DE202018006763U1 - Composition for straightening keratin fibers - Google Patents

Abstract

Composition for straightening keratin fibres, preferably human keratin fibres, more preferably human hair, having a pH of 4 or less and comprising
- glyoxylic acid and/or its hydrate(s) and/or its salt(s),
- Polysilicone-29.

Description

field of invention

The present invention relates to the field of straightening keratin fibers, preferably human keratin fibers, more preferably human hair. Furthermore, a method for smoothing the keratin fibers and a multi-part kit is disclosed.

Background of the Invention

Changing the shape of hair has always been en vogue. Long, straight hair was already popular in ancient Egyptian times. Women who were not blessed with this type of natural hair used fire-heated iron plates to style their hair into the desired shape. This procedure often resulted in severe burns to the face and hands. Straightening only became more professional at the beginning of the 19th century with the invention of hair tongs by Marcel Grateau. These days, hot tools like curling irons or straighteners are more popular than ever. They have become the focus of consumers both in the salon and in the mass market. These tools give satisfactory results because they work at very high temperatures, up to 230°C. When dry hair comes into contact with the hot straightening iron while applying reasonable pressure, the hair shape can be fixed for a period of time until the moisture restores it to its original state. Unfortunately, application of such a hot temperature leads to hair damage and hence poor hair feel after use.

The prior art has primarily addressed the durability problem by making available non-reductive methods of straightening hair. WO2011104282 and WO2012010351 disclose hair straightening methods that use glyoxylic acid treatments and combine them with a heating step. This method leads to good smoothing results, but has some disadvantages. Due to the high concentration of glyoxylic acid needed to straighten very curly hair, there is always a risk of scalp or skin irritation. In addition, the treatment has an undesirable impact on the client's natural hair color, often resulting in color shifting and/or undesirable lightening. Therefore, it is not uncommon to combine the smoothing routine with an oxidative coloring routine, as in WO2014067702 disclosed.

In FR2997845 and FR3044903 discloses hair treatment compositions and methods that utilize acids and monomeric silanes in combination with a heating step. In FR2997847 discloses a combination of glyoxylic acid with aminosilicones and a heating step. However, the aforementioned prior art is silent on Polysilicone-29.

Despite the attempts of the prior art, there is a great need for products that allow for more effective smoothing of keratin fibers while reducing hair damage, leaving a pleasant hair feel after application and enhancing hair shine, and which do not have an adverse effect on the customer's natural hair color .

To date, the prior art has not fully achieved the aforesaid goals.

Summary of the Invention

The inventors of the present invention have unexpectedly found that a combination of glyoxylic acid and/or its various forms with polysilicone-29 has a superior hair straightening effect compared to either component used alone, while maintaining a healthy condition of the hair. resulting in a very good cosmetic feel of the treated keratin fibers. It has also been found that there is no visually perceptible color shift in the keratin fibers after the treatment.

• - Glyoxylsäure und/oder ihr(e) Hydrat(e) und/oder ihr(e) Salz(e) und
• - Polysilikon-29.

Therefore, the first object of the present invention is to provide a composition for straightening keratin fibers, preferably human keratin fibers, more preferably human hair, having and comprising a pH of 4 or less

• - glyoxylic acid and/or its hydrate(s) and/or its salt(s) and
• - Polysilicone-29.

The second object of the present invention is a two-part composition comprising parts A and B intended to be stored separately and mixed immediately before application to the keratin fibers,
wherein part A comprises glyoxylic acid and/or its hydrate(s) and/or its salt(s) having a pH of less than 4 and part B comprises polysilicone-29 having a pH in the range of 2 to 10 included.

1. a) gegebenenfalls Waschen der Keratinfasern und/oder Trocknen der Keratinfasern,
2. b) Aufbringen der Zusammensetzung und/oder zweiteiligen Zusammensetzung wie oben definiert auf Keratinfasern,
3. c) Belassen der Zusammensetzung auf den Keratinfasern für 1 min bis 120 min, vorzugsweise für einen Zeitraum im Bereich von 2 min bis 60 min, stärker bevorzugt im Bereich von 2 min bis 30 min, weiter stärker bevorzugt im Bereich von 2 Minuten bis 10 Minuten,
4. d) gegebenenfalls Abspülen der Keratinfasern,
5. e) Trocknen der Keratinfasern,
6. f) Behandeln der Keratinfasern mit einem Glätteisen mit einer Oberflächentemperatur von 180 °C ± 50 °C, vorzugsweise im Bereich von 170 °C bis 200 °C,
7. g) gegebenenfalls Abspülen und/oder Waschen der Keratinfasern und/oder Trocknen der Keratinfasern.

The third subject of the present invention is a method for the semi-permanent straightening of keratin fibers, preferably human keratin fibers, more preferably human hair, characterized in that it comprises the steps:

1. a) optionally washing the keratin fibers and/or drying the keratin fibers,
2. b) applying the composition and/or two-part composition as defined above to keratin fibers,
3. c) leaving the composition on the keratin fibers for 1 min to 120 min, preferably for a period in the range 2 min to 60 min, more preferably in the range 2 min to 30 min, even more preferably in the range 2 min to 10 min ,
4. d) optionally rinsing off the keratin fibers,
5. e) drying the keratin fibers,
6. f) treating the keratin fibers with a straightening iron with a surface temperature of 180°C ± 50°C, preferably in the range from 170°C to 200°C,
7. g) optionally rinsing and/or washing the keratin fibers and/or drying the keratin fibers.

The time range for leaving the composition on the keratinic fibers in step c) from 1 to 10 minutes is particularly preferred for home use of the composition, whereas the longer process times are preferred for salon use.

It is preferred that the weight ratio of keratin fibers to composition in step b) ranges from 0.5:2 to 2:0.5.

It is also preferred that steps a) to g) are repeated from above with a period of 8 hours and 72 hours between each complete process run.

