EP3981865A2 - Use of cationically modified polyurethane dispersions as fabric softeners - Google Patents

Abstract

The present invention relates to the use of cationically modified polyurethane dispersions as textile softeners, textile treatment agents containing at least one such cationically modified polyurethane dispersion, and methods for treating textiles using at least one such agent or at least one such cationically modified polyurethane dispersion.

Description

The present invention relates to the use of cationically modified polyurethane dispersions as textile softeners, textile treatment agents containing at least one such cationically modified polyurethane dispersion, and methods for treating textiles using at least one such agent or at least one such cationically modified polyurethane dispersion.

Repeated washing often causes fabrics to become hard and lose their softness. In order to restore the softness/flexibility of textiles, to give them a pleasant fragrance and/or to improve their antistatic properties, the textiles are treated with a fabric softener in a subsequent rinsing process after the actual washing and cleaning process.

Common main active ingredients of such fabric softeners are cationic fabric softening compounds, for example those which have one or two long-chain alkyl groups in a molecule. Widely used cationic fabric softening compounds include, for example, methyl-N-(2-hydroxyethyl)-N,N-di(tallowacyloxyethyl)ammonium compounds, methyl-N-(2-hydroxyethyl)-N,N-di(tallowacyloxyethyl)- ammonium compounds or N,N-dimethyl-N,N-di(tallowacyloxyethyl)ammonium compounds. Esterquats (EQ), the term generally being understood to mean quaternized fatty acid triethanolamine ester salts, are widely suitable for both fiber and hair finishes and have largely eliminated the above quaternary ammonium compounds in recent years due to their better ecotoxicological compatibility market displaced. However, since most esterquats have relatively long fatty acid chains, rapid biodegradability is not always guaranteed. In addition, non-polar side chains can result in an overall reduced affinity for the fibers of the textile to be conditioned.

Accordingly, there remains a need for biodegradable, more polar compounds that are useful in imparting softness to fabrics.

This problem is solved by using cationically modified polyurethane dispersions as textile softeners.

A first object of the present invention is therefore the use of a dispersion of at least one cationically modified polyurethane as a textile softener in textile treatment processes.

In a further aspect, the present invention relates to a textile treatment agent comprising at least one dispersion of at least one cationically modified polyurethane.

In a further aspect, the invention also relates to a method for conditioning textiles, characterized in that at least one dispersion of at least one cationically modified polyurethane and/or at least one textile treatment agent, as defined herein, is used in at least one method step.

These and other aspects, features and advantages of the invention will become apparent to those skilled in the art from a study of the following detailed description and claims. Each feature from one aspect of the invention can be used in any other aspect of the invention.

A textile treatment agent, as described herein, is in particular a fabric softener.

Fabric softeners are added to the laundry in the last rinse cycle of the machine wash in order to prevent the "dry rigidity" effect that occurs when the laundry is drying. The dry rigidity is caused by the formation of hydrogen bonds between the cellulose fibers. The cationic active ingredients in the fabric softener penetrate the fibers or settle on the fiber surface, combine with the negative charges and thus weaken the interactions. Due to the reduced stiffness of the item of laundry, the effort required for ironing is reduced and the wearing comfort is increased.

Accordingly, the agents described herein are particularly suitable for conditioning textile fabrics.

The term "conditioning", in the context of the present invention, denotes the imparting of a desired property, for example, in relation to textiles, a pleasant hand, crease resistance or low static charge.

"At least one" as used herein includes but is not limited to 1, 2, 3, 4, 5, 6 and more. With regard to an ingredient, the information refers to the type of ingredient and not to the absolute number of molecules. "At least one surfactant" thus means, for example, at least one type of surfactant, i.e. one type of surfactant or a mixture of several different surfactants can be meant. Together with weight information, the information refers to all compounds of the type specified that are contained in the composition/mixture, i.e. the composition does not contain any other compounds of this type beyond the specified amount of the corresponding compounds.

All percentages are % by weight unless otherwise specified. Numerical ranges given in the format "from x to y" include the stated values. Where multiple preferred numeric ranges are given in this format, it is understood that any ranges resulting from the combination of the different endpoints are also included.

"About" or "about" as used herein in connection with a numerical value refers to the numerical value ±10%, preferably ±5%.

When reference is made herein to molar masses, this information always relates to the number-average molar mass M _n , unless explicitly stated otherwise. The number average molar mass can be determined, for example, by means of gel permeation chromatography (GPC) in accordance with DIN 55672-1:2007-08 with THF as the eluent. The mass-average molar mass M _w can also be determined by GPC, as described for M _n .

Whenever alkaline earth metals are mentioned below as counterions for monovalent anions, this means that the alkaline earth metal is of course only present in half the amount of substance - sufficient for charge equalization - as the anion.

"Liquid" as used in the context of the present invention means all flowable compositions (at 20°C, 1.013 bar), including gels and paste-like compositions, as well as non-Newtonian liquids that exhibit a yield point.

"Solid" as used herein in the context of the present invention means a powder, granule, extrudate or compact composition.

"Phosphate-free" and "phosphonate-free" as used herein means that the composition in question is essentially free of phosphates or phosphonates, i.e. in particular phosphates or phosphonates in amounts less than 0.1% by weight, preferably less than 0 .01% by weight, based on the respective composition.

A composition according to the invention can be a one-component composition or a multi-component composition. In the context of the present invention, the term “one-component agent” refers to an agent which consists of only a single component. The term "multi-component agent" as used herein, on the other hand, designates an agent which is composed of at least two components. It is preferred that the individual components of a multi-component agent according to the invention are spatially separated from one another.

The term "spatially separated" in relation to the components of the composition, as used herein, means that the individual components cannot come into contact with each other prior to use of the composition. Usually, the agent is provided in a multi-chamber packaging, such as a bottle, tube or pouch, in particular a two-chamber bottle or a two-chamber pouch, with each individual component being located separately from the other component(s) in a separate chamber.

The spatial separation of individual components of the agent makes it possible on the one hand to separate incompatible ingredients from one another and on the other hand to offer several different components of the agent in combination, which are used at different times.

In this context, the term “component” refers to a part of the agent that can be distinguished from a possibly further component of the agent on the basis of one or more characteristics, for example the type and/or amount of its ingredients, physical properties, external appearance, etc. Individual components of the agent can be present in liquid form, as defined herein, or in solid form, as defined herein, and advantageously spatially separated from one another.

In some embodiments, a textile treatment composition according to the invention is preferably a liquid textile treatment composition as defined herein.

As was surprisingly found, dispersions of cationically modified polyurethanes have a softening effect on textile fibers, in particular on cotton fibers, when they are brought into contact with laundry in the course of a rinsing process after the actual washing step. In order to be able to achieve such an effect, even low concentrations of such a dispersion are sufficient. The cationically modified polyurethanes are not only toxicologically safe and easily deposit on negatively charged substrates such as keratin, hair, leather and cotton, but also have an antistatic and antimicrobial effect.

Accordingly, in a first aspect, the present invention is directed to the use of a dispersion of at least one cationically modified polyurethane as a textile softener in textile treatment processes. In particular, the present invention relates to the use of a dispersion as described below for conditioning, in particular for softening, textiles. The present invention relates both to uses in which a dispersion as described herein is used in a manual textile treatment process or, preferably, in the washing machine.

A dispersion of one or more cationically modified polyurethanes can in principle be obtained by dispersing at least one cationically modified polyurethane in an aqueous phase.

1. a) Bereitstellen mindestens eines kationisch modifizierten Polyurethan-Präpolymers;
2. b) Emulgieren des Präpolymers aus Schritt a) in eine wässrige Phase; und
3. c) Quervernetzen des emulgierten Präpolymers aus Schritt b), um eine Dispersion eines kationisch modifizierten Polyurethans zu erhalten.

In various embodiments, a dispersion of a cationically modified polyurethane is obtainable in particular by

1. a) providing at least one cationically modified polyurethane prepolymer;
2. b) emulsifying the prepolymer from step a) into an aqueous phase; and
3. c) crosslinking the emulsified prepolymer from step b) to obtain a dispersion of a cationically modified polyurethane.

A combination of the above approaches is also possible, in that at least one cationically modified polyurethane prepolymer is dispersed in an aqueous phase and at least one cationically modified polyurethane prepolymer is dispersed in the same aqueous phase and can then be crosslinked.

• ii) mindestens einer Polyiosocyanat-Verbindung (B) und wahlweise
• iii) mindestens einer Polyol-Verbindung (C).

Although basically any type of cationically modified polyurethane for use according to the present invention and as a component of a textile treatment agent, in particular a fabric softener, therein acting as a textile-softening component, is suitable as long as it is harmless for the respective application from a health and ecological point of view, ie is toxicologically harmless and biodegradable, in the context of the present invention, particular preference is given to cationically modified polyurethanes which are obtainable by crosslinking a polyurethane prepolymer which in turn is obtainable by reacting i) at least one organic compound (A) comprising at least one , preferably at least two isocyanate-reactive functional groups and at least one cationic functional group, or a salt of compound (A),
With

• ii) at least one polyisocyanate compound (B) and optionally
• iii) at least one polyol compound (C).

1. i) mindestens einer organischen Verbindung (A) umfassend mindestens eine, vorzugsweise mindestens zwei Isocyanat-reaktive funktionelle Gruppen und mindestens eine kationische funktionelle Gruppe, oder eines Salzes der Verbindung (A),
   mit
2. ii) mindestens einer Polyiosocyanat-Verbindung (B)
   und wahlweise
3. iii) mindestens einer Polyol-Verbindung (C).

Accordingly, in some embodiments, step a) above comprises reacting

1. i) at least one organic compound (A) comprising at least one, preferably at least two, isocyanate-reactive functional groups and at least one cationic functional group, or a salt of compound (A),
   With
2. ii) at least one polyisocyanate compound (B)
   and optional
3. iii) at least one polyol compound (C).

In various embodiments, a compound (A) suitable in the context of the present invention is a polyol comprising at least one cationic functional group, preferably a diol comprising at least one cationic functional group. In some embodiments, a cationic functional group is in particular an ammonium group, preferably a quaternary ammonium group.

Particularly suitable in the context of the following invention are those compounds (A) which are alkoxylated, in particular ethoxylated, propoxylated and/or butoxylated, dialkylammonium polyols, in particular diols. A commercially available example is ethoxylated cocoalkylmethylammonium methanesulfonate. Such compounds are available, for example, under the brand name ^Rewoquat® CPEM from Evonik.

• wobei jedes R unabhängig H oder ein geradkettiger, cyclischer oder verzweigter, gesättigter oder ungesättigter oder aromatischer Kohlenwasserstoffrest ist mit bis zu 50 Kohlenstoffatomen, vorzugsweise bis zu 25 Kohlenstoffatomen, noch bevorzugter bis zu 15 Kohlenstoffatomen, der eine oder mehrere Gruppen ausgewählt aus -O-, -(CO)- und -NH- enthalten kann;
• und X ausgewählt wird aus geradkettigen, cyclischen oder verzweigten, gesättigten, ungesättigten oder aromatischen, substituierten oder unsubstituierten Kohlenwasserstoffresten mit bis zu 5000, beispielsweise mit bis zu 5, 15, 20, 25, 30, 35, 40, 45, 50, 100, 150, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1500, 2000, 2500, 3000, 3500, 4000, 4500 oder 5000 Kohlenstoffatomen, vorzugsweise mit bis zu 500 Kohlenstoffatomen, bevorzugter mit bis zu 100 Kohlenstoffatomen, noch bevorzugter mit bis zu 50 Kohlenstoffatomen, insbesondere mit bis zu 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 oder 20 Kohlenstoffatomen, wobei X mindestens eine, insbesondere mindestens zwei, bevorzugt jedoch nicht mehr als 10, noch bevorzugter nicht mehr als 7, beispielsweise nicht mehr als 5 Gruppen -O-(Y)_n-H enthält, wobei Y mit jedem Vorkommen jeweils unabhängig eine Gruppierung ausgewählt aus der Gruppe bestehend aus einer Ethylenoxid- (EO), Propylenoxid- (PO) und einer Butylenoxid- (BO) Gruppierung, vorzugsweise aus der Gruppe bestehend aus EO und PO, bezeichnet und n in jeder Gruppe -O-(Y)_n-H unabhängig eine ganze Zahl von 1 bis 100, vorzugsweise 2 bis 75, noch bevorzugter 2 bis 50 bezeichnet, und wobei X weiterhin wahlweise eine oder mehrere Gruppen ausgewählt aus -O-, -(CO)-, -NH- und -N(R¹)₂-, insbesondere eine oder mehrere Gruppen ausgewählt aus -O-, -NH- und -N(R¹)₂-, enthalten kann, wobei jedes R¹ jeweils unabhängig ausgewählt ist aus geradkettigen, cyclischen oder verzweigten, gesättigten, ungesättigten oder aromatischen, substituierten oder unsubstituierten Kohlenwasserstoffresten mit bis zu 20, vorzugsweise bis zu 10 Kohlenstoffatomen, beispielsweise 1, 2, 3, 4, 5, 6, 7, 8, 9, oder 10 Kohlenstoffatomen. Die Gruppen -O-(Y)_n-H sind aus der Zählung der Kohlenstoffatome der Gruppierung X ausgenommen.

In various embodiments, a compound (A) is a compound of the formula

(N ⁺ (R) ₃ )-X (I),

• wherein each R is independently H or a straight-chain, cyclic or branched, saturated or unsaturated, or aromatic hydrocarbon radical having up to 50 carbon atoms, preferably up to 25 carbon atoms, more preferably up to 15 carbon atoms, containing one or more groups selected from -O-, -(CO)- and -NH-;
• and X is selected from straight-chain, cyclic or branched, saturated, unsaturated or aromatic, substituted or unsubstituted hydrocarbon radicals of up to 5000, for example up to 5, 15, 20, 25, 30, 35, 40, 45, 50, 100, 150, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1500, 2000, 2500, 3000, 3500, 4000, 4500 or 5000 carbon atoms, preferably up to 500 carbon atoms, more preferably up to 100 carbon atoms , more preferably having up to 50 carbon atoms, especially up to 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, where X is at least one , in particular at least two, but preferably not more than 10, more preferably not more than 7, for example not more than 5 groups -O-(Y) _n -H, where Y with each occurrence is independently a moiety selected from the group consisting of an ethylene oxide (EO), propylene oxide (PO) and a butylene oxide (BO) group ung, preferably selected from the group consisting of EO and PO, and n in each group -O-(Y) _n -H independently denotes an integer from 1 to 100, preferably 2 to 75, more preferably 2 to 50, and wherein X further optionally one or more groups selected from -O-, -(CO)-, -NH- and -N(R ¹ ) ₂ -, in particular one or more groups selected from -O-, -NH- and -N( R ¹ ) ₂ -, wherein each R ¹ is independently selected from straight-chain, cyclic or branched, saturated, unsaturated or aromatic, substituted or unsubstituted hydrocarbon radicals having up to 20, preferably up to 10 carbon atoms, for example 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. The -O-(Y) _n -H groups are excluded from the carbon atom count of the X moiety.

If present, substituents are selected in the context of the present invention from halogens, e.g. CI. In various embodiments, the groups defined above are unsubstituted.

