Aqueous dispersion of pre-crosslinked organopolysiloxane

Abstract

In the present invention, the compound represented by the following general formula SiRO 2 / 2 -Y-SiRO 2 / 2 On average at least one structural unit of (I) and the following formula RSiO 2 / 2 Novel aqueous dispersions of pre-crosslinked organopolysiloxanes containing units of the formula (II) are described, wherein Y is -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 -R2SiO 1 / 2 -[R2SiO 2 / 2 ] b -R2SiO 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 -, R may be the same or different and represent a monovalent SiC-bonded hydrocarbon radical having 1 to 18 carbon atoms which may contain one or more heteroatoms from the group of N, P, S, O, and halogen, R 2 means a SiC-bonded divalent linear or branched hydrocarbon radical having 3 to 18 carbon atoms, R 3 is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an acyl group, and R 4means a divalent hydrocarbon group having 1 to 6 carbon atoms, k1 is 0, 1, 2 or 3, k2 is 0, 1, 2 or 3, x is 0, 1, 2, 3 or 4, a is 0, 1, 2, 3 or 4, b is 0 or an integer of 1 to 500, and Z 1 is -OH, H or -NHR 3 means Z 2 is -OH, -H or -NHR 3 means.

Description

[Technical Field]

[0001] The present invention relates to a cosmetic composition comprising an aqueous dispersion of a pre-crosslinked organopolysiloxane, a pre-crosslinked organopolysiloxane, and an aqueous dispersion of the pre-crosslinked organopolysiloxane. The present invention further relates to a process for producing the pre-crosslinked organopolysiloxane and its aqueous dispersion. The present invention further relates to the use of the cosmetic composition. [Background technology]

[0002] Organopolysiloxanes are used in cosmetic compositions, such as hair care products, for their conditioning properties, such as improved softness and smoothness, reduced combing force, gloss properties, improved perceived color, color protection properties, reduced instances of static electricity, protection properties related to thermal stress on hair, or hydrophobicity.

[0003] An overview of selected organopolysiloxanes for the care of keratinous substances such as hair can be found in MDBerthiaume, Society of Cosmetic Chemists (ed.), monograph, Silicones in Hair Care, 1997, and in J. Sejpka, Silicones in Haircare Products, SOEFW-Journal, Vol. 118, No. 17, 1992, pp. 1065-1070.

[0004] In daily life, hair is exposed to numerous external influences that cause damage to the hair surface and therefore impair its 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 treatment, UV radiation, or heat. Accompanying surface damage to hair is the destruction and partial removal of the lipid layer covering the cuticle, which is the cause of the highly hydrophobic quality of undamaged natural hair (RALodge, 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). Since the effective hair surface after the destruction of the surface lipid layer is a hydrophilic amino acid-based protein matrix, damaged hair is significantly more hydrophilic than undamaged hair.

[0005] Modified siloxanes using oxalamide ester-terminated organopolysiloxanes are known. Those described in WO2019 / 114953A1 are linear copolymers of oxalamide ester-terminated organopolysiloxanes and amino-terminated polyethers. These exhibit significantly increased hydrophilicity compared to purely amino-functionalized organopolysiloxanes. However, their linear structure means they lack elasticity.

[0006] US7501184B2 describes copolymers obtained by reacting linear organopolysiloxanes terminated with oxalamide ester groups with organic diamines. High-viscosity to solid copolymers are obtained and are used in adhesives, particularly as hot-melt adhesives. These high-viscosity products are not stably emulsifiable and therefore cannot be used for treating fibrous substrates such as hair. Furthermore, their linear structure means that they do not possess elastic properties.

[0007] US7223385B2, US7485289B2, US7220408B2, and US7504094B2 describe cosmetic compositions for treating hair, comprising special aminosilicones and conditioning or thickening agents. The aminosilicones are dimethylpolysiloxanes having terminal alkoxy / hydroxyl groups and uncrosslinked aminoethylaminopropylalkoxysiloxane units or aminoethylaminopropylmethylsiloxane units.

[0008] WO2020 / 239229A1 describes an aqueous dispersion of pre-crosslinked organopolysiloxanes that can be used in cosmetic compositions and preferably form an elastomer film after the removal of water. Cosmetic formulations for hair applications containing pre-crosslinked organopolysiloxanes have been found to exhibit specific care effects. Despite the property of forming an elastomer film, only a limited effect on the shaping of hair fibers is observed.

[0009] US5039738A discloses a process for producing a modified aminoorganosiloxane by reacting an aminoorganosiloxane in an aqueous emulsion with a dialkyl oxalate, a dialkyl pyrocarbonate, or a mixture thereof. Fiber materials treated with the described emulsion were found to exhibit reduced yellowing.

[0010] WO2015 / 024079A1 describes a cosmetic composition comprising an aminoorganopolysiloxane, a cationic surfactant, and a dialkyl ester of a dicarboxylic acid of the formula R'-O-CO-R-CO-O-R', where R' is a C8-C30 group.

[0011] According to WO2004 / 039930A2, fibers treated with a composition consisting of polycarboxylic acid and aminoorganosiloxane exhibit improved resistance to curling and creasing.

[0012] A crosslinkable composition comprising an aminoorganopolysiloxane and a crosslinking agent component which is an alkoxysilane or siloxane having at least one carboxylic acid anhydride group is described in US Patent No. 5399652A. [Prior art documents] [Patent Documents]

[0013] [Patent Document 1] International Publication No. 2019 / 114953 [Patent Document 2] U.S. Patent No. 7501184 [Patent Document 3] U.S. Patent No. 7223385 [Patent Document 4] U.S. Patent No. 7485289 [Patent Document 5] U.S. Patent No. 7220408 [Patent Document 6] U.S. Patent No. 7504094 [Patent Document 7] International Publication No. 2020 / 239229 [Patent Document 8] U.S. Patent No. 5039738 [Patent Document 9] International Publication No. 2015 / 024079 [Patent Document 10] International Publication No. 2004 / 039930 [Patent Document 11] U.S. Patent No. 5,399,652 [Non-patent literature]

[0014] [Non-Patent Document 1] MDBerthiaume, Society of Cosmetic Chemists (ed.), monograph, Silicones in Hair Care, 1997 [Non-Patent Document 2] SOFW-Journal, Vol. 118, No. 17, 1992, pp. 1065-1070, J. Sejpka, Silicones in Haircare Products [Non-Patent Document 3] RALodge, B.Bhusan, Wetting Properties of Human hair by Means of Dynamic Contact Angle Measurement, Journal of Applied Polymer Science, Volume 102, 5255-5265, 2006, Wiley [Overview of the project] [Problems that the invention aims to solve]

[0015] The objective was to provide a pre-crosslinked organopolysiloxane, particularly an aqueous dispersion of a pre-crosslinked organopolysiloxane, which preferably forms an elastomer film upon removal of water and can be used in cosmetic compositions. A further objective was to provide a cosmetic composition for treating keratin fibers such as hair, preferably for washing and caring thereof, which can be used to shape and condition keratin fibers such as hair, and in particular to provide easier combability. [Means for solving the problem]

[0016] The above objective is achieved by the present invention.

[0017] The present invention relates to an aqueous dispersion, preferably an aqueous emulsion, containing a pre-crosslinked organopolysiloxane, The pre-crosslinked organopolysiloxane has, on average, at least one structural unit, preferably at least two structural units, and more preferably at least three structural units of the following general formula. SiRO 2 / 2 -Y-SiRO 2 / 2 (I) and the units of the following formulas R2SiO 2 / 2 (II) [In the formula, Y represents a group of the following 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 -R2SiO 1 / 2 -[R2SiO 2 / 2 b -R2SiO 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 - R may be the same or different and represents a monovalent SiC-bonded hydrocarbon group having 1 to 18 carbon atoms, which may contain one or more heteroatoms from the group consisting of N, P, S, O and halogen, R 2 may be the same or different and represents a SiC-bonded divalent linear or branched hydrocarbon group having 3 to 18 carbon atoms, preferably an alkylene group having 3 to 10 carbon atoms, R 3 may be the same or different and represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an acyl group such as an acetyl group, preferably a hydrogen atom, R 4 ​​​​​These may be the same or different, and represent a divalent hydrocarbon group having 1 to 6 carbon atoms, preferably an alkylene group 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 an integer between 0 and 500, preferably between 20 and 350. Z 1 -OH, -H, or -NHR 3 This represents, Z 2 -OH, -H, or -NHR 3 [This represents...] The present invention provides an aqueous dispersion, preferably an aqueous emulsion, containing the above.

[0018] The present invention relates to a pre-crosslinked organopolysiloxane, Furthermore, on average, at least one structural unit, preferably at least two structural units, and more preferably at least three structural units, are found in the following general formula. SiRO 2 / 2 -Y-SiRO 2 / 2 (I) and the units of the following formulas R2SiO 2 / 2 (II) [In the formula, Y is the basis of the following equation, -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 -R2SiO 1 / 2 -[R2SiO 2 / 2b -R2SiO 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 - R, R 2 , R 3 , R 4 , k1, k2, x, a, b, Z 1 , and Z 2 are as defined above.]] pre-crosslinked organopolysiloxane comprising is provided.

[0019] The present invention further relates to a process for producing an aqueous dispersion of a pre-crosslinked organopolysiloxane, wherein an aqueous dispersion, preferably an aqueous emulsion, of aminoorganopolysiloxane (1) of the following formula: (R 1 O) d A e R 3-d-e SiO(SiARO) p (SiR2O) q SiR 3-d-e A e (OR 1 ) d (IV) wherein, A is an amino group of the following general formula: -R 2 -[NR 3 -R 4 -] x NR 3 2 R may be the same or different and represents a monovalent SiC-bonded hydrocarbon group having 1 to 18 carbon atoms, which may contain one or more heteroatoms selected from the group consisting of N, P, S, O and halogen, R​​​1 This may be the same or different, and represents an alkyl group having a hydrogen atom or 1 to 18 carbon atoms, which may be interposed by one or more distinct oxygen atoms. R 2 These may be the same or different, and represent a SiC-bonded divalent linear or branched hydrocarbon group having 3 to 18 carbon atoms, preferably an alkylene group having 3 to 10 carbon atoms. R 3 These may be the same or different, and represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an acyl group such as an acetyl group, preferably representing a hydrogen atom. R 4 These may be the same or different, and represent a divalent hydrocarbon group having 1 to 6 carbon atoms, preferably an alkylene group having 1 to 6 carbon atoms. d is either 0 or 1. e is either 0 or 1. p is an integer at least 1, preferably at least 2, more preferably at least 3, and at most 1000, preferably at most 10. q is an integer between 0 and 2000, preferably between 50 and 1000. x is 0, 1, 2, 3, or 4, preferably 0 or 1. We provide a manufacturing process that involves reacting with the reactive ester (2) of the following formula. R 5 -O2C-[C(Z 1 )(H)] k1 -[C(Z 2 )(H)] k2 -CO-NR 3 -[R 4 -NR 3 ] a -R 2 -R2SiO 1 / 2 -[R2SiO 2 / 2 ] b -R2SiO 1 / 2 -R 2 -[NR 3 -R 4 ] a -NR 3 -OC-[C(Z2 )(H)] k2 -[C(Z 1 )(H)] k1 -CO2-R 5 (V) [In the formula, R, R 2 , R 3 , and R 4 As defined above, R 5 This represents an oxygen-bonded saturated or unsaturated, linear or branched monovalent hydrocarbon group, which may be identical or different, have 1 to 20 carbon atoms per group, and may contain one or more heteroatoms from the group consisting of N, P, S, O and halogens. 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 an integer between 0 and 500, preferably between 20 and 350. Z 1 -OH, -H, or -NHR 3 This represents, Z 2 -OH, -H, or -NHR 3 [This represents...]

[0020] The present invention further relates to a process for producing pre-crosslinked organopolysiloxanes, The aminoorganopolysiloxane (1) in the following formula (R 1 O) d A e R 3-d-e SiO(SiARO) p (SiR2O) q SiR 3-d-e A e (OR 1 ) d (IV) React with the reactive ester (2) of the following formula, R 5 -O2C-[C(Z 1 )(H)] k1 -[C(Z 2 )(H)] k2-CO-NR 3 -[R 4 -NR 3 ] a -R 2 -R2SiO 1 / 2 -[R2SiO 2 / 2 ] b -R2SiO 1 / 2 -R 2 -[NR 3 -R 4 ] a -NR 3 -OC-[C(Z 2 )(H)] k2 -[C(Z 1 )(H)] k1 -CO2-R 5 (V) [In the formula, 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 This is as defined above. The present invention provides a manufacturing process characterized by optionally subsequently emulsifying the obtained pre-crosslinked organopolysiloxane in water.

[0021] In the process of the present invention, the aminoorganopolysiloxane (1) of formula (IV) used is preferably e = 0 and therefore contains only pendant amino group A, and in reaction with the reactive ester (2), forms crosslinks according to the structural units of formula (I).

[0022] When e is 0, the pre-crosslinked organopolysiloxane of the present invention preferably includes not only the structural unit of formula (I) and the siloxane unit of formula (II), but also the siloxane unit of the following formula. R 3-d (OR 1 ) d SiO 1 / 2 (III) [In the formula, R, R 1 And d are as defined above.

[0023] However, it is also possible to use an aminoorganopolysiloxane (1) of formula (IV) which also contains a terminal amino group A, and therefore e is 1.

