Patent Publication Number: US-2022218578-A1

Title: Composition, process and kit for semi-permanent straightening and curling of keratin fibers

Description:
FIELD OF THE INVENTION 
     The present invention is directed to a composition, process, and kit for semi-permanent straightening and curling of keratin fibers. 
     BACKGROUND OF THE INVENTION 
     Changing ones hair shape has always been en vogue. Already in the ancient Egyptian era long, straight hair was popular. Women who were not blessed with this kind of natural hair already used fire heated iron plates to get their hair in the desired shape. This procedure often led to severe burns of the face and hands. It was not before the early 19th century that straightening irons became more professional with the invention of a hair tong made by Marcel Grateau. Nowadays, hot tools such as straightening irons as well as blow dryers are more popular than ever before. They came into the fashion for consumers in both salon and mass market. These tools lead to satisfying straightening results as they work at high temperatures (up to 230° C. for a straightening iron). When dry hair is getting in contact with the hot iron and a proper pressure is applied at the same time, the hair shape can be fixed for a certain amount of time until humidity is return hair to its original state. Unfortunately, application of such hot temperature leads to hair damage and thus a bad hair feel after their usage. 
     Up to now customers who had decided for a hair straightening, were bound by their decision because current techniques did not allow them to return their hair into a curly state. 
     Glyoxylic acid is a known ingredient for hair cosmetics which allow for long-lasting curl relaxation and volume reduction especially in combination with straightening irons at high temperatures (WO2011/104282, WO2012/010351). However, once the customer has decided for such a treatment, it is almost impossible to return to the original curly hair state. 
     WO2015/036051 and WO201036052 illustrate the use of glyoxylic acid in straightening processes in combination with blow-dry heat and ironing heat as well as post-straightening compositions. 
     WO2013/081018 discloses alkyl glyceryl ether in combination with lactic acid as a hair treatment agent. However, the present invention requires glyoxylic acid. 
     SUMMARY OF THE INVENTION 
     Therefore, the first object of the present invention is an aqueous cosmetic composition having a pH of less than 4 comprising: 
     a) glyoxylic acid and/or its salt(s) and/or its hydrate(s), 
     b) one or more alkyl glyceryl ether and/or alkyl polyglyceryl ether, and/or their mixtures, 
     c) one or more lipophilic compound(s), 
     d) one or more surfactant(s) different from group b), 
     wherein the composition is an emulsion. 
     The second object of the present invention is a process for reshaping keratin fibers, preferably human keratin fibers, more preferably human hair, comprising the steps of: 
     i) applying the composition as defined in the claims  1  to  10  onto keratin fibers and leaving it for a time period of 1 to 60 min, 
     ii) optionally rinsing-off the keratin fibers and optionally drying the keratin fibers, 
     iii) treating the keratin fibers with a hot tool in a temperature range from 45° C. to 230° C., 
     iv) optionally rinsing-off the keratin fibers, 
     v) optionally curling the keratin fibers with a curling tool in a temperature range from 45° C. to 230° C., 
     vi) optionally rinsing-off the keratin fibers. 
     The third object of the present invention is a process for reshaping keratin fibers, preferably human keratin fibers, more preferably human hair comprising the steps of: 
     vii) applying an aqueous composition having a pH of less than 4 and comprising one or more compound(s) according to a) as defined in claims  1  to  3 , 
     viii) leaving the composition onto keratin fibers for a time period of 1 to 60 min, 
     ix) optionally rinsing-off and optionally drying the keratin fibers, 
     x) treating the keratin fibers with a hot tool in a temperature range of 45° C. to 230° C., 
     xi) applying a composition comprising compounds b) to d) as defined above onto keratin fibers, 
     xii) leaving the composition for a time period of 1 to 60 min, 
     xiii) optionally treating the keratin fibers with a hot tool in a temperature range of 45° C. to 230° C., 
     The fourth object of the present invention is a kit-of-parts comprising a composition as defined above and a hot tool. 
     A fifth object of the present invention is a kit-of-parts comprising a first composition as defined above in step vii) and a second composition as defined above in step xi). 
    
