Use of polycarboxylic acid compounds for treating amino acid-based fibrous substrates, especially hair

Abstract

The present invention relates to polycarboxylic acid compounds, aqueous compositions comprising the same, uses of cosmetic compositions, especially hair care compositions comprising the same, and their use for treating hair, and methods for treating hair comprising using the cosmetic compositions.

Description

Technical Field

[0001] The present invention relates to polycarboxylic acid compounds, aqueous compositions comprising the same, cosmetic compositions comprising the same, in particular hair care compositions, for use in treating hair, and methods for treating amino acid-based fibrous substrates, in particular hair, comprising using the cosmetic compositions. Background Art

[0002] Hair can be generally straight, wavy, curly, curled or twisted. Human hair includes three major morphological components, namely the cuticle (the outermost thin shell of several concentric layers), the cortex (the body of the hair), and in the case of higher diameter hair, the medulla (the thin central core). The cuticle and cortex provide the mechanical properties of the hair strand, i.e., its tendency to be wavy, curly or curled. A straight hair strand may resemble a rod with a circular cross section, a wavy hair strand may appear to be compressed into an oval cross section, a curly strand may appear to be further compressed into an elongated elliptical cross section, and a curly hair strand may also be flatter in cross section.

[0003] The major component of hair is the cross-linked α-helical protein keratin. Keratin is an intermediate filament protein found particularly in epithelial cells such as human skin and hair, wool, feathers, and nails. The α-helical type I and II keratin intermediate filament proteins (KIFs) with a molecular weight of approximately 45-60 kDa are embedded in an amorphous matrix of keratin-associated proteins (KAPs) with a molecular weight between 20-30 kDa (MA Rogers, L. Langbein, S. Praetzel-Wunder, H. Winter, J. Schweizer, J. Int Rev Cytol. 2006; 251: 209-6); both intramolecular and intermolecular disulfide bonds provided by cystine contribute to the cytoskeletal protein network that maintains the cell scaffold. In addition to disulfide cross-links, ionic bonds or salt bridges that pair the various amino acids found in hair proteins also contribute to the appearance of the hair strand.

[0004] Traditionally, aldehyde-based formulations have been developed for permanent hair shaping and hair strengthening. Formaldehyde is most commonly used for the so-called Brazilian keratin shaping process (US 2012-0031420). The basic principle is the cross-linking reaction between formaldehyde and keratin-based amino and amido groups (H. Puchtler, Histochemistry, 82 (1985), pp. 201-204) or between formaldehyde and -SH groups (US 2009-0211593).

[0005] Alternatively, US9144537 and US2015 / 0328102 describe salts of maleic acid with diamines or unsaturated amines for hair strengthening and color protection purposes.

[0006] Further, it is known in the art that hair can be treated with functionalized silicones that provide one or more cosmetic benefits such as conditioning, shine and UV protection and color retention. Typically, these silicones are physically deposited on the fiber surface (cuticle) and are therefore responsible for the appearance of the hair. They can be partially or completely removed by repeated washing processes. Although the deposited silicones greatly improve the surface properties of the hair, namely smoothness and friction, they do not substantially affect the shape, mechanical properties and release properties of the hair.

[0007] Esters of diacetyltartaric acid and glycerol are known as food additives (WO2017071663, JP2017063619, CN105815536, TW2011143630, JPH07170904). These diacetyltartaric acid glycerides are also known in encapsulation (CN106490571) and in plasticizer formulations (CN104892976). Mixed esters of tartaric acid with fatty acids and glycerol are also known as food additives (JP2009273441, GB924050, GB1087783, GB881714). They are also proposed for other applications, namely resins (KR20040054557), topcoats (JPH04353600, GB388367), alkyd resin formulations (GB954086, GB498818), lubricants (GB643025), photographs (GB577998) and cosmetics (EP2363387). It is proposed to use tartaric acid glycerides, namely for resins (GB320041, GB479905), for fiber modification (GB497846, GB541047) or as intermediates for emulsifiers (WO2010017651).

[0008] JP2001114647 and US5854319 describe Si-OC linked silicone-amino acid condensates for cosmetic applications. DE10036522 and DE10036532 describe Si-C linked amino acid modified silicones. WO2012084826 and US6664342 describe aspartic acid modified silicones. JP2004269459 describes aspartic acid modified silicones with cyclic amino acid structures.

[0009] Alternative hair treatment methods are available, but these often involve the use of harsh and regulated substances.

[0010] There is therefore a continuing need for effective compounds for treating hair which can be synthesized in a simple and cost-effective manner, which are easy to formulate and easy to use, which give rise to long-term stable formulations even in the presence of other performance ingredients and which can be used for strengthening the hair, for hair color maintenance, for hair color enhancement, for hair color deepening, for hair color protection, for hair shaping, i.e. hair curling and straightening, for hair conditioning, for hair smoothening or softening, for hair straightening, and for improving the manageability of the hair, in particular for improving the combability of the hair. In particular, the benefits with regard to maintaining artificial hair color without the use of strongly irritating auxiliaries should be achieved.

[0011] The inventors have found that certain polyorganosiloxanes A) and / or certain organic compounds B) carrying specific functional groups are suitable for meeting the above needs. The inventors have found that said polyorganosiloxanes A) and / or organic compounds B) and aqueous compositions comprising them can be synthesized in a simple and cost-effective manner, are easy to formulate and use, and can be used to treat hair, in particular for strengthening hair, for hair color maintenance, for hair color enhancement, for hair color deepening, hair color protection, for hair shaping, i.e. hair curling and straightening, for hair conditioning, for hair smoothing or softening, for hair straightening, and for improving the manageability of hair, in particular for improving the combability of hair. In particular, the use of said polyorganosiloxanes A) and / or said organic compounds B) avoids the use of strong irritating adjuvants. Summary of the invention

[0012] According to the present invention, there is provided the use of the following substances in a color and shape treatment of hair, preferably in a color treatment of hair:

[0013] A polyorganosiloxane of formula (A) having an average number of 2 to 1000 siloxy units selected from siloxy groups having the formula:

[0014]

[0015] in

[0016] R is selected from R 1 and R F ,in

[0017] R 1 are selected from organic groups bonded to the silicon atom via a carbon atom, and the two groups R 1 Can form a bridging group between two silicon atoms,

[0018] R F Select from different R 1and is bonded to the silicon atom via a carbon atom, and R F Contains at least one functional group F selected from the following:

[0019] –O–C(O)–R 3 –C(O)OH, and

[0020] –NR 4 –C(O)–R 3 –C(O)OH, and

[0021] wherein the group F is bonded to a carbon atom, wherein

[0022] R 3 is selected from a single bond or an optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms, optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, a tertiary amino group and quaternary ammonium groups

[0023] The condition is R 3 is not –CH=CH–, and

[0024] R 4 is selected from hydrogen or an optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms, optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, a tertiary amino group and quaternary ammonium groups

[0025] Or a compound of formula (B):

[0026] R 2 (–F) 2-18 (B)

[0027] in

[0028] R 2 is selected from optionally substituted divalent to octavalent hydrocarbon groups having up to 100 carbon atoms and which may optionally contain one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, a tertiary amino group and quaternary ammonium groups and F is as defined above,

[0029] or a salt of the polyorganosiloxane of formula (A) or the compound of formula (B).

[0030] Hair color treatments in the present invention preferably include all kinds of treatments involving hair coloring or hair color, such as applying hair color, deepening, enhancing or protecting hair color, maintaining hair color, etc. Hair shape treatments in the present invention shall mean all kinds of treatments which have an effect on the hair shape, in particular hair strengthening, hair curling, hair straightening, which generally improves the manageability of the hair, as outlined in more detail below.

[0031] Salts of the polyorganosiloxane of formula (A) or the compound of formula (B) of the present invention may include, for example, alkali metal salts such as sodium or potassium salts, alkaline earth metal salts such as calcium, magnesium or strontium salts, or aluminum or zinc salts, or derived from ammonia or from organic primary, secondary or tertiary amines having 1 to 20 carbon atoms such as ethylamine, diethylamine, triethylamine, ethyldiisopropylamine, monoethanolamine, diethanolamine, triethanolamine, dicyclohexylamine, dimethylaminoethanol, diethylaminoethanol, tris(hydroxymethyl)aminomethane, procaine, dibenzylamine, N-methylmorpholine, arginine, The salts of the compounds of the present invention can be prepared in particular by reacting the compounds of the present invention with a suitable base via a variety of known methods.

[0032] The group F has a formula selected from the following:

[0033] *–O–C(O)–R 3 –C(O)OH, and

[0034] *–NR 1 –C(O)–R 3 –C(O)OH,

[0035] The bond marked with an asterisk is bound to R 2 of carbon atoms.

[0036] The group F can also be depicted as:

[0037]

[0038] The dotted line connects to R 2 of carbon atoms.

[0039] Preferred groups F are *-O-C(O)-R 3–C(O)OH.

[0040] In R 3 In the case of an asymmetric structure, if the following dicarboxylic acid

[0041] and providing a portion R of compound (B) 2 Or if the compound of the polyorganosiloxane part of the polyorganosiloxane (A) is reacted, two isomers may be formed, and such isomers are included in the scope of the present invention even if they are not explicitly mentioned.

[0042] In a preferred embodiment of the present invention, the group R 2 , R 3 and R 4 The optional substituents of are selected from hydroxy, amino and halogen, preferably hydroxy and amino, and the number of substituents may be up to 5, preferably 1-4.

[0043] In a preferred embodiment of the present invention, R 4 Selected from hydrogen; n-, iso- or tert-C1-C 22 -alkyl, C2-C 22 -alkoxyalkyl, C5-C 30 -Cycloalkyl, C6-C 30 -Aryl, C6-C 30 -Aryl (C1-C6) alkyl, C6-C 30 -alkylaryl, C2-C 22 -alkenyl, C2-C 22 -alkenyloxyalkyl, which may optionally be substituted by hydroxy and halogen, and which may optionally contain one or more ether groups (-O-); preferably hydrogen or n-, iso- or tert-C1-C 22 -alkyl. The most preferred R 1 For hydrogen.

[0044] In a preferred embodiment of the present invention, R 2 is selected from divalent to decavalent, more preferably divalent to hexavalent, even more preferably divalent hydrocarbon groups (preferably aliphatic) having 2-30 carbon atoms, more preferably 2-20 carbon atoms, even more preferably 2-15 carbon atoms and optionally containing one or more groups selected from -O-, -NH-, -C(O)-, -C(S)-, and wherein R 2 Optionally substituted with one or more hydroxy groups.

[0045] In a preferred embodiment of the present invention, R 2 It has a valence of 2-18, preferably 2-12, more preferably 2-10, and still more preferably 2-8, such as 2-6, in particular 2 or 3 or 4.

[0046] In a preferred embodiment of the present invention, R 2 Selected from:

[0047] - a divalent to 18-valent, preferably a divalent to hexavalent, more preferably a divalent hydrocarbon radical derived from an aliphatic polyol having more than three carbon atoms such as alkane di-, tri- and tetraols such as 1,6-hexanediol, trimethylolpropane, and pentaerythritol,

[0048] - a divalent to octavalent, preferably divalent to hexavalent, more preferably a divalent hydrocarbon radical comprising at least one ether group and optionally having one or more hydroxyl substituents, which is derived from a polyalkylene oxide such as a polyether based on ethylene oxide, propylene oxide and / or butylene oxide, for example derived from a polyethylene glycol such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, etc., or derived from a polypropylene glycol such as propylene glycol dipropylene glycol (e.g., derived from 2,2′-oxydi-1-propanol, 1,1′-oxydi-2-propanol, and 2-(2-hydroxypropoxy)-1-propanol), tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, and the like, derived from copolyethers based on mixed ethylene oxide and butylene oxide, derived from copolyethers based on mixed propylene oxide and butylene oxide, and derived from copolyethers based on mixed ethylene oxide and propylene oxide and butylene oxide,

[0049] - a divalent to 18-valent, preferably divalent to hexavalent, more preferably a divalent hydrocarbon radical, optionally comprising at least one ether group and optionally having one or more hydroxyl substituents, derived from oligoglycerols such as diglycerol, triglycerol, tetraglycerol, pentaglycerol, hexaglycerol, and statistically distributed glycerol oligomeric condensation products, for example

[0050] - a divalent to 18-valent, preferably a divalent to hexavalent hydrocarbon group, more preferably a divalent hydrocarbon group, which is derived from a compound including at least one glycidyloxy group, such as diglycidyl ether, glycerol diglycidyl ether, and glycerol triglycidyl ether,

[0051] - a divalent to 18-valent, preferably a divalent to hexavalent, more preferably a divalent hydrocarbon radical comprising at least one ether group and optionally having one or more hydroxyl substituents, which is derived from a polyol alkylene oxide addition product, for example an addition product of ethylene oxide and / or propylene oxide on a polyol such as ethylene glycol, 1,2-propylene glycol, glycerol, trimethylolpropane, pentaerythritol, sorbitol and sucrose,

[0052] a divalent to octavalent, preferably divalent to hexavalent, more preferably divalent hydrocarbon radical comprising at least one ether group and optionally having one or more hydroxyl and / or amino substituents, which is derived from polyamine alkylene oxide addition products, such as addition products of ethylene oxide and / or propylene oxide on ethylenediamine, diethylenetriamine, or alkylene oxide addition products derived from ethanolamine,

[0053] a divalent to octavalent, preferably a divalent to hexavalent, more preferably a divalent hydrocarbon radical comprising at least one ester group and having one or more hydroxyl substituents, derived, for example, from a polyester, preferably from the condensation of a divalent to hexavalent carboxylic acid, such as maleic acid, succinic acid, adipic acid, sebacic acid, itaconic acid, tartaric acid, trimellitic acid, with an alkylene oxide, such as ethylene oxide, propylene oxide, butylene oxide, and a compound comprising at least one glycidyloxy group, such as glycidol, diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, in particular the condensation products of succinic acid, maleic acid and tartaric acid onto glycerol diglycidyl ether,

[0054] -Further R 2 Preferably denotes a polyalkyleneoxy group, which preferably has the following general formula:

[0055] -[CH2CH2O] q1 -[CH2CH(CH3)O] r1 -[CH2CH(C2H5)O] s1 -{[CH2CH2] q2 -[CH2CH(CH3)] r2 -[CH2CH(C2H5)] s2}-

[0056] in

[0057] q1=0-49, preferably 0-10, more preferably 1-10, even more preferably 1-5,

[0058] r1=0-32, preferably 0-10, more preferably 1-10, even more preferably 1-5,

[0059] s1=0-24, preferably 0-10, more preferably 1-10, even more preferably 1-5,

[0060] q2=0 or 1,

[0061] r2=0 or 1,

[0062] s2 = 0 or 1, and

[0063] ∑(q2+r2+s2)=1,

[0064] Provided that the sum of carbon atoms in such polyalkylene oxide groups is 2-100, preferably 2-50, more preferably 2-30, even more preferably 2-20, especially 2-15,

[0065] - a divalent hydrocarbon radical derived from oligoglycerol of the following general formula:

[0066] -[CH2CH(R 7 )CH2O] t1 -[CH2CH(R 7 )CH2)] t2 -

[0067] in

[0068] t1=0-32, preferably 0-10, more preferably 1-10, even more preferably 1-5, especially 1 and 2,

[0069] t2=1,

[0070] R 7 =OH or F, wherein F is as defined above, preferably -O-C(O)-R 3 –C(O)OH,

[0071] Provided that the sum of carbon atoms is 2-100, preferably 2-50, more preferably 2-30, even more preferably 2-20, especially 2-15, and

[0072] - a divalent hydrocarbon radical comprising at least one ester group of the following general formula:

[0073] -[CH2CH2O] q1 -R 8 -[CH2CH2O] q1 -[CH2CH2] q2 -

[0074] Where q1 may be the same or different and is as defined above and q2 = 1

[0075] and

[0076] -[CH2CH(R 7 )CH2O] t1 -R 8 -[CH2CH(R 7 )CH2O] t1 -[CH2CH(R 7 )CH2)] t2 -

[0077] Where t1, t2 and R 7 As defined above, and

[0078] R 8Selected from -C(O)C(O)O-; -C(O)(CH2) 1-8 C(O)O-, which is derived, for example, from succinic acid, adipic acid, sebaceous acid; or -C(O)(C6H4)C(O)O-, i.e., it is derived from phthalic acid and terephthalic acid; -C(O)CH=CHC(O)O-; -C(O)C(=CH2)-CH2C(O)O-; -C(O)CH(OH)CH(OH)C(O)O-,

[0079] The condition is R 2 The sum of carbon atoms in is 2-100, preferably 2-50, more preferably 2-30, even more preferably 2-20, especially 2-15.

[0080] In a preferred embodiment of the present invention, R 2 Contains one or more, for example 1 to 5, groups —O—. These groups —O— are preferably ether groups, but can also form ester groups together with carbonyl groups. Preferably, the group R 2 Substituted with one or more hydroxy groups.