[0024] It is also possible to use a mixture of aminoorganopolysiloxanes (1) of formula (IV) (where e is 0 and e is 1).

[0025] In the reaction with the reactive ester (2), crosslinking between two terminal amino groups (formula (VI)) or between a terminal and a pendant amino group (formula (VII)) may be further formed in this case.

[0026] Furthermore, in addition to aminoorganopolysiloxane (1), aminoorganopolysiloxane (1a) containing only the terminal amino group of the following general formula can be used. (R 1 O) f AR 2-f SiO(SiR2O) n SiR 2-f A(OR 1 ) f (IVa) [In the formula, A, R, and R 1 As defined above, f is either 0 or 1. n is an integer between 1 and 1000, preferably between 50 and 1000.

[0027] As a result, in addition to the structural unit of formula (I), the pre-crosslinked organopolysiloxane of the present invention has the following formula NutR2O 1 / 2 -Y-SiR2O 1 / 2 (VI) or SiRO 2 / 2 -Y-SiR2O 1 / 2 (VII) Structural units Or it may further include a mixture of (VI) and (VII). [R and Y are as defined above.]

[0028] The pre-crosslinked organopolysiloxane of the present invention preferably comprises a siloxane unit of formula (III) in which d is 0 or 1, preferably 1.

[0029] The pendant and optionally terminal amino group A in the aminoorganopolysiloxane (1) or optionally in the aminoorganopolysiloxane (1a) used in the present invention can also optionally react with the reactive ester (2) without forming a crosslink, and thus the pre-crosslinked organopolysiloxane is given by the following formula 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 -R2SiO 1 / 2 -[R2SiO 2 / 2 ] b -R2SiO 1 / 2 -R 2 -[NR 3 -R 4 ] a -NR 3 -OC-[C(Z 2 )(H)] k2 -[C(Z 1 )(H)] k1 -CO2-R 5 (VIIIa) and / or NutR2O 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 -[R4 -NR 3 ] a -R 2 -R2SiO 1 / 2 -[R2SiO 2 / 2 ] b -R2SiO 1 / 2 -R 2 -[NR 3 -R 4 ] a -NR 3 -OC-[C(Z 2 )(H)] k2 -[C(Z 1 )(H)] k1 -CO2-R 5 (VIIIb) [In the formula, R, R 2 , R 3 , R 4 , R 5 k1, k2, x, a, b, Z 1 , and Z 2 This is as defined above. It can further include structural units.

[0030] In relation to the present invention, formula (IV) is p-unit-(SiARO)- and q-unit-(SiR 2 It should be understood that this means that O)- can be distributed in any manner, for example, as blocks or statistically within the aminoorganopolysiloxane molecule.

[0031] Although not represented by formulas (IV) and (IVa), respectively, the aminoorganopolysiloxane (1) and optionally used aminoorganopolysiloxane (1a) used in the present invention are also represented by the following formula RSiO 3 / 2 , (OR 1 )SiO 3 / 2 and SiO 4 / 2 (IXa-c) [In the formula, R and R 1 This is as defined above. The pre-crosslinked organopolysiloxane of the present invention may also contain siloxane units of formula (IXa-c), which are selected from the groups of the pre-crosslinked organopolysiloxane of the present invention. [Modes for carrying out the invention]

[0032] Preferably, R is a monovalent saturated or unsaturated hydrocarbon group having 1 to 18 carbon atoms.

[0033] Examples of hydrocarbon groups R include alkyl groups, e.g., methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl group; hexyl group, e.g., n-hexyl group; heptyl group, e.g., n-heptyl group; octyl group, e.g., n-octyl group and isooctyl group, e.g., 2,2,4-trimethylpentyl group; nonyl group, e.g., n-nonyl group; decyl group, e.g., n-decyl group; dodecyl group, e.g., n-dodecyl group; octadecyl group, Examples include n-octadecyl groups; 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-, and p-tolyl groups; xylyl and ethylphenyl groups; and aralkyl groups, such as benzyl and α- and β-phenylethyl groups.

[0034] Preferred groups for group R are methyl, ethyl, octyl, and phenyl groups, and more preferably methyl and ethyl groups.

[0035] Examples of substituted groups R include haloalkyl groups, such as 3,3,3-trifluoro-n-propyl, 2,2,2,2',2',2'-hexafluoroisopropyl, heptafluoroisopropyl, and haloaryl groups, such as o-, m-, and p-chlorophenyl groups.

[0036] Further examples of the substituted group R include polyalkylene oxy groups, such as polyethylene oxy groups, polypropylene oxy groups, or polyethylene oxy / polypropylene oxy groups.

[0037] base R 1 Examples of R include the alkyl groups listed above, and also methoxyethyl, ethoxyethyl, and hexoxyethyl groups, preferably the group R 1 This is a hydrogen atom, a methyl group, or an ethyl group.

[0038] Preferably, R 5 is C 1~20 It is a hydrocarbon group, which may be interposed by one or more oxygen atoms.

[0039] An example of base R is base R 5 This also applies.

[0040] Preferably, R 5 is C 1~4 Alkyl groups, such as methyl or ethyl groups.

[0041] An example of base A is, -(CH2)3NH2 -(CH2)3-NH-(CH2)2-NH2 -CH2CH(CH3)CH2-NH-(CH2)2-NH2 -(CH2)3-NH(cyclohexyl) -(CH2)3-NHCH3 -(CH2)3-N(CH3)2 -(CH2)3-NHCH2CH3 -(CH2)3-N(CH2CH3)2 -(CH2)4-NH2 -CH2CH(CH3)CH2-NH2 -(CH2)3-NH-(CH2)2-NHCH3 -(CH2)3-NH-(CH2)2-N(CH3)2 -(CH2)3-NH-(CH2)2-NHCH2CH3 -(CH2)3-NH-(CH2)2-N(CH2CH3)2 -(CH2)3[-NH-CH2CH2]2-NH2 and its partially or completely acetylated forms, for example -(CH2)3-NH(acetyl) (CH2)3-NH-(CH2)2-NH (acetyl), and It is -(CH2)3-N(acetyl)-(CH2)2-NH(acetyl).

[0042] A preferred example of base A is: -(CH2)3NH2 -(CH2)3-NH-(CH2)2-NH2 -CH2CH(CH3)CH2-NH-(CH2)2-NH2 It is -(CH2)3-NHCH3.

[0043] Preferably, A is an amino group of the following formula. -R 2 -[NH-CH2CH2-] x NH2 [In the formula, x is either 0 or 1, R 2 This is the group of the formula -(CH2)3- or -CH2-CH(CH3)-CH2-.

[0044] A particularly preferred example of base A is: -(CH2)3NH2 -(CH2)3-NH-(CH2)2-NH2 and It is -CH2CH(CH3)CH2-NH-(CH2)2-NH2.

[0045] Further examples of aminoorganopolysiloxanes (1) include commercially available functionalized siloxanes, such as amine oils, such as amine oils having a 3-(2-aminoethyl)aminopropyl functional group, and also glycol oils, phenyl oils, or phenylmethyl oils containing an amino group.

[0046] In the production of the dispersion of the present invention, it is possible to use one type of aminoorganopolysiloxane (1) or different types of aminoorganopolysiloxanes (1).

[0047] The aminoorganopolysiloxane (1) used in the production of the dispersion of the present invention preferably has a viscosity of 1 mPa.s to 5,000,000 mPa.s at 25°C, more preferably 50 mPa.s to 1,000,000 mPa.s at 25°C, and particularly preferably 100 mPa.s to 5,000,000 mPa.s at 25°C.

[0048] The aminoorganopolysiloxane (1) used in the production of the dispersion of the present invention can be produced, for example, as described in US7129369B2.

[0049] The dispersion of the present invention preferably comprises the pre-crosslinked organopolysiloxane of the present invention, an emulsifier (3), and water (4).

[0050] The pre-crosslinked organopolysiloxane dispersion of the present invention can optionally be prepared using further substances that do not directly participate in the reaction.

[0051] Upon drying (without the addition of a catalyst or change in pH), the dispersion of the present invention forms a silicone network, preferably an elastic silicone network. The dispersion of the present invention preferably forms an elastomer film after the removal of water.

[0052] In the process of the present invention, in the reaction of the aminoorganopolysiloxane (1) and optionally (1a) with a reactive ester (2) according to the present invention, a metal-containing catalyst is preferably not used.

[0053] Therefore, the dispersion of the present invention preferably does not contain a catalyst.

[0054] In the production of the pre-crosslinked organopolysiloxane of the present invention, an aminoorganopolysiloxane (1) and a reactive ester (2) are used, and these components react with each other preferably at room temperature. No additional metal-containing catalyst is required to assist this reaction, and therefore, preferably, transition metals and their compounds from lower group VIII of the periodic table, as well as metals and their compounds from main groups III, IV, and V of the periodic table, are not used. In this definition, the elements C, Si, N, and P are not considered metals.

[0055] Furthermore, the reaction preferably proceeds in a neutral range, i.e., a pH range of about 4–8 obtained by the components themselves. High reactivity also means that a specifically controlled chemical reaction is not required, and preferably no heating is necessary.

[0056] In the production of the dispersion of the present invention, it is possible to use one type of aminoorganopolysiloxane (2) as a crosslinking agent or different types of aminoorganopolysiloxanes (2) as crosslinking agents.

[0057] The preferred ester (2) used is an oxalamide ester-terminated organopolysiloxane of the following formula. R 5 -O2C-CO-NH-R 2 -R2SiO 1 / 2 -[R2SiO 2 / 2 ] b -R2SiO 1 / 2 -R 2 -NH-OC-CO2-R 5 [In the formula, R is as defined above, R 2 is a group of the formula -(CH2)3- or -CH2-CH(CH3)-CH2-, R 5 This is as defined above, preferably a C1-4 alkyl group, particularly a methyl group or an ethyl group. b is an integer between 0 and 500, preferably between 20 and 350.

[0058] Therefore, Y is preferably the base of the following equation. -R 2 -[NH-CH2CH2] x -NH-OC-CO-NH-R 2 -R2SiO 1 / 2 -[R2SiO 2 / 2 ] b -R2SiO 1 / 2 -R2-NH-OC-CO-NH-[CH2CH2-NH] x -R 2 - [In the formula, x is either 0 or 1, b and R are as defined above. R2 is a group of the formula -(CH2)3- or -CH2-CH(CH3)-CH2-.

[0059] Depending on the use of a crosslinking agent (2) or a linear, branched, or resinous aminoorganopolysiloxane (1), the pre-crosslinked organopolysiloxane may have a branched, or even more highly branched or highly crosslinked structure together with the linear fraction.

[0060] In the process of the present invention, the properties and amounts of the aminoorganopolysiloxane and ester are selected so that the organopolysiloxane in the resulting dispersion is pre-crosslinked.

[0061] The preferred aminoorganopolysiloxane (1) used contains, on average, at least one primary amino functional group in the terminal amino group A, thus giving the pre-crosslinked organopolysiloxane of the present invention. Furthermore, it is also possible to use an aminoorganopolysiloxane (1a) containing only terminal amino groups A having primary amino functional groups.

[0062] When using aminoorganopolysiloxane (1a), it is preferable to use it in an amount of 10 to 300 parts by weight per 100 parts by weight of aminoorganopolysiloxane (1).

[0063] Furthermore, the pre-crosslinked organopolysiloxane of the present invention can also be obtained by using a mixture of aminoorganopolysiloxane (1) and non-functional organopolysiloxane (1b).

[0064] Here, the non-functional organopolysiloxane (1b) is an organopolysiloxane that does not have an amino group A, preferably a linear organopolysiloxane with the following general formula. R 7 u R 6 3-u SiO[R 6 2SiO] v SiR 6 3-u R 7 u (X) [In the formula, R 6 This is as defined for R, R 7 R 6 It is as defined, or it is an HO- group. u is either 0 or 1, v is an integer between 0 and 2000.

[0065] Preferably, R 6 is C 1~18 hydrocarbon group, preferably C 1~18 It is an alkyl group.

[0066] Examples of non-functional organopolysiloxanes (1b) are dialkylpolysiloxanes, preferably dimethylpolysiloxanes.

[0067] When using non-functional organopolysiloxane (1b), it is preferable to use it in an amount of 100 to 800 parts by weight per 100 parts by weight of aminoorganopolysiloxane (1).

[0068] The degree of crosslinking here is determined by the use of the -OR in the reactive ester (2) to the amino group A in the aminoorganopolysiloxane (1). 5 It depends on the ratio of their equivalents.

[0069] To produce the dispersion of the present invention, which consists of an aminoorganopolysiloxane (1) and a reactive ester (2), the ester (2) preferably contains 0.1 to 10 equivalents of -OR per equivalent of amino group A in the aminoorganopolysiloxane (1). 5 , more preferably 0.2 to 5 equivalents of -OR 5 Particularly preferably 0.3 to 3 equivalents of -OR 5 It is used in that quantity.

[0070] The pre-crosslinked organopolysiloxane dispersion of the present invention is produced by vigorously mixing an aminoorganopolysiloxane (1), an ester (2), an emulsifier (3), and water (4).

[0071] Manufacturing can be carried out in batches or continuously.

[0072] The method for mixing the components used to produce the dispersion of the present invention is not particularly important and can be carried out in different orders.