    
     
       DESCRIPTION OF FIGURES 
         FIG. 1  is a photograph of the hair streaks treated with the compositions of example 1. The photograph was taken after the curling step. As clearly observable, the hair streak treated with comparative composition 1 exhibited the weakest curl resulting from the limited restyling ability of hair treated with comparative composition 1. 
         FIG. 2  is a photograph of the hair streaks treated with the compositions of example 1. The photograph was taken after the blow dry and brushing step. It illustrates the straightening degree after curling without employing a flat-ironing step. As clearly observable, the hair treated with comparative composition 2 exhibited greater waviness resulting from the limited straightness of hair treated with comparative composition 2. 
         FIG. 3  is a photograph of the hair streaks treated with the compositions of example 2. The photograph was taken after the brushing and blow-drying step. As clearly observable, the hair streaks treated with comparative compositions 3 and 4 exhibited more curling, especially at the tip of the streaks, whereas the inventive composition 2 delivered the straightest hair streak. 
         FIG. 4  is a photograph of the hair streaks treated with the compositions of example 2. The photograph was taken after the curl-ironing step. As clearly observable, the hair streaks treated with inventive composition 2 and comparative composition 4 exhibited stronger curling, whereas the comparative composition 3 delivered the weakest curl. 
         FIG. 5  is a photograph of the hair streaks treated with the compositions of example 3. The photograph was taken after the brushing and blow-drying step. As clearly observable, the hair streak treated with comparative composition 5 was less defined and had a fuzzy end, whereas the inventive compositions delivered the most defined hair streaks. 
         FIG. 6  is a photograph of the hair streaks treated with the compositions of example 3. The photograph was taken after the curl-ironing step. As clearly observable, the hair streaks treated with inventive compositions had much stronger curling compared to the comparative composition 5. The latter had the weakest curl of the set. 
     
