WO2019154613A1 - Composition de détergents à limite d'écoulement - Google Patents

Composition de détergents à limite d'écoulement Download PDF

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Publication number
WO2019154613A1
WO2019154613A1 PCT/EP2019/051338 EP2019051338W WO2019154613A1 WO 2019154613 A1 WO2019154613 A1 WO 2019154613A1 EP 2019051338 W EP2019051338 W EP 2019051338W WO 2019154613 A1 WO2019154613 A1 WO 2019154613A1
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group
alkyl
alkyl group
aryl
formula
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PCT/EP2019/051338
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German (de)
English (en)
Inventor
Anna KLEMMER
Peter Schmiedel
Filiz Yapici
Boris Nachtsheim
Dominik Göbel
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Henkel Ag & Co. Kgaa
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Priority to EP19702202.3A priority Critical patent/EP3749739B1/fr
Publication of WO2019154613A1 publication Critical patent/WO2019154613A1/fr

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    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/0013—Liquid compositions with insoluble particles in suspension
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • 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
    • C11D3/33—Amino carboxylic acids

Definitions

  • the present invention is in the technical field of liquid surfactant compositions and relates to the generation of yield value in said liquid surfactant compositions. Furthermore, the present invention relates to a process for the preparation of the said liquid limit liquid surfactant compositions and to a process for textile treatment with said liquid surfactant composition.
  • liquid surfactant compositions for incorporation into liquid surfactant compositions, in particular washing or
  • Detergents either offer those ingredients that dissolve in the liquid phase of the agent or can be suspended according to homogeneous unresolved. In the case of insoluble ingredients, a stable, homogeneous suspension is necessary for the function and aesthetics of the detergent. Sedimented solid particles can clump and when applied to local overconcentrations of the ingredient and thus to
  • Visible clumps, greasy precipitates, or solid ingredient deposits on an e.g. transparent wall of the storage vessel also mean an aesthetic flaw.
  • liquid phase incorporated and (possibly colored) recognizable by the naked human eye in suspension as individualized particles
  • Solid particles are often referred to as speckles. Such particles have for this purpose a corresponding particle size and offer the consumer an aesthetic appeal.
  • Microcapsules are also solid ingredients and include any type of capsule known to those skilled in the art, but especially core-shell capsules and matrix capsules.
  • Matrix capsules are porous shaped bodies that have a structure similar to a sponge.
  • Core-shell capsules are shaped bodies having a core and a shell. However, all of these tend
  • Solid particles especially the speckles, in liquid surfactant compositions for sedimentation.
  • the sedimentation of particles from the suspension is usually avoided by the use of surfactant compositions having a flow limit.
  • a yield point can be generated by the selection of special surfactant combinations usually in the presence of an electrolyte salt by establishing a lamellar phase.
  • the use of selected polymeric thickeners is also conceivable for generating a yield stress.
  • surfactant compositions having a high surfactant concentration are difficult to endow with a yield value in the range of 0.01 to 5 Pa.
  • lyotropic liquid-crystalline mesophases is usually achieved at high surfactant concentration too high yield point.
  • the flow behavior is inhomogeneous in such a case (so-called "lumpy" flow).
  • too high a flow limit causes the suspended particles to adhere to the wall of the storage vessel of the surfactant composition.
  • WO 2002/40627 relates to aqueous liquid detergents which comprise a textiles-substantive agent with low solubility, a crystalline hydroxyl-containing
  • Preparation of the liquid detergent Premix contains water, surfactant and 0, 1 to 5 wt .-% of said thickening agent in crystalline form as a solid.
  • the publication WO 2005/012475 also relates to liquid detergents with yield point, which are produced by the use of an already structured premix containing a hydroxy-containing thickener in crystalline form.
  • the publication WO 2015/200062 relates to a premix for the preparation of liquid detergents with yield point, which is already structured by a crystalline hydroxyl-containing thickener and additionally contains an alkyl sulfate surfactant.
  • the present invention has for its object to provide liquid surfactant compositions, in particular detergents or cleaners with excellent detergency or cleaning power, which have a yield point and in which solid particles (especially speckles) can be homogeneously suspended, so that they are stable in storage conditions
  • any liquid surfactant compositions should be structured without yield point by adding a thickener.
  • the thickening effect should thus be almost independent of the surfactants contained or of the formation of liquid-crystalline phases.
  • a first subject of the invention is therefore a liquid surfactant composition with yield point, in particular detergent, based on their total weight
  • R 1 , R 2 , R 3 and R 4 independently represent a hydrogen atom, a
  • R 5 represents a hydrogen atom, a linear (C 1 to C 6) alkyl group, a branched (C 3 to Cio) alkyl group, a (C 3 to C 6) cycloalkyl group, a (C 2 to C 6) alkenyl group, a (C 2 to C 6 ) Alkynyl group, a (C 1 -C 4 ) -hydroxyalkyl group, a (C 1 -C 4 ) -alkoxy (C 1 -C 4 ) -alkyl group, a (C 1 -C 4 ) -acyloxy- (C 1 -C 4 ) - alkyl group, an aryloxy- (C 1 -C 4 ) -alkyl group, a 0- (aryl- (C 1 -C 4 ) -alkyl) oxy- (C 1 -C 4 ) -alkyl group, a (C 1 -C 4 ) -alkyl
  • Aminocarbonyl- (C 1 -C 4) -alkyl group an N- (C 1 -C 4 ) -alkylaminocarbonyl- (C 1 -C 4 ) -alkyl group, an N, N-di (C 1 -C 4 ) -alkyl) aminocarbonyl- (C 1 -C 4 ) -alkyl group; C 4 ) alkyl group, an N- (C 2 -C 8) -acylaminocarbonyl (C 1 -C 4 ) -alkyl group, an N, N- (C 2 -C 8) -diacylaminocarbonyl- (C 1 -C 4 ) -alkyl group, an N- (C 2 -C 8) -Acyl-N- (C 1 -C 4 ) -alkylaminocarbonyl- (C 1 -C 4 ) -alkyl group, an N- (aryl- (C
  • R 5 and R 1 are preferably all defined under the definitions of R 5 and R 1 according to formula (I) radicals which are different from a hydrogen atom, in particular a hydroxy group, an amino group, a (C 1 -C 6) -alkyl group, a (C 2 -C 6) -alkenyl group, a (C 2 -C 6) -acyl group, a (C 2 -C 6) -acyloxy group, a (C 1 -C 6) alkoxy group, an amino group, a (C2-C6) acylamino group, a (Ci-C6) alkylaminocarbonyl group, an aryl group, an aroyl group, an aroyloxy group, an aryloxy group, an aryl (Ci-C4) - alkyloxy group, an aryl (C 1 -C 3) -alkyl group, a heteroaryl group, a heteroaryl (C 1 -C 3)
  • alkyl group (or an alkyl structure fragment of a more complex group) is understood according to the invention to mean a group selected from linear alkyl group of branched alkyl group or cyclic alkyl group (also: cycloalkyl group).
  • Preferred linear or branched (C 1 -C 6) -alkyl groups are selected from among methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, n-hexyl.
  • Preferred branched (C3-Cio) -alkyl groups are selected from iso-propyl, sec-butyl, isobutyl, tert-butyl, neo-pentyl, iso-octyl, 2-ethylhexyl, 2-ethylheptyl.
  • Preferred cyclic alkyl groups ((C3-C6) -cycloalkyl groups) are selected from cyclopentyl, cyclohexyl.