[0081] In a preferred embodiment of the invention, the compounds according to the invention have the following formula:

[0082]

[0083] Where R 5 is selected from hydroxyl or F, wherein F is as defined above, provided that R 5 At least two of them are F.

[0084] In a preferred embodiment of the invention, the compounds according to the invention have the following formula:

[0085]

[0086] Where R 9 One of them is hydroxyl and R 9 One of the following groups

[0087]

[0088] and wherein F is as defined above, and the dashed line is a bond to the carbon atom.

[0089] In a preferred embodiment of the present invention, the compound according to the present invention is a mixture of the following two isomers:

[0090]

[0091] wherein F is as defined above.

[0092] Examples of precursors of the compounds according to the invention comprising a glycerol moiety are the glycidyl-functional Denacol types EX-313, EX-314, EX-421, EX 512, EX 521 (Nagase).

[0093] Examples of precursors of compounds according to the invention comprising trimethylolpropane, pentaerythritol and neopentyl glycol moieties are the glycidyl-functional Denacol types EX-321, EX-411 and EX-211 (Nagase).

[0094] In a preferred embodiment of the invention, the compounds according to the invention have the following formula:

[0095]

[0096] wherein x is 1-10, preferably 1-5, and F is as defined above.

[0097] Examples of precursors of compounds according to the invention comprising a propylene glycol moiety are the glycidyl-functional Denacol types EX-920, EX-921 (Nagase).

[0098] Examples of precursors of compounds according to the invention comprising ethylene glycol moieties are the glycidyl-functional Denacol types EX-821, EX-830, EX-832, EX-841, EX-850, EX-851, EX-861 (Nagase).

[0099] In a preferred embodiment of the present invention, R 3 is selected from a single bond and a linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 18, preferably up to 12, more preferably up to 10 carbon atoms and optionally comprising one or more radicals selected from —O—, —NH—, —C(O)—, and wherein R 3 Optionally substituted with one or more groups selected from hydroxyl groups, amino groups, and carboxyl groups.

[0100] If R 3 is an aromatic hydrocarbon group, preferably having no hydroxyl substituent, more preferably R 3 is an unsubstituted hydrocarbon group.

[0101] Preferably R 3 is selected from aliphatic groups, i.e., optionally substituted linear, cyclic or branched saturated or unsaturated hydrocarbon groups having up to 100 carbon atoms, which optionally contain one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups and quaternary ammonium groups The condition is R 3 Not –CH=CH–.

[0102] In a preferred embodiment of the present invention, R 3 Derived from a dicarboxylic acid. Here and in the context of the present invention, "derived from" shall mean, in particular, a residue which is formally formed from a compound by reacting these compounds to give the compound of the invention. For example, consider 3 Embodiments derived from dicarboxylic acids, in which case R derived from the dicarboxylic acid 3 For example, it can be obtained as follows: a polyol or polyepoxide or polyamine of the following formula:

[0103] R 2 '(–A) c

[0104] With dicarboxylic acid

[0105] react to form e.g.

[0106] R 2 '(–OH) a (–O–C(O)–R 3 –C(O)OH) b

[0107] or

[0108] R 2 '(–OH) a (–NH–C(O)–R 3 –C(O)OH) b

[0109] Wherein A is OH and / or epoxy group and / or amino group, preferably OH and / or epoxy group, preferably formula: wherein c=2-18, preferably c=2-10, more preferably c=2-8, more preferably c=2-4,

[0110] wherein b≥2 and a+b=2-18, preferably b=2-6, more preferably b=2-4, more preferably b=2, and a+b=preferably 2-8, more preferably a+b=2-6, and wherein R 2 'Each is a pair of R 2 The part that contributes to the formation of.

[0111] In a preferred embodiment of the present invention, R 3 Derived from a dicarboxylic acid of the formula:

[0112]

[0113] Where R3 As defined above, the dicarboxylic acid is, for example, an optionally substituted saturated or unsaturated aliphatic dicarboxylic acid or an aromatic dicarboxylic acid, such as oxalic acid (oxalic acid), malic acid (malonic acid), succinic acid (succinic acid), gum acid (glutaric acid), adipic acid (adipic acid), syrup acid (pimelic acid), suberic acid (suberic acid), azelaic acid (zelaic acid), sebacic acid (decanedioic acid), undecanedioic acid, dodecanedioic acid, brassic acid (tridecanedioic acid), hexadecanedioic acid, glutaconic acid (pent-2-enedioic acid), citraconic acid ((2Z)-2-methylbut-2-enedioic acid), mesaconic acid ((2E)-2-methyl-2-butenedioic acid), itaconic acid (2-methylenesuccinic acid), tartrate (2-hydroxymalonic acid), mesooxalic acid (oxomalic acid), malic acid (hydroxysuccinic acid), tartaric acid (2,3-dihydroxybutanediol acid), oxaloacetic acid (oxobutanedioic acid), aspartic acid (2-aminobutanedioic acid), α-hydroxyglucoamic acid (2-hydroxyglutaric acid), arabinonic acid (2,3,4-trihydroxyglutaric acid), acetone dicarboxylic acid (3-oxoglutaric acid), α-ketoglucoamic acid (2-oxoglutaric acid), glutamic acid (2-aminoglutaric acid), diaminosyrup ((2R,6S)-2,6-diaminopimelic acid), saccharic acid ((2S,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid), phthalic acid (benzene-1,2-dicarboxylic acid), isophthalic acid (benzene-1,3-dicarboxylic acid), terephthalic acid ((benzene-1,3-dicarboxylic acid)), biphenylcarboxylic acid (2-(2-carboxyphenyl)benzoic acid), 2,6-naphthalene dicarboxylic acid, norbornene dicarboxylic acid, norbornane dicarboxylic acid; and trimellitic acid; or R 3 Derived from aliphatic or aromatic tricarboxylic acids, wherein R 3 Substituted with a carboxyl group (COOH), such as citric acid (2-hydroxypropane-1,2,3-tricarboxylic acid), isocitric acid (1-hydroxypropane-1,2,3-tricarboxylic acid), aconitic acid ((cis or trans-prop-1-ene-1,2,3-tricarboxylic acid), propane-1,2,3-tricarboxylic acid, trimesic acid (benzene-1,3,5-tricarboxylic acid). Preferred dicarboxylic acids include: succinic acid; adipic acid; itaconic acid; tartaric acid; carboxylic anhydrides such as maleic anhydride and succinic anhydride with amino acids and amino acids Derivatives such as the reaction products of β-alanine and asparagine, i.e., N-acetylaspartic acid, N-maleyl-β-alanine ((E)-4-(2-carboxyethylamino)-4-oxo-but-2-enoic acid), N-maleyl-asparagine (4-amino-2-[[(E)-4-hydroxy-4-oxo-but-2-enoyl]amino]-4-oxo-butyric acid), etc. As mentioned above, asymmetric dicarboxylic acids may result in the formation of isomers, all of which are included within the scope of the present invention.

[0114] Most preferred for hair color deepening are succinic acid and tartaric acid. Most preferred for hair color retention (lower color loss values) are succinic acid, tartaric acid, N-acetylaspartic acid and N-maleyl-β-alanine ((E)-4-(2-carboxyethylamino)-4-oxo-but-2-enoic acid).

[0115] It is also possible to use anhydrides of such dicarboxylic acids, such as succinic anhydride, itaconic anhydride, etc., for example with the formula R as defined above. 2 '(–A) c The hydroxyl and / or amino functional compounds are reacted.

[0116] In a preferred embodiment of the present invention, F is selected from the following formula:

[0117]

[0118]

[0119]

[0120] wherein the dotted line in the above formula represents a bond to the oxygen atom, and wherein at least two groups F are present.

[0121] In a further preferred embodiment of the present invention, R 2 Not derived from carbohydrates (sugars), such as monosaccharides, disaccharides, oligosaccharides, and polysaccharides, or sugar alcohols. Carbohydrates or sugars are biological molecules composed of carbon (C), hydrogen (H), and oxygen (O) atoms, usually with a 2:1 hydrogen-oxygen atomic ratio (as in water) and thus have the empirical formula C m (H2O) n (where m may be different from n). They also include deoxyribose and structurally particularly include aldoses and ketoses, residues derived therefrom are therefore preferably excluded from R 2 Sugar alcohols (also known as polyhydroxy alcohols, polyols, sugar aldehydes or glucitol) are organic compounds typically derived from sugars, which include a class of polyols and generally include, for example, ethylene glycol, glycerol, erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol, iditol, inositol, etc. (see, for example, https: / / en.wikipedia.org / wiki / Sugar_alcohol). In particular, R derived from ethylene glycol and glycerol is preferably excluded. 2 .

[0122] A further embodiment of the present invention relates to a process for producing a polyorganosiloxane of formula (A) or a (non-polyorganosiloxane) compound of formula (B) according to the present invention, which process is selected from the following processes:

[0123] (A) reacting at least one polyorganosiloxane or at least one (non-polyorganosiloxane) compound each having at least two epoxy groups with at least one di- or tricarboxylic acid compound to form a polyorganosiloxane of formula (A) or a compound of formula (B) according to the invention,

[0124] (B) reacting at least one polyorganosiloxane or at least one (non-polyorganosiloxane) compound each having at least one epoxy group with at least one di- or tricarboxylic acid compound, and subsequently reacting the reaction product with at least one anhydride compound to form a polyorganosiloxane of formula (A) or a compound of formula (B) according to the invention,

[0125] (C) reacting at least one polyorganosiloxane or at least one (non-polyorganosiloxane) compound each having at least two hydroxyl groups with at least one anhydride compound to form a polyorganosiloxane of formula (A) or a compound of formula (B) according to the invention,

[0126] (D) reacting at least one polyorganosiloxane or at least one (non-polyorganosiloxane) compound each having at least two amino groups with at least one anhydride compound to form a polyorganosiloxane of formula (A) or a compound of formula (B) according to the invention.

[0127] In a preferred embodiment of the present invention, the polyorganosiloxane (A) comprises at least two groups R F . R F Select from different R 1 and is bonded to the silicon atom via a carbon atom, and R F Contains at least one functional group F as defined above. The group R F In particular, it comprises an organic radical R substituted by at least one, preferably one, radical F as defined above. 1 ', that is, R F Preferably the group R 1 '-F, where R 1 'For which in form R 1 R has one hydrogen atom removed from the carbon atom (and replaced by F) 1 Therefore, regarding R 1 ', which can also be found in the following R 1 Preferably R 1' is selected from an optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms, optionally containing one or more groups selected from the following: -O-, -NH-, -C(O)-, -C(S)-, a tertiary amino group and quaternary ammonium groups wherein the optional substituent is preferably selected from hydroxyl groups, and the hydrocarbon group is bonded to the silicon atom via a carbon atom.

[0128] Preferably R 1 ' is selected from divalent hydrocarbon groups having up to 30 carbon atoms, preferably 1-12, more preferably 1-8, even more preferably 3-8, and especially 3-6 carbon atoms, optionally containing one or more groups selected from the following: -O-, -NH-, -C(O)-, and wherein R 1 ' is optionally substituted with one or more hydroxyl groups and R 1 'Bound to silicon via carbon atoms.

[0129] In a preferred embodiment, the group R 1 'The reaction of the epoxy group-modified silicone with the dicarboxylic acid of the following formula yields:

[0130] Where R 3 As defined above, the dicarboxylic acid is for example tartaric acid and N-acetylaspartic acid. In the most preferred embodiment, R 1 ' is obtained as follows: A glycidyloxypropyl terminated polysiloxane (derived from the reaction of SiH polysiloxane with allyl glycidyl ether) schematically shown by the following formula:

[0131]

[0132] With a dicarboxylic acid of the formula:

[0133]

[0134] React to form:

[0135]

[0136] Where R 1 ' is a group of the formula:

[0137]

[0138] The dotted lines represent the silicon atoms and the groups –O–C(O)–R 3 –bond to the oxygen atom of C(O)OH.

[0139] In a preferred embodiment, in the polyorganosiloxane (A), the polyorganosiloxane (A) comprises a group R F The molar ratio of the siloxane units to all siloxane units is 3.33-100 mol%, more preferably 5-100 mol%, even more preferably 5-50 mol%, most preferably 10-50 mol%.

[0140] In another preferred embodiment of the present invention, in the polyorganosiloxane (A), the molar proportion of branched T and Q moieties, based on the number of all siloxy units, is 0-50%, preferably 0-20%, more preferably 0-10%, in particular 0-5%, more particularly 0%.

[0141] The average number of siloxy units in polysiloxane (A) is 2 to 300, preferably 2 to 30, even more preferably 2 to 20, even more preferably 2 to 15, in particular 2 to 12, more particularly 2 to 10, even more particularly 2 to 8. The average number of siloxy units can be determined by GPC (gel permeation chromatography) using a system calibration relative to polystyrene standards.

[0142] It is within the scope of the invention to use mixtures of different polysiloxanes A) according to the invention. Mixtures of polysiloxanes A) can give rise to bimodal, trimodal and higher molecular weight distributions which differ in the siloxane chain length. Preference is given to mixtures of two polysiloxanes A) with a bimodal distribution. A preferred embodiment of the invention is a mixture comprising short-chain siloxanes with an average of 2 to 15 siloxy units and longer-chain siloxanes with an average of 16 to 30 siloxy units. Such a mixture has the advantage that, depending on the size of the molecule, different locations within the hair structure can be modified with the organosilicon polymer.

[0143] The organic group R is selected from R 1 and R F Preferably, the organic group R 1 Independently selected from

[0144] a linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 100 carbon atoms, which optionally contains a tertiary amino group selected from -O-, -NH-, -C(O)-, -C(S)- and quaternary ammonium groups and which are optionally substituted by one or more groups selected from hydroxyl, halogen (e.g. chlorine, fluorine),

[0145] A polyether radical having up to 60 carbon atoms, or two radicals R from different siloxy moieties 1a linear, cyclic or branched, saturated, unsaturated or aromatic alkanediyl hydrocarbon group having 2 to 20 carbon atoms, which is formed between two silicon atoms and is optionally substituted by one or more hydroxyl groups or halogen atoms and is bonded to the silicon via a carbon atom,

[0146] More preferably R 1 Selected from n-, iso- or tert-C1-C 22 -alkyl, C2-C 22 -alkoxyalkyl, C5-C 30 -Cycloalkyl, C6-C 30 -Aryl, C6-C 30 -Aryl (C1-C6) alkyl, C6-C 30 -alkylaryl, C2-C 22 -alkenyl, C2-C 22 -alkenyloxyalkyl, which may optionally be substituted by hydroxy and halogen, and which may optionally contain one or more ether groups (—O—),

[0147] Still more preferably, the group R 1 These include: n-, iso- or tert-C1-C2- substituted by one or more, preferably up to 5, groups selected from hydroxyl and halogen, preferably fluorine, and may contain one or more ether groups. 22 -alkyl, C2-C 22 -alkoxyalkyl, C5-C 30 -Cycloalkyl, C6-C 30 -Aryl, C6-C 30 -Aryl (C1-C6) alkyl, C6-C 30 -alkylaryl, C2-C 22 -alkenyl, C2-C 22 -alkenyloxyalkyl, i.e. H3C-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, C8H 17 - and C 10 H 21 -、H2C=CH-O-(CH2) 1-6 ; alicyclic groups, namely cyclohexylethyl, citronyl, norbornene, phenyl, tolyl, xylyl, benzyl and 2-phenylethyl; halogen (C1-C 10 ) alkyl, i.e. C f F fn+1 CH2CH2-, where f is 1-8, i.e. CF3CH2CH2-, C4F9CH2CH2-, C6F 13 CH2CH2-, C2F5–O(CF2–CF2–O) 1-10 CF2–, F[CF(CF3)–CF2–O] 1-5 –(CF2) 0-2-, C3F7-OCF(CF3)- and C3F7-OCF(CF3)-CF2-OCF(CF3)- (in this context F represents a fluorine atom), and still more preferably R 1 is selected from methyl, vinyl, phenyl, 3,3,3-trifluoropropyl, and the most preferred R 1 It is methyl.

[0148] In a preferred embodiment, the polysiloxane (A) of the present invention comprises at least two compounds of formula M F and / or D F Groups:

[0149] M F :

[0150] Where R 1 and R F As defined above.

[0151] In a further preferred embodiment, the polysiloxane (A) is selected from the following formula:

[0152]

[0153] Where R 1 and R F As defined above, and n1+n2 is 0-28, preferably 0-20, more preferably 0-15, and n2 is preferably 0,

[0154]

[0155] Where R 1 and R F As defined above, n1+n2 is 2-28, preferably 2-20, more preferably 2-15, even more preferably 5-15, and n2 ≥ 2, preferably 2-28, more preferably 2-10, even more preferably 2-5, and

[0156]

[0157] Where R 1 and R F As defined above, n1+n2 is 3-7 and n2≥2, preferably n1+n2 is 2-7, more preferably 2-5, even more preferably 3-5.