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     The present invention addresses the above-mentioned problem of the prior art and allows for a transformation from curly to straight, and if desired, back to original curly keratin fibers. Additionally, straightness of keratin fibers is improved for the transformation from curly to straight with or without prior curling step. 
     The present invention is directed to an aqueous cosmetic composition having a pH of less than 4 comprising: 
     a) glyoxylic acid and/or its salt(s) and/or its hydrate(s), 
     b) one or more alkyl glyceryl ether and/or alkyl polyglyceryl ether, and/or their mixtures, 
     c) one or more lipophilic compound(s), 
     d) one or more surfactant(s) different from group b), 
     wherein the composition is an emulsion. 
     Without being bound by any theory, applicant has found out that compounds according to b) allow hair to undergo a thermoplastic transition. It is believed that these compounds act as plasticizers to hair. Thus, the inventive composition allows the customers to move their hairstyle from curly to straight, and then back from straight to curly hair. 
     It is preferred from the viewpoint of cosmetic acceptance and safety that the pH of the composition is in the range of 0.5 to 3.5, preferably in the range of 1 to 3, more preferably in the range of 1.5 to 2.5. 
     It is further preferred from the viewpoint of cosmetic acceptance and customer usability that the composition of the present invention is an oil-in-water emulsion. 
     Compounds According to a) 
     The composition of the present invention comprises glyoxylic acid and/or its salt(s) and/or its hydrate(s) as compounds according to a). 
     Glyoxylic acid may be used for the purpose of the present invention in its free acid form and its hydrate thereof. The hydrate is formed by providing an aqueous solution of glyoxylic acid and without any further pH adjustment, glyoxylic acid is almost quantitatively present as its hydrate. Additionally, the hydrate may condense to dimers. 
     A salt of glyoxylic acid may also be used. A salt is inevitably formed by adjusting the pH of the composition with any known base. Suitable salts are alkali metal salts such as sodium or potassium, alkaline earth metal salts such as magnesium or calcium, or ammonium salts. 
     It is preferred from the viewpoint of straightening efficiency that the concentration of compound(s) according to a) is 0.1% by weight or more, more preferably 0.2% by weight or more, further more preferably 0.5% by weight or more, still further more preferably 1% by weight or more, calculated to the total weight of the composition. 
     It is preferred from the viewpoint of straightening efficiency and cosmetic safety that the concentration of compound(s) according to a) is 25% by weight or less, more preferably 20% by weight or less, further more preferably 15% by weight or less, still further more preferably 12% by weight or less, calculated to the total weight of the composition. 
     For attaining the above-mentioned effect, it is preferred that the concentration of compound(s) according to a) is in the range of 0.1% to 25% by weight, preferably in the range of 0.2% to 20% by weight, more preferably in the range of 0.5% to 15% by weight, further more preferably 1% to 12% by weight, calculated to the total weight of the composition. 
     Compounds According to b) 
     The composition of the present invention comprises one or more alkyl glyceryl ether and/or alkyl polyglyceryl ether, and/or their mixtures, as compounds according to b). 
     It is preferred from the viewpoint of oil solubility and emulsification that the compounds according to b) have an HLB value in the range of 2 to 7. This allows for a preparation of a co-emulsion with the compounds according to c) and d). 
     However, in case the compounds according to b) have other HLB values, they are dispersable in the aqueous phase of the composition according to the present invention. 
     It is preferred from the viewpoint of emulsification that the alkyl chain of compounds according to b) is a straight or branched, saturated or unsaturated alkyl chain having a total carbon number of 8 or more. 
     It is further preferred from the viewpoint of conferring thermoplastic properties to keratin fibers that the alkyl chain of compounds according to b) is a straight or branched, saturated or unsaturated alkyl chain having a total carbon number of 9 or more. 
     It is preferred from the viewpoint of emulsification that the alkyl chain of compounds according to b) is a straight or branched, saturated or unsaturated alkyl chain having a total carbon number of 18 or less. 
     For attaining the above-mentioned effect, it is preferred that the alkyl chain of compounds according to b) is a straight or branched, saturated or unsaturated alkyl chain having a total carbon number in the range of 8 to 18, more preferably in the range of 9 to 18. 
     Suitable examples for compounds according to b) are isostearyl glyceryl ether, stearyl glyceryl ether, isodecyl glyceryl ether, 2-ethylhexyl glyceryl ether, and cetyl glyceryl ether as well as alkyl polyglyceryl ether as disclosed, for example, in EP2003110. 
     It is preferred from the viewpoint of commercial availability and conferring thermoplastic properties to keratin fibers that one or more compound(s) according to b) is isostearyl glyceryl ether. 
     It is further preferred from the viewpoint of hair transformation that the total concentration of one or more compound(s) according to b) is 0.1% by weight or more, more preferably 0.25% by weight or more, still more preferably 0.5% by weight or more, calculated to the total weight of the composition. 
