AU2015202165B2

AU2015202165B2 - Process for semi-permanent straightening of curly, frizzy or wavy hair

Info

Publication number: AU2015202165B2
Application number: AU2015202165A
Authority: AU
Inventors: Alderano Mannozzi
Original assignee: Kao Corp
Current assignee: Kao Corp
Priority date: 2010-02-24
Filing date: 2015-04-28
Publication date: 2017-03-02
Anticipated expiration: 2031-02-23
Also published as: AU2015202165A1

Abstract

The process of the invention provides for a preventive hair treatment with buffering agent, in particular glyoxylic acid in combination with mechanical straightening with hair straightening iron at temperature of approximately 2000C +/- 500C.

Description

1 2015202165 28 Apr 2015

Description

Process for semi-permanent straightening of curly, frizzy or wavy hair.

The present application is a divisional application from Australian patent application number 2011219795, which claims priority from Italian basic application number 5 MC2010A000028, filed 24 February 2010, which is hereby incorporated by reference in its entirety.

The present patent application for industrial invention relates to a process used to semi-permanently straighten curly, frizzy or wavy hair. 10 1. Glyoxylic acid: it is an alpha-keto acid that can be found in crystalline monohydrate form (CAS No.: 563-96-2) or in aqueous solution (CAS No.: 298-12-4).

Main synonyms: Formylformic acid; alpha-Ketoacetic acid; Glyoxalic acid; Oxalaldehydic acid; Oxoacetic acid; Oxoethanoic acid and others. 15 Its use in the cosmetic sector is considered safe and permitted without any restrictions with indication of the buffering agent function of the pH. 2. Alpha-keto acids: Alpha-keto acids are acids with a carbonylic group in alpha position with respect to the carbon atom of the carboxylic group. 3. Semi-perm: treatment of curly or frizzy hair to straighten it with permanence in 20 such a condition for a number of washings higher than 5. 4. Hair straightening iron: Electrical heating device used in association with a combination of heat and pressure to straighten hair. It is generally composed of two flat heating elements, covered with various materials, between which a lock of hair is pressed at a time. Flair straightening irons are commonly found on the 25 market. 5. Hairdryer: ordinary hair-drying device with heating resistance and fan. 6. Buffering agents: substances dissolved in water to prevent pH changing in the solution for moderate additions of acids or bases (buffering).

Human hair is divided in two types: 30 - a first type of hair, the so-called "Afro" hair (hair with diameter of 70-100 microns), of generally dark color, characterized in that it is more or less curly according to the amount of disulphide groups between the amino acidic chains of keratin (human hair's base protein); C:\pof\vvord\SPEC-1027497.docx -2- 2015202165 23 Nov 2016 - a second type of hair, the so-called "Caucasian" hair (hair with lower diameter than "Afro" hair), either of dark or light color, characterized in that it is less curly than the "Afro" hair, due to the lower amount of disulphite bridges in its keratin structure. 5 Three types of techniques are currently used to straighten curly or frizzy hair: a. Treatment with electrical plates basically composed of two hot plates (with temperature higher than 100°C), between which hair is placed and pressed to obtain desired styling. The result disappears after the first washing with water and shampoo. io b. Low-temperature chemical and mechanical treatment: chemical substances are applied to hair, which is treated at temperatures lower than 100°C, to induce transitory modifications in the aspect of the capillary fiber that disappear after washing hair with water and shampoo, c. High-temperature chemical and mechanical treatment: chemical is substances are applied to hair, which is treated at temperatures higher than 100°C (same technique as a) above), to induce transitory modifications in the aspect of the capillary fiber that disappear after washing hair with water and shampoo.

Currently, an aspect is that, although chemical substances able to straighten 20 human curly, frizzy or wavy hair are on the market, said substances are impaired by high-toxicity for man and high aggressiveness for hair (i.e.: formaldehyde, sodium hydroxide, sulphur compounds, etc.).

Moreover, it must be said that these processes with chemical substances do not guarantee that treated hair will remain straighten for long after straightening. 25 An aspect of the present invention is to devise a new chemical mechanical process (similar to the one illustrated under c) above) to straighten hair semipermanently (once treated hair will remain straight after a number of washings higher than 5). The innovation consists in the identification of a group of chemical substances that, when combined with a high-temperature mechanical treatment, 30 unlike the state of the art, allow for obtaining straight, soft, shiny and volumeless hair from curly and frizzy hair, said characteristics being maintained also after repeated washings with water and shampoo. A further aspect of the invention is to devise a process with the aforesaid features, which uses buffering agents in very low percentage, and in any case lower -3- 2015202165 23 Nov 2016 than the values used in the described process, thus reducing the stress for treated hair.

These aspects are addressed according to the invention, with the characteristics that are listed in the attached independent claim 1. 5 Advantageous realizations appear from the dependent claims.

