder Reinigungsmittel nach Anspruch 17, dadurch gekennzeichnet, dass das maschinelle Geschirrspülmittel in Tabletten-Form vorliegt.18. Washing or cleaning agent according to claim 17, characterized in that the automatic dishwashing detergent is in tablet form.
19. Wasch- oder Reinigungsmittel nach einem der Ansprüche 1 bis 15, dadurch gekennzeichnet, dass es sich um ein Textil wasch mittel handelt.19. Washing or cleaning agent according to one of claims 1 to 15, characterized in that it is a textile washing agent.
20. Wasch- oder Reinigungsmittel nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass es sich um ein mehrphasiges Mittel handelt.20. Washing or cleaning agent according to one of the preceding claims, characterized in that it is a multi-phase agent.
21. Verwendung eines Wasch- oder Reinigungsmittels nach einem der Ansprüche 1 bis 20 zur Reinigung harter Oberflächen. 21. Use of a washing or cleaning agent according to one of claims 1 to 20 for cleaning hard surfaces.
22. Verwendung eines Wasch- oder Reinigungsmittels nach einem der Ansprüche 1 bis 20 zur Reinigung textiler Flächengebilde.22. Use of a washing or cleaning agent according to one of claims 1 to 20 for cleaning textile fabrics.
23. Verwendung nach Anspruch 21 oder 22 zur Entfernung von eingebrannten und/oder hartnäckigen Anschmutzungen.23. Use according to claim 21 or 22 for the removal of baked-on and / or persistent stains.
24. Verfahren zur Reinigung von Geschirr in einer Geschirrspülmaschine, bei welchem ein Wasch- oder Reinigungsmittel nach einem der Ansprüche 1 bis 20 während des Durchlaufens eines Geschirrspülprogramms vor Beginn des Hauptspülgangs oder im Verlaufe des Hauptspülgangs in den Innenraum einer Geschirrspülmaschine eindosiert wird.24. A method for cleaning dishes in a dishwasher, wherein a detergent or cleaning agent is metered according to one of claims 1 to 20 during the passage of a dishwashing program before the start of the main wash cycle or in the course of the main wash cycle in the interior of a dishwasher.
25. Imidazolium-Salz, dadurch gekennzeichnet, dass es als Imidazolium-Kation eine Verbindung der allgemeinen Formel (II) oder der allgemeinen Formel (III)25. Imidazolium salt, characterized in that it comprises as imidazolium cation a compound of general formula (II) or general formula (III)
Figure imgf000022_0001
Figure imgf000022_0001
enthält, wobei die genannte Verbindung gegebenenfalls auch ein- oder mehrfach substituiert sein kann. optionally, said compound may also be mono- or polysubstituted.
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