[0158] In a preferred embodiment, the polysiloxanes (A) according to the invention have a number average molecular weight Mw <2000 g / mol, preferably <1500 g / mol, more preferably <1000 g / mol, as determined by GPC using polystyrene as standard.

[0159] In a preferred embodiment of the present invention, mixtures of more than one type of polysiloxane A) according to the invention are used.

[0160] According to the invention, it is possible that the polyorganosiloxane (A) has, in addition to the functional groups R as defined above, F In addition, you may also carry a selection from different 1 and R F and contains at least one other functional organic group R selected from the following functional groups FA FA :

[0161] - an optionally substituted azetidine or azetidinium group,

[0162] - hydroxymethyl groups,

[0163] - mono-, di-, tri-hydroxy-substituted aromatic groups,

[0164] -thioesters, and

[0165] - thioether group,

[0166] - alkoxysilyl groups,

[0167] - amino group,

[0168] - an ammonium group,

[0169] -phosphonium group,

[0170] - Epoxy groups,

[0171] - carbonate groups,

[0172] - carbamate groups,

[0173] - isocyanurate groups, including blocked isocyanurate groups,

[0174] - urea groups,

[0175] -acylamino group,

[0176] - aldehyde group,

[0177] - acetal or hemiacetal groups,

[0178] - a Schiff base or an enamine group,

[0179] - zwitterionic groups,

[0180] - a carboxylic acid or carboxylate (ester / salt) group,

[0181] - sulfonic acid or sulfonate (ester / salt) group,

[0182] - a sulfate half-ester or sulfate (ester / salt) group,

[0183] - a phosphate or phosphate group,

[0184] - a phosphonate or phosphonate (ester / salt) group,

[0185] - a phosphite or phosphite group,

[0186] - xanthate / xanthate groups,

[0187] - thiosulfate group,

[0188] - mercapto groups,

[0189] - sugar groups, and

[0190] - polyether groups having up to 60 carbon atoms.

[0191] Such a functional group FA can also replace the functional group F in the polyorganosiloxane (A) and the organic compound (B), as long as in the polyorganosiloxane (A) as defined above or the formula R 2 (-F) 2-18 Preferably at least two radicals F remain in the organic compound (B).

[0192] A particularly preferred combination of functional groups F and FA is a combination of F as defined above and a mono-, di- or tri-hydroxy substituted aromatic group, for example wherein R FA Has the following structure:

[0193]

[0194] in

[0195] R 15 Independently from R as defined above 1 ', and another possibility is that R 1 ' Nitrogen-containing groups such as -NH2, -N(R 4 )2 substituted, wherein R 4 As defined above,

[0196] R 10 , R 11 , R 12 , R 13 , R 14 are identical or different from each other and are selected from hydroxyl, hydrogen and R as defined above 1 , preferably hydrogen and hydroxy, provided that 2 to 3 groups R 10 -R 14 It is hydroxyl (-OH).

[0197] A particularly preferred group RFA for

[0198] (The dashed lines are the free valences of silicon atoms).

[0199] In another preferred embodiment of the present invention, the polysiloxanes (A) according to the invention are combined with other functional polysiloxanes preferably having functional groups selected from amino, quaternary ammonium and quaternary phosphonium groups, which are combined alone or optionally with anionic polysiloxane compounds having functional groups selected from carboxylic acids / carboxyl salts, sulfonic acids / sulfonates, sulfuric acid half esters / sulfates, phosphates / phosphates, phosphonates / phosphonates, phosphites / phosphites and xanthates / xanthates. Examples of the above compounds are described in WO 2012 / 143371. It is also preferred to combine the polysiloxanes according to the invention with betaine-functional polysiloxanes. Examples of these compounds are described in WO 2012 / 143371. It is further preferred to combine the polysiloxanes according to the invention with di- and polycationic compounds of the ABA or block copolymer type. Examples of these compounds are described in WO 02 / 10257, WO 02 / 10259 and DE 10036553.

[0200] Another preferred embodiment of the present invention relates to the use of an aqueous composition comprising at least one polyorganosiloxane (A) and / or at least one compound (B) as defined above in a color and shape treatment of hair, preferably in a color treatment of hair, and preferably the aqueous composition comprises at least one polyorganosiloxane (A) or at least one compound (B). Preferably the aqueous composition comprises 0.05-30 wt.-%, preferably 0.1-20 wt.-%, preferably 0.5-15 wt.-%, more preferably 1-10 wt.-% of at least one polyorganosiloxane (A) and / or at least one compound (B), based on the total weight of the aqueous composition.

[0201] Optionally, the aqueous composition comprises at least one metal salt (in particular as described below) and optionally at least one surfactant. Further, optionally the aqueous composition comprises at least one surfactant, which is preferably selected from: cationic, nonionic, betaine and anionic surfactants, which preferably have an HLB value in the range of 1-20, preferably 7-20, more preferably 8-20. More preferably, the optional surfactant is selected from hydrocarbon-based or silicone-based emulsifiers, each different from polyorganosiloxane (A) and compound (B). The amount of the optional surfactant in the aqueous composition according to the present invention is preferably about 0.05% to about 15%, more preferably about 0.05% to about 5%, still more preferably about 0.1% to about 5%, in particular 0.1-3% by weight of the aqueous composition.

[0202] The weight ratio of the optional surfactant to the polyorganosiloxane A) is preferably at least 0.06, preferably 0.06-5, more preferably 0.06-3, even more preferably 0.1-3, in particular 0.1-1. Depending on the chemical nature of the continuous or discontinuous phase, an emulsifier having an HLB value of <7 (W / O emulsion type) or >7 (O / W emulsion type) is preferably selected.

[0203] In a preferred embodiment of the present invention, the hair treatment composition provided is a W / O emulsion (preferably a water-in-oil emulsion (W / O emulsion)).

[0204] In another preferred embodiment of the present invention, the hair treatment composition is provided as an O / W formulation (preferably an oil-in-water emulsion (O / W-emulsion).

[0205] Preferred examples of hydrocarbon-based emulsifiers are cationic, nonionic, betaine and anionic emulsifiers.

[0206] Preferred examples of cationic emulsifiers are emulsifiers based on linear or branched C8-C50, preferably C8-40, more preferably C8-C30 alkyl fatty alcohols and fatty acids containing quaternary ammonium groups or amino groups, i.e. fatty acid-based ester quaternary ammonium salts containing one or two fatty acid moieties; fatty amines and ethoxylated / propoxylated fatty amines.

[0207] Preferably, the cationic surfactant is a mono-long alkyl-tri-short alkyl quaternary ammonium salt or a di-long alkyl-di-short alkyl quaternary ammonium salt, wherein one or two alkyl substituents are selected from aliphatic groups of about 8 to about 30 carbon atoms or aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl groups having up to about 30 carbon atoms; the other alkyl groups are independently selected from aliphatic groups of about 1 to about 8 carbon atoms or aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl groups having up to about 8 carbon atoms; and the counterion is a salt-forming anion such as those selected from the following: halogen (e.g., chloride, bromide), acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfonate, sulfate, alkyl sulfate, glutamate, and alkyl sulfonate. The aliphatic group may also contain ether bonds, and other groups such as amino groups in addition to carbon and hydrogen atoms. The longer chain aliphatic groups, such as those of about 8 or more carbons, can be saturated or unsaturated.

[0208] Preferably, one alkyl group is selected from about 8 to about 30 carbon atoms, more preferably about 14 to about 26 carbon atoms, and still more preferably about 14 to 22 carbon atoms; the other alkyl groups are independently selected from -CH3, -C2H5, -C2H4OH, -CH2C6H5, and mixtures thereof; and the counterion is selected from Cl - Br - 、CH3OSO3 - , and mixtures thereof. It is believed that such mono-long alkyl quaternary ammonium salts can provide improved slipperiness on wet hair in addition to their emulsifying ability compared to poly-long alkyl quaternary ammonium salts. It is also believed that mono-long alkyl quaternary ammonium salts can provide improved hydrophobicity and slipperiness on dry hair compared to amine or amine salt cationic surfactants.

[0209] Non-limiting examples of such mono-long alkyl quaternary ammonium salt cationic surfactants include: behenyl trimethyl ammonium chloride, which is available, for example, from Clariant under the trade name Genamine KDMP, from Croda under the trade name INCROQUATT MC-80, and from Sanyo Kasei under ECONOL TM22; stearyl trimethyl ammonium chloride, which is available, for example, from Nikko Chemicals under the trade name CA-2450; cetyl trimethyl ammonium chloride, which is available, for example, from Nikko Chemicals under the trade name CA-2350; behenyl trimethyl ammonium methyl sulfate, which is available from Fei Xiang; hydrogenated tallow alkyl trimethyl ammonium chloride; stearyl dimethyl benzyl ammonium chloride; and stearyl-amidopropyl dimethyl benzyl ammonium chloride.

[0210] Preferred cationic surfactants are mono- and diester quaternary ammonium salts (quaternary ammonium salt = a compound comprising a quaternary ammonium cation) based on saturated or unsaturated fatty acids having 10 to 18 carbon atoms in the alkyl chain. Commercially available examples are Arquad PC SV-60PG and Armocare VGH70 (Akzo Nobel).

[0211] Details on cationic surfactants are disclosed in US 2013 / 259820.

[0212] The aqueous compositions of the present invention preferably include the optional cationic surfactant in an amount of about 0.05% to about 15%, preferably about 0.05% to about 5%, still more preferably about 0.1% to about 5%, especially 0.1-3% by weight of the composition.

[0213] Preferred examples of nonionic emulsifiers are emulsifiers based on linear or branched C8-C50, preferably C8-40, more preferably C8-C24 fatty alcohols and fatty acids containing ethylene oxide (EO), propylene oxide (PO) and butylene oxide (BO), and sugar-based emulsifiers, i.e., alkyl glycosides, alkoxylated fatty acid sorbitan esters and fatty acid glucamides. Another class of preferred nonionic surfactants are semi-polar amine oxides, phosphine oxides, and sulfoxides.

[0214] Preferred nonionic surfactants are ethoxylates based on saturated or unsaturated natural alcohols having 10 to 18 carbon atoms in the alkyl chain and having 5 to 80 EO units. Commercially available examples are the Genapol C, LA, V, O and T types (Clariant).

[0215] Preferred nonionic surfactants are ethoxylates based on linear or branched oxo alcohols having 11 to 17 carbon atoms in the alkyl chain and 5 to 100 EO units. Commercially available examples are the Genapol UD, OA, OX, X, LCN types (Clariant).

[0216] Preferred nonionic surfactants are block ethoxylate-propoxylates based on saturated or unsaturated alcohols having 10 to 18 carbon atoms in the alkyl chain and 2 to 20 EO units. Commercially available examples are the Genapol EP types (Clariant).

[0217] Preferred nonionic surfactants are ethoxylate-propoxylate block copolymers comprising 5-70% by weight EO units. Commercially available examples are the Genapol PF and PH types (Clariant).

[0218] Preferred nonionic surfactants are ethoxylates based on saturated or unsaturated fatty acids having 10 to 18 carbon atoms in the alkyl chain and having 5 to 100 EO units. Commercially available examples are the Genagen O and S types (Clariant).

[0219] Preferred nonionic surfactants are castor oil ethoxylates based on saturated or unsaturated fatty acids having 10 to 18 carbon atoms in the alkyl chain and having 5 to 80 EO units. Commercially available examples are the Emulsogen HCO and EL types (Clariant).

[0220] Preferred nonionic surfactants are oligoglycerols derived from saturated or unsaturated fatty acids. Preferred examples are di-, tri- or tetraglycerol derived from fatty acids, i.e. mono- or diesters of diglycerol having 10-18 carbon atoms in the alkyl chain and optionally 5-100 EO units. Commercially available examples are Hostacerine types (Clariant).

[0221] Preferred nonionic surfactants are ethoxylates based on saturated or unsaturated fatty acid sorbitan esters having 10-18 carbon atoms in the alkyl chain and 5-50 EO units attached to the sorbitan ring. A commercially available example is Emulsogen 4156 (Clariant).

[0222] Preferred nonionic surfactants are glycosides based on saturated or unsaturated alcohols having 8 to 18 carbon atoms in the alkyl chain and 1 to 10 saccharyl units. Commercially available examples are Plantacare 818up and 1200up (BASF).

[0223] Preferred nonionic surfactants are glucamides based on saturated or unsaturated fatty acids, preferably fatty acid N-methylglucamides, having 8 to 18 carbon atoms in the alkyl chain. A commercially available example is the MEGA-10 type (Avanti).

[0224] Preferred nonionic surfactants are alkanolamides based on saturated or unsaturated fatty acids, preferably ethanolamides based on fatty acids, having 8 to 18 carbon atoms in the alkyl chain. Commercially available examples are the Aminon C types (Kao).

[0225] Preferred nonionic surfactants are amine oxides based on fatty amines or fatty acid amides having 8 to 30 carbon atoms in the alkyl chain. Commercially available examples are the Tomamine AO ​​types (Air products) and the Genamineox types (Clariant).

[0226] The aqueous compositions of the present invention preferably include the optional nonionic surfactant in an amount of about 0.05% to about 15%, preferably about 0.05% to about 5%, still more preferably about 0.1% to about 5%, especially 0.1-3% by weight of the composition.

[0227] Preferred examples of betaine emulsifiers are emulsifiers based on linear or branched C8-C50, preferably C8-40, more preferably C8-C30 alkyl fatty alcohols and fatty acids containing carboxybetaine, sultaine, phosphate betaine and phosphonate betaine groups, namely cocoamidopropyl carboxybetaine.

[0228] Preferably, suitable betaine surfactants for use in compositions according to the present invention include those known for use in shampoos or other personal care cleansing. They include those surfactants broadly described as derivatives of aliphatic secondary and tertiary amines, wherein the aliphatic group may be straight or branched and wherein one of the aliphatic substituents contains about 8 to about 30 carbon atoms and one contains an anionic group such as carboxyl, sulfonate, sulfate, phosphate, or phosphonate. Exemplary amphoteric surfactants for use in formulations of the present invention include cocoamphoacetate, cocoamphodiacetate, lauroamphoacetate, lauroamphodiacetate, and mixtures thereof. They also include those surfactants broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, wherein the aliphatic group may be straight or branched and wherein one of the aliphatic substituents contains about 8 to about 30 carbon atoms and one contains an anionic group such as carboxyl, sulfonate, sulfate, phosphate, or phosphonate.

[0229] Preferred carboxybetaine surfactants are metal sarcosinates based on saturated or unsaturated fatty acids having 10 to 18 carbon atoms in the alkyl chain. A commercially available example is Medialan LD (Clariant).

[0230] Preferred carboxybetaine surfactants are amidopropyl betaines based on saturated or unsaturated fatty acids having 10 to 18 carbon atoms in the alkyl chain. A commercially available example is Genagen CAB (Clariant).

[0231] Preferred sultaine surfactants are tauramides based on saturated or unsaturated fatty acids having 10-18 carbon atoms in the alkyl chain. A commercially available example is Hostapon CT (Clariant).

[0232] Details about betaine surfactants are disclosed in US 2015 / 011449.

[0233] The compositions of the present invention preferably include the optional betaine surfactant in an amount of about 0.05% to about 15%, preferably about 0.05% to about 5%, still more preferably about 0.1% to about 5%, especially 0.1-3% by weight of the composition.

[0234] Preferred examples of anionic emulsifiers are emulsifiers based on linear or branched C8-C50, preferably C8-40, more preferably C8-C24 alkyl fatty alcohols and fatty acids containing carboxylate, sulfate, sulfonate, phosphate, and phosphonate groups, i.e. C8-C24 fatty acid carboxylates, C8-C24 fatty acid polyether carboxylates, C8-C24 fatty acid polyether sulfates, C8-C24 maleic acid addition products, C8-C24 fatty alcohol sulfates, C8-C24 sulfonates, C8-C40 phosphates containing one or two fatty acid moieties.