     It is further preferred from the viewpoint of hair transformation that the total concentration of one or more compound(s) according to b) is 10% by weight or less, more preferably 8% by weight or less, still more preferably 5% by weight or less, calculated to the total weight of the composition. 
     For attaining the above-mentioned effects, the total concentration of one or more compound(s) according to b) is in the range of 0.1% to 10% by weight, preferably 0.25% to 8% by weight, more preferably 0.5% to 5% by weight, calculated to the total weight of the composition. 
     Compounds According to c) 
     The composition of the present invention comprises one or more lipophilic compound(s). 
     Lipophilic compounds according to c) are immiscible with water at 25° C. under atmospheric pressure. However, these compounds are emulsifiable with the help of compounds according to d) to form an emulsion. 
     Suitable compounds according to c) are from fatty alcohols having a linear or branched, saturated or unsaturated alkyl chain with a total carbon number in the range of C8 to C22 which may be optionally substituted with OH, fatty acid esters having esterified an linear or branched alcohol having an alkyl chain length of C3 to C22 with a linear or branched fatty acid having an alkyl chain length of C12 to C22, petrolatum-based compound(s), organopolysiloxane(s), vegetable oils, and/or their mixtures. 
     Suitable fatty alcohols having a linear or branched, saturated or unsaturated alkyl chain with a total carbon number in the range of C8 to C22 which may be optionally substituted with OH, are, for example, octyl alcohol, decyl alcohol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, pentadecyl alcohol, cetyl alcohol, palmitoleyl alcohol, heptadecyl alcohol, stearyl alcohol, oleyl alcohol, nonadecyl alcohol, arachidyl alcohol, behenyl alcohol, and/or their mixtures. 
     Suitable fatty acid esters having esterified an linear or branched alcohol having an alkyl chain length of C3 to C22 with a linear or branched fatty acid having an alkyl chain length of C12 to C22, are, for example, octyl palmitate, isocetyl palmitate, isopropyl palmitate, octyl stearate, oleyl oleate, and myristyl myristate, as well as their mixtures. 
     Suitable petrolatum-based compound(s) are, for example, mineral oil, polydecenes, Vaseline, paraffinum perliquidum, and paraffinum subliquidum, and/or their mixtures. 
     Suitable organopolysiloxanes are in particular the ones which are not soluble in water, as, for example, such as dimethicones with various viscosities and molecular weights and dimethiconols, aminated silicones with primary, secondary, tertiary or quaternary ammonium groups such as amodimethicone, polysilicone 9, and quaternium 80, cyclic silicones such as cyclomethicones, arylated silicones such as phenyl trimethicone. 
     Suitable vegetable oils are olive oil, almond oil, avocado oil, wheatgerm oil, and castor oil. 
     It is preferred from the viewpoint of emulsion stability that the total concentration of compound(s) according to c) is 0.5% by weight or more, more preferably 1% by weight or more, further more preferably 2% by weight or more, calculated to the total weight of the composition. 
     It is preferred from the viewpoint of emulsion stability and emulsion type that the total concentration of compound(s) according to c) is 25% by weight or less, more preferably 20% by weight or less, further more preferably 15% by weight or less, calculated to the total weight of the composition. 
     The composition according to any of the preceding claims characterized in that the total concentration of compound(s) according to c) is in the range of 0.5% to 25% by weight, preferably 1% to 20% by weight, more preferably 2% to 15% by weight, calculated to the total weight of the composition. 
     Compounds According to d) 
     The composition of the present invention comprises one or more surfactant(s) as compound(s) according to d) which is different from group b). 
     Compounds according to d) ensure the stability of the emulsion. 
     It is preferred from the viewpoint of emulsion stability that one or more compound(s) according to d) is/are selected from non-ionic surfactant(s), cationic surfactant(s), anionic surfactant(s), amphoteric/zwitterionic surfactant(s), and/or their mixtures, preferably it is selected from non-ionic and/or cationic surfactant(s). 
     Suitable non-ionic surfactant preferably have an HLB value in the range of 7 to 14 from the viewpoint of stabilizing the emulsion. 
     Suitable non-ionic surfactants are, for examples, fatty alcohol ethoxylates, propylene glycol ethers of fatty alcohols, polyethylene glycol or polypropylene glycol esters of fatty acids, ethoxylated or propoxylated triglycerides, alkyl polyglycosides, and/or their mixtures. 
     Suitable cationic surfactants are, for example, quaternary ammonium salts having an alkyl chain length in the range of C12 to C22. Suitable examples are cetyl trimethyl ammonium chloride, stearyl trimonium chloride, dipalmitoyl dimonium chloride, distearyl dimethyl ammonium chloride, stearamidopropyl trimonuim chloride, dioleoylethyl dimethyl ammonium methosulfate, dioleoylethyl hydroxyethylmonium methosulfate, and/or their mixtures. 
     Suitable anionic surfactants are, for example, alkyl sulfate or ethoxylated alkyl ether sulfate surfactants with an alkyl chain length of C 10  to C 22 , and/or their mixtures. 
     Suitable surfactants are laureth sulfates, coceth sulfate, pareth sulfate, capryleth sulphate, myreth sulfate, oleth sulfate, deceth sulfate, trideceth sulfate, coco sulphate, C 10 -C 16  alkyl sulphate, C 11 -C 15  alkyl sulphate, C 12 -C 18  alkyl sulphate, C 12 -C 15  alkyl sulphate, C 12 -C 16  alkyl sulphate, C 12 -C 13  alkyl sulfate, lauryl sulphate, myristyl sulphate, palm kernel sulphate, cetearyl sulfate, cetyl sulphate, decyl sulphate, oleyl sulphate, behenyl sulphate and/or their salts, and/or their mixtures. All of the aforementioned anionic surfactants may or may not be ethoxylated at various degrees. 