• a) gegebenenfalls Waschen der Keratinfasern und/oder Trocknen der Keratinfasern,
• b) Auftragen einer Zusammensetzung mit einem pH-Wert von 4 oder weniger, die Glyoxylsäure und/oder ihr(e) Hydrat(e) und/oder ihr(e) Salz(e) umfasst,
• c) Belassen der Zusammensetzung auf den Keratinfasern für 1 min bis 120 min, vorzugsweise für einen Zeitraum im Bereich von 2 min bis 60 min, stärker bevorzugt im Bereich von 2 min bis 30 min, weiter stärker bevorzugt im Bereich von 2 Minuten bis 10 Minuten,
• d) Abspülen der Keratinfasern,
• e) Auftragen einer Zusammensetzung mit einem pH-Wert im Bereich von 2 bis 10, die Polysilicone-29 umfasst,
• f) gegebenenfalls Abspülen der Keratinfasern,
• g) Trocknen der Keratinfasern,
• h) Behandeln der Keratinfasern mit einem Glätteisen mit einer Oberflächentemperatur von 180 °C ± 50 °C, vorzugsweise im Bereich von 170 °C bis 200 °C,
• i) gegebenenfalls Abspülen und/oder Waschen der Keratinfasern und/oder Trocknen der Keratinfasern.

Another subject of the present invention is a method for semi-permanently straightening keratin fibers, preferably human keratin fibers, particularly preferably human hair, characterized in that it comprises the steps:

• a) optionally washing the keratin fibers and/or drying the keratin fibers,
• b) applying a composition having a pH of 4 or less and comprising glyoxylic acid and/or its hydrate(s) and/or its salt(s),
• c) leaving the composition on the keratin fibers for 1 min to 120 min, preferably for a period in the range 2 min to 60 min, more preferably in the range 2 min to 30 min, even more preferably in the range 2 min to 10 min ,
• d) rinsing of the keratin fibers,
• e) applying a composition having a pH in the range of 2 to 10 comprising polysilicone-29,
• f) optionally rinsing off the keratin fibers,
• g) drying the keratin fibers,
• h) treating the keratin fibers with a straightening iron with a surface temperature of 180°C ± 50°C, preferably in the range from 170°C to 200°C,
• i) optionally rinsing and/or washing the keratin fibers and/or drying the keratin fibers.

The time range for leaving the composition on the keratinic fibers in step c) from 1 to 10 minutes is particularly preferred for home use of the composition, whereas the longer process times are preferred for salon use.

It is convenient that steps a) to g) are repeated from above with a period of 8 hours and 72 hours between each complete process run.

It is preferred that the weight ratio of keratin fibers to the compositions in steps b) and e) ranges from 0.5:2 to 2:0.5.

Yet another object of the present invention is a multi-part kit comprising the composition and/or two-part composition as defined above and a keratin fiber straightening device, preferably a hair straightener.

Detailed description of the invention

glyoxylic acid

The composition comprises glyoxylic acid and/or its hydrate(s) and/or its salt(s) in a total concentration ranging from 0.1 to 20% by weight, preferably ranging from 0.2 to 10% by weight, more preferably in the range from 0.25 to 5% by weight, more preferably in the range from 0.35 to 5% by weight, calculated on the total composition. The concentration ranging between 5 and 20% by weight of glyoxylic acid and/or its hydrate(s) and/or its salt(s) is particularly suitable for the hairdressing salon application carried out by a person skilled in the art , whereas the 0.1% to 5% by weight concentration of the compounds are suitable for consumer products for home use.

Suitable concentration ranges are shown in Examples 3-7.

Polysilicone-29

Polysilicone-29 is the INCI name of a polymeric silane offered for sale by Momentive Performance Materials Inc.

In aspects of the present invention in which the polymeric silane and glyoxylic acid and/or its hydrates and/or its salts are present in the same one-part composition, the pH is less than 7, preferably 4 or less, more preferably 4 or less Range from pH 1 to 3.5. Suitable pH ranges are shown in Example 3.

In another aspect of the present invention, Polysilicone-29 is kept separate from the composition comprising glyoxylic acid and/or its hydrate(s) and/or its salt(s) and the compositions comprising the compounds include are mixed just prior to their use. The presence of a mixing step prior to application to keratin fibers for this embodiment allows for greater flexibility in the mixing ratios of the two compositions.

The latter aspect is then available as a two-part composition according to the second aspect of the present invention. Example 8 illustrates this aspect.

For this aspect, the pH of the composition comprising glyoxylic acid and/or its salts and/or its hydrates is less than 7, preferably 4 or less, more preferably in the range pH 1 to 3.5. For the composition part comprising polysilicone-29, the pH can range from 2-10. However, after mixing both compositions, the resulting pH must be in the range of less than 7, preferably 4 or less, more preferably in the range of pH 1 to 3.5 to fully utilize the smoothing potential of glyoxylic acid.

In another aspect of the present invention, Polysilicone-29 is kept separate from the composition comprising glyoxylic acid and/or its hydrate(s) and/or its salt(s) and is also subsequently applied to keratin fibers . According to this embodiment, the composition comprising glyoxylic acid and/or its hydrate(s) and/or its salt(s) is applied first and then the composition comprising polysilicone-29 is applied without one Rinsing step between applications applied to keratin fibers Compositions. Examples 2, 6 and 7 illustrate this embodiment. The pH ranges are similar to those disclosed for the two part composition.

The skilled reader will note that without the rinsing step, the compositions comprising polysilicone-29 and glyoxylic acid are formed on the keratin fibers.

In yet another aspect of the present invention, the Polysilicone-29 is kept separate from the composition comprising glyoxylic acid and/or its hydrate(s) and/or its salt(s), and also subsequent to the applied keratin fibers. According to this embodiment, the composition comprising glyoxylic acid and/or its hydrate(s) and/or its salt(s) is applied first and then the composition comprising polysilicone-29 is applied to keratin fibers Compositions applied with a rinsing step between applications. The pH ranges are similar to those disclosed for the two part composition.

Regardless of the aspects listed above, the composition comprising Polysilicone-29 comprises this compound in a total concentration in the range of 0.01 to 10% by weight, preferably in the range of 0.02 to 8% by weight, more preferably in the range of 0.05 to 6% by weight, more preferably in the range 0.1 to 2% by weight, calculated on the total composition.