The process of the invention provides for the combined action of mechanical pressing with hot plates at a temperature of approximately 200°C (+/- 50°C) with preventive hair treatment with a solution containing a buffering agent.

More precisely, the process provides for: 10 a) Application on hair of a solution containing a buffering acid agent from the alpha-ketoacids family; b) Permanence of said substance in contact with hair for 15 to 120 minutes; c) Hair drying, is d) Straightening of hair with hair straightening iron at temperature of approximately 200 +/- 50 C°;

The process further provides a process for semi permanent hair straightening, comprising the following application steps: a) Application on hair of a solution containing glyoxylic acid dissolved 20 at a ratio between 5% and 25% in weight; b) Permanence of substance in contact with hair for 15 to 120 minutes; c) Hair drying; and d) Hair straightening with hair straightening iron at temperature of approximately 200+/-50 C°. 25 A further aspect of the invention is the use of glyoxylic acid for semi-permanent hair straightening, wherein the glyoxylic acid is used in combination with mechanical hair straightening means.

In particular, the process of the invention has proved to induce semi-permanent modifications in the hair structure, which will remain such after repeatedly washing 30 hair in normal conditions of use.

Studies carried out on the chemical substances that are already used in the cosmetic sector and tests carried out on hair have resulted in the selection of some substances, which are already known for their pH buffering properties, which, when 2015202165 23 Nov 2016 -4- used in combination with mechanical straightening, allow for semi-permanently eliminating the typical curves that characterize curly, frizzy or wavy hair.

In particular, the reduction or elimination of “curves” in hair is expressed as easier-to-comb hair and lower global volume of the capillary fiber due to the 5 elimination of said curves (and, consequently, a reduction of the volume occupied by hair in the space).

Table 1 contains a list of all buffering agents that are included in the European Inventory of ingredients used in cosmetic products, attached to Decision no. 1996/335/CE dated 08/05/1996, and following amendments and integrations. 10 The process according to the invention advantageously uses glyoxylic acid in aqueous solution, which has demonstrated to give appreciable results compared to the other buffering agents contained in the aforementioned list.

Moreover, also the substances listed in Table 2 have been tested, mixed with one of the buffering agents, which are contained in the list attached to the Decision is no. 1996/335/CE dated 08/05/1996 and following amendments and integrations.

Further characteristics of the invention will become apparent from the detailed description below.

Amongst the substances contained in the European list of ingredients used in cosmetic products and having a buffering function that have been experimented 20 within the process of the invention, glyoxylic acid has given the best results.

Tests consisted in dissolving 10 grams of glyoxylic acid in 100 milliliters of water.

More precisely, with ponderal ratio comprised between 5 and 25%.

In particular, hair was washed with basic pH (7.5-8.5) shampoo, then said 25 glyoxylic acid solution was applied (application can be made with hard bristle brush, spray or in any other way).

However, it must be noted that said pre-washing with said basic pH shampoo did not prove to be fundamental for semi-permanent hair straightening.

Hair was left in contact with the substance for 60 minute time (+/- 30 minutes) 30 and then dried with the hairdryer. WO 2011/104282 PCT/EP2011/052693 -5- 2015202165 28 Apr 2015

Once dried, hair was straightened with hair straightening iron heated at average temperature of approximately 200 C°, +/- 50 C°. It must be noted that the materials of the iron plates do not affect the process of the invention.

Finally, hair was rinsed again with water or washed again with 5 shampoo and dried.

At the end of treatment, hair was shiny, straight, volumeless, soft to touch, and especially pleasant.

The tests demonstrated the efficacy of the invention both on natural and chemically dyed or bleached hair. to It was experimentally proved that the efficacy of treatment is maintained over time for at least six washings, rinsings and dryings in normal use conditions of hair shampoo (as confirmed by the values contained in the tables attached to the end of this description: Tables 1-A to 1-D).

Further tests were carried out by adding one of the substances listed in is table 2 to the glyoxylic acid solution.

Each substance was tested in a mixture with such glyoxylic acid solution by adding 10 grams of one of the substances listed in table 2 to 100 milliliters of said solution.

Following is a typical composition of said mixture: 20 Example 1:

Water...................................... 100 milliliters

Glyoxylic acid........................... 10 grams

Potassium iodide....................... 10 grams

Example 2: 25 Water...................................... 100 milliliters

Glyoxylic acid........................... 10 grams

Dihydroxyacetone ..................... 10 grams

Example 3:

Water..................................... 100 milliliters 30 Glyoxylic acid.......................... 10 grams

Ozonized jojoba oil.................... 10 grams

Inert emulsifying agent (glycerol) .. 10 grams 2015202165 28 Apr 2015 WO 2011/104282 PCT/EP2011/052693 -6-

Example 4:

Water......................................... 100 milliliters

Glyoxylic acid.............................. 10 grams 2,4 hexadienal............................. 10 grams 5 In example 3 an emulsifying agent (glycerol), which is inert for hair straightening, was added to the solution to facilitate ozonized jojoba oil dispersion in aqueous solution.