     Cations for anionic surfactants may be selected from sodium, potassium, magnesium and/or ammonium. 
     Suitable amphoteric/zwitterionic surfactant(s) are, for example, various known betaines such as alkyl betaines, fatty acid amidoalkyl betaines and sulfobetaines such as lauryl hydroxysulfobetaine; long-chain alkyl amino acids, such as cocoaminoacetate, cocoaminopropionate, sodium cocoamphopropionate and—acetate are suitable, and/or their mixtures. 
     The most preferred surfactants are cationic surfactants, in particular cetyl trimethyl ammonium chloride, from the viewpoint of emulsion stability. 
     It is preferred from the viewpoint of emulsion stability that the total concentration of compound(s) according to d) is 0.2% by weight or more, more preferably 0.5% by weight or more, still more preferably 1% by weight or more, calculated to the total weight of the composition. 
     It is preferred from the viewpoint of emulsion stability that the total concentration of compound(s) according to d) is 10% by weight or less, more preferably 5% by weight or less, still more preferably 3% by weight or less, calculated to the total weight of the composition. 
     For attaining the above-mentioned effects, it is preferred that the total concentration of compound(s) according to d) is in the range of 0.2% to 10% by weight, more preferably 0.5% to 5% by weight, still more preferably 1% to 3% by weight, calculated to the total weight of the composition. 
     One-Step Treatment Method 
     The present invention is also directed to a process for reshaping keratin fibers, preferably human keratin fibers, more preferably human hair, comprising the steps of: 
     i) applying the composition as defined in the claims  1  to  10  onto keratin fibers and leaving it for a time period of 1 to 60 min, 
     ii) optionally rinsing-off the keratin fibers and optionally drying the keratin fibers, 
     iii) treating the keratin fibers with a hot tool in a temperature range from 45° C. to 230° C., 
     iv) optionally rinsing-off the keratin fibers, 
     v) optionally curling the keratin fibers with a curling tool in a temperature range from 45° C. to 230° C., 
     vi) optionally rinsing-off the keratin fibers. 
     Preferably, from the viewpoint of straightening, the time range of step i) is in the range of 5 to 45 min, more preferably in the range of 10 to 30 min. 
     For step iii), it is preferred from the viewpoint of straightening that the hot tool is a flat-iron for straightening having a surface temperature in the range of 90° C. to 230° C., more preferably 130° C. to 210° C. Alternatively, from the viewpoint of consumer applicability, a blow dryer and comb may be used having an air temperature in the range of 45° C. to 90° C. 
     For the curling step v) it is preferred to use a curling iron or a hot comb with a further preferred temperature range from 90° C. to 210° C., from the viewpoint of curling efficiency and hair damage. 
     Two-Step Treatment Method 
     The present invention also is directed to a process for reshaping keratin fibers, preferably human keratin fibers, more preferably human hair comprising the steps of: 
     vii) applying an aqueous composition having a pH of less than 4 and comprising one or more compound(s) according to a) as defined above, 
     viii) leaving the composition onto keratin fibers for a time period of 1 to 60 min, 
     ix) optionally rinsing-off and optionally drying the keratin fibers, 
     x) treating the keratin fibers with a hot tool in a temperature range of 45° C. to 230° C., 
     xi) applying a composition comprising compounds b) to d) as defined above onto keratin fibers, 
     xii) leaving the composition for a time period of 1 to 60 min, 
     xiii) optionally treating the keratin fibers with a hot tool in a temperature range of 45° C. to 230° C., 
     As further optional steps, the process of above may comprise: 
     xv) optionally curling the keratin fibers with a curling tool in a temperature range from 45° C. to 230° C., 
     xvi) optionally rinsing-off the keratin fibers. 
     The two-step process is an alternative for the one-step process and yield equally favourable results. 
     Preferably, from the viewpoint of straightening, the time range of steps vii) and/or xii) is in the range of 5 to 45 min, more preferably in the range of 10 to 30 min. 
     For steps x) and/or xiii), it is preferred from the viewpoint of straightening that a flat-iron is used for straightening having a surface temperature in the range of 90° C. to 230° C., more preferably 130° C. to 210° C. Alternatively, from the viewpoint of consumer applicability, a blow dryer and comb may be used having an air temperature in the range of 45° C. to 90° C. 
     For the curling step xv) it is preferred to use a curling iron or a hot comb with a further preferred temperature range from 90° C. to 210° C., from the viewpoint of curling efficiency and hair damage. 
     Kit-of-Parts 
     The present invention is further directed to a kit-of-parts comprising the inventive composition as defined above and a hot tool. Suitable hot tools are blow dryers, hot combs, curling irons, and/or straightening irons. 
     The invention is further directed to a kit-of-parts comprising a first composition as defined above for step vii) and a second composition as defined above in step xi). Optionally, the kit may further comprise a hot tool. Suitable hot tools are blow dryers, hot combs, curling irons, and/or straightening irons. 
     The following examples are to illustrate the present invention, but not to limit it. 
     EXAMPLES 
     Example 1 
     The following compositions were prepared by adding compound b), c), and d) into water and heating the mixture under stirring above 70° C. After cooling, compound a) or lactic acid as well as NaOH were added. 
     
