Aqueous dispersions of precrosslinked organopolysiloxanes

Description

[0001] The invention relates to aqueous dispersions of pre-crosslinked organopolysiloxanes, pre-crosslinked organopolysiloxanes, and cosmetic compositions containing aqueous dispersions of pre-crosslinked organopolysiloxanes. The invention further relates to processes for the production of the pre-crosslinked organopolysiloxanes and their aqueous dispersions. The invention also relates to the use of the cosmetic compositions.

[0002] Organopolysiloxanes are used in cosmetic compositions, for example in hair care products, due to their conditioning properties, such as improving softness and smoothness, reducing combing forces, shine properties, improving color impressions, color protection properties, reducing electrostatic charges, protective properties against thermal stress on the hair or hydrophobing.

[0003] An overview of selected organopolysiloxanes for the care of keratinous materials such as hair can be found in MD Berthiaume, Society of Cosmetic Chemists (ed.), Monograph, Silicones in Hair Care, 1997 and J. Sejpka, Silicone in hair care products, in: SÖFW-Journal, 118th year, no. 17, 1992, pp. 1065-1070.

[0004] Hair is exposed to a variety of external influences in everyday life, leading to damage to the hair surface and thus impairing cosmetic properties such as smoothness, softness, shine, and other parameters compared to undamaged hair. Damage to the hair surface can be caused, for example, by chemical or mechanical treatments, UV radiation, or heat. Along with surface damage to the hair is the destruction and partial removal of the lipid layer covering the cuticle, which is responsible for the highly hydrophobic properties of undamaged, natural hair (RA Lodge, B. Bhusan, Wetting Properties of Human Hair by Means of Dynamic Contact Angle Measurement, Journal of Applied Polymer Science, Vol. 102, 5255-5265, 2006, Wiley).Damaged hair is significantly more hydrophilic compared to undamaged hair, because after the destruction of the superficial lipid layer, a hydrophilic, amino acid-based protein matrix acts as the hair surface.

[0005] Modified siloxanes using oxalamidoester-terminated organopolysiloxanes are known. According to WO 2019 / 114953 A1, these are linear copolymers of oxalamidoester-terminated organopolysiloxanes with amino-terminated polyethers. These exhibit, for example, significantly increased hydrophilicity compared to purely amino-functionalized organopolysiloxanes. However, due to their linear structure, they do not display any elastic effect.

[0006] US Patent 7501184 B2 describes copolymers obtained by reacting linear organopolysiloxanes terminated with oxalamidoester groups with organic diamines. Highly viscous to solid copolymers are obtained, which are used in adhesives, particularly hot-melt adhesives. These highly viscous products are not stably emulsifiable and therefore cannot be used for treating fibrous substrates such as hair. Furthermore, due to their linear structure, they do not exhibit any elastic properties.

[0007] US7223385 B2, US7485289 B2, US7220408 B2, and US7504094 B2 describe cosmetic compositions for the treatment of hair that contain specific aminosilicones and a conditioning agent or thickener. The aminosilicones are terminal dimethylpolysiloxanes with alkoxy / hydroxy groups and either aminoethylaminopropyl alkoxy siloxane units or aminoethylaminopropyl methyl siloxane units, which are uncrosslinked.

[0008] WO 2020 / 239229 A1 describes aqueous dispersions of pre-crosslinked organopolysiloxanes that can be used in cosmetic compositions and preferably form an elastomeric film after removal of the water. It was found that cosmetic formulations for hair applications containing the pre-crosslinked organopolysiloxanes exhibit a special conditioning effect. Despite the property of forming elastomeric films, only a limited effect on the shaping of hair fibers was observed.

[0009] US5039738 A discloses a process for the production of modified aminoorganosiloxanes, in which aminoorganosiloxanes are reacted in aqueous emulsions with dialkyl oxalates, dialkyl pyrocarbonates, or a mixture thereof. It was found that textiles treated with the described emulsions exhibited reduced yellowing.

[0010] WO 2015 / 024079 A1 describes cosmetic compositions containing aminoorganopolysiloxanes, cationic surfactants and dialkyldicarboxylic acid esters of the formula R'-O-CO-R-CO-OR', where R' contains C8-C30 residues.

[0011] According to WO 2004 / 039930 A2, textiles treated with a composition of polycarboxylic acids and aminoorganosiloxanes show improved resistance to creasing and wrinkling.

[0012] A crosslinkable composition of aminoorganopolysiloxane and a crosslinking component, which is an alkoxysilane or siloxane having at least one carboxylic anhydride group, is described in US5399652 A.

[0013] The objective was to provide pre-crosslinked organopolysiloxanes, in particular aqueous dispersions of pre-crosslinked organopolysiloxanes, which preferably form an elastomeric film after removal of the water and which can be used in cosmetic compositions. Furthermore, the objective was to provide cosmetic compositions for the treatment of keratinous fibers, such as hair, preferably for their cleansing and conditioning, which can be used for shaping and conditioning keratinous fibers, such as hair, in particular to facilitate their combability.

[0014] The problem is solved by the invention.

[0015] The invention relates to aqueous dispersions, preferably aqueous emulsions, containing pre-crosslinked organopolysiloxanes, which on average contain at least one structural unit, preferably at least two structural units, preferably at least three structural units, of the general formula SiRO 2 / 2 -Y-SiRO 2 / 2 (I) and units of the formula R 2 SiO 2 / 2 (II), wherein Y a residue of the formula -R 2< -[NR 3< -R 4< ] x -NR 3< -OC-[C(Z 1< )(H)] k1 -[C(Z 2< )(H)] k2 -CO-NR 3< -[R 4< -NR 3< ] a -R 2< -R 2 SiO 1 / 2 -[R 2 SiO 2 / 2 ] b -R 2 SiO 1 / 2 -R 2< -[NR 3< -R 4< ] a - NR 3< -OC-[C(Z 2< )(H)] k2 - [C(Z 1< )(H)] k1 -CO-NR 3< - [R 4< -NR 3< ] x -R 2< - means that R can be the same or different and represents a monovalent SiC-bonded hydrocarbon residue with 1 to 18 carbon atoms, which may contain one or more heteroatoms from the group N, P, S, O and halogen, R 2< may be the same or different and signifies a SiC-bonded, divalent linear or branched hydrocarbon residue with 3 to 18 carbon atoms, preferably an alkylene residue with 3 to 10 carbon atoms, R 3< may be the same or different and signifies a hydrogen atom, an alkyl residue with 1 to 8 carbon atoms or an acyl residue, such as an acetyl residue, preferably a hydrogen atom,R 4< can be the same or different and signifies a divalent hydrocarbon residue with 1 to 6 carbon atoms, preferably an alkylene residue with 1 to 6 carbon atoms, k1 is 0, 1, 2 or 3, preferably 0, k2 is 0, 1, 2 or 3, preferably 0, x is 0, 1, 2, 3 or 4, preferably 0 or 1, a is 0, 1, 2, 3 or 4, preferably 0 or 1, b is 0 or an integer from 1 to 500, preferably 20 to 350, Z 1< signifies -OH, H or -NHR 3< and Z 2< signifies -OH, H or -NHR 3<.

[0016] The invention further relates to pre-crosslinked organopolysiloxanes which contain on average at least one structural unit, preferably at least two structural units, preferably at least three structural units, of the general formula SiRO 2 / 2 -Y-SiRO 2 / 2 (I) and units of the formula R 2 SiO 2 / 2 (II), wherein Y is a remainder of the formula -R 2< -[NR 3< -R 4< x -NR 3< -OC-[C(Z 1< )(H)] k1 -[C(Z 2< )(H)] k2 -CO-NR 3< -[R 4< -NR 3< ] a -R 2< -R 2 SiO 1 / 2 -[R 2 SiO 2 / 2 ] b -R 2 SiO 1 / 2 -R 2< -[NR 3< -R 4< ] a - NR 3< -OC-[C(Z 2< )(H)] k2 -[C(Z 1< )(H)] k1 -CO-NR 3< -[R 4< -NR 3< ] x -R 2< - and R, R 2< , R 3< , R 4< , k1, k2, x, a, b, Z 1< and Z 2< have the meanings given above.

[0017] The invention further relates to a process for producing aqueous dispersions of pre-crosslinked organopolysiloxanes, by Aqueous dispersions, preferably aqueous emulsions, containing aminoorganopolysiloxanes (1) of the formula (R 1< O) d A e R 3-de SiO(SiARO) p (SiR 2 O) q SiR 3-de A e (OR 1< ) d (IV) where A is an amino group of the general formula -R 2< -[NR 3< -R 4< -] x NR 3< 2, R may be the same or different and denotes a monovalent SiC-bonded hydrocarbon group with 1 to 18 carbon atoms, which may contain one or more heteroatoms from the group N, P, S, O, and halogen, R 1< may be the same or different and denotes a hydrogen atom or an alkyl group with 1 to 18 carbon atoms, which may be interrupted by one or more separate oxygen atoms, R 2< may be the same or different and denotes a SiC-bonded, divalent linear or branched Hydrocarbon residue with 3 to 18 carbon atoms, preferably an alkylene residue with 3 to 10 carbon atoms, means,R 3< can be the same or different and represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or an acyl group, such as an acetyl group, preferably a hydrogen atom; R 4< can be the same or different and represents a divalent hydrocarbon group with 1 to 6 carbon atoms, preferably an alkyl group with 1 to 6 carbon atoms; d is 0 or 1; e is 0 or 1; p is an integer of at least 1, preferably at least 2, preferably at least 3, and at most 1000, preferably at most 10; q is 0 or an integer of 1 to 2000, preferably 50 to 1000; x is 0, 1, 2, 3, or 4, preferably 0 or 1; with reactive esters (2) of the formula R 5< -O 2 C-[C(Z 1< )(H)] k1 -[C(Z 2< )(H)] k2 -CO-NR 3< -[R 4< -NR 3< ] a -R 2< -R 2 SiO 1 / 2 -[R 2 SiO 2 / 2 ] b -R 2 SiO 1 / 2 -R 2< -[NR 3< -R 4< ] a - (V) NR 3< -OC-[C(Z 2< )(H)] k2 -[C(Z 1< )(H)] k1 -CO 2 -R 5< where R, R 2< ,R3< and R4< have the meanings given above, R5< may be the same or different and signifies an O-bonded, saturated or unsaturated, linear or branched, monovalent hydrocarbon residue with 1-20 carbon atoms per residue, which may contain one or more heteroatoms from the group N, P, S, O and halogen, k1 is 0, 1, 2 or 3, preferably 0, k2 is 0, 1, 2 or 3, preferably 0, a is 0, 1, 2, 3 or 4, preferably 0 or 1, b is 0 or an integer from 1 to 500, preferably 20 to 350, Z1< means -OH, H or -NHR3< and Z2< means -OH, H or -NHR3< are reacted.

[0018] The invention further relates to a process for the production of the pre-crosslinked organopolysiloxanes, characterized in that Aminoorganopolysiloxanes (1) of the formula (R 1< O) d A e R 3-de SiO(SiARO) p (SiR 2 O) q SiR 3-de A e (OR 1< ) d (IV) with reactive esters (2) of the formula R 5< -O 2 C-[C(Z 1< )(H)] k1 -[C(Z 2< )(H)] k2 -CO-NR 3< - [R 4< -NR 3< ] a -R 2< -R 2 SiO 1 / 2 -[R 2 SiO 2 / 2 ] b -R 2 SiO 1 / 2 -R 2< -[NR 3< -R 4< ] a - (V) NR 3< -OC-[C(Z 2< )(H)] k2 -[C(Z 1< )(H)] k1 -CO 2 -R 5< where A, R, R 1< , R 2< , R 3< , R 4< , R 5< , d, e, p, q, k1, k2, x, a, b, Z 1< and Z 2< have the meaning given above, are reacted, and the pre-crosslinked organopolysiloxanes thus obtained are subsequently emulsified in water if necessary.

[0019] Preferably, in the process according to the invention, the aminoorganopolysiloxanes (1) of formula (IV) are used in which e is equal to 0, i.e., which only contain lateral amino residues A and form bridges in the reaction with the reactive esters (2) according to structural units of formula (I).

[0020] When e is equal to 0, the pre-crosslinked organopolysiloxanes according to the invention contain, in addition to structural units of formula (I) and siloxane units of formula (II), preferably siloxane units of formula R 3-d (OR 1< ) d SiO 1 / 2 (III) where R, R 1< and d have the meaning given above.

[0021] However, aminoorganopolysiloxanes (1) of formula (IV) can also be used, which also contain terminal amino residues A, where e is equal to 1.

[0022] Mixtures of aminoorganopolysiloxanes (1) of formula (IV) with e = 0 and e = 1 can also be used. In the reaction with the reactive esters (2), bridges can additionally be formed between two terminal amino residues (formula (VI)) or between terminal and side amino residues (formula (VII)).

[0023] In addition to the aminoorganopolysiloxanes (1), only terminal amino residues in amino groups (1a) of the formula (R 1< O) f AR 2-f SiO(SiR 2 O) n SiR 2-f A(OR 1< ) f (IVa) can be used. where A, R and R 1< have the meanings given above, f 0 or 1 and n is an integer from 1 to 1000, preferably 50 to 1000.

[0024] The pre-crosslinked organopolysiloxanes according to the invention can therefore contain, as bridges in addition to the structural units of formula (I), further structural units of formulas SiR 2 O 1 / 2 -Y-SiR 2 O 1 / 2 (VI) or SiRO 2 / 2 -Y-SiR 2 O 1 / 2 (VII) or mixtures of (VI) and (VII), wherein R and Y have the meaning given above.

[0025] Preferably, the pre-crosslinked organopolysiloxanes according to the invention contain siloxane units of formula (III), wherein d is 0 or 1, preferably 1.

[0026] The lateral and optionally terminal amino residues A in the aminoorganopolysiloxanes (1) used according to the invention or optionallyThe co-used aminoorganopolysiloxanes (1a) can also react with the reactive esters (2) without forming bridges, so that the pre-crosslinked organopolysiloxanes additionally form structural units of the formulas SiRO 2 / 2 -R 2< -[NR 3< -R 4< ] x -NR 3< -OC-[C(Z 1< )(H)] k1 -[C(Z 2< )(H)] k2 -CO- NR 3< -[R 4< -NR 3< ] a -R 2< -R 2 SiO 1 / 2 -[R 2 SiO 2 / 2 ] b -R 2 SiO 1 / 2 -R 2< -[NR 3< -R 4< ] a (VIII a ) -NR 3< -OC-[C(Z 2< )(H)] k2 -[C(Z 1< )(H)] k1 -CO 2 -R 5< and / or SiR 2 O 1 / 2 -R 2< -[NR 3< -R 4< x -NR 3< -OC-[C(Z 1< )(H)] k1 -[C(Z 2< )(H)] k2 -CO- NR 3< -[R 4< -NR 3< ] a -R 2< -R 2 SiO 1 / 2 -[R 2 SiO 2 / 2 ] b -R 2 SiO 1 / 2 -R 2< -[NR 3< -R 4< ] a (VIIIb) -NR 3< -OC-[C(Z 2< )(H)] k2 -[C(Z 1< )(H)] k1 -CO 2 -R 5< may contain, where R, R 2< , R 3< , R 4< , R 5< , k1, k2, x, a, b, Z 1< and Z 2< have the meanings given above.