  • Preferred (C 2 -C 6) alkenyl groups are selected from vinyl, allyl, 2-butenyl.
  • Preferred (C 2 -C 6) alkynyl groups are selected from ethynyl, propargyl, but-2-ynyl, hex-3-ynyl.
  • Preferred (C 2 -C 6) -acyl groups are selected from acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl, in particular acetyl.
  • Preferred (C 2 -C 6) -acyloxy groups are selected from acetyloxy, propanoyloxy, butanoyloxy, pentanoyloxy and hexanoyloxy, especially acetyloxy.
  • an alkoxy group is understood as meaning an alkyl group which bonds via an oxygen atom and is selected from a linear alkyl group of branched alkyl group or cyclic alkyl group (also: cycloalkyl group).
  • Preferred (C 1 -C 6) -alkoxy groups are
  • Preferred (C 2 -C 6) -acylamino groups are acetylamino, propanoylamino, butanoylamino, pentanoylamino and hexanoylamino, in particular acetylamino.
  • Preferred aryl groups are phenyl, naphthyl, anthracenyl, these being substituted or unsubstituted.
  • Aroyl groups are arene carbonyl groups in which a carbonyl group bonds directly to the aromatic ring system.
  • Preferred aroyl groups are benzoyl, naphthoyl and anthracenoyl, which are substituted or unsubstituted.
  • Aroyloxy groups are aroyl groups that attach via an additional carbon atom-binding oxygen atom.
  • Preferred aroyloxy groups are selected from benzoyloxy, naphthoyloxy and anthracenoyloxy, these being substituted or unsubstituted.
  • a preferred aryloxy group is the phenoxy group or the naphthoxy group, which are substituted or unsubstituted.
  • Preferred aryl- (C 1 -C 3) -alkyl groups are selected from benzyl, 2-phenylethyl, naphthylmethyl,
  • Preferred heteroaryl groups are pyridyl, pyrimidinyl, imidazolyl, indolyl, furyl, thiophenyl, 1, 3,5-triazolyl
  • Preferred heteroaryl (C 1 -C 3) -alkyl groups are selected from furfuryl, 2-indol-3-yl-ethyl, indole
  • Preferred liquid compositions of the invention contain, based on the
  • composition 2,5-Diketopiperazine compound according to formula (I) in a total amount of at least 0.01% by weight, in particular from 0.01 to 2.0% by weight. It has again turned out to be particularly preferred when the inventive
  • compositions in each case based on the total weight of the composition, of 2,5-diketopiperazine compound of the formula (I) in a total amount of at least 0.05% by weight, in particular of at least 0.1% by weight, more preferably of at least 0 , 3 wt .-% contains. More preferred (in each case based on the total weight of
  • composition 2,5-diketopiperazine compound according to formula (I) in a total amount of 0.05 to 1, 8 wt .-%, in particular from 0.1 to 1, 5 wt .-%, most preferably from 0, 3 to 1, 0 wt .-%, most preferably from 0.5 to 1, 0 wt .-%, included.
  • compositions according to the invention comprise at least one 2,5-diketopiperazine compound of the formula (Ia)
  • R 1 and R 5 are as defined under formula (I) (vide supra). It has proved to be preferred if the radical R 1 according to formula (I) and according to formula (I-a) binds in the para position of the phenyl ring. Therefore, for the purposes of the present invention, those compositions according to the invention which contain at least one 2,5-diketopiperazine compound according to formula (Ib) are preferred.
  • R 1 and R 5 are as previously defined under formula (I) (vide supra).
  • the numerals 3 and 6 positioned on the ring atoms in formula (lb) are illustrative only of positions 3 and 6 of the diketopiperazine ring, as generally used in the context of the invention for the
  • Particularly preferred compounds of the formula (I-b) have the following radicals:
  • radicals R 1 to R 5 apply to compounds of the formula (I), but also to compounds of the formulas (Ia) and (Ib), with the proviso that for the formulas (Ia) and (Ib) the radicals R 2 , R 3 and R 4 are necessarily a hydrogen atom. It has proved to be advantageous if at least one compound of the formula (I) is present in the composition according to the invention in which, according to formula (I), the radicals R 1 ,
  • R 2 , R 3 and R 4 independently represent a hydrogen atom, a hydroxy group, a methyl group, an ethyl group, an iso-propyl group, an n-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, phenyl group, benzyl group, methoxy group, (C 2 -C 6) acyloxy group, aryloxy group, tosyloxy group, triflyloxy group, benzyloxy group or benzoyloxy group.
  • compositions according to the invention which have been found to contain at least one compound according to formula (I) in which R 5 is a hydrogen atom, a methyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a 2- (Methylsulfanyl) ethyl group, a hydroxymethyl group, a (C1-C3) alkoxymethyl group, a benzyloxymethyl group, an acetyloxymethyl group, a
  • Benzoyloxymethyl group a tosyloxymethyl group, a 1-hydroxyethyl group, a 1- (C 1 -C 3) alkoxy) ethyl group, a 1- (acetyloxy) ethyl group, a 1- (benzoyloxy) ethyl group, a 1- (tosyloxy) ethyl group, a mercaptomethyl group , a (C 1 -C 3) -alkylsulfanylmethyl group, an acetylsulfanylmethyl group, a benzoylsulfanylmethyl group, a tosylsulfanylmethyl group, a group according to formula (II),
  • R ' is a hydrogen atom, a (C 1 to C 4 ) -alkyl group, a (C 2 to C 4 ) -alkenyl group, an aryl group or an aryl- (C 1 to C 4 ) -alkyl group,
  • R ' is a hydrogen atom, a (C 1 to C 4 ) -alkyl group, a (C 2 to C 4 ) -alkenyl group, an aryl group or an aryl- (C 1 to C 4 ) -alkyl group,
  • n 0 or 1
  • X is an oxygen atom or a group -NH- and R "is a hydrogen atom, a (Ci-C 4 ) alkyl group, a (C2 to C 4 ) alkenyl group, a Aryl group or an aryl (Ci to C 4 ) alkyl group means
  • n 1 or 2 and R "and R"'independently of one another represent a hydrogen atom, a (C 1 -C 4 ) -alkyl group, a (C 2 -C 6) -acyl group, a benzoyl group, an aryl- (C 1 to C 4 ) - alkyl group, an aminoiminomethyl group or a tosyl group,
  • n is 0 or 1 and R is a hydrogen atom, a hydroxy group, a (C 1 -C 4 ) -alkyl group, a (C 1 -C 4 ) -alkoxy group, an aryl- (C 1 to C 4 ) -alkyl group, an acetyloxy group, a benzoyloxy group, a triflyloxy group or a tosyloxy group.
  • R 'represented by formula (II) represents a hydrogen atom, a methyl group, an ethyl group, an iso-propyl group, an n-propyl group, an allyl group, a benzyl group or a phenyl group.
  • R 'represented by the formula (III) represents a hydrogen atom, a methyl group, an ethyl group, an iso-propyl group, a benzyl group, a benzoyloxy group or a phenyl group.
  • R 'represented by the formula (IV) represents a hydrogen atom, a methyl group, an ethyl group, an iso-propyl group, a benzyl group, a benzoyloxy group or a phenyl group.