       
         
           
               
               
               
               
               
             
               
                   
               
               
                   
                   
                 Inventive 
                 Comparative 
                 Comparative 
               
               
                   
                   
                 composition 
                 composition 
                 composition 
               
               
                 Compound 
                 Ingredients 
                 1 
                 1 
                 2 
               
               
                   
               
             
            
               
                 a) 
                 Glyoxylic acid 
                 0.8 
                 0.8 
                 — 
               
               
                 — 
                 Lactic acid 
                 — 
                 — 
                 0.8 
               
               
                 b) 
                 Isostearyl 
                 3.5 
                 — 
                 3.5 
               
               
                   
                 glyceryl ether 
               
               
                 c) 
                 Cetearyl 
                 3.0 
                 3.0 
                 3.0 
               
               
                   
                 alcohol 
               
               
                 d) 
                 Ceteareth-30 
                 1.5 
                 1.5 
                 1.5 
               
            
           
           
               
               
               
            
               
                   
                 NaOH ad pH 
                 Ad pH 2.2 
               
               
                   
                 Water 
                 Ad 100.0 
               
               
                   
                   
               
            
           
         
       
     
     Human hair streaks (Caucasian hair, 2 g per bundle, 21 cm long) were purchased from Fischbach+Miller Haar, Laupheim, Germany. The hair streaks were shampooed with a commercially available shampoo under the brand name Goldwell Dualsenses Deep Cleansing Shampoo. 1 g of each of the compositions from above were then applied on the hair streaks and the compositions were left for 3 min onto the hair streaks. Then the hair streaks were rinsed for 1 min with lukewarm water and blow dried. As a next step, the hair streaks were treated with 3 strokes of a flat iron at 160° C. iron surface temperature. At this point, straightness of the hair streaks was evaluated. 
     Then the hair streaks were treated with 1 pass of a curl iron at 180° C. iron surface temperature for 10 s per hair streak. At this point, curling of the hair streaks was evaluated (see  FIG. 1 ). 
     As a last step, the hair streaks were shampooed with the commercially available shampoo of above, combed, and blow dried. At this point, straightness of the hair streaks was evaluated again (see  FIG. 2 ). 
     The following results were obtained as displayed in the table below and illustrated in  FIGS. 1 and 2 : 
     
       
         
           
               
               
               
               
             
               
                   
               
               
                   
                 Inventive 
                 Comparative 
                 Comparative 
               
               
                   
                 composition 
                 composition 
                 composition 
               
               
                 Process step 
                 1 
                 1 
                 2 
               
               
                   
               
             
            
               
                 Straightening after 
                 Very straight 
                 Very straight 
                 Very straight 
               
               
                 flat-ironing 
               
               
                 Curling after 
                 Strong curl 
                 Weak curl 
                 Strong curl 
               
               
                 curl-ironing (FIG. 1) 
               
               
                 Straightening after 
                 Slightly wavy 
                 Slightly wavy 
                 Wavy 
               
               
                 shampoo and blow 
               
               
                 drying (FIG. 2) 
               
               
                   
               
            
           
         
       
     
     As a result from comparative testing above, the inventive composition delivered best restyling ability from straight to curly and back to straight hair. None of the two comparative compositions exhibited the same performance. 
     Example 2 
     The following compositions were prepared by adding compound b), c), and d) or their equivalents for comparative purposes into water and heating the mixture under stirring above 70° C. After cooling, compound a) or lactic acid as well as NaOH were added. 
     
       
         
           
               
               
               
               
               
             
               
                   
               
               
                   
                   
                 Inventive 
                 Comparative 
                 Comparative 
               
               
                   
                   
                 composition 
                 composition 
                 composition 
               
               
                 Compound 
                 Ingredients 
                 2 
                 3 
                 4 
               
               
                   
               
             
            
               
                 a) 
                 Glyoxylic acid 
                 0.8 
                 0.8 
                 — 
               
               
                   
                 Lactic acid 
                 — 
                 — 
                 0.8 
               
               
                 b) 
                 Isostearyl 
                 3.5 
                 — 
                 3.5 
               
               
                   
                 glyceryl ether 
               
               
                 c) 
                 Cetearyl 
                 3.0 
                 3.0 
                 3.0 
               
               
                   
                 alcohol 
               
               
                 d) 
                 Cetrimonium 
                 1.5 
                 1.5 
                 1.5 
               
               
                   
                 chloride 
               
            
           
           
               
               
               
            
               
                   
                 NaOH ad pH 
                 Ad pH 2.2 
               
               
                   
                 Water 
                 Ad 100.0 
               
               
                   