Also independently of the aspects listed above, the weight ratio of glyoxylic acid and/or its hydrate(s) and/or its salt(s) to Polysilicone-29 applied to keratin fibers ranges from 10 to 0.1 . This weight ratio applies to the embodiments in which glyoxylic acid and/or its hydrates and/or its salts and polysilicone-29 are present in a composition, but also to the embodiments in which both compounds are kept separate before their application to keratin fibers .

Cosmetic composition forms

Suitable cosmetic forms of the compositions of the present invention are solutions, dispersions, thickened gels and/or emulsions and foams.

thickening polymers

To produce a thickened gel, the composition comprises a thickening agent, preferably a thickening polymer, more preferably an associative and/or non-associative thickening polymer.

It should be noted that the thickening polymer must have the property of thickening the composition under low pH conditions, namely at pH 4 or less. Thus, suitable thickeners will provide a solution/gel with a viscosity of at least 500 mPas at 25°C, measured with a Brookfield viscometer and spindle number 5, at a pH of 4 or less. More preferably, suitable thickening polymers are also resistant to partial neutralization of glyoxylic acid and/or its hydrate or hydrates and/or its salts.

Suitable thickening polymers are carbohydrate-based non-associative thickening polymers, more preferably they are selected from xanthan gum and/or dehydroxanthan gum and hydroxyethyl cellulose.

The concentration of thickening agents in the composition according to the invention is in the range of 0.1 to 5% by weight, preferably 0.2 to 3% by weight, calculated on the total composition.

The gel form of the compositions of the present invention is illustrated in Examples 4, 5, 7 and 8.

It should be noted that such thickened gels may comprise one or more hydrophobic compound(s) in a concentration of less than 2% by weight calculated on the total amount of the composition. Such an inventive subject matter is illustrated in Example 4.

hydrophobic compounds

If the composition of the present invention is presented as an emulsion or a gel, the composition comprises one or more hydrophobic compound(s), preferably selected from C ₁₂ to C ₂₂ fatty alcohols, fatty acid esters with a C ₁₂ to C ₂₂ fatty acid , with which is esterified a linear or branched, saturated or unsaturated C ₃ to C ₁₈ fatty alcohol, natural and/or vegetable oils, hydrocarbon-based compounds and/or mixtures thereof.

Suitable C ₁₂ to C ₂₂ fatty alcohols are lauryl alcohol, tridecyl alcohol, myristyl alcohol, pentadecyl alcohol, cetyl alcohol, palmitoleyl alcohol, heptadecyl alcohol, stearyl alcohol, nonadecyl alcohol, arachidyl alcohol, behenyl alcohol and/or mixtures thereof, especially cetearyl alcohol.

Suitable fatty acid esters consisting of linear or branched, saturated or unsaturated fatty acids with C ₁₂ to C ₂₂ esterified with linear or branched primary alcohols with C ₃ to C ₁₈ are octyl palmitate, isocetyl palmitate, isopropyl palmitate, octyl stearate, oleyl oleate and myristyl myristate, and their mixtures.

Suitable petrolatum-based compounds are liquid paraffins, especially paraffinum perliquidum and paraffinum subliquidum, and mineral oil, especially white mineral oil.

Suitable natural and/or vegetable oils are olive oil, almond oil, avocado oil, wheat germ oil and castor oil.

The total concentration of these hydrophobic compounds to form emulsions ranges from 0.1 to 20% by weight, preferably 1 to 15% by weight and more preferably 2 to 10% by weight, calculated on the total amount of the composition.

Emulsions are illustrated in Examples 5, 6 and 7.

surfactants

With regard to Examples 4-8, the composition may further comprise surfactant(s), preferably a nonionic and/or anionic and/or cationic and/or amphoteric/zwitterionic surfactant.

Suitable anionic surfactants are alkyl sulphate or preferably ethoxylated alkyl ether sulphate surfactants and/or mixtures thereof having an alkyl chain length of _C10 to _C22 .

Suitable surfactants are laureth sulfate, coceth sulfate, pareth sulfate, capryth sulfate, myreth sulfate, oleth sulfate, deceth sulfate, trideceth sulfate, coco sulfate, C ₁₀ -C ₁₆ alkyl sulfate, C ₁₁ -C ₁₅ alkyl sulfate, C ₁₂ -C ₁₈ alkyl sulfate, C ₁₂ - C ₁₅ alkyl sulfate, C ₁₂ -C ₁₆ alkyl sulfate, C ₁₂ -C ₁₃ alkyl sulfate, lauryl sulfate, myrystyl sulfate, palm kernel sulfate, cetearyl sulfate, cetyl sulfate, decyl sulfate, oleyl sulfate, behenyl sulfate and/or salts thereof. All of the aforesaid anionic surfactants may or may not be ethoxylated to varying degrees.

Other suitable anionic surfactants useful in the invention are α-olefin sulphonates and/or their salts and in particular alkali metal salts of sulfosuccinic acid half esters, for example the disodium salt of monooctyl sulfosuccinate and alkali metal salts of long chain monoalkyl ethoxy sulfosuccinates.

worin R₁₆ eine lineare oder verzweigte, gesättigte oder ungesättigte Alkylkette mit C₁₁ bis C₂₁ ist, R₁₇ lineares oder verzweigtes Alkyl oder lineares oder verzweigtes Hydroxyalkyl mit C₁ bis C₄ ist und R₁₈ eine lineare oder verzweigte Polyhydroxyalkylkette mit C₃ bis C₁₂ und 3 bis 10 Hydroxylgruppen ist.Suitable nonionic surfactants are N-alkylpolyhydroxyalkylamide type surfactants according to the following general formula:

wherein R ₁₆ is a linear or branched, saturated or unsaturated alkyl chain of C ₁₁ to C ₂₁ , R ₁₇ is linear or branched alkyl or linear or branched hydroxyalkyl of C ₁ to C ₄ and R ₁₈ is a linear or branched polyhydroxyalkyl chain of C ₃ to C ₁₂ and 3 to 10 hydroxy groups.