  • R "and R"'according to formula (V) independently of one another represent a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an iso Propyl group, a benzyl group, a benzoyl group, acetyl group, a
  • R of the formula (VI) is a hydrogen atom, a hydroxy group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, a tert-butyl group, a phenyl group, a methoxy group, an acetyloxy group, a
  • Tosyloxy a triflyloxy group, a benzyloxy group or a benzoyloxy group.
  • the 2,5-diketopiperazine compounds of the formula (I) have chiral centers at least at the carbon atoms of positions 3 and 6 of the 2,5-diketopiperazine ring.
  • the numbering of ring positions 3 and 6 was exemplified in formula (l-b).
  • the 2,5-diketopiperazine compound of the formula (I) of the inventive compositions is preferably based on the stereochemistry of the carbon atoms at 3- and 6-position of the 2,5-Diketopiperazinringes the configuration isomer 3S, 6S, 3R, 6S, 3S, 6R , 3R, 6R or mixtures thereof, more preferably 3S, 6S.
  • compositions according to the invention contain at least one
  • 2,5-diketopiperazine compound of the formula (I) selected from 3-benzyl-6-carboxyethyl-2,5-diketopiperazine (also: 3- (5-benzyl-3,6-dioxopiperazin-2-yl) propanoic acid), 3 Benzyl-6-carboxymethyl-2,5-diketopiperazine, 3-benzyl-6- (p -hydroxybenzyl) -2,5-diketopiperazine, 3-benzyl-6-isopropyl-2,5-diketopiperazine, 3-benzyl 6- (4-Aminobutyl) -2,5-diketopiperazine, 3,6-di (benzyl) -2,5-diketopiperazine, 3,6-di (p -hydroxybenzyl) -2,5-diketopiperazine, 3,6- Di (p- (benzyloxy) benzyl) -2,5-diketopiperazine, 3-benzyl-6-
  • compositions of the invention preferably contain at least one 2,5-diketopiperazine compound of formula (I) selected from 3-benzyl-6-methylpiperazine-2,5-dione, 3- (4-aminobutyl) -6-benzylpiperazine-2 , 5-dione, 3- (1 H -imidazol-4-yl) methyl) -6-benzyl-piperazine-2,5-dione, benzyl 3- (5-benzyl-3,6-dioxopiperazin-2-yl) -propanoate or mixtures it.
  • 2,5-diketopiperazine compound of formula (I) selected from 3-benzyl-6-methylpiperazine-2,5-dione, 3- (4-aminobutyl) -6-benzylpiperazine-2 , 5-dione, 3- (1 H -imidazol-4-yl) methyl) -6-benzyl-piperazine-2,5-dione, benzyl 3- (5-benzy
  • the surfactant composition according to the invention contains a total amount of from 0.1 to 70% by weight of at least one surfactant. It is inventively preferred if the
  • Surfactant composition based on their total weight, a total amount of 5 to 70% by weight, preferably from 10 to 65 wt .-%, particularly preferably from 12 to 60 wt .-%, most preferably from 15 to 60 wt .-%, most preferably from 20 to 55 wt .-%, containing at least one surfactant.
  • the following total amount of total surfactants of the inventive surfactant composition are also particularly preferred:
  • the surfactant composition of the invention preferably contains at least one anionic surfactant.
  • the anionic surfactant is selected from the group consisting of Cs -is-alkylbenzenesulfonates, Cs -is-olefinsulfonates, C 12-18 -alkanesulfonates, Cs-is-ester sulfonates, Cs -is-alkyl sulfates, Cs-is-alkenyl sulfates , Fatty alcohol ether sulfates and
  • the anionic surfactant is selected from at least one Cs-18-alkylbenzenesulfonate.
  • the surfactant composition contains at least one anionic surfactant of the formula (T1)
  • R 1 is a linear or branched, substituted or unsubstituted radical selected from Cs -is-alkyl, aryl or Cs -is-alkylaryl radicals and the grouping -A- for a chemical bond or a radical - (OZ) n -O - stands, wherein OZ is an ethylene oxide (EO) or propylene oxide (PO) grouping and n is an integer from 1 to 50, preferably from 1 to 20 and in particular from 2 to 10, very particularly preferably 2, 3, 4, 5, 6, 7 or 8,
  • Y + is a monovalent cation or the nth part of an n-valent cation.
  • Surfactant composition comprises at least one such surfactant of the above formula (I) in which A of the formula (T 1) for the structural unit is - (OZ) n -O-, where OZ is an ethylene oxide (EO) or propylene oxide (PO) Grouping and n is an integer from 1 to 50, preferably from 1 to 20 and in particular from 2 to 10, very particularly preferably 2, 3, 4, 5, 6, 7 or 8, and R 1 according to formula (T1 ) for a linear or branched, substituted or
  • R 1 is a linear or branched, substituted or unsubstituted alkyl radical, preferably a linear, unsubstituted alkyl radical, more preferably a fatty alcohol radical.
  • Preferred radicals R 1 are selected from decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl radicals and mixtures thereof, where the representatives with even number of carbon atoms Atoms are preferred.
  • radicals R 1 are derived from C 12-18 -fatty alcohols, for example coconut fatty alcohol, tallow fatty alcohol, lauryl, myristyl, cetyl or stearyl alcohol or C 10 -cis-oxo alcohols.
  • Y + is defined as before in formula (T 1).
  • OZ is according to formula (T 1 - 1) an ethylene oxide (EO) or propylene oxide (PO) grouping, preferably an ethylene oxide group.
  • the index n is according to formula (1-1) an integer from 1 to 50, preferably from 1 to 20 and in particular from 2 to 10. Most preferably, n stands for the numbers 2, 3, 4, 5, 6, 7 or 8.
  • Y + is according to formula (T 1 - 1) a monovalent cation or the n-th part of an n-valent cation, preferred are the alkali metal ions and including Na + or K + , with Na + being extremely preferred ,
  • Other cations Y + may be selected from NH 4 + , 1 Zn 2+ , 1 Mg 2+ , 1 Ca 2+ , 1 Mn 2+ , and mixtures thereof.
  • Detergents or cleaning agents may contain as the compound of the formula (I) or as the compound of the formula (T 1 -1) at least one alkyl ether sulfate selected from fatty alcohol ether sulfates of the formula (T1-2)
  • Degree of ethoxylation represents a statistical average that may be an integer or a fractional number for a particular product.
  • the indicated degrees of alkoxylation represent statistical averages, which may be an integer or a fractional number for a particular product.
  • Preferred alkoxylates / ethoxylates have a narrow homolog distribution (narrow rank ethoxylates, NRE).
  • Surfactant compositions as anionic surfactant of formula (T1) at least one compound of formula (T1-3)
  • T1 formula (T1):
  • the detergents or cleaners according to the invention preferably contain as surfactant of the formula (T 1) a combination of
  • At least one fatty alcohol ether sulfate of the formula (T 1 -1) at least one fatty alcohol ether sulfate of the formula (T 1 -1)
  • R 1 is a linear or branched (C 8 -C 18) -alkyl radical
  • OZ stands for an ethylene oxide (EO) or a propylene oxide (PO) grouping
  • n is an integer from 1 to 50, preferably from 1 to 20 and especially from 2 to 10, and
  • Y * + represents a monovalent cation or the nth part of an n-valent cation
  • T1-3 in which R ' and R " together contain 9 to 19, preferably 11 to 15 and in particular 11 to 13 C atoms and Y + is a monovalent cation or the n-th part of an n-valent cation (especially for Na + ).
  • the liquid washing or cleaning agent may also contain soaps as anionic surfactant.
  • soaps as anionic surfactant.