[0073] For example, components (1) and (2) can be pre-mixed with each other, then an emulsifier can be added, followed by the incorporation of water (4). Another possibility is to continuously meter and supply components (1) to (4) to an emulsifier. In special cases, for example, due to the viscosity or reactivity of the aminoorganopolysiloxane (1) and optionally (1a) and optionally non-functional organopolysiloxane (1b) used, it may be advantageous to mix ester (2) with the aminoorganopolysiloxane and then incorporate different aminoorganopolysiloxanes or non-functional organopolysiloxanes, or vice versa, which may achieve more favorable rheological properties for processing the components.

[0074] Furthermore, it is possible to introduce ester (2) as a crosslinking agent into the final emulsion of aminoorganopolysiloxane (1) to achieve the desired reaction and crosslinking of the aminoorganopolysiloxane in the emulsion. To obtain a VOC-free product that does not contain volatile organic compounds, by-product alcohol R 5 OH(R 5 (as defined above) can be completely or partially removed by appropriate known means such as distillation, membrane methods, or other separation methods.

[0075] In the production of the dispersion of the present invention, water (4) is used in all cases in an amount preferably 1% to 99% by weight, more preferably 25% to 95% by weight, based on the total weight of all components of the dispersion.

[0076] The aqueous dispersion of the pre-crosslinked organopolysiloxane of the present invention is used as an oil-in-water system.

[0077] As emulsifiers (3) for producing aqueous dispersions of pre-crosslinked organopolysiloxanes, all anionic, nonionic, cationic, or amphoteric emulsifiers known to date can be used both individually and in mixtures of different emulsifiers, and it has also been possible for some time to produce aqueous dispersions of organopolysiloxanes, or more specifically, aqueous emulsions.

[0078] Examples of anionic emulsifiers are as follows:

[0079] 1. Alkyl sulfates, particularly those having a chain length of 8 to 18 carbon atoms, and alkyl and alkaryl ether sulfates having 8 to 18 carbon atoms and 1 to 40 ethylene oxide (EO) units and / or propylene oxide (PO) units in the hydrophobic group.

[0080] 2. Sulfonates, particularly alkyl sulfonates having 8 to 18 carbon atoms, alkylaryl sulfonates having 8 to 18 carbon atoms, taurids, esters and monoesters of sulfosuccinic acid with monohydric alcohols or alkylphenols having 4 to 15 carbon atoms (these alcohols or alkylphenols may also be optionally ethoxylated with 1 to 40 EO units).

[0081] 3. Alkali metal and ammonium salts of carboxylic acids having 8 to 20 carbon atoms in an alkyl, aryl, alkaryl, or aralkyl group.

[0082] 4. Partial esters of phosphoric acid and alkali metal salts and ammonium salts thereof, in particular alkyl and alkaryl phosphates having 8 to 20 carbon atoms in the organic group, and alkyl ether phosphates and alkaryl ether phosphates having 8 to 20 carbon atoms and 1 to 40 EO units in the alkyl or alkaryl group.

[0083] Examples of nonionic emulsifiers are as follows:

[0084] 5. Polyvinyl alcohol having 5% to 50%, preferably 8% to 20%, of vinyl acetate units and a degree of polymerization of 500 to 3000.

[0085] 6. Alkyl polyglycol ethers, preferably those having 3 to 40 EO units and 8 to 20 alkyl groups.

[0086] 7. Alkylaryl polyglycol ethers, preferably those having 5 to 40 EO units and 8 to 20 carbon atoms in the alkyl and aryl groups.

[0087] 8. Ethylene oxide / propylene oxide (EO / PO) block copolymer, preferably having 8 to 40 EO units or PO units.

[0088] 9. Addition products of alkylamines having an alkyl group with 8 to 22 carbon atoms with ethylene oxide or propylene oxide.

[0089] 10. Fatty acids having 6 to 24 carbon atoms.

[0090] 11. General formula R”-OZ o The alkyl polyglycoside (R'') represents a linear or branched saturated or unsaturated alkyl group having an average of 8 to 24 carbon atoms, Z o (This refers to an oligoglycoside group or a mixture thereof that has an average of 1 to 10 hexose units or pentose units.)

[0091] 12. Natural substances and their derivatives, such as lecithin, lanolin, saponins, cellulose; cellulose alkyl ethers and carboxyalkylcellulose (in which case the alkyl group has up to four carbon atoms).

[0092] 13. Linear organo(poly)siloxanes containing polar groups, particularly those containing elements O, N, C, S, P, and Si, especially linear organo(poly)siloxanes having up to 24 carbon atoms and / or up to 40 EO groups and / or PO groups having alkoxy groups.

[0093] Examples of cationic emulsifiers are as follows:

[0094] 14. Salts of primary, secondary, and tertiary aliphatic amines having 8 to 24 carbon atoms with acetic acid, sulfuric acid, hydrochloric acid, and phosphoric acid.

[0095] 15. Quaternary alkylammonium and alkylbenzeneammonium salts, especially those in which the alkyl group has 6 to 24 carbon atoms, particularly halides, sulfates, phosphates and acetates.

[0096] 16. Alkylpyridinium, alkylimidazolinium, and alkyloxazolinium salts, particularly those having an alkyl chain with up to 18 carbon atoms, specifically halides, sulfates, phosphates, and acetates.

[0097] The following are particularly suitable amphoteric emulsifiers:

[0098] 17. Amino acids having long-chain substituents, for example, salts of N-alkyldi(aminoethyl)glycine or N-alkyl-2-aminopropionic acid.

[0099] 18. Betaine, e.g., C8~C 18 N-(3-acylamidopropyl)-N,N-dimethylammonium salt having an acyl group, and alkylimidazolinium betaine, or quaternary alkyl or substituted alkyl derivatives of N,N-dimethylglycine.

[0100] Preferred emulsifiers for producing pre-crosslinked organopolysiloxanes for aqueous dispersions are nonionic emulsifiers, particularly alkyl polyglycol ethers listed in 6.k above.

[0101] The component (3) may consist of one or more of the emulsifiers, and it may be used in pure form or in the form of a solution of one or more emulsifiers in water or an organic solvent.

[0102] In the production of the dispersion of the present invention, the emulsifier (3) is used in all cases in an amount preferably 0.1% to 60% by weight, more preferably 0.5% to 30% by weight, based on the total weight of the aminoorganopolysiloxane (1) and ester (2).

[0103] If the aminoorganopolysiloxane (1) or ester (2), or the resulting pre-crosslinked organopolysiloxane itself, acts as an emulsifier, there is no need to add a separate emulsifier (3).

[0104] The emulsification process for producing the dispersion is preferably carried out at a temperature below 120°C, more preferably between 5°C and 100°C, and particularly preferably between 10°C and 80°C. The temperature increase is preferably brought about by introducing the mechanical shear energy required for the emulsification process. The temperature increase is not necessary to accelerate the chemical process. Furthermore, the dispersion is preferably produced at ambient pressure, but may be produced at higher or lower pressures.

[0105] The reaction between the aminoorganopolysiloxane (1) and the ester (2) in the preparation of the dispersion preferably proceeds within a few minutes to a few days.

[0106] In the preparation of the dispersion, the alcohol obtained as a condensation by-product may remain in the product or may be removed by means of vacuum distillation, membrane method or extraction, for example.

[0107] The average particle size measured by laser diffraction in the dispersion of the present invention (using a Mastersizer 3000 particle size analyzer manufactured by Malvern Panalytical) is preferably in the range of 0.001 to 50 μm, preferably 0.005 to 20 μm, and particularly preferably in the range of 0.01 to 10 μm.

[0108] The pH can vary between 1 and 14, preferably 3 and 9, and more preferably 4 and 8.

[0109] The present invention provides a cosmetic composition comprising an aqueous dispersion, preferably an aqueous emulsion, of a pre-crosslinked organopolysiloxane.

[0110] In all cases, the cosmetic composition of the present invention comprises an aqueous dispersion of a pre-crosslinked organopolysiloxane in an amount preferably 0.2% to 65% by weight, more preferably 0.5% to 50% by weight, based on the total weight of the cosmetic composition.

[0111] The cosmetic composition of the present invention preferably contains water as a cosmetic-acceptable medium.

[0112] The cosmetic composition of the present invention preferably comprises a conditioning agent. The term conditioning agent is used in accordance with Chapter 14 of "The Chemistry and Manufacture of Cosmetics," Vol. II, Formulating, 3rd edition, Mitchell L. Schlossmann, 2000, pp. 359-396, by K. Krummel, Stephane Chiron, and J. Jachowicz, to refer to a cosmetic component that modifies the hair surface and affects the condition of the hair. Cosmetic compositions comprising a conditioning agent are used to modify or improve the softness of the hair, to increase the ease of detangling, to reduce the combing force when wet and dry, to care for the hair, to prevent static electricity, to facilitate a smoother glide effect through and along the hair surface, to improve the shine of the hair, to maintain the color fastness of the hair, to reduce hair breakage, to maintain the shape of the hair, and for further cosmetic properties related to natural and healthy hair.

[0113] The cosmetic composition of the present invention improves one or more of the above effects, particularly combability and the adhesion of silicone to the hair.

[0114] Examples of conditioning agents and their INCI names can be found in the "International Cosmetic Ingredient Dictionary & Handbook" edited by the Personal Care Product Council.

[0115] For reference, you can use 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.

[0116] The conditioning agent used is preferably selected from the following group. Cationic polymers, Cationic surfactants, Nonpolymeric quaternary ammonium compounds, Pre-crosslinked organopolysiloxanes containing structural units of general formula (I), different organopolysiloxanes, and organopolysiloxane copolymers. Fatty acid esters and fatty acid alcohols, Natural or synthetic oils and waxes, and Panthenol, lipids, proteins, and hydrolyzed proteins, And mixtures thereof.

[0117] A preferred example of a conditioning agent is a cationic polymer. These are understood to mean polymers that have a pendant or terminal cationic group, or a pendant or terminal group that can be converted to a cationic group by ionization.

[0118] It is preferable to use a cationic polymer having a quaternary ammonium group.

[0119] Examples of cationic polymers that are preferably used are published in the International Cosmetic Ingredient Dictionary & Handbook under the name polyquaternium, and each polymer is identified by an individual numerical abbreviation, such as polyquaternium-1.

[0120] Further examples of cationic polymers include quaternary ammonium group-containing derivatives of modified polysaccharides, such as polymers having the INCI name cassia hydroxypropyltrimonium chloride, and derivatives of modified cellulose and / or starch, such as propylene glycol ether-modified Cyamopsis tetragonorova having the INCI name guar hydroxypropyltrimonium chloride. Quaternary ammonium derivatives of Tetragonoloba (guar) gum, or polymeric quaternary ammonium salts of reaction products of hydroxyethylcellulose and trimethylammonium-substituted epoxides, such as cellulose 2-hydroxyethyl 2-(2-hydroxy-3-(trimethylammonium)propoxy)ethyl 2-hydroxy-3-(trimethylammonio)propyl ether chloride, for example cellulose 2-hydroxyethyl 2-hydroxy-3-(trimethylammonium)propyl ether chloride, for example cellulose 2-hydroxyethyl 2-hydroxy-3-(trimethylammonium)propyl ether chloride, for example cellulose 2-[2-hydroxy-3-(trimethylammonium)propoxy]ethyl ether chloride, for example cellulose 2-[2-hydroxy-3-trimethylammonium]propoxy]ethyl ether chloride having the INCI name polyquaternium-10.

[0121] Further examples of cationic polymers include quaternary ammonium group-containing acrylic acid polymer derivatives, acrylic acid copolymer derivatives, methacrylic acid derivatives, and methacrylic acid copolymer derivatives, such as polymers having the INCI name polyquaternium-37.

[0122] Further examples of cationic polymers are quaternary ammonium group-containing copolymers of dimethyldiallylammonium chloride and acrylic acid, for example polymers having the INCI name Polyquaternium-22.

[0123] Further examples of cationic polymers are quaternary ammonium group-containing copolymers of vinylpyrrolidone, vinylimidazole, derivatives of vinylimidazoline and methacrylic acid, for example polymers having the INCI name Polyquaternium-86.

[0124] Further examples of cationic polymers are quaternary ammonium group-containing copolymers of acrylamide and dimethyldiallylammonium chloride, for example polymers having the INCI name Polyquaternium-7.

[0125] Further examples of cationic polymers are quaternary ammonium group-containing copolymers which are reaction products of diethyl sulfate with vinylpyrrolidone and dimethylaminoethyl methacrylate, for example polymers having the INCI name Polyquaternium-11.

[0126] When a cationic polymer is used, the cosmetic composition of the present invention contains the cationic polymer in an amount of preferably 0.01% by weight to 5% by weight, more preferably 0.05% by weight to 4% by weight, particularly preferably 0.10% by weight to 3% by weight, in each case based on the total weight of the cosmetic composition.

[0127] Further preferred examples of conditioning agents are cationic surfactants. Examples of cationic surfactants preferably used correspond to the materials listed in paragraphs 14 to 16 under the examples of cationic emulsifiers. Examples are cetyltrimethylammonium salts or behenyltrimethylammonium salts. The anionic counterion present may be, for example, chloride, bromide or methosulfate.

[0128] The INCI names of preferably used cationic surfactants are, for example, cetrimonium chloride, cetrimonium methosulfate, behentrimonium chloride, behentrimonium methosulfate, and stearimonium bromide.

[0129] When a cationic surfactant is used, the cosmetic composition of the present invention preferably contains the cationic surfactant in an amount of 0.1% by weight to 7% by weight, more preferably 0.15% by weight to 6% by weight, particularly preferably 0.2% by weight to 5% by weight, in each case based on the total weight of the cosmetic composition.