Such compounds are present in cosmetic compositions WO96/27366 disclosed and their synthesis is in US1985424 , US2016962 , US2703798 and WO92/06984 disclosed.

wobei R₁₆ die gleiche Bezeichnung wie oben für die allgemeine Struktur von Tensiden vom N-Alkylpolyhydroxyalkylamid-Typ hat. Die oben angegebenen bevorzugten Tenside sind als N-Methyl-N-acylglucamide bekannt.The preferred N-alkylpolyhydroxyalkylamide type surfactants have the following structure:

where R ₁₆ has the same designation as above for the general structure of N-alkylpolyhydroxyalkylamide-type surfactants. The preferred surfactants identified above are known as N-methyl-N-acylglucamides.

The most preferred N-alkyl polyhydroxyalkylamide type surfactants are selected from lauroyl/myristoylmethyl glucamide and coco methyl glucamide.

Other suitable nonionic surfactants are alkyl polyglycosides according to the general structure: R ₂₃ O (R ₂₄ O) _t Z _x wherein Z denotes a carbohydrate of C ₅ to C ₆ , R ₂₃ is an alkyl group of C ₈ to C ₁₈ , R ₂₄ is methyl, ethyl or propyl, t ranges from 0 to 10 and x ranges from 1 to 5 . Suitable compounds according to this structure are C ₉ -C ₁₁ -alkyl polyglycoside, which are EP-A 70 074 and JP 2015-123019A disclosed structures.

The preferred compounds according to the above structure are decyl glucoside, lauryl glucoside and coco glucoside and the most preferred is decyl glucoside.

Suitable examples of nonionic surfactants are fatty alcohol ethoxylates of the following general structure R ₂₅ (OCH ₂ CH ₂ ) _{n 4} OH wherein R ₂₅ is a straight or branched, saturated or unsaturated alkyl chain, which may be synthetic or natural, with a C chain length ranging from 8 to 40, preferably 9 to 30 and more preferably 9 to 24, and n4 is a number in the range from is 5 to 40, preferably 9 to 30.

Non-limiting suitable examples of the fatty alcohol ethoxylates are C9-11 Pareth-6, C9-11 Pareth-8, C9-15 Pareth-8, C11-13 Pareth-9, C11-13 Pareth-10, C11-15 -Pareth -5, C11-15 Pareth-7, C11-15 Pareth-9, C11-15 Pareth-12, C11-15 Pareth-15, C11-15 Pareth-20, C11-15 Pareth-30, C11-15 Pareth-40, C11-21 Pareth-10, C12-13 Pareth-5, C12-13 Pareth-6, C12-13 Pareth-7, C12-13 Pareth-9, C12-13 Pareth-10, C12-13 Pareth -15 , C12-13 Pareth-23, C12-14 Pareth-5, C12-14 Pareth-7, C12-14 Pareth-9, C12-14 Pareth-11, C12-14 Pareth-12, C12-15 Pareth- 5, C12-15 Pareth-7, C12-15 Pareth-9, C12-15 Pareth-10, C12-15 Pareth-11, C12-15 Pareth-12, C12-16 Pareth-5, C12-16 Pareth-7 , C12-16 Pareth-9, C13-15 Pareth-21, C14-15 Pareth-7, C14-15 Pareth-8, C14-15 Pareth-11, C14-15 Pareth-12, C14-15 Pareth-13, C20-22 Pareth-30, C20-40 Pareth-10, C20-40 Pareth-24, C20-40 Pareth-40, C20-40 Pareth-95, C22-24 Pareth-33, Beheneth-5, Beheneth-10, Beheneth-15, Beheneth-20, Beheneth-25, Beheneth-30, Ceteareth-5, Ceteareth-6 , Ceteareth h-7, Ceteareth-10, Ceteareth-11, Ceteareth-12, Ceteareth-15, Ceteareth-20, Ceteareth-25, Ceteareth-30, Ceteareth-35, Ceteareth-40, Laureth-5, Laureth-10, Laureth- 15, Laureth-20, Laureth-25, Laureth-30, Laureth-40, Myreth-5, Myreth-10, Ceteth-5, Ceteth-10, Ceteth-15, Ceteth-20, Ceteth-25, Ceteth- 30, Ceteth-40, Oleth-5, Oleth-10, Oleth-15, Oleth-20, Oleth-25, Oleth-30, Oleth-40, Steareth-5, Steareth-10, Steareth-15, Steareth-20, Steareth-25, Steareth-30, Steareth-35 and Steareth-40. They can also be present in the compositions as a mixture of more than one surfactant.

Other suitable nonionic surfactants are polypropylene glycol ethers of fatty alcohols according to the general structure R25 _{( OCH2 -CH2 -CH2} ) _n5 OH wherein R ₂₅ is straight-chain or branched, saturated or unsaturated fatty alcohol, which can be synthetic or natural, with a C-chain length in the range of 8 to 40, preferably 9 to 30 and more preferably 9 to 24 and n5 is a number in the range of 1 to 40, preferably 3 to 30.

Suitable non-limiting examples are PPG-3 caprylyl ether, PPG-5 caprylyl ether, PPG-10 caprylyl ether, PPG-10 cetyl ether, PPG-20 cetyl ether, PPG-28 cetyl ether, PPG-30 cetyl ether, PPG-7 lauryl ether, PPG-10 lauryl ether, PPG-10 oleyl ether, PPG-20 oleyl ether, PPG-23 oleyl ether, PPG-30 oleyl ether, PPG-11 stearyl ether, and PPG-15 stearyl ether.

Other suitable nonionic surfactants are polyethylene glycol fatty acid esters having the following general structure R26 C(O)( _{OCH2 CH2 ) n6} OH wherein R ₂₆ is a straight or branched chain, saturated or unsaturated alkyl group, which may be synthetic or natural, having a C chain length ranging from 7 to 39, preferably 9 to 29 and more preferably 9 to 23, and n6 is a number ranging from is 5 to 40, preferably 9 to 30.