  • Suitable are saturated and unsaturated fatty acid soaps, such as the salts of lauric acid, myristic acid, palmitic acid, stearic acid, (hydrogenated) erucic acid and behenic acid and, in particular, soap mixtures derived from natural fatty acids, for example coconut, palm kernel, olive oil or tallow fatty acids.
  • anionic surfactant when the surfactant composition of the present invention contains anionic surfactant, it is again preferable that, based on the total weight of the composition, anionic surfactant is contained in a total amount of 6 to 70% by weight, more preferably 10 to 50% by weight, more preferably 15 to 40% by weight .-%, is included.
  • the surfactant composition according to the invention may contain as surfactant preferably at least one nonionic surfactant.
  • the surfactant composition according to the invention additionally contains at least one nonionic surfactant in addition to at least one anionic surfactant.
  • Suitable additional nonionic surfactants include alkoxylated fatty acid alkyl esters, alkoxylated fatty acid amides, hydroxylated
  • Alkyl glycol ethers polyhydroxy fatty acid amides, alkylphenol polyglycol ethers, amine oxides,
  • the agent according to the invention particularly preferably contains as nonionic surfactant at least one compound of the formula (T2)
  • R 2 is a linear or branched Cs-C-is-alkyl radical, an aryl radical or alkylaryl radical,
  • XO independently represent an ethylene oxide (EO) or propylene oxide (PO) moiety
  • m represents integers of 1 to 50.
  • radicals R 2 of the formula (T2) are derived from C 12-18 fatty alcohols, for example coconut fatty alcohol, tallow fatty alcohol, lauryl, myristyl, cetyl or stearyl alcohol or C 1 -C 8 oxo alcohols.
  • XO is preferably an ethylene oxide group according to formula (T2).
  • the index m is according to formula (T2) preferably for a number from 1 to 20 and in particular from 2 to 10. Very particularly preferably m stands for the numbers 2, 3, 4, 5, 6, 7 or 8.
  • the nonionic surfactant used are preferably alkoxylated, advantageously ethoxylated, in particular primary, alcohols having preferably 8 to 18 carbon atoms and on average 4 to 12 moles of ethylene oxide (EO) per mole of alcohol, in which the alcohol radical may be linear or preferably methyl-branched in the 2-position or linear and methyl-branched radicals in the mixture can contain, as they are usually present in Oxoalkoholresten.
  • alcohol ethoxylates with linear radicals of alcohols of native origin having 12 to 18 carbon atoms, for example coconut, palm, tallow or oleyl alcohol, and on average 4 to 8 EO per mole of alcohol are preferred.
  • the preferred ethoxylated alcohols include, for example, C12-14-alcohols with 4 EO or 7 EO, C9-n-alcohol with 7 EO, Ci3-i5-alcohols with 5 EO, 7 EO or 8 EO, Ci2-i8-alcohols with 5 EO or 7 EO and mixtures of these.
  • Preferred alcohol ethoxylates have a narrow homolog distribution (narrow rank ethoxylates, NRE).
  • fatty alcohols containing more than 12 EO can also be used. Examples include tallow fatty alcohol with 14 EO, 25 EO, 30 EO or 40 EO.
  • Nonionic surfactants containing EO and PO groups together in the molecule can also be used according to the invention. Also suitable are also a mixture of a (more) branched ethoxylated fatty alcohol and an unbranched ethoxylated fatty alcohol, such as a mixture of a Ci6-i8-fatty alcohol with 7 EO and 2-propylheptanol with 7 EO.
  • the surfactant composition according to the invention particularly preferably contains a C12-18 fatty alcohol with 7 EO or a C5-oxoalcohol with 7 EO as nonionic surfactant.
  • amine oxide in principle all amine oxides established for this purpose in the prior art are compounds which have the formula R 1 R 2 R 3 NO, where each of R 1 , R 2 and R 3 independently of the others is an optionally substituted C 1 -C 30 hydrocarbon chain is, usable.
  • Particularly preferred amine oxides used are those in which R 1 is C 12 -C 18 alkyl and R 2 and R 3 are each independently C 1 -C 4 -alkyl, in particular C 12 -C 18 -alkyldimethylamine oxides.
  • Suitable amine oxides are N-cocoalkyl-N, N-dimethylamine oxide, N-tallowalkyl-N, N-dihydroxyethylamine oxide, myristyl / cetyldimethylamine oxide or lauryldimethylamine oxide.
  • the surfactant compositions according to the invention based on the total weight of nonionic surfactant in a total amount between 0 and 35 wt .-% and preferably from 5 to 30 wt .-%, most preferably from 7 to 28% by weight, respectively based on the total mean.
  • the surfactant composition according to the invention contains water as a further obligatory constituent.
  • Particularly preferred liquid detergents contain - based on their weight - water in a total amount of 5 to 90 wt .-%, preferably 10 to 85 wt .-%, particularly preferably 25 to 75 wt .-% and in particular 35 to 65 wt. %.
  • the detergents may be low-water detergents, the total amount of water in a preferred embodiment being between 0 and 25% by weight, in particular between 1 and 20% by weight and particularly preferably between 2 and 18% by weight. , in each case based on the total liquid surfactant composition.
  • the yield strength of the surfactant compositions according to the invention is in the range from 0.01 to 60 Pa, preferably from 0.1 to 30 Pa, more preferably from 1 to 15 Pa (rotational rheometer from TA Instruments, type AR G2, 20 ° C).
  • nonaqueous solvents may additionally be added to the surfactant composition according to the invention.
  • Preferred surfactant compositions in this context are characterized in that they additionally comprise at least one organic solvent having at least one hydroxyl group, without amino group and having a molecular weight of at most 500 g / mol (preferably selected from (C 2 -C 5) -alkanols having at least one hydroxyl group ( particularly preferably ethanol, ethylene glycol, 1,2-propanediol, glycerol, 1,3-propanediol, n-propanol, isopropanol, 1,1,1-trimethylolpropane, 2-methyl-1,3-propanediol, 2-hydroxymethyl-1, 3-propanediol), triethylene glycol, butyl diglycol, polyethylene glycols having a weight-average molecular weight M w of at most 500 g / mol, glycerol carbonate, propylene carbonate, 1-me
  • the surfactant composition contains a (C 2 -C 6) -alcohol having at least one hydroxyl group (in particular ethanol and / or glycerol) in amounts of between 0.5 and 5% by weight, based on the total composition.
  • the surfactant composition according to the invention additionally contains suspended solid particles (also referred to below as particles).
  • Solid particles suspended as such are solid substances which do not dissolve in the liquid phase of the surfactant composition according to the invention at 20 ° C. and are present as a separate phase.
  • the particles are preferably selected from polymers, pearlescent pigments, microcapsules, speckles or mixtures thereof.
  • microcapsules include any type of capsule known to those skilled in the art, but in particular core-shell capsules and matrix capsules.
  • Matrix capsules are porous shaped bodies that have a structure similar to a sponge.
  • Core-shell capsules are shaped bodies having a core and a shell.
  • Suitable microcapsules are those capsules which have an average diameter Xso, 3 (volume average) of from 0.1 to 200 ⁇ m, preferably from 1 to 100 ⁇ m, more preferably from 5 to 80 ⁇ m, particularly preferably from 10 to 50 ⁇ m and in particular from 15 to 40 pm.
  • the mean particle size diameter X 50.3 is determined by sieving or by means of a particle size analyzer Camsizer from Retsch.