In the context of the present invention, a group -O-(Y) _n -H, more specifically the terminal hydroxy group of the group -O-(Y) _n -H, is an isocyanate-reactive functional group. In various embodiments, Y in each -O-(Y) _n -H group is identical, for example in some embodiments each Y in each -O-(Y) _n -H group of compound (A) with each occurrence denotes an ethylene oxide- ( EO) grouping. In some other embodiments, each Y in each -O-(Y) _n -H group of compound (A) with each occurrence denotes a propylene oxide (PO) moiety. In some further embodiments, each Y in each -O-(Y) _n -H group of compound (A) with each occurrence denotes a butylene oxide (BO) moiety. In various embodiments, a group -O-(Y) _n -H contains any mixture of ethylene oxide (EO), propylene oxide (PO), and butylene oxide (BO) moieties, with the total number of moieties in corresponds to a group -O-(Y) _n -H n . In various embodiments, in a compound (A), at least one -O-(Y) _n -H group differs from the other -(Y) _n -H groups. For example, a compound (A) may be a compound of formula (I) as defined above wherein in one group -O-(Y) _n -HY denotes an EO moiety at each occurrence, and in another -O-(Y) n -HY Group -O-(Y) _n -HY denotes a PO grouping with each occurrence and/or in a further group -O-(Y) _n -HY denotes a BO grouping with each occurrence. In various embodiments, all -O-(Y) _n -H groups in a compound (A) are different from each other. In various other embodiments, all -O-(Y) _n -H groups of a compound (A) are identical.

In various embodiments, the compound (A) is a compound of the formula (I) in which the R radicals contain no heteroatoms and/or are unsubstituted. In various embodiments, the group X also contains no heteroatoms and/or is substituted, apart from the at least one group --O-(Y) _n --H, ie it contains no group --N(R ¹ ) ₂ --, for example. In various other embodiments, in particular in one of the two aforementioned preferred embodiments, the number of carbon atoms in the radicals R is preferably not more than 15 and/or the number of carbon atoms in the group X is preferably not more than 50, in particular not more than 40, for example not more than 30, 25 or 15, the carbon atoms of the group(s) -O-(Y) _n -H of the moiety X not being included in this calculation. In further such embodiments, a group X contains at least one, preferably at least two, but preferably no more than 7, especially no more than 5 groups -O-(Y) _n -H as defined herein. In further such preferred embodiments, each R is independently H or a straight or branched chain alkyl or alkylene group. In various other such preferred embodiments, n in each group -O-(Y) _n -H independently denotes an integer from 2 to 100, preferably from 2 to 80, more preferably from 2 to 75, for example from 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 to 25, 30, 35, 40, 45, 50, 55, 60, 65, 70 or 75, or from 2 to 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20. In further such preferred embodiments a compound (A) of formula (I) at least one group -O-(Y) _n -H, where Y denotes with each occurrence EO, and/or at least one group -O-(Y) _n -H, where Y denotes each occurrence denotes PO, and/or at least one group -O-(Y) _n -H, where Y denotes BO with each occurrence, and/or at least one group -O-(Y) _n -H, where Y with each occurrence is independently selected from EO, PO and BO; more preferably at least one -O-(Y) _n -H group, where Y at each occurrence denotes EO, and/or at least one -O-(Y) _n -H group, where Y at each occurrence denotes PO; more preferably at least one group, especially at least two groups -O-(Y) _n -H, where Y denotes EO at each occurrence. Most preferably a compound of formula (I) comprises at least two -O-(Y) _n -H groups as defined herein.

Suitable salts of compound (A) include, but are not limited to, salts of compound (A) with acids. Examples of acids suitable in this context are acetic acid, Formic acid, hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, nitrous acid, boric acid, carbonic acid, perchloric acid, acrylic acid, methacrylic acid, itaconic acid, maleic acid, 2-carboxyethyl acrylate, lactic acid, ascorbic acid, glycine, alanine, leucine, norleucine, phenylalanine, serine, taurine, valine , α-aminobutyric acid, palmitic acid, stearic acid, benzoic acid, mercaptoacetic acid, salicylic acid, pivalic acid, chloroacetic acid, dichloroacetic acid, trichloroacetic acid, citric acid, propionic acid, glycolic acid, 1-sulfonaphthalene, tartaric acid, phthalic acid, isophthalic acid, terephthalic acid, 5-sulfosalicylic acid, benzenesulfonic acid, cyclohexanecarboxylic acid, or similar -, m- and p-toluic acid, o-, m- and p-aminobenzoic acid, p-hydroxybenzoic acid, phenylacetic acid, methylbenzenesulfonic acid, butyric acid, valeric acid, oxalic acid, maleic acid, fumaric acid, malonic acid, succinic acid, glutaric acid, oleic acid, o-, m- and p-chlorobenzoic acid, o-, m- and p-bromobenzoic acid, anthranilic acid, o-, m- and p-nitrobenzoic acid, adipic acid urea, caprylic acid, caproic acid, 1-lauric acid, fluoroacetic acid, capric acid, myristic acid, methoxyacetic acid, dodecanesulfonic acid, dodecylbenzenesulfonic acid, ethylbenzenesulfonic acid, octanesulfonic acid, hexanesulfonic acid, polyacrylic acid, and copolymers of acrylic, methacrylic, itaconic, maleic and fumaric acid.

In the context of the present invention, a polyisocyanate compound (B) is a compound which comprises at least two isocyanate groups. For example, a compound (B) can be a diisocyanate or a triisocyanate. In various embodiments it is preferred that the polyisocyanate is a diisocyanate. However, the incorporation of small amounts of isocyanate having a functionality greater than two, particularly a triisocyanate, is also contemplated and may even be beneficial in certain circumstances. Such polyisocyanates can act as crosslinkers. In this case, when the polyisocyanate acts as a crosslinking agent, preference is given to polyisocyanates based on hexamethylene diisocyanate, for example in the form of corresponding isocyanurates. Allophanates of diisocyanates are also suitable. The amount of crosslinker is usually about 0 to 5% by weight, preferably about 0 to 2% by weight, for example about 0, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6 , 0.7, 0.8, 0.9, 1.0, 1.2, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1 .9 or 2.0% by weight based on the total weight of the respective reaction mixture.

Suitable diisocyanates include methylenediphenyl diisocyanate (MDI), toluene-2,4-diisocyanate (TDI), hexamethylene diisocyanate (HDI), polymeric diphenylmethane diisocyanate (PMDI), isophorone diisocyanate (IPDI) and methylene-4,4-bis(cyclohexyl)diisocyanate (H12MD1) . Although both aliphatic and aromatic polyisocyanates are contemplated, it is preferred that the polyisocyanate is an aliphatic polyisocyanate. Thus, in some embodiments, the polyisocyanate is an aliphatic diisocyanate. The most preferred aliphatic diisocyanates include isophorone diisocyanate, hexamethylene diisocyanate, and mixtures thereof. Suitable polyisocyanates are commercially available, for example, under the brand name ^Desmodur® from Bayer AG (DE). It is of course also possible to use different compounds (C), ie different polyisocyanates, as defined above, together.

In the context of the present invention, a polyol compound (C) is a compound comprising at least two hydroxy groups, which can be selected in particular from the group consisting of polyester polyols, polyether polyols, polycarbonate polyols, polysiloxane polyols and polyolefin polyols, such as (hydrogenated ) polybutadiene polyols.

The polyester polyols which are suitable in the context of the present invention include, for example, those which can be obtained by reacting dicarboxylic acids with polyols in a polycondensation reaction. The dicarboxylic acids can be aliphatic, cycloaliphatic or aromatic and/or derivatives of the aforementioned such as anhydrides, esters or acid chlorides. Concrete examples thereof are succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid or sebacic acid, phthalic acid, isophthalic acid, trimellitic acid, phthalic anhydride, tetrahydrophthalic anhydride, glutaric anhydride, maleic acid, maleic anhydride, fumaric acid, dimer fatty acids and dimethyl terephthalate. Examples of suitable polyols are monoethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 3-methylpentane-1,5-diol, neopentyl glycol (2,2-dimethyl-1,3-propanediol), 1,6-hexanediol, 1,8-utaneglycolcyclohexanedimethanol, 2-methylpropane-1,3-diol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, polypropylene glycol, dibutylene glycol and polybutylene glycol. Alternatively they can be obtained by ring opening polymerisation of cyclic esters, preferably ε-caprolactone. Preferred are crystalline/semi-crystalline polyols such as esters of 1,4-butanediol with adipic acid.

In various embodiments, the polyester polyol has a melting point Tm > 0°C, preferably > 40°C and/or a number-average molecular weight Mn in the range from 400 to 5000, preferably 500 to 3000 g/mol, particularly preferably 800 to 2500 g/mol. most preferably 1000 to 2000 g/mol.

The polyether polyol can be a polyalkylene glycol homo- or copolymer, preferably a polypropylene glycol homo- or copolymer, a polyethylene glycol homo- or copolymer, a polytetramethylene glycol homo- or copolymer, or a polypropylene glycol/polyethylene glycol block copolymer.

In various embodiments, the polyether polyol has a number average molecular weight of 1000 to 4000, preferably 1000 to 3000 g/mol.

Suitable polycarbonates can be obtained by reacting carbonic acid derivatives, for example diphenyl carbonate, dimethyl carbonate or phosgene, with diols. Suitable examples of such diols are ethylene glycol, 1,2- and 1,3-propanediol, 1,3- and 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, neopentyl glycol, 1,4-bishydroxymethylcyclohexane, 2-methyl-1,3-propanediol, 2,2,4-trimethylpentanediol-1,3, dipropylene glycol, polypropylene glycols, dibutylene glycol, polybutylene glycols, bisphenol A, tetrabromobisphenol A and lactone-modified diols. The diol component can also have ether or ester groups in addition to the terminal OH groups. the Hydroxyl polycarbonates should be essentially linear. However, they can optionally be slightly branched through the incorporation of polyfunctional components, in particular low molecular weight polyols. Suitable examples are glycerol, trimethylolpropane, 1,2,6-hexanetriol, 1,2,4-butanetriol, trimethylolpropane, pentaerythritol, quinitol, mannitol and sorbitol, methyl glycoside, 1,3,4,6-dianhydrohexitols. Suitable polycarbonate polyols include, without limitation, those available under the trade names ^Desmophen® C3200 (Bayer) and ^Kuraray® C2050 (poly(3-methyl-1,5-pentanediol, 1,6-hexanediol) carbonate; Kuraray).

Also suitable are amorphous polyols, preferably polyether polyols such as polypropylene glycol or poly-THF, with a number-average molecular weight Mn in the range from 400 g/mol to 5000 g/mol, a crystallinity of less than 10% and a glass transition temperature Tg in the range of -120 °C to 40 °C, preferably -70 °C to 30 °C, the crystallinity and the glass transition temperature being determined by differential scanning calorimetry (DSC) according to ISO 11357.

The amorphous polyols that can be used according to the embodiments described here are preferably polyether polyols and/or have a number-average molecular weight Mn in the range from 400 g/mol to 5000 g/mol, preferably 500 to 3000 g/mol, particularly preferably 800- 2500 g/mol, most preferably 1000 to 2000 g/mol. "Amorphous" as used herein in relation to the polyols means that the polyol has a crystallinity of less than 10%, preferably less than 5%, more preferably less than 2% as determined by differential scanning calorimetry (DSC ) determined according to ISO 11357. In some embodiments, the amorphous (polyether) polyols have a glass transition temperature Tg in the range of -120 °C to 40 °C, preferably -70 °C to 30 °C, again determined by Differential Scanning Calorimetry (DSC) according to ISO 11357.

In various embodiments, the reaction mixture also includes a crystalline or semi-crystalline polyol. The crystalline or semi-crystalline polyol is preferably a polyester polyol or polycarbonate and can have a number average molecular weight Mn in the range 400 g/mol to 5000 g/mol, preferably 500 to 3000 g/mol, more preferably 800-2500 g/mol, most preferably 1000 to 2000 g/mol. "Crystalline" as used herein in relation to the (polyester) polyols refers to a crystallinity of at least 90%, preferably at least 95% as determined by differential scanning calorimetry (DSC) according to ISO 11357. Similarly, as used herein in relation to the (polyester) polyols, "semi-crystalline" means having a crystallinity of at least 50%, preferably at least 70% but less than 90%. Partially crystalline (polyester) polyols thus include crystalline and non-crystalline, ie amorphous areas. The crystalline and partially crystalline (polyester) polyols can have a melting point Tm in the range from 40°C to 220°C, preferably >40°C to <160°C, more preferably >40°C to 80°C, most preferably >40 °C to 60 °C, again determined by differential scanning calorimetry (DSC) according to ISO 11357 with a heating rate of 20K/min. The same procedure can be used for the determination of the enthalpy of fusion, using the results of the second heating cycle for the determination of the enthalpy of fusion. In various embodiments of the invention, the polyols have enthalpies of fusion of more than 90 J/g, preferably more than 115 J/g. If no If a standard reference of the polyol with a known crystallinity is available for the determination by DSC, known alternative methods such as X-ray diffractometry can be used.

Also suitable are low molecular weight polyols such as glycol and derivatives thereof, such as di- or triethylene glycol, 1,2- or 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, Cyclohexanedimethanol and 2,2-bis(4'hydroxycyclohexyl)propane, but also polyhydric alcohols such as trishydroxyalkylalkanes (e.g. trimethylolpropane) or tetrakishydroxyalkylalkanes (e.g. pentaerythritol).

Also suitable are polyols which are hydroxy-functionalized polymers, such as hydroxy-functionalized siloxanes. Examples of siloxanes that can be used are hydroxy-functionalized polydimethylsiloxanes, particularly in liquid form, such as are commercially available under the name ^Tegomer® H-Si 2311 (Evonik, Germany) with a molecular weight Mn of about 2200 g/mol. Suitable polydimethylsiloxane (PDMS) polyols are, for example, in US6794445B2 described.

Polyolefin polyols suitable in the context of the present invention are derived, for example, from oligomeric and polymeric olefins having at least two terminal hydroxyl groups. As a non-limiting example, alpha, omega-dihydroxypolybutadiene is preferred.

In both variants of producing a dispersion of a cationically modified polyurethane, i.e. either by dispersing a cationically modified polyurethane in an aqueous phase, the corresponding cationically modified polyurethane being obtainable by crosslinking a cationically modified polyurethane prepolymer, obtainable as defined above; or by a manufacturing process comprising steps a)-c) above), according to some embodiments, reacting at least one compound (A), at least one compound (B) and optionally at least one compound (C), each as defined above, in the presence of at least of a catalyst.

Catalysts suitable in the context of the present invention are known in the art and include, for example but not limited to, tin, bismuth or zinc-based catalysts, for example dibutyltin dilaurate or dimethylbis[(1-oxoneodecyl)oxy]stannane, for example commercially available from Trade name Fomrez UL28 (Momentive Performance Materials GmbH, Germany). Alternative catalysts with high reactivity are bismuth neodecanoate and Zn neodecanoate available under the trade names BorchiKat 315 and BorchiKat 0761 (OMG Borchers GmbH, Germany). Usual amounts of catalyst are in the range from about 0.001 to 5% by weight, preferably in the range from about 0.01 to about 2% by weight, for example about 0.01, 0.02, 0.05, 0. 09, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.5 or 2.0 wt. -%, each based on the total weight of the reaction mixture of polyol and isocyanate components.