[0027] Within the scope of this invention, formula (IV) shall be understood to mean that p units -(SiARO)- and q units -(SiR 2 O)- can be distributed in any way, for example as a block or statistically, in the amine organopolysiloxane molecule.

[0028] The aminoorganopolysiloxanes (1) used according to the invention and optionally the aminoorganopolysiloxanes (1a) used together may, which is not expressed by formulas (IV) or (IVa), also contain siloxane units selected from the group of formulas RSiO 3 / 2 , (OR 1< ) SiO 3 / 2 and SiO 4 / 2 (IXa-c), wherein R and R 1< have the meaning given above, so that the pre-crosslinked organopolysiloxanes according to the invention may also contain siloxane units of formulas (IXa-c).

[0029] Preferably, R is a monovalent, saturated or unsaturated hydrocarbon residue with 1 to 18 carbon atoms.

[0030] Examples of hydrocarbon residues R are alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and tert-pentyl; hexyl groups, such as n-hexyl; heptyl groups, such as n-heptyl; octyl groups, such as n-octyl and iso-octyl groups, such as 2,2,4-trimethylpentyl; nonyl groups, such as n-nonyl; decyl groups, such as n-decyl; dodecyl groups, such as n-dodecyl; and octadecyl groups, such as n-octadecyl. Cycloalkyl groups, such as cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl groups; alkenyl groups, such as vinyl, 5-hexenyl, cyclohexenyl, 1-propenyl, allyl, 3-butenyl and 4-pentenyl groups; aryl groups, such as phenyl, naphthyl, anthryl and phenanthryl groups; alkaryl groups, such as o-, m-, p-tolyl groups; xylyl groups and ethylphenyl groups; and aralkyl groups, such as benzyl, α- and β-phenylethyl groups.

[0031] Preferred R groups are methyl, ethyl, octyl and phenyl groups, methyl and ethyl groups are particularly preferred.

[0032] Examples of substituted R groups are haloalkyl groups, such as the 3,3,3-trifluoro-n-propyl group, the 2,2,2,2',2',2'-hexafluoroisopropyl group, the heptafluoroisopropyl group and haloaryl groups, such as the o-, m- and p-chlorophenyl group.

[0033] Other examples of substituted residues R are polyalkylenoxy groups, such as polyethyleneoxy, polypropylenoxy or polyethyleneoxy / polypropylenoxy groups.

[0034] Examples of residue R 1< are the alkyl residues listed above under R, as well as the methoxyethyl, ethoxyethyl and hexoxyethyl residues, wherein residue R 1< is preferably hydrogen, methyl or ethyl.

[0035] Preferably, R5 is a C1-20 hydrocarbon residue, which may be interrupted by one or more oxygen atoms. Examples of residues R5 also apply to residues R5.

[0036] Preferably, R 5< is a C 1-4 alkyl group, such as a methyl or ethyl group.

[0037] Examples of radicals A are: -(CH 2 ) 3 NH 2 -(CH 2 ) 3 -NH-(CH 2 ) 2 -NH 2 -CH 2 CH(CH 3 )CH 2 -NH-(CH 2 ) 2 -NH 2 -(CH 2 ) 3 -NH(Cyclohexyl) -(CH 2 ) 3 -NHCH 3 -(CH 2 ) 3 -N(CH 3 ) 2 -(CH 2 ) 3 -NHCH 2 CH 3 -(CH 2 ) 3 -N(CH 2 CH 3 ) 2 -(CH 2 ) 4 -NH 2 -CH 2 CH(CH 3 )CH 2 -NH 2 -(CH 2 ) 3 -NH-(CH 2 ) 2 -NHCH 3 -(CH 2 ) 3 -NH-(CH 2 ) 2 -N(CH 3 ) 2 -(CH 2 ) 3 -NH-(CH 2 ) 2 -NHCH 2 CH 3 -(CH 2 ) 3 -NH-(CH 2 ) 2 -N(CH 2 CH 3 ) 2 -(CH 2 ) 3 [-NH-CH 2 CH 2 ] 2 -NH 2 and their partially or fully acetylated forms, such as -(CH 2 ) 3 -NH(Acetyl) -(CH 2 ) 3 -NH-(CH 2 ) 2 -NH(Acetyl) and -(CH 2 ) 3 -N(Acetyl)-(CH 2 ) 2 -NH(Acetyl).

[0038] Preferred examples of residues A are: -(CH 2 ) 3 NH 2 -(CH 2 ) 3 -NH-(CH 2 ) 2 -NH 2 -CH 2 CH(CH 3 )CH 2 -NH-(CH 2 ) 2 -NH 2 -(CH 2 ) 3 -NHCH 3

[0039] Preferably, A is an amino group of the formula -R 2< -[NH-CH 2 CH 2 -] x NH 2 where x is 0 or 1 and R 2< is a remainder of the formula -(CH 2 ) 3 - or -CH 2 -CH(CH 3 )-CH 2 -.

[0040] Particularly preferred examples for residue A are -(CH 2 ) 3 NH 2 -(CH 2 ) 3 -NH-(CH 2 ) 2 -NH 2 and -CH 2 CH(CH 3 )CH 2 -NH-(CH 2 ) 2 -NH 2 .

[0041] Other examples of aminoorganopolysiloxanes (1) are commercially available functionalized siloxanes, such as amine oils, e.g. amine oils with 3-(2-aminoethyl)aminopropyl functionalities, as well as glycol oils, phenyl or phenylmethyl oils containing amino groups.

[0042] In the production of the dispersions according to the invention, one type of aminoorganopolysiloxane (1) or different types of aminoorganopolysiloxane (1) can be used.

[0043] The aminoorganopolysiloxanes (1) used in the production of the dispersions according to the invention preferably have viscosities of 1 mPa.s to 50,000,000 mPa.s at 25°C, preferably 50 mPa.s to 10,000,000 mPa.s at 25°C and particularly preferably 100 mPa.s to 500,000 mPa.s at 25°C.

[0044] The aminoorganopolysiloxanes (1) used in the manufacture of the dispersions according to the invention can be produced, for example, as described in US 7,129,369 B2.

[0045] The dispersions according to the invention preferably contain pre-crosslinked organopolysiloxanes according to the invention, Emulsifiers (3) and water (4).

[0046] In the production of the dispersions of pre-crosslinked organopolysiloxanes according to the invention, further substances that do not directly participate in the reaction may optionally be used.

[0047] Upon drying, the dispersions according to the invention form a silicone network, preferably an elastic silicone network, without the addition of a catalyst or any change in pH. Preferably, after the removal of water, the dispersions according to the invention form elastomeric films.

[0048] In the process according to the invention, the reaction of aminoorganopolysiloxanes (1) and optionally (1a) with reactive esters (2), preferably no metal-containing catalysts are used.

[0049] The dispersions according to the invention therefore preferably do not contain catalysts.

[0050] In the preparation of the pre-crosslinked organopolysiloxanes according to the invention, aminoorganopolysiloxanes (1) and reactive esters (2) are used, and these components preferably react with each other at room temperature. No additional metal-containing catalysts are required to support this reaction; that is, preferably no transition metals of group VIII of the periodic table and their compounds, and no metals of groups III, IV, and V of the periodic table and their compounds are used, wherein the elements C, Si, N, and P are not considered metals in this definition.

[0051] Furthermore, the reaction preferably proceeds in the neutral range, i.e., in the pH range of approximately 4 to 8, which results from the components themselves. Due to the high reactivity, a controlled chemical reaction is unnecessary, and preferably heating is also unnecessary.

[0052] In the production of the dispersions according to the invention, one type of ester (2) can be used as a crosslinker or different types of esters (2) can be used as crosslinkers.

[0053] Preferably, oxalamidoester-terminated organopolysiloxanes of the formula R 5< -O 2 C-CO-NH-R 2< -R 2 SiO 1 / 2 -[R 2 SiO 2 / 2 ] b -R 2 SiO 1 / 2 -R 2< -NH-OC-CO 2 -R 5< are used as esters (2), wherein R has the meaning given above, R 2< is a residue of the formula -(CH 2 ) 3 - or -CH 2 -CH(CH 3 )-CH 2 -, R 5< has the meaning given above, preferably a C 1-4 alkyl residue, in particular a methyl or ethyl residue, and b is equal to 0 or an integer from 1 to 500, preferably 20 to 350.

[0054] Therefore, Y is preferably a residue of the formula -R 2< -[NH-CH 2 CH 2 ] x -NH-OC-CO-NH-R 2< -R 2 SiO 1 / 2 -[R 2 SiO 2 / 2 ] b -R 2 SiO 1 / 2 - R 2< -NH-OC-CO-NH-[CH 2 CH 2 -NH] x -R 2< - where x is 0 or 1, b and R have the meaning given above and R 2< is a remainder of the formula -(CH 2 ) 3 - or -CH 2 -CH(CH 3 )-CH 2 -.

[0055] Depending on the use of crosslinker (2) or linear, branched or resinous aminoorganopolysiloxane (1), the pre-crosslinked organopolysiloxanes can have branched or even highly branched or strongly crosslinked structures with linear components.

[0056] In the process according to the invention, aminoorganopolysiloxanes and esters are selected in type and quantity such that the organopolysiloxanes are pre-crosslinked in the dispersions obtained.

[0057] Preferably, the aminoorganopolysiloxanes (1) used are those which contain, on average, at least one primary amino function in the side-ended amino residues A, so that pre-crosslinked organopolysiloxanes according to the invention are obtained. Alternatively, aminoorganopolysiloxanes (1a) which contain only terminal amino residues A with primary amino functions can also be used.

[0058] When aminoorganopolysiloxanes (1a) are used, they are preferably used in amounts of 10 to 300 parts by weight, per 100 parts by weight of aminoorganopolysiloxanes (1).

[0059] Furthermore, pre-crosslinked organopolysiloxanes according to the invention are also obtained when using mixtures of aminoorganopolysiloxanes (1) and non-functional organopolysiloxanes (1b). Non-functional organopolysiloxanes (1b) are organopolysiloxanes without amino groups A, preferably linear organopolysiloxanes of the general formula R7<u R6<3-u SiO[R6<2 SiO]v SiR6<3-u R7<u (X) where R6< has the meaning of R and R 7< has the meaning of R 6< or is an HO group, u 0 or 1 and v 0 or is an integer from 1 to 2000.

[0060] Preferably, R 6< is a C 1-18 hydrocarbon residue, preferably a C 1-18 alkyl residue.

[0061] Examples of non-functional organopolysiloxanes (1b) are dialkylpolysiloxanes, preferably dimethylpolysiloxanes.

[0062] When non-functional organopolysiloxanes (1b) are used, they are preferably used in amounts of 100 to 800 parts by weight per 100 parts by weight of aminoorganopolysiloxanes (1).

[0063] The degree of cross-linking depends on the ratio of the equivalents -OR 5< of the reactive ester (2) to the amino residue A in the aminoorganopolysiloxane (1).

[0064] To produce the dispersions according to the invention from aminoorganopolysiloxane (1) and reactive ester (2), the ester (2) is preferably used in amounts of 0.1 to 10 equivalents of -OR 5< , preferably 0.2 to 5 equivalents of -OR 5< , particularly preferably 0.3 to 3 equivalents of -OR 5< , per equivalent of amino residue A in the aminoorganopolysiloxane (1).

[0065] The dispersions of pre-crosslinked organopolysiloxanes according to the invention are produced by intensive mixing of aminoorganopolysiloxanes (1) with esters (2), emulsifiers (3) and water (4). The production can be carried out batchwise or continuously.

[0066] The method of mixing the components used to produce the dispersions according to the invention is not very critical and can be carried out in different sequences.

[0067] For example, components (1) and (2) can be premixed together, then the emulsifier(s) added, and subsequently water (4) incorporated. It is also possible to dose components (1) to (4) into the emulsifying apparatus sequentially. In specific cases, for example, due to the viscosity or reactivity of the aminoorganopolysiloxanes (1) and, if applicable, (1a) and, if applicable, non-functional organopolysiloxanes (1b) used, it may be advantageous to mix ester (2) with one aminoorganopolysiloxane and then incorporate another aminoorganopolysiloxane or non-functional organopolysiloxane, or vice versa, depending on which results in more favorable rheological properties for the processing of the components.

[0068] Furthermore, it is also possible to add the ester (2) as a crosslinking agent to the finished emulsion of aminoorganopolysiloxanes (1) to achieve the desired reaction and crosslinking of the aminoorganopolysiloxane in the emulsion. To obtain VOC-free products, i.e., products without volatile organic compounds, the byproduct alcohol R5OH (where R5 has the meaning given above) can be partially or completely removed by suitable known methods such as distillation, membrane processes, or other separation methods.

[0069] In the production of the dispersions according to the invention, water (4) is used in amounts of preferably 1 to 99 wt.%, particularly preferably 25 to 95 wt.%, in each case based on the total weight of all ingredients of the dispersion.

[0070] The aqueous dispersion of pre-crosslinked organopolysiloxanes according to the invention is used as an oil-in-water system.

[0071] All previously known anionic, nonionic, cationic or amphoteric emulsifiers, both individually and as mixtures of different emulsifiers, can be used as emulsifiers (3) for the preparation of aqueous dispersions of pre-crosslinked organopolysiloxanes, provided that aqueous dispersions, in particular aqueous emulsions of organopolysiloxanes, have been successfully prepared with them.

[0072] Examples of anionic emulsifiers are: 1. Alkyl sulfates, especially those with a chain length of 8 to 18 carbon atoms, alkyl and alkaryl ether sulfates with 8 to 18 carbon atoms in the hydrophobic residue and 1 to 40 ethylene oxide (EO) or propylene oxide (PO) units. 2. Sulfonates, especially alkyl sulfonates with 8 to 18 carbon atoms, alkylarylsulfonates with 8 to 18 carbon atoms, taurides, esters and semiesters of sulfosuccinic acid with monohydric alcohols or alkylphenols with 4 to 15 carbon atoms; optionally, these alcohols or alkylphenols may also be ethoxylated with 1 to 40 EO units. 3. Alkali and ammonium salts of carboxylic acids with 8 to 20 carbon atoms in the alkyl, aryl, alkaryl, or aralkyl residue. 4. Phosphoric acid partial esters and their alkali and ammonium salts, especially alkyl and alkaryl phosphates with 8 to 20 C atoms in the organic residue, alkyl ether or alkaryl ether phosphates with 8 to 20 C atoms in the alkyl or alkaryl residue and 1 to 40 EO units.