  • microcapsules of the invention preferably contain at least one active ingredient, preferably at least one perfume. These preferred microcapsules are perfume microcapsules.
  • the microcapsules have a semipermeable capsule wall (shell).
  • a semipermeable capsule wall is a capsule wall which is semipermeable, ie it releases small quantities of the capsule core continuously over time, without the capsule having to be filled, for example. was damaged or opened by friction. Such capsules continuously continue to set small amounts of the capsule drug, e.g. Perfume, free.
  • the microcapsules have an impermeable shell.
  • An impermeable shell in the sense of the present invention is a capsule wall which is essentially impermeable, ie the capsular core only by damage or opening of the capsule releases.
  • Such capsules contain significant amounts of the at least one perfume in the capsule core, so that a very intense fragrance is provided when damaged or when the capsule is opened.
  • the resulting scent intensities are usually so high that lower amounts of the microcapsules can be used to achieve the same scent intensity as conventional microcapsules.
  • Microcapsules with impermeable shell Through the use of both capsule types, a significantly improved fragrance intensity can be provided over the entire laundry cycle.
  • composition according to the invention may also contain two or more different microcapsule types with semipermeable or impermeable shell.
  • materials for the shell of the microcapsules are usually high molecular weight
  • Epoxy resins and others Preferably serves as a wall material, ie as a shell, melamine-formaldehyde polymer, melamine-urea polymer, melamine-urea-formaldehyde polymer, polyacrylate polymer or polyacrylate copolymer.
  • a wall material ie as a shell, melamine-formaldehyde polymer, melamine-urea polymer, melamine-urea-formaldehyde polymer, polyacrylate polymer or polyacrylate copolymer.
  • Preferred melamine-formaldehyde microcapsules are prepared in which melamine-formaldehyde precondensates and / or their C 1 -C 4 -alkyl ethers in water in which the at least one odor modulator compound and optionally further ingredients, such as at least one
  • Suitable protective colloids are, for example, cellulose derivatives, such as hydroxyethylcellulose, carboxymethylcellulose and methylcellulose, polyvinylpyrrolidone, copolymers of N-vinylpyrrolidone, polyvinyl alcohols, partially hydrolyzed polyvinyl acetates, gelatin, gum arabic, xanthan gum, alginates, pectins, degraded starches, casein, polyacrylic acid, polymethacrylic acid, copolymers of acrylic acid and methacrylic acid, sulfonic acid-containing water-soluble polymers containing sulfoethyl acrylate, sulfoethyl methacrylate or sulfopropyl methacrylate, and polymers of N- (sulfoethyl) -maleimide, 2-acrylamido-2-alkylsulfonic acids, styre
  • At least one cationic polymer of polyquaternium-1, polyquaternium-2, polyquaternium-4, polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-8, polyquaternium-9, polyquaternium-10 is suitable as cationic polymer for coating the microcapsules , Polyquaternium-1, Polyquaternium-12, Polyquaternium-13, Polyquaternium-14, Polyquaternium-15, Polyquaternium-16, Polyquaternium-17, Polyquaternium-18, Polyquaternium-19, Polyquaternium-20,
  • Polyquaternium-86th Very particular preference is given to polyquaternium-7.
  • the polyquaternium nomenclature of the cationic polymers used in the context of this application is taken from the declaration of cationic polymers according to the International Nomenclature of Cosmetic Ingredients (INCI Declaration) of cosmetic raw materials.
  • Preferably usable microcapsules have average diameters Xso, 3 in the range of 1 to 100 pm, preferably from 5 to 95 pm, in particular from 10 to 90 pm, for example from 10 to 80 pm.
  • the shell of the microcapsules surrounding the core or (filled) cavity preferably has an average thickness in the range from about 5 to 500 nm, preferably from about 50 nm to 200 nm, in particular from about 70 nm to about 180 nm.
  • Pearlescent pigments are pigments that have a pearlescent shine. Pearlescent pigments consist of thin leaflets that have a high refractive index and partially reflect the light and are partially transparent to the light. The nacreous gloss is produced by interference of the light striking the pigment (interference pigment). Pearlescent pigments are usually thin flakes of the above material, or contain the o.g. Material as thin multilayer films or as parallel arranged components in a suitable carrier material.
  • the pearlescent pigments which can be used according to the invention are either natural
  • Pearlescent pigments such as e.g. Fischsilber (guanine / hypoxanthine mixed crystals from fish scales) or mother of pearl (from ground mussel shells), monocrystalline flake-shaped
  • Pearlescent pigments such as bismuth oxychloride as well as pearlescent pigments based on mica and mica / metal oxide.
  • the latter pearlescent pigments are mica, which have been provided with a metal oxide coating.
  • Mica-based and mica / metal oxide-based pearlescent pigments are preferred according to the invention.
  • Mica belongs to the layer silicates. The most important representatives of these silicates are muscovite, phlogopite, paragonite, biotite, lepidolite and margarite. For the production of
  • Suitable metal oxides Cr 2 Ü3 and Fe include T1O2, 2 03.
  • interference pigments as well as color luster pigments according to the invention obtained as pearlescent pigments.
  • these pearlescent pigment types also have color effects.
  • the pearlescent pigments which can be used according to the invention can furthermore contain a color pigment which does not derive from a metal oxide.
  • the grain size of the pearlescent pigments preferably used is preferably at a mean diameter Xso, 3 (volume average) between 1 .0 and 100 .mu.m, more preferably between 10.0 and 60.0 pm.
  • speckles are macroparticles, in particular macrocapsules, which have an average diameter Xso, 3 (volume average) of more than 300 ⁇ m, in particular from 300 to 1500 ⁇ m, preferably from 400 to 1000 ⁇ m.
  • Speckles are preferably matrix capsules.
  • the matrix is preferably colored. Matrix formation occurs, for example, via gelation, polyanion-polycation interactions, or polyelectrolyte-metal ion interactions, and is well known in the art as well as the production of particles with these matrix-forming materials.
  • An exemplary matrix-forming material is alginate.
  • alginate-based speckles is an aqueous alginate solution, which if necessary, in addition to the entrapped drug or the
  • the surfactant compositions according to the invention may additionally contain further ingredients which have the performance and / or aesthetic properties of
  • compositions according to the intended use further improve.
  • the compositions according to the invention especially if they are suitable as textile treatment agents (for example as detergents or softeners), builders, bleaches, bleach activators, bleach catalysts, esterquats, silicone oils,
  • Emulsifiers thickeners, electrolytes, pH adjusters, fluorescers, dyes, hydrotopes, foam inhibitors, anti redeposition agents, solvents, enzymes, optical brighteners, Antiredeposition agents, anti-shrinkage agents, anti-wrinkling agents, color transfer inhibitors, colorants, wetting agents, antimicrobials, germicides, fungicides, antioxidants, corrosion inhibitors, preservatives, antistatic agents, ironing aids, repellents and impregnating agents, polymers, swelling and anti-slip agents and UV absorbers.
  • Surfactant composition preferably contains at least one water-soluble, organic and / or water-soluble, inorganic builder. To the water-soluble organic
  • Builder substances include polycarboxylic acids, in particular citric acid, adipic acid, succinic acid, glutaric acid, malic acid, tartaric acid, maleic acid, fumaric acid and sugar acids, monomeric and polymeric aminopolycarboxylic acids, in particular methylglycinediacetic acid, nitrilotriacetic acid and ethylenediaminetetraacetic acid and polyaspartic acid,
  • Polyphosphonic acids in particular aminotris (methylenephosphonic acid),
  • Suitable, although less preferred, compounds of this class are copolymers of acrylic or methacrylic acid with vinyl ethers, such as vinylmethyl ethers, vinyl esters, ethylene, propylene and styrene, in which the acid content is at least 50% by weight.