The polyisocyanate is usually used in a molar excess in relation to the OH groups of all the polyols present, i.e. the at least one compound (A) and optionally the at least one compound (C), the OH/NCO equivalent ratio preferably being 1:1. 1 to 1:4, more preferably 1:1.2 to 1:1.3. The amount of the at least one polyisocyanate in the reaction mixture for preparing the prepolymer is typically in the range from 10 to 20% by weight, based on the reaction mixture. The remainder of the reaction mixture may consist of the polyol component(s) as defined above.

In various embodiments it can be advantageous to heat a respective polyol (mixture). Heating may be necessary when the polyols used are solid at room temperature and need to be melted to form a usable/handleable polyol component. In some embodiments, the at least one compound (A) and the optional at least one compound (C) are combined and heated to about 70 to 95°C, e.g., about 75°C while stirring the mixture under vacuum to dry. After mixing, the mixture can be cooled to about 60°C for the addition of the isocyanates.

The polyol mixture is then combined with at least one polyisocyanate (B) in the reaction mixture to form the prepolymer. The prepolymer reaction generally takes place at elevated temperature, for example in the range between about 70° C. and about 95° C., particularly preferably at about 80° C., over a period of about 1 to about 24 hours.

Accordingly, in various embodiments, step b) occurs at elevated temperatures ranging from about 27 to about 95°C, preferably about 50 to about 90°C.

The reaction is continued until the free isocyanate content is at or very close to the calculated value as determined by standard titration with dibutylamine. Preferred values for the content of free isocyanate in the prepolymer are in the range between 0.2 and 3% by weight, preferably 1 to 2% by weight, based on the total weight of the reaction mixture.

As described above, the polyisocyanate is reacted in the polyurethane prepolymer-forming reaction at a concentration in excess of the stoichiometric concentration required for complete reaction with the hydroxyl groups. The excess used may comprise an OH/NCO equivalent ratio of 1:1.1 to 1:4. Preferably, the amount of polyisocyanate should be from 20% to 150% above the stoichiometric concentration required for complete reaction with the hydroxyl groups.

According to the present invention, the cationically modified polyurethane prepolymer thus obtained is then dispersed in an aqueous phase (step b). In order to facilitate the transfer and dispersion of the prepolymer, it may be desirable to previously dissolve the prepolymer in a suitable solvent, preferably a water-miscible, highly volatile solvent. The prepolymer is preferably dispersed by adding the prepolymer in the aqueous phase with stirring. The degree of hardness of the water used is not important for the process, so the use of distilled or deionized water is not absolutely necessary. The dispersing according to step b) preferably takes place at a temperature of approximately 27 to 95.degree. C., in particular at approximately 30 to 90.degree. C., more preferably at approximately 40 to 80.degree. This can mean that the aqueous phase is heated before the addition of the prepolymer and/or that the mixture of both phases is heated, for example in the course of stirring. Agitation preferably occurs for a period of time from about 1 minute to about 60 minutes, for example about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 20, 25, 30, 35, 40, 45, 50, 55 or 60 minutes, preferably using a suitable stirring or mixing device, for example a magnetic stirrer or a static mixer.

Subsequently, the dispersion of the cationically modified polyurethane prepolymer thus obtained is chain-extended to obtain a dispersion of a cationically modified polyurethane polymer. Chain extenders suitable for this purpose are known in the art and include, but are not limited to, inorganic or organic polyamines having an average of about 2 or more primary and/or secondary amine groups, or combinations thereof.

Suitable organic amines include diamines and polyamines such as, but not limited to, ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetramine (TETA), meta-xylylenediamine (MXDA), aminoethylethanolamine (AEEA), 2-methylpentanediamine, and the like. Mixtures of the above are also suitable. Propylenediamine, butylenediamine, hexamethylenediamine, cyclohexylenediamine, phenylenediamine, tolylenediamine, 3,3-dichlorobenzide, 4,4'-methylenebis-(2-chloroaniline), 3,3-dichloro-4,4-diaminodiphenylmethane and sulfonated primary are also suitable and/or secondary amines and the like, and mixtures thereof.

Useful inorganic amines include hydrazine, substituted hydrazines and hydrazine reaction products and the like, and mixtures thereof.

Overall, preference is given in this context to adipic acid dihydrazide, ethylenediamine, diethylenetriamine, triethylenetetraamine, tetraethylenepentamine, pentaethylenehexamine, dipropylenetriamine, hexamethylenediamine, hydrazine, isophoronediamine, N-(2-aminoethyl adducts)-acrylamido-2-methylpropane-1-sulfonic acid (AMPS ^® ) and ethylenediamine, adduct salts of (meth)acrylic acid and ethylenediamine, adducts of 1,3-propanesulfone and ethylenediamine, or any combination of these polyamines. Preferably, bifunctional primary amines, especially ethylenediamine, are used.

However, since water can in principle also function as a chain extender, the use of one of the amine-based chain extenders mentioned above is not absolutely necessary.

The amount of chain extender used, water not being understood as such in this context, is, in various embodiments, approximately 0 to 20% by weight, preferably about 0 to 15% by weight, for example about 0, 0.1, 05, 1.0, 1.5, 2.0, 3.0, 4.0, 5.0, 6.0, 7, 0, 8.0, 9.0, 10.0, 11.0, 12.0, 13.0, 14.0 or 15.0% by weight based on the total weight of the polyurethane prepolymer.

The reaction is continued until the free isocyanate content is at or very close to the calculated value as determined by standard titration with dibutylamine. Preferred values for the content of free isocyanate in the prepolymer are in the range between 0.2 and 3% by weight, preferably 1 to 2% by weight, based on the total weight of the reaction mixture.

Any solvents and/or acids present (entered in the form of salts of compound (A)) can then be removed in vacuo.

In various embodiments, the amount of cationic component, i.e. the amount of compound (A), in the polyurethane polymer is about 1 to 20% by weight, for example about 1, 2, 3, 4, 5, 6, 7, 8, 9 , 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20% by weight, preferably about 1 to 8% by weight, for example about 1.5, 2.5, 3.5, 4.5, 6.5, 7.5% by weight, each based on the total weight of the final polymer.

In various embodiments, the number of -(Y) _n -H groups, as defined above, can be from 0.1 to about 20 milliequivalents per gram of urethane polymer.

In various embodiments, the at least one cationically modified polyurethane is in an amount of about 1 to 50% by weight, for example about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 20, 25, 30, 35, 40, 45 or 50% by weight, preferably about 10 to 25% by weight, for example about 10, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25% by weight, based in each case on the total weight of the dispersion, contained in the latter.

In various embodiments, the dispersion of at least one cationically modified polyurethane has a viscosity of approximately 100 to 1000 mPas, for example 100, 150, 200, 500, 700, 750, 800, 850, 900, 950 or 1000 mPas, preferably approximately 200 to 600 mPas , for example about 100, 150, 300, 350, 400, 450, 500, 550 or 600 mPas.

As already mentioned, it was surprisingly found that dispersions of cationically modified polyurethanes, as described above, have a softening effect on textile fibers, in particular on cotton fibers, when they are brought into contact with laundry in the course of a rinsing process after the actual washing step. In order to be able to achieve such an effect, even low concentrations of such a dispersion are sufficient. A dispersion of at least one cationically modified polyurethane as defined and described above can be brought into contact with the laundry to be treated/conditioned either as a component of a textile treatment agent, for example a fabric softener, or in pure form, ie not as a component of a textile treatment agent.

If a dispersion as described herein of at least one cationically modified polyurethane polymer is used in pure form, it is sufficient if the dispersed, cationically modified polyurethane is present in an amount of about 1 to 50% by weight, for example about 1, 2, 3, 4, 5 , 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 20, 25, 30, 35, 40, 45 or 50% by weight, preferably about 10 to 25% by weight, for example about 10, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25% by weight, based in each case on the total weight of the dispersion.

Advantageous amounts of a dispersion as described above are in the range from about 0.5 to 50 ml, preferably in the range from about 1 to 50 ml, for example about 1, 2, 3, 4, 5, 6, 7, 8, 9, 0 , 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 25, 30, 35, 40, 45 or 50 ml, more preferably in the range of about 3 to 30 ml to the amount of dispersion that is sufficient for the treatment/conditioning of a normal laundry load of approx. 1-5 kg and is accordingly introduced into the fabric softener compartment of a washing machine or used in the course of a manual washing process following the actual laundry cleaning process using a detergent.

However, since the advantageous effect of a dispersion as described herein of at least one cationically modified polyurethane also becomes apparent when such a dispersion is used as a component of a textile treatment agent, the present invention is also directed in a further aspect to a textile treatment agent comprising at least one dispersion of at least one cationically modified polyurethane as defined and described herein. In various embodiments, such a textile treatment agent is a fabric softener. However, other types of textile treatment agents, such as textile sprays, for example ironing sprays, and the like, are also contemplated.

If a dispersion as described herein of at least one cationically modified polyurethane, or a mixture of several such dispersions, is part of a textile treatment agent, for example a fabric softener, it is preferably in an amount of about 5 to 25% by weight, more preferably in an amount of about 6 to 15% by weight, for example in an amount of approximately 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15% by weight, based in each case on the total weight of the composition.

In addition to the at least one dispersion of at least one cationically modified polyurethane polymer, the agents according to the invention can contain other ingredients, for example at least one other component, preferably at least two other components, which further improve the performance and/or aesthetic properties of the agent. These include, for example, in particular other softening compounds, fragrances, surfactants, thickeners, emulsifiers, hydrotropes, non-aqueous solvents, electrolytes, pH adjusters, perfume carriers, fluorescent agents, dyes, foam inhibitors, antiredeposition agents, enzymes, optical brighteners, graying inhibitors, shrinkage inhibitors, anti-crease agents, Color transfer inhibitors, antimicrobial agents, germicides, fungicides, antioxidants, corrosion inhibitors, antistatic agents, ironing aids, repellents and impregnating agents, swelling and anti-slip agents and UV absorbers. A composition according to the invention can of course comprise one or, preferably, several of these adjuvants.

A "softening compound" within the meaning of the present invention is a compound that is able to soften textile fabrics or create this impression for the consumer. This designation correspondingly also includes a dispersion of at least one cationically modified polyurethane, as described above. In various embodiments, however, it is provided that at least one further plasticizing compound, i.e. a plasticizing compound, which is used in addition to, in other words in combination with, the at least one dispersion of at least one cationically modified polyurethane, as defined herein, is preferably selected from the Group of quaternary ammonium compounds, selected in particular from the group of ester quats.

The term "ester quat" as used herein refers to esters of quaternary ammonium polyols, particularly quaternary ammonium diols and/or triols such as triethanolmethylammonium or diethanoldimethylammonium, with fatty acids.

In general, the use of esterquats in cosmetic products, detergents and aftertreatment agents, especially in fabric softeners, is known in the prior art. These contribute to improving the soft handle, reducing the static charging of the textile fabric and reducing the drying time.

In various embodiments, the textile treatment agent according to the invention contains at least one ester quat of the formula (I) N ⁺ (R1) _4-n ((CH ₂ ) _m -OC(O)-R ² ) _n X- where (I), each R ¹ independently of one another is substituted or unsubstituted, linear or branched alkyl or alkenyl, preferably unsubstituted or hydroxy-substituted alkyl of 1 to 10 carbon atoms; each R ² is linear or branched, substituted or unsubstituted alkyl or alkenyl, or substituted or unsubstituted (hetero)aryl of up to 26 carbon atoms, preferably linear unsubstituted C _10-26 alkyl; n is 1, 2, 3 or 4, preferably 1, 2 or 3; m is an integer from 1 to 20, preferably from 1 to 4; and X ^- is any anion.

• (i) n 2 oder 3, vorzugsweise 2; und/oder
• (ii) m 1, 2, 3 oder 4, vorzugsweise 2; und/oder
• (iii) jedes R¹ unabhängig voneinander ausgewählt aus der Gruppe bestehend aus Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, Hydroxymethyl, 2-Hydroxyethyl, 2-Hydroxypropyl und 3-Hydroxy-propyl, vorzugsweise ein erstes R¹ ausgewählt wird aus Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl und iso-Butyl und ein zweites R¹ ausgewählt wird aus Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, Hydroxymethyl, 2-Hydroxyethyl, 2-Hydroxypropyl und 3-Hydroxypropyl; und/oder
• (iv) jedes R² unabhängig voneinander ausgewählt aus linearem, unsubstituiertem C_12-20 Alkyl, vorzugsweise C_12-18 Alkyl; und/oder
• (iv) X^- ausgewählt wird aus anorganischen oder organischen Anionen, insbesondere Fluorid, Chlorid, Bromid und Methosulfat.

In various embodiments, in the compounds of formula (I)

• (i) n is 2 or 3, preferably 2; and or
• (ii) m is 1, 2, 3 or 4, preferably 2; and or
• (iii) each R ¹ is independently selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, hydroxymethyl, 2-hydroxyethyl, 2-hydroxypropyl and 3-hydroxy-propyl, preferably a first R ¹ is selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl and iso-butyl and a second R ¹ is selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, hydroxymethyl, 2-hydroxyethyl, 2-hydroxypropyl and 3-hydroxypropyl; and or
• (iv) each R ² is independently selected from linear, unsubstituted C _12-20 alkyl, preferably C _12-18 alkyl; and or
• (iv) X ^- is selected from inorganic or organic anions, especially fluoride, chloride, bromide and methosulfate.

In a particularly preferred embodiment, the esterquat used is an esterquat of formula (I) wherein n=2 and m=2, the first R ¹ is selected from methyl and ethyl, preferably methyl, the second R ¹ is selected from methyl and 2-hydroxyethyl, preferably 2-hydroxyethyl, and each R ² is linear unsubstituted C _12-18 alkyl. Such esterquats are bis(acyloxyethyl)hydroxyethylmethylammonium compounds. The counterion is preferably methosulfate. Such esterquats are commercially available, for example, under the trade name ^Dehyquart® AU-57 (BASF SE, DE).

In various embodiments, the textile treatment agent contains, based on the total weight of the agent, at least 4% by weight of at least one other softening compound as defined above, in particular at least one compound of the formula (I), for example in amounts of up to 60% by weight, preferably up to 30% by weight, based in each case on the total weight of the textile treatment composition.

In various embodiments, an agent according to the invention comprises at least one fragrance.

All substances and mixtures known for this purpose can be used as fragrances or fragrances or perfume oils. For the purposes of this invention, the terms “fragrance(s)”, “fragrances” and “perfume oil(s)” are used synonymously. This means in particular all those substances or mixtures thereof which are perceived by humans and animals as an odour, in particular by humans as a pleasant odour.

Perfumes, perfume oils or perfume oil components can be used as fragrance components. Perfume oils or fragrances can, according to the invention, contain individual fragrance compounds, e.g. B. the synthetic products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type.