[0130] Further examples of conditioning agents are non-polymeric quaternary ammonium compounds. This term refers to non-polymeric ammonium compounds that exist in a cationic form or can be converted into cationic groups by ionization.

[0131] Examples of preferably used non-polymeric quaternary ammonium compounds are dimethyl dioctadecyl ammonium chloride having the INCI name distearyl dimonium chloride, N-[3-(dimethylamino)propyl]octadecanamide having the INCI name stearamidopropyl dimethylamine, or a compound having the INCI name dicocoylethyl hydroxyethylmonium methosulfate or quaternium-87.

[0132] Further preferred examples of conditioning agents are organopolysiloxanes and organopolysiloxane copolymers different from the pre-crosslinked organopolysiloxane having the structural unit of formula (I) present in an aqueous dispersion. The organopolysiloxane may exist in the form of an oil, a wax, a gum or a resin, or in the form of an emulsion.

[0133] Examples of such organopolysiloxanes different from the pre-crosslinked organopolysiloxane having the structural unit of formula (I) are as follows, Cyclic organopolysiloxane of the following formula [R *2SiO] x’ [In the equation, x' is an integer between 4 and 8.] Linear organopolysiloxanes of the following general formulas R * 3SiO[R * 2SiO] y SiR * 3 or HOSiR * 2O[R * 2SiO] y SiR * 2OH [In the formula, y is an integer between 0 and 2000.] and the following general formula resin-like organopolysiloxanes R * t SiO (4-t) / 2 [In the formula, R * In either case, R, R 1 Alternatively, for A, preferably R and R 1 As defined above, t is 0, 1, 2, or 3. Therefore, the organopolysiloxane resin is composed of M units, D units, T units and / or Q units, and both combinations of D units and T units, and combinations of M units and Q units, are preferred. In the case of a resin composed mainly or exclusively of D units and T units, the T units are preferably present in a molar ratio T / [M+D+T+Q] of 0.45 to 1, more preferably 0.55 to 1.0, and the number of M units and Q units is preferably zero in both cases. In the case of an organopolysiloxane resin composed mainly or exclusively of M units and Q units, the Q units are preferably present in a molar ratio Q / [M+D+T+Q] of 0.25 to 0.9, more preferably 0.35 to 0.7, and the number of D units and T units is preferably zero in both cases.

[0134] Examples of organopolysiloxanes that exist in oil form include polydimethylsiloxane, INCI-designated disiloxane, and dimethicone, which have viscosities ranging from 0.65 to 2,000,000 mPas (25°C).

[0135] Further examples of organopolysiloxanes existing in the form of oils or waxes include functionalized organopolysiloxanes, for example, polyalkylsiloxanes in which at least one alkyl group is different from methyl, for example, organopolysiloxanes having INCI names stearyl dimethicone, cetyl dimethicone, or C26-28 alkyl dimethicone, or polyarylsiloxanes and polyarylalkylsiloxanes, for example, having INCI names phenyl trimethicone, trimethylsiloxyphenyl dimethicone, or dimethylphenyl dimethicone. The material is an organopolysiloxane, or an organopolysiloxane having an organic functional group such as aminopropyl, aminopropylaminoethyl, or aminopropylaminoisobutyl, for example, an organopolysiloxane having the INCI name amodimethion, or an organopolysiloxane having a polyethylene glycol or polyalkylene glycol group, for example, an organopolysiloxane having the INCI names PEG12 dimethicone, PEG / PPG-25,25-dimethicone, or cetyl PEG / PPG-15 / 15 butyl ether dimethicone.

[0136] Further examples of organopolysiloxanes are silicone resins having the INCI names trimethylsiloxysilicate or polymethylsilsesquioxane.

[0137] When such organopolysiloxanes or organopolysiloxane copolymers are used, the cosmetic composition of the present invention contains, in each case, an organopolysiloxane and organopolysiloxane copolymer different from the pre-crosslinked organopolysiloxane having structural units of formula (I) present in the aqueous dispersion, preferably in an amount of 0.1% to 40% by weight, more preferably 0.2% to 30% by weight, and particularly preferably 0.3% to 20% by weight, based on the total weight of the cosmetic composition.

[0138] Further preferred examples of conditioning agents are fatty acid esters and fatty acid alcohols.

[0139] Examples of fatty acid alcohols include alcohols having a C8-C28 carbon chain, such as 1-octadecanol, a fatty alcohol 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.

[0140] In addition to their conditioning properties, fatty acid alcohols also provide structuring and thickening effects in cosmetic compositions.

[0141] Further examples of fatty acid esters include esters of fatty acids having the INCI names palmitic acid, oleic acid, linoleic acid, caprylic acid, myristic acid, and stearic acid, such as fatty acid esters having the INCI names isopropyl palmitate, ethylhexyl palmitate, isopropyl myristate, and isopropyl stearate.

[0142] When fatty acid esters and fatty acid alcohols are used, the cosmetic composition of the present invention contains the fatty acid esters and fatty acid alcohols in an amount preferably 0.1% to 15% by weight, more preferably 0.3% to 12% by weight, and particularly preferably 0.5% to 10% by weight, based on the total weight of the cosmetic composition.

[0143] Further preferred examples of conditioning agents are natural or synthetic oils and waxes.

[0144] Examples of preferred oils and waxes include oils and waxes having hydrocarbons with linear or branched saturated or unsaturated C4-C60 carbon chains, such as INCI names isododecane, hydrated polyisobutylene, hydrated polydecene, paraffins, and isoparaffins.

[0145] Further examples of preferred oils and waxes are carnauba wax, beeswax, lanolin wax, microcrystalline wax, jojoba oil, rice oil, calendula oil, sunflower oil, soybean oil, coconut oil, olive oil, and almond oil.

[0146] When natural or synthetic oils and waxes are used, the cosmetic composition of the present invention contains oils and waxes, in each case based on the total weight of the cosmetic composition, preferably in an amount of 0.1% by weight to 10% by weight, more preferably 0.2% by weight to 7% by weight, particularly preferably 0.3% by weight to 5% by weight.

[0147] Further preferred examples of conditioning agents are panthenol, lipids such as ceramides, proteins, and hydrolyzed proteins, such as hydrolyzed collagen, hydrolyzed wheat protein, and hydrolyzed silk.

[0148] The cosmetic composition optionally further comprises additives conventionally used in cosmetics, such as, for example, surfactants, thickeners, gelling agents, film-forming agents, humectants, UV filters, pearlescent pigments, vitamins, antioxidants, caffeine, anti-dandruff active ingredients or preservatives.

[0149] Examples of further additives conventional in cosmetology and under their INCI names are described in the "International Cosmetic Ingredient Dictionary & Handbook" of the Personal Care Product Council.

[0150] The cosmetic composition optionally further comprises additives conventionally used in cosmetics, such as surfactants.

[0151] Examples of surfactants conventional in cosmetics are also described in K. Schrader, A. Domsch, Cosmetology-Theory and Practice, Volume II, pages II-8 to II-22, Verlag fuer chemische Industrie, 2005, and are also described in items 1. to 18. under the section of examples of emulsifiers.

[0152] Examples of preferred anionic surfactants correspond to the materials listed in sections 1 to 3 below under Examples of Anionic Emulsifiers.

[0153] The INCI names of the anionic surfactants that are preferably used are, for example, sodium lauryl sulfate, ammonium laureth sulfate, sodium laureth sulfate, disodium 2-sulfolaurate, disodium lauryl sulfosuccinate, or disodium laureth-sulfosuccinate.

[0154] When an anionic surfactant is used, the cosmetic composition of the present invention contains the anionic surfactant in an amount preferably 1% to 30% by weight, more preferably 5% to 25% by weight, and particularly preferably 7% to 20% by weight, based on the total weight of the cosmetic composition.

[0155] Examples of preferred nonionic surfactants correspond to the materials listed in sections 5-13 below the examples of nonionic emulsifiers.

[0156] Preferred nonionic surfactants have INCI names such as coco glucoside, lauryl glucoside, decyl glucoside, PEG-40 hydrogenated castor oil, polysorbate 80, or PEG-7 glyceryl cocoate.

[0157] When using a nonionic surfactant, the cosmetic composition of the present invention contains the nonionic surfactant in an amount preferably 1% to 15% by weight, more preferably 2% to 12% by weight, and particularly preferably 3% to 10% by weight, based on the total weight of the cosmetic composition.

[0158] Examples of preferred amphoteric surfactants correspond to the materials listed in sections 17 and 18 below the examples of nonionic emulsifiers. More preferred examples are compounds from the types of alkylamide betaines, alkyl amphoacetates, and alkyl amphopropionates.

[0159] Preferred nonionic surfactants have INCI names such as cocamidopropyl betaine, cetyl betaine, cocamide MEA, cocamide DEA, cocamide MIPA, sodium cocoamphoacetate, or sodium cocoamphopropionate.

[0160] When using an amphoteric surfactant, the cosmetic composition of the present invention contains the amphoteric surfactant in an amount preferably 1% to 15% by weight, more preferably 2% to 12% by weight, and particularly preferably 3% to 10% by weight, based on the total weight of the cosmetic composition.

[0161] The cosmetic composition may optionally further contain additives that are conventionally used in cosmetics, such as thickeners.

[0162] Examples of preferred thickeners include modified polysaccharides, such as starch, cellulose, gum arabic, and guar gum, such as polymers having INCI names cellulose gum, guar gum, xanthan gum, or cassia gum.

[0163] Further examples of thickeners include hydrophobically modified nonionic cellulose derivatives, such as cellulose derivatives having the INCI name hydroxyethylcellulose.

[0164] Further examples of thickeners include polymers having crosslinked acrylic acid and methacrylic acid polymers and derivatives thereof, such as INCI-named carbomers.

[0165] Further examples of thickeners are agents that achieve a thickening effect in combination with surfactants. Examples include monoglycerides of fatty acids, mono / diglycerides of ethoxylated fatty acids, and ethoxylated fatty alcohols.

[0166] The INCI names of thickeners that are preferably used in combination with surfactants to achieve a thickening effect are PEG-120 methyl glucose dioleate, PEG-150 distearate, myristyl glycol, PEG-200 glyceryl palmitate, laureth-4, or PEG-200 glyceryl palmitate.

[0167] Further examples of thickeners are salts, such as salts having the INCI name sodium chloride.

[0168] When a thickening agent is used, the cosmetic composition of the present invention contains the thickening agent in an amount of preferably 0.1% to 10% by weight, based on the total weight of the cosmetic composition.

[0169] The cosmetic composition may optionally further contain additives that are conventionally used in cosmetics, such as film-forming agents.

[0170] A preferred example of a film-forming agent is a polymer.

[0171] Examples of film-forming polymers that are preferably used are listed in the Personal Care Product Council's "International Cosmetic Ingredient Dictionary & Handbook."

[0172] Preferred film-forming polymers include acrylic acid polymer derivatives, acrylic acid copolymer derivatives, methacrylic acid derivatives, and methacrylic acid copolymer derivatives.

[0173] Examples of preferred anionic polymers include copolymers of vinyl acetate with one or more acrylic acid monomers, methacrylic acid monomers, or esters thereof, such as polymers having the INCI name acrylate / VA copolymer.

[0174] Further examples of preferred film-forming polymers include copolymers of vinylpyrrolidone with one or more acrylic acid monomers, methacrylic acid monomers, or esters thereof, such as polymers having the INCI name acrylate / VP copolymer.

[0175] Further examples of preferred film-forming polymers include copolymers of tert-butylacrylamide with one or more acrylic acid monomers, methacrylic acid monomers, or esters thereof, for example, polymers having the INCI name acrylate / t-butylacrylamide copolymer.

[0176] Further examples of preferred film-forming polymers include copolymers of vinyl acetate, crotonic acid, and vinyl neodecanoate monomers, for example, polymers having the INCI name VA / crotonic acid / vinyl neodecanoate copolymer.

[0177] Further examples of preferred film-forming polymers include copolymers of vinyl acetate, crotonic acid, and vinyl neodecanoate monomers, such as polymers having the INCI name crotonic acid / vinyl C8-C12 isoalkyl ester / VA / bis-vinyl dimethicone copolymer.

[0178] When a film-forming polymer is used, the cosmetic composition of the present invention contains the film-forming polymer in an amount preferably 0.1% to 15% by weight, more preferably 0.2% to 10% by weight, and particularly preferably 0.3% to 7% by weight, based on the total weight of the cosmetic composition.

[0179] The cosmetic composition may optionally further contain additives that are conventionally used in cosmetics, such as moisturizers.

[0180] Examples of preferred humectants include glycerol, sorbitol, xylitol, polyethylene glycol, propane-1,2-diol, propane-1,3-diol, or polypropylene glycol.

[0181] When a humectant is used, the cosmetic composition of the present invention contains the humectant in an amount preferably 0.1% to 10% by weight, more preferably 0.2% to 8% by weight, and particularly preferably 0.3% to 6% by weight, based on the total weight of the cosmetic composition.

[0182] The cosmetic composition may optionally further contain additives that are conventionally used in cosmetics, such as pearlescent agents.

[0183] Examples of preferred pearlescent agents include pearlescent pigments or glycol distearates.

[0184] When an agent that imparts pearlescent luster is used, the cosmetic composition of the present invention contains the agent that imparts pearlescent luster in an amount preferably 0.1% to 7% by weight, more preferably 0.2% to 6% by weight, and particularly preferably 0.3% to 5% by weight, based on the total weight of the cosmetic composition.