  • the organic builder substances can be used, in particular for the preparation of liquid textile treatment or cleaning agents, in the form of aqueous solutions, preferably in the form of 30 to 50 percent by weight aqueous solutions. All of the acids mentioned are generally used in the form of their water-soluble salts, in particular their alkali metal salts.
  • Preferred salts are the salts of polycarboxylic acids such as citric acid, adipic acid,
  • Succinic acid glutaric acid, tartaric acid, sugar acids and mixtures thereof.
  • Organic builders may, if desired, be included in amounts of up to 40% by weight, more preferably up to 25% by weight, and preferably from 1% to 8% by weight. Quantities close to the stated upper limit are preferably used in paste-form or liquid, in particular hydrous, compositions according to the invention.
  • Aftertreatment agents such as e.g. Softener, may optionally also be free of organic builder.
  • Composition preferably contains at least one enzyme.
  • Suitable enzymes include those from the class of proteases, cutinases, amylases, pullulanases, hemicellulases, cellulases, lipases, oxidases and peroxidases and mixtures thereof. Particularly suitable are fungi or bacteria such as Bacillus subtilis, Bacillus licheniformis, Streptomyces Griseus, Humicola lanuginosa, Humicola insolens, Pseudomonas pseudoalcaligenes or Pseudomonas cepacia derived enzymatic agents.
  • the optionally used enzymes may be adsorbed to carriers and / or embedded in encapsulants to protect against premature inactivation. They are, if desired, in the compositions preferably in amounts not exceeding 5 wt .-%, in particular from 0.2 wt .-% to 2 wt .-%, contained.
  • An optical brightener is preferably stilbenedisulfonic acids from the substance classes of distyrylbiphenyls, the stilbenes, the 4,4 'diamino-2,2', coumarins, the dihydroquinolinones, the 1, 3-diaryl pyrazolines, naphthalimides of the benzoxazole systems, benzisoxazole systems, benzimidazole systems, heterocyclic substituted pyrene derivatives, and mixtures thereof.
  • optical brighteners include disodium 4,4'-bis (2-morpholino-4-anilino-s-triazin-6-ylamino) stilbene disulfonate (available, for example, as Tinopal® DMS from BASF SE), disodium 2,2 '.
  • compositions according to the invention which are suitable as textile treatment or cleaning compositions may also contain components which have a positive influence on the oil and grease washability from textiles, so-called soil release active ingredients. This effect becomes particularly clear when a textile is soiled, which has been previously washed several times with an agent containing this oil and fat dissolving component.
  • nonionic cellulose ethers such as methylcellulose and methylhydroxypropylcellulose with a proportion of methoxyl groups of 15 to 30% by weight and of hydroxypropoxyl groups of 1 to 15% by weight, based in each case on the nonionic cellulose ethers, as well as the known from the prior art polymers of phthalic acid and / or terephthalic acid or derivatives thereof with monomeric and / or polymeric diols, in particular polymers of ethylene terephthalates and / or
  • Polyethylene glycol terephthalates or anionic and / or nonionic modified derivatives of these are preferred.
  • the textile treatment or cleaning agents may also color transfer inhibitors, preferably in amounts of 0.1 wt .-% to 2 wt .-%, in particular 0.1 wt .-% to 1 wt .-%, containing, in a preferred embodiment of the invention polymers of vinylpyrrolidone , Vinylimidazole, vinylpyridine N-oxide or copolymers thereof.
  • Graying inhibitors have the task of keeping suspended from the textile fiber dirt suspended in the fleet.
  • Water-soluble colloids of mostly organic nature are suitable for this purpose, for example starch, glue, gelatin, salts of ether carboxylic acids or ether sulfonic acids of starch or of cellulose or salts of acidic sulfuric acid esters of cellulose or starch.
  • water-soluble polyamides containing acidic groups are suitable for this purpose.
  • starch derivatives can be used, for example aldehyde starches.
  • the dye transfer inhibitor is a polymer or copolymer of cyclic amines such as vinylpyrrolidone and / or vinylimidazole.
  • Color transfer inhibiting polymers include polyvinylpyrrolidone (PVP),
  • Polyvinylimidazole (PVI), copolymers of vinylpyrrolidone and vinylimidazole (PVP / PVI),
  • polyvinylpyrrolidone PVP
  • polyvinylimidazole PVI
  • copolymers of vinylpyrrolidone and vinylimidazole PVP / PVI
  • the polyvinylpyrrolidones (PVP) used preferably have an average molecular weight of 2,500 to 400,000 and are commercially available from ISP Chemicals as PVP K 15, PVP K 30, PVP K 60 or PVP K 90 or from BASF as Sokalan® HP 50 or Sokalan® HP 53 available.
  • the copolymers of vinylpyrrolidone and vinylimidazole (PVP / PVI) used preferably have a molecular weight in the range from 5,000 to 100,000.
  • PVP / PVI copolymer for example, from BASF under the name Sokalan® HP 56.
  • Another extremely preferred color transfer inhibitor are polyethylene glycol-modified copolymers of vinylpyrrolidone and vinylimidazole, which are available, for example, under the name Sokalan® HP 66 from BASF are.
  • liquid compositions according to the invention may be present in pre-portioned form, the composition according to the invention being filled into a water-soluble casing and thus being able to form part of a water-soluble packaging. If the composition according to the invention is packaged in a water-soluble casing, it is preferred that the content of water is between 5 and 20% by weight, based on the total agent, and that anionic surfactants, if present, in the form of their
  • Ammonium salts are present.
  • the present invention relates to the use of at least one said DKP compound of the formula (I) (vide supra) for the preparation of liquid, aqueous surfactant compositions, in particular washing or cleaning agents, with
  • the present invention relates to the use of a said surfactant composition as a continuous phase to provide a suspension.
  • the invention is directed to a process for substrate treatment comprising the process steps
  • Preferred methods are those in which the substrate is a fabric.
  • step (b) the substrate is in contact with the aqueous liquor prepared according to (a) for 10 to 240 minutes, in particular 20 to 180 minutes.
  • the substrate is rinsed and dried after step (b).
  • step (a) the substrate is placed in the drum of the washing machine.
  • the surfactant composition of the first subject of the invention is disclosed in U.S. Pat.
  • temperatures of 60 ° C or less for example 50 ° C or less, are employed. These temperature data refer to the temperatures used in step (b).
  • Another subject of the invention relates to a process for producing a liquid
  • a flow-limit surfactant composition characterized in that first a liquid composition containing at least one 2,5-diketopiperazine compound of the formula (I),
  • R 1 to R 5 are defined as described in the first subject of the invention, in the presence of water and 0.1 to 70 wt .-% of surfactant and optionally optional additives at a temperature above the sol-gel transition temperature of the liquid
  • Composition is cooled below the sol-gel transition temperature.
  • the surfactant composition can also be first preheated to said temperature without the DKP compound of the formula (I) and cooled after addition of the DKP compound of the formula (I).
  • a liquid premix containing water and based on the weight of said liquid surfactant composition 0.1 to 70 wt .-% of surfactant and optionally optional additives to a temperature of 10 to 150 ° C is brought and at least one 2,5-diketopiperazine compound of the formula (I) is added.