[0073] Examples of non-ionic emulsifiers are: 5. Polyvinyl alcohol containing 5 to 50%, preferably 8 to 20%, vinyl acetate units, with a degree of polymerization of 500 to 3000. 6. Alkyl polyglycol ethers, preferably those with 3 to 40 EO units and alkyl groups of 8 to 20 carbon atoms. 7. Alkyl aryl polyglycol ethers, preferably those with 5 to 40 EO units and 8 to 20 carbon atoms in the alkyl and aryl groups. 8. Ethylene oxide / propylene oxide (EO / PO) block copolymers, preferably those with 8 to 40 EO or PO units. 9. Addition products of alkylamines with alkyl groups of 8 to 22 carbon atoms with ethylene oxide or propylene oxide. 10. Fatty acids with 6 to 24 carbon atoms. 11. Alkyl polyglycosides of the general formula R''-OZ O , wherein R'' represents a linear or branched, saturated or unsaturated alkyl group with an average of 8–24 carbon atoms and ZO represents an oligoglycoside group with an average of 0 = 1–10 hexose or pentose units or mixtures thereof. 12.Natural products and their derivatives, such as lecithin, lanolin, saponins, cellulose; cellulose alkyl ethers and carboxyalkyl celluloses, whose alkyl groups each possess up to 4 carbon atoms. 13. Linear organo(poly)siloxanes containing polar groups, in particular those containing the elements O, N, C, S, P, Si, especially those with alkoxy groups with up to 24 carbon atoms and / or up to 40 EO and / or PO groups.

[0074] Examples of cationic emulsifiers are: 14. Salts of primary, secondary, and tertiary fatty amines with 8 to 24 carbon atoms with acetic acid, sulfuric acid, hydrochloric acid, and phosphoric acids. 15. Quaternary alkyl and alkylbenzeneammonium salts, in particular those whose alkyl groups have 6 to 24 carbon atoms, especially the halides, sulfates, phosphates, and acetates. 16. Alkylpyridinium, alkylimidazolinium, and alkyloxazolinium salts, in particular those whose alkyl chain has up to 18 carbon atoms, specifically the halides, sulfates, phosphates, and acetates.

[0075] Particularly suitable as amphoteric emulsifiers are: 17. Long-chain substituted amino acids, such as N-alkyl-di-(aminoethyl)glycine or N-alkyl-2-aminopropionic acid salts. 18. Betaines, such as N-(3-acylamidopropyl)-N,N-dimethylammonium salts with a C8-C18 acyl group and alkylimidazolium betaines or quaternized alkyl or substituted alkyl derivatives of N,N-dimethylglycine.

[0076] Preferably used as emulsifiers for the production of aqueous dispersions of pre-crosslinked organopolysiloxanes are non-ionic emulsifiers, in particular the alkyl polyglycol ethers listed above under 6.

[0077] Component (3) may consist of one of the aforementioned emulsifiers or of a mixture of two or more aforementioned emulsifiers; it may be used in pure form or as solutions of one or more emulsifiers in water or organic solvents.

[0078] In the production of the dispersions according to the invention, the emulsifiers (3) are used in amounts of preferably 0.1 to 60 wt.%, particularly preferably 0.5 to 30 wt.%, in each case based on the total weight of aminoorganopolysiloxanes (1) and esters (2).

[0079] If the aminoorganopolysiloxane (1) or the ester (2) or the resulting pre-crosslinked organopolysiloxane itself acts as an emulsifier, the addition of a separate emulsifier (3) can be omitted.

[0080] The emulsification process for producing the dispersion is preferably carried out at temperatures below 120°C, more preferably at temperatures between 5°C and 100°C, and particularly preferably at temperatures between 10°C and 80°C. The temperature increase is preferably achieved by the input of mechanical shear energy required for the emulsification process. The temperature increase is not required to accelerate a chemical process. Furthermore, the dispersions are preferably produced at atmospheric pressure, but this can also be carried out at higher or lower pressures.

[0081] The reaction of aminoorganopolysiloxanes (1) with esters (2) in the preparation of the dispersions preferably takes place in a few minutes to several days.

[0082] The alcohols produced as condensation byproducts during the manufacture of the dispersions can remain in the product or be removed, for example by distillation under vacuum, membrane processes, or extraction.

[0083] The mean particle size measured in the dispersions according to the invention using laser diffraction (with the Mastersizer 3000 Particle Size Analyzer from Malvern Panalytical) is preferably in the range of 0.001 to 50 µm, preferably in the range of 0.005 to 20 µm, and particularly preferably in the range of 0.01 to 10 µm.

[0084] The pH values ​​can vary from 1 to 14, preferably 3 to 9, particularly preferably 4 to 8.

[0085] The invention relates to cosmetic compositions containing aqueous dispersions, preferably aqueous emulsions, of pre-crosslinked organopolysiloxanes according to the invention.

[0086] The cosmetic composition according to the invention contains aqueous dispersions of pre-crosslinked organopolysiloxanes preferably in amounts of 0.2 to 65 wt.%, preferably of 0.5 to 50 wt.%, in each case based on the total weight of the cosmetic composition.

[0087] The cosmetic compositions according to the invention preferably contain water as a cosmetically acceptable medium.

[0088] The cosmetic composition according to the invention preferably contains a conditioning agent. Conditioning agents are defined, analogously to K. Krummel, Stephane Chiron, J. Jachowicz, Chapter 14, in: "The Chemistry and Manufacture of Cosmetics", Volume II, Formulating, Third Edition by Mitchell L. Schlossmann, 2000, pp. 359-396, as cosmetic ingredients that modify the hair surface and influence the hair's condition.Cosmetic compositions containing conditioning agents are used to modify or improve hair softness, detangling, reducing wet and dry combing effort, conditioning hair, preventing static electricity, facilitating gliding through the hair and along the hair surface, improving shine, maintaining hair color, reducing breakage, preserving hair shape, and other cosmetic properties associated with natural and healthy hair.

[0089] The cosmetic composition according to the invention improves one or more of the above-mentioned effects, in particular combability and the deposition of the silicone on the hair.

[0090] Examples of conditioning agents and their INCI names are described in the "International Cosmetic Ingredient Dictionary & Handbook" of the Personal Care Product Council (ed.).

[0091] The World Wide Web-based "wINCI Web Based International Cosmetic Ingredient Dictionary & Handbook" (http: / / online.personalcarecouncil.org / jsp / Home.jsp) or the International Cosmetic Ingredient Dictionary & Handbook, 13th Edition, The Personal Care Products Council (formerly: The Cosmetic, Toiletry, and Fragrance Association (CTFA)), 2010, can be used as a reference.

[0092] Conditioning agents are preferably selected from the group of cationic polymers, cationic surfactants, non-polymeric quaternary ammonium compounds, organopolysiloxanes and organopolysiloxane copolymers containing structural units of formula (I) different from pre-crosslinked organopolysiloxanes, fatty acid esters and fatty acid alcohols, natural or synthetic oils and waxes and panthenol, lipids, proteins and hydrolyzed proteins, and mixtures thereof.

[0093] Preferred examples of conditioning agents are cationic polymers. These are polymers that bear lateral or terminal cationic groups, or lateral or terminal groups that can be converted into cationic groups by ionization.

[0094] Preferably, cationic polymers are used that have a quaternary ammonium group.

[0095] Examples of preferred cationic polymers are published in the International Cosmetic Ingredient Dictionary & Handbook under the name Polyquaternium, with each polymer being identified by an individual numerical code, e.g. Polyquaternium-1.

[0096] Other examples of cationic polymers are derivatives of modified polysaccharides containing quaternary ammonium groups, e.g., polymers with the INCI name Cassia Hydroxypropyltrimonium Chloride, derivatives of modified cellulose and / or starch, e.g.a quaternary ammonium derivative of Cyamopsis Tetragonoloba (Guar) gum modified with propylene glycol ether, with the INCI name Guar Hydroxypropyltrimonium Chloride, or polymeric quaternary ammonium salts of the reaction product of hydroxyethylcellulose with a trimethylammonium-substituted epoxide, such as cellulose, 2-hydroxyethyl 2-(2-hydroxy-3-(trimethylammonium)propoxy)ethyl 2-hydroxy-3-(trimethylammonio)propyl ether chloride, such as cellulose, 2-hydroxyethyl 2-hydroxy-3-(trimethylammonium)propyl ether chloride, such as cellulose, 2-hydroxyethyl 2-hydroxy-3-(trimethylammonium)propyl ether chloride, such as cellulose, 2-[2-hydroxy-3-(trimethylammonium)propoxy]ethyl ether chloride, such as cellulose, 2-[2-Hydroxy-3-Trimethylammonium)propoxy] Ethyl ether chloride with the INCI name Polyquaternium-10.

[0097] Other examples of cationic polymers are acrylic acid polymer derivatives containing quaternary ammonium groups, acrylic acid copolymer derivatives, methacrylic acid derivatives and methacrylic acid copolymer derivatives, e.g. polymers with the INCI name Polyquaternium-37.

[0098] Other examples of cationic polymers are copolymers of dimethyldiallylammonium chloride and acrylic acid containing quaternary ammonium groups, e.g. polymers with the INCI name Polyquaternium-22.

[0099] Other examples of cationic polymers are copolymers containing quaternary ammonium groups, made from derivatives of vinylpyrrolidone, viylimidazole and vinylimidazoline and methacrylic acid, e.g. polymers with the INCI name Polyquaternium-86.

[0100] Other examples of cationic polymers are copolymers of acrylamide and dimethyl diallyl ammonium chloride containing quaternary ammonium groups, e.g. polymers with the INCI name Polyquaternium-7.

[0101] Other examples of cationic polymers are copolymers containing quaternary ammonium groups from the reaction product of diethyl sulfate with vinylpyrrolidone and dimethylaminoethyl methacrylate, e.g. polymers with the INCI name Polyquaternium-11.

[0102] When cationic polymers are used, the cosmetic composition according to the invention preferably contains cationic polymers in amounts of 0.01 to 5 wt.%, preferably 0.05 to 4 wt.%, and in particular preferably 0.10 to 3 wt.%, in each case based on the total weight of the cosmetic composition.

[0103] Other preferred examples of conditioning agents are cationic surfactants. Examples of preferably used cationic surfactants correspond to the materials listed in points 14 to 16 under Examples of cationic emulsifiers. Examples include cetyltrimethylammonium salts or behenyltrimethylammonium salts. Anionic counterions can include, for example, chloride, bromide, or methosulfate. INCI names of preferably used cationic surfactants include, for example, cetrimonium chloride, cetrimonium methosulfate, behentrimonium chloride, behentrimonium methosulfate, and steartrimonium bromide.

[0104] When cationic surfactants are used, the cosmetic composition according to the invention preferably contains cationic surfactants in amounts of 0.1 to 7 wt.%, preferably 0.15 to 6 wt.%, and in particular preferably 0.2 to 5 wt.%, in each case based on the total weight of the cosmetic composition.

[0105] Other examples of conditioning agents are non-polymeric quaternary ammonium compounds. These are understood to be non-polymeric ammonium compounds that exist in cationic form or can be converted into a cationic group by ionization.

[0106] Examples of preferably used non-polymeric quaternary ammonium compounds are dimethyl dioctadecyl ammonium chlorides with the INCI name distearyldimonium chloride, N-[3-(dimethylamino)propyl]octadecanamide with the INCI name stearamidopropyl dimethylamine, or compounds with the INCI name dicocoylethyl hydroxyethylmonium methosulfate or quaternium-87.

[0107] Other preferred examples of conditioning agents are organopolysiloxanes and organopolysiloxane copolymers, which differ from the pre-crosslinked organopolysiloxanes with structural units of formula (I) present in aqueous dispersions. The organopolysiloxanes may be in the form of an oil, wax, gum, or resin, or in the form of an emulsion.

[0108] Examples of such organopolysiloxanes that differ from the pre-crosslinked organopolysiloxanes with structural units of formula (I) are: Cyclic organopolysiloxanes of the formula [R* 2 SiO] x' where x' is an integer from 4 to 8, linear organopolysiloxanes of the general formula R* 3 SiO[R* 2 SiO] y SiR* 3 or HOSiR* 2 O[R* 2 SiO] y SiR* 2 OH , where y is 0 or an integer from 1 to 2000, and resinous organopolysiloxanes of the general formula R* t SiO (4-t) / 2 where R* has the meaning of R, R 1< or A, preferably R and R 1< , as indicated above, and t is 0, 1, 2 or 3, such that the organopolysiloxane resin is composed of M, D, T and / or Q units, wherein the combination predominantly or exclusively of D and T units is as preferred as the combination predominantly or exclusively of M and Q-units, wherein in the case of resins composed predominantly or exclusively of D and T-units, T-units are preferably in a molar ratio of T / [M+D+T+Q] of 0.45 to 1, particularly preferably of 0.55 to 1,0 and the number of M and Q units is preferably zero in both cases, and in the case of organopolysiloxane resins composed predominantly or exclusively of M and Q units, Q units are preferably present in a molar ratio of Q / [M+D+T+Q] of 0.25 to 0.9, particularly preferably of 0.35 to 0.7, and the number of D and T units is preferably zero in both cases.

[0109] Examples of organopolysiloxanes, present in the form of an oil, are polydimethylsiloxanes with a viscosity of 0.65 to 2,000,000 mPas (25°C) and the INCI names disiloxane and dimethicone.

[0110] Further examples of organopolysiloxanes, present in the form of an oil or wax, are functionalized organopolysiloxanes, for example, polyalkylsiloxanes in which at least one alkyl group differs from methyl, for example, organopolysiloxanes with the INCI name Stearyl Dimethicone, Cetyl Dimethicone, or C26-28 Alkyl Dimethicone; or, for example, polyarylsiloxanes and polyarylalkylsiloxanes, for example, organopolysiloxanes with the INCI name Phenyl Trimethicone, Trimethylsiloxyphenyl Dimethicone, or Dimethylphenyl Dimethicone; or, for example, organopolysiloxanes with an organofunctional group such as an aminopropyl, aminopropyl aminoethyl, or aminopropyl aminoisobutyl group, for example, organopolysiloxanes with the INCI name Amodimethicone; or, for example, organopolysiloxanes with a polyethylene glycol or polyalkylene glycol group, for example, organopolysiloxanes with the INCI name... PEG-12 Dimethicone, PEG / PPG-25,25-Dimethicone or Cetyl PEG / PPG-15 / 15 Butyl Ether Dimethicone.

[0111] Other examples of organopolysiloxanes are silicone resins with the INCI names trimethylsiloxysilicate or polymethylsilsesquioxane.

[0112] When such organopolysiloxanes or organopolysiloxane copolymers are used, the cosmetic composition according to the invention contains organopolysiloxanes and organopolysiloxane copolymers that differ from the pre-crosslinked organopolysiloxanes with structural units of formula (I) present in the aqueous dispersions, preferably in amounts of 0.1 to 40 wt.%, more preferably of 0.2 to 30 wt.%, and particularly preferably of 0.3 to 20 wt.%, in each case based on the total weight of the cosmetic composition.

[0113] Other preferred examples of conditioning agents are fatty acid esters and fatty acid alcohols.