Suitable non-limiting examples are PEG-8 Behenate, PEG-8 Caprate, PEG-8 Caprylate, PEG-5 Cocoate, PEG-8 Cocoate, PEG-9 Cocoate, PEG-10 Cocoate, PEG-15 Cocoate, PEG-6 Isopalmitate, PEG-6 Isostearate, PEG-8 Isostearate,
PEG-9 isostearate, PEG-10 isostearate, PEG-12 isostearate, PEG-20 isostearate, PEG-30 isostearate, PEG-40 isostearate, PEG-6 laurate, PEG-8 laurate, PEG- 9-laurate, PEG-10 laurate, PEG-12 laurate, PEG-14 laurate, PEG-20 laurate, PEG-30 laurate, PEG-8 myristate, PEG-20 myristate, PEG-5 oleate, PEG-6 oleate, PEG-7 Oleate, PEG-8 Oleate, PEG-9 Oleate, PEG-10 Oleate, PEG-11 Oleate, PEG-12 Oleate, PEG-15 Oleate, PEG-20 Oleate, PEG-30 Oleate, PEG-32 Oleate, PEG-6 Palmitate, PEG-18 Palmitate, PEG-20 Palmitate, PEG-5 Stearate, PEG-6 Stearate, PEG-7 Stearate, PEG-8 Stearate, PEG-9 stearate, PEG-10 stearate, PEG-12 stearate, PEG-14 stearate, PEG-15 stearate, PEG-20 stearate, PEG-25 stearate, PEG-30 stearate, PEG- 35 stearate and PEG-40 stearate.

Other suitable nonionic surfactants are polypropylene glycol fatty acid esters having the following general structure R ₂₇ C(O) (OCH ₂ -CH ₂ -CH ₂ ) _n8 OH wherein R ₂₇ is a straight-chain or branched, saturated or unsaturated alkyl group, which may be synthetic or natural, with a C-chain length ranging from 7 to 39, pr preferably 9 to 29 and more preferably 9 to 23, and n8 is a number in the range of 1 to 40, preferably 9 to 30.

Suitable non-limiting examples are PPG-15 isostearate, PPG-9 laurate, PPG-26 oleate and PPG-36 oleate.

Other suitable nonionic surfactants are polyethylene glycol and polypropylene glycol ethers of fatty alcohols having the following general structure _R28 ( _{OCH2 -CH2 -CH2} ) _n9 ( _{OCH2 CH2} ) _n10 OH wherein R ₂₈ is a straight-chain or branched, saturated or unsaturated alkyl group, which may be synthetic or natural, with a C-chain length in the range of 7 to 39, preferably 9 to 29 and more preferably 9 to 23, and n9 and n10 equal or can be different and are a number ranging from 1 to 40.

Other suitable nonionic surfactants are ethoxylated vegetable oils. Well-known and frequently used examples are ethoxylated castor oil such as PEG-40 hydrogenated castor oil or PEG-60 hydrogenated castor oil.

Suitable cationic surfactants have one or more positively charged groups at pH 4 or less and are selected from cationic and/or cationisable and/or zwitterionic/amphoteric surfactants.

wobei R₁ eine gesättigte oder ungesättigte, verzweigte oder lineare Alkylkette mit C₈-C₂₂ oder ist RsCO NH (CH₂) n wobei R₅ eine gesättigte oder ungesättigte, verzweigte oder lineare Alkylkette mit C₇-C₂₁-Atomen ist und n einen typischen Wert von 1-4 hat oder R₆COO (CH₂) n wobei R₆ eine gesättigte oder ungesättigte, verzweigte oder lineare Alkylkette mit C₇-C₂₁-Atomen ist und n einen typischen Wert von 1-4 hat, und
R₂ ist eine ungesättigte oder gesättigte, verzweigte oder lineare Alkylkette mit C₁-C₂₂-Atomen oder RsCO NH (CH₂) n oder R₆COO (CH₂)_n wobei R₅, R₆ und n die gleichen wie oben sind.Suitable cationic surfactants have a quaternary ammonium structure according to the following general structure

wherein R ₁ is a saturated or unsaturated, branched or linear alkyl chain with C ₈ -C ₂₂ or RsCO NH (CH ₂ ) n where R ₅ is a saturated or unsaturated, branched or linear alkyl chain with C ₇ -C ₂₁ atoms and n has a typical value of 1-4 or R ₆ COO (CH ₂ ) n wherein R ₆ is a saturated or unsaturated, branched or linear alkyl chain with C ₇ -C ₂₁ atoms and n has a typical value of 1-4, and
R ₂ is an unsaturated or saturated, branched or linear alkyl chain with C ₁ -C ₂₂ atoms or RsCO NH (CH ₂ ) n or R ₆ COO (CH ₂ ) _n where R ₅ , R ₆ and n are the same as above.

R ₃ and R ₄ have an alkyl chain of C ₁ to C ₄ and X ^- is typically chloride, bromide or methosulfate.
Typical examples of these ingredients are
Cetyltrimethylammonium chloride, Stearyltrimonium chloride, Dipalmitoyldimonium chloride, Distearyldimethylammonium chloride, Stearamidopropyltrimethylammonium chloride,
dioleoylethyldimethylammonium methosulfate,
dioleoylethylhydroxyethylmonium methosulfate,
Behenyltrimethylammonium chloride and/or mixtures thereof.

Suitable cationizable surfactants are surfactants that bear one or more chemical group(s) that is/are nonionic at least sometime above pH 4, but which is/are positively charged at pH 4 or less. Such groups are, for example, primary, secondary and tertiary amino groups.

wobei R₁₁ eine gesättigte oder ungesättigte, gerade oder verzweigte Alkylkette mit C₁₁ bis C₂₁ ist, R₁₂ eine gerade oder verzweigte Alkylkette mit C₁ bis C₆ ist, R₁₃ und R¹⁴ gleich oder verschieden sein können, ausgewählt aus H und gerader oder verzweigter Alkylkette mit C₁ bis C₄.Other suitable cationizable surfactants are known as alkylamidoalkylamine surfactants and conform to the following general structure

wherein R ₁₁ is a saturated or unsaturated, straight or branched alkyl chain with C ₁₁ to C ₂₁ , R ₁₂ is a straight or branched alkyl chain with C ₁ to C ₆ , R ₁₃ and R ¹⁴ can be the same or different, selected from H and straight or branched alkyl chain with C ₁ to C ₄ .