[0235] Preferably, the anionic surfactants suitable for use in the composition are alkyl and alkyl ether sulfates. Other suitable anionic surfactants are water-soluble salts of organic, sulfuric acid reaction products. Still other suitable anionic surfactants are the reaction products of fatty acids esterified with isethionates and neutralized with sodium hydroxide. Exemplary anionic surfactants for use in shampoo compositions include ammonium lauryl sulfate, ammonium polyethylene glycol monododecyl ether sulfate, triethylamine lauryl sulfate, triethylamine polyethylene glycol monododecyl ether sulfate, triethanolamine lauryl sulfate, triethanolamine polyethylene glycol monododecyl ether sulfate, monoethanolamine lauryl sulfate, monoethanolamine polyethylene glycol monododecyl ether sulfate, diethanolamine lauryl sulfate, diethanolamine polyethylene glycol monododecyl ether sulfate, sodium lauric acid monoglyceride sulfate, sodium lauryl sulfate, polyethylene glycol monododecyl ether sulfate Sodium alkyl ether sulfate, potassium lauryl sulfate, potassium polyethylene glycol monododecyl ether sulfate, sodium lauryl sarcosinate, sodium lauroyl sarcosinate, lauryl sarcosine, cocoyl sarcosine, ammonium cocoyl sulfate, ammonium lauroyl sulfate, sodium cocoyl sulfate, sodium lauroyl sulfate, potassium cocoyl sulfate, potassium lauryl sulfate, triethanolamine lauryl sulfate, triethanolamine lauryl sulfate, monoethanolamine cocoyl sulfate, monoethanolamine lauryl sulfate, sodium tridecylbenzene sulfonate, sodium dodecylbenzene sulfonate, sodium cocoyl isethionate and combinations thereof. In a further embodiment of the present invention, the anionic surfactant is sodium lauryl sulfate or sodium polyethylene glycol monododecyl ether sulfate (sodium lauryl ether sulfate).

[0236] Preferred anionic surfactants are polyether sulfates based on saturated or unsaturated fatty alcohols having 10 to 18 carbon atoms in the alkyl chain and having 2 to 30 EO units. Commercially available examples are the Emulsogen EPM types (Clariant).

[0237] Preferred anionic surfactants are polyether carboxylates based on saturated or unsaturated fatty alcohols having 10 to 18 carbon atoms in the alkyl chain and having 2 to 30 EO units. Commercially available examples are the Empicol types (Huntsman).

[0238] Details about anionic surfactants are disclosed in US 2015 / 011449.

[0239] Further details on soaps, particularly salts of fatty acids, for example sodium or potassium or calcium salts of C6-C22 fatty acids.

[0240] The compositions of the present invention preferably include such optional anionic surfactants in an amount of about 0.05% to about 15%, preferably about 0.05% to about 5%, still more preferably about 0.1% to about 5%, especially 0.1-3% by weight of the composition.

[0241] Further details on surfactants are disclosed in US 2009-0165812.

[0242] Preferred examples of the optional silicone-based emulsifier are cationic, nonionic, betaine and anionic emulsifiers.

[0243] Preferred examples of cationic emulsifiers are: ABA-type emulsifiers containing quaternary ammonium groups in which the EO / PO portion is connected to the terminal quaternary ammonium (including quaternary ammonium cation) end of the silicone chain (WO2009 / 042083); or quaternized emulsifiers in which the polyether portion is connected to the silicone chain in a comb-like arrangement (US2008 / 213208).

[0244] In another preferred embodiment of the invention, the hydrophilic polyhydroxy part and the lipophilic fatty alkyl or fatty alkyl ester part are attached to the silicone chain (US 2012 / 289649). A commercially available example of this type of W / O emulsifier is Silform EOF (Momentive Performance Materials).

[0245] The compositions of the present invention preferably include the optional silicone-based cationic surfactant in an amount of about 0.05% to about 15%, preferably about 0.05% to about 5%, still more preferably about 0.1% to about 5%, especially 0.1-3% by weight of the composition.

[0246] Preferred examples of silicone-based nonionic emulsifiers are ABA-type emulsifiers comprising ethylene oxide (EO), propylene oxide (PO) and butylene oxide (BO), wherein the EO / PO / BO moieties are attached to the ends of the silicone chains, or emulsifiers in which the polyether moieties are attached to the silicone chains in a comb-like arrangement. A commercially available example is SF 1540 (Momentive Performance Materials). In another preferred embodiment of the present invention, the hydrophilic polyether moiety and the lipophilic alkyl chain are attached to the silicone chain (US4698178). In another preferred embodiment of the present invention, the hydrophilic polyglycerol moiety and the alkyl or fatty alcohol ether / fatty acid ester moiety are attached to the silicone chain (US2010 / 0266651, US2009 / 0062459). In another preferred embodiment of the present invention, aminodimethicone glyceryl carbamate (Seidel, -Journal, 132, 12-2006, 30). In another preferred embodiment of the present invention, cetyl diglyceryl tris(trimethylsiloxy)silylethyl dimethicone ( http: / / ec.europa.eu / consumers / cosmetics / cosing / index.cfm? fuseaction=search.details_v2&id=92003) For W / O emulsions, the latter four types of emulsifiers are particularly preferred.

[0247] The compositions of the present invention preferably include the optional silicone-based nonionic surfactant in an amount of about 0.05% to about 15%, preferably about 0.05% to about 5%, still more preferably about 0.1% to about 5%, especially 0.1-3% by weight of the composition.

[0248] The compositions of the present invention preferably include the optional silicone-based betaine and anionic surfactant in an amount of about 0.05% to about 15%, preferably about 0.05% to about 5%, still more preferably about 0.1% to about 5%, especially 0.1-3% by weight of the composition.

[0249] It is within the scope of the present invention to use more than one surfactant to optimize formulation stability. The total amount of surfactant in the composition of the present invention preferably ranges from about 0.05% to about 15%, preferably from about 0.05% to about 5%, still more preferably from about 0.1% to about 5%, especially 0.1-3% by weight of the composition.

[0250] In a further embodiment of the present invention, the aqueous composition optionally comprises further additives, such as

[0251] a) organic diluents or solvents,

[0252] b) protein, preferably keratin,

[0253] c) emollients or fatty substances,

[0254] d) preservatives,

[0255] e) Skin protection ingredients,

[0256] f) conditioning agents,

[0257] g) an oxidizing agent,

[0258] h) a reducing agent,

[0259] i) Tannin,

[0260] j) metal salts,

[0261] k) other auxiliaries selected from the group consisting of pH regulators, thickeners, lipids, amino acids, sugars, essences, sunscreens, vitamins, pearlescent agents, gelling agents, trace elements, masking agents, antioxidants, moisturizers, anti-hair loss agents, anti-dandruff agents, propellants, ceramides, polymers, in particular film-forming polymers, fillers, mother-of-pearl, colorants, in particular pigments and dyes, and mixtures thereof,

[0262] The proviso is that oxidizing agents and reducing agents are not present simultaneously in a given formulation.

[0263] Preferably, the aqueous composition has the following composition:

[0264]

[0265]

[0266] The percentages by weight relate to the total weight of the aqueous composition.

[0267] Thinner / Solvent

[0268] The term "diluent / solvent" refers to substances other than water which can be used to dilute / dissolve the at least one polyorganosiloxane A) and / or the at least one organic compound (B) according to the invention and the other optional further ingredients as mentioned above. Suitable organic solvents are 2-methyl-1,3-propanediol, mono- and diols or ethers and esters thereof, in particular mono-C1-C3-alkyl ethers, ethanol, n-propanol, isopropanol, tert-butanol, 1-methoxypropanol, 1-ethoxypropanol and ethoxydiglycol, diols and ethers and esters thereof, 1,3-propanediol, 1,3- and 1,4-butanediol, pentanediol, hexanediol, diethylene glycol and its monomethyl and monoethyl ethers, dipropylene glycol and its monomethyl and monoethyl ethers, glycerol, diglycerol, hexanetriol, sorbitol, ethyl carbitol, benzyl alcohol, benzyloxyethanol, propylene carbonate, N-alkylpyrrolidones. In a preferred embodiment, water / ethanol, water / isopropanol, water / dipropylene glycol and water propylene glycol monomethyl ether mixtures are used. Generally, the addition of a certain amount of short-chain alcohol improves the uniformity of the formula and the penetration of the formula into the hair. Depending on the type of polymer structure and the intended application, a certain amount of acid, base and / or short-chain alcohol is required to obtain a transparent formula. Suitable acids include inorganic or organic acids, for example carboxylic acids such as acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid. Suitable bases include ammonia, alkaline hydroxides, alkaline carbonates, etc.

[0269] Protein / Keratin

[0270] The optional proteins, preferably keratin protein fractions used include hydrolyzed keratin produced by alkaline and / or enzymatic hydrolysis using methods used in the art. Keratin hydrolysates are about 1,000-3,000 molecular weight. Keratin can be derived from human or other mammalian sources such as goat hair (US 2007-0048235), hoof or horn powder (US 6,555,505). Alternatively, a "keratin protein fraction" is a purified form of keratin containing primarily, although not entirely, a unique protein group, as described in US 7,148,327. Details about keratin and keratin fractions are disclosed in US 2009-0165812.

[0271] Emollients, fatty substances

[0272] Other optional ingredients of the hair treatment formulation are one or more emollients. An "emollient" is a material that protects against moisture or irritation, softens, soothes, pliable, coats, lubricates, moisturizes, protects and / or cleanses the skin. The emollients used include one or more of the following: silicone compounds, i.e., dimethicone, cyclomethicone, preferably D5 and D6 cyclosiloxanes, dimethicone copolyols, or mixtures of cyclomethicone and dimethicone / vinyl dimethicone crosspolymers), polyols such as sorbitol, glycerol, propylene glycol, ethylene glycol, polyethylene glycol, caprylyl glycol, polypropylene glycol, 1,3-butylene glycol, hexylene glycol, isopentyl glycol, xylitol, ethylhexyl palmitate, triglycerides such as caprylic / capric triglyceride and fatty acid esters such as cetearyl isononanoate or cetyl palmitate. Details about emollients are disclosed in US 2009 / 0165812.

[0273] As fatty substances which are often referred to as oils and which are liquid at ambient temperature and which can be used in the present invention, mention may be made of: hydrocarbon-based oils of animal origin, for example perhydrosqualene; hydrocarbon-based vegetable oils, for example liquid triglycerides of fatty acids containing 4 to 10 carbon atoms, for example heptanoic or caprylic triglycerides, or sunflower oil, corn oil, soybean oil, grapeseed oil, sesame oil, almond oil, macadamia oil, castor oil, avocado oil, caprylic / capric triglycerides, jojoba oil, shea butter; linear or branched hydrocarbons of mineral or synthetic origin, for example liquid paraffin and its derivatives, vaseline, polydecene, hydrogenated polyisobutene, for example Synthetic esters and ethers, in particular of fatty acids, such as duck tail gland oil, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate, hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, heptanoic acid esters, caprylic acid esters and capric acid esters of fatty alcohols; polyol esters such as propylene glycol dicaprylate, neopentyl glycol diheptanoate, diethylene glycol diisononanoate, pentaerythritol esters, having 12 to 26 carbon atoms Fatty alcohols containing 2-undecyl alcohols, such as octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol, partially hydrocarbon-based and / or silicone-based fluoro oils, silicone oils, such as volatile or non-volatile linear or cyclic polydimethylsiloxanes (PDMS) such as cyclomethicone, dimethicone (optionally comprising phenyl groups) such as phenyl trimethicone, phenyltrimethylsiloxydiphenylsiloxane, diphenylmethyl-dimethyltrisiloxane, diphenyldimethicone, phenyldimethicone, polymethylphenylsiloxane; mixtures thereof. Details on suitable fatty substances are disclosed in WO 2012-038334.

[0274] preservative

[0275] Optionally, one or more preservatives may be included in the hair treatment formulation. Examples of such preservatives include one or more glycerol-containing compounds (e.g., glycerol or ethylhexylglycerol or phenoxyethanol), lactic acid, benzyl alcohol, EDTA, potassium sorbate and / or grape seed extract. In a preferred embodiment, the hair straightening formulation is free of parabens. Details on preservatives are disclosed in US 2009 / 0165812.

[0276] Skin protectant

[0277] Optionally, the hair treatment formulation includes one or more skin protectants. Skin protectants include one or more agents that prevent the undesired penetration of microorganisms or organic / inorganic chemicals. Details on skin protectants are disclosed in, for example, US 2009 / 0165812.

[0278] Conditioning Agents

[0279] Optionally, one or more conditioning agents may be included in the hair treatment formulation. In a preferred embodiment, silicone-based conditioning agents are introduced. Preferred materials are PDMS grades in the range of 10-1.000.000 mPa.s, silicones derivatized with C2-C18 alkyl groups, polydimethylsiloxanols, polyether-modified silicones, silicones containing amino groups or quaternary ammonium groups. They may also be chosen from polyorganosiloxanes having the functional group FA as defined above. These silicones may be introduced as pure materials, organic solutions, emulsions or microemulsions.

[0280] Preferred examples of conditioning agents containing quaternary ammonium groups (quaternary ammonium salts) are α,ω-quaternary ammonium group-terminated silicones (US4891166), quaternary ammonium group-terminated T-shaped silicones (US2008027202), α,ω-silicone block-terminated silicones (WO02 / 10256), and silicones containing quaternary ammonium groups arranged in a comb-like manner, optionally containing additional parts, i.e., polyether or aromatic structures (US2008213208, US5098979, US5153294, US5166297, US2006188456). Other preferred examples are copolymers based on quaternary ammonium groups / silicone blocks (EP282720, US6240929, US6730766, DE102004002208). In another preferred embodiment, copolymers based on quaternary ammonium groups / organic silicon blocks / hydrophilic blocks are used (WO 02 / 10257 and WO 02 / 10259, US7563856, US7563857, US20110039948, US2007106045, US2005255073, WO2004069137). Other preferred examples are copolymers based on quaternary ammonium groups / organic silicon blocks and copolymers based on quaternary ammonium groups / organic silicon blocks / hydrophilic blocks with terminal monofunctional silicone parts (WO2013148629, WO2013148635, WO2013148935). In another preferred embodiment of the present invention, silicones terminated with quaternary ammonium groups with pendant amino groups are used (DE10253152). Other preferred examples are silicone betaines (DE 10036522, DE 10036532). Commercially available examples of siloxanes comprising quaternary ammonium groups are Silsoft Silk and Silsoft Q (available from Momentive Performance Materials).

[0281] The above silicone-based conditioning agents impart a smooth and silky feel to the hair in particular.

[0282] Alternatively, hydrocarbon-based conditioning agents may be included. Details on these cationic materials comprising amino and / or quaternary ammonium groups are disclosed, for example, in US 2009 / 0000638 and WO 2012 / 027369.

[0283] Oxidants

[0284] Optionally, one or more oxidizing agents may be included in the hair treatment formulation. Preferred oxidizing agents include organic oxidizing agents, i.e. benzoquinone, other quinone derivatives, including hydroquinone and aminoquinone, and suitable organic peroxides. Details on organic oxidizing agents are disclosed in US 2012 / 0031420 and WO 2012 / 027369.

[0285] Hydrogen peroxide is the preferred inorganic oxidant. Persulfates (in the form of their sodium potassium and ammonium salts) may also be used, either alone or in combination with hydrogen peroxide just prior to use. Other possible oxidants include sodium percarbonate, sodium perborate, magnesium perborate, magnesium dioxide and barium dioxide. Details on these oxidants are disclosed in US 6544499.

[0286] reducing agent

[0287] Optionally, one or more reducing agents may be included in the hair treatment formulations, provided that no oxidizing agent and reducing agent are present simultaneously in the given formulation. Preferred reducing agents are thioglycolic acid and thiolactic acid and salts thereof, in particular the ammonium and ethanolamine salts. Other useful sulfur-containing compounds are, in particular, cysteine ​​or its hydrochloride, homocysteine, cysteamine, N-acetylcysteine, thioglycerol, ethylene glycol monothioglycolate, 1,2-propylene glycol monothioglycolate (see also WO 93 / 1791), 1-3-propylene glycol monothioglycolate or isomeric mixtures thereof, 1,3-butanediol and 1,4-butanediol monothioglycolate and isomeric mixtures thereof, polyethylene glycols such as diethylene glycol, triethylene glycol, and tetraethylene glycol monothioglycolate, glycerol monothiolactic acid and other thioacids and esters thereof, and mixtures thereof. Details on these organic reducing agents are disclosed in US 2009 / 0000638.

[0288] The use of inorganic reducing sulfur compounds is also possible in principle. Representative examples for use in the reducing composition include cosmetically acceptable salts (e.g., alkali metals (e.g., sodium and potassium) and ammonium salts), esters (e.g., lower alkyl), amines (e.g., triethanolamine (TEA), monoethanolamine (MEA) and aminomethylpropanol (AMP), sulfites, disulfites, bisulfites, metabisulfites, sulfoxylates, dithionites and pyrosulfites). Specific examples of suitable reducing agents therefore include sodium metabisulfite, potassium metabisulfite, sodium sulfite, potassium sulfite, sodium thiosulfate, potassium thiosulfate, ammonium bisulfite, ammonium sulfite, ammonium metabisulfite, MEA sulfite, MEA metabisulfite, potassium bisulfite, sodium bisulfite, ammonium bisulfite, sodium sulfite, sodium sulfite, sodium hyposulfite, potassium hyposulfite, ammonium hyposulfite, anhydrous sodium sulfite, diammonium sulfite, dipotassium disulfite, dipotassium pyrosulfite, AMP sulfite, AMP metabisulfite, TEA sulfite, TEA metabisulfite, sodium acid sulfite, sodium dithionite, sodium pyrosulfite, and sodium thiosulfate pentahydrate. Details about these inorganic reducing agents are disclosed in WO 2012 / 027369.