[0114] Examples of fatty acid alcohols are alcohols with C8-C28 carbon chains such as the fatty alcohols 1-Octadecanol with the INCI name Stearyl Alcohol, 1-Hexadecanol with the INCI name Cetyl Alcohol, or fatty alcohols with the INCI names Cetearyl Alcohol, Myristyl Alcohol, Caprylic Alcohol, Lauryl Alcohol, Decyl Alcohol and Oleyl Alcohol.

[0115] In addition to conditioning properties, fatty acid alcohols also have a structuring and thickening effect in cosmetic compositions.

[0116] Other examples of fatty acid esters are esters of fatty acids with the INCI names Palmitic Acid, Oleic Acid, Linolic Acid, Linoleic Acid, Caprylic Acid, Myristic Acid and Stearic Acid, for example fatty acid esters with the INCI names Isopropyl Palmitate, Ethylhexyl Palmitate, Isopropyl Myristate and Isopropyl Stearate.

[0117] When fatty acid esters and fatty acid alcohols are used, the cosmetic composition according to the invention preferably contains fatty acid esters and fatty acid alcohols in amounts of 0.1 to 15 % by weight, preferably from 0.3 to 12 % by weight, especially preferably 0.5 to 10 % by weight, each based on the total weight of the cosmetic composition.

[0118] Other preferred examples of conditioning agents are natural or synthetic oils and waxes.

[0119] Examples of preferred oils and waxes are hydrocarbons with linear or branched, saturated or unsaturated C4-C60 carbon chains, such as oils and waxes with the INCI names Isododecane, hydrated Polyisobutylene, hydrated Polydecene, Paraffin and Isoparaffin.

[0120] Other examples of preferred oils and waxes include carnauba wax, beeswax, wool wax, microcrystalline wax, jojoba oil, rice oil, calendula oil, sunflower oil, soybean oil, coconut oil, olive oil and almond oil.

[0121] When natural or synthetic oils and waxes are used, the cosmetic composition according to the invention preferably contains oils and waxes in amounts of 0.1 to 10 wt.%, preferably 0.2 to 7 wt.%, and in particular preferably 0.3 to 5 wt.%, in each case based on the total weight of the cosmetic composition.

[0122] Other preferred examples of conditioning agents are panthenol, lipids such as ceramides, proteins and hydrolyzed proteins such as hydrolyzed collagen, hydrolyzed wheat proteins and hydrolyzed silk.

[0123] Optionally, the cosmetic composition contains other cosmetically common additives, such as surfactants, thickeners, gelling agents, film formers, moisturizing agents, UV filters, pearlescent pigments, vitamins, antioxidants, caffeine, anti-dandruff agents or preservatives.

[0124] Examples of other additives commonly used in cosmetics and their INCI names are described in the "International Cosmetic Ingredient Dictionary & Handbook" of the Personal Care Product Council.

[0125] Optionally, the cosmetic composition contains other cosmetically common additives such as surfactants.

[0126] Examples of surfactants commonly used in cosmetics are also described in K. Schrader, A. Domsch, Cosmetology - Theory and Practice, Volume II, pages II-8 to II-22, Verlag für chemische Industrie, 2005, as well as in points 1 to 18 under Examples of emulsifiers.

[0127] Examples of preferably used anionic surfactants correspond to the materials listed in points 1 to 3 under Examples of anionic emulsifiers.

[0128] INCI names of preferably used anionic surfactants are, for example, Sodium Lauryl Sulfate, Ammonium Laureth Sulfate, Sodium Laureth Sulfate, Disodium 2-Sulfolaurate, Disodium Lauryl Sulfosuccinate or Disodium Laureth-Sulfosuccinate.

[0129] When anionic surfactants are used, the cosmetic composition according to the invention preferably contains anionic surfactants in amounts of 1 to 30 wt.%, preferably 5 to 25 wt.%, and in particular preferably 7 to 20 wt.%, in each case based on the total weight of the cosmetic composition.

[0130] Examples of preferably used non-ionic surfactants correspond to the materials listed in points 5 to 13 under Examples of non-ionic emulsifiers.

[0131] INCI names of preferably used non-ionic surfactants are, for example, Coco Glucoside, Lauryl glucoside, Decyl Glucoside, PEG-40 Hydrogenated Castor Oil, Polysorbate 80 or PEG-7 Glyceryl Cocoate.

[0132] When non-ionic surfactants are used, the cosmetic composition according to the invention preferably contains non-ionic surfactants in amounts of 1 to 15 wt.%, preferably 2 to 12 wt.%, and in particular preferably 3 to 10 wt.%, in each case based on the total weight of the cosmetic composition.

[0133] Examples of preferably used amphoteric surfactants correspond to the materials listed in points 17 and 18 under Examples of nonionic emulsifiers. Further preferred examples are compounds from the classes of alkylamidobetaines, alkylamphoacetates, and alkylamphopropionates. INCI names of preferably used nonionic surfactants include, for example, cocamidopropyl betaine, cetyl betaine, cocamide MEA, cocamide DEA, cocamide MIPA, sodium cocoamphoacetate, and sodium cocoamphopropionate.

[0134] When amphoteric surfactants are used, the cosmetic composition according to the invention preferably contains amphoteric surfactants in amounts of 1 to 15 wt.%, preferably 2 to 12 wt.%, and in particular preferably 3 to 10 wt.%, in each case based on the total weight of the cosmetic composition.

[0135] Optionally, the cosmetic composition contains other cosmetically common additives such as thickeners.

[0136] Examples of thickeners preferably used are modified polysaccharides such as starch, cellulose, gum arabic and guar gum, e.g. polysaccharides with the INCI name cellulose gum, guar gum, xanthan gum or cassia gum.

[0137] Other examples of thickeners are hydrophobically modified non-ionic cellulose derivatives, e.g. the cellulose derivative with the INCI name hydroxyethylcellulose.

[0138] Other examples of thickeners are cross-linked acrylic and methacrylic acid polymers and derivatives of cross-linked acrylic and methacrylic acid polymers, e.g. polymers with the INCI name Carbomer.

[0139] Other examples of thickeners are agents that, in combination with surfactants, achieve a thickening effect. Examples include monoglycerides of fatty acids, mono / diglycerides of ethoxylated fatty acids, and ethoxylated fatty alcohols. INCI names of commonly used thickeners that, in combination with surfactants, achieve a thickening effect are PEG-120 Methyl Glucose Dioleate, PEG-150 Distearate, Myristyl Glycol, PEG-200 Glyceryl Palmitate, Laureth-4, and PEG-200 Glyceryl Palmitate.

[0140] Other examples of thickeners are salts, e.g. salts with the INCI name Sodium Chloride.

[0141] When thickeners are used, the cosmetic composition according to the invention preferably contains thickeners in amounts of 0.1 to 10% by weight, based on the total weight of the cosmetic composition.

[0142] Optionally, the cosmetic composition contains other cosmetically common additives such as film formers.

[0143] Preferred examples of film formers are polymers.

[0144] Examples of film-forming polymers that are preferably used are described in the "International Cosmetic Ingredient Dictionary & Handbook" of the Personal Care Product Council.

[0145] Examples of preferred film-forming polymers are acrylic acid polymer derivatives, acrylic acid copolymer derivatives, methacrylic acid derivatives and methacrylic acid copolymer derivatives.

[0146] Examples of preferred anionic polymers are copolymers of vinyl acetate and one or more acrylic acid, methacrylic acid monomers and their esters, e.g. polymers with the INCI name Acrylates / VA Copolymer.

[0147] Other examples of preferred film-forming polymers are copolymers of vinylpyrrolidone and one or more acrylic acid, methacrylic acid monomers and their esters, e.g. polymers with the INCI name Acrylates / VP Copolymer.

[0148] Other examples of preferred film-forming polymers are copolymers of tert-butyl acrylamide and one or more acrylic acid, methacrylic acid monomers and their esters, e.g. polymers with the INCI name Acrylates / t-Butylacrylamide Copolymer.

[0149] Other examples of preferred film-forming polymers are copolymers of vinyl acetate, crotonic acid and vinyl neodecanoate monomers, e.g. polymers with the INIC name VA / Crotonates / Vinyl Neodecanoate Copolymer.

[0150] Other examples of preferred film-forming polymers are copolymers of vinyl acetate, crotonic acid and vinyl neodecanoate monomers and vinyl silicones, e.g. polymers with the INCI name Crotonic Acid / Vinyl C8-C12 Isoalkyl Esters / VA / Bis-Vinyldimethicone Copolymer.

[0151] When film-forming polymers are used, the cosmetic composition according to the invention preferably contains film-forming polymers in amounts of 0.1 to 15 wt. %, preferably 0.2 to 10 wt. %, and in particular preferably 0.3 to 7 wt. %, in each case based on the total weight of the cosmetic composition.

[0152] Optionally, the cosmetic composition contains other cosmetically common additives such as moisturizing agents.

[0153] Examples of preferred moisturizing agents include glycerin, sorbitol, xylitol, polyethylene glycol, 1,2-propanediol, 1,3-propanediol or polypropylene glycol.

[0154] When moisturizing agents are used, the cosmetic composition according to the invention preferably contains moisturizing agents in amounts of 0.1 to 10 wt.%, preferably 0.2 to 8 wt.%, and in particular preferably 0.3 to 6 wt.%, in each case based on the total weight of the cosmetic composition.

[0155] Optionally, the cosmetic composition contains other cosmetically common additives such as pearlescent agents.

[0156] Examples of commonly used pearlescent agents are pearlescent pigments or glycol distearate.

[0157] When pearlescent agents are used, the cosmetic composition according to the invention preferably contains pearlescent agents in amounts of 0.1 to 7 wt.%, preferably 0.2 to 6 wt.%, and in particular preferably 0.3 to 5 wt.%, in each case based on the total weight of the cosmetic composition.

[0158] The cosmetic compositions are preferably produced by mixing at least one aqueous dispersion according to the invention of pre-crosslinked organopolysiloxanes with optionally at least one conditioning agent and optionally further cosmetically common additives in a cosmetically acceptable medium, preferably water.

[0159] The individual ingredients can be mixed together using a hot / hot, hot / cold or cold / cold process.

[0160] The addition of the dispersions of pre-crosslinked organopolysiloxanes according to the invention during the production of the cosmetic composition according to the invention preferably takes place at temperatures of no more than 50°C, more preferably at temperatures of no more than 40°C, and particularly preferably at temperatures of no more than 35°C. It preferably takes place at temperatures of at least 5°C, and more preferably at temperatures of at least 10°C.

[0161] The cosmetic composition according to the invention can be in the form of an emulsion, a suspension, a solution, a cream, a lotion, a foam, a stick, a bar of soap, a paste, or a gel.

[0162] The cosmetic composition according to the invention in the form of an emulsion can be in the form of a W / O emulsion (water-in-oil emulsion), an O / W emulsion (oil-in-water emulsion) or as a multiple emulsion.

[0163] If the aim is to produce a cosmetic composition containing an aqueous dispersion of pre-crosslinked organopolysiloxanes according to the invention in the form of an emulsion in a translucent or transparent appearance, aqueous dispersions of pre-crosslinked organopolysiloxanes according to the invention with particle sizes < 700 nm, preferably with particle sizes < 400 nm, and particularly preferably with particle sizes < 300 nm, are preferably used.

[0164] Another aspect of the invention is the use of the cosmetic composition according to the invention for the treatment of keratinous fibers, such as hair. Preferably, the cosmetic compositions are used for cleaning and conditioning keratinous fibers, such as hair, or for shaping keratinous fibers, such as hair.

[0165] Examples of products for cleaning and caring for hair include hair shampoos, rinse-off conditioners, treatments, masks, serums, foams, styling sprays, creams, gels, oils, split-end fluids, and dyes.

[0166] Another object of the invention is the use of the cosmetic composition according to the invention for conditioning keratinous fibers, such as hair, in particular to facilitate combing.

[0167] Another object of the invention is a method for treating keratinous fibers, preferably hair, by applying the cosmetic compositions according to the invention to the keratinous fibers, preferably hair, and then optionally rinsing with water.

[0168] In the examples described below, all parts and percentages refer to weight unless otherwise stated. Furthermore, all viscosity values ​​refer to a temperature of 25°C. Unless otherwise stated, the following examples are performed at atmospheric pressure (approximately 1020 hPa) and at room temperature (approximately 20°C), or at the temperature reached when the reactants are combined at room temperature without additional heating or cooling. Synthesis of oxalamido ethyl ester-terminated organopolysiloxanes S1-S2 Synthesis of the oxalamido-ethyl ester-terminated organopolysiloxane S1

[0169] An apparatus consisting of a 4-1 three-necked flask with magnetic stir bars, a magnetic stirrer, a reflux condenser, an internal thermometer, and a dropping funnel was inerted with nitrogen gas. Subsequently, 2679 g (18.45 mol) of diethyl oxalate (M = 146.14 g / mol; CAS No. 95-92-1; available from Sigma-Aldrich, Munich, Germany) were placed under a continuous nitrogen flow, and 600 g (4.07 mol) of (3-aminopropyl)dimethylmethoxysilane (M = 147.29 g / mol; CAS No. 31024-26-7; available from Gelest, Morrisville, USA) were added dropwise while stirring, ensuring that the temperature of the reaction mixture remained below 50°C. This resulted in a pale yellow, clear liquid, which was stirred for one hour at room temperature after the addition of the 3-molecule mixture was completed. The excess diethyl oxalate was then distilled off under vacuum (2 mbar). 1995 g of diethyl oxalate (13.65 mol) was obtained as a colorless, clear liquid.The liquid distillation residue was fractionally distilled at an internal temperature of 160°C. Within the boiling range of 136 to 141°C / 2 mbar vacuum, 949 g (3.84 mol) of the desired main product ethyl 2-((3-(methoxydimethylsilyl)propyl)amino)-2-oxoacetate (EtO-CO-CO-HN-CH₂CH₂CH₂-Si-Me₂(OMe)) were distilled. P1 (M = 247.37 g / mol) as a colorless, clear liquid. The yield was 94% based on the (3-aminopropyl)dimethylmethoxysilane used. 164.95 g (0.66 mol) P1740 g (10.00 mol Si) of α,ω-OH-terminated linear dimethylsiloxane (CAS No. 70131-67-8) with a viscosity of 50 mPas were placed in a 2-liter round-bottom flask. The round-bottom flask containing the reaction mixture was heated under rotation for 30 minutes in a 130°C oil bath at a vacuum of 6 mbar using a rotary evaporator. The vacuum was then broken, 0.02 g of a 40% solution of PNCl₂ in ethyl acetate was added, and the mixture was heated under vacuum for one hour using a rotary evaporator (130°C oil bath, 6 mbar vacuum). The vacuum was then broken again, 0.02 g of a 40% solution of PNCl₂ in ethyl acetate (10 ppm PNCl₂) was added, and the mixture was heated under vacuum for one hour on a rotary evaporator (130 °C oil bath, 6 mbar vacuum). The vacuum was then broken once more, 0.02 g of a 40% solution of PNCl₂ in ethyl acetate (10 ppm PNCl₂) was added, and the mixture was heated under vacuum for four hours on a rotary evaporator (130 °C oil bath, 6 mbar vacuum).After cooling to room temperature, 8 g of magnesium oxide (heavy MgO; CAS No. 1309-48-4; available from Sigma-Aldrich, Munich, Germany) were added to the contents of the flask and stirred for 1 h at room temperature. The suspension was then filtered under 6 mbar pressure through a Seitz® T-120 depth filter (available from Pall Corporation, New York, USA). 793 g of a colorless, clear oil with a viscosity of ~95 mPas were obtained. Synthesis of the oxalamido-ethyl ester-terminated organopolysiloxane S2