[0185] The cosmetic composition is preferably prepared by mixing at least one aqueous dispersion of the pre-crosslinked organopolysiloxane of the present invention with at least one conditioning agent and optionally further conventional cosmetic additives in a cosmetic-acceptable medium, preferably water.

[0186] The individual components can be mixed with each other using high-temperature / high-temperature, high-temperature / low-temperature, or low-temperature / low-temperature processes.

[0187] In the production of the cosmetic composition of the present invention, the dispersion of the pre-crosslinked organopolysiloxane of the present invention is added preferably at a maximum temperature of 50°C, more preferably at a maximum temperature of 40°C, and particularly preferably at a maximum temperature of 35°C. These are added preferably at a temperature of at least 5°C, more preferably at least 10°C.

[0188] The cosmetic composition of the present invention may exist in the form of an emulsion, suspension, solution, cream, lotion, mousse, stick, soap bar, paste, or gel.

[0189] The cosmetic composition of the present invention in emulsion form may exist 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.

[0190] When the objective is to produce a cosmetic composition comprising an aqueous dispersion of the pre-crosslinked organopolysiloxane of the present invention in the form of an emulsion having a translucent or transparent appearance, it is preferable to use an aqueous dispersion of the pre-crosslinked organopolysiloxane of the present invention having a particle size of less than 700 nm, more preferably less than 400 nm, and particularly preferably 300 nm.

[0191] The present invention further provides the use of the cosmetic composition for treating keratin fibers such as hair. The cosmetic composition is preferably used for washing and caring for keratin fibers such as hair, or for shaping keratin fibers such as hair.

[0192] Examples of products for hair cleansing and care include hair shampoo, hair rinse (rinse-off conditioner), hair treatment, hair mask, hair serum, hair mousse, hair styling spray, hair cream, hair gel, hair oil, hair end fluid, and hair dye.

[0193] The present invention further provides the use of the cosmetic composition of the present invention for conditioning keratin fibers, such as hair, particularly for the purpose of making keratin fibers easier to comb.

[0194] The present invention further provides a process for treating keratin fibers, preferably hair, by applying the cosmetic composition of the present invention to keratin fibers, preferably hair, and then optionally rinsing with water. [Examples]

[0195] In the examples described below, all amounts reported in parts and percentages are based on weight unless otherwise specified. Furthermore, all viscosity data are for a temperature of 25°C. Unless otherwise specified, the following examples are carried out at ambient pressure, i.e., about 1020 hPa, at room temperature, i.e., about 20°C, or at the temperature at which the reactants are combined at room temperature without supplemental heating or cooling.

[0196] <Synthesis of oxalamido-ethyl-ester-terminated organopolysiloxanes S1-S2> <Synthesis of oxalamido-ethyl-ester-terminated organopolysiloxane S1> An apparatus consisting of a 4 L three-necked flask equipped with a magnetic stirrer bar, magnetic stirrer, reflux condenser, internal thermometer, and dropping funnel was inactivated with nitrogen gas. Next, 2679 g (18.45 mol) of diethyl oxalate (M=146.14 g / mol, CAS number 95-92-1, available from Sigma-Aldrich (Munich, Germany)) was initially packed into the flask under a continuous flow of nitrogen. To this, 600 g (4.07 mol) of (3-aminopropyl)dimethylmethoxysilane (M=147.29 g / mol, CAS number 31024-26-7, available from Gelest (Morrisville, USA)) was added dropwise with continuous stirring at a rate that maintained the temperature of the reaction mixture below 50°C throughout. This yielded a slightly yellowish clear liquid, which was then stirred at room temperature for a further 1 hour after the addition was complete. The excess diethyl oxalate was then removed under reduced pressure (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. 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))P1 (M=247.37 g / mol), was distilled as a colorless, clear liquid at a vacuum boiling range of 136-141°C / 2 mbar. The yield was 94% based on the (3-aminopropyl)dimethylmethoxysilane used.

[0197] First, 164.95 g (0.66 mol) of P1 and 740 g (10.00 mol Si) of α,ω-OH-terminated linear dimethylsiloxane (CAS number 70131-67-8) with a viscosity of 50 mPas were placed in a 2 L round-bottom flask. The round-bottom flask containing the reaction mixture was heated in a rotary evaporator in a 130°C oil bath under a vacuum of 6 mbar for 30 minutes under rotation. Next, the vacuum was released, and a 40% solution of PNCl2 in ethyl acetate was added. The mixture was then heated under reduced pressure in a rotary evaporator (130°C oil bath, 6 mbar vacuum) for 1 hour. Next, the vacuum was released again, and a 40% solution of PNCl2 in ethyl acetate (10 ppm PNCl2) was added. The mixture was then heated under reduced pressure in a rotary evaporator (130°C oil bath, 6 mbar vacuum) for a further 1 hour. Next, the vacuum was released again, and a 40% solution of PNCl2 in ethyl acetate (10 ppm PNCl2) was added. The mixture was heated under reduced pressure for 4 hours in a rotary evaporator (oil bath at 130°C, vacuum at 6 mbar). After cooling to room temperature, 8 g of magnesium oxide (heavy MgO, CAS number 1309-48-4, available from Sigma-Aldrich, Munich, Germany) was added to the flask contents, and the mixture was stirred at room temperature for 1 hour. The suspension was then filtered through a Seitz® T-120 depth filter (available from Pall Corporation, New York, USA) under a pressure of 6 mbar. This yielded 793 g of colorless, transparent oil with a viscosity of approximately 95 mPas.

[0198] <Synthesis of oxalamido-ethyl-ester-terminated organopolysiloxane S2> In a stirring flask apparatus consisting of a 1 L three-necked flask equipped with a heating mantle, mechanical stirrer, internal thermometer, and water separator with reflux condenser, 400 g (5.41 mol Si) of α,ω-OH-terminated linear dimethylsiloxane (CAS number 70131-67-8) with a viscosity of 50 mPas and 19.8 g (0.08 mol) of P1 were first added and heated to 80°C while stirring. After adding 50 mg of PNCl2 (100%), the pressure was reduced (10 mbar) and the flask contents were heated to 100°C. The generated water was removed using a water separator. After 5 minutes, the vacuum was adjusted to 40 mbar and the mixture was stirred under these conditions for 30 minutes. Then the vacuum was released and a further 25 mg of PNCl2 (100%) was added, and the mixture was heated at 100°C and 40 mbar while stirring. Next, the vacuum was released again, 25 mg of PNCl2 (100%) was added, and the mixture was further heated at 100°C and 40 mbar while stirring. Then, the vacuum was released, the mixture was cooled to an internal temperature of 70-80°C, and the contents of the flask were neutralized by adding 2.5 g of anhydrous sodium (light sodium carbonate, CAS number 497-19-8, available from Sigma-Aldrich (Munich, Germany)). The mixture was stirred for a further 30 minutes and then filtered. This yielded a clear oil with a viscosity of approximately 525 mPas.

[0199] <Formation of aminosilicone oil emulsions E1-E3> <Formation of aminosilicone oil emulsion E1> 4.9 g of an 80% aqueous solution of isotridecyl decaethoxylate, commercially available under the trade name Lutensol TO10 (from BASF), and 1.6 g of desalted water are pre-mixed at 4000 rpm using an Ultra-Turrax T50 emulsifier (from Janke & Kunkel / IKA). The resulting compound consists of 3-(2-aminoethylamino)propylmethylsiloxy units and dimethylsiloxy units, with an amine value of 0.14 equivalents / g and a viscosity of 4000 mmHg. 234.9 g of a hydroxy / methoxy-terminated copolymer having a shear rate of 4000 rpm (at 25°C) was added in three portions to produce a relatively rigid pre-emulsion phase. This was diluted with 57.5 g of desalted water, which was added gradually at a low shear rate, to obtain the desired emulsion, which was then mixed with 0.20 g of 80% acetic acid and 0.9 g of 2-phenoxyethanol.

[0200] This yields a smooth, low-viscosity white silicone oil emulsion E1 with a solid content of 39.8% and a pH of 5.0.

[0201] The D50 value at 160 nm is obtained by measuring the particle size distribution.

[0202] <Formation of aminosilicone oil emulsion E2> 30.0 g of an 80% aqueous solution of isotridecyl decaethoxylate, commercially available under the trade name Lutensol TO 10 (from BASF), composed of 3-(2-aminoethylamino)propyl-methylsiloxy units and dimethylsiloxy units, with an amine value of 0.6 equivalents / g and a viscosity of 2500 mmHg. 2 81.7 g of trimethylsilyl-terminated copolymer with a viscosity of 60,000 mmHg / second (at 25°C) 2 86.3 g of trimethylsilyl-terminated polydimethylsiloxane at 1 / second (at 25°C) is pre-mixed at 500 rpm in a container of a lab planetary mixer (model Labmax, Molteni). 39.6 g of demineralized water and 1.4 g of 80% acetic acid are added (at 500 rpm), and the mixture is homogenized over 3 cycles at a shear rate of 2500 rpm to obtain a soft to medium-hard solid phase as a pre-emulsion. This is diluted with 157.4 g of demineralized water, added gradually at a relatively low shear rate, to obtain the desired emulsion, which is then mixed with 3.6 g of 2-phenoxyethanol.

[0203] This yields a smooth, fluid white silicone oil emulsion E2 having a solids content of 48.9% and a pH of 5.5.

[0204] The D50 value at 180 nm is obtained by measuring the particle size distribution.

[0205] <Formation of aminosilicone oil emulsion E3> 32.0 g of an 80% aqueous solution of isotridecyl decaethoxylate, commercially available under the trade name Lutensol TO10 (from BASF), composed of 3-(2-aminoethylamino)propyl-methylsiloxy units and dimethylsiloxy units, with an amine value of 0.14 equivalents / g and a viscosity of 4000 mmHg. 2 44.0 g of hydroxy / methoxy-terminated copolymer with a viscosity of 60,000 mm² / second (at 25°C) 2 132.0 g of trimethylsilyl-terminated polydimethylsiloxane at 1 / sec (at 25°C) is pre-mixed at 500 rpm in a container of a lab planetary mixer (Model Labmax, Molteni). 20.0 g of demineralized water and 0.3 g of 80% acetic acid are added (at 500 rpm), and the mixture is homogenized over 3 cycles at a shear rate of 2500 rpm to obtain a solid phase as a pre-emulsion. This is diluted with 168.1 g of demineralized water, added gradually at a relatively low shear rate, to obtain the desired emulsion, which is then mixed with 3.6 g of 2-phenoxyethanol.

[0206] This yields a smooth, easily mobile white silicone oil emulsion E3 having a solids content of 51.3% and a pH of 5.0.

[0207] The D50 value at 257 nm is obtained by measuring the particle size distribution.

[0208] [Examples 1-4] Examples 1 to 4 below illustrate methods for synthesizing aqueous dispersions of pre-crosslinked organopolysiloxanes used to produce the cosmetic compositions of the present invention.

[0209] [Example 1] <Emulsion B1-a = B1-b> 92.26 g of aminosilicone oil emulsion E1 is homogenized with 7.74 g of oxalamido-ethyl-ester-terminated organopolysiloxane S1 using an Ultra-Turrax T50 emulsifier (Janke & Kunkel / IKA) at 5000 rpm for less than 1 minute.

[0210] This yields a smooth, low-viscosity white silicone oil emulsion B1-a (=B1-b) with a solid content of 44.5% and a pH of 5.0. The D50 value at 141 nm is obtained by measuring the particle size distribution.

[0211] After drying at 25°C for 24 hours, the emulsion is evaporated to obtain a noticeably whitish, slightly soft elastic film that is slightly sticky on the surface.

[0212] <Emulsion B1-c> 96.16 g of aminosilicone oil emulsion E1 is homogenized with 3.84 g of ochilamide-ethyl-ester-terminated organopolysiloxane S1 using an Ultra-Turrax T50 emulsifier (Janke & Kunkel / IKA) at 5000 rpm for less than 1 minute.

[0213] This yields a smooth, low-viscosity white silicone oil emulsion B1-c with a solid content of 42.1% and a pH of 5.5. The D50 value at 123 nm is obtained by measuring the particle size distribution.

[0214] After drying at 25°C for 24 hours, the emulsion is evaporated to obtain a noticeable, whitish, slightly soft, elastic film.

[0215] [Example 2] <Emulsion B2> 96.08 g of aminosilicone oil emulsion E2 is homogenized with 3.92 g of oxalamidoethyl ester-terminated organopolysiloxane S1 using an Ultra-Turrax T50 emulsifier (Janke & Kunkel / IKA) at 5000 rpm for less than 1 minute.

[0216] This yields a smooth, fluid white silicone oil emulsion B2 with a solid content of 50.9% and a pH of 6.5. The D50 value at 230 nm is obtained by measuring the particle size distribution.

[0217] After drying at 25°C for 24 hours, the emulsion is evaporated to obtain a noticeable, whitish, slightly soft, elastic film.

[0218] [Example 3] <Emulsion B3> 98.22 g of aminosilicone oil emulsion E3 is homogenized with 1.78 g of oxalamidoethyl ester-terminated organopolysiloxane S1 using an Ultra-Turrax T50 emulsifier (Janke & Kunkel / IKA) at 5000 rpm for less than 1 minute.

[0219] This yields a smooth, easily mobile white silicone oil emulsion B3 with a solid content of 52.2% and a pH of 4.5. The D50 value at 210 nm is obtained by measuring the particle size distribution.