Suitable compounds according to this definition are, for example, cocamidopropyldimethylamine, stearamidopropyldimethylamine, behenamidopropyldimethylamine.

und/oder

worin R₁₅ eine gerade oder verzweigte, gesättigte oder ungesättigte, substituierte oder unsubstituierte Alkylkette mit einer Kohlenstoffzahl von C₁₀ bis C₂₂ ist, vorzugsweise R15 eine gerade Alkylkette mit einer Kohlenstoffzahl von C₁₀ bis C₁₆ ist, A eine gerade Alkylkette mit a ist Kohlenstoffzahl von C₁ bis C₆ oder eine verzweigte Alkylkette mit einer Kohlenstoffzahl von C₃ bis C₆, vorzugsweise ist A eine lineare Alkylkette mit einer Kohlenstoffzahl von C₃ und B ist eine Amid- oder eine Estergruppe.Other suitable surfactants having one or more positively charged groups at a pH below 7 are amphoteric/zwitterionic surfactants. Amphoteric/zwitterionic surfactants can be selected from compounds according to the general structure(s)

and or

wherein R ₁₅ is a straight or branched, saturated or unsaturated, substituted or unsubstituted alkyl chain having a carbon number from C ₁₀ to C ₂₂ , preferably R 15 is a straight alkyl chain having a carbon number from C ₁₀ to C ₁₆ , A is a straight alkyl chain with a Carbon number from C ₁ to C ₆ or a branched alkyl chain with a carbon number from C ₃ to C ₆ , preferably A is a linear alkyl chain with a carbon number from C ₃ and B is an amide or an ester group.

Suitable compounds are known as hydroxysultaine surfactants such as cocoamidopropyl hydroxysultaine, laurylamidopropyl hydroxysultaine, erucamidopropyl hydroxysultaine, lauryl hydroxysultaine and cocoyl hydroxysultaine.

Other suitable amphoteric/zwitterionic surfactants are of the betaine type. Suitable compounds can be selected from alkyl betaines and/or alkyl amido betaines. A preferred compound selected from alkyl betaines is lauryl betaine. A preferred compound selected from alkylamidobetaines is cocamidopropyl betaine.

It should be noted that those skilled in the art can combine surfactants from the above classes to create suitable surfactant mixtures.

The preferred surfactant(s) having one or more positively charged group(s) at pH 4 or less of the composition according to the present invention is/are selected from quaternary ammonium surfactant(s), alkylamidoalkylamine surfactant(s). ).), amphoteric/zwitterionic surfactants and/or mixtures thereof.

The total concentration of surfactants in the composition of the present invention is in the range of 0.05% to 25% by weight, preferably 0.1% to 15% by weight, more preferably in the range of 0. 2% by weight to 8% by weight calculated on the total of the composition.

cationic polymers

The composition of the present invention may comprise one or more cationic conditioning polymers other than polysilicone-29.

Suitable cationic polymers are those best known by their INCI category designation Polyquaternium.

Typical examples are Polyquaternium 1, Polyquaternium 2, Polyquaternium 4, Polyquaternium 5, Polyquaternium 6, Polyquaternium 7, Polyquaternium 8, Polyquaternium 9, Polyquaternium 10, Polyquaternium 11, Polyquaternium 12, Polyquaternium 13, Polyquaternium 14, Polyquaternium 15, Polyquaternium 16, Polyquaternium 17, Polyquaternium 18, Polyquaternium 19, Polyquaternium 20, Polyquaternium 22, Polyquaternium 24, Polyquaternium 27, Polyquaternium 28, Polyquaternium 29, Polyquaternium 30, Polyquaternium 31, Polyquaternium 32, Polyquaternium 33, Polyquaternium 34, Polyquaternium 35 and Polyquaternium 36, Poly-37 Polyquaternium 39, Polyquaternium 42, Polyquaternium 43, Polyquaternium 44, Polyquaternium 45, Polyquaternium 46, Polyquaternium 47, Polyquaternium 48, Polyquaternium 49, Polyquaternium 50, Polyquaternium 51, Polyquaternium 52, Polyquaternium 53, Polyquaternium 54, Polyquaternium 556, Polyquaternium 57 58, Polyquaternium 59, Polyqu Aternium 60 , Polyquaternium 61, Polyquaternium 62, Polyquaternium 63, Polyquaternium 64, Polyquaternium 65, Polyquaternium 66, Polyquaternium 67, Polyquaternium 68, Polyquaternium 69, Polyquaternium-70, Polyquaternium 71, Polyquaternium 72, Polyquaternium 73, Polyquaternium 74, Polyquaternium 775, Polyquaternium 6 , Polyquaternium 77, Polyquaternium 78, Polyquaternium-79, Polyquaternium 80, Polyquaternium 81, Polyquaternium 82, Polyquaternium 83, Polyquaternium 84, Polyquaternium 85, Polyquaternium 86 and Polyquaternium 87.

It has also been found that in particular those of the cationic cellulose type, known as Polymer JR type from Amerchol, such as Polyquaternium 10, or cationic galactomannans, such as cationic guar gum, known under the trade name Jaguar from Rhone-Poulenc, which chemically are, for example, guar hydroxypropyltrimonium chloride and cationic Gum tara and its derivatives, known by the INCI name Caesalpinia spinosa Hydroxypropyltrimonium Chloride, are preferred. Furthermore, chitosan and chitin can also be contained in the compositions as cationic natural polymers. In this context, reference is also made to the in DE 25 21 960 , DE 28 11 010, 30 44 738 and DE 32 17 059 disclosed cationic polymers and in EP-A 337 354 products described on pages 3 to 7. Mixtures of different cationic polymers can also be used.

The most preferred cationic polymers are those of cationic cellulose derivatives, cationic guar gum derivatives, cationic Caesalpinia spinosa gum derivatives, Polyquaternium 6, Polyquaternium 7, Polyquaternium 10, Polyquaternium 37, Polyquaternium 67 and Polyquaternium 70.

The cationic polymers also include the EP-A 524 612 and EP-A 640 643 described quaternized products of graft polymers of organopolysiloxanes and polyethyloxazolines.

Compositions may contain cationic polymer at a total concentration of from 0.01% to 5%, preferably from 0.02% to 4%, more preferably from 0.05% to 3%, and most preferably from 0.1% to 2% by weight. 5% by weight calculated on the total amount of the composition.