[0289] Alternatively, high temperature and alkali treated keratin (wherein the keratin is heated to about 100°C or higher), dithionites and certain hydrides may be used. Details on these reducing agents are disclosed in US Pat. No. 6,544,499.

[0290] K) Tannin

[0291] Optionally, one or more tannins may be used, in particular gallotannins, ellagitannins, complex tannins, condensed tannins, i.e. tannic acid and its other forms quercetin and gallotannic acid. Tannins represent a class of polyphenol derivatives and are known for their structural diversity. The classification is based on that given by K. Khanbabaee, T. van Ree, Nat. Prod. Rep., 2001, 18, 641-649 (which is hereby included as reference) and is used to define the term tannin in the context of the present invention. The most preferred tannin is gallotannic acid (= tannic acid). Preferred tannins include:

[0292]

[0293] Examples of gallotannins are

[0294]

[0295] Examples of ellagitannins are

[0296]

[0297] An example of a complex tannin is Acutissimin A

[0298]

[0299] Examples of condensed tannins are proanthocyanidin B2 (77), proanthocyanidin A1 (78), proanthocyanidin A2 (79) and proanthocyanidin C1 (80):

[0300]

[0301] The most preferred tannin is tannic acid:

[0302]

[0303] Metal Salts

[0304] These include, in particular, those of the following general formula:

[0305] Me x A y

[0306] Wherein Me in the formula is a metal cation and the number of cations Me is x and the number of anions A is y and the numbers x and y are such that the salt is neutral. In particular, x may be, for example, 1 or 2 and y may be, for example, 1-3. A is preferably of formula (i) - The anion of the oxidized carbohydrate of OC(O)-R, or an anion derived from an inorganic or organic acid. Me is preferably an iron or zinc cation.

[0307] Particularly preferred salts are Fe or Zn salts, which are preferably water soluble, such as Fe lactobionate 2+ , maltobionate Fe 2+ , Isomaltose Fe 2+ , Lactobionate Fe 3+ , maltobionate Fe 3+ , Isomaltose Fe 3+ , Fe gluconate 2+ , Fe gluconate 3+ Gluceptate Fe 2+ Gluceptate Fe 3+ , glycerophosphate Fe 2+ , glycerophosphate Fe 3+ , Lactobionic acid Zn 2+ , maltobionate Zn 2+ , Zn isomaltonic acid 2+ , Zn gluconate 2+ , and Zn glycerophosphate 2+ , Fe tartrate 2+ Glucarate Fe 2+ , Fe tartrate 3+ Glucarate Fe 3+ , Zn tartrate 2+ Glucaric acid Zn 2+ .

[0308] The weight ratio of the optional water-soluble Fe and / or Zn salt to the compound according to the invention is at least 0.01, preferably 0.01-3, more preferably 0.02-3, even more preferably 0.05-3, especially 0.1-3, even more especially 0.1-1. If the optional tannin is used, the weight ratio of the water-soluble Fe and / or Zn salt to the compound according to the invention plus tannin is at least 0.01, preferably 0.01-3, more preferably 0.02-3, even more preferably 0.05-3, especially 0.1-3, even more especially 0.1-1.

[0309] The specific amount of the water-soluble Fe or Zn salt depends on the molecular weight and structure of the water-soluble Fe or Zn salt and the molar ratio of the carboxyl groups in the compound of the present invention and the molar amount of the tannin used optionally. Typically, the higher the molecular weight of the water-soluble Fe or Zn salt and / or the higher the molar amount of the carboxyl groups in the organic compound of the present invention and the higher the molar amount of the optional tannin, the higher the specific amount of the water-soluble Fe or Zn salt used.

[0310] Other additives

[0311] The hair treatment formulations may also include one or more additional adjuvants, namely pH regulators such as acids, bases and buffers for adjusting the pH value, thickeners (e.g. polysaccharide thickeners, starches, modified starches, xanthan gum, exopolysaccharides, carrageenan, pullulan, cellulose, cellulose derivatives, polyacrylic acid, polyacrylate copolymers, polyacrylamide, pectin, clay, pyrogenic silica), lipids, amino acids, sugars, fragrances, sunscreens, vitamins, pearlescent agents, gelling agents, trace elements, sequestering agents, antioxidants, moisturizers, anti-hair loss agents, anti-dandruff agents, propellants, ceramides, polymers, in particular film-forming polymers; fillers, mother of pearl, colorants and in particular pigments and dyes, including hair coloring agents as described below, all kinds of biologically active phytochemicals, and mixtures thereof.

[0312] Hair dye

[0313] Hair coloring agents include commonly used oxidative or non-oxidative, temporary, semi-permanent, quasi-permanent and permanent hair dyes. Temporary non-oxidative dyes include, for example, acid yellow, acid orange 7, acid yellow 1, acid red 33, acid red 92, acid violet 43, acid blue 9, acid black 1, which are often used in mixtures. Semi-permanent non-oxidative hair coloring agents contain basic or cationic dyes with low molar mass, and in particular include HC Yellow No. 2, HC Red No. 3, 4-hydroxypropylamino-3-nitrophenol, N, N'-bis-(2-hydroxyethyl)-2-nitrophenylenediamine, HC Blue No. 2, Basic Red 51, Basic Red 76, Basic Brown 16, Basic Brown 17, Basic Blue 99, Basic Yellow 57. Other semi-permanent dyes include metal derivatives and plant derivatives (e.g. henna). The metal dyes are derived from silver salts, lead, and bismuth. Permanent oxidative hair colorants comprise the usual complex systems of precursors in the presence of an oxidizing agent.

[0314] Depending on the type of polymer structure and the intended application, a certain amount of acid, base and / or short-chain alcohol is required to obtain a clear formulation. Suitable acids include inorganic or organic acids, for example carboxylic acids such as acetic acid, hydrochloric acid, sulfuric acid, and phosphoric acid. Suitable bases include ammonia, alkaline hydroxides, alkaline carbonates, etc.

[0315] By adding, for example, such an acid or base, the aqueous composition may be adjusted to a suitable pH range of, for example, 9 or less, preferably 8.5 or less, preferably 7.5 or less, more preferably 7.0 or less.

[0316] A further preferred embodiment of the present invention relates to a cosmetic composition or personal care formulation comprising at least one polyorganosiloxane (A) and / or at least one compound (B) 1 according to the invention, or at least one aqueous composition (each as defined herein), for use in a color and style treatment of hair, preferably in a color treatment of hair.

[0317] Examples of personal care or cosmetic compositions in which the compounds of the present invention can be used include, but are not limited to, deodorants, antiperspirants, antiperspirant / deodorants (including sprays, sticks and roll-on products), shaving products, moisturizers, moisturizing creams, lotions, bath products, cleansing products, shampoos, conditioners, combination shampoo / conditioners, mousses, styling gels, hair sprays, hair dyes, hair color products, hair bleaches, perming products, hair straighteners, nail polish, nail polish removers, nail creams and lotions, cuticle softeners, sunscreens, insect repellents, anti-aging products, lip balms (lipsticks), foundations, face powders, eyeliners, eye shadows, rouge, colorants, Makeup, mascara, moisturizing preparations, foundation, preparations for the body and hands, skin care preparations (skin care preparations), preparations for the face and neck, tonics, compresses, hair combing aids, aerosol setting agents, perfume preparations, aftershaves, color cosmetic preparations, soft-focus applications, day and night skin care preparations, non-coloring hair preparations, tanning preparations, synthetic and non-synthetic soap bars, hand wash, nose strips, non-woven applications for personal care, baby lotion, baby shower gel and shampoo, baby conditioner, shaving preparations, cucumber slices, skin pads, makeup remover, cleansing products, cold creams, sunscreen products, mousse, injections, cream masks and muds, masks, colognes and toilet waters, hair cuticle packs shower gels, face and body washes, personal care rinse-off products, gels, foam baths, scrubbing cleansers, astringents, nail conditioners, eye shadow sticks, face or eye powders, lip balms, lip glosses, hair pump sprays and other non-aerosol sprays, hair frizz control gels, hair leave-in conditioners, hair oils, hair detangling products, hair styling products, hair bleaching products, moisturizers, shaving creams and electric shaving creams, anhydrous creams and lotions, oil / water, water / oil, multi- and coarse- and micro-emulsions, waterproof creams and lotions, anti-acne preparations, mouthwashes, massage oils, toothpastes, cleansing gels and cream sticks, ointment bases, topical wound healing products, aerosol talc, barrier Sprays, vitamin and anti-aging preparations, herbal extract preparations, bath salts, bath and body lotions, hair styling aids, hair-, eye-, nail- and skin-soft solid applications, controlled release personal care products, hair conditioning sprays, skin care moisturizing sprays, skin wipes, pore skin wipes, pore cleansers, acne reducers, skin exfoliants, skin desquamation enhancers, skin towelettes and cloths, depilatory preparations, personal care lubricants, nail coloring preparations, sunscreens, cosmetics, hair care products, skin care products, toothpastes, drug delivery systems for external application of medical compositions to be applied to the skin, combinations of two or more thereof, etc. Such cosmetic or personal care compositions of the present invention may include other ingredients and components as desired for the particular purpose or intended use.For example, the personal care composition may include ingredients selected from the group consisting of emollients, moisturizers, humectants, pigments, coated mica, colorants, fragrances, biocides, preservatives, antioxidants, antimicrobials, antifungals, antiperspirants, exfoliants, hormones, enzymes, medicinal compounds, vitamins, salts, electrolytes, alcohols, polyols, ultraviolet radiation absorbers, plant extracts, surfactants, silicone oils, organic oils, waxes, film formers, thickeners, particulate fillers, clays, surfactants, emulsifiers, solvents, emollients, moisturizers, humectants, pigments, colorants , fragrances, biocides, preservatives, chelating agents, antioxidants, antimicrobials, antifungals, antiperspirants, exfoliants, hormones, enzymes, medical compounds, vitamins, alpha-hydroxy acids, beta-hydroxy acids, retinol, niacinamide, skin lightening agents, salts, electrolytes, alcohols, polyols, ultraviolet radiation absorbers, plant extracts, organic oils, waxes, film formers, thickeners, particulate fillers, silicones, clays, plasticizers, humectants, occlusives, sensory enhancers, esters, resins, film formers, film-forming emulsifiers, high refractive index materials, combinations of two or more thereof, and the like.

[0318] Cosmetic products can be applied to the face, such as skin care creams (skin creams), lip balms (lipsticks), eye and face makeup, towelettes, and colored contact lenses. Cosmetic products can be applied to the body, such as deodorants, lotions, face powders, perfumes, baby products, bath oils, bubble baths, bath salts, and body butters; can be applied to the hands / nails: manicures and pedicures, and hand sanitizers; can be applied to the hair: permanent chemicals, hair colors, hair sprays, and gels; makeup compositions including color pigments, cosmetic products can be applied particularly to the face and eye area, such as primers, foundations or eye shadows, lip balms (lipsticks), lip glosses, lip liners, lip plumpers, lip balms, and lip balms. The present invention relates to lip balm, lip gloss, lip primer, lip gloss, and lip butter, which may contain sunscreen, concealer, face powder, mascara, eye shadow, eyeliner, eyebrow pencil, cream, wax, gel, and face powder (which is used to color, outline, and define eyebrows); lotion, cleansing formula; toner; mask; peel-off mask, sheet mask, exfoliating product, moisturizer such as cream or lotion, which may contain essential oils, herbal extracts, or other chemicals; night cream, day cream, sunscreen composition, nail polish, etc.

[0319] Personal care products that can include the compounds of the present invention include, for example, cosmetic and medical products, such as bar soaps, liquid soaps (e.g., hand soaps), hand sanitizers (including rinse-off and leave-on alcohol-based and water-based hand sanitizers), pre-surgical skin disinfectants, cleansing wipes, disinfecting wipes, body washes, acne treatment products, skin creams, shampoos, conditioners, cosmetics (including, but not limited to, liquid or powder foundations, liquid or solid eyeliners, mascara, cream eye shadows, tinted face powders, "decoction powders" for use dry or wet, "cake" type powder, etc.) deodorants, antimicrobial creams, body washes, hand creams, topical creams, aftershave lotions, toners, mouthwashes, toothpastes, sunscreens; and baby products, such as, but not limited to, cleansing wipes, baby shampoos, baby soaps, and diaper rash creams; wound care items, such as, but not limited to, wound healing ointments, creams, and lotions, wound covers, burn wound creams, bandages, adhesive tapes, and surgical steri-free tapes; and medical products such as medical gowns, caps, masks, and shoe covers, surgical drapes, etc. Additional products include, but are not limited to, oral products such as mouth rinses, toothpastes, and dental floss coatings. Veterinary and pet care products, antiseptic compositions, and surface disinfectants, including solutions, sprays or wipes, etc.

[0320] The aqueous or cosmetic composition according to the invention may be particularly (used in or) formulated in a form typical of hair treatment compositions. Preferred are external hair care or treatment compositions, such as hair tonics, conditioners (hair conditioners), hair care preparations, such as pre-treatment preparations, styling creams, styling gels, hair oils, shampoos, treatment packs, intensive hair treatments such as leave-in and rinse-off deep conditioners (hair conditioners), preparations for hair structuring, such as perming preparations for permanent waves (hot, warm, cold), preparations for hair straightening, liquid hair styling preparations, hair foams, hair serums, hair sprays, bleaching preparations, such as hydrogen peroxide solutions, lightening shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semi-permanent or permanent hair colorants, preparations containing self-oxidizing dyes, or natural hair colorants such as henna or chamomile. Depending on the application, the hair care preparations may in particular be in the form of (aerosol) sprays, (aerosol) foams, gels, gel sprays, creams, lotions, liquids, serums or waxes, mousses, shampoos, e.g. pearl shampoos, anti-frizz shampoos, etc. The aqueous compositions according to the invention can be used as leave-in or rinse-off hair treatment compositions.

[0321] A particularly preferred cosmetic composition according to the invention is for use in hair treatment, preferably in hair coloring treatment. The above aqueous cosmetic composition according to the invention may provide benefits in particular with regard to improved durability of artificial colors on the hair. Furthermore, the aqueous hair treatment formulation according to the invention provides hair strengthening and shaping effects as well as conditioning effects, in particular before, during and after hair coloring treatments, such as hair bleaching treatments. The hair treatment composition according to the invention may provide benefits with regard to hair strengthening, hair coloring, hair color retention, color deepening and shaping, i.e. curling and straightening of the hair.

[0322] Preferred cosmetic compositions for treating hair according to the invention are selected from hair shampoo compositions, hair care compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or color deepening or dyeing compositions, hair combing improving compositions, anti-frizz compositions, hair rinse and leave-in compositions.

[0323] In a further embodiment, the present invention relates to a method for treating hair comprising the steps of providing a cosmetic composition according to the present invention, and applying said cosmetic composition to said hair. Such a method for treating hair may further comprise the step of dyeing the hair.

[0324] A particularly preferred method for treating hair involves the following steps:

[0325] 1) contacting hair with the aqueous cosmetic composition of the present invention,

[0326] 2) optionally contacting the hair with an aqueous composition comprising a metal salt of Fe and / or Zn, including an aqueous phase, having a pH ranging from >2 to 10, and comprising a water-soluble Zn with a counterion preferably selected from the following 2 + , Fe 2+ and / or Fe 3+ Salt:

[0327] Chloride, sulfate, alkylsulfonate, arylsulfonate, alkylarylsulfonate, hydroxy-functional carboxylic acid, the hydroxy-functional carboxylic acid being in particular selected from

[0328] C2-C12, preferably C2-C9 saturated or unsaturated hydroxyalkyl carboxylic acids, i.e. glycolic acid, lactic acid, β-hydroxybutyric acid, γ-hydroxybutyric acid, 2-hydroxy-succinic acid, citric acid, mandelic acid,

[0329] C2-C12, preferably C2-C9, also preferably C7-C12, more preferably C7-C9 saturated or unsaturated polyhydroxyalkyl carboxylic acid, i.e. glyceric acid, 2,2-dihydroxymethylpropanecarboxylic acid, arabinonic acid, gluconic acid, glucuronic acid, glucoheptonic acid, glucopyranosylarabinonic acid, lactobionic acid, maltobionic acid, tartaric acid, glucaric acid,

[0330] C7-C12, preferably C7-C9 hydroxyaromatic carboxylic acids, i.e. 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2-hydroxycinnamic acid, 3-hydroxycinnamic acid, 4-hydroxycinnamic acid,

[0331] C7-C12, preferably C7-C9 polyhydroxyaromatic carboxylic acids, namely 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, dihydroxycinnamic acid or its partial esters, namely 3,4-dihydroxycinnamic acid, trihydroxybenzoic acid or its partial esters, namely 2,3,4-trihydroxybenzoic acid, 2,3,5-trihydroxybenzoic acid, 2,3,6-trihydroxybenzoic acid, 2,4,5-trihydroxybenzoic acid, 2,4,6-trihydroxybenzoic acid, 3,4,5-trihydroxybenzoic acid, trihydroxycinnamic acid or its partial esters, namely 3,4,5-dihydroxycinnamic acid, and mixtures thereof, and

[0332] 3) Drying the hair at a temperature preferably >150° C., for example during a hot ironing step, which essentially binds or incorporates the inventive hair treatment composition used in steps 1) and 2) or a portion of the hair treatment composition into the hair.