Perfume compounds of the aldehyde type are, for example, adoxal (2,6,10-trimethyl-9-undecenal), anisaldehyde (4-methoxybenzaldehyde), cymal (3-(4-isopropyl-phenyl)-2-methylpropanal), ethylvanillin, florhydral ( 3-(3-isopropylphenyl)butanal), Helional (3-(3,4-methylenedioxyphenyl)-2-methylpropanal), Heliotropin, Hydroxycitronellal, Lauraldehyde, Lyral (3- and 4-(4-Hydroxy-4-methylpentyl)- 3-cyclohexene-1-carboxaldehyde), methyl nonylacetaldehyde, Lilial (3-(4-tert-butylphenyl)-2-methylpropanal), phenylacetaldehyde, undecylene aldehyde, vanillin, 2,6,10-trimethyl-9-undecenal, 3-dodecen- 1-al, alpha-n-amylcinnamaldehyde, melonal (2,6-dimethyl-5-heptenal), 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde (Triplal), 4-methoxybenzaldehyde, benzaldehyde, 3-(4-tert - butylphenyl)propanal, 2-methyl-3-(para-methoxyphenyl)propanal, 2-methyl-4-(2,6,6-trimethyl-2(1)-cyclohexen-1-yl)butanal, 3-phenyl -2-propenal, cis -/trans -3,7-dimethyl-2,6-octadien-1-al, 3,7-dimethyl-6-octen-1-al, [(3,7-dimethyl-6- octenyl)oxy]acetaldehyde, 4-isopropylbenzylaldehyde, 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde, 2,4-dimethyl-3-cyclohexene-1- carboxaldehyde, 2-methyl-3-(isopropylphenyl)propanal, 1-decanal, 2,6-dimethyl-5-heptenal, 4-(tricyclo[5.2.1.0(2,6)]decylidene-8)butanal, octahydro -4,7-methane-1H-indenecarboxaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, para-ethyl-alpha,alpha-dimethylhydrocinnamaldehyde, alpha-methyl-3,4-(methylenedioxy)-hydrocinnamaldehyde, 3,4-methylenedioxybenzaldehyde, alpha -n-hexylcinnamaldehyde, m-cymene-7-carboxaldehyde, alpha-methylphenylacetaldehyde, 7-hydroxy-3,7-dimethyloctanal, undecenal, 2,4,6-trim ethyl-3-cyclohexene-1-carboxaldehyde, 4-(3)(4-methyl-3-pentenyl)-3-cyclohexenecarboxaldehyde, 1-dodecanal, 2,4-dimethylcyclohexene-3-carboxaldehyde, 4-(4-hydroxy- 4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, 7-methoxy-3,7-dimethyloctan-1-al, 2-methylundecanal, 2-methyldecanal, 1-nonanal, 1-octanal, 2,6,10 -Trimethyl-5,9-undecadienal, 2-methyl-3-(4-tert-butyl)propanal, dihydrocinnamaldehyde, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde, 5- or 6-Methoxyhexahydro-4,7-methanindan-1- or -2-carboxaldehyde, 3,7-dimethyloctan-1-al, 1-undecanal, 10-undecen-1-al, 4-hydroxy-3-methoxybenzaldehyde , 1-Methyl-3-(4-methylpentyl)-3-cyclohexenecarboxaldehyde, 7-Hydroxy-3J-dimethyloctanal, trans-4-decenal, 2,6-nonadienal, para-tolylacetaldehyde, 4-methylphenylacetaldehyde, 2-methyl -4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, ortho-methoxycinnamaldehyde, 3,5,6-trimethyl-3-cyclohexenecarboxaldehyde, 3J-dimethyl-2-methylene -6-octenal, phenoxyacetaldehyde, 5,9-dimethyl-4,8-decadienal, peony aldehyde (6, 10-dimethyl-3-oxa-5,9-undecadien-1-al), hexahydro-4,7-methanindan-1-carboxaldehyde, 2-methyloctanal, alpha-methyl-4-(1-methylethyl)benzeneacetaldehyde, 6, 6-dimethyl-2-norpinene-2-propionaldehyde, para-methylphenoxyacetaldehyde, 2-methyl-3-phenyl-2-propen-1-al, 3,5,5-trimethylhexanal, hexahydro-8,8-dimethyl-2- naphthaldehyde, 3-propylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde, 9-decenal, 3-methyl-5-phenyl-1-pentanal, methylnonylacetaldehyde, hexanal and trans-2-hexenal.

Perfume compounds of the ketone type are, for example, methyl beta-naphthyl ketone, musk indanone (1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one), Tonalide (6-acetyl-1,1,2,4,4,7-hexamethyltetralin), alpha-damascone, beta-damascone, delta-damascone, iso-damascone, damascenone, methyldihydrojasmonate, menthone, carvone, camphor, koavone (3rd ,4,5,6,6-pentamethylhept-3-en-2-one), fenchone, alpha-ionone, beta-ionone, gamma-methyl-ionone, fleuramon (2-heptylcyclopentanone), dihydrojasmon, cis-jasmon , iso-E-Super (1-(1,2,3,4,5,6J,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethan-1-one (and isomers) ), methylcedrenyl ketone, acetophenone, methylacetophenone, para-methoxyacetophenone, methyl beta-naphthyl ketone, benzylacetone, benzophenone, para-hydroxyphenylbutanone, celery ketone(3-methyl-5-propyl-2-cyclohexenone), 6-isopropyldecahydro-2-naphthone , dimethyloctenone, frescomenthe (2-butan-2-yl-cyclohexan-1-one), 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, methylheptenone, 2-(2-(4-methyl- 3-cyclohe xen-1-yl)propyl)cyclopentanone, 1-(p-menthen-6(2)yl)-1-propanone, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone, 2-acetyl-3, 3-dimethylnorbornane, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, 4-damascol, Dulcinyl(4-(1,3-benzodioxol-5-yl)butan-2-one), Hexalone(1-(2,6,6-trimethyl-2-cyclohexene-1-yl)-1,6-heptadien- 3-one), IsocyclemonE(2-acetonaphthone-1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl), methyl nonyl ketone, methylcyclocitrone, methyl lavender ketone, Orivon (4- tert-Amyl-cyclohexanone), 4-tert-butylcyclohexanone, Delphon (2-pentyl-cyclopentanone), Muscon ( CAS 541-91-3 ), neobutenone (1-(5,5-dimethyl-1-cyclohexenyl)pent-4-en-1-one), plicatone ( CAS 41724-19-0 ), Velouton (2,2,5-trimethyl-5-pentylcyclopentan-1-one), 2,4,4,7-tetramethyl-oct-6-en-3-one and tetrameran (6,10-dimethylundecene-2 -on).

Perfume compounds of the alcohol type are, for example, 10-undecen-1-ol, 2,6-dimethylheptan-2-ol, 2-methylbutanol, 2-methylpentanol, 2-phenoxyethanol, 2-phenylpropanol, 2-tert-butylcyclohexanol, 3,5,5-trimethylcyclohexanol, 3-hexanol, 3-methyl-5-phenylpentanol, 3-octanol, 3-phenylpropanol, 4-heptenol, 4-isopropylcyclohexanol, 4-tert-butylcyclohexanol, 6 ,8-dimethyl-2-nona-nol, 6-nonen-1-ol, 9-decen-1-ol, α-methylbenzyl alcohol, α-terpineol, amyl salicylate, benzyl alcohol, benzyl salicylate, β-terpineol, butyl salicylate, citronellol, cyclohexyl salicylate , Decanol, Dihydromyrcenol, dimethylbenzylcarbinol, dimethylheptanol, dimethyloctanol, ethyl salicylate, ethyl vaniline, eugenol, farnesol, geraniol, heptanol, hexyl salicylate, isoborneol, isoeugenol, isopulegol, linalool, menthol, myrtenol, n-hexanol, nerol, nonanol, octanol, p-menthane -7-ol, phenylethyl alcohol, phenol, phenyl salicylate, tetrahydrogeraniol, tetrahydrolinalool, thymol, trans-2-cis-6-nonadicnol, trans-2-nonen-1-ol, trans-2- Octenol, undecanol, vanillin, champiniol, hexenol and cinnamic alcohol.

Perfume compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinyl acetate (DMBCA), phenylethyl acetate, benzyl acetate, ethylmethylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate, benzyl salicylate, cyclohexyl salicylate, floramat, melusate and jasmacyclate.

The ethers include, for example, benzyl ethyl ether and ambroxan. The hydrocarbons mainly include terpenes such as limonene and pinene.

Mixtures of different fragrances are preferably used, which together produce an appealing fragrance. Such a mixture of fragrances can also be referred to as a perfume or perfume oil. Perfume oils of this kind can also contain natural mixtures of fragrances, such as are obtainable from vegetable sources.

Fragrances of plant origin include essential oils such as angelica root oil, anise oil, arnica flower oil, basil oil, bay oil, champaca flower oil, citrus oil, noble fir oil, noble pine cone oil, elemi oil, eucalyptus oil, fennel oil, pine needle oil, galbanum oil, geranium oil, ginger grass oil, guaiac oil, gurjun balm oil, helichrysum oil, ho oil , ginger oil, iris oil, jasmine oil, cajeput oil, sweet flag oil, chamomile oil, camphor oil, kanaga oil, cardamom oil, cassia oil, pine needle oil, copaiva balsam oil, coriander oil, spearmint oil, caraway oil, cumin oil, labdanum oil, lavender oil, lemongrass oil, linden blossom oil, lime oil, tangerine oil, lemon balm oil, mint oil, musk seed oil , muscatel oil, myrrh oil, clove oil, neroli oil, niaouli oil, olibanum oil, orange blossom oil, orange peel oil, origanum oil, Palmarosa Oil, Patchouli Oil, Peru Balsam Oil, Petitgrain Oil, Pepper Oil, Peppermint Oil, Allspice Oil, Pine Oil, Rose Oil, Rosemary Oil, Sage Oil, Sandalwood Oil, Celery Oil, Spike Oil, Star Anise Oil, Turpentine Oil, Thuja Oil, Thyme Oil, Verbena Oil, Vetiver Oil, Juniper Berry Oil, Wormwood Oil, Wintergreen Oil, Ylang Ylang oil, hyssop oil, cinnamon oil, cinnamon leaf oil, citronella oil, lemon oil and cypress oil as well as ambrettolide, ambroxan, alpha-amylcinnamaldehyde, anethole, anisaldehyde, anis alcohol, anisole, anthranilic acid methyl ester, acetophenone, benzylacetone, benzaldehyde, benzoic acid ethyl ester, benzophenone, benzyl alcohol, benzyl acetate, Benzyl benzoate, benzyl formate, benzyl valerate, borneol, bornyl acetate, Boisambrene forte, alpha-bromostyrene, n-decylaldehyde, n-dodecylaldehyde, eugenol, eugenol methyl ether, eucalyptol, farnesol, fenchone, fenchyl acetate, geranyl acetate, geranyl formate, heliotropin, heptine carboxylic acid methyl ester, heptaldehyde, hydroquinone dimethyl ether , Hydroxycinnamaldehyde, Hydroxycinnamyl Alcohol, Indole, Iron, Isoeugenol, Isoeugenolmeth yl ether, isosafrole, jasmone, camphor, karvakrol, karvone, p-cresol methyl ether, coumarin, p-methoxyacetophenone, methyl n-amyl ketone, methyl anthranilic acid methyl ester, p-methylacetophenone, methyl chavicol, p-methylquinoline, methyl beta-naphthyl ketone, methyl n- nonylacetaldehyde, methyl n-nonyl ketone, muskon, beta-naphthol ethyl ether, beta-naphthol methyl ether, nerol, n-nonyl aldehyde, nonyl alcohol, n-octyl aldehyde, p-oxy-acetophenone, pentadecanolide, beta-phenylethyl alcohol, phenylacetic acid, pulegone, safrole, Isoamyl salicylate, methyl salicylate, hexyl salicylate, cyclohexyl salicylate, santalol, sandelice, skatole, terpineol, thymen, thymol, troenane, gamma-undelactone, vanillin, veratrumaldehyde, cinnamic aldehyde, cinnamic alcohol, cinnamic acid, ethyl cinnamate, benzyl cinnamate, diphenyl oxide, limonene, linalool, linalyl acetate and propionate , melusate, menthol, menthone, methyl-n-heptenone, pinene, phenylacetaldehyde, terpinyl acetate, citral, citronellal, and mixtures thereof.

Mixtures of the substances mentioned can also be used.

• Kopfnote: Dampfdruck bei 25°C: >0,0133 kPa
• Herznote: Dampfdruck bei 25°C: 0,0133 bis 0,000133 kPa
• Basisnote: Dampfdruck bei 25°C: <0,000133 kPa

In order to be perceptible, a fragrance must be volatile, with the nature of the functional groups and the structure of the chemical compound also having an important role to play in terms of molecular weight. Thus, most fragrances have molar masses of up to about 200 daltons, while molar masses of 300 daltons and above tend to be an exception. Due to the different volatility of odorants, the odor of a perfume or fragrance composed of several odorants changes during evaporation, with the odor impressions being divided into "top note" (top note), "middle note" (middle note or body) and "base note" (end note or dry out). Analogous to the description in the international patent publication WO 2016/200761 A2 can top, middle and base notes based on their vapor pressure (using the in the WO 2016/200761 test methods described) can be classified as follows:

• Top note: Vapor pressure at 25°C: >0.0133 kPa
• Heart note: Vapor pressure at 25°C: 0.0133 to 0.000133 kPa
• Base note: Vapor pressure at 25°C: <0.000133 kPa

The adherent fragrances that can be used in the context of the present invention include, for example, the essential oils such as angelica root oil, anise oil, arnica flower oil, basil oil, bay oil, Bergamot oil, champaca blossom oil, noble fir oil, noble pine cone oil, elemi oil, eucalyptus oil, fennel oil, spruce needle oil, galbanum oil, geranium oil, ginger grass oil, guaiac wood oil, gurjun balm oil, helichrysum oil, ho oil, ginger oil, iris oil, cajeput oil, sweet flag oil, chamomile oil, camphor oil, kanaga oil, cardamom oil, cassia oil, Pine needle oil, copalva balsam oil, coriander oil, spearmint oil, cumin oil, cumin oil, lavender oil, lemongrass oil, lime oil, mandarine oil, lemon balm oil, musk seed oil, myrrh oil, clove oil, neroli oil, niaouli oil, olibanum oil, orange oil, origanum oil, palmarosa oil, patchouli oil, balsam of Peru, petitgrain oil, pepper oil, peppermint oil, Allspice oil, pine oil, rose oil, rosemary oil, sandalwood oil, celery oil, spike oil, star anise oil, turpentine oil, thuja oil, thyme oil, verbena oil, vetiver oil, juniper berry oil, wormwood oil, wintergreen oil, ylang ylang oil, hyssop oil, cinnamon oil, cinnamon leaf oil, citronella oil, lemon oil and cypress oil.