[0220] After drying at 25°C for 24 hours, the emulsion is evaporated to obtain a noticeable, whitish, slightly soft elastic film that is slightly sticky on the surface.

[0221] [Example 4] <Emulsion B4> 85.69 g of aminosilicone oil emulsion E1 is homogenized with 14.31 g of oxalamido-ethyl-ester-terminated organopolysiloxane S2 using an Ultra-Turrax T50 emulsifier (Janke & Kunkel / IKA) at 5000 rpm for less than 1 minute.

[0222] This yields a smooth, low-viscosity white silicone oil emulsion B4 with a solid content of 48.4% and a pH of 5.5. The D50 value at 192 nm is obtained by measuring the particle size distribution.

[0223] After drying at 25°C for 24 hours, the emulsion is evaporated to obtain a noticeable, whitish, slightly soft, elastic film.

[0224] [Comparative Experiment V1] The following comparative experiment V1 represents the manufacturing process for the synthesis of a non-inventive aqueous emulsion (crosslinking with non-inventive diethyl oxalate according to US5039738A).

[0225] 99.6 g of aminosilicone oil emulsion E1 is homogenized with 0.4 g of diethyl oxalate using an Ultra-Turrax T50 emulsifier (Janke & Kunkel / IKA) at 5000 rpm for less than 1 minute.

[0226] This yields V1, a smooth, low-viscosity white silicone oil emulsion with a solid content of 40.0% and a pH of 4.5. A D50 value of 71 nm is obtained by measuring the particle size distribution.

[0227] After drying at 25°C for 24 hours, the emulsion is evaporated to obtain a white, opaque paste-like layer that exhibits weak bonding to glass and aluminum.

[0228] [Comparative Experiment V2] The following comparative experiment V2 represents the manufacturing process for the synthesis of a non-inventive aqueous emulsion (crosslinking with a non-inventive diethyl-L-tartrate according to WO20239229A).

[0229] 99.4 g of aminosilicone oil emulsion E1 is homogenized with 0.6 g of diethyl-L-tartrate using an Ultra-Turrax T50 emulsifier (Janke & Kunkel / IKA) at 5000 rpm for less than 1 minute.

[0230] This yields V2, a smooth, low-viscosity white silicone oil emulsion with a solid content of 40.2% and a pH of 5.5. A D50 value of 135 nm is obtained by measuring the particle size distribution.

[0231] After drying at 25°C for 24 hours, the emulsion is evaporated to obtain a soft, milky white elastic film with a slightly sticky surface.

[0232] <Rheology of elastomer film after water removal> A Teflon® ring with an inner diameter of 40 mm was placed on a circular glass plate with a diameter of 65 mm to prepare a casting mold. 2.5 g of emulsion to be measured was weighed onto the glass plate, avoiding air bubbles. The cast emulsion was then dried at 25°C and 101.425 kPa. It was necessary to ensure that the casting mold containing the cast emulsion was positioned on a flattened surface during drying, thereby allowing for the development of a film of uniform thickness. After drying, a film of approximately 0.5 mm thickness was obtained.

[0233] After being left at 25°C for one week, the resulting film underwent rheological analysis. Measurements were performed using an MCR302 rheometer from Anton Paar, with a PP12.5 plate / plate measuring system and a gap height of 0.5 mm. The instrument was calibrated with standard oil 10000 from the Physikalisch-Technische Bundesanstalt [German Federal Physical-Technical Institute]. The measurement temperature was 25.00°C ± 0.05°C.

[0234] The values ​​listed in Table 1 for the storage modulus G', loss modulus G'', and loss coefficient tanδ can be calculated by applying sinusoidal deformation and measuring the shear stress τ and phase shift angle δ. The measurements in Table 1 were taken at a frequency of 1 Hz and a deformation of 0.1%. When subjected to deformation, the measured sample falls within the linear viscoelastic measurement range.

[0235] The following relationship applies here: tanδ = G” / G’. When tanδ < 1, the elastic properties of the sample are dominant, and when tanδ > 1, the viscous properties of the sample are dominant.

[0236] Table 1 summarizes the results of the rheological measurements of the elastomer films of Invention Examples B1-B4, Comparative Experiments V1 and V2, and non-crosslinked aminosilicone oil emulsions E1-E3.

[0237] [Table 1]

[0238] Table 1 demonstrates that emulsions B1 to B4 of the present invention, each containing oxalamidoethyl-ester-terminated organopolysiloxanes S1 and S2 as crosslinking agents, form an elastic film after water removal, since tanδ < 1.

[0239] The non-inventive emulsion V1 shows no elastic film formation at all after water removal because tanδ is greater than 1.

[0240] The non-inventive emulsion V2, which contains diethyl-L-tartrate as a crosslinking agent component, exhibits the formation of an elastic film after water is removed according to WO20239229A1, since tanδ<1.

[0241] The evaporated pure aminosilicone oil emulsions E1-E3 do not show film formation after water removal, as tanδ is significantly greater than 1 in all cases. This indicates that the addition of a crosslinking agent is necessary to achieve film formation.

[0242] <Test methods for evaluating the effectiveness of cosmetic compositions> Natural hair The application behavior of cosmetic compositions and their effects on combability and flexibility were evaluated on Caucasian hair available from Kerling International Haarfabrik GmbH. Before use, undamaged locks of natural hair were washed and, where appropriate, damaged by bleaching in a further process step.

[0243] Basic cleaning For cleaning, place undamaged hair tufts in a methyl isobutyl ketone solution for 1 hour and shake. After removing the solvent mixture, wash the hair tufts twice in each case with 3 ml of ammonium lauryl sulfate solution (25%), STEPANOL® ALS25 from STEPAN Company, and then demineralized water at 30°C. Loosen the tufts using a coarse-toothed comb. Then, place the hair tufts in a large beaker of demineralized water for 1 hour, remove them, and rinse again under running demineralized water. After the basic cleaning, before further use, condition the tufts at 23°C and 50% humidity for at least 12 hours and comb them before use.

[0244] Hair bleaching - the creation of damaged hair Damaged hair is produced by bleaching washed natural hair tufts (Euro-natural hair, color 6 / 0, 20cm, tuft weight 2g from Kerling International Haarfabrik GmbH). This is done by placing five hair tufts in a solution consisting of 30% hydrogen peroxide and 25% ammonia (ratio 33.5:1) for 30 minutes in each case. The hair is then thoroughly rinsed with demineralized water and washed twice with 3 ml of ammonium lauryl sulfate solution (25%), STEPANOL® ALS25 from STEPAN Company, and demineralized water at a temperature of 30°C. The hair tufts are then placed in a large beaker of demineralized water for 1 hour, removed, and rinsed again under running demineralized water. Before further treatment, the bleached tufts are conditioned at 23°C and 50% humidity for at least 12 hours and combed before use.

[0245] Comb penetration force measurement The combing force of wet and dry hair was determined using bleached and unbleached hair stalks (Euro-natural hair, color 6 / 0, 20cm, stalk weight 2g from Kerling International Haarfabrik GmbH). The combing force was measured using an Instron 3343 tensile testing machine by the double combing method described in YK Kamath and Hans-Dietrich Weigmann, J.Soc.Cosmet.Chem., 37, 111-124, 1986. First, the combing force in the wet and dry state was determined along the measured cross-section of the untreated hair stalk. Next, the hair stalk was treated with the cosmetic composition of the present invention, and the force absorption during the combing procedure was determined. The reported measurement is the decrease in combing force (work) along the measured cross-section obtained between the treated and untreated hair stalks. The average value from five hair stalks was calculated. The decrease in combing force was reported as a percentage.

[0246] Flexibility / softness (based on tensile testing) The softness of the hair was determined using bleached and unbleached hair strands (Euro-natural hair, color 6 / 0, 20 cm, strand weight 2 g, from Kerling International Haarfabrik GmbH). The flexibility of the hair in a dry state was determined using an Instron 3343 tensile testing machine by correlating the required tensile force with the parameters of the hair bundle's bending stiffness and surface roughness. These two parameters, in turn, correlate with the softness of the hair. For this purpose, the untreated hair strands were fixed to a measuring assembly consisting of five rods positioned offset from each other. The shape of the hair strands at this starting position is a type of double S. After this preparation, the hair strands were pulled out of the measuring assembly in one direction, and the required force was evaluated as work along the measured cross section. The hair strands were then treated with the cosmetic composition of the present invention, and the force absorption when pulling the hair strands through the measuring assembly was determined along the measured cross section. The reported measurement is the decrease in tensile strength (work) along the measured cross-section obtained between treated and untreated hair strands. A large decrease in tensile strength (work) corresponds to a good soft feel / high flexibility. The average value from five hair strands is calculated.

[0247] Softness (based on panel testing) To assess the softness of hair tufts, their tactile properties are evaluated by experts (trained panelists). In all cases, hair tufts are compared in pairs, for example, shampooed hair is compared to untreated hair. The number of pairs of tufts evaluated is at least 3, and the number of panelists is at least 5. The evaluation is based on hair tufts from Kerling International Haarfabrik GmbH (Euro-natural hair, color 6 / 0, 20cm, tuft weight 2g).

[0248] Washing procedure, shampoo Apply 0.2g of shampoo per gram of hair to a clean, wet hair bundle. Massage the shampoo into the hair bundle for 30 seconds, working towards the ends. Then, rinse the hair bundle for 30 seconds with desalinated water and loosen it using a wide-toothed comb. Repeat this procedure twice. Finally, extend the rinsing process to 60 seconds. Then, dry the hair bundle at 50% humidity and 23°C for at least 12 hours.

[0249] Washing procedure, conditioner Apply 0.3g of rinse-off conditioner per gram of hair to a clean, wet hair section. Massage the rinse-off conditioner towards the ends of the hair for 120 seconds. Then, rinse the hair section for 60 seconds with desalinated water and detangle using a wide-toothed comb. Repeat this procedure. Then, dry the hair section at 50% humidity and 23°C for at least 12 hours.

[0250] Determination based on the amount of Si (ppm) attached to the hair surface (silicone adhesion). The amount of silicone adhering to the hair surface is measured using an energy-dispersive X-ray fluorescence spectrometer (AMETEK, XEPOS). Hair bundles are placed in a specially manufactured sample holder with a 12 mm diameter circular measurement area. The hair surface within the measurement area is smooth, and the hairs are aligned parallel to each other. The sample is excited in a helium atmosphere using a palladium tube (17.05 kV, 2.0 mA). The excitation time is 300 seconds. A control sample (natural hair bundle) is subjected to periodic measurements. Drift correction is performed using a glass tablet in case of deviation. The calibration standard used was a hair bundle coated with polydimethylsiloxane in the range of 50–2000 ppm (control by atomic absorption spectroscopy).

[0251] To determine the effectiveness of silicone adhesion, the amount of Si (ppm) on a clean hair bundle is first determined and used as the blank value. Then, the same hair bundle is treated, for example, by washing with shampoo. Again, the amount of Si (ppm) = sample value is determined. The amount of attached Si (ppm) is obtained by the following subtraction: sample value - blank value. Measurements are taken at the center of the opposing and back surfaces of each hair bundle. The reported results are the average values ​​from the three hair bundles.

[0252] Simulation of shampooing by agitating hair strands in a surfactant solution. Many users desire the beauty effects of hair conditioning products to persist after use, such as improved hair softness, reduced combability when wet, and retention of hair color, despite multiple subsequent washes with shampoo. To evaluate the persistence of the beauty effects after treating hair with the cosmetic composition of the present invention, a method was developed to constitute a simulation of continuous shampoo treatment. For this purpose, treated hair strands in a 100 ml jar with a screw cap were treated with a 5% solution of ammonium lauryl sulfate in 50 ml, this solution was thermally equilibrated at 40°C and obtained by diluting STEPANOL® ALS25 from STEPAN Company, and the treated strands were shaken at a speed of 250 rpm for a specified time in an incubation shaker (from Heidolph Unimax 1010 + Incubator 1000) thermally equilibrated at 40°C. After shaking, the strands were rinsed with demineralized water at a temperature of 30°C for 1 minute and dried.

[0253] High humidity curl retention test High-humidity curl retention testing allows for the evaluation of care and styling products regarding the shaping properties of hair fibers. In this model for determining hair fixation, the percentage change from the initial to the final length of a defined curled hair section is recorded relative to the subsequent hair section length. The high-humidity curl retention properties of hair care and styling products are monitored for 7 hours at 23°C and 90% relative humidity.

[0254] Assemble a 15cm long lock of brown European hair into 3.5g bundles, tie them with thread, and permanently secure them with a suitable adhesive. Wash the hair locks twice in each case with 3ml of ammonium lauryl sulfate solution (25%), STEPANOL® ALS25 from STEPAN Company, and then with demineralized water at 30°C. Comb and dry the hair locks. Spray the dried locks with 20 puffs of 3% active pump spray, comb once, then wrap them around a 1.4cm diameter plastic rod, temporarily secure with a cover, and dry overnight at 50°C.

[0255] Carefully remove the curled hair from the plastic rod. After a short cooling period, attach the curled hair to a suspended device with a scale in a climate chamber at 23°C and 90% relative humidity. Determine and record the initial length of the curled hair. Read the length of the curled hair, i.e., the change from the initial length, at specified time intervals over 7 hours.

[0256] The value is calculated according to formula (GI).

[0257]

number

[0258] The higher the curl retention rate after time t, the better the molding / fixing properties of the cosmetic formulation. The uncurling of curled strands of hair is not very noticeable.