[0170] In a stirred-flask apparatus consisting of a 1-liter three-necked flask with heating mantle, mechanical stirrer, internal thermometer and water separator with reflux condenser, 400 g (5.41 mol Si) α,ω-OH-terminated linear dimethylsiloxane (CAS No. 70131-67-8) with a viscosity of 50 mPas and 19.8 g (0.08 mol) P1The solution was placed in the flask and heated to 80°C while stirring. After adding 50 mg of 100% PNCl₂, a vacuum (10 mbar) was applied and the contents were heated to 100°C. The resulting water was removed via a water separator. After 5 minutes, a vacuum of 40 mbar was established, and the mixture was stirred under these conditions for 30 minutes. The vacuum was then broken, another 25 mg of 100% PNCl₂ was added, and the mixture was heated at 100°C and 40 mbar while stirring. The vacuum was then broken again, another 25 mg of 100% PNCl₂ was added, and the mixture was heated further at 100°C and 40 mbar while stirring. The vacuum was then broken, the mixture cooled to an internal temperature of 70–80°C, and the contents of the flask neutralized by adding 2.5 g of anhydrous soda (light sodium carbonate; CAS No. 497-19-8; available from Sigma-Aldrich, Munich, Germany). Stirring continued for 30 minutes, followed by filtration. A colorless, clear oil with a viscosity of approximately 525 mPas was obtained. Production of the aminosilicone oil emulsions E1 - E3: Production of the aminosilicone oil emulsion E1:

[0171] Using an Ultra-Turrax T 50 emulsifier (Janke & Kunkel / IKA), 4.9 g of an 80% aqueous solution of isotridecyl decaethoxylate, commercially available under the trade name Lutensol TO 10 (BASF), and 1.6 g of deionized water are premixed at 4000 rpm. 34.9 g of a hydroxy / methoxy-terminated copolymer of 3-(2-aminoethylamino)propyl methylsiloxy and dimethylsiloxy units with an amine number of 0.14 meq / g and a viscosity of 4000 mm² / s (at 25°C) are added in three portions at a shear rate of 4000 rpm, resulting in a relatively solid, stiff preemulsion. It is diluted in portions with 57.5 g of fully demineralized water under low shear to the desired emulsion and mixed with 0.20 g of 80% acetic acid and 0.9 g of 2-phenoxyethanol.

[0172] The result is a smooth, low-viscosity, white silicone oil emulsion. E1with a solids content of 39.8% and a pH value of 5.0. A measurement of the particle size distribution yields a D50 value of 160 nm. Production of the aminosilicone oil emulsion E2:

[0173] In the working vessel of a laboratory planetary mixer (type Labmax, Molteni), 30.0 g of an 80% aqueous solution of isotridecyldecaethoxylate, commercially available under the trade name Lutensol TO 10 (BASF), 81.7 g of a trimethylsilyl-terminated copolymer of 3-(2-aminoethylamino)propyl-methylsiloxy and dimethylsiloxy units with an amine number of 0.6 meq / g and a viscosity of 2500 mm² / s (at 25°C) and 86.3 g of a trimethylsilyl-terminated polydimethylsiloxane with a viscosity of 60000 mm² / s (at 25°C) are premixed at 500 rpm. After adding 39.6 g of deionized water and 1.4 g of 80% acetic acid (at 500 rpm), the mixture is homogenized in three cycles at a shear rate of 2500 rpm, resulting in a soft to medium-firm stiff phase as a preemulsion. This is then diluted portionwise with 157.4 g of deionized water at a lower shear rate to achieve the desired emulsion, which is then treated with 3.6 g of 2-phenoxyethanol.

[0174] The result is a smooth, flowing, white silicone oil emulsion. E2 with a solids content of 48.9% and a pH value of 5.5.

[0175] A measurement of the particle size distribution yields a D50 value of 180 nm. Production of the amino silicone oil emulsion E3:

[0176] In the working vessel of a laboratory planetary mixer (type Labmax, Molteni), 32.0 g of an 80% aqueous solution of isotridecyldecaethoxylate, commercially available under the trade name Lutensol TO 10 (BASF), 44.0 g of a hydroxy / methoxy-terminated copolymer of 3-(2-aminoethylamino)propyl-methylsiloxy and dimethylsiloxy units with an amine number of 0.14 meq / g and a viscosity of 4000 mm² / s (at 25°C), and 132.0 g of a trimethylsilyl-terminated polydimethylsiloxane with a viscosity of 60000 mm² / s (at 25°C) are premixed at 500 rpm. After adding 20.0 g of deionized water and 0.3 g of 80% acetic acid (at 500 rpm), the mixture is homogenized in three cycles at a shear rate of 2500 rpm, resulting in a solid, stiff phase as a preemulsion. This is then diluted portionwise with 168.1 g of deionized water at a lower shear rate to obtain the desired emulsion, which is then treated with 3.6 g of 2-phenoxyethanol.

[0177] The result is a smooth, thin, white silicone oil emulsion. E3 with a solids content of 51.3% and a pH value of 5.0. A measurement of the particle size distribution yields a D50 value of 257 nm. Examples 1-4:

[0178] The following examples 1-4 represent manufacturing processes for the synthesis of aqueous dispersions of pre-crosslinked organopolysiloxanes according to the invention, which are used for the production of cosmetic compositions according to the invention. Example 1

[0179] Emulsion B 1 − a = B 1 − b

[0180] Using an Ultra-Turrax T 50 emulsifying device (Janke & Kunkel / IKA), 92.26 g of the aminosilicone oil emulsion are produced at 5000 rpm. E1 with 7.74 g of oxalamido ethyl ester-terminated organopolysiloxane S1 homogenized within one minute.

[0181] The result is a smooth, low-viscosity, white silicone oil emulsion. B1-a (= B1-b)with a solids content of 44.5% and a pH value of 5.0. A measurement of the particle size distribution yields a D50 value of 141 nm.

[0182] By evaporating the emulsion, after a drying time of 24 hours at 25°C, a pronounced, whitish, somewhat soft, elastic film with a slightly sticky surface is obtained. Emulsion B1-c

[0183] Using an Ultra-Turrax T 50 emulsifying device (Janke & Kunkel / IKA), 96.16 g of the aminosilicone oil emulsion are produced at 5000 rpm. E1 with 3.84 g of oxalamido ethyl ester-terminated organopolysiloxane S1 homogenized within one minute.

[0184] The result is a smooth, low-viscosity, white silicone oil emulsion. B1-c with a solids content of 42.1% and a pH value of 5.5. A measurement of the particle size distribution yields a D50 value of 123 nm.

[0185] By evaporating the emulsion, a pronounced, whitish, somewhat soft, elastic film is obtained after a drying time of 24 hours at 25°C. Example 2 Emulsion B2

[0186] Using an Ultra-Turrax T 50 emulsifying device (Janke & Kunkel / IKA), 96.08 g of the aminosilicone oil emulsion are produced at 5000 rpm. E2 with 3.92 g of oxalamido ethyl ester-terminated organopolysiloxane S1 homogenized within one minute.

[0187] The result is a smooth, flowing, white silicone oil emulsion. B2 with a solids content of 50.9% and a pH value of 6.5. A measurement of the particle size distribution yields a D50 value of 230 nm.

[0188] By evaporating the emulsion, a pronounced, whitish, somewhat soft, elastic film is obtained after a drying time of 24 hours at 25°C. Example 3 Emulsion B3

[0189] Using an Ultra-Turrax T 50 emulsifying device (Janke & Kunkel / IKA), 98.22 g of the aminosilicone oil emulsion are produced at 5000 rpm. E3 with 1.78 g of oxalamido ethyl ester-terminated organopolysiloxane S1 homogenized within one minute.

[0190] The result is a smooth, thin, white silicone oil emulsion. B3 with a solids content of 52.2% and a pH value of 4.5. A measurement of the particle size distribution yields a D50 value of 210 nm.

[0191] By evaporating the emulsion, after a drying time of 24 hours at 25°C, a pronounced, whitish, somewhat soft, elastic film with a slightly sticky surface is obtained. Example 4 Emulsion B4

[0192] Using an Ultra-Turrax T 50 emulsifying device (Janke & Kunkel / IKA), 85.69 g of the aminosilicone oil emulsion are produced at 5000 rpm. E1 with 14.31 g of oxalamido ethyl ester-terminated organopolysiloxaneS2 homogenized within one minute.

[0193] The result is a smooth, low-viscosity, white silicone oil emulsion. B4 with a solids content of 48.4% and a pH value of 5.5. A measurement of the particle size distribution yields a D50 value of 192 nm.

[0194] By evaporating the emulsion, a pronounced, whitish, somewhat soft, elastic film is obtained after a drying time of 24 hours at 25°C. Comparison test V1:

[0195] The following comparative experiment V1 represents a manufacturing process for the synthesis of aqueous, non-inventive emulsions (crosslinking with non-inventive diethyl oxalate according to US5039738 A): Using an Ultra-Turrax T 50 emulsifying device (Janke & Kunkel / IKA), 99.6 g of the aminosilicone oil emulsion are produced at 5000 rpm. E1homogenized with 0.4 g of diethyl oxalate within one minute. A smooth, low-viscosity, white silicone oil emulsion is obtained. V1 with a solids content of 40.0% and a pH value of 4.5. A measurement of the particle size distribution yields a D50 value of 71 nm. Evaporation of the emulsion, after a drying time of 24 hours at 25 °C, results in a white, opaque, pasty layer that adheres poorly to glass and aluminum. Comparison test V2:

[0196] The following comparative experiment V2 represents a manufacturing process for the synthesis of aqueous, non-inventive emulsions (crosslinking with non-inventive diethyl L-tartrate: according to WO20239229 A1): Using an Ultra-Turrax T 50 emulsifying device (Janke & Kunkel / IKA), 99.4 g of the aminosilicone oil emulsion are produced at 5000 rpm. E1homogenized with 0.6 g of diethyl L-tartrate within one minute. A smooth, low-viscosity, white silicone oil emulsion is obtained. V2 with a solids content of 40.2% and a pH of 5.5. A measurement of the particle size distribution yields a D50 value of 135 nm. Evaporation of the emulsion, after a drying time of 24 hours at 25°C, results in a soft, milky-white, elastic film with a slightly sticky surface. Rheology of elastomer films after removal of water:

[0197] A Teflon ring with a 40 mm inner diameter is placed on a 65 mm diameter round glass plate to form a mold. 2.5 g of the emulsion to be measured is weighed into this ring onto the glass plate, ensuring it is free of air bubbles. The cast emulsion is then allowed to dry at 25°C and 101.425 kPa. It is important to ensure that the mold containing the cast emulsion is placed on a level, flat surface to allow for the formation of a uniformly thick film. After drying, a film approximately 0.5 mm thick is obtained.

[0198] After a one-week incubation period at 25°C, the resulting films were rheologically analyzed. Measurements were performed using an Anton Paar "MCR 302" rheometer, employing a PP12.5 plate-to-plate measuring system with a gap height of 0.5 mm. The instrument was calibrated using standard oil 10000 from the German Federal Institute of Physics and Metrology (PTB). The measurement temperature was 25.00°C ± 0.05°C.

[0199] The values ​​of the storage modulus G', loss modulus G'', and loss factor tan δ listed in Table 1 can be calculated by measuring the shear stress τ and the phase shift angle δ after applying a sinusoidal deformation. The measured values ​​listed in Table 1 were obtained at a frequency of 1 Hz and a deformation of 0.1%. At this deformation, the measured samples lie within the linear viscoelastic range. In this case, tan δ = G'' / G'. If tan δ < 1, the elastic character of the sample predominates; if tan δ > 1, the viscous character of the sample predominates.

[0200] The results of the rheology measurements for the elastomer films of the examples according to the invention B1 until B4, the comparative trials V1 and V2 as well as the uncrosslinked aminosilicone oil emulsions E1 until E3 are summarized in Table 1. Table 1: Rheological data of the elastomer films Example / Comparison Memory module G' [Pa] Loss modulus G" [Pa] tan δ B1-a = B1-b 8409 4094 0,49 B1-c 13853 3872 0,28 B2 3465 997 0,29 B3 1881 1127 0,60 B4 3386 1676 0,50 V1 3182 3904 1,23 V2 17196 5809 0,34 E1 28 205 7,28 E2 14 138 9,99 E3 140 502 3,60

[0201] Table 1 shows that the emulsions according to the invention B1 up to B4 with oxalamido-ethyl ester-terminated organopolysiloxanes S1 or S2 As a crosslinking component, elastic films form after removal of water, since tan δ < 1.

[0202] The non-inventive emulsion V1 After removing water, no elastic film formation is shown, since tan δ is greater than 1.

[0203] The non-inventive emulsion V2 with diethyl L-tartrate as a crosslinking component, shows the formation of an elastic film after removal of water according to WO20239229 A1, since tan δ < 1.