High-boiling or solid fragrances of natural or synthetic origin include, for example: ambrettolide, α-amylcinnamaldehyde, anethole, anisaldehyde, anisalcohol, anisole, methyl anthranilate, acetophenone, benzylacetone, benzaldehyde, ethyl benzoate, benzophenone, benzyl alcohol, benzyl acetate, benzyl benzoate, benzyl formate, benzyl valerate, borneol, Bornyl acetate, α-bromostyrene, n-decyl aldehyde, n-dodecyl aldehyde, eugenol, eugenol methyl ether, eucalyptol, farnesol, fenchone, fenchyl acetate, geranyl acetate, geranyl formate, heliotropin, heptine carboxylic acid methyl ester, heptaldehyde, hydroquinone dimethyl ether, hydroxycinnamaldehyde, hydroxycinnamic alcohol, indole, Iron, isoeugenol, isoeugenol methyl ether, isosafrole, jasmone, camphor, karvakrol, karvone, p-cresol methyl ether, coumarin, p-methoxyacetophenone, methyl-n-amyl ketone, methyl anthranilic acid methyl ester, p-methylacetophenone, methylchavicol, p-methylquinoline, methyl β-naphthyl ketone, methyl-n-nonyl acetaldehyde, methyl-n-nonyl ketone, muscone, β-Na Phthol ethyl ether, β-naphthol methyl ether, nerol, nitrobenzene, n-nonyl aldehyde, nonyl alcohol, n-octyl aldehyde, p-oxy-acetophenone, pentadecanolide, ß-phenyl ethyl alcohol, phenylacetaldehyde dimethyl acetal, phenylacetic acid, pulegone, safrole, salicylic acid isoamyl ester, salicylic acid methyl ester, salicylic acid hexyl ester, Cyclohexyl Salicylate, Santalol, Skatole, Terpineol, Thymen, Thymol, γ-Undelactone, Vaniline, Veratrumaldehyde, Cinnamaldehyde, Cimate alcohol, Cinnamic acid, Ethyl cinnamate, Benzyl cinnamate

The more volatile fragrances include, in particular, the lower-boiling fragrances of natural or synthetic origin, which can be used alone or in mixtures. Examples of more volatile fragrances are alkyl isothiocyanates (alkyl mustard oils), butanedione, limonene, linalool, linyl acetate and linyl propionate, menthol, menthone, methyl-n-heptenone, phellandrene, phenylacetaldehyde, terpinyl acetate, citral, citronellal.

Perfume compounds of the aldehyde type which can preferably be used are hydroxycitronellal ( CAS 107-75-5 ), helional ( CAS 1205-17-0 ), citral (5392-40-5), bourgeonal (18127-01-0), triplal ( CAS 27939-60-2 ), Ligustral ( CAS 68039-48-5 ), vertocitral ( CAS 68039-49-6 ), Florhydral ( CAS 125109-85-5 ), citronellal ( CAS 106-23-0 ), citronellyloxyacetaldehyde ( CAS 7492-67-3 ).

In addition or as an alternative to the fragrances mentioned above, the WO 2016/200761 A2 fragrances described, in particular those mentioned in Tables 1, 2 and 3 Perfumes, and the modulators listed in Tables 4a and 4b are used. This publication is incorporated herein by reference in its entirety.

1. (a) Textilpflegestoffe, wie vorzugsweise Silikonöle, und/oder
2. (b) Hautpflegestoffe, wie vorzugsweise Vitamin E, natürliche Öle und/oder kosmetische Öle.

A perfume oil can also be present in the form of a perfume oil preparation and can, for example, comprise at least one further active ingredient in oil form. In this context, suitable active substances in oil form are those which are suitable for washing, cleaning, care and/or finishing purposes, in particular

1. (a) Textile care substances, such as preferably silicone oils, and/or
2. (b) skin care substances, such as preferably vitamin E, natural oils and/or cosmetic oils.

1. a) Wachse wie beispielsweise Carnauba, Spermaceti, Bienenwachs, Lanolin und/oder Derivate derselben und andere.
2. b) Hydrophobe Pflanzenextrakte
3. c) Kohlenwasserstoffe wie beispielsweise Squalene und/oder Squalane
4. d) Höhere Fettsäuren, vorzugsweise solche mit wenigstens 12 Kohlenstoffatomen, beispielsweise Laurinsäure, Stearinsäure, Behensäure, Myristinsäure, Palmitinsäure, Ölsäure, Linolsäure, Linolensäure, Isostearinsäure und/oder mehrfach ungesättigte Fettsäuren und andere.
5. e) Höhere Fettalkohole, vorzugsweise solche mit wenigstens 12 Kohlenstoffatomen, beispielsweise Laurylalkohol, Cetylalkohol, Stearylalkohol, Oleylalkohol, Behenylalkohol, Cholesterol und/oder 2-Hexadecanaol und andere.
6. f) Ester, vorzugsweise solche wie Cetyloctanoate, Lauryllactate, Myristyllactate, Cetyllactate, Isopropylmyristate, Myristylmyristate, Isopropylpalmitate, Isopropyladipate, Butylstearate, Decyloleate, Cholesterolisostearate, Glycerolmonostearate, Glyceroldistearate, Glyceroltristearate, Alkyllactate, Alkylcitrate und/oder Alkyltartrate und andere.
7. g) Lipide wie beispielsweise Cholesterol, Ceramide und/oder Saccharoseester und andere.
8. h) Vitamine wie beispielsweise die Vitamine A, C und E, Vitaminalkylester, einschließlich Vitamin-C-Alkylester und andere.
9. i) Sonnenschutzmittel
10. j) Phospholipide
11. k) Derivate von alpha-Hydroxysäuren
12. l) Germizide für den kosmetischen Gebrauch, sowohl synthetische wie beispielsweise Salicylsäure und/oder andere als auch natürliche wie beispielsweise Neemöl und/oder andere.
13. m) Silikone
14. n) Natürliche Öle, z.B. Mandelöl

sowie Mischungen jeglicher vorgenannter Komponenten.Skin care actives are all those actives that impart a sensory and/or cosmetic benefit to the skin. Skin care active ingredients are preferably selected from the following substances:

1. a) Waxes such as carnauba, spermaceti, beeswax, lanolin and/or derivatives thereof and others.
2. b) Hydrophobic plant extracts
3. c) hydrocarbons such as squalene and/or squalane
4. d) Higher fatty acids, preferably those with at least 12 carbon atoms, for example lauric acid, stearic acid, behenic acid, myristic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid, isostearic acid and/or polyunsaturated fatty acids and others.
5. e) Higher fatty alcohols, preferably those with at least 12 carbon atoms, for example lauryl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, cholesterol and/or 2-hexadecanaol and others.
6. f) esters, preferably such as cetyl octanoate, lauryl lactate, myristyl lactate, cetyl lactate, isopropyl myristate, myristyl myristate, isopropyl palmitate, isopropyl adipate, butyl stearate, decyl oleate, cholesterol isostearate, glycerol monostearate, glycerol distearate, glycerol tristearate, alkyl lactate, alkyl citrate and/or alkyl tartar and others.
7. g) Lipids such as cholesterol, ceramides and/or sucrose esters and others.
8. h) Vitamins such as vitamins A, C and E, vitamin alkyl esters including vitamin C alkyl esters and others.
9. i) Sunscreens
10. j) phospholipids
11. k) Derivatives of alpha-hydroxy acids
12. l) Germicides for cosmetic use, both synthetic such as salicylic acid and/or others and natural such as neem oil and/or others.
13. m) silicones
14. n) Natural oils, eg almond oil

and mixtures of any of the aforementioned components.

In various embodiments, the content of such a fragrance, which can also be present in the form of a perfume oil or as a component of a perfume oil composition, is such as described above, preferably between about 0.0001 and 5% by weight, more preferably between about 0.001 and 3.0% by weight, preferably between about 0.005 and 1.5% by weight, even more preferably between about 0.01 and 1.0% by weight, for example about 0.001, 0.002, 0.003, 0.004, 0.005, 0.006, 0.007, 0.008, 0.009, 0.01, 0.02, 0.03, 0.04, 0.05, 0, 06, 0.07, 0.08, 0.09, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9 or 1.0% by weight, based in each case on the total weight of the agent according to the invention.

It may be desirable to keep sensitive benefit agents/active ingredients, such as perfumes and fragrances, as described above, physically separate from other ingredients of the agent until use. An elegant method for incorporating such sensitive, chemically or physically incompatible or volatile ingredients is the use of microcapsules in which these ingredients are enclosed in a stable manner for storage and transport and from which they are mechanically, chemically, thermally or enzymatically released for or during use .

"Microcapsule" as used herein refers to capsules with micron-scale core-shell morphology having a capsule shell that completely encloses a core. "Completely encloses" or "completely surrounds" as used herein in relation to the microcapsules means that the core is completely surrounded by the shell, i.e. in particular not embedded in a matrix in such a way that it is exposed at any point. It is further preferred that the capsule shell is designed in such a way that the release of the content is controlled, i.e. the content is not spontaneously released in an uncontrolled manner independently of a release stimulus. For this reason, the capsule shell is preferably essentially impermeable to the encapsulated contents. "Essentially impermeable", as used in this context, means that the contents of the capsule or individual ingredients cannot spontaneously penetrate the shell, but are released only by opening the capsule or optionally also via a diffusion process that takes place over a longer period of time can. The core can be solid, liquid and/or gas, but is preferably solid and/or liquid. The microcapsules are preferably essentially spherical and have diameters in the range from 0.01 to 1000 μm, in particular from 0.1 to 500 μm. Capsule shell and capsule core consist of different materials, in particular the capsule shell is preferably solid under standard conditions (20° C., 1013 mbar), the core preferably solid and/or liquid, in particular liquid.

As an encapsulation material for microcapsules suitable in the context of the present invention, e.g. B. high molecular weight compounds of animal or vegetable origin, z. B. Protein compounds (gelatine, albumin, casein), cellulose derivatives (methyl cellulose, ethyl cellulose, cellulose acetate, cellulose nitrate, carboxymethyl cellulose) and in particular synthetic polymers (e.g. polyamides, polyolefins, polyesters, polyurethanes, epoxy resins, silicone resins and condensation products of carbonyl and NH group-containing compounds) can be used. Specifically, the shell material can be selected from, for example, polyacrylates; polyethylene; polyamides; polystyrenes; polyisoprenes; polycarbonates; polyesters; polyureas; polyurethanes; polyolefins; polysaccharides; epoxy resins; vinyl polymers; urea crosslinked with formaldehyde or glutaraldehyde; melamine crosslinked with formaldehyde; Gelatin polyphosphate coacervates, optional crosslinked with glutaraldehyde; gelatin gum arabic coacervates; silicone resins; polyamines reacted with polyisocyanates; acrylate monomers polymerized by free radical polymerization; Silk; Wool; Gelatin; cellulose; proteins; and blends and copolymers of the foregoing. Polyacrylates, polyethylene, polyamides, polystyrenes, polyisoprenes, polycarbonates, polyesters, polyureas, polyurethanes, polyolefins, epoxy resins, vinyl polymers and urea and/or melamine crosslinked with formaldehyde or glutaraldehyde are particularly preferred.

In principle, the known microencapsulation processes are suitable for producing suitable microcapsules. B. the encapsulation of the encapsulated phase by encapsulation with film-forming polymers (as z. B. previously mentioned), which are reflected after emulsification and coacervation or interfacial polymerisation on the material to be encapsulated takes place. In relation to the present invention, the phase to be encapsulated is a benefit agent composition, preferably a perfume composition, usually in the form of a perfume oil.

The capsules can release the encapsulated benefit agents via a variety of mechanisms. In various embodiments of the present invention, for example, capsules that have a mechanically stable capsule shell, but which then becomes permeable to the contained agents due to one or more environmental influences, such as changes in temperature or ionic strength or the pH value of the surrounding medium, are used will. Stable capsule wall materials are also possible, through which the at least one beneficial agent, for example a perfume oil and possibly other beneficial agents, can diffuse over time. The capsules can preferably release the at least one beneficial agent contained in the event of a change in the pH value or the ionic strength of the environment, a change in temperature, exposure to light, diffusion and/or mechanical stress.

In a preferred embodiment of the present invention, the capsules are fragile, i.e. they can release entrapped agent due to mechanical stress such as friction, pressure or shear stress which ruptures the shell of the capsules. In another embodiment, the capsule is thermally unstable, i.e. enclosed substances can be released if the capsules are at a temperature of at least 70°C, preferably at least 60°C, preferably at least 50°C and in particular at least 40° C is exposed.

In another preferred embodiment, the capsule may become permeable to the enclosed benefit agent(s) after exposure to radiation of a certain wavelength, preferably exposure to sunlight.

It is also possible that the capsules are fragile and at the same time thermally unstable and/or unstable to radiation of a specific wavelength.

Suitable microcapsules can be water-soluble and/or water-insoluble, but the capsules are preferably water-insoluble. The water-insolubility of the capsules has the advantage that these washing, cleaning or other treatment applications can survive and are thus able to release the at least one beneficial agent only after the aqueous washing, cleaning or treatment process, such as during drying by a mere increase in temperature or by exposure to the sun or, in particular, by friction on the surface.

Particularly preferred are water-insoluble capsules that are ruptured by friction.

The term "friable" or "friction rupturable" capsules means, in particular, those capsules which, when attached to a surface treated therewith (e.g. textile surface), can be opened or ruptured by mechanical rubbing or by pressure, so that the contents can be released only as a result of a mechanical effect, e.g. if you dry your hands with a towel on which such capsules are deposited.

Advantageously usable, friable capsules can have an average diameter dso of <250 μm, preferably in the range from 1 to 100 μm, preferably between 3 and 95 μm, in particular between 4 and 90 μm, for example between 5 and 80 μm, for example between 5 and 40 have microns. The d ₅₀ value indicates the diameter that results when 50% by weight of the capsules have a smaller diameter and 50% by weight of the capsules have a larger diameter than the determined d ₅₀ value. It is furthermore preferred that the d ₉₀ value of the particle size distribution of the microcapsules is <70 μm, preferably <60 μm, particularly preferably <50 μm. The d ₉₀ value of the particle size distribution is the value at which 90% of all particles are smaller and 10% of the particles are larger than this value.

The core or (filled) cavity enclosing shell of the capsules preferably has an average thickness in the range between about 50 and 500 nm, preferably between about 100 nm and about 250 nm specified ranges relating to the mean diameter and relating to the average thickness.

The d ₅₀ value indicates the diameter that results when 50% by weight of the capsules have a smaller diameter and 50% by weight of the capsules have a larger diameter than the determined d ₅₀ value. It is furthermore preferred that the d ₉₀ value of the particle size distribution of the microcapsules is <70 μm, preferably <60 μm, particularly preferably <50 μm. The d ₉₀ value of the particle size distribution is the value at which 90% of all particles are smaller and 10% of the particles are larger than this value.

The diameter of the capsules or the particle size of the microcapsules can be determined using customary methods. It can be determined, for example, with the aid of dynamic light scattering, which is usually carried out on dilute suspensions containing, for example, 0.01 to 1% by weight of capsules. can be carried out. It can also be done by evaluating light microscopic or electron microscopic images of capsules.

In various embodiments, a microcapsule according to the invention has an average diameter dso of approximately 1 to 80 μm, preferably approximately 5 to 40 μm, in particular approximately 20 to 35 μm, for example approximately 22 to approximately 33 μm.

The wall material of the microcapsules preferably comprises polyurethanes, polyolefins, polyamides, polyesters, polysaccharides, epoxy resins, silicone resins and/or polycondensation products from carbonyl compounds and compounds containing NH groups. This corresponds to a preferred embodiment of the invention. For example, melamine-urea-formaldehyde microcapsules or melamine-formaldehyde microcapsules or urea-formaldehyde microcapsules can preferably be used. Microcapsules based on melamine-formaldehyde resins are particularly preferred.