                   
               
            
           
         
       
     
     Human hair streaks (Caucasian hair, 2 g per bundle, 21 cm long) were purchased from Fischbach+Miller Haar, Laupheim, Germany. The hair streaks were shampooed with a commercially available shampoo under the brand name Goldwell Dualsenses Deep Cleansing Shampoo. 1 g of each of the compositions from above were then applied on the hair streaks and the compositions were left for 3 min onto the hair streaks. Then the hair streaks were rinsed for 1 min with lukewarm water and blow dried. The aforementioned application, rinsing, and blow-drying steps were repeated 2 more times, except for the last blow-drying step which was replaced by air-drying. As a next step, the hair streaks were brushed and blow-dried with hot air having a temperature of 60° C. At this point, straightness of the hair streaks was evaluated (see  FIG. 3 ). 
     Then the hair streaks were treated with 1 pass of a curl iron at 130° C. iron surface temperature for 10 s each. At this point, curling of the hair streaks was evaluated (see  FIG. 4 ). 
     The following results were obtained as displayed in the table below and illustrated in  FIGS. 3 and 4 : 
     
       
         
           
               
               
               
               
             
               
                   
               
               
                   
                 Inventive 
                 Comparative 
                 Comparative 
               
               
                   
                 composition 
                 composition 
                 composition 
               
               
                 Process step 
                 2 
                 3 
                 4 
               
               
                   
               
             
            
               
                 Straightening after 
                 Straight 
                 Little end curl 
                 Medium end curl 
               
               
                 brushing and blow- 
               
               
                 drying (FIG. 3) 
               
               
                 Curling after 
                 Strong curl 
                 Weak curl 
                 Strong curl 
               
               
                 curl-ironing (FIG. 4) 
               
               
                   
               
            
           
         
       
     
     As a result from comparative testing above, the inventive composition delivered best restyling ability from straight to curly hair. None of the two comparative compositions exhibited the same performance. 
     Example 3 
     The following compositions were prepared by adding compound b), c), and d) or their equivalents for comparative purposes into water and heating the mixture under stirring above 70° C. After cooling, compound a) or lactic acid as well as NaOH were added. 
     
       
         
           
               
               
               
               
               
               
               
             
               
                   
                   
               
               
                   
                   
                 Inventive 
                 Inventive 
                 Inventive 
                 Inventive 
                 Comparative 
               
               
                   
                 Ingredients 
                 comp. 1 
                 comp. 3 
                 comp. 4 
                 comp. 5 
                 comp. 5 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
               
               
               
            
               
                 a) 
                 Glyoxylic acid 
                 0.8 
                 0.8 
                 0.8 
                 0.8 
                 0.8 
               
               
                 — 
                 Lactic acid 
                 — 
                   
                   
                   
                 — 
               
               
                 b) 
                 Isostearyl glyceryl ether 
                 3.5 
                   
                 10.0  
                   
                 — 
               
               
                   
                 Cetyl glyceryl ether 
                 — 
                 3.5 
                 — 
                 — 
                 — 
               
               
                   
                 Hexyldecyl polyglyceryl 
                 — 
                 — 
                 — 
                 3.5 
                 — 
               
               
                   
                 ether 
               
               
                 — 
                 PEG-18 glyceryl 
                 — 
                 — 
                 — 
                 — 
                 3.5 
               
               
                   
                 oleate/cocoate 
               
               
                 c) 
                 Cetearyl alcohol 
                 3.0 
                 3.0 
                 3.0 
                 3.0 
                 3.0 
               
               
                 d) 
                 Ceteareth-30 
                 1.5 
                 1.5 
                 1.5 
                 1.5 
                 1.5 
               
            
           
           
               
               
               
            
               
                 — 
                 NaOH ad pH 
                 Ad pH 2.2 
               
               
                   
                 Water 
                 Ad 100.0 
               
               
                   
               
            
           
         
       
     
     For the compositions above, the same experimental protocol as explained for example 2 was used. 
     Straightness of the hair streaks was evaluated (see  FIG. 5 ). 
     Then the hair streaks were treated with 1 pass of a curl iron at 130° C. iron surface temperature for 10 s each. At this point, curling of the hair streaks was evaluated (see  FIG. 6 ). 
     The following results were obtained as displayed in the table below and illustrated in  FIGS. 5 and 6 : 
     
       
         
           
               
               
               
               
               
               
             
               
                   