[0204] The evaporated, pure aminosilicone oil emulsions E1 until E3No film formation is observed after the removal of the water, as tan δ is significantly greater than 1 in all cases. This indicates that the addition of a crosslinking agent is necessary to achieve film formation. Test methods for assessing the effectiveness of cosmetic compositions: natural hair

[0205] The application behavior of the cosmetic composition and its effect on combability and softness were assessed on Caucasian hair, available from Kerling International Haarfabrik GmbH. Undamaged natural hair wefts are cleaned before use and may be damaged by bleaching in a further process step. Basic cleaning

[0206] For cleaning, the undamaged hair wefts are soaked for one hour in a methyl isobutyl ketone solution and shaken. After removing the solvent, the hair wefts are washed twice with 3 ml of a 25% ammonium lauryl sulfate solution, STEPANOL® ALS 25, STEPAN Company, followed by 30°C deionized water. During this process, the wefts are detangled with a wide-tooth comb. The hair wefts are then placed in a large beaker of deionized water for one hour, removed, and rinsed again under running deionized water. After this initial cleaning, the wefts are conditioned for at least 12 hours at 23°C and 50% relative humidity before further use and are combed. Bleaching hair - causing damaged hair

[0207] Damaged hair is created by bleaching purified natural hair wefts (Kerling International Haarfabrik GmbH, Euro-Natur-Haar, color 6 / 0, 20 cm, weft weight 2 g). For this, five hair wefts at a time are immersed for 30 minutes in a solution of 30% hydrogen peroxide and 25% ammonia (ratio 33.5:1). The hair is then thoroughly rinsed with demineralized water and washed twice with 3 ml of a 25% ammonium lauryl sulfate solution, STEPANOL® ALS 25, STEPAN Company, and 30°C warm demineralized water. Afterward, the hair wefts are placed in a large beaker of demineralized water for one hour, removed, and rinsed again under running demineralized water. Before further treatment, the bleached wefts are conditioned for at least 12 hours at 23°C and 50% humidity and combed before use. Combing force measurement:

[0208] To determine the combing force of wet and dry hair, bleached or unbleached hair wefts (Kerling International Haarfabrik GmbH, Euro-Natur-Haar, color 6 / 0, 20 cm, weft weight 2 g) were used. The combing force was measured using the double-comb method according to YK Kamath and Hans-Dietrich Weigmann, J. Soc. Cosmet. Chem., 37, 111-124, 1986, with an Instron 3343 tensile-extension machine. First, the wet and dry combing force was determined along the measuring section on untreated hair wefts. Then, the hair wefts were treated with a cosmetic composition according to the invention, and the force absorbed during the combing process was determined. The measured value is the reduction in combing force along the measuring section (work) between the treated and untreated hair wefts. The average value from five hair wefts was calculated. The reduction in combing force is given as a percentage. suppleness / Softness (according to tensile test):

[0209] To determine hair softness, bleached or unbleached hair wefts (Kerling International Haarfabrik GmbH, Euro-Natural Hair, color 6 / 0, 20 cm, weft weight 2 g) were used. Hair softness in the dry state was determined using an Instron 3343 tensile testing machine by correlating the required tensile force with the parameters of bending stiffness and surface roughness of the hair bundle. These two parameters, in turn, correlate with hair softness. For this purpose, an untreated hair weft was clamped in a measuring setup consisting of five offset, opposing bars. The shape of the hair weft in this initial position is a kind of double-S. After this preparation, the hair weft is pulled out of the measuring setup in one direction, and the required force along the measuring path is evaluated as work.The hair wefts are then treated with a cosmetic composition according to the invention, and the force absorbed when pulling the hair weft is determined by the measuring device along the measuring distance. The measured value is the reduction in tensile force (work) along the measuring distance, which results between the treated and untreated hair weft. A high reduction in tensile force (work) corresponds to a good soft feel or high suppleness. The average value from five hair wefts is calculated. Softness (according to panel test):

[0210] To assess the softness of hair wefts, their haptic properties are evaluated by experts (trained panelists). A pairwise comparison of hair wefts is performed, for example, comparing shampoo-treated hair to untreated hair. The number of weft pairs evaluated is at least three, and the number of panelists is at least five. The evaluation was based on hair wefts from Kerling International Haarfabrik GmbH (Euro-Natural Hair, color 6 / 0, 20 cm, weft weight 2 g). Shampoo washing procedure:

[0211] Apply 0.2 g of shampoo per gram of hair to a clean, moistened hair weft. Massage the shampoo in towards the ends of the hair for 30 seconds. Then rinse the hair weft under running, demineralized water for 30 seconds and detangle it with a wide-tooth comb. Repeat this procedure twice. The final time, extend the rinsing time to 60 seconds. Finally, dry the hair weft for at least 12 hours at a relative humidity of 50% and a temperature of 23°C. Washing-up procedure with conditioner:

[0212] Apply 0.3 g of rinse-off conditioner per gram of hair to a clean, moistened hair weft. Massage the rinse-off conditioner in towards the ends of the hair for 120 seconds. Then rinse the hair weft under running, demineralized water for 60 seconds and detangle with a wide-tooth comb. Repeat this procedure. Finally, dry the hair weft for at least 12 hours at 50% humidity and 23°C. Determination of the amount of silicon deposited on the hair surface in ppm (silicon deposition):

[0213] To determine the amount of silicone deposited on the hair surface, an energy-dispersive X-ray fluorescence spectrometer (AMETEK, XEPOS) is used. The hair bundles are placed in a specially designed sample holder with a circular measuring area of ​​12 mm diameter. The hair surface in the area of ​​the measuring area is smooth, and the hairs are aligned parallel to each other. The sample is excited under a helium atmosphere using a palladium tube (17.05 kV, 2.0 mA). The excitation duration is 300 s. Control samples (natural hair wefts) are measured regularly. Any deviations are corrected for drift using glass tablets. Hair wefts loaded with polydimethylsiloxane in the range of 50 to 2000 ppm (verified by atomic absorption spectroscopy) were used as calibration standards.

[0214] To determine the effectiveness of silicone deposition, the amount of silicon (Si) in ppm of a cleaned hair bundle is first determined = blank value. The same hair bundle is then treated, for example, by washing with shampoo. The amount of Si in ppm is determined again = sample value. The deposited amount of Si in ppm is calculated by subtracting the sample value from the blank value. Each hair weft is measured in the center of its front and back surfaces. The result is the average of three hair wefts. Simulation of shampoo washing by stirring hair wefts in a surfactant solution:

[0215] Many users desire the persistence of cosmetic effects after using a hair conditioning product, such as improved hair softness, reduced wet combing difficulty, and preservation of hair color despite several subsequent shampoo washes. To assess the persistence of cosmetic effects after treating hair with a cosmetic composition according to the invention, a method was developed that simulates successive shampoo washes. For this purpose, a treated hair weft is placed in a 100 ml screw-top jar containing 50 ml of a five percent solution of ammonium lauryl sulfate, obtained by diluting STEPANOL® < ALS 25, STEPAN Company, at 40°C. The mixture is then shaken for a predetermined time in an incubator shaker (Heidolph Unimax 1010 + Incubator 1000) at a speed of 250 rpm, also at 40°C.After shaking, the wefts are rinsed for one minute with 30°C warm, fully demineralized water and dried. Curl Retention Test at High Humidity:

[0216] The curl retention test at high humidity allows for the evaluation of hair care and styling products with regard to their curl-forming properties. This model for determining hair fixation records the percentage change from initial to final length of precisely prepared curls compared to the length of hair wefts. The curl retention properties of hair care and styling products at high humidity are monitored over a period of seven hours at 23°C and 90% relative humidity.

[0217] 15 cm long hair wefts of brown European hair, weighing 3.5 g each, are assembled into bundles, tied with twine, and permanently fixed with a suitable adhesive. Each weft is washed twice with 3 ml of a 25% ammonium lauryl sulfate solution, STEPANOL® ALS 25, from STEPAN Company, followed by 30°C deionized water. The wefts are combed and dried. Once dry, they are sprayed with 20 pumps of a 3% active pump spray, combed once, and then wound onto a 1.4 cm diameter plastic rod. The rod is temporarily secured with a sleeve and dried overnight at 50°C.

[0218] The curls are carefully stripped from the plastic rods. After a short cooling period, the curls are attached to a scaled hanging device in a climate chamber at 23°C and 90% relative humidity. The initial length of each curl was determined and recorded beforehand. At specific time intervals, the curl lengths—that is, the change from the initial length—are measured over a period of 7 hours.

[0219] The calculation is performed according to equation (GI), %CURL RETENTION = L − L t L − L 0 × 100 where L = Length of the hair weft Lo = Initial length of the curl Lt = Length of the curl after / during measurement mean.

[0220] The higher the percentage value for curl retention after a time t, the better the shaping and fixing properties of the cosmetic formulation. The curls droop less. Examples of cosmetic compositions:

[0221] Pre-crosslinked emulsions are preferably emulsions that form elastic films after removal of water and exhibit a tan δ < 1 in rheological measurements.

[0222] Examples A1-a, A1-c and A2-a (Rinse-Off Conditioner) The following examples represent cosmetic compositions according to the invention. A1-a, A1-c and A2-a according to Table 2 containing the pre-crosslinked emulsions B1-a, B1-c and B2 from the corresponding examples. The active content of organopolysiloxanes in the cosmetic compositions is 0.5%. Manufacturing instructions:

[0223] Water is placed in the container and heated to 75°C while stirring. 2.0 parts of hydroxyethylcellulose are added. When 65°C is reached, 0.5 parts of polysorbate 80, 0.5 parts of stearyl alcohol, 0.5 parts of cetyl alcohol, and 0.2 parts of behentrimonium chloride are added. The mixture is stirred until 75°C is reached and the ingredients are dissolved. The mixture is then cooled. During cooling, 0.1 parts of citric acid and 0.2 parts of tetrasodium EDTA are added. At 35°C, 0.9 parts of phenoxyethanol and ethylhexylglycerin are added. While continuing to stir, the emulsion from the examples is added. The mixture is homogenized for 15 minutes while stirring. Table 2: A1-a, A1-c A2-a Rinse-off conditioner and Ingredients (INCI name) Example. A1-a [Weight parts] Example. A1-c [Weight parts] Example. A2-a [Weight parts] Water ad 100 ad 100 ad 100 Hydroxyethylcellulose 1)< 2,0 2,0 2,0 Cetyl Alcohol 2)< 0,5 0,5 0,5 Polysorbate 80 3)< 0,5 0,5 0,5 Behentrimonium Chloride 4)< 0,2 0,2 0,2 Stearyl Alcohol 5)< 0,5 0,5 0,5 Citric Acid 6)< 0,1 0,1 0,1 Tetrasodium EDTA 7)< 0,2 0,2 0,2 emulsion B1-a from example 1 1,43 emulsion B1-c from example 1 1,43 emulsion B2 from example 2 1,16 Phenoxyethanol, ethylhexylglycerol 8)< 0,9 0,9 0,9 The raw materials listed in Table 2 are available under the following trade names: 1) Hydroxyethylcellulose: Natrosol 250 HR, Ashland 2) Cetyl alcohol: Cetyl Alcohol, Merck KGaA 3) Polysorbate 80: Tween™< 80, Croda GmbH 4) Behentrimonium Chloride: Genamin®< KDMP, Clariant GmbH 5) Stearyl alcohol: Stearyl Alcohol, Merck KGaA 6) Citric Acid: Citric Acid, Sigma 7) Tetrasodium EDTA: EDETA®< B Powder, BASF Corporation 8) Phenoxyethanol, Ethylhexylglycerin: Euxyl PE 9010, Schülke & Mayr

[0224] Comparison test VA1 and VA2 (Rinse-off conditioner) The following comparative tests VA1 and VA2 represent non-inventive cosmetic compositions containing the non-pre-crosslinked aqueous dispersions E1 and E2 from the corresponding examples. The active content of organopolysiloxanes in the cosmetic compositions is 0.5%.

[0225] During the production of the cosmetic compositions for the comparative trials VA1 and VA2 The working methods of the examples were explained. A1-a, A1-c and A2-a repeated, with the modification that instead of the emulsions B1-a, B1-c and B2 (Emulsions of pre-crosslinked organopolysiloxanes according to the invention) the uncrosslinked emulsions E1 and E2 be used. Manufacturing instructions:

[0226] Water is placed in the water and heated to 75°C while stirring. 2.0 parts of hydroxyethylcellulose are added. When 65°C is reached, 0.5 parts of polysorbate 80, 0.5 parts of stearyl alcohol, 0.5 parts of cetyl alcohol, and 0.2 parts of behentrimonium chloride are added. The mixture is stirred until 75°C is reached and the ingredients are dissolved. The mixture is then cooled. During cooling, 0.1 parts of citric acid and 0.2 parts of tetrasodium EDTA are added. At 35°C, 0.9 parts of phenoxyethanol and ethylhexylglycerin are added. While continuing to stir, the emulsion is added according to Table 3 for the comparative tests. The mixture is homogenized for 15 minutes while stirring. Table 3: VA1 VA2 Rinse-off conditioner and Ingredients (INCI name) Comparative attempt VA1 [Weight parts] Comparative attempt VA2 [Weight parts] Water ad 100 ad 100 Hydroxyethyl cellulose 1)< 2,0 2,0 Cetyl Alcohol 2)< 0,5 0,5 Polysorbate 80 3)< 0,5 0,5 Behentrimonium Chloride 4)< 0,2 0,2 Stearyl Alcohol 5)< 0,5 0,5 Citric Acid 6)< 0,1 0,1 Tetrasodium EDTA 7)< 0,2 0,2 Emulsion E1 1,43 Emulsion E2 1,16 Phenoxyethanol, ethylhexylglycerol 8)< 0,9 0,9 The raw materials listed in Table 3 are available under the following trade names: 1) Hydroxyethylcellulose: Natrosol 250 HR, Ashland 2) Cetyl alcohol: Cetyl Alcohol, Merck KGaA 3) Polysorbate 80: Tween™< 80, Croda GmbH 4) Behentrimonium Chloride: Genamin®< KDMP, Clariant GmbH 5) Stearyl alcohol: Stearyl Alcohol, Merck KGaA 6) Citric Acid: Citric Acid, Sigma 7) Tetrasodium EDTA: EDETA®< B Powder, BASF Corporation 8) Phenoxyethanol, Ethylhexylglycerin: Euxyl PE 9010, Schülke & Mayr

[0227] Comparison test VA1-DEO (Rinse-off conditioner) The following comparison test VA1-DEO This represents a non-inventive cosmetic composition containing an aqueous dispersion of a pre-crosslinked organopolysiloxane. The active content of organopolysiloxanes in the cosmetic composition is 0.5%.

[0228] During the production of the cosmetic composition of the comparative experiment VA1-DEO The working methods of the examples were explained. VA1 and VA2 repeated, with the modification that instead of the emulsions E1 and E2 (Emulsions of non-pre-crosslinked organopolysiloxanes) the pre-crosslinked, non-inventive emulsion V1 is used. Manufacturing instructions:

[0229] Water is placed in the water and heated to 75°C while stirring. 2.0 parts of hydroxyethylcellulose are added. When 65°C is reached, 0.5 parts of polysorbate 80, 0.5 parts of stearyl alcohol, 0.5 parts of cetyl alcohol, and 0.2 parts of behentrimonium chloride are added. The mixture is stirred until 75°C is reached and the ingredients are dissolved. The mixture is then cooled. During cooling, 0.1 parts of citric acid and 0.2 parts of tetrasodium EDTA are added. At 35°C, 0.9 parts of phenoxyethanol and ethylhexylglycerin are added. While continuing to stir, the emulsion is added according to Table 4 for the comparative test. The mixture is homogenized for 15 minutes while stirring. Table 4: VA1-DEO Rinse-Off Conditioner Ingredients (INCI name) Comparative attempt VA1-DEO [Weight parts] Water ad 100 Hydroxyethyl cellulose 1)< 2,0 Cetyl Alcohol 2)< 0,5 Polysorbate 80 3)< 0,5 Behentrimonium Chloride 4)< 0,2 Stearyl Alcohol 5)< 0,5 Citric Acid 6)< 0,1 Tetrasodium EDTA 7)< 0,2 Emulsion V1 1,43 Phenoxyethanol, ethylhexylglycerol 8)< 0,9 The raw materials listed in Table 4 are available under the following trade names: 1) Hydroxyethylcellulose: Natrosol 250 HR, Ashland 2) Cetyl alcohol: Cetyl Alcohol, Merck KGaA 3) Polysorbate 80: Tween™< 80, Croda GmbH 4) Behentrimonium Chloride: Genamin®< KDMP, Clariant GmbH 5) Stearyl alcohol: Stearyl Alcohol, Merck KGaA 6) Citric Acid: Citric Acid, Sigma 7) Tetrasodium EDTA: EDETA®< B Powder, BASF Corporation 8) Phenoxyethanol, Ethylhexylglycerin: Euxyl PE 9010, Schülke & Mayr

[0230] Comparison of the rinse-off conditioners of the inventive examples A1-a, A1-c and A2-a with the comparison tests VA1 and VA2

[0231] The examples and comparisons given differ in that, in the case of the examples... A1-a, A1-c and A2-a aqueous dispersions of pre-crosslinked organopolysiloxanes according to the invention were used in the comparative tests. VA1 and VA2 Each is an analogous aqueous dispersion of the corresponding non-pre-crosslinked organopolysiloxanes. The active content of organopolysiloxanes in the cosmetic compositions is 0.5%.