[0259] <Examples of cosmetic compositions> The pre-crosslinked emulsion is preferably an emulsion that forms an elastic film after the removal of water and has tanδ < 1 in rheological measurements.

[0260] [Examples A1-a, A1-c, and A2-a (Rinse-off Conditioner)] The following examples represent cosmetic compositions A1-a, A1-c, and A2-a of the present invention, shown in Table 2, including pre-crosslinked emulsions B1-a, B1-c, and B2 from the corresponding examples. The activity content of organopolysiloxane in the cosmetic compositions is 0.5%.

[0261] Preparation Instructions Heat the initial water mixture to 75°C while stirring. Add 2.0 parts hydroxyethylcellulose. When the mixture reaches 65°C, add 0.5 parts polysorbate 80, 0.5 parts stearyl alcohol, 0.5 parts cetyl alcohol, and 0.2 parts behentrimonium chloride. Stir the mixture until it reaches 75°C to dissolve the components. Then, cool the mixture. During the cooling process, add 0.1 parts citric acid and 0.2 parts tetrasodium EDTA. At 35°C, add 0.9 parts phenoxyethanol and ethylhexylglycerin. Continue stirring and add the emulsion from the examples. Homogenize the composition by stirring for 15 minutes.

[0262] [Table 2]

[0263] 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, Schuelke & Mayr

[0264] [Comparative experiment VA1 and VA2 (Rinse-off conditioner (rinse))] The following comparative experiments VA1 and VA2 represent non-inventive cosmetic compositions containing non-pre-crosslinked aqueous dispersions E1 and E2 from corresponding examples. The active content of organopolysiloxane in the cosmetic compositions is 0.5%.

[0265] For the preparation of the cosmetic compositions for comparative experiments VA1 and VA2, the procedures of Examples A1-a, A1-c, and A2-a were repeated, but modified to use uncrosslinked emulsions E1 and E2 instead of emulsions B1-a, B1-c, and B2 (emulsions of the pre-crosslinked organopolysiloxane of the present invention).

[0266] Preparation Instructions Heat the initial water mixture to 75°C while stirring. Add 2.0 parts hydroxyethylcellulose. When the mixture reaches 65°C, add 0.5 parts polysorbate 80, 0.5 parts stearyl alcohol, 0.5 parts cetyl alcohol, and 0.2 parts behentrimonium chloride. Stir the mixture until it reaches 75°C to dissolve the components. Then, cool the mixture. During the cooling process, add 0.1 parts citric acid and 0.2 parts tetrasodium EDTA. At 35°C, add 0.9 parts phenoxyethanol and ethylhexylglycerin. Continue stirring and add the emulsions shown in Table 3 for comparative experiments. Homogenize the composition by stirring for 15 minutes.

[0267] [Table 3]

[0268] The raw materials listed in Table 3 are available under the following product 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, Schuelke & Mayr

[0269] [Comparative experiment VA1-DEO (Rinse-off conditioner (rinse))] The following comparative experiment, VA1-DEO, represents a non-inventive cosmetic composition containing an aqueous dispersion of a pre-crosslinked organopolysiloxane. The active content of the organopolysiloxane in the cosmetic composition is 0.5%.

[0270] In the preparation of the cosmetic composition VA1-DEO in the comparative experiment, the procedures of Examples VA1 and VA2 were repeated, but modified to use pre-crosslinked, non-inventive emulsion V1 instead of emulsions E1 and E2 (emulsions of non-pre-crosslinked organopolysiloxanes).

[0271] Preparation Instructions Heat the initial water mixture to 75°C while stirring. Add 2.0 parts hydroxyethylcellulose. When the mixture reaches 65°C, add 0.5 parts polysorbate 80, 0.5 parts stearyl alcohol, 0.5 parts cetyl alcohol, and 0.2 parts behentrimonium chloride. Stir the mixture until it reaches 75°C to dissolve the components. Then, cool the mixture. During the cooling process, add 0.1 parts citric acid and 0.2 parts tetrasodium EDTA. At 35°C, add 0.9 parts phenoxyethanol and ethylhexylglycerin. Continue stirring and add the emulsions shown in Table 4 for comparative experiments. Homogenize the composition by stirring for 15 minutes.

[0272] [Table 4]

[0273] 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, Schuelke & Mayr

[0274] <Comparison of Rinse-Off Conditioners of Invention Examples A1-a, A1-c, and A2-a with Comparative Experiments VA1 and VA2> The described examples and comparative experiments differ in that, in Examples A1-a, A1-c, and A2-a, the aqueous dispersion of the present invention of a pre-crosslinked organopolysiloxane was used, while in Comparative Experiments VA1 and VA2, similar aqueous dispersions of the corresponding non-pre-crosslinked organopolysiloxane were used in both cases. The activity content of the organopolysiloxane in the cosmetic composition is 0.5%.

[0275] In direct comparison, the following examples / comparative experiments are interrelated. Example A1-a - Comparative Experiment VA1 Example A1-c - Comparative Experiment VA1 Example A2-a - Comparative Experiment VA2

[0276] <Combability (sustained effect) in a wet state after treating damaged hair with a rinse-off conditioner and after simulating multiple shampooing treatments by agitating the hair in a surfactant aqueous solution> [Examples A1-a and A1-c - Comparative Experiment VA1] When the aqueous dispersions B1-a and B1-c of the pre-crosslinked organopolysiloxane of the present invention are used in rinse-off conditioners (Examples A1-a and A1-c), improvements in conditioning properties, such as reduced combability in a wet state, are obtained compared to the non-inventive rinse-off conditioner from Example VA1, which contains a dispersion of non-pre-crosslinked organopolysiloxane E1. A further objective of the rinse-off conditioner of the present invention is that the care properties are maintained even after the hair has been shampooed multiple times. In this example, the shampooing process is simulated by stirring hair bundles treated with the rinse-off conditioner in a surfactant solution for 4 hours. Details of this process are described above under the test method.

[0277] The results of determining the combing force in a wet state are shown below in Table 5 for the rinse-off conditioners of Examples A1-a, A1-c, and VA1.

[0278] [Table 5]

[0279] Treatment with the rinse-off conditioner of the present invention (Example A1-a), which contains an aqueous emulsion of pre-crosslinked organopolysiloxane B1-a with a value of 84%, makes it possible to achieve a significant reduction in the measured combability of hair strands in a wet state. In particular, the high conditioning effect is maintained after agitation of the treated hair in the surfactant solution, which is reflected in a sustained reduction of 39% in combability in a wet state. Similarly, treatment with the rinse-off conditioner of the present invention (Example A1-c), which contains an aqueous emulsion of pre-crosslinked organopolysiloxane B1-c, achieves a high measured reduction of 81% in the combability of hair strands in a wet state. After agitation of the treated hair in the surfactant solution, a sustained reduction of 31% in combability in a wet state is observed.

[0280] Hair treated with a non-inventive rinse-off conditioner containing emulsion E1 (Comparative Example VA1) shows a slight decrease in combability at wet conditions of 79%. However, the decrease in combability at wet conditions of 21% after surfactant treatment is significantly lower compared to Examples A-1a and A-1c. Treating hair in the surfactant solution represents a simulation of washing the hair multiple times with shampoo, demonstrating that the rinse-off conditioner of the present invention exhibits better wash resistance and that the conditioning properties are maintained longer than when hair is treated with the non-inventive rinse-off conditioner.

[0281] <Comparison of silicone adhesion after treating damaged hair with a rinse-off conditioner and after simulating multiple shampooing treatments by agitating the hair in a surfactant aqueous solution for 4 hours.> [Example A2-a - Comparative Experiment VA2] As a further criterion, the efficiency of silicone adhesion to damaged hair after treatment with rinse-off conditioner was evaluated, and in addition, the amount of conditioning organopolysiloxane remaining on the hair surface after a simulation of shampooing by agitating the hair in a surfactant solution for 4 hours was examined. The results are summarized in Table 6. The determination of silicone adhesion is described above under the test methods.

[0282] [Table 6]

[0283] Table 6 shows that the silicone adhesion in Example A2-a of the present invention (even after shampooing) is more effective and more resistant to shampooing compared to the non-inventive comparative experiment VA2.

[0284] <Comparison of Rinse-Off Conditioner (Example A1-a) with Comparative Experiment VA1-DEO> The described examples and comparative experiments differ in that, in Example A1-a, the aqueous dispersion of the pre-crosslinked organopolysiloxane of the present invention was used, while comparative experiment VA1-DEO used a similar non-inventive aqueous dispersion of the corresponding pre-crosslinked organopolysiloxane. The active content of the organopolysiloxane in the cosmetic composition is 0.5%.

[0285] <Combability (sustained effect) of wet hair after treating damaged hair with a rinse-off conditioner and after simulating multiple shampooing treatments by agitating the hair in a surfactant aqueous solution> [Example A1-a - Comparative Experiment VA1-DEO] When the aqueous dispersion B1-a of the pre-crosslinked organopolysiloxane of the present invention is used in a rinse-off conditioner (Example A1-a), an improvement in conditioning properties, such as reduced combability in a wet state, is achieved compared to the non-inventive rinse-off conditioner from Example VA1-DEO, which includes a dispersion of the pre-crosslinked organopolysiloxane (Comparative Experiment V1). A further objective of the rinse-off conditioner of the present invention is that the care properties are maintained even after the hair has been shampooed multiple times. In this example, the shampooing process is simulated by stirring hair bundles treated with the rinse-off conditioner in a surfactant solution for 4 hours. Details of this treatment are described above under the test method.

[0286] The results of determining the combing force in a wet state are shown below in Table 7 for the rinse-off conditioners of Examples A1-a and VA1-DEO.

[0287] [Table 7]

[0288] Treatment with the rinse-off conditioner of the present invention (Example A1-a), which contains an aqueous emulsion of pre-crosslinked organopolysiloxane B1-a with a value of 84%, makes it possible to achieve a significant reduction in the combability of hair strands when wet, as measured. In particular, the high conditioning effect is maintained after agitation of the treated hair in the surfactant solution, which is reflected in a sustained reduction of 39% in combability when wet.

[0289] Hair treated with the non-inventive rinse-off conditioner VA1-DEO, which contains an emulsion from Comparative Example V1, shows a slightly reduced decrease in combability in a wet state of 77%. However, the 20% decrease in combability in a wet state after surfactant treatment is significantly lower compared to Example A-1a. Treatment of hair in the surfactant solution represents a simulation of multiple hair washes with shampoo, demonstrating that the rinse-off conditioner of the present invention exhibits better wash resistance and that the conditioning properties are maintained longer than when hair is treated with the non-inventive rinse-off conditioner.

[0290] [Example A3-a] Cosmetic composition: Shampoo The following examples represent cosmetic composition A3-a of the present invention, which includes emulsion B3. Comparative example VA3 is 60,000 mm 2 This represents a commercially available shampoo formulation containing a dimethicone (dimethylpolysiloxane, BELSIL® DM5102E, available from Wacker Chemie) emulsion with a viscosity of 1 / second (25°C). The active content of organopolysiloxane in the cosmetic composition is 1.3%.

[0291] The composition of the shampoo is summarized in Table 8.

[0292] Preparation Instructions Heat the initial packing of 32.11 parts water to 50°C with stirring. During this time, add 0.20 parts guar hydroxypropyltrimonium chloride, 6.06 parts sodium lauryl sulfate, 29.90 parts sodium laureth sulfate, 0.05 parts citric acid, and 5.0 parts cocamidopropyl betaine. Stir the mixture until it reaches 50°C to dissolve the components. Then, let the mixture cool. Add 20.0 parts water to a separate container and add 0.60 parts carbomer with stirring, continuing to stir until a homogeneous mixture is obtained. Then, add 0.06 parts lactic acid. Add this mixture to the first mixture. At 40°C, add 0.95 parts phenoxyethanol and ethylhexylglycerin. Continue stirring and add 0.30 parts of C12-13 alkyl lactate, 2.91 parts of the present invention's emulsion B3 or 2.60 parts of the non-inventive dimethicone emulsion BELSIL® DM5102E, 0.40 parts of sodium hydroxide, and 0.66 parts of sodium chloride. The pH can be adjusted to the required value of 6.5 by adding sodium hydroxide as needed.

[0293] [Table 8]

[0294] <Comparison of shampoo from Example A3-a with comparative experiment VA3> The described examples and comparative experiments differ in that Example A-3a uses an aqueous dispersion of pre-crosslinked organopolysiloxane. In comparative experiment VA3, commercially available aqueous dimethylpolysiloxane emulsion BELSIL® DM5102E (Wacker Chemie) was used, which contains 60,000 ml as an effective conditioning component. 2 It contains dimethicone (dimethylpolysiloxane) with a viscosity of 1 / second. The active content of organopolysiloxane in the cosmetic composition is 1.3%.

[0295] The results of the shampoo's beauty effects are summarized in Table 9.

[0296] [Table 9]

[0297] The shampoo of Example A-3a, which contains the emulsion of the present invention, exhibits substantially higher reduced combability in a wet state and significantly improved softness (as measured by tensile testing) compared to the shampoo of Comparative Experiment VA3, which contains a commercially available dimethicone emulsion.

[0298] [Example A3-b] Cosmetic composition - Shampoo The following examples represent cosmetic compositions containing emulsion B3.

[0299] The activity content of organopolysiloxane in the cosmetic composition is 1.0%.