  • a liquid first premix containing at least one liquid and optionally surfactant and optionally optional additives is brought to a temperature of 50 to 150 ° C and at least one 2,5-diketopiperazine compound of the formula (I) is added and dissolved with stirring, and then this still tempered liquid first premix in a at a temperature of 10 to 35 ° C located second premix containing water and surfactant is mixed.
  • anionic surfactants can initially be presented in their acid form in an aqueous medium, and then the pH is increased by addition of alkalizing agents (preferably alkanolamines, such as monoethanolamine) to release neutralization heat and the anionic surfactants are converted into the salt form ,
  • alkalizing agents preferably alkanolamines, such as monoethanolamine
  • the resulting heat of neutralization is preferably used to increase the temperature for heating the system via the sol-gel transition temperature.
  • Preferred processes are thus characterized by the fact that the heat released when the pH is increased is used to increase the temperature.
  • the sol-gel transition temperature can be determined in advance by known methods.
  • this can be done via a rheological measurement with oscillating deformation constant frequency as a function of temperature.
  • a measurement is at a
  • R 1 , R 2 , R 3 and R 4 independently represent a hydrogen atom, a
  • R 5 represents a hydrogen atom, a linear (C 1 to C 6) alkyl group, a branched (C 3 to Cio) alkyl group, a (C 3 to C 6) cycloalkyl group, a (C 2 to C 6) alkenyl group, a (C 2 to C 6 ) Alkynyl group, a (C 1 -C 4 ) -hydroxyalkyl group, a (C 1 -C 4 ) -alkoxy (C 1 -C 4 ) -alkyl group, a (C 1 -C 4 ) -acyloxy- (C 1 -C 4 ) - alkyl group, one Aryloxy- (C 1 -C 4 ) -alkyl group, a 0- (aryl- (C 1 -C 4 ) -alkyl) oxy- (C 1 -C 4 ) -alkyl group, a (C 1 -C 4 ) -alkyls
  • Aminocarbonyl- (C 1 -C 4) -alkyl group an N- (C 1 -C 4 ) -alkylaminocarbonyl- (C 1 -C 4 ) -alkyl group, an N, N-di (C 1 -C 4 ) -alkyl) aminocarbonyl- (C 1 -C 4 ) -alkyl group; C 4 ) alkyl group, an N- (C 2 -C 8) -acylaminocarbonyl (C 1 -C 4 ) -alkyl group, an N, N- (C 2 -C 8) -diacylaminocarbonyl- (C 1 -C 4 ) -alkyl group, an N- (C 2 -C 8) -Acyl-N- (C 1 -C 4 ) -alkylaminocarbonyl- (C 1 -C 4 ) -alkyl group, an N- (aryl- (C
  • composition according to item 1 characterized in that based on the
  • a composition according to item 1 or 2 characterized in that according to formula (I) R 1 binds in the para position of the phenyl ring and preferably R 2 to R 4 are hydrogen.
  • the radicals R 1 , R 2 , R 3 and R 4 independently of one another represent a hydrogen atom, a hydroxy group, a methyl group, an ethyl group, an iso-propyl group, an n-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a benzyl group, a Methoxy group, a (C 2 -C 6) acyloxy group, an aryloxy group, a tosyloxy group, a triflyloxy group, a benzyloxy group or a benzoyloxy group.
  • the radicals R 1 , R 2 , R 3 and R 4 independently of one another represent a hydrogen atom, a hydroxy group, a methyl group, an ethyl group, an iso-propyl group, an n-propyl group, an
  • R 5 represents a hydrogen atom, a methyl group, an isopropyl group, an iso-butyl group, a tert-butyl group, a 2- (methylsulfanyl) ethyl group, a
  • R ' is a hydrogen atom, a (C 1 to C 4 ) -alkyl group, a (C 2 to C 4 ) -alkenyl group, an aryl group or an aryl- (C 1 to C 4 ) -alkyl group,
  • R ' is a hydrogen atom, a (C 1 to C 4 ) -alkyl group, a (C 2 to C 4 ) -alkenyl group, an aryl group or an aryl- (C 1 to C 4 ) -alkyl group,
  • n 0 or 1
  • X is an oxygen atom or a group -NH- and R "is a hydrogen atom, a (Ci-C 4 ) alkyl group, a (C2 to C 4 ) alkenyl group, an aryl group or an aryl- (C 1 to C 4 ) -alkyl group,
  • n 1 or 2 and R "and R"'independently of one another represent a hydrogen atom, a (C 1 -C 4 ) -alkyl group, a (C 2 -C 6) -acyl group, a benzoyl group, an aryl- (C 1 to C 4 ) alkyl group, an aminoiminomethyl group or a tosyl group,
  • n is 0 or 1 and R is a hydrogen atom, a hydroxy group, a (C 1 -C 4 ) -alkyl group, a (C 1 -C 4 ) -alkoxy group, an aryl- (C 1 to C 4 ) -alkyl group, a
  • Acetyloxy group, a benzoyloxy group, a triflyloxy group or a tosyloxy group Composition according to item 5, characterized in that R 'according to formula (II) represents a hydrogen atom, a methyl group, an ethyl group, an iso-propyl group, an n-propyl group, an allyl group, a benzyl group or a phenyl group.
  • Composition according to one of the items 5 to 8 characterized in that R "and R" 'according to formula (V) independently of one another represent a hydrogen atom, a
  • Methyl group an ethyl group, an n-propyl group, an iso-propyl group, a
  • R according to formula (VI) is a hydrogen atom, a hydroxy group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a Methoxy group, an acetyloxy group, a tosyloxy group, a triflyloxy group, a benzyloxy group or a benzoyloxy group.
  • composition according to one of the preceding points, characterized in that the 2,5-diketopiperazine compound of the formula (I) relates to the stereochemistry of the carbon atoms at the 3- and 6-positions of the 2,5-diketopiperazine ring
  • composition according to one of the preceding points characterized in that it contains at least one anionic surfactant.
  • Composition according to one of the preceding points characterized in that at least one anionic surfactant selected from the group consisting of Cs -is-alkylbenzenesulfonates, Cs -is-olefinsulfonates, C 12-18 -alkanesulfonates, Cs -is-ester sulfonates, Cs-isomers Alkyl sulfates, Cs-is-alkenyl sulfates, fatty alcohol ether sulfates and mixtures thereof.
  • Composition according to one of the preceding points characterized in that as surfactant at least one compound of the formula (T1-3) is contained,
  • T1-3 in the R ' and R "are independently H or alkyl and together contain 9 to 19, preferably 9 to 15 and especially 9 to 13 C atoms, and Y + is a monovalent cation or the nth part of an N-valent cation (especially Na +) mean.
  • a composition according to any of the preceding points characterized in that they contain at least one nonionic surfactant.
  • R 2 is a linear or branched Cs-C-is-alkyl radical, an aryl radical or alkylaryl radical,
  • XO independently of one another for an ethylene oxide (EO) or propylene oxide (PO)
  • composition according to one of the preceding points characterized in that surfactant in a total amount of 5 to 70 wt .-%, preferably from 10 to 65 wt .-%, particularly preferably from 12 to 60 wt .-%, most preferably from 15 to 60% by weight, most preferably from 20 to 55% by weight.