The general procedure for microcapsule manufacture as such has long been well known to those skilled in the art. Particularly suitable methods for microcapsule production are in principle z. Am U.S. 3,516,941 , in U.S. 3,415,758 or also in EP 0 026 914 A1 described. The latter describes, for example, microcapsule production by acid-induced condensation of melamine-formaldehyde precondensates and/or their C1-C4-alkyl ethers in water, in which the hydrophobic material forming the capsule core is dispersed, in the presence of a protective colloid.

Suitable thickeners include, for example, Aerosil types (hydrophilic silicic acids), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose, methyl cellulose, hydroxypropyl, hydroxypropylmethyl and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono - and diesters of fatty acids, polyacrylates (e.g. Carbopole ^® from Goodrich or Synthalene ^® from Sigma), polyacrylamides, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with concentrated Homolog distribution or alkyl oligoglucosides and electrolytes such as common salt and ammonium chloride.

In various embodiments, the at least one thickener is a nonionic thickener, in particular selected from the group consisting of hydroxyethyl cellulose (HEC), hydroxypropyl cellulose (HPC), hydroxypropylmethyl cellulose (HPMC), methyl cellulose (MC), guar, guar derivatives (such as Jaguar HP105 ( Rhodia); hydroxypropyl guar) and mixtures of the aforementioned nonionic thickeners.

Alternatively, cationic thickeners can also be used. Examples of suitable cationic thickeners include, for example, those available under the tradename Rheavis ^® CSP (BASF). In various embodiments, the at least one nonionic or cationic thickener is present in the composition in an amount of 0.1 to 10% by weight, based on the total weight of the formulation.

In various embodiments of the invention, the agent contains at least one emulsifier. The at least one emulsifier is preferably a nonionic emulsifier and has an HLB value of at least 12.0, preferably at least 13.0, more preferably at least 14.0 and most preferably at least 15.0.

The term "HLB" (hydrophilic-lipophilic balance) defines the hydrophilic and lipophilic proportion of corresponding substance classes (here emulsifiers) in a value range from 1 to 20 according to the following formula (Griffin, Classification of surface active agents by HLB, J. Soc. cosmetics Chem. 1, 1949 ): HLB = 20 x (1 - (M1 /M)) where M = molar mass of the entire molecule and M1 = molar mass of the lipophilic portion of the molecule.

Low HLB values (≥ 1) describe lipophilic substances, high HLB values (≤ 20) describe hydrophilic substances. For example, defoamers typically have HLB values in the range of 1.5 to 3 and are insoluble in water. Emulsifiers for w/o emulsions typically have HLB values in the range 3-8, whereas emulsifiers for o/w emulsions typically have HLB values in the range 8-18. Detergents typically have HLB values in the range of 13-15 and solubilizers in the range of 12-18.

• Anlagerungsprodukte von 2 bis 50 Mol Ethylen-oxid und/ oder 0 bis 5 Mol Propylenoxid an lineare Fettalkohole mit 8 bis 22 C-Atomen, an Fettsäuren mit 8 bis 22 C-Atomen, an Alkylphenole mit 8 bis 15 C-Atomen in der Alkylgruppe sowie Alkylamine mit 8 bis 22 Kohlenstoffatomen im Alkylrest; Alkyl-und/oder Alkenyloligoglykoside mit 8 bis 22 Kohlenstoffatomen im Alk(en)ylrest und deren ethoxylierte Analoga;
• Anlagerungsprodukte von 1 bis 15 Mol Ethylen-oxid an Ricinusöl und/oder gehärtetes Ricinusöl;
• Anlagerungsprodukte von 15 bis 60 Mol Ethylenoxid an Ricinusöl und/oder gehärtetes Ricinusöl; Partialester von Glycerin und/oder Sorbitan mit ungesättigten, linearen oder gesättigten, verzweigten Fettsäuren mit 12 bis 22 Kohlenstoffatomen und/oder Hydroxycarbonsäuren mit 3 bis 18 Kohlenstoffatomen sowie deren Addukte mit 1 bis 30 Mol Ethylenoxid; Partialester von Polyglycerin (durchschnittlicher Eigenkondensations-grad 2 bis 8), Polyethylenglycol (Molekularge-wicht 200 bis 5000), Trimethylolpropan, Pentae-rythrit, Zuckeralkoholen (z.B. Sorbit), Alkylglucosiden (z.B. Methylglucosid, Butylglucosid, Laurylglucosid) sowie Polyglucosiden (z.B. Cellulose) mit gesättigten und/oder ungesättigten, linearen oder verzweigten Fettsäuren mit 12 bis 22 Kohlenstoff-atomen und/oder Hydroxycarbonsäuren mit 3 bis 18 Kohlenstoffatomen sowie deren Addukte mit 1 bis 30 Mol Ethylenoxid;
• Mischester aus Pentaerythrit, Fettsäuren, Citronensäure und Fettalkohol gemäß DE 1165574 PS und/oder Mischester von Fettsäuren mit 6 bis 22 Kohlenstoffatomen, Methylglucose und Polyolen, vorzugsweise Glycerin oder Polyglycerin.
• Mono-, Di- und Trialkylphosphate sowie Mono-, Di- und/oder Tri-PEG-alkylphosphate und deren Salze;
• Wollwachsalkohole;
• Polysiloxan-Polyalkyl-Polyether-Copolymere bzw. entsprechende Derivate sowie
• Polyalkylenglycole.

The following nonionic emulsifiers, for example, are suitable as nonionic emulsifiers for the agents according to the invention, without the invention being restricted to these:

• Adducts of 2 to 50 moles of ethylene oxide and/or 0 to 5 moles of propylene oxide onto linear fatty alcohols containing 8 to 22 carbon atoms, onto fatty acids containing 8 to 22 carbon atoms, onto alkylphenols containing 8 to 15 carbon atoms in the alkyl group and alkylamines having 8 to 22 carbon atoms in the alkyl radical; Alkyl and/or alkenyl oligoglycosides having 8 to 22 carbon atoms in the alk(en)yl radical and their ethoxylated analogues;
• Addition products of 1 to 15 moles of ethylene oxide with castor oil and/or hydrogenated castor oil;
• Addition products of 15 to 60 moles of ethylene oxide with castor oil and/or hydrogenated castor oil; Partial esters of glycerol and/or sorbitan with unsaturated, linear or saturated, branched fatty acids having 12 to 22 carbon atoms and/or hydroxycarboxylic acids having 3 to 18 carbon atoms and their adducts with 1 to 30 moles of ethylene oxide; Partial esters of polyglycerol (average degree of self-condensation 2 to 8), polyethylene glycol (molecular weight 200 to 5000), trimethylolpropane, pentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (e.g. cellulose) with saturated and/or unsaturated, linear or branched fatty acids having 12 to 22 carbon atoms and/or hydroxycarboxylic acids having 3 to 18 carbon atoms and their adducts with 1 to 30 moles of ethylene oxide;
• Mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol UK 1165574 PS and/or mixed esters of fatty acids with 6 to 22 carbon atoms, methyl glucose and polyols, preferably glycerol or polyglycerol.
• Mono-, di- and tri-alkyl phosphates and mono-, di- and/or tri-PEG-alkyl phosphates and their salts;
• wool wax alcohols;
• Polysiloxane-polyalkyl polyether copolymers or corresponding derivatives and
• polyalkylene glycols.

The addition products of ethylene oxide and/or propylene oxide onto fatty alcohols, fatty acids, alkylphenols or castor oil are known, commercially available products. These are homologous mixtures whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and/or propylene oxide and substrate, with which the addition reaction is carried out corresponds. C12/18 fatty acid mono- and diesters of addition products of ethylene oxide to glycerol are from DE 2024051 PS is known as a refatting agent for cosmetic preparations.

Alkyl and/or alkenyl oligoglycosides, their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols having 8 to 18 carbon atoms. With regard to the glycoside residue, both monoglycosides, in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol, and oligomeric glycosides with a degree of oligomerization of preferably up to about 8 are suitable. The degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.

Typical examples of suitable partial glycerides are hydroxystearic hydroxystearic acid diglyceride, isostearic acid, Isostearinsäurediglycerid monoglyceride, oleic acid diglyceride, Ricinolsäuremoglycerid, Ricinolsäurediglycerid, Linolsäuremonoglycerid, Linolsäurediglycerid, Linolensäuremonoglycerid, Linolensäurediglycerid, Erucasäuremonoglycerid, E-rucasäurediglycerid, Weinsäuremonoglycerid, Weinsäurediglycerid, Citronensäuremonoglycerid, Citronendiglycerid, Äpfelsäuremonoglycerid, Apfelsäurediglycerid well as their technical Mixtures that may contain small amounts of triglycerides as a result of the manufacturing process. Addition products of 1 to 30, preferably 5 to 10, moles of ethylene oxide onto the partial glycerides mentioned are also suitable.

As sorbitan esters sorbitan-noisostearat, sorbitan sesquiisostearate, uitartrat Sorbitan, sorbitan triisostearate, sorbitan monooleate, sorbitan, sorbitan, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonoricinoleat, Sorbitansesquiricinoleat, Sorbitandiricinoleat, Sorbitantriricinoleat, Sorbitanmonohydroxystearat, Sorbitansesquihydroxystearat, Sorbitandihydroxystearat, Sorbitantrihydroxystearat, Sorbitanmonotartrat, Sorbitansesq, Sorbitan itartrate, sorbitan tritartrate, sorbitan monocitrate, sorbitan sesquicitrate, sorbitan citrate, sorbitan tricitrate, Sorbitan monomaleate, sorbitan sesquimaleate, sorbitan dimaleate, sorbitan trimaleate and technical mixtures thereof. Addition products of 1 to 30, preferably 5 to 10, moles of ethylene oxide onto the sorbitan esters mentioned are also suitable.

Typical examples of suitable polyglycerol esters are polyglyceryl-2 dipolyhydroxystearates ( ^Dehymuls® PGPH), polyglycerol-3-diisostearates ( ^Lameform® TGI), polyglyceryl-4 isostearates ( ^Isolan® GI 34), polyglyceryl-3 oleates, diisostearoyl polyglyceryl-3 diisostearates (Isolan ^® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care ^® 450), Polyglyceryl-3 Beeswax (Cera Bellina ^® ), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010/90), Polyglyceryl-3 Cetyl Ether (Chimexane ^® NL) , Polyglyceryl-3 distearate (Cremophor ^® GS 32) and polyglyceryl polyricinoleate (Admul ^® WOL 1403) polyglyceryl dimerate isostearate and mixtures thereof.

Examples of other suitable polyol esters are the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like, optionally reacted with 1 to 30 moles of ethylene oxide.

Instead of or in addition to the at least one nonionic emulsifier, the agent according to the invention can also contain other emulsifiers, for example cationic or anionic emulsifiers.

The known cationic emulsifiers include fatty acid amidoamines and/or their quaternization products.

Fatty acid amidoamines which are suitable as cationic emulsifiers are condensation products of fatty acids with optionally ethoxylated di- or oligoamines which preferably follow the formula (II), R ¹ CO-NR ² -[(A)-NR ³ ] _n -R ⁴ (II) in which R ¹ CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, R ² is hydrogen or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms, R ³ and R ⁴ are each independently hydrogen , a (CH ₂ CH ₂ O) _m H group or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms, A is a linear or branched alkylene group having 1 to 6 carbon atoms, n is a number from 1 to 4 and m is a number from 1 up to 30. Typical examples are condensation products of caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, eleostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures with ethylenediamine, propylenediamine, diethylenetriamine, dipropylenetriamine, triethylenetetramine, tripropylenetetramine and their adducts with 1 to 30, preferably 5 to 15 and in particular 8 to 12 mol ethylene oxide. The use of ethoxylated fatty acid amidoamines is preferred because in this way the hydrophilicity of the emulsifiers can be adjusted exactly to the active ingredients to be emulsified.

Instead of the fatty acid amidoamines, it is also possible to use their quaternization products, which are obtained by reacting the amidoamines with suitable alkylating agents, such as, for example, methyl chloride or, in particular, dimethyl sulfate, using processes known per se. The quaternization products preferably follow the formula (III), [R ¹ CO-NR ² - [(A) -N ⁺ R ³ R ⁶ ) _n -R ⁴ ]X ^- (III), in which R ¹ CO represents a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, R ² is hydrogen or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms, R ³ is hydrogen, a (CH ₂ CH ₂ O) _m H group or an optionally hydroxy-substituted alkyl radical 1 to 4 carbon atoms, R ⁴ is R ¹ CO, hydrogen, a (CH ₂ CH ₂ O) _m H group or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms, R ⁶ is an alkyl radical having 1 to 4 carbon atoms, A is a linear or branched alkylene group having 1 to 6 carbon atoms, n is a number from 1 to 4, m is a number from 1 to 30 and X is halide, especially chloride, or alkyl sulfate, preferably methyl sulfate. Suitable for this purpose are, for example, the methylation products of the preferred fatty acid amidoamines already mentioned above. Furthermore, mixtures of fatty acid amidoamines and their quaternization products can also be used, which are particularly easy to prepare by not carrying out the quaternization completely, but only to a desired degree.

The agent can contain the fatty acid amidoamines and/or their quaternization products in amounts of 0.1% by weight to 50% by weight, preferably 1% by weight to 30% by weight and in particular 2% by weight to 10% by weight. -% - based on the final concentration - included.

Other known emulsifiers include the betaines. Betaines are known surfactants which are mainly produced by carboxyalkylation, preferably carboxymethylation, of amine compounds. The starting materials are preferably condensed with halocarboxylic acids or their salts, in particular with sodium chloroacetate, one mole of salt being formed per mole of betaine. Furthermore, the addition of unsaturated carboxylic acids, such as acrylic acid, is also possible. For the nomenclature and in particular for the distinction between betaines and "true" amphoteric surfactants, see the article by U. Ploog in Seifen-Ole-Fette-Wachse, 108, 373 (1982 ) referenced. Further overviews on this topic can be found, for example, by A.O'Lennick et al. in HAP-PI, Nov. 70 (1986 ), S.Holzman et al. in Tens. surf Det. 23, 309 (1986 ), R. Bibo et al. in Soap Cosm. Chem.Spec, Apr. 46 (1990 ) and P.Ellis et al. in euros Cosm. 1, 14 (1994 ). Examples of suitable betaines are the carboxyalkylation products of secondary and especially tertiary amines which follow the formula (IV), R ⁷ -N ⁺ (R ⁸ )(R ⁹ )-(CH ₂ ) _p COOA (IV) where R ⁷ for alkyl and/or alkenyl radicals having 6 to 22 carbon atoms, R ⁸ for hydrogen or alkyl radicals with 1 to 4 carbon atoms, R ⁹ for alkyl radicals with 1 to 4 carbon atoms, p for numbers from 1 to 6 and A for an alkali - and/or alkaline earth metal or ammonium. Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, dodecylmethylamine, dodecyldimethylamine, dodecylethylmethylamine, C _12/14 cocoalkyldimethylamine, myristyldimethylamine, cetyldimethylamine, stearyldimethylamine, Stearylethylmethylamine, oleyldimethylamine, C _16/18 -tallow alkyldimethylamine and technical mixtures thereof.