               
               
                   
                 Inv. 
                 Inv. 
                 Inv. 
                 Inv. 
                 Comparative 
               
               
                 Process step 
                 comp. 1 
                 Comp. 3 
                 Comp. 4 
                 Comp. 5 
                 comp. 5 
               
               
                   
               
             
            
               
                 Straightening 
                 Very 
                 Straight, 
                 Very 
                 Very straight, 
                 Very straight, low 
               
               
                 after brushing 
                 straight, 
                 strong 
                 straight, 
                 medium 
                 bundling, small, 
               
               
                 and blow- 
                 medium 
                 bundling, 
                 strong 
                 bundling, 
                 fuzzy end-curl 
               
               
                 drying (FIG. 5) 
                 bundling, 
                 small end-curl 
                 bundling, 
                 small end-curl 
               
               
                   
                 no end-curl 
                   
                 no end-curl 
               
               
                 Curling after 
                 Strong curl, 
                 Medium curl, 
                 Strong curl, 
                 Medium curl, 
                 Low curl, 
               
               
                 curl-ironing 
                 defined end-curl 
                 slightly fuzzy 
                 defined end-curl 
                 slightly fuzzy 
                 slightly fuzzy 
               
               
                 (FIG. 6) 
                   
                 end-curl 
                   
                 end-curl 
                 end-curl 
               
               
                   
               
            
           
         
       
     
     As a result from comparative testing above, the inventive compositions delivered best restyling ability from straight to curly hair. The comparative composition particularly suffered from fuzzy straightness with low bundling, and lower curling performance. 
     The following examples are within the scope of the present invention. 
     Example 4 
       
     
       
         
           
               
               
             
               
                   
                   
               
               
                   
                 % by weight 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 Glyoxylic acid 
                 6.0 
               
               
                   
                 Isostearyl glyceryl ether 
                 2.0 
               
               
                   
                 Stearyl alcohol 
                 5.0 
               
               
                   
                 Behentrimonium chloride 
                 0.5 
               
               
                   
                 Behenamidopropyl dimethylamine 
                 0.5 
               
               
                   
                 Ceteareth-33 
                 0.1 
               
               
                   
                 Glycerine 
                 0.25 
               
               
                   
                 Amodimethicone 
                 0.5 
               
               
                   
                 Xanthan gum 
                 1.0 
               
               
                   
                 NaOH 
                 q.s. ad pH 3.5 
               
               
                   
                 Water 
                 ad 100.0 
               
               
                   
                   
               
            
           
         
       
     
     Example 5 
       
     
       
         
           
               
               
             
               
                   
                   
               
               
                   
                 % by weight 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 Glyoxylic acid 
                 2.0 
               
               
                   
                 Isodecyl glyceryl ether 
                 3.0 
               
               
                   
                 Cetearyl alcohol 
                 5.0 
               
               
                   
                 Isopropyl myristate 
                 2.0 
               
               
                   
                 PEG-40 hydrogenated castor oil 
                 3.0 
               
               
                   
                 Benzyl alcohol 
                 0.5 
               
               
                   
                 Dimethicone 
                 0.25 
               
               
                   
                 Polyquaternium 10 
                 0.5 
               
               
                   
                 Hydroxyethyl cellulose 
                 1.5 
               
               
                   
                 NaOH 
                 q.s. ad pH 2.5 
               
               
                   
                 Water 
                 ad 100.0 
               
               
                   
                   
               
            
           
         
       
     
     Example 6 
       
     
       
         
           
               
               
             
               
                   
                   
               
               
                   
                 % by weight 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 Glyoxylic acid 
                 10.0 
               
               
                   
                 Isostearyl glyceryl ether 
                 1.0 
               
               
                   
                 Cetearyl alcohol 
                 5.0 
               
               
                   
                 Behenamidopropyl dimethylamine 
                 0.75 
               
               
                   
                 Isopropyl Palmitate 
                 2.0 
               
               
                   
                 Dipropylene Glycol 
                 2.0 
               
               
                   
                 Panthenol 
                 0.5 
               
               
                   
                 Divinyldimethicone/Dimethicone Copolymer 
                 0.75 
               
               
                   
                 Dehydroxanthan Gum 
                 1.0 
               
               
                   
                 Phenoxyethanol 
                 0.5 
               
               
                   
                 NaOH 
                 q.s. ad pH 2.0 
               
               
                   
                 Water 
                 ad 100.0