[0333] Another particularly preferred method for treating hair involves the following steps:

[0334] 1) contacting the hair with an aqueous cosmetic composition according to the invention, said composition comprising a compound according to the invention, optionally one or more surfactants as described above, and a metal salt of Fe and / or Zn, said metal salt being preferably a water-soluble Zn salt having a counterion preferably selected from the following: 2+ , Fe 2+ and / or Fe 3+ Salt:

[0335] Chloride, sulfate, alkyl sulfonate, aryl sulfonate, alkyl aryl sulfonate,

[0336] Hydroxy-functional carboxylic acids, in particular selected from

[0337] C2-C12, preferably C2-C9 saturated or unsaturated hydroxyalkyl carboxylic acids, i.e. glycolic acid, lactic acid, β-hydroxybutyric acid, γ-hydroxybutyric acid, 2-hydroxy-succinic acid, citric acid, mandelic acid,

[0338] C2-C12, preferably C2-C9, also preferably C7-C12, more preferably C7-C9 saturated or unsaturated polyhydroxyalkyl carboxylic acid, i.e. glyceric acid, 2,2-dihydroxymethylpropanecarboxylic acid, arabinonic acid, gluconic acid, glucuronic acid, glucoheptonic acid, pyranosyl arabinonic acid, lactobionic acid, maltobionic acid, tartaric acid, gum acid

[0339] C7-C12, preferably C7-C9 hydroxyaromatic carboxylic acids, i.e. 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2-hydroxycinnamic acid, 3-hydroxycinnamic acid, 4-hydroxycinnamic acid,

[0340] C7-C12, preferably C7-C9 polyhydroxyaromatic carboxylic acids, namely 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, dihydroxycinnamic acid or its partial esters, namely 3,4-dihydroxycinnamic acid, trihydroxybenzoic acid or its partial esters, namely 2,3,4-trihydroxybenzoic acid, 2,3,5-trihydroxybenzoic acid, 2,3,6-trihydroxybenzoic acid, 2,4,5-trihydroxybenzoic acid, 2,4,6-trihydroxybenzoic acid, 3,4,5-trihydroxybenzoic acid, trihydroxycinnamic acid or its partial esters, namely 3,4,5-dihydroxycinnamic acid, and mixtures thereof, and

[0341] 2) Drying the hair at >150° C., for example during hot ironing, which essentially binds the inventive hair treatment composition used in step 1) or a part of said hair treatment composition to the hair or incorporates it into the hair.

[0342] In the above method, the weight ratio of the optional water-soluble Fe and / or Zn salt to the compound according to the invention is at least 0.01, preferably 0.01-3, more preferably 0.02-3, even more preferably 0.05-3, especially 0.1-3, even more especially 0.1-1. If the optional tannin is used, the weight ratio of the water-soluble Fe and / or Zn salt to the compound according to the invention (polyorganosiloxane of formula (A) and / or compound of formula (B)) plus tannin is at least 0.01, preferably 0.01-3, more preferably 0.02-3, even more preferably 0.05-3, especially 0.1-3, even more especially 0.1-1. The specific amount of the water-soluble Fe and / or Zn salt depends on the molecular weight and structure of the water-soluble Fe or Zn salt and the molar ratio of carboxyl groups in the compound according to the invention and the molar amount of the optionally used tannin. Typically, the higher the molecular weight of the water-soluble Fe or Zn salt and / or the higher the molar amount of carboxyl groups in the organic compound of the invention and the higher the molar amount of optional tannin, the higher the specific amount of water-soluble Fe or Zn salt used.

[0343] Preferably, the method step 1) of contacting the hair with the aqueous cosmetic composition of the present invention to form treated hair is carried out at a temperature and for a time sufficient to penetrate the fibers. Typically, the method step 1) is carried out at 10-50° C., preferably 20-50° C., even more preferably at room temperature, for 5-120 min, preferably 5-60 min, even more preferably 10-40 min.

[0344] Preferably, the hair is treated with a water-soluble Zn-based 2+ , Fe 2+ and / or Fe 3+ Method step 2) of contacting the hair treatment composition of the invention with a salt to form further treated hair is carried out at a temperature and for a time sufficient to penetrate the fibers. Typically, method step 2) is carried out at 10-50° C., preferably 20-50° C. Even more preferably at room temperature for 5-20 min, preferably 5-60 min, even more preferably 10-40 min.

[0345] Preferably, method step 3) of drying the treated hair at a temperature of >150°C by applying heat is preferably a hot ironing step, which mainly binds or introduces the inventive hair treatment composition used in steps 1) and 2) or a part of said hair treatment composition to the hair. This elevated temperature may result in a chemical reaction of the components of the composition used in steps 1) and 2) with the reactive parts of the keratin fibres, or the formation of a complex of the components of the composition used in steps 1) and 2). The preferred temperature range is 150°C to about 235°C, more preferably 180°C to about 225°C, even more preferably 190°C to about 215°C. Typically, 2-10 cycles of hot ironing are applied while the hair is dry.

[0346] In the context of the present invention, the water-soluble Zn and / or Fe salt used in step 2) preferably has a water solubility of at least 0.5 g / l at 25°C.

[0347] In a preferred embodiment, the aqueous composition used according to the invention comprises at least one metal salt, for example a Zn and / or Fe salt, which is in particular as described above.

[0348] The above-described hair treatment method according to the present invention may provide benefits with respect to hair strengthening, hair shaping, i.e. curling and straightening of hair, hair coloring, hair bleaching, hair color maintenance, hair color deepening, hair conditioning.

[0349] The invention further relates to the use of an aqueous composition according to the invention for treating hair, in particular in the colour and shape treatment of hair, for example for strengthening hair, for colour maintenance of hair, for colour enhancement of hair, for colour deepening of hair, for colour protection of hair, for shaping hair, i.e. curling and straightening of hair, for conditioning hair, for smoothing or softening hair, for straightening hair, for improving the manageability of hair, in particular for improving the combability of hair.

[0350] The most preferred cosmetic compositions according to the invention are for use in hair treatment, preferably in hair coloring.

[0351] Most preferred cosmetic compositions according to the present invention are selected from hair shampoo compositions, hair care compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or dyeing compositions, hair combing improving compositions, anti-frizz compositions, hair rinse and leave-in compositions.

[0352] The invention further relates to the use of a polyorganosiloxane of formula (A) and / or a compound of formula (B) according to the invention or an aqueous composition according to the invention for treating hair, preferably for strengthening hair, for maintaining hair colour, for enhancing hair colour, for deepening hair colour, for protecting hair colour, for shaping hair, i.e. curling and straightening hair, for conditioning hair, for smoothing or softening hair, for straightening hair, for improving the manageability of hair, in particular for improving the combability of hair.

[0353] In a preferred embodiment, the aqueous composition according to the invention comprises at least one hair coloring agent. Preferably, the aqueous composition according to the invention is selected from hair shampoo compositions, hair care compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or dyeing compositions, hair color deepening compositions, hair combing improving compositions, anti-frizz compositions, hair rinses and leave-in compositions.

[0354] In a preferred embodiment, the aqueous composition according to the invention is used in a hair color treatment, such as in a hair color maintenance treatment, in a hair color enhancement treatment, in a hair color darkening treatment or in a hair color protection treatment.

[0355] In a preferred embodiment, the present invention relates to a method for color treatment of hair comprising the steps of providing an aqueous composition according to the present invention, and applying said aqueous composition to said hair.

[0356] A preferred embodiment of the present invention relates to a method for color treatment of hair, comprising the steps of providing an aqueous composition according to the present invention and applying said aqueous composition to said hair, and the step of coloring the hair.

[0357] A further preferred embodiment of the present invention relates to a compound (B) of the following formula, a salt thereof, and an aqueous composition thereof:

[0358] R 2 (–F) 2-18

[0359] in

[0360] R 2 is selected from optionally substituted divalent to octavalent hydrocarbon groups having up to 100 carbon atoms and which may optionally contain one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, a tertiary amino group and quaternary ammonium groups and

[0361] F is selected from:

[0362] –O–C(O)–R 3 –C(O)OH, and

[0363] –NR 1 –C(O)–R 3 –C(O)OH,

[0364] The group F is bonded to R 2 of carbon atoms,

[0365] in

[0366] R 1 is selected from hydrogen or an optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms, optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, a tertiary amino group and quaternary ammonium groups

[0367] R 3 is selected from a single bond or an optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms, optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, a tertiary amino group and quaternary ammonium groups

[0368] The condition is R 3 Not –CH=CH–.

[0369] A specific preferred compound (B) has the following formula:

[0370]

[0371] Where R 5 is selected from hydroxyl or F, wherein F is as defined above, provided that R 5 At least two of them are F.

[0372] A specific preferred compound (B) has the following formula:

[0373]

[0374] Where R 9 One of them is hydroxyl and R 9 One of the following groups

[0375]

[0376] and wherein F is as defined above, and the dashed line is a bond to the carbon atom.

[0377] A preferred compound (B) according to the present invention is a mixture of the following two isomers:

[0378]

[0379] wherein F is as defined above.

[0380] A preferred compound (B) according to the present invention has the following formula:

[0381]

[0382] wherein x is 1-10, preferably 1-5, and F is as defined above.

[0383] In preferred compounds (B) according to the present invention, R 3 is selected from a single bond and a linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 18, preferably up to 12, more preferably up to 10 carbon atoms and optionally comprising one or more radicals selected from —O—, —NH—, —C(O)—, and wherein R 3 Optionally substituted by one or more groups selected from hydroxyl groups, amino groups, and carboxyl groups. More preferably, in compound (B), R 3 Derived from a dicarboxylic acid of the formula:

[0384]

[0385] Where R 3As defined above, the dicarboxylic acid is, for example, an optionally substituted saturated or unsaturated aliphatic dicarboxylic acid or an aromatic dicarboxylic acid, such as oxalic acid (oxalic acid), malic acid (malonic acid), succinic acid (succinic acid), gum acid (glutaric acid), adipic acid (adipic acid), syrup acid (pimelic acid), suberic acid (suberic acid), azelaic acid (zelaic acid), sebacic acid (decanedioic acid), undecanedioic acid, dodecanedioic acid, brassic acid (tridecanedioic acid), hexadecanedioic acid, glutaconic acid (pent-2-enedioic acid), citraconic acid ((2Z)-2-methylbut-2-enedioic acid), mesaconic acid ((2E)-2-methyl-2-butenedioic acid), itaconic acid (2-methylenesuccinic acid), tartrate (2-hydroxymalonic acid), mesooxalic acid (oxomalic acid), malic acid (hydroxysuccinic acid), tartaric acid (2,3-dihydroxybutanediol acid), oxaloacetic acid (oxobutanedioic acid), aspartic acid (2-aminobutanedioic acid), α-hydroxyglucoamic acid (2-hydroxyglutaric acid), arabinonic acid (2,3,4-trihydroxyglutaric acid), acetone dicarboxylic acid (3-oxoglutaric acid), α-ketoglucoamic acid (2-oxoglutaric acid), glutamic acid (2-aminoglutaric acid), diaminosyrup ((2R,6S)-2,6-diaminopimelic acid), saccharic acid ((2S,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid), phthalic acid (benzene-1,2-dicarboxylic acid), isophthalic acid (benzene-1,3-dicarboxylic acid), terephthalic acid ((benzene-1,3-dicarboxylic acid)), biphenylcarboxylic acid (2-(2-carboxyphenyl)benzoic acid), 2,6-naphthalene dicarboxylic acid, norbornene dicarboxylic acid, norbornane dicarboxylic acid; and trimellitic acid; or R 3 Derived from aliphatic or aromatic tricarboxylic acids, wherein R 3 Substituted with a carboxyl group (COOH), for example citric acid (2-hydroxypropane-1,2,3-tricarboxylic acid), isocitric acid (1-hydroxypropane-1,2,3-tricarboxylic acid), aconitic acid ((cis or trans-prop-1-ene-1,2,3-tricarboxylic acid), propane-1,2,3-tricarboxylic acid, trimesic acid (benzene-1,3,5-tricarboxylic acid), carboxylic anhydrides such as maleic anhydride and succinic anhydride with amino acids and amino acid derivatives, such as β-alanine and asparagine, i.e. N-acetylaspartic acid, N-maleyl-β-alanine ((E)-4-(2-carboxyethylamino)-4-oxo-but-2-enoic acid), N-maleyl-asparagine (4-amino-2-[[(E)-4-hydroxy-4-oxo-but-2-enoyl]amino]-4-oxo-butyric acid).

[0386] In preferred compounds (B) according to the present invention, F is selected from the following formulae:

[0387]

[0388]

[0389]

[0390] wherein the dotted line in the above formula represents a bond to the oxygen atom, and wherein at least two groups F are present.

[0391] In a further preferred embodiment of the present invention, it relates to polyorganosiloxanes (A), and aqueous compositions thereof, wherein the polyorganosiloxanes (A) have an average number of 2 to 1000 siloxy units selected from siloxy groups having the following formula:

[0392]

[0393] in

[0394] R is selected from R 1 and R F ,in

[0395] R 1 are selected from organic groups bonded to the silicon atom via a carbon atom, and the two groups R 1 Can form a bridging group between two silicon atoms,

[0396] R F Select from different R 1 and is bonded to the silicon atom via a carbon atom, and R F Contains at least one functional group F selected from the following:

[0397] –O–C(O)–R 3 –C(O)OH, and

[0398] –NR 4 –C(O)–R 3 –C(O)OH, and

[0399] wherein the group F is bonded to a carbon atom, wherein

[0400] R 3 is selected from a single bond or an optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms, optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, a tertiary amino group and quaternary ammonium groups

[0401] The condition is R 3 is not –CH=CH– or –CH2–CH2–, and

[0402] R 4is selected from hydrogen or an optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms, optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, a tertiary amino group and quaternary ammonium groups Among them, preferred substituent groups have the same meanings as described above.

[0403] Aspects of the present invention may be further understood with reference to the following non-limiting examples. Example

[0404] (Percentages refer to weight % unless otherwise stated).

[0405] Example 1

[0406] Succinate derivatives based on glycerol diglycidyl ether

[0407] In a 250 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 23.1 g (195.8 mmol) of succinic acid, 122 g of dipropylene glycol and 0.8 g of triethylamine were mixed and heated to 90° C. 20 g (195.8 mmol epoxy groups) of glycerol diglycidyl ether was added. The mixture was kept at 90°C for 12 hours. Afterwards, the transparent light yellow mixture was cooled to room temperature and 1 The conversion of epoxy groups was determined by H NMR spectroscopy. The conversion of epoxy groups was 100%.

[0408] A product consisting essentially of the following isomers was obtained

[0409]

[0410] Example 2

[0411] Glycerol diglycidyl ether with three succinate functions

[0412] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 10 g (97.9 mmol epoxy groups) of glycerol diglycidyl ether, 11.56 g succinic acid (97.9 mmol), 61.7 g methoxypropyl acetate and 0.53 g trimethylamine were mixed and heated to 90° C. for 15 hours. As the esterification reaction proceeded, the mixture became turbid. 1 The conversion of epoxy groups determined by H NMR spectroscopy was 100%.

[0413] 4.9 g (48.9 mmol) of succinic anhydride was added and the reaction was continued at 90°C for 6 hours. During the second esterification reaction, the mixture became transparent (slightly brown). 1 The conversion of the anhydride groups determined by H NMR spectroscopy was 100%.

[0414] 61.7 g 1,3-butanediol were added. Methoxypropyl acetate was removed under reduced pressure at 75° C. / 3 mm Hg.

[0415] A slightly brownish, transparent liquid was obtained.

[0416] A product consisting essentially of the following isomers was obtained:

[0417]

[0418] Where R1 is –OH and –OC(O)CH2CH2COOH in a ratio of 2:1.

[0419] Example 3

[0420] Fatty acid ester derivatives based on glycerol diglycidyl ether

[0421] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 10 g (97.9 mmol epoxy groups) of glycerol diglycidyl ether, 14.31 g adipic acid (97.9 mmol), 56.71 g 1,3-butanediol and 0.48 g trimethylamine were mixed and heated to 90° C. for 9.5 hours. 1 The conversion of epoxy groups determined by H NMR spectroscopy was 99.5%. A colorless transparent liquid was obtained.