Also suitable are carboxyalkylation products of amidoamines which follow the formula (V), R ¹⁰ CO-NH-(CH ₂ ) _m -N ⁺ (R ⁸ )(R ⁹ )-(CH ₂ ) _p COOA (V), in which R ¹⁰ CO is an aliphatic acyl radical having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds, m is a number from 1 to 3 and R ³ , R ⁹ , p and A are as defined above. Typical examples are reaction products of fatty acids having 6 to 22 carbon atoms, namely caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, eleostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid as well their technical mixtures, with N,N-dimethylaminoethylamine, N,N-dimethylaminopropylamine, N,N-diethylaminoethylamine and N,N-diethylaminopropylamine, which are condensed with sodium chloroacetate. Preference is given to using a condensation product of C _8/18 coconut fatty acid N,N-dimethylaminopropylamide with sodium chloroacetate.

in der R⁵ für einen Alkylrest mit 5 bis 21 Kohlenstoffatomen, R⁶ für eine Hydroxylgruppe, einen OCOR⁵- oder NHCOR⁵-Rest und m für 2 oder 3 steht. Auch bei diesen Substanzen handelt es sich um bekannte Stoffe, die beispielsweise durch cyclisierende Kondensation von 1 oder 2 Mol Fettsäure mit mehrwertigen Aminen, wie beispielsweise Aminoethylethanolamin (AEEA) oder Diethylentriamin erhalten werden können. Die entsprechenden Carboxyalkylierungs-produkte stellen Gemische unterschiedlicher offenkettiger Betaine dar. Typische Beispiele sind Kondensationsprodukte der oben genannten Fettsäuren mit AEEA, vorzugsweise Imidazoline auf Basis von Laurinsäure oder wiederum C_12/14-Kokosfettsäure, die anschließend mit Natriumchloracetat betainisiert werden.Furthermore, suitable starting materials are also imidazolines which follow the formula (VI),

in which R ⁵ is an alkyl group having 5 to 21 carbon atoms, R ⁶ is a hydroxyl group, an OCOR ⁵ or NHCOR ⁵ group and m is 2 or 3. These substances are also known substances which can be obtained, for example, by cyclizing condensation of 1 or 2 moles of fatty acid with polyvalent amines, such as aminoethylethanolamine (AEEA) or diethylenetriamine. The corresponding carboxyalkylation products are mixtures of different open-chain betaines. Typical examples are condensation products of the abovementioned fatty acids with AEEA, preferably imidazolines based on lauric acid or, in turn, C _12/14 coconut fatty acid, which are then betainized with sodium chloroacetate.

A composition according to the invention can contain the betaines in amounts of 0.1 to 50% by weight, preferably 1 to 30% by weight and in particular 2 to 10% by weight, based on the final concentration.

The agent according to the invention may contain combinations of nonionic emulsifiers with other nonionic emulsifiers, anionic emulsifiers and/or cationic emulsifiers, the HLB value of the emulsifier mixture of the (at least one) first and (at least one) second emulsifier preferably being at least 12, 0, more preferably at least 14.0, most preferably at least 15.0. Preferably the ratio of the first is Emulsifier to the second emulsifier while 0.9 to 0.1 to 0.9 to 0.1. In a particularly preferred embodiment, the second emulsifier is also a nonionic emulsifier.

In various embodiments, the agent also contains at least one non-aqueous solvent selected from (poly)alkylene glycols or alcohols, for example from the group of mono- or polyhydric alcohols. Alkanolamines or glycol ethers are also suitable, provided they are miscible with water in the concentration range used. The solvents are preferably selected from ethanol, n- or i-propanol, butanols, glycol, propane or butanediol, glycerol, diglycol, propyl or butyl diglycol, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol propyl ether, ethylene glycol monobutyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, propylene glycol methyl, ethyl or propyl ether, dipropylene glycol methyl or ethyl ether, methoxy, ethoxy or butoxytriglycol, 1-butoxyethoxy-2-propanol, 3-methyl-3-methoxybutanol, propylene glycol tbutyl ether, and mixtures of these solvents. In preferred embodiments, the at least one non-aqueous solvent is selected from ethanol, propylene glycol, dipropylene glycol, glycerol and isopropanol.

In further embodiments, the agent also contains at least one hydrotrope. According to the invention, suitable hydrotropes are, in particular, aromatic alkyl sulfonates, such as in particular toluene sulfonates, cumene sulfonates, xylene sulfonates and others. In various embodiments, the at least one hydrotrope is in particular an aromatic alkylsulfonic acid or an ester or salt thereof, preferably selected from p-toluenesulfonic acid methyl ester, p-toluenesulfonic acid monohydrate and p-cumenesulfonic acid or the corresponding salts, in particular the sodium salts.

In order to bring the pH of the agent according to the invention into the desired range, the use of pH adjusters can be indicated. All known acids or bases can be used here, provided that their use is not prohibited for technical or ecological reasons or for reasons of consumer protection. The amount of these extenders does not usually exceed 1% by weight of the total formulation.

Colorants are added to the composition of the invention to improve the aesthetic appeal of the product and to provide the consumer with a visually "typical and distinctive" product. The content of dyes is usually less than 0.01% by weight of the composition formulation. Preferred dyes, the selection of which presents no difficulty to the person skilled in the art, have a high storage stability and are insensitive to the other ingredients of the agents and to light, and do not have any pronounced substantivity to textile fibers so as not to stain them.

Foam inhibitors that can be used in the agent according to the invention are, for example, soaps, paraffins or silicone oils, which can optionally be applied to carrier materials. Suitable antiredeposition agents, also referred to as soil repellents are, for example, nonionic cellulose ethers, such as methylcellulose and methylhydroxypropylcellulose, with a proportion of 15 to 30% by weight of methoxy groups and 1 to 15% by weight of hydroxypropyl groups, based in each case on the nonionic cellulose ether and those from the prior art known polymers of phthalic acid and/or terephthalic acid or derivatives thereof, in particular polymers of ethylene terephthalates and/or polyethylene glycol terephthalates or anionically and/or nonionically modified derivatives of these. Particularly preferred of these are the sulfonated derivatives of the phthalic and terephthalic acid polymers.

• Glycerin,
• Alkylenglycole, wie beispielsweise Ethylenglycol, Diethylenglycol, Propylenglycol, Butylenglycol, Hexylenglycol sowie Polyethylenglycole mit einem durchschnittlichen Molekulargewicht von 100 bis 1 000 Dalton,
• technische Oligoglycengemische mit einem Eigenkondensationsgrad von 1,5 bis 10 wie etwa technische Diglycengemische mit einem Diglycengehalt von 40 bis 50 Gew -%,
• Methyolverbindungen, wie insbesondere Trimethylolethan, Trimethylolpropan, Trimethylolbutan Pentaerythrit und Dipentaerythrit,
• Niedrigalkylglucoside, insbesondere solche mit 1 bis 8 Kohlenstoffen im Alkylrest, wie beispielsweise Methyl- und Butylglucosid,
• Zuckeralkohole mit 5 bis 12 Kohlenstoffatomen, wie beispielsweise Sorbit oder Mannit,
• Zucker mit 5 bis 12 Kohlenstoffatomen, wie beispielsweise Glucose oder Saccharose,
• Aminozucker, wie beispielsweise Glucamin,
• Dialkoholamine, wie Diethanolamin oder 2-Ami-no-1,3-propandiol.

To improve the flow behavior, other hydrotropes, such as ethanol, isopropyl alcohol or polyols, can be used in addition to those mentioned above. Polyols contemplated herein preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. The polyols can also contain other functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are:

• glycerin,
• Alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1000 daltons,
• technical oligoglycene mixtures with an inherent degree of condensation of 1.5 to 10 such as technical diglycene mixtures with a diglycene content of 40 to 50% by weight,
• Methylol compounds, such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol,
• Lower alkyl glucosides, especially those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside,
• Sugar alcohols with 5 to 12 carbon atoms, such as sorbitol or mannitol,
• Sugars with 5 to 12 carbon atoms, such as glucose or sucrose,
• Amino sugars such as glucamine,
• Dialcohol amines such as diethanolamine or 2-amino-1,3-propanediol.

Suitable enzymes are in particular those from the class of hydrolases, such as proteases, esterases, lipases or lipolytic enzymes, amylases, cellulases or other glycosyl hydrolases and mixtures of the enzymes mentioned. All of these hydrolases contribute to the removal of soiling such as protein, fat or starchy soiling and graying in the wash. Cellulases and other glycosyl hydrolases can also help to retain the color and increase the softness of the textile by removing pilling and microfibrils. Oxyreductases can also be used to bleach or to inhibit color transfer. Enzymatic active ingredients obtained from bacterial strains or fungi such as Bacillus subtilis, Bacillus licheniformis, Streptomyceus griseus and Humicola insolens are particularly suitable. Proteases of the subtilisin type and in particular proteases which are obtained from Bacillus lentus are preferably used. Here, enzyme mixtures, for example of protease and amylase or protease and lipase or lipolytic acting enzymes or protease and cellulase or from cellulase and lipase or lipolytic enzymes or from protease, amylase and lipase or lipolytic enzymes or protease, lipase or lipolytic enzymes and cellulase, but in particular protease and/or lipase-containing mixtures or Mixtures with lipolytic enzymes are of particular interest. Examples of such lipolytic enzymes are the known cutinases. Peroxidases or oxidases have also proven to be suitable in some cases. Suitable amylases include in particular α-amylases, iso-amylases, pullulanases and pectinases. Cellobiohydrolases, endoglucanases and β-glucosidases, which are also called cellobiases, or mixtures of these are preferably used as cellulases. Since different types of cellulase differ in their CMCase and Avicelase activities, the desired activities can be set by mixing the cellulases in a targeted manner.

The enzymes can be adsorbed on carriers or embedded in encapsulating substances in order to protect them against premature decomposition. The proportion of the enzymes, enzyme mixtures or enzyme granules can be, for example, about 0.1 to 5% by weight, preferably 0.12 to about 2% by weight.

Optical brighteners (so-called “whiteners”) can be added to the agents according to the invention in order to eliminate graying and yellowing of the treated textiles. These substances attach to the fiber and cause lightening and feigned bleaching by converting invisible ultraviolet radiation into visible longer wavelength light, with the ultraviolet light absorbed from sunlight being emitted as a faint bluish fluorescence and pure with the yellow hue of graying or yellowed laundry results in white. Suitable compounds come, for example, from the substance classes of 4,4'-diamino-2,2'-stilbenedisulfonic acids (flavonic acids), 4,4'-distyrylbiphenylene, methylumbelliferones, coumarins, dihydroquinolinones, 1,3-diarylpyrazolines, naphthalic acid imides, benzoxazole , benzisoxazole and benzimidazole systems as well as pyrene derivatives substituted by heterocycles. The optical brighteners are usually used in amounts of between 0.1% by weight and 0.3% by weight, based on the finished agent.

The task of graying inhibitors is to keep the dirt that has been detached from the fibers suspended in the liquor and thus prevent the dirt from being reattached. Water-soluble colloids of mostly organic nature are suitable for this purpose, for example the water-soluble salts of polymeric carboxylic acids, glue, gelatin, salts of ether sulfonic acids of starch or cellulose or salts of acidic sulfuric acid esters of cellulose or starch. Water-soluble polyamides containing acidic groups are also suitable for this purpose. Soluble starch preparations and starch products other than those mentioned above, such as degraded starches, aldehyde starches, etc., can also be used.

However, cellulose ethers such as carboxymethyl cellulose (Na salt), methyl cellulose, hydroxyalkyl cellulose and mixed ethers such as methyl hydroxyethyl cellulose, methyl hydroxypropyl cellulose, methyl carboxymethyl cellulose and mixtures thereof are preferably used in amounts of 0.1 to 5% by weight, based on the formulation of the agent.

Since textile fabrics, in particular made of rayon, viscose staple, cotton and mixtures thereof, can tend to wrinkle because the individual fibers are sensitive to bending, kinking, pressing and squeezing transversely to the fiber direction, the agents according to the invention can contain synthetic anti-crease agents. These include, for example, synthetic products based on fatty acids, fatty acid esters. Fatty acid amides, alkylol esters, alkylolamides or fatty alcohols, which are usually reacted with ethylene oxide, or products based on lecithin or modified phosphoric acid esters.

To combat microorganisms, the agent can contain antimicrobial agents. Depending on the antimicrobial spectrum and mechanism of action, a distinction is made between bacteriostatics and bactericides, fungistatics and fungicides, etc. Important substances from these groups are, for example, benzalkonium chlorides. Preferred compounds within the scope of the present invention are, for example, alkyl aryl sulfonates, halophenols and phenolmercuric acetate, although these compounds can also be dispensed with entirely in the agents according to the invention.

The agent according to the invention can contain preservatives, with preference being given to using only those which have little or no skin-sensitizing potential. Examples are sorbic acid and its salts, benzoic acid and its salts, salicylic acid and its salts, phenoxyethanol, 3-iodo-2-propynylbutylcarbamate, sodium N-(hydroxymethyl)glycinate, biphenyl-2-ol, and mixtures thereof. A suitable preservative is the solvent-free, aqueous combination of diazolidinyl urea, sodium benzoate and potassium sorbate (available as Euxyl ^® K 500 from Schuelke & Mayr), which can be used in a pH range of up to 7. In particular, preservatives based on organic acids and/or their salts are suitable for preserving the agent.

In order to prevent undesired changes to the agent according to the invention and/or the treated textile fabrics caused by the action of oxygen and other oxidative processes, the agent can contain antioxidants. This class of compounds includes, for example, substituted phenols, hydroquinones, catechols and aromatic amines as well as organic sulfides, polysulfides, dithiocarbamates, phosphites, phosphonates and vitamin E.

Increased wearing comfort can result from the additional use of antistatic agents, which are additionally added to the agent according to the invention. Antistatic agents increase the surface conductivity and thus enable an improved flow of charges that have formed. External antistatic agents are generally substances with at least one hydrophilic molecular ligand and form a more or less hygroscopic film on the surface. These mostly surface-active antistatic agents can be divided into nitrogen-containing (amines, amides, quaternary ammonium compounds), phosphorus-containing (phosphoric esters) and sulfur-containing (alkyl sulfonates, alkyl sulfates) antistatic agents. External antistatic agents are, for example, in the patent applications FR 1,156,513 , GB 873 214 and GB 839 407 described. The lauryl (or Stearyl)dimethylbenzylammonium chlorides are suitable as antistatic agents for textiles, with an additional finishing effect being achieved.

The agent according to the invention can also contain UV absorbers which are absorbed by the treated textiles and improve the lightfastness of the fibers. Compounds which have these desired properties are, for example, the compounds and derivatives of benzophenone having substituents in the 2- and/or 4-position which are effective through radiationless deactivation. Also suitable are substituted benzotriazoles, acrylates phenyl-substituted in the 3-position (cinnamic acid derivatives), optionally with cyano groups in the 2-position, salicylates, organic Ni complexes and natural substances such as umbelliferone and endogenous urocanic acid.