[0232] The following examples / comparisons correlate in direct comparison: Example A1-a - Comparative experiment VA1 Example A1-c - Comparative experiment VA1 Example A2-a - Comparative experiment VA2

[0233] Wet combing strength after treatment of damaged hair with rinse-off conditioner and after simulating several shampoo washes by stirring the hair in an aqueous surfactant solution (persistence effect) Examples A1-a and A1-c - Comparative experiment VA1

[0234] The use of aqueous dispersion B1-a and B1-cof organopolysiloxanes pre-crosslinked according to the invention in the rinse-off conditioner (examples) A1-a and A1-c) This leads to an improvement in conditioning properties, such as the reduction of combing forces in the wet state, compared to the non-inventive rinse-off conditioner from example. VA1, the dispersion of a non-pre-crosslinked organopolysiloxane E1 The aim of the rinse-off conditioner according to the invention is also to ensure that the conditioning properties are retained even after several shampooing sessions. In this example, the shampooing process is simulated by stirring hair bundles treated with rinse-off conditioner in a surfactant solution for four hours. Details of this treatment are described above. Test methods described.

[0235] The results of the determination of combing power in the wet state are shown below for the rinse-off conditioners of the examples. A1-a, A1-c and VA1listed in Table 5. Table 5: Rinse-Off Conditioner / Results of the reduction in wet combing strength on damaged Caucasian hair after treatment with a rinse-off conditioner according to the invention, compared to a non-inventive conditioner, and after simulating several shampoo washes by stirring the hair in an aqueous surfactant solution for four hours. All results refer to a comparison with untreated hair wefts. Example / Compare Reduction in wet combing strength after conditioner treatment [%] Reduction in wet combing strength after conditioner treatment and subsequent stirring of the hair in an aqueous surfactant solution (persistence test) [%] A1-a 84 39 A1-c 81 31 VA1 79 21

[0236] By treatment with the rinse-off conditioner according to the invention, comprising an aqueous emulsion of a pre-crosslinked organopolysiloxane B1-a (Example A1-a A significant reduction of 84% in the wet combing strength of the hair wefts can be measured. In particular, a high conditioning effect is retained after stirring the treated hair in a surfactant solution, which is reflected in a remaining wet combing strength reduction of 39%. Similarly, treatment with a rinse-off conditioner according to the invention containing the aqueous emulsion of a pre-crosslinked organopolysiloxane results in B1-c (Example A1-cA significant reduction in wet combing strength of 81% was measured for the hair wefts. After stirring the treated hair in a surfactant solution, a reduction in wet combing strength of 31% remained.

[0237] Hair treated with a non-inventive rinse-off conditioner containing the emulsion E1 (Comparative example) VA1 ) show a slightly reduced wet combing force reduction of 79%. However, after surfactant treatment, a result is obtained that is comparable to example . A-1a and A-1c Significantly lower reduction in wet combing strength of 21%. The treatment of the hair in surfactant solution represents a simulation of several hair washes with shampoo and demonstrates that the rinse-off conditioners according to the invention show better wash resistance and the conditioning properties are retained longer than with a hair treatment using a non-inventive rinse-off conditioner.

[0238] Comparison of silicone deposition after treatment of damaged hair with rinse-off conditioner and after simulating several shampoo washes by stirring the hair in an aqueous surfactant solution for four hours. Example A2-a - Comparative experiment VA2

[0239] As a further criterion, the efficiency of silicone deposition on damaged hair after treatment with rinse-off conditioners was evaluated. Additionally, the amount of the conditioning organopolysiloxane remaining on the hair surface after simulating shampooing by stirring the hair in a surfactant solution for four hours was investigated. The results are summarized in Table 6. The determination of silicone deposition is described above. Test methods described. Table 6: Rinse-Off Conditioner / Silicondeponierung Example / Compare Silicon deposition [ppm] Silicone deposition after stirring hair in an aqueous surfactant solution (persistence test) [ppm] A2-a 55 34 VA2 36 21

[0240] Table 6 shows that the deposition of the silicone - even after shampoo washing - in the example according to the invention. A2-a both more effective and more resistant to shampoo washing compared to the non-inventive comparison test VA2 is. Comparison of the rinse-off conditioner of the inventive example A1-a with the comparison test VA1-DEO

[0241] The example given and the comparison attempt differ in that, in the case of the example... A1-a An aqueous dispersion of pre-crosslinked organopolysiloxanes according to the invention was used in a comparative test. VA1-DEO An analogous, non-inventive aqueous dispersion of the corresponding pre-crosslinked organopolysiloxanes. The active content of organopolysiloxanes in the cosmetic compositions is 0.5%.

[0242] Wet combing strength after treatment of damaged hair with rinse-off conditioner and after simulating several shampoo washes by stirring the hair in an aqueous surfactant solution (persistence effect) Example A1-a - Comparative experiment VA1-DEO

[0243] The use of aqueous dispersion B1-a of organopolysiloxanes pre-crosslinked according to the invention in the rinse-off conditioner (example) A1-a ) leads to an improvement in conditioning properties such as the reduction of combing forces in the wet state compared to the non-inventive rinse-off conditioner from example. VA1-DEO,the dispersion of a pre-crosslinked organopolysiloxane (Comparison attempt V1) The aim of the rinse-off conditioner according to the invention is also to ensure that the conditioning properties are retained even after several shampooing sessions. In this example, the shampooing process is simulated by stirring hair bundles treated with the rinse-off conditioner in a surfactant solution for four hours. Details of this treatment are described above. Test methods described.

[0244] The results of the determination of combing power in the wet state are shown below for the rinse-off conditioners of the examples. A1-a and VA1-DEO listed in Table 7. Table 7: Rinse-Off Conditioner / Results of the reduction in wet combing strength on damaged Caucasian hair after treatment with a rinse-off conditioner according to the invention, compared to a non-inventive conditioner, and after simulating several shampoo washes by stirring the hair in an aqueous surfactant solution for four hours. All results refer to a comparison with untreated hair wefts. Example / Compare Reduction in wet combing strength after conditioner treatment [%] Reduction in wet combing strength after conditioner treatment and subsequent stirring of the hair in an aqueous surfactant solution (persistence test) [%] A1-a 84 39 VA1-DEO 77 20

[0245] By treatment with the rinse-off conditioner according to the invention, comprising an aqueous emulsion of a pre-crosslinked organopolysiloxane B1-a (Example A1-aA significant reduction of 84% in the wet combing strength of the hair wefts can be measured. In particular, a high conditioning effect is retained after stirring the treated hair in a surfactant solution, which is reflected in a remaining wet combing strength reduction of 39%.

[0246] Hair treated with a non-inventive rinse-off conditioner VA1-DEO containing the emulsion made of Comparison example V1 They exhibit a slightly reduced wet combing force reduction of 77%. However, after surfactant treatment, a difference is achieved compared to example [example missing]. A-1aSignificantly lower reduction in wet combing strength of 20%. The treatment of the hair in surfactant solution represents a simulation of several hair washes with shampoo and demonstrates that the rinse-off conditioner according to the invention shows better wash resistance and the conditioning properties are retained longer than with a hair treatment using a non-inventive rinse-off conditioner. Example A3-a Cosmetic composition: Shampoo

[0247] The following example represents a cosmetic composition according to the invention. A3-a containing the emulsion B3. The comparative example VA3This represents a commercially available shampoo formulation containing an emulsion of a dimethicone (dimethylpolysiloxane; BELSIL® DM 5102 E (available from Wacker Chemie AG)) with a viscosity of 60,000 mm² / s (at 25°C). The active content of organopolysiloxanes in the cosmetic composition is 1.3%.

[0248] The composition of the shampoos is summarized in Table 8. Manufacturing instructions:

[0249] 32.11 parts of water are placed in a container and heated to 50°C while stirring. At this temperature, 0.20 parts of guar hydroxypropyltrimonium chloride, 6.06 parts of sodium lauryl sulfate, 29.90 parts of sodium laureth sulfate, 0.05 parts of citric acid, and 5.0 parts of cocamidopropyl betaine are added. The mixture is stirred until 50°C is reached and the ingredients are dissolved. The mixture is then cooled. In a separate container, 20.0 parts of water are placed in a container, 0.60 parts of carbomer are added while stirring, and the mixture is stirred until homogeneous. 0.06 parts of lactic acid are then added. This mixture is added to the first mixture. At 40°C, 0.95 parts of phenoxyethanol and ethylhexylglycerin are added. While stirring further, 0.30 parts of C12-13 alkyl lactate and 2.91 parts of the emulsion according to the invention are added. B3or 2.60 parts of the non-inventional dimethicone emulsion BELSIL® < DM 5102 E, 0.40 parts sodium hydroxide, and 0.66 parts sodium chloride. The required pH value of 6.5 can be adjusted, if necessary, by adding sodium hydroxide. Table 8: A3-a VA3 Shampoo formulation and Ingredients (INCI name) Example A3-a [Weight parts] comparative experiment VA3 [Weight parts] Citric Acid 1)< 0,05 0,05 Cocamidopropyl Betaine 2)< 5,00 5,00 Sodium Laureth Sulfate 3)< 29,90 29,90 Guar Hydroxypropyltrimonium Chloride 4)< 0,20 0,20 Sodium Lauryl Sulfate 5)< 6,06 6,06 Aqua (DI Water) 32,11 32,11 Carbomer 6)< 0,60 0,60 Lactic Acid 7)< 0,06 0,06 Aqua (DI Water) 20,00 20,00 Phenoxyethanol, ethylhexylglycerol 8)< 0,95 0,95 C12-13 Alkyl Lactate 9)< 0,30 0,30 emulsion B3 from example 3 2,91 BELSIL ®< DM 5102 E 10)< (dimethicone emulsion) 2,60 Sodium Hydroxide 11)< 0,40 0,40 Sodium Chloride 12)< 0,66 0,66 1) Citric Acid: Citric Acid, Sigma 2) Cocamidopropyl Betaine: Genagen CAB 818 30%, Clariant 3) Sodium Laureth Sulfate: Genapol ®< LRO 26.5%, Clariant 3) Glycol Distearate: Genapol ®< PMS, Clariant GmbH 4) Guar Hydroxypropyltrimonium Chloride: N-Hance ®< BF 13, Ashland 5) Sodium lauryl sulfate: Texapon K 12 G, BASF 6) Carbomer: Carbopol 980, Lubrizol 7) Lactic acid: L-(+)lactic acid, 90%, Bernd Kraft GmbH 8) Phenoxyethanol, ethylhexylglycerin: Euxyl PE 9010, Schülke & Mayr 9) C12-13 alkyl Lactates: Ceraphyl ™< 41 ester, Ashland 10) BELSIL ®< DM 5102 E, available from Wacker Chemie AG 11) Sodium Hydroxide: Sodium hydroxide, Sigma-Aldrich 12) Sodium Chloride: Pure sodium chloride, Bernd Kraft GmbH Comparison of the shampoos of the inventive example A3-a with the comparison test VA3

[0250] The example given and the comparison attempt differ in that, in the case of the example... A-3a An aqueous dispersion of pre-crosslinked organopolysiloxanes was used. In the comparative experiment VA3The commercially available aqueous dimethylpolysiloxane emulsion BELSIL® DM 5102 E (Wacker Chemie AG) is used, which contains a dimethicone (dimethylpolysiloxane) with a viscosity of 60,000 mm² / s as a conditioning agent. The active content of organopolysiloxanes in the cosmetic compositions is 1.3%.

[0251] The results regarding the cosmetic effects of the shampoos are summarized in Table 9. Table 9: Shampoo / Results of reduced wet combing strength and improved softness on damaged hair after treatment with shampoo. All results compared to untreated hair wefts. Example / Compare Reduction in wet combing force [%] Improved softness [%] Example A3-a 50 25 Comparison test VA3*) 20 2 *) BELSIL ®< DM 5102 E (Dimethicone emulsion), available from Wacker Chemie AG

[0252] The shampoos according to the example A-3a The emulsion according to the invention shows a significantly higher reduction in wet combing force and a significantly improved softness (according to tensile test) compared to the shampoo according to the comparative test. VA3 with commercially available dimethicone emulsion. Example A3-b: Cosmetic composition - Shampoo

[0253] The following example represents a cosmetic composition containing the emulsion. B3. The active content of organopolysiloxanes in the cosmetic composition is 1.0%.

[0254] The composition of the shampoo is summarized in Table 10. Manufacturing instructions:

[0255] 0.30 parts guar hydroxypropyltrimonium chloride are dispersed in water. 41.50 parts sodium laureth sulfate are slowly stirred in, and the mixture is gradually heated to 75°C. During heating, 0.20 parts PEG-150 distearate are added at 50°C, followed by 0.50 parts glycol distearate at 65°C. The mixture is then cooled. Upon reaching 35°C, 0.90 parts phenoxyethanol, ethylhexylglycerin, and the emulsion (as per the example) are added, and the mixture is stirred for 5 minutes. Finally, 13.4 parts cocamidopropyl betaine are added, and the mixture is stirred for another 10 minutes.

[0256] Damaged hair, treated with the shampoo from example A3-b Hair that has been treated is softer, according to panel tests, than damaged, untreated hair. Table 10: A3-b Shampoo formulations (amount in parts by weight) Ingredients (INCI name) Example A3-b Aqua (Water VES) ad 100 Guar Hydroxypropyltrimonium Chloride 1)< 0,30 Sodium Laureth Sulfate 2)< 41,50 Glycol Distearate 3)< 0,50 PEG-120 Methyl Glucose Dioleate 4) 0,20 emulsion B3 from example 3 2,27 Cocamidopropyl Betaine 6)< 13,33 Phenoxyethanol, ethylhexylglycerol 7)< 0, 90 1) Guar Hydroxypropyltrimonium Chloride: N-Hance® < 3196, Ashland. 2) Sodium Laureth Sulfate: Genapol® < LRO 26.5%, Clariant GmbH. 3) Glycol Distearate: HALLSTAR® < EGDS, The Hallstar Company. 4) PEG-120 Methyl Glucose Dioleate: Glucamate™ < DOE 120 thickener, Lubrizol. 5) BELSIL® < DM 5102 E, available from Wacker Chemie AG. 6) Cocamidopropyl Betaine: Genagen® < CAB 30%, Clariant GmbH. 7) Phenoxyethanol, Ethylhexylglycerin: Euxyl PE 9010, Schülke & Mayr Example A3-c: Cosmetic composition - Shampoo

[0257] The following example represents a cosmetic composition containing the emulsion. B3. The active content of organopolysiloxanes in the cosmetic composition is 1.0%.