[0422] A product consisting essentially of the following isomers was obtained:

[0423]

[0424]

[0425] Example 4

[0426] Glycerol diglycidyl ether having two succinate functions and two fatty ester functions

[0427] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 14.31 g of adipic acid (97.9 mmol), 56.71 g of methoxypropyl acetate and 0.51 g of trimethylamine were mixed and heated to 70° C. 10 g (97.9 mmol of epoxy groups) of glycerol diglycidyl ether were added over 15 minutes. The initially turbid mixture became clear. Afterwards, the temperature was raised to 90° C. and maintained for 11 hours.

[0428] If through 1 The conversion of the epoxy groups determined by H NMR spectroscopy was 99%.

[0429] 9.79 g (97.9 mmol) of succinic anhydride was added and the reaction was continued at 90°C for 6.5 hours. 1 The conversion of the anhydride groups determined by H NMR spectroscopy was 98%.On cooling to room temperature, the target product precipitated from the solution.

[0430] 79.6 g of 1,3-butanediol were added. Methoxypropyl acetate was removed under reduced pressure at 75° C. / 3 mm Hg.

[0431] A slightly yellowish transparent liquid was obtained.

[0432] A product consisting essentially of the following isomers was obtained:

[0433]

[0434]

[0435] Where R1 is –OH and –OC(O)CH2CH2COOH in a ratio of 1:2.

[0436] Example 5

[0437] Itaconate derivatives based on triglycerol

[0438] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 60 g of methoxypropyl acetate, 10 g (41.6 mmol) of triglycerol were added.

[0439]

[0440] Mix with 0.29 g of triethylamine and heat to 70° C. 9.33 g (83.2 mmol) of itaconic anhydride are added dropwise over 15 minutes. The mixture is heated to 90° C. for 18 hours. The initially yellow dispersion becomes slightly reddish during the course of the reaction. 1The conversion of the anhydride was determined by H NMR spectroscopy. The conversion of the anhydride was 100%. Subsequently, 60 g of 1,3-butanediol were added and methoxypropyl acetate was removed at 70° C. / 20 mbar over a period of 2 hours. A pale yellow, transparent solution was obtained.

[0441] A product consisting essentially of the following structure was obtained:

[0442]

[0443] The two Rs are:

[0444]

[0445] (The dashed line is the bond to the oxygen atom)

[0446] And three are hydrogen.

[0447] Example 6

[0448] Itaconate derivatives based on glycerol diglycidyl ether

[0449] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 10.76 g (82.7 mmol) of itaconic acid, 60 g of 1,3-butanediol and 0.29 g of triethylamine were mixed and heated to 80° C. 8.45 g (82.7 mmol of epoxy groups) of glycerol diglycidyl ether were added dropwise over 20 minutes. The temperature was raised to 86° C. It was further raised to 90° C. and maintained there for 14 hours. Afterwards, the transparent colorless mixture was cooled to room temperature and stirred by 1 The conversion of epoxy groups was determined by H NMR spectroscopy. The conversion of epoxy groups was 100%.

[0450] A product consisting essentially of the following isomers was obtained:

[0451]

[0452]

[0453] Where R1 is

[0454]

[0455] (The dashed line is the bond to the oxygen atom).

[0456] Application Testing

[0457] Test Method

[0458] The test method for evaluating color retention is described in detail in US 2011 / 0219552 A1. The method determines the change in hair color before and after washing by ΔE. The color change is measured by measuring the CIE L*, a* and b* values ​​(or CIELAB color space) on a HunterLab colorimeter.

[0459] The meaning of L*, a*, b* is detailed in "Practical Modern Hair Science" Trefor Evans and R. Randall Wichett, Alluredbooks, Carol Stream, Illinois, 2012. The L* value measures lightness from L*=0 (black) to L*=100 (white). Color is measured by a* from negative values ​​(green) to positive values ​​(red) and b* from negative values ​​(blue) to positive values ​​(yellow). For example, mid-flax has L*, a*, b* values ​​of L*=49, a*=12, b*=26 and mid-auburn has L*, a*, b* values ​​of L*=26, a*=13, b*=12.

[0460] ΔE was calculated using the following equation to evaluate the color change before and after washing.

[0461]

[0462] in and CIE L*, a*, b* color parameters (CIELAB color space) measured before and after washing, respectively.

[0463] Larger ΔE values ​​reflect greater color change, thus smaller ΔEs are desirable as they indicate less color loss after washing.

[0464] Similarly, color enhancement was calculated using the following equation to assess the increase in initial color depth with treatment.

[0465]

[0466] in and CIE L*, a*, b* color parameters measured before washing with and without treatment, respectively. Here, a larger ΔE is desired as it means a larger initial color enhancement.

[0467] Example 7

[0468] Example 7.1 Application to Color Enhancement and Color Maintenance of Single Bleached European Hair The following treatment solution was prepared:

[0469] TS1 solution (polyglycerol succinate from Example 1) approximately 50 ml is composed of 3 g of polyglycerol succinate from Example 1, 7 g of dipropylene glycol (ie, a solution of 10 g of polyglycerol succinate obtained in Example 1 in dipropylene glycol), and 40 g of water.

[0470] The hair dye was a commercial hair dye Garnier Nutrisse Ultra Color R3, Light Intense Auburn from L'Oreal.

[0471] Pretreatment of hair with the aqueous solution according to the invention before dyeing

[0472] A 4 g single bleached European hair tress (Kerling International Haarfarbrik GMBH) was immersed in 50 g TS1 solution for 30 minutes. The hair was then dried overnight at room temperature. The hair tress was then washed 3 times through 10 wt% SLES (sodium lauryl ether sulfate). The hair was dried and then dyed with Garnier R3 dye according to the standard dyeing procedure of Garnier R3 for 30 minutes.

[0473] The control tress is a tress treated with 50 ml of water. And it is then washed with 10% by weight SLES and dyed with Garnier R3 dye, identical to the tress treated with the cross-linking technique. The initial color is measured.

[0474] After-treatment of hair with the aqueous solution according to the invention after dyeing

[0475] A 4 g tress of single bleached European hair (Kerling International Haarfarbrik GMBH) was dyed with Garnier R3 dye according to the standard dyeing procedure of Garnier R3 for 30 minutes. The hair was then dried through a bonnet. The initial color was measured. The dried hair was immersed in 50 g of TS1 solution for 30 minutes. The hair was then dried overnight at room temperature. The hair tress was then washed 3 times through 10 wt% SLES (sodium lauryl ether sulfate). The hair was then dried.

[0476] The control tress was a tress dyed with Garnier R3 treated with 50 ml of water. The hair was then washed with 10% by weight SLES and dried, identical to the tresses treated with the cross-linking technique.

[0477] Washing program

[0478] 4 g of hair tresses were placed in a 250 ml conical bottle with 200 ml of 2.5% SLES solution. The bottle was shaken in a ShelLab shaking water bath at 120 rpm at 42°C for 5 minutes. (5 minutes wash equals 10 hand washes). After 5 minutes, the hair was dried and the hair color was measured.

[0479] Pretreatment Benefits

[0480] Color enhancement ΔE due to pretreatment

[0481]

[0482] The hair treated by the technique according to the invention before dyeing showed a color enhancement effect with a darker initial color compared to the control.

[0483] Color retention benefits due to pre-treatment

[0484] Color loss ΔE Control 12.50 TS1 (polyglycerol succinate from Example 1) 7.20

[0485] The technology according to the invention (TS1 solution (polyglycerol succinate from Example 1)) shows a color retention effect with a lower color loss ΔE compared to the control.

[0486] Post-processing benefits

[0487] The original color depth was maintained with almost no change in L* by post-treatment with the polyglycerol succinate from Example 1.

[0488]

[0489] Color retention benefits due to post-processing

[0490] Color loss ΔE Control 17.91 TS1 (polyglycerol succinate from Example 1) 5.28

[0491] Shows color retention with lower color loss ΔE compared to the control.

[0492] Post-treatment according to the technology of the invention (TS1 solution (polyglycerol succinate from Example 1)) reduces the color loss ΔE by more than 12 units.

[0493] Example 7.2 Post-bleaching treatment

[0494] 4 grams of undamaged dark brown hair tresses were obtained from Hair International Importers. Commercial bleaching lightening powder (9 grams) and commercial 40 volume developer (11 grams) were mixed together. The bleaching composition was applied to the original dark brown hair tresses, diffused and left on the hair tresses for 50 minutes. After rinsing the dye from the tresses with tap water, the tresses were washed and rinsed with a 10 wt% sodium polyethylene glycol monododecyl ether sulfate (2EO) solution. The dried hair was immersed in 50 g of TS1 solution for 30 minutes. The hair was then dried overnight at room temperature. The hair tresses were then washed 3 times through 10 wt% SLES (sodium lauryl ether sulfate). The hair was then dried.

[0495] This treatment is intended to strengthen hair after bleaching.

[0496] Example 7.3: White Rinse Conditioner Formulation

[0497]

[0498]

[0499] 1. Part A. Mix lactic acid and water and heat to 80°C.

[0500] 2. Add Part B to Part A and stir the mixture at 80°C for 1-3 hours to provide a homogenous formulation.

[0501] 3. Add part C to the mixture of A and B and stir at 80°C for 0.5-1 hour until part C is completely dissolved and a homogeneous mixture is obtained.

[0502] 4. Remove from heat while continuing to stir until reaching room temperature.

[0503] 5. Add part D to the mixture consisting of A+B+C and continue stirring until a homogeneous mixture is achieved.

[0504] Example 7.4. Pearlescent Shampoo Formula

[0505]

[0506] Part A: The components of Part A were mixed with an overhead mechanical stirrer at 600 rpm for 10 minutes.

[0507] Part B: 1 g of ethylene glycol distearate and 10 g of water were mixed with a magnetic stirrer at 200 rpm for 15 minutes.

[0508] Part C: 1 g of cocamide monoethanolamide and 10 g of water were mixed with a magnetic stirrer at 200 rpm for 15 minutes.

[0509] Add the components of Part D to Part A and stir with an overhead mechanical stirrer at 600 rpm for 10 minutes. Obtain mixture A+D.

[0510] Add part B to mixture A+D and stir with a mechanical stirrer at 600 rpm for 10 minutes. Obtain mixture A+D+B.

[0511] Add part C to mixture A+D+B and stir with a mechanical stirrer at 600 rpm for 10 minutes. Obtain mixture A+D+B+C.

[0512] Add part E to mixture A+D+B+C and stir with a mechanical stirrer at 600 rpm for 15 minutes. Obtain mixture A+D+B+C+E.

[0513] Finally part F was added to the mixture A+D+B+C+E and the mixture was stirred with a mechanical stirrer at 600 rpm for 15 minutes.

[0514] Example 7.5: Pearlescent Shampoo Non-Sulfate Version

[0515]

[0516] Part A: The components of Part A were mixed with an overhead mechanical stirrer at 600 rpm for 10 minutes.

[0517] Part B: 1.5 g of cocamide monoethanolamide was mixed with 10 g of water (45° C.) using a magnetic stirrer at 200 rpm for 30 minutes.

[0518] Part C: 1.5 g of hydroxypropylmethylcellulose powder was slowly added to 10 g of water (45° C.) and stirred with a magnetic stirrer at 200 rpm for 30 minutes.

[0519] Part D: 1.5 g of ethylene glycol distearate powder was slowly added to 10 g of water (45° C.) and stirred with a magnetic stirrer at 200 rpm for 30 minutes.

[0520] Part B was slowly added to part A over 5 minutes with mechanical stirring at 600 rpm. A mixture A+B was obtained.

[0521] Add part C slowly to part A+B over 5 minutes with mechanical stirring at 600 rpm. Obtain mixture A+B+C.

[0522] Add part D slowly to part A+B+C over 5 minutes with mechanical stirring at 600 rpm. Obtain mixture A+B+C+D.

[0523] Add part E to parts A+B+C+D over 5 minutes with mechanical stirring at 600 rpm. Obtain mixture A+B+C+D+E.

[0524] Part F was added to mixture A+B+C+D+E and mechanically stirred at 600 rpm for 15 minutes.

[0525] Finally, part G was added and the mixture was stirred at 600 rpm for 30 minutes.

[0526] Example 7.6: Anti-Frizz Shampoo

[0527]

[0528] Part A: The components of Part A were mixed using a magnetic stirrer at 200 rpm for 15 minutes.

[0529] Part B: The components of Part B were mixed using a magnetic stirrer at 200 rpm for 15 minutes.

[0530] Part B was added to Part A and the mixture was stirred with an overhead mechanical stirrer at 500 rpm for 15 minutes.

[0531] The components of Part C were added to Mixture A+B and stirred with an overhead mechanical stirrer at 500 rpm for 1 hour.

[0532] The components of Part D were mixed with a magnetic stirrer at 200 rpm for 15 minutes and then added to the mixture A+B+C.

[0533] Finally, the whole mixture A+B+C+D was mixed with a mechanical stirrer at 500 rpm for 30 minutes.

[0534] Example 7.7: Water-based spray formulation

[0535] 1.5 wt.% polyglycerol succinate from Example 1

[0536] 3.5 wt% dipropylene glycol,

[0537] 1.25 wt% SLES,

[0538] 0.09 wt % NaOH (added as a 10 wt % active NaOH solution in water at pH 8)

[0539] Add water to 100% by weight

[0540] Example 7.8: Isopropyl alcohol (IPA) based spray formulation

[0541] 1.5 wt.% polyglycerol succinate from Example 1

[0542] 3.5 wt% dipropylene glycol

[0543] Replenish to 100% IPA

[0544] Example 8: Processing of gel and cream formulations

[0545] Example 8.1:

[0546]

[0547]

[0548] Example 8.2:

[0549] Element weight% Phospholipids (and) soybean oil 2 Propylene glycol 3 Polyglycerol succinate from Example 1 10 Sodium Acrylates Copolymer and Lecithin 1.7 Stearic acid 0.5 Behenyl alcohol 0.5 Isononyl Isononanoate 2 Glycerin and spruce extract and alcohol 1 Phenoxyethanol 0.5 Butylene glycol dicaprylate / dicaprate 2 water Supplement to 100

[0550] Example 9

[0551] Tartaric acid ester derivatives based on glycerol diglycidyl ether

[0552] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 15 g (146.9 mmol epoxy groups) of glycerol diglycidyl ether, 22.05 g (146.9 mmol) of tartaric acid, 0.56 g of trimethylamine and 86.45 g of dipropylene glycol were mixed and heated to 90° C. for 12 hours. Afterwards, the mixture was cooled to room temperature and stirred by 1 The conversion of epoxy groups was determined by H NMR spectroscopy. The conversion of epoxy groups was 100%.

[0553] A colorless product consisting essentially of the following isomers was obtained:

[0554]

[0555]

[0556] in

[0557] R1 is –OC(O)CH(OH)CH(OH)C(O)OH.

[0558] Example 10

[0559] N-Acetyl Aspartate Derivatives Based on Glycerol Diglycidyl Ether

[0560] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 5 g (48.9 mmol epoxy groups) of glycerol diglycidyl ether, 8.58 g (48.9 mmol) of N-acetylaspartic acid:

[0561] 0.2 g of trimethylamine and 54.3 g of 1,3-butanediol were mixed and heated to 90° C. for 10 hours. Afterwards, the mixture was cooled to room temperature and 1 The conversion of epoxy groups was determined by H NMR spectroscopy. The conversion of epoxy groups was 100%.

[0562] A slightly yellowish product consisting essentially of the following isomers was obtained:

[0563]

[0564]

[0565] in

[0566] R1 is –OC(O)CH2CH(R*)C(O)OH or –OC(O)CH(R*)CH2C(O)OH, wherein

[0567] R*=-NH(CO)CH3.

[0568] Embodiment 11

[0569] N-Maleyl-β-alanine ((E)-4-(2-carboxyethylamino)-4-oxo-but-2-enoic acid)

[0570] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 17.8 g (200 mmol) of β-alanine was dissolved in 40 g of DI water at room temperature. 19.6 g (200 mmol) of maleic anhydride was added. The temperature was raised from 22°C to 36°C in 20 minutes. The mixture became a turbid white dispersion. The temperature was adjusted to 22°C for 3 hours. Afterwards, the precipitate was filtered, washed 10 times with 20 ml of DI water, and washed 3 times with 20 ml of cyclohexane. Finally, the volatiles were removed at 40°C / 20 mm Hg. By 1 H NMR spectroscopy confirmed the structure of the material.

[0571] 22 g of a white powder consisting essentially of the following structure were obtained.

[0572] N-Maleyl-β-alanine ((E)-4-(2-carboxyethylamino)-4-oxo-but-2-enoic acid):

[0573]

[0574] Example 12

[0575] N-Maleyl β-Alanine Derivatives Based on Glycerol Diglycidyl Ether

[0576] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 10 g (53.4 mmol) of N-maleyl β-alanine according to Example 11, 60 g of 1,3-butanediol and 0.23 g of trimethylamine were mixed at room temperature and heated to 70° C. 5.45 g (53.4 mmol of epoxy groups) of glycerol diglycidyl ether were added. The mixture was heated to 90° C. for 12 hours. During the heating process the mixture became transparent. Afterwards, the mixture was cooled to room temperature and heated by 1 The conversion rate of epoxy groups was determined by HNMR spectroscopy. The conversion rate of epoxy groups was 100%.