In order to effectively suppress dye detachment and/or dye transfer to other textile fabrics during the conditioning of dyed textile fabrics, a composition according to the invention can contain a dye transfer inhibitor. It is preferred that the dye transfer inhibitor is a polymer or copolymer of cyclic amines such as vinyl pyrrolidone and/or vinyl imidazole. Polymers useful as dye transfer inhibitors include polyvinylpyrrolidone (PVP), polyvinylimidazole (PVI), copolymers of vinylpyrrolidone and vinylimidazole (PVP/PVI), polyvinylpyridine N-oxide, poly-N-carboxymethyl-4-vinylpyridium chloride, and mixtures from it. Polyvinylpyrrolidone (PVP), polyvinylimidazole (PVI) or copolymers of vinylpyrrolidone and vinylimidazole (PVP/PVI) are particularly preferably used as color transfer inhibitors. 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. A PVP/PVI copolymer is commercially available, for example from BASF under the name ^Sokalan® HP 56.

The amount of color transfer inhibitor, based on the total amount of the composition, is preferably from 0.01% by weight to 2% by weight, preferably from 0.05% by weight to 1% by weight and more preferably from 0. 1% to 0.5% by weight.

Alternatively, however, enzymatic systems comprising a peroxidase and hydrogen peroxide or a substance that yields hydrogen peroxide in water can also be used as color transfer inhibitor. The addition of a mediator compound for the peroxidase, for example an acetosyringone, a phenol derivative or a phenotiazine or phenoxazine, is preferred in this case, it also being possible to use the polymeric color transfer inhibitors mentioned above.

Substances that complex heavy metals can be used to avoid the decomposition of certain ingredients catalyzed by heavy metals. Suitable heavy metal complexing agents are, for example, the alkali metal salts of ethylenediaminetetraacetic acid (EDTA) or nitrilotriacetic acid (NTA) and alkali metal salts of anionic polyelectrolytes such as polymaleates and polysulfonates.

A preferred class of complexing agents are the phosphonates, which are present in preferred agents in amounts of 0.01% by weight to 2.5% by weight, preferably 0.02% by weight to 2% by weight and in particular from 0 .03% by weight to 1.5% by weight are contained. These preferred compounds include, in particular, organophosphonates such as 1-hydroxyethane-1,1-diphosphonic acid (HEDP), aminotri(methylenephosphonic acid) (ATMP), diethylenetriaminepenta(methylenephosphonic acid) (DTPMP or DETPMP) and 2-phosphonobutane-1,2,4 -tricarboxylic acid (PBS-AM), which are mostly used in the form of their ammonium or alkali metal salts.

In some embodiments, the textile treatment agents described herein are preferably prepackaged to form dosage units. These dosing units preferably include the amount of washing or care-active substances required for one cleaning cycle. In some embodiments, suitable dosage units have a weight between 12 and 30 g, for example. The volume of the aforementioned dosing units and their three-dimensional shape are selected with particular preference in such a way that the prefabricated units can be dosed via the dosing chamber of a washing machine. The volume of the dosage unit is therefore preferably between 10 and 35 ml, preferably between 12 and 30 ml.

The agents according to the invention, in particular the prefabricated dosage units, particularly preferably have a water-soluble coating. In some embodiments, a composition as described herein is in the form of a unit dose as previously described. In preferred embodiments, such an agent according to the invention is in particular encased in a water-soluble film.

The water-soluble cover is preferably formed from a water-soluble film material which is selected from the group consisting of polymers or polymer mixtures. The cover can be formed from one or from two or more layers of the water-soluble film material. The water-soluble film material of the first layer and the further layers, if any, can be the same or different. Films are particularly preferred which can be glued and/or sealed to form packaging such as tubes or pillows after they have been filled with an agent. In various embodiments, the foils are in the form of multi-chamber pouches.

It is preferred that the water-soluble coating contains polyvinyl alcohol or a polyvinyl alcohol copolymer. Water-soluble coatings that contain polyvinyl alcohol or a polyvinyl alcohol copolymer have good stability with sufficiently high water solubility, especially cold water solubility.

Suitable water-soluble films for producing the water-soluble casing are preferably based on a polyvinyl alcohol or a polyvinyl alcohol copolymer whose molecular weight is in the range from 10,000 to 1,000,000 gmol ^-1 , preferably from 20,000 to 500,000 gmol ^-1 , particularly preferably from 30,000 to 100,000 gmol ^-1 and in particular from 40,000 to 80,000 gmol ^-1 .

Polyvinyl alcohol is usually produced by hydrolysis of polyvinyl acetate, since the direct synthesis route is not possible. The same applies to polyvinyl alcohol copolymers which are correspondingly produced from polyvinyl acetate copolymers. It is preferred if at least one layer of the water-soluble coating comprises a polyvinyl alcohol whose degree of hydrolysis is 70 to 100 mol %, preferably 80 to 90 mol %, particularly preferably 81 to 89 mol % and in particular 82 to 88 mol %.

A polyvinyl alcohol-containing film material suitable for producing the water-soluble casing can also have a polymer selected from the group consisting of (meth)acrylic acid-containing (co)polymers, polyacrylamides, oxazoline polymers, polystyrene sulfonates, polyurethanes, polyesters, polyethers, polylactic acid or mixtures of the above Polymers can be added. A preferred additional polymer are polylactic acids.

In addition to vinyl alcohol, preferred polyvinyl alcohol copolymers include dicarboxylic acids as further monomers. Suitable dicarboxylic acids are itaconic acid, malonic acid, succinic acid and mixtures thereof, with itaconic acid being preferred.

Polyvinyl alcohol copolymers which are also preferred include, in addition to vinyl alcohol, an ethylenically unsaturated carboxylic acid, its salt or its ester. Such polyvinyl alcohol copolymers particularly preferably contain, in addition to vinyl alcohol, acrylic acid, methacrylic acid, acrylic acid esters, methacrylic acid esters or mixtures thereof.

It can be preferred that the film material contains further additives. The film material can contain, for example, plasticizers such as dipropylene glycol, ethylene glycol, diethylene glycol, propylene glycol, glycerol, sorbitol, mannitol or mixtures thereof. Further additives include, for example, release aids, fillers, crosslinking agents, surfactants, antioxidants, UV absorbers, anti-blocking agents, anti-adhesive agents or mixtures thereof.

Suitable water-soluble films for use in the water-soluble wrappers of the water-soluble packages of the invention are films sold by MonoSol LLC, for example, under the designation M8630, C8400 or M8900. Other suitable films include ^Solublon® PT, ^Solublon® GA, ^Solublon® KC or ^Solublon® KL films from Aicello Chemical Europe GmbH or Kuraray VF-HP films.

The use of the textile treatment agent according to the invention, as described above, for textile care and or conditioning purposes, as defined herein, is another subject of Invention. In particular, the present invention relates to the use of an agent as described herein for conditioning, in particular for softening textiles. The present invention relates to uses in which a textile treatment agent as described herein is used in a manual textile treatment process or, preferably, in the washing machine.

Another subject of the invention is a manual or preferably machine method for conditioning textiles, characterized in that at least one dispersion of at least one cationically modified polyurethane and/or at least one textile treatment agent, as described herein, is used in at least one method step.

In particular, the present invention relates to a method for applying a dispersion of at least one cationically modified polyurethane to textiles, wherein the dispersion in pure form or as a component of a textile treatment agent, as described herein, is given together with the textiles in a household washing machine or an industrial washing machine and a washing program is subjected, so that the dispersion of at least one cationically modified polyurethane is released into the rinsing liquor and can then be reflected on the textiles.

A dispersion of a cationically modified polyurethane or a textile treatment agent containing such a dispersion can in principle also be used advantageously in combination with other textile detergents and/or care agents in corresponding processes. In various embodiments, the present invention relates in particular to those methods in which, in addition to the at least one dispersion or the at least one textile treatment agent, as described herein, a detergent is also used.

All facts, objects and embodiments that are described for the use/means according to the invention are also applicable to the preceding objects of the invention. Therefore, at this point, reference is expressly made to the disclosure at the appropriate point, with the indication that this disclosure also applies to the above uses and methods according to the invention.

examples Example 1: Synthesis of the cationic salt Step 1:

Glycidol (25 g, 0.34 mol), trimethylamine hydrochloride (32.5 g, 0.34 mol) and N,N-diisopropylethylamine (59.22 mL, 0.34 mol) in anhydrous methanol (220 mL) were 12 h stirred at room temperature for a long time. The solvent was removed under reduced pressure then the residue was purified by recrystallization from EtOH/acetone (1:1 v/v) to give 2,3-dihydroxy-N,N,N-trimethylpropane-1-ammonium chloride as a white powder ( 50 g, yield = 88%) was obtained.

Step 2:

2,3-Dihydroxy-N,N,N-trimethylpropane-1-ammonium chloride (10 g, 59 mmol) and 1,2-epoxybutane (20.6 mL, 236 mmol) were prepared in the presence of potassium hydroxide (200 mg, 0 6 mmol) at 120 °C for 24 h in an autoclave. The cationic ammonium diol was obtained as a yellow oil (22 g, yield=92%).

Preparation of the prepolymer:

To a 250 mL round bottom flask equipped with a mechanical stirrer and condenser were added Arkema Realkyd XTR 20112 (75.22 g, Mw 2074 g/mol; adipic acid/butylene glycol polyester polyol), Arkema Realkyd XTR 10110 ( 6.45 g, Mw 1000 g/mol; adipic acid/butylene glycol polyester polyol), cationic ammonium diol (2.44 g, Mw 400 g/mol), and K-HN-8200 (4.08 g, Mw 1941 g/mol; polyether , Mn approximately 2000 g/mol, 80% EO, Hannong Chemicals). The heterogeneous mixture was heated to 75°C (bath temperature) until Realkyd XTR 20112 and XTR 10110 fused with the rest of the components. The mixture was dried under vacuum for 1-2 h. The mixture was allowed to cool to 60°C. DN-980S (0.35 g, 504 g/mol; hexamethylene diisocyanate-based isocyanurate-type polyisocyanate, manufactured by DIC Corporation, isocyanate group content 21 wt%, non-volatile content: 100 wt%), isophorone diisocyanate (5.50 g , Mw 222.29 g/mol) and hexamethylene diisocyanate (6.25, Mw 168 g/mol) were added to the reaction mixture. Then the mixture was heated to 85°C and the catalyst (DBTDL catalyst, 3.8 mg dissolved in 3.87 g acetone) was added. Thereafter, the reaction was left at 85°C for 3 hours. Acetone (123.7g) was added in two portions and stirred to obtain a clear solution. The solution was stored overnight under a nitrogen atmosphere.

Emulsify:

The reaction mixture was heated to 40°C and warm water (111 g) added and the emulsion stirred at 400 rpm for 10 min.

chain extension:

An aqueous solution of ethylenediamine (10% by weight) was added until complete conversion of the isocyanate group (determined by ATR).

Acetone was removed under vacuum pressure to obtain the final waterborne polyurethane dispersion.

Example 2: evaluation of softness

3.5 kg of a cotton-containing laundry load was washed in a front-loading washing machine with a commercially available detergent. The dispersion from example 1 was used in the last rinsing step. After drying, the softness of the laundry load was rated by trained experts in comparison to laundry rinsed only with water (0 = very hard, 6 = very soft). Table 1: Evaluation of softness test condition water 1% dispersion* 2% dispersion* softness 2.2 3.1 3.2 *% by weight, based on 3.5 kg of laundry

Claims (12)

Use of a dispersion of at least one cationically modified polyurethane as a textile softener in textile treatment processes. The use as a fabric softener according to claim 1, characterized in that the dispersion of at least one cationically modified polyurethane is obtainable by a process comprising the steps of a) providing at least one cationically modified polyurethane prepolymer; b) emulsifying the prepolymer from step a) into an aqueous phase; and c) crosslinking the emulsified prepolymer from step b) to obtain a dispersion of a cationically modified polyurethane. The use as a fabric softener according to claim 2, characterized in that step a) the reaction i) at least one organic compound (A) comprising at least one, preferably at least two, isocyanate-reactive functional groups and at least one cationic functional group, or a salt of compound (A),
With ii) at least one polyisocyanate compound (B) and optionally iii) at least one polyol compound (C)
includes. The use as a fabric softener according to claim 3, characterized in that - the compound (A) is an organic compound (A) of formula

(N+(R)3)-X (I),

is, wherein each R is independently H or a straight-chain, cyclic or branched, saturated or unsaturated or aromatic hydrocarbon radical having up to 50 carbon atoms, which may contain one or more groups selected from -O-, -(CO)- and -NH, and X is selected from straight-chain, cyclic or branched, saturated, unsaturated or aromatic, substituted or unsubstituted hydrocarbon radicals of up to 5000 carbon atoms containing at least one -O-(Y) _n -H group, wherein Y in each group is -O- (Y) _n -H each occurrence is independently selected from EO, PO and BO, and n denotes an integer from 1 to 100, and further optionally one or more groups selected from -O-, -(CO)- , -NH- and -NR ¹ ₂ - wherein each R ¹ is independently selected from straight chain, cyclic or branched, saturated, unsaturated or aromatic, substituted or unsubstituted hydrocarbon radicals having up to 20; and or - the compound (B) selected from di- and triisocyanate compounds and isocyanate compounds suitable as crosslinkers. The use as a fabric softener according to claim 3 or 4, characterized in that - the reaction of at least one compound (A), at least one compound (B) and optionally at least one compound (C) takes place in the presence of at least one catalyst; and or - the at least one isocyanate compound (B) comprises or consists of aliphatic di- and triisocyanate compounds; and or - the at least one polyol compound (C) is selected from polyester polyols, polyether polyols, polycarbonate polyols, polysiloxane polyols and polyolefin polyols. The use as a fabric softener according to any one of claims 2 to 5, characterized in that step b) takes place at elevated temperatures in the range from about 27 to about 95°C, preferably from about 30 to about 90°C. The use as a textile softener according to any one of the preceding claims, characterized in that the dispersion of at least one cationically modified polyurethane has a viscosity of approximately 100 to 1000 mPas, preferably approximately 200 to 600 mPas. Textile treatment agent, comprising at least one dispersion of at least one cationically modified polyurethane. The textile treatment agent according to claim 8, characterized in that it is a fabric softener. Textile treatment agent according to Claim 8 or 9, characterized in that the proportion of the at least one dispersion of at least one cationically modified polyurethane is approximately 5 to 25% by weight, preferably approximately 6 to approximately 15% by weight, based in each case on the total weight of the textile treatment agent. amounts to. Textile treatment agent according to one of Claims 8 to 10, characterized in that it contains at least one other component, preferably at least two other components, selected from the group consisting of other softening compounds, fragrances, surfactants, thickeners, emulsifiers, hydrotropes, non-aqueous solvents, electrolytes , pH regulators, perfume carriers, fluorescent agents, dyes, foam inhibitors, antiredeposition agents, enzymes, optical brighteners, Graying inhibitors, shrinkage inhibitors, anti-crease agents, color transfer inhibitors, antimicrobial agents, germicides, fungicides, antioxidants, corrosion inhibitors, antistatic agents, ironing aids, repellent and impregnating agents, swelling and non-slip agents and UV absorbers. Process for conditioning textiles, characterized in that at least one dispersion of at least one cationically modified polyurethane and/or at least one textile treatment agent, as defined in one of Claims 8 to 11, is used in at least one process step.