[0300] The composition of the shampoo is summarized in Table 10.

[0301] Preparation Instructions Disperse 0.30 parts guar hydroxypropyltrimonium chloride in water. Slowly stir 41.50 parts sodium laureth sulfate and gradually heat the mixture to 75°C. During heating, add 0.20 parts PEG-150 distearate at 50°C and 0.50 parts glycol distearate at 65°C. Then cool the mixture. When it reaches 35°C, add phenoxyethanol, 0.90 parts ethylhexylglycerin and the emulsion corresponding to the example, and stir the mixture for 5 minutes. Finally, add 13.4 parts cocamidopropyl betaine and stir the mixture for a further 10 minutes.

[0302] According to panel tests, damaged hair treated with the shampoo of Example A3-b was softer than untreated damaged hair.

[0303] [Table 10]

[0304] [Example A3-c] Cosmetic composition - Shampoo The following examples represent cosmetic compositions containing emulsion B3.

[0305] The activity content of organopolysiloxane in the cosmetic composition is 1.0%.

[0306] The composition of the shampoo is summarized in Table 11.

[0307] [Table 11]

[0308] According to panel tests, damaged hair treated with the shampoo of Example A3-c was softer than untreated damaged hair.

[0309] [Examples A1-b and A2-b] Rinse-off conditioner The following examples represent cosmetic compositions A1-b and A2-b, which contain emulsions B-1b and B2. The activity content of organopolysiloxane in the cosmetic compositions is 2.0%.

[0310] The composition of the rinse-off conditioner is summarized in Table 12.

[0311] Preparation Instructions Heat the initial water mixture to 75°C while stirring. Add 1.1 parts hydroxyethylcellulose. When the mixture reaches 65°C, add 0.5 parts stearamidopropyl dimethylamine, 1.0 part polysorbate 80, 3.0 parts stearyl alcohol, 2.0 parts cetyl alcohol, and 1.8 parts behentrimonium chloride. Stir the mixture until it reaches 75°C to dissolve the components. Then, cool the mixture. During the cooling process, add 0.2 parts citric acid and 0.2 parts tetrasodium EDTA. At 35°C, add 0.9 parts phenoxyethanol and ethylhexylglycerin. Continue stirring and add the emulsion from the examples. Homogenize the composition by stirring for 15 minutes.

[0312] [Table 12]

[0313] 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, Schuelke & Mayr

[0314] Damaged hair treated with rinse-off conditioner from Examples A1-b and A2-b was softer than untreated damaged hair, according to panel tests.

[0315] [Example A4] Cosmetic composition: Nourishing styling spray The following examples represent cosmetic composition A4 of the present invention, which includes emulsion B1-a.

[0316] To prepare cosmetic composition A4, 9.3 g of emulsion B1-a is diluted with 90.7 g of water. The active content of organopolysiloxane in the cosmetic composition is 3.0%.

[0317] [Comparative Example VA4] Cosmetic composition: Nourishing styling spray Comparative experiment VA4 represents a non-inventive cosmetic composition containing an aqueous dispersion V2 of a pre-crosslinked organopolysiloxane.

[0318] The procedure of Example A4 was repeated with the modification of using pre-crosslinked non-inventive emulsion V2 to prepare the cosmetic composition for comparative experiment VA4. 8.7 g of emulsion V2 was diluted with 91.3 g of water. The active content of organopolysiloxane in the non-inventive cosmetic composition VA4 was 3.0%.

[0319] <Comparison experiment of invention example A4 (nutritional styling spray) with VA4> To investigate the shaping properties of nourishing styling sprays on hair, curls were created as described in the chapter on "Curl Retention in High Humidity," and 0.2g of each spray was applied to determine curl retention.

[0320] [Table 13]

[0321] As a result, the curled strands of hair treated with the styling spray of the present invention in Example A4 showed 73% curl retention after 7 hours. The curled strands of hair were comfortably soft and retained their shape even after combing. It was possible to comb the curled strands of hair without resistance. For the curled strands of hair treated with the spray from the non-inventive comparative example VA4, a curl retention rate of 30% was determined. Therefore, curl retention at high humidity was significantly lower for these curled strands of hair than for the curled strands of hair treated with the spray of the inventive example A4.

Claims

1. An aqueous dispersion containing a pre-crosslinked organopolysiloxane, The aforementioned pre-crosslinked organopolysiloxane has at least one structural unit on average according to the following general formula Siro ２／２ —Y—SIR ２／２ (I) and the units of the following formulas R ２ Yes ２／２ (II) [In the formula, Y represents the base of the following equation, -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 - R may be the same or different, and represents a monovalent SiC-bonded hydrocarbon group having 1 to 18 carbon atoms and potentially containing one or more heteroatoms from the group consisting of N, P, S, O, and halogens. R ２ This may be the same or different, and represents a divalent straight-chain or branched hydrocarbon group having 3 to 18 carbon atoms bonded by SiC. R ３ These may be the same or different, and represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an acyl group. R ４ This may be the same or different, and represents a divalent hydrocarbon group having 1 to 6 carbon atoms. k1 is 0, 1, 2, or 3. k2 is 0, 1, 2, or 3. x is 0, 1, 2, 3, or 4. a is 0, 1, 2, 3 or 4, b is an integer between 0 and 500, Z １ is -OH, H, or -NHR ３ This represents, Z ２ is -OH, -H, or -NHR ３ [This represents...] An aqueous dispersion containing the above.

2. The aqueous dispersion according to claim 1, characterized in that the pre-crosslinked organopolysiloxane contains siloxane units of the following formula. R ３－ｄ (OR １ ) ｄ SiO １／２ (III) [In the formula, R may be the same or different, and represents a monovalent SiC-bonded hydrocarbon group having 1 to 18 carbon atoms and potentially containing one or more heteroatoms from the group consisting of N, P, S, O, and halogens. R １ This may be the same or different, and represents an alkyl group having a hydrogen atom or 1 to 18 carbon atoms, which may be interposed by one or more distinct oxygen atoms. d is either 0 or 1.

3. The aqueous dispersion according to claim 1 or 2, characterized in that Y is a base of the following 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 - [In the formula, R may be the same or different, and represents a monovalent SiC-bonded hydrocarbon group having 1 to 18 carbon atoms and potentially containing one or more heteroatoms from the group consisting of N, P, S, O, and halogens. x is either 0 or 1, b is an integer between 0 and 500, R ２ is, formula - (CH ２ ) ３ - or -CH ２ -CH(CH ３ ) - CH ２ It is the basis of...

4. A process for producing an aqueous dispersion of pre-crosslinked organopolysiloxanes, The aqueous dispersion of the aminoorganopolysiloxane (1) of the following formula is (R １ O) ｄ A ｅ R ３－ｄ－ｅ SiO(SiARO) ｐ (SiR ２ O) ｑ SiR ３－ｄ－ｅ A ｅ (OR １ ) ｄ (IV) [In the formula, A is an amino group in the following general formula: -R ２ -[NR ３ -R ４ -] ｘ NR ３ ２ R may be the same or different, and represents a monovalent SiC-bonded hydrocarbon group having 1 to 18 carbon atoms and potentially containing one or more heteroatoms from the group consisting of N, P, S, O, and halogens. R １ This may be the same or different, and represents an alkyl group having a hydrogen atom or 1 to 18 carbon atoms, which may be interposed by one or more distinct oxygen atoms. R ２ This may be the same or different, and represents a divalent straight-chain or branched hydrocarbon group having 3 to 18 carbon atoms bonded by SiC. R ３ These may be the same or different, and represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an acyl group. R ４ This may be the same or different, and represents a divalent hydrocarbon group having 1 to 6 carbon atoms. d is either 0 or 1. e is either 0 or 1. p is an integer between 1 and 1000. q is an integer between 0 and 2000, x is 0, 1, 2, 3, or 4. A manufacturing process involving reaction with the reactive ester (2) shown in the following 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 -NR ３ -OC-[C(Z ２ )(H)] ｋ２ -[C(Z １ )(H)] ｋ１ -CO ２ -R ５ (V) [In the formula, R, R ２ , R ３ , and R ４ As defined above, R ５ This represents an oxygen-bonded saturated or unsaturated, linear or branched monovalent hydrocarbon group, which may be identical or different, have 1 to 20 carbon atoms per group, and may contain one or more heteroatoms from the group consisting of N, P, S, O and halogens. k1 is 0, 1, 2, or 3. k2 is 0, 1, 2, or 3. a is 0, 1, 2, 3 or 4, b is an integer between 0 and 500, Z １ is -OH, -H, or -NHR ３ This represents, Z ２ is -OH, -H, or -NHR ３ [This represents...]

5. The process according to claim 4, characterized in that A is an amino group of the following formula. -R ２ -[NH-CH ２ CH ２ -] ｘ NH ２ [In the formula, x is either 0 or 1, R ２ is, formula - (CH ２ ) ３ - or -CH ２ -CH(CH ３ ) - CH ２ It is the basis of...

6. The process according to claim 4 or 5, characterized in that the reactive ester (2) is an oxalamido-ethyl-ester-terminated organopolysiloxane.

7. The following general formulas have an average of at least one structural unit Siro ２／２ —Y—SIR ２／２ (I) and the units of the following formulas R ２ Yes ２／２ (II) [In the formula, Y represents the base of the following equation, -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 - R may be the same or different, and represents a monovalent SiC-bonded hydrocarbon group having 1 to 18 carbon atoms and potentially containing one or more heteroatoms from the group consisting of N, P, S, O, and halogens. R ２ This may be the same or different, and represents a divalent straight-chain or branched hydrocarbon group having 3 to 18 carbon atoms bonded by SiC. R ３ These may be the same or different, and represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an acyl group. R ４ This may be the same or different, and represents a divalent hydrocarbon group having 1 to 6 carbon atoms. k1 is 0, 1, 2, or 3. k2 is 0, 1, 2, or 3. x is 0, 1, 2, 3, or 4. a is 0, 1, 2, 3 or 4, b is an integer between 0 and 500, Z １ is -OH, H, or -NHR ３ This represents, Z ２ is -OH, -H, or -NHR ３ [This represents...] Pre-crosslinked organopolysiloxanes, including

8. The pre-crosslinked organopolysiloxane according to claim 7, characterized by containing siloxane units of the following formula. R ３－ｄ (OR １ ) ｄ SiO １／２ (III) [In the formula, R may be the same or different, and represents a monovalent SiC-bonded hydrocarbon group having 1 to 18 carbon atoms and potentially containing one or more heteroatoms from the group consisting of N, P, S, O, and halogens. R １ This may be the same or different, and represents an alkyl group having a hydrogen atom or 1 to 18 carbon atoms, which may be interposed by one or more distinct oxygen atoms. d is either 0 or 1.

9. A manufacturing process for pre-crosslinked organopolysiloxanes, The aminoorganopolysiloxane in the following formula (R １ O) ｄ A ｅ R ３－ｄ－ｅ SiO(SiARO) ｐ (SiR ２ O) ｑ SiR ３－ｄ－ｅ A ｅ (OR １ ) ｄ (IV) React with the reactive ester of the following 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 -NR ３ -OC-[C(Z ２ )(H)] ｋ２ -[C(Z １ )(H)] ｋ１ -CO ２ -R ５ (V) [In the formula, A is an amino group in the following general formula: -R ２ -[NR ３ -R ４ -] ｘ NR ３ ２ R may be the same or different, and represents a monovalent SiC-bonded hydrocarbon group having 1 to 18 carbon atoms and potentially containing one or more heteroatoms from the group consisting of N, P, S, O, and halogens. R １ This may be the same or different, and represents an alkyl group having a hydrogen atom or 1 to 18 carbon atoms, which may be interposed by one or more distinct oxygen atoms. R ２ This may be the same or different, and represents a divalent straight-chain or branched hydrocarbon group having 3 to 18 carbon atoms bonded by SiC. R ３ These may be the same or different, and represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an acyl group. R ４ This may be the same or different, and represents a divalent hydrocarbon group having 1 to 6 carbon atoms. R ５ This represents an oxygen-bonded saturated or unsaturated, linear or branched monovalent hydrocarbon group, which may be identical or different, have 1 to 20 carbon atoms per group, and may contain one or more heteroatoms from the group consisting of N, P, S, O and halogens. d is either 0 or 1. e is either 0 or 1. p is an integer between 1 and 1000. q is an integer between 0 and 2000, x is 0, 1, 2, 3, or 4. k1 is 0, 1, 2, or 3. k2 is 0, 1, 2, or 3. a is 0, 1, 2, 3 or 4, b is an integer between 0 and 500, Z １ is -OH, -H, or -NHR ３ This represents, Z ２ is -OH, -H, or -NHR ３ [This represents...] The manufacturing process is characterized by subsequently emulsifying the obtained pre-crosslinked organopolysiloxane in water, with optional emulsification.

10. A cosmetic composition comprising an aqueous dispersion of a pre-crosslinked organopolysiloxane according to claim 1 or 2, or a pre-crosslinked organopolysiloxane according to claim 7 or 8.

11. The cosmetic composition according to claim 10, characterized by containing a conditioning agent.

12. Use of the cosmetic composition according to claim 10 for treating keratin fibers.

13. Use of the cosmetic composition according to claim 10 for conditioning keratin fibers.

14. The use according to claim 12, characterized in that the keratin fiber is hair.

15. A process for treating keratin-containing fibers by applying the cosmetic composition according to claim 10 to the keratin fibers and then optionally rinsing them with water.

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