[0577] A reddish product consisting essentially of the following isomers was obtained:

[0578]

[0579] in

[0580] R1 is -OC(O)CH=CHC(O)NHCH2CH2C(O)OH or -OC(O)CH2CH2NHC(O)CH=CHC(O)OH.

[0581] Embodiment 13

[0582] N-Maleyl-asparagine (4-amino-2-[[(E)-4-hydroxy-4-oxo-but-2-enoyl]amino]-4-oxo-butyric acid)

[0583] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 26.42 g (200 mmol) of asparagine was dispersed in 46 g of DI water at room temperature. 19.6 g (200 mmol) of maleic anhydride was added. The mixture formed a white dispersion, which was stirred at 23°C for 5 hours. Afterwards, the mixture was heated to 50°C for 5.5 hours. It formed a clear solution. The volatiles were removed at 45°C / 20 mmHg. The sticky residue was washed twice with 2-propanol and the volatile components were removed at 45°C / 20 mmHg. By 1 H NMR spectroscopy confirmed the structure of the material.

[0584] A colorless, candy-like material consisting essentially of the following structure was obtained:

[0585]

[0586] Embodiment 14

[0587] N-Maleyl Asparagine Derivatives Based on Glycerol Diglycidyl Ether

[0588] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 12.29 g (53.4 mmol) of N-maleyl asparagine according to Example 13, 60 g of 1,3-butanediol and 0.27 g of trimethylamine were mixed at room temperature and heated to 70° C. 5.45 g (53.4 mmol of epoxy groups) of glycerol diglycidyl ether were added. The mixture was heated to 90° C. for 12 hours. A white dispersion was formed during the heating process. Afterwards, the mixture was cooled to room temperature and stirred by 1 The conversion of epoxy groups was determined by H NMR spectroscopy. The conversion of epoxy groups was >99%.

[0589] A white dispersion consisting essentially of the following isomers was obtained:

[0590]

[0591] in

[0592] R1 is -OC(O)CH=CHC(O)NHCH(CH2C(O)NH2)C(O)OH or -OC(O)CH(CH2C(O)NH2)NHC(O)CH=CHC(O)OH.

[0593] The material is instantly soluble in DI water.

[0594] Application Examples

[0595] Embodiment 15

[0596] Application for color enhancement and color maintenance of single-bleached European hair

[0597] Prepare the following treatment solutions:

[0598] TS2 solution (Glycerol diglycidyl ether-based tartaric acid ester derivative from Example 9) About 50 ml is composed of: 3 g of glycerol diglycidyl ether-based tartaric acid ester from Example 9, 7 g of 1,3-butanediol (i.e., 10 g of a solution of glycerol diglycidyl ether-based tartaric acid ester obtained in Example 9 in 1,3-butanediol), and 40 g of water.

[0599] TS3 solution (N-acetyl aspartic acid ester derivative based on glycerol diglycidyl ether from Example 10) Approximately 50 ml is composed of: 3 g of N-acetyl aspartic acid ester based on glycerol diglycidyl ether from Example 10, 12 g of 1,3-butanediol (i.e., 15 g of a solution of tartaric acid ester based on glycerol diglycidyl ether obtained in Example 10 in 1,3-butanediol), and 35 g of water.

[0600] TS4 solution (Glycerol diglycidyl ether-based N-maleoyl β-alanine derivative from Example 12) Approximately 50 ml is composed of: 3 g of the glycerol diglycidyl ether-based N-maleoyl β-alanine derivative from Example 12, 12 g of 1,3-butanediol (i.e., 15 g of a solution of the glycerol diglycidyl ether-based N-maleoyl β-alanine derivative obtained in Example 12 in 1,3-butanediol), and 35 g of water.

[0601] The hair dye was a commercial hair dye Garnier Nutrisse Ultra Color R3, Light Intense Auburn from L'Oreal.

[0602] After the dyeing step, post-treatment with an aqueous solution according to the invention

[0603] A 4 g tress of single bleached European hair (Kerling International Haarfarbrik GmbH) was dyed with Garnier R3 dye according to the standard dyeing procedure of Garnier R3 for 30 minutes. The hair was then dried through a bonnet. The initial color was measured. The dried hair was immersed in 50 g of TS2 solution or TS3 solution or TS4 solution for 30 minutes. The hair was then dried overnight at room temperature. The hair tress was then washed 3 times through 10 wt% SLES (sodium lauryl ether sulfate). The hair was then dried.

[0604] The control tress was a tress dyed with Garnier R3 treated with 50 ml of water. The hair was then washed with 10% by weight SLES and dried, identical to the tresses treated with the cross-linking technique.

[0605] Washing program

[0606] 4 g of hair tresses were placed in a 250 ml conical bottle with 200 ml of 2.5% SLES solution. The bottle was shaken in a ShelLab shaking water bath at 120 rpm at 42°C for 5 minutes, (5 minutes wash equals 10 hand washes). After 5 minutes, the hair was dried and the hair color was measured.

[0607] Post-processing benefits

[0608] Color enhancement (darkening) caused by TS2 post-processing

[0609]

[0610] TS2 significantly darkens the hair tone in post-processing solutions.

[0611] The TS3 and TS4 treatments did not darken the tone.

[0612]

[0613] Color retention benefits due to post-processing

[0614]

[0615] The above table on post-treatment results shows that TS2, TS3 and TS4 provide significant and visible color loss benefits relative to the control. TS3 and TS4 provide about 10 color loss ΔE improvement relative to the control, while TS2 provides about 7.5 color loss ΔE improvement.

[0616] Example 16

[0617] Silicone-based tartaric acid ester derivatives (terminal)

[0618] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 15 g (39.7 mmol epoxy groups) of an organosilicon diepoxide of the following structure was added.

[0619]

[0620] 5.96 g (39.7 mmol) of tartaric acid, 0.31 g of trimethylamine and 48.9 g of 1,3-butanediol were mixed at room temperature under N2. The mixture was heated to 90°C for 11 hours. Afterwards, the mixture was cooled to room temperature and 1 The conversion of epoxy groups was determined by H NMR spectroscopy. The conversion of epoxy groups was 99%.

[0621] A colorless product consisting essentially of the following structure is obtained:

[0622]

[0623] in

[0624] x = 5.3, and

[0625] R is –OC(O)CH(OH)CH(OH)C(O)OH.

[0626] Embodiment 17

[0627] Silicone-based N-acetyl aspartate derivatives

[0628] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 10 g (26.5 mmol epoxy groups) of an organosilicon diepoxide of the following structure was added.

[0629]

[0630] 4.64 g (26.5 mmol) of N-acetylaspartic acid, 0.22 g of trimethylamine and 58.6 g of 1,3-butanediol were mixed at room temperature under N2. The mixture was heated to 90°C for 10 hours. Afterwards, the mixture was cooled to room temperature and 1 The conversion of epoxy groups was determined by H NMR spectroscopy. The conversion of epoxy groups was 100%.

[0631] A brownish product was obtained which consisted essentially of the following structure:

[0632]

[0633] in

[0634] x = 5.3, and

[0635] R is –OC(O)CH2CH(R*)C(O)OH or –OC(O)CH(R*)CH2C(O)OH, where

[0636] R*=-NH(CO)CH3.

[0637] Embodiment 18

[0638] Silicone-based N-maleyl β-alanine derivatives

[0639] In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer, 10 g (26.5 mmol epoxy groups) of an organosilicon diepoxide of the following structure was added.

[0640]

[0641] 4.95 g (26.5 mmol) of N-maleyl β-alanine according to Example 11, 0.23 g of trimethylamine and 60 g of 1,3-butanediol were mixed at room temperature under N2. The mixture was heated to 90°C for 12 hours. Afterwards, the mixture was cooled to room temperature and 1 The conversion of epoxy groups was determined by H NMR spectroscopy. The conversion of epoxy groups was 100%.

[0642] A reddish product consisting essentially of the following structure was obtained:

[0643]

[0644] in

[0645] x = 5.3, and

[0646] R is –OC(O)CH=CHC(O)NHCH2CH2C(O)OH or

[0647] –OC(O)CH2CH2NHC(O)CH=CHC(O)OH.

Claims

1. Use of a compound (B) or a salt thereof for treating the color and shape of hair, wherein the compound (B) has the following formula: Where R 5 is selected from hydroxyl or F and R 5 One or more of which are hydroxyl groups, wherein F is defined as -OC(O)-R 3 -C(O)OH, wherein the group F is bound to a carbon atom, provided that R 5 At least two of them are F; or Wherein compound (B) has the following formula: Where R 9 One of them is hydroxyl and R 9 One of the following groups and where F is defined as being selected from: -OC(O)-R 3 -C(O)OH, and where the group F is bound to the carbon atom, and the dotted line is the bond to the carbon atom, and among them R 3 is selected from a single bond or a linear or branched, saturated or unsaturated hydrocarbon radical optionally substituted by hydroxyl groups having up to 18 carbon atoms, optionally containing one or more radicals selected from: -NH- or -C(O)-, provided that R 3 Not -CH=CH-.

2. The use according to claim 1, wherein the group R 3 The optional substituents are selected from hydroxyl groups, and the number of substituents is up to 5.

3. The use according to claim 1 or 2, wherein compound (B) is a mixture of the following two isomers: wherein F is as defined in claim 1.

4. The use according to claim 1 or 2, wherein R 3 Derived from a dicarboxylic acid of the formula: Where R 3 As defined in claim 1.

5. The use according to claim 1 or 2, wherein F is selected from the following formula: wherein the dotted line in the above formula represents a bond to the oxygen atom, and wherein at least two groups F are present.

6. The use according to claim 1 or 2, wherein an aqueous composition comprising at least one compound (B) as defined in claim 1 or 2 is applied.

7. The use according to claim 6, wherein the aqueous composition comprises 0.05-30% by weight of at least one compound (B) as defined in claim 1, based on the total weight of the aqueous composition.

8. The use according to claim 6, wherein the aqueous composition optionally further comprises at least one surfactant.

9. The use according to claim 8, wherein the optional surfactant is selected from: cationic, nonionic, and anionic surfactants.

10. Use according to claim 8, wherein the optional surfactant is selected from hydrocarbon-based or silicone-based emulsifiers, each different from compound (B).

11. Use according to claim 8, wherein the optional surfactant is present in an amount of 0.05% to 15% by weight of the aqueous composition.

12. The use according to claim 6, wherein the aqueous composition comprises at least one additional additive selected from the group consisting of: l) organic diluents or solvents, m) protein, n) emollients or fatty substances, o) preservatives, p) Skin protection ingredients, q) conditioning agents, r) an oxidizing agent, s) a reducing agent, t) tannin, u) metal salts, v) other auxiliary agents selected from the group consisting of pH regulators, thickeners, lipids, amino acids, sugars, flavors, sunscreens, vitamins, pearlescent agents, gelling agents, trace elements, masking agents, antioxidants, moisturizers, anti-hair loss agents, anti-dandruff agents, propellants, ceramides, polymers, fillers, mother of pearl, colorants, and mixtures thereof, The proviso is that oxidizing agents and reducing agents are not present simultaneously in a given formulation.

13. The use according to claim 6, wherein the aqueous composition has the following composition: The percentages by weight relate to the weight of the entire aqueous composition.

14. The use according to claim 6, wherein the aqueous composition comprises at least one hair coloring agent.

15. The use according to claim 6, wherein the aqueous composition is a hair care composition.

16. The use according to claim 6, wherein the aqueous composition is a hair shampoo composition or a hair conditioning composition.

17. The use according to claim 6, wherein the aqueous composition is a hair strengthening composition.

18. The use according to claim 6, wherein the aqueous composition is a hair coloring or dyeing composition.

19. The use according to claim 6, wherein the aqueous composition is a hair color darkening composition.

20. The use according to claim 6, wherein the aqueous composition is selected from the group consisting of hair combability improving compositions, anti-frizz compositions, hair rinses and leave-in compositions.

21. The use according to claim 2, wherein the group R 3 The optional substituents are selected from hydroxyl groups, and the number of the substituents is 1-4.

22. The use according to claim 4, wherein R 3 Derived from a saturated or unsaturated aliphatic dicarboxylic acid optionally substituted by hydroxyl groups; or R 3 Derived from aliphatic or aromatic tricarboxylic acids, wherein R 3 Substituted with a carboxyl group (COOH).

23. The use according to claim 22, wherein the dicarboxylic acid is selected from oxalic acid, malic acid, succinic acid, gum acid, adipic acid, syrupylic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, brassic acid, tauric acid, glutaconic acid, citraconic acid, mesaconic acid, itaconic acid, tartronic acid, mesooxalic acid, malic acid, tartaric acid, oxaloacetic acid, α-hydroxy gum acid, arabinonic acid, acetone dicarboxylic acid, α-keto gum acid, and glucaric acid.

24. The use according to claim 22, wherein the tricarboxylic acid is selected from citric acid, isocitric acid, aconitic acid, propane-1,2,3-tricarboxylic acid, reaction products of carboxylic anhydrides with amino acids and amino acid derivatives.

25. Use according to claim 9, wherein the optional surfactant has an HLB value in the range of 1-20.

26. Use according to claim 8, wherein the optional surfactant is selected from betaine surfactants.

27. An aqueous composition as defined in any one of claims 6 to 20 and 25 to 26 for use in the colour treatment of hair.

28. An aqueous composition according to claim 27 for use in hair colour maintenance.

29. An aqueous composition according to claim 27 for use in hair colour enhancement.

30. The aqueous composition of claim 27 for use in darkening hair.

31. The aqueous composition of claim 27 for use in hair color protection.

32. A method for the colour treatment of hair comprising the steps of providing an aqueous composition as defined in any one of claims 6 to 20 and 25 to 26, and applying said aqueous composition to said hair.

33. A method for color treatment of hair comprising the steps of providing an aqueous composition as defined in any one of claims 6 to 20 and 25 to 26 and applying said aqueous composition to said hair, and the step of coloring the hair.

34. Compound (B) and its salt, wherein compound (B) has the following formula: Where R 5 is selected from hydroxyl or F and R 5 One or more of is hydroxyl, wherein F is defined as –O–C(O)–R 3 –C(O)OH, and wherein the group F is bound to a carbon atom, provided that R 5 At least two of them are F; or Wherein compound (B) has the following formula: Where R 9 One of them is hydroxyl and R 9 One of the following groups and where F is defined as being selected from: –O–C(O)–R 3 –C(O)OH, and where the group F is bound to the carbon atom, and the dotted line is the bond to the carbon atom, and R 3 is chosen from a single bond or a linear or branched, saturated or unsaturated hydrocarbon radical optionally substituted by hydroxyl groups having up to 18 carbon atoms, optionally comprising one or more radicals selected from: -NH- and -C(O)-, The condition is R3 Not –CH=CH–.

35. The compound according to claim 34, which is a mixture of the following two isomers: wherein F is as defined in claim 34.

36. The compound (B) according to claim 35, wherein the two compounds are in a molar ratio of 1:

1.

37. The compound according to claim 34, wherein R 3 Selected from single bonds and straight-chain or branched saturated or unsaturated hydrocarbon groups having up to 12 carbon atoms.

38. The compound according to claim 34, wherein R 3 Selected from single bonds and straight-chain or branched saturated or unsaturated hydrocarbon groups having up to 10 carbon atoms.

39. The compound according to claim 34, wherein R 3 Derived from a dicarboxylic acid of the formula: Where R 3 As defined in claim 1.

40. The compound according to claim 34, wherein F is selected from the following formula: wherein the dotted line in the above formula represents a bond to the oxygen atom, and wherein at least two groups F are present.

41. The compound according to claim 39, wherein R 3 Derived from a saturated or unsaturated aliphatic dicarboxylic acid optionally substituted by hydroxyl groups; or R 3 Derived from aliphatic tricarboxylic acids, wherein R 3 Substituted with a carboxyl group (COOH).

42. The compound of claim 39, wherein the dicarboxylic acid is selected from oxalic acid, malic acid, succinic acid, gum acid, adipic acid, syrupylic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, brassic acid, tauric acid, glutaconic acid, citraconic acid, mesaconic acid, itaconic acid, tartronic acid, mesooxalic acid, malic acid, tartaric acid, oxaloacetic acid, α-hydroxyglucoic acid, arabinonic acid, acetone dicarboxylic acid, α-ketoglucoic acid, and glucaric acid.

43. The compound of claim 39, wherein the tricarboxylic acid is selected from the group consisting of citric acid, isocitric acid, aconitic acid, propane-1,2,3-tricarboxylic acid, reaction products of carboxylic acid anhydrides with amino acids and amino acid derivatives.

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