Example 5 illustrates this point of view.

The following examples are intended to illustrate but not limit the invention.

EXAMPLES

example 1

The following compositions were prepared by conventional mixing techniques: ingredients according to together [% by weight] comp. A [% by weight] comp. B [wt%] comp. C [wt%] glyoxylic acid 3.7 4.0 - 3.7 Polysilicone-29 0.3 - 4.0 - PEG-40/PPG-8 Methylaminopropyl/ Hydroxypropyl Dimethicone Copolymer - - - 0.3 NaOH/HCl To pH 2.0 water Ad 100.0

Switches of Indian frizzy hair (25 cm long, 2 g per bundle) were obtained from International Hair Importers & Products Inc., Glendale, NY, USA. One tress of hair was left untreated and saved for reference. The strands of hair were washed with a commercially available shampoo under the trade name Goldwell Kerasilk Control Purifying Shampoo and then air-dried for 15 hours. The volume of the hair tress was measured with a machine that rotated the hair tress, took a picture and analyzed the area of the resulting hair cone (V ₀ ). 2 g of the above compositions were applied to a strand of hair and left on the strands for 20 minutes at room temperature. The strands of hair were then blow-dried and treated with a straightening iron with a surface temperature of 200° C. (3 strokes per strand). The strands of hair were then shampooed again with the commercially available shampoo from above and allowed to air dry for 15 hours. The volume of the hair tresses was measured as described above (V ₁ ).

Each experiment with the above compositions was performed in triplicate.

The volume reduction was calculated using the following formula: $$V_{\mathrm{right}e\mathrm{i.e}}=\frac{V_1}{V_0}\cdot 100\%$$

The following results were achieved: treatment V _red [%] SD according to together 36.7 2.3 comp. A 41.2 1.2 comp. B 45.1 2.9 comp. C 43.2 1.6

As the above results clearly show, the composition of the present invention provided a higher smoothing effect compared to the comparative compositions.

The keratin fibers treated with the composition of the invention had the best cosmetic feel compared to the comparative compositions.

In addition, 4 trained experts in the field of hair care independently confirmed that there was no discernible color difference between the reference tress and the hair tress treated with the composition of the invention, whereas the hair tresses treated with the comparative compositions appeared lighter brownish than the reference hair tress.

example 2

The following compositions were prepared by conventional mixing techniques: ingredients according to together comp. A comp. B [% by weight] [% by weight] [% by weight] steps 1 2 1 2 1 2 glyoxylic acid 3.7 - 4.0 - - - Polysilicone-29 - 0.3 - - 4.0 - PEG-40/PPG-8 Methylaminopropyl/ Hydroxypropyl Dimethicone Copolymer - - - - - - NaOH/HCl To pH 2.0 water Ad 100.0

Switches of Indian frizzy hair (25 cm long, 2 g per bundle) were obtained from International Hair Importers & Products Inc., Glendale, NY, USA. One tress of hair was left untreated and saved for reference. The strands of hair were washed with a commercially available shampoo under the trade name Goldwell Kerasilk Control Purifying Shampoo and then air-dried for 15 hours. The volume of the hair tresses was measured as disclosed in Example 1 (V ₀ ). 2g of the compositions from step 1 above were applied to a tress of hair and left on the tresses for 20 minutes at room temperature. The hair tresses were then rinsed thoroughly with lukewarm water, towel dried and 2g of the composition from Step 2 was applied. The strands of hair were blow-dried and treated with a straightening iron with a surface temperature of 200° C. (3 strokes per strand). The strands of hair were then shampooed again with the commercially available shampoo from above and allowed to air dry for 15 hours. The volume of the hair tresses was measured as described above (V ₁ ).

Each experiment with the above compositions was performed in triplicate.

The volume reduction was calculated using the following formula: $$V_{\mathrm{right}e\mathrm{i.e}}=\frac{V_1}{V_0}\cdot 100\%$$

The following results were achieved: treatment V _red [%] SD according to together 46.8 1.8 comp. A 59.6 1.8 comp. B 60.2 7.8

As the above results clearly show, the composition of the present invention provided a higher smoothing effect compared to the comparative compositions. In addition, the smoothing performance of the inventive composition was similar to the one-step treatment of Example 1.

The keratin fibers treated with the composition of the invention had the best cosmetic feel compared to the comparative compositions.

In addition, 4 trained experts in the field of hair care independently confirmed that there was no discernible color difference between the reference tress and the hair tress treated with the composition of the invention, whereas the hair tresses treated with the comparative compositions appeared lighter brownish than the reference hair tress.

The following examples are within the scope of the present invention.

Example 3

% by weight

glyoxylic acid 1.0 Polysilicone-29 0.1 Ceteareth-3 0.1 cetrimonium chloride 1.0 dehydroxanthan gum 0.5 NaOH/HCl ad pH 2.5 water to 100.0

The concentration of glyoxylic acid in this example can be adjusted to 3 wt%, 5 wt%, 10 wt%, 15 wt%, 20 wt% and all values within this range.

The pH can likewise be adjusted in the range from 1.0 to 4.0.

example 4

% by weight

glyoxylic acid 0.1 Polysilicone-29 1.0 Ceteareth-3 0.1 cetrimonium chloride 1.0 dehydroxanthan gum 0.5 NaOH/HCl to pH 2.5 water to 100.0

The concentration of polysilicon 29 in this example can be adjusted to 3 wt%, 5 wt%, 10 wt% and all values within this range.

Example 5

% by weight

glyoxylic acid 3.0 Polysilicone-29 0.1 cetearyl alcohol 5.0 isopropyl palmitate 1.0 PEG-40 Hydrogenated Castor Oil 1.0 cetrimonium chloride 1.0 behenamidopropyldimethylamine 0.5 Polyquaternium-10 0.2 Perfume 0.2 preservatives 0.1 NaOH/HCl to pH 3.0 water to 100.0

The concentration of glyoxylic acid in this example can be adjusted to 3 wt%, 5 wt%, 10 wt%, 15 wt%, 20 wt% and all values within this range.