  • surfactant in a total amount of 5 to 70 wt .-%, preferably from 10 to 65 wt .-%, particularly preferably from 12 to 60 wt .-%, most preferably from 15 to 60% by weight, most preferably from 20 to 55% by weight.
  • Composition according to one of the preceding claims characterized in that water in a total amount of 5 to 90 wt .-%, preferably 10 to 85 wt .-%, particularly preferably 25 to 75 wt .-% and in particular 35 to 65 parts by weight. %, is included.
  • composition according to one of the preceding points characterized in that water is contained in a total amount of between 1 and 20% by weight, preferably between 2 and 18% by weight.
  • Composition according to one of the preceding points characterized in that it additionally contains at least one organic solvent with at least one hydroxy group, without amino group and with a molecular weight of at most 500 g / mol (preferably selected from (C2-Cs) -alkanols with at least one hydroxy group
  • composition according to item 21 characterized in that said organic solvent is contained in a total amount of from 0 to 20% by weight, in particular from 0.5 to 20% by weight.
  • composition according to one of the preceding points characterized in that it has a yield point in the range from 0.01 to 60 Pa, preferably from 0.1 to 30 Pa, particularly preferably from 1 to 15 Pa (rotational rheometer from TA-Instruments, Type AR G2, 20 ° C). Composition according to one of the preceding points, characterized in that it additionally contains suspended solid particles.
  • Process for substrate treatment comprising the process steps
  • R 1 to R 5 are as defined in any one of items 1, 3 to 10, in the presence of water and 0, 1 to 70 wt .-% of surfactant and optionally optional additives at a temperature above the sol-gel transition temperature of the liquid Homogenizing the composition, and then the heated liquid
  • Composition is cooled below the sol-gel transition temperature.
  • Process according to item 26 characterized in that, for the preparation of said liquid composition, a liquid premix containing water and 0, 1 to 70 % By weight of surfactant and optionally optional additives is brought to a temperature of 10 to 150 ° C and at least one 2,5-diketopiperazine compound of the formula (I) is added.
  • R 1 and R 5 are defined:
  • IR spectra were measured on a Nicolet Thermo iS10 scientific spectrometer with diamond ATR unit. The absorption bands were reported in cnr 1 with the following relative intensity data: s (strong, 0-33% T); m (medium, 34 - 66% T), w (weak, 67 - 100% T), and br (broad).
  • the dipeptide (1 .0 eq) was dissolved in CH 2 Cl 2 (0.4 M) and cooled down to 0 ° C. TFA (5.0 eq) was added in one portion and stirred until the starting material had reacted. Meanwhile, the reaction mixture was slowly warmed to 25 ° C. All fleeting
  • TFA salt was isolated as a colorless solid.
  • the TFA salt (1.0 eq) was dissolved in 2-butanol (0.1 M) and AcOH (3.0 eq) and NEt3 (2.0 eq) were added. The mixture was stirred at 80 ° C until complete conversion of the starting material and finally cooled to 25 ° C. The precipitate was filtered off, washed with THF (3c) and dried in a fine vacuum. Finally, the cyclized dipeptide was obtained as a colorless solid.
  • the protected cyclic dipeptide was mixed in MeOH (0.1 M) and palladium on activated carbon (5 mol%) was added. The suspension was saturated with hydrogen and stirred until complete conversion at 25 ° C. After filtration and removal of the solvent under reduced pressure, the deprotected cyclic dipeptide was isolated as a colorless solid.
  • IR (ATR, neat): v 3184 (w), 3033 (w), 2979 (w), 2889 (w), 1663 (s), 1484 (m), 1466 (s), 1455 (s), 1371 (w), 1338 (s), 1242 (w), 121 1 (w), 1 191 (w), 1 160 (w), 1 104 (m), 1054 (m), 969 (w), 923 ( w), 856 (s),
  • IR (ATR, neat): v 3535 (w), 3204 (br), 3029 (w), 1653 (s), 1615 (m), 1589 (m), 1516 (s), 1496 (w), 1464 (s), 1331 (m), 1274 (m), 1248 (m), 1224 (m), 1200 (m), 1173 (s), 1101 (m), 1078 (m), 1013 (w), 878 (w), 805 (s), 750 (s), 696 (s), 660 (s) cm -1 .
  • IR (ATR, neat): v 3190 (w), 3060 (w), 2969 (w), 2902 (w), 1732 (m), 1672 (s), 1456 (m), 1436 (m), 1394 (w), 1338 (m), 1260 (m), 1215 (w), 1152 (s), 1102 (m), 1012 (w), 956 (m), 864 (m), 844 (m), 819 (m), 753 (s), 700 (s), 656 (m) cm 1 .
  • IR (ATR, neat): v 3179 (w), 3030 (w), 2881 (w), 2852 (w), 1660 (s), 161 1 (m), 1508 (s), 1463 (s), 1453 (s), 1376 (w), 1340 (m), 1310 (m), 1297 (m), 1237 (s), 1225 (s), 1 174 (s), 1 1 10 (m), 1042 ( m), 1016 (m), 922 (m), 833 (s), 808 (s), 773 (s), 755 (m), 732 (s), 721 (s), 694 (s), 653 ( m) cm 1 .
  • IR (ATR, neat): v 3516 (w), 3145 (w), 1665 (s), 1614 (m), 1598 (m), 1515 (s), 1456 (s), 1378 (w), 1337 (m), 1308 (w), 1272 (m), 1237 (s), 1 173 (m), 1 104 (m), 1085 (w), 1013 (w), 950 (w), 925 (w) , 884 (w), 825 (s), 796 (s), 776 (s), 717 (m) cm 1 .
  • the following framework surfactant composition having yield value was prepared according to Table 1 (vide infra).
  • a range of 2,5-diketopiperazine compounds according to Table 2 (vide infra) in the amount indicated therein was mixed together with the remaining ingredients of F1 as follows.
  • compositions E1 to E4 according to the invention were thus prepared.
  • composition F1 of Table 1 Active substance based on the weight of composition F1 of Table 1
  • compositions E1 to E4 speckles are incorporated stable.

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Abstract

L'invention concerne une composition de tensioactifs liquide à limite d'écoulement, en particulier des détergents, contenant rapporté à son poids total (i) au moins un composé de 2,5-dicétopipérazine de formule (I), dans laquelle R1, R2, R3, R4 et R5 sont tels que définis dans la revendication 1, et (ii) une quantité totale de 0,1 à 70 % en poids d'au moins un tensioactif et (iii) de l'eau, cette composition présentant une stabilité au stockage même en cas d'incorporation de particules solides. De telles compositions de tensioactifs peuvent être utilisées principalement comme compositions de détergents liquides.
PCT/EP2019/051338 2018-02-06 2019-01-21 Composition de détergents à limite d'écoulement WO2019154613A1 (fr)

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DE102018201831.6A DE102018201831A1 (de) 2018-02-06 2018-02-06 Waschmittelzusammensetzung mit Fließgrenze

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DE102018209002A1 (de) 2018-06-07 2019-12-12 Henkel Ag & Co. Kgaa Waschmittelzusammensetzung mit Fließgrenze

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EP2365050A1 (fr) * 2010-03-12 2011-09-14 The Procter & Gamble Company Gélifiant di-amido pour une utilisation dans des compositions de produits de consommation
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JP7475635B2 (ja) 2020-01-30 2024-04-30 公立大学法人大阪 含窒素化合物およびその製造方法、ならびに該含窒素化合物を含む光機能性材料

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EP3749739A1 (fr) 2020-12-16

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