[0258] The composition of the shampoo is summarized in Table 11. Table 11: A3-c Shampoo formulation (amount in parts by weight) Ingredients (INCI name) Example A3-c Aqua (Water VES) ad 100 Polyquaternium-10 1)< 0, 10 Sodium Laureth Sulfate 2)< 52,80 PEG-150 Distearate 3)< 0,25 Cocamide MEA 4)< 1,00 emulsion B3 from example 3 2,27 Cocamidopropyl Betaine 5)< 10,06 Phenoxyethanol, ethylhexylglycerol 6)< 0,95 1) Polyquaternium-10: UCARE Polymer JR 400, Dow Chemical. 2) Sodium Laureth Sulfat: Genapol ®< LRO 26,5%, Clariant GmbH 3) PEG-150 Distearate: Eumulgin ®< EO 33, BASF AG 4) Cocamide MEA: Comperlan 100, BASF AG 5) Cocamidopropyl Betaine: Genagen ®< CAB 30%, Clariant GmbH 7) Phenoxyethanol, Ethylhexylglycerin: Euxyl PE 9010, Schülke & Mayr

[0259] Damaged hair, treated with the shampoo from example A3-c Hair that has been treated is softer, according to panel tests, than damaged, untreated hair. Beispiele A1-b und A2-b Rinse-Off Conditioner

[0260] The following examples represent cosmetic compositions. A1-b and A2-b containing the emulsions B-1b and B2. The active content of organopolysiloxanes in the cosmetic compositions is 2.0%.

[0261] The composition of the rinse-off conditioners is summarized in Table 12. Manufacturing instructions:

[0262] Water is placed in the container and heated to 75°C while stirring. 1.1 parts of hydroxyethylcellulose are added. When 65°C is reached, 0.5 parts of stearamidopropyl dimethylamine, 1.0 part of polysorbate 80, 3.0 parts of stearyl alcohol, 2.0 parts of cetyl alcohol, and 1.8 parts of behentrimonium chloride are added. The mixture is stirred until 75°C is reached and the ingredients are dissolved. The mixture is then cooled. During cooling, 0.2 parts of citric acid and 0.2 parts of tetrasodium EDTA are added. At 35°C, 0.9 parts of phenoxyethanol and ethylhexylglycerin are added. While continuing to stir, the emulsions from the examples are added. The composition is homogenized for 15 minutes while stirring. Tabelle 12: A1-b und A2-b Rinse-Off Conditioner Bestandteile (INCI-name) Example A1-b [Weight parts] Example A2-b [Weight parts] Water ad 100 ad 100 Hydroxyethylcellulose 1)< 1,1 1,1 Cetyl Alcohol 2)< 2, 0 2, 0 Polysorbate 80 3)< 1, 0 1, 0 Behentrimonium Chloride 4)< 1, 8 1, 8 Stearamidopropyl Dimethylamine 5)< 0,5 0,5 Stearyl Alcohol 6)< 3, 0 3, 0 Citric Acid 7)< 0,2 0,2 Tetrasodium EDTA 8)< 0,2 0,2 emulsion B1-b from example 1 5,71 emulsion B2 from example 2 4, 64 Phenoxyethanol, Ethylhexylglycerin 9)< 0, 9 0, 9 The raw materials listed in Table 12 are available under the following trade names: 1) Hydroxyethylcellulose: Natrosol 250 HR, Ashland 2) Cetyl alcohol: Cetyl Alcohol, Merck KGaA 3) Polysorbate 80: Tween™< 80, Croda GmbH 4) Behentrimonium Chloride: Genamin®< KDMP, Clariant GmbH 5) Stearamidopropyl Dimethylamine, Incromine™< SB, Croda GmbH 6) Stearyl alcohol: Stearyl Alcohol, Merck KGaA 7) Citric Acid: Citric Acid, Sigma 8) Tetrasodium EDTA: EDETA®< B Powder, BASF Corporation 9) Phenoxyethanol, Ethylhexylglycerin: Euxyl PE 9010, Schülke & Mayr

[0263] Damaged hair treated with rinse-off conditioners from the examples A1-b and A2-b Hair that has been treated is softer, according to panel tests, than damaged, untreated hair. Example A4 Cosmetic composition: Nourishing styling spray

[0264] The following example represents a cosmetic composition according to the invention. A4 containing the emulsion B1-a. For the production of the cosmetic composition A4 9.3 g of emulsion will be used. B1-a Diluted with 90.7 g of water. The active content of organopolysiloxanes in the cosmetic composition is 3.0%. Comparison example VA4 Cosmetic composition: Nourishing styling spray

[0265] The comparative example VA4 represents a non-inventive cosmetic composition containing the aqueous dispersion V2a pre-crosslinked organopolysiloxane. During the production of the cosmetic composition of the comparative test. VA4 The working method of the example was explained. A4 repeated, with the modification that the pre-crosslinked, non-inventive emulsions V2 8.7 g emulsion is used. V2 were diluted with 91.3 g of water. The active content of organopolysiloxanes in the non-inventive cosmetic composition VA4 It is 3.0%. Comparison of the conditioning styling sprays of the inventive example A4 with the comparison test VA4

[0266] To investigate the shaping properties of the conditioning styling sprays on hair, hair curls were produced as in the section "Curl Retention at high humidity", sprayed with 0.2 g of the respective spray and the curl retention was determined. Table 13: Nourishing styling spray / Curl retention results in high humidity after 7 hours. Example / Compare Curl Retention [%] Example A4 73 Comparison test VA4 30

[0267] As a result, curls styled with the styling spray according to the invention were obtained from example A4 The treated hair had a curl retention of 73% after 7 hours. The curls felt pleasantly soft and retained their shape even after combing. Combing the curls was effortless. (For hair curls treated with the spray from the non-inventive comparative example.) VA4 A curl retention of 30% was determined. The curl retention at high humidity is therefore significantly worse for these curls than for curls created with spray from the example according to the invention. A4 were treated.

Claims

1. Aqueous dispersions, preferably aqueous emulsions, comprising precrosslinked organopolysiloxanes that contain on average at least one structural unit of the general formula         SiRO2 / 2-Y-SiRO2 / 2     (I) and units of the formula         R2SiO2 / 2     (II) where Y denotes a radical of the formula         -R2-[NR3-R4]x-NR3-OC-[C(Z1)(H)]k1-[C(Z2)(H)]k2-CO-NR3 - [R4-NR3]a-R2-R2SiO1 / 2-[R2SiO2 / 2]b-R2SiO1 / 2-R2-[NR3-R4]a- NR3-OC-[C (Z2)(H)]k2-[C(Z1)(H)]k1-CO-NR3-[R4-NR3]x-R2-, R may be identical or different and denotes a monovalent SiC-bonded hydrocarbon radical that has 1 to 18 carbon atoms and may contain one or more heteroatoms from the group of N, P, S, O, and halogen, R2 may be identical or different and denotes a SiC-bonded, divalent linear or branched hydrocarbon radical having 3 to 18 carbon atoms, preferably an alkylene radical having 3 to 10 carbon atoms, R3 may be identical or different and denotes a hydrogen atom, an alkyl radical having 1 to 8 carbon atoms or an acyl radical, such as acetyl radical, and preferably is a hydrogen atom, R4 may be identical or different and denotes a divalent hydrocarbon radical having 1 to 6 carbon atoms, preferably an alkylene radical having 1 to 6 carbon atoms, k1 is 0, 1, 2 or 3, preferably 0, k2 is 0, 1, 2 or 3, preferably 0, x is 0, 1, 2, 3 or 4, preferably 0 or 1, a is 0, 1, 2, 3 or 4, preferably 0 or 1, b is 0 or an integer from 1 to 500, preferably 20 to 350, Z1 denotes -OH, H or -NHR3, Z2 denotes -OH, H or -NHR3.

2. Aqueous dispersions according to Claim 1, characterized in that the precrosslinked organopolysiloxanes contain siloxane units of the formula         R3-d(OR1)dSiO1 / 2     (III) where R is as defined in Claim 1, R1 may be identical or different and denotes a hydrogen atom or an alkyl radical that has 1 to 18 carbon atoms and may be interrupted by one or more separate oxygen atoms, and d is 0 or 1.

3. Aqueous dispersions according to Claim 1 or 2, characterized in that Y is a radical of the formula         -R2-[NH-CH2CH2]x-NH-OC-CO-NH-R2 -R2SiO1 / 2-[R2SiO2 / 2]b-R2SiO1 / 2- R2-NH-OC-CO-NH-[CH2CH2-NH]x-R2- where R is as defined in Claim 1, x is 0 or 1, b is 0 or an integer from 1 to 500, preferably 20 to 350, and R2 is a radical of the formula -(CH2)3- or -CH2-CH(CH3)-CH2-.

4. Process for producing aqueous dispersions, preferably aqueous emulsions, of precrosslinked organopolysiloxanes, wherein aqueous dispersions, preferably aqueous emulsions, of aminoorganopolysiloxanes (1) of the formula         (R1O)dAeR3-d-eSiO(SiARO)p(SiR2O)qSiR3-d-eAe(OR1)d     (IV) where A is an amino radical of the general formula         -R2-[NR3-R4-]xNR32, R may be identical or different and denotes a monovalent SiC-bonded hydrocarbon radical that has 1 to 18 carbon atoms and may contain one or more heteroatoms from the group of N, P, S, O, and halogen, R1 may be identical or different and denotes a hydrogen atom or an alkyl radical that has 1 to 18 carbon atoms and may be interrupted by one or more separate oxygen atoms, R2 may be identical or different and denotes a SiC-bonded, divalent linear or branched hydrocarbon radical having 3 to 18 carbon atoms, preferably an alkylene radical having 3 to 10 carbon atoms, R3 may be identical or different and denotes a hydrogen atom, an alkyl radical having 1 to 8 carbon atoms or an acyl radical, such as acetyl radical, and preferably is a hydrogen atom, R4 may be identical or different and denotes a divalent hydrocarbon radical having 1 to 6 carbon atoms, preferably an alkylene radical having 1 to 6 carbon atoms, d is 0 or 1, e is 0 or 1, p is an integer that is at least 1 and at most 1000, q is 0 or an integer from 1 to 2000, and x is 0, 1, 2, 3 or 4, preferably 0 or 1, are reacted with reactive esters (2) of the formula         R5-O2C-[C(Z1)(H)]k1-[C(Z2)(H)]k2-CO-NR3 - [R4-NR3]a-R2-R2SiO1 / 2-[R2SiO2 / 2]b-R2SiO1 / 2-R2-[NR3-     (V) R4]a-NR3-OC-[C(Z2)(H)]k2-[C(Z1)(H)]k1-CO2-R5 where R, R2, R3 and R4 are as defined above, R5 may be identical or different and denotes an O-bonded, saturated or unsaturated, linear or branched, monovalent hydrocarbon radical that has 1-20 carbon atoms per radical and may contain one or more heteroatoms from the group of N, P, S, O and halogen, k1 is 0, 1, 2 or 3, preferably 0, k2 is 0, 1, 2 or 3, preferably 0, a is 0, 1, 2, 3 or 4, preferably 0 or 1, b is 0 or an integer from 1 to 500, preferably 20 to 350, Z1 denotes -OH, H or -NHR3, and Z2 denotes -OH, H or -NHR35. Process according to Claim 4, characterized in that A is an amino radical of the formula         -R2-[NH-CH2CH2-]xNH2 where x is 0 or 1 and R2 is a radical of the formula -(CH2)3- or -CH2-CH(CH3)-CH2-.

6. Process according to Claim 4 or 5, characterized in that the reactive esters (2) are oxalamido-methyl-ester-terminated organopolysiloxanes and oxalamido-ethylester-terminated organopolysiloxanes.

7. Precrosslinked organopolysiloxanes that contain on average at least one structural unit, preferably at least two structural units, more preferably at least three structural units, of the general formula         SiRO2 / 2-Y-SiRO2 / 2     (I) and units of the formula         R2SiO2 / 2     (II) where Y denotes a radical of the formula         -R2-[NR3-R4]x-NR3-OC-[C(Z1)(H)]k1-[C(Z2)(H)]k2-CO-NR3 - [R4-NR3]a-R2-R2SiO1 / 2-[R2SiO2 / 2]b-R2SiO1 / 2-R2-[NR3-R4]a- NR3-OC-[C(Z2)(H)]k2-[C(Z1)(H)]k1-CO-NR3-[R4-NR3]x-R2-, R, R2, R3, R4, k1, k2, x, a, b, Z1 and Z2 are as defined in Claim 1.

8. Precrosslinked organopolysiloxanes according to Claim 7, characterized in that they contain siloxane units of the formula         R3-d(OR1)dSiO1 / 2     (III) where R is as defined in Claim 1 and d and R1 are as defined in Claim 2.

9. Process for producing precrosslinked organopolysiloxanes, characterized in that aminoorganopolysiloxanes of the formula         (R1O)dAeR3-d-eSiO(SiARO)p(SiR2O)qSiR3-d-eAe(OR1)d     (IV) are reacted with reactive esters of the formula         R5-O2C-[C(Z1)(H)]k1-[C(Z2)(H)]k2-CO-NR3         - [R4-NR3]a-R2-R2SiO1 / 2-[R2SiO2 / 2]b-R2SiO1 / 2-R2-[NR3-     (V)         R4]a-NR3-OC-[C(Z2)(H)]k2-[C(Z1)(H)]k1-CO2-R5 where A, R, R1, R2, R3, R4, R5, d, e, p, q, k1, k2, a, b, Z1 and Z2 are as defined in Claim 4, and the resulting precrosslinked organopolysiloxanes are optionally subsequently emulsified in water.

10. Cosmetic compositions comprising aqueous dispersions, preferably aqueous emulsions, of precrosslinked organopolysiloxanes according to Claim 1, 2 or 3 or produced according to Claim 4, 5 or 6, or precrosslinked organopolysiloxanes according to Claim 7 or 8 or produced according to Claim 9.

11. Cosmetic compositions according to Claim 10, characterized in that they comprise conditioning agents.

12. Use of the cosmetic compositions according to Claim 10 or 11 for treating keratin fibers, preferably for cleansing, caring for or shaping keratin fibers.

13. Use of the cosmetic compositions according to Claim 10 or 11 for conditioning keratin fibers, for the purpose in particular of making keratin fibers easier to comb.

14. Use according to Claim 12 or 13, characterized in that the keratin fibers are hair.

15. Process for treating keratin-containing fibers, preferably hair, by applying the cosmetic compositions according to Claim 10 or 11 to the keratin fibers, preferably hair, and then optionally rinsing with water.