Example 6

Step 1

% by weight

glyoxylic acid 3.0 cetearyl alcohol 5.0 isopropyl palmitate 1.0 PEG-40 Hydrogenated Castor Oil 1.0 cetrimonium chloride 1.0 behenamidopropyldimethylamine 0.5 Perfume 0.2 preservatives 0.1 NaOH/HCl to pH 3.0 water to 100.0

The concentration of glyoxylic acid in this example can be adjusted to 3 wt%, 5 wt%, 10 wt%, 15 wt%, 20 wt% and all values within this range.

step 2

% by weight

Polysilicone-29 0.5 cetearyl alcohol 5.0 cetrimonium chloride 2.0 behenamidopropyldimethylamine 0.5 Perfume 0.2 preservatives 0.1 NaOH/HCl to pH 3.0 water to 100.0

The concentration of polysilicon-29 in this example can be adjusted to 0.1 wt%, 3 wt%, 5 wt%, 10 wt% and all values within this range.

Application of the compositions follows the procedure of Example 2.

Example 7

Step 1

% by weight

glyoxylic acid 3.0 PEG-40 Hydrogenated Castor Oil 0.2 xanthan gum 0.5 NaOH/HCl to pH 3.0 water to 100.0

The concentration of glyoxylic acid in this example can be adjusted to 3 wt%, 5 wt%, 10 wt%, 15 wt%, 20 wt% and all values within this range.

step 2

% by weight

Polysilicone-29 0.5 cetearyl alcohol 5.0 cetrimonium chloride 2.0 behenamidopropyldimethylamine 0.5 Perfume 0.2 preservatives 0.1 NaOH/HCl to pH 3.0 water to 100.0

The concentration of polysilicon 29 in this example can be adjusted to 0.1 wt%, 3 wt%, 5 wt%, 10 wt% and all values within this range.

Application of the compositions follows the procedure of Example 2.

example 8

Composition A

The composition of Step 1 of Example 7.

Composition B

% by weight

Polysilicone-29 0.5 dehydroxanthan gum 0.25 NaOH/HCl to pH 8.0 water to 100.0

The concentration of polysilicon-29 in this example can be adjusted to 0.1 wt%, 3 wt%, 5 wt%, 10 wt% and all values within this range.

The pH of composition B can be adjusted to 2.0, 5.0 or 10.0.

Compositions A and B are mixed in a 1:1 weight ratio before application and then applied to keratin fibers.

QUOTES INCLUDED IN DESCRIPTION

This list of documents cited by the applicant was generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Patent Literature Cited

• WO 2011104282 [0003]
• WO 2012010351 [0003]
• WO 2014067702 [0003]
• FR 2997845 [0004]
• FR 3044903 [0004]
• FR 2997847 [0004]
• WO 9627366
• US1985424 [0050]
• US2016962 [0050]
• US2703798 [0050]
• WO 9206984 [0050]
• EP 70074 A [0053]
• JP 2015123019 A [0053]
• DE 2521960 [0080]
• DE 28110103044738 [0080]
• DE 3217059 [0080]
• EP 337354A [0080]
• EP 524612 A [0082]
• EP640643A [0082]

Claims (12)

Composition for straightening keratin fibres, preferably human keratin fibres, more preferably human hair, having a pH of 4 or less and comprising - glyoxylic acid and/or its hydrate(s) and/or its salt(s), - Polysilicone-29. composition after claim 1 , characterized in that the total concentration of glyoxylic acid and/or its hydrate(s) and/or its salt(s) is in the range from 0.1 to 20% by weight, preferably in the range from 0.2 to 10% by weight, more preferably in the range from 0.25 to 5% by weight, further preferably in the range from 0.35 to 5% by weight, calculated on the total composition. composition after claim 1 and/or 2, characterized in that the total concentration of Polysilicone-29 is in the range from 0.01 to 10% by weight, preferably in the range from 0.02 to 8% by weight, more preferably in the range from 0.05 to 6% by weight. -% is more preferably in the range of 0.1 to 2% by weight calculated on the total composition. Composition according to any one of the preceding claims, characterized in that the weight ratio of glyoxylic acid and/or its hydrate(s) and/or its salt(s) to Polysilicone-29 is between 10 and 0.1. Composition according to any one of the preceding claims, characterized in that the composition is a thickened gel and contains a thickening agent, preferably a thickening polymer, more preferably an associative and/or non-associative thickening polymer, more preferably a carbohydrate-based non-associative thickening polymer , even more preferably it is selected from xanthan gum and/or dehydroxanthan gum. Composition according to any one of the preceding claims, characterized in that the composition is an emulsion and contains one or more hydrophobic compound(s), preferably selected from C ₁₂ - to C ₂₂ -fatty alcohols, fatty acid esters with an esterified C ₁₂ - to C ₂₂ - fatty acid and a linear or branched, saturated or unsaturated C ₃ to C ₁₈ fatty alcohol, natural and/or vegetable oils, hydrocarbon-based compounds and/or mixtures thereof. Composition according to any one of the preceding claims, characterized in that it also contains a surfactant, preferably an anionic and/or nonionic and/or cationic and/or amphoteric/zwitterionic surfactant. Composition according to one of the preceding claims , characterized in that the total concentration of surfactants is in the range from 0.05 to 25% by weight, preferably in the range from 0.1 to 15% by weight, particularly preferably in the range from 0.2% by weight to 8% by weight calculated on the total composition. Composition according to any one of the preceding claims, characterized in that it comprises one or more cationic conditioning polymers other than Polysilicone-29. Composition according to any one of the preceding claims, characterized in that the total concentration of cationic polymers is in the range from 0.01 to 5% by weight, preferably in the range from 0.02 to 4% by weight, more preferably in the range from 0.05 to 3% by weight % and most preferably in the range 0.1 to 2.5% by weight calculated on the total composition. Two-part composition comprising parts A and B intended to be stored separately and mixed immediately prior to application to the keratin fibers, part A being glyoxylic acid and/or its hydrate(s) and/or its salt(s) e) having a pH of less than 4 and Part B comprises polysilicon-29 having a pH in the range of 2-10. A multi-part kit comprising the compositions defined in claims 1 until 10 and/or the compositions defined in claim 11 and a keratin fiber straightening device, preferably a hair straightener.