The mixture obtained in example 3 is an oily mixture due to the use of jojoba oil. ίο Also at the end of treatments carried out with the mixtures illustrated in examples 1,2,3 and 4, hair was shiny, straight, volumeless, soft to touch and especially pleasant; moreover, hair straightening was tested in terms of time permanence.

Further tests were carried out to see whether the effect obtained with 15 aqueous solutions could be repeated also when said substances were part of a commercial cosmetic formulation (i.e. mixed with other substances that are normally used in the cosmetic sector).

An additional test was carried out by adding glyoxylic acid (and its mixtures with potassium iodide, dihydroxyacetone, ozonized jojoba oil and 2,4 20 hexadienal illustrated in examples 1,2,3 and 4) with hair treatment cosmetics found on the market.

In particular, a hair straightening test was carried out using the formulation of a cosmetic product by INOAR Cosmeticos Ltda of San Paulo, Brazil, known as “Tratamento capillar marroquino”. The product was deprived 25 of its active ingredient for hair straightening. 10 grams of glyoxylic acid were added to 100 milliliters of said cosmetic and, after carrying out the same hair treatment operations illustrated in the foregoing pages, the results were identical to the ones achieved using the same percentage ratio of glyoxylic acid in water. 30 At the end of treatment, hair was permanently shiny, straight, volumeless, and soft to touch, and with an especially pleasant look. 2015202165 28 Apr 2015 WO 2011/104282 PCT/EP2011/052693 -7-

Similar results were obtained from four tests made with four mixtures identical to the ones of examples 1, 2, 3, and 4, using 100 milliliters of cosmetic product instead of 100 milliliters of acidulated water.

Hair was straight, volumeless, soft to touch and especially shiny when 5 exposed to sunlight or artificial light.

Experimentally, it was finally ascertained that the best range is comprised between 5% and 25% of the substances listed in table 2, so that the weight percentage of each of them is included between 5% and 25%, with completion to 100 made of inert substances with respect to straightening of ίο curly, frizzy or wavy hair.

It must be noted that tests have demonstrated that the hair straightening effect, with consequent volume reduction, is not appreciated when heating hair at temperatures of approximately 50-60°C with an ordinary hairdryer, whereas it is clearly visible until the first rinsing and/or shampooing is in case of treatment for a few seconds at temperatures of approximately 200+/-50 C°

Said tests have also demonstrated that the higher the contact time of the invention and its mixtures with the capillary fiber, the higher the hair straightening effect will be. 20 25 30 35 WO 2011/104282 PCT/EP2011/052693 -8- 2015202165 28 Apr 2015

Table 1-A GLYOXYLIC ACID "AFRO" NATURAL CURLY HAIR IRON at 200°C STRAIGHTENING EFFECT ASSESSMENT (curve reduction) TESTED MIX pH of initial mix pH after contact with hair washed with basic shampoo after no. 1 washing and drying after no. 2 washings and dryings after no. 3 washings and dryings after no. 4 washings and dryings after no. 5 washings and dryings after no. 6 washings and dryings WATER 100 ml 5,5 6,0 (-) (-) (-) (-) (-) (-) WATER 95 ml + GLYOXYLIC ACID 5 q 2,1 2,1 (+++) (++) (+) (+) (+) (+/-) WATER 90 ml + GLYOXYLIC ACID 10 a 2,0 2,0 (++++) (+++) (++) (++) (++) <+) WATER 85 ml + GLYOXYLIC ACID 15 q 1,8 1,8 (+++) (+++) (++) (++) (++) (+) WATER 80 ml + GLYOXYLIC ACID 20 q 1,6 1,6 (++) (++) (+) (+) (+) (+/-) WATER 80 ml + GLYOXYLIC ACID 25 q 1,5 1,5 (++) (++) (+) (+) (+) (+/-) WATER 100 ml + GLYOXYLIC ACID 10 g + Potassium Iodide 10 q 2,0 2,0 (++) (++) (+) (+) (+/-) (+/-) WATER 100 ml + GLYOXYLIC ACID 10 g + Dihydroxyacetone 10 g 2,0 2,0 (+++) (+++) (+) (++) (+) (+/-) WATER 100 ml + GLYOXYLIC ACID 10 g + Ozonized Jojoba Oil 10 q + qlycerol 10 q 2,0 2,0 (++++) (+++) (++) (+) (+) (+/-) WATER 100 ml + GLYOXYLIC ACID 10g + 2,4 Hexadienal 10q 2,0 2,0 (+++) (++) (+) (+) (+/-) (+/-) GLYOXILIC ACID 10a 2,1 2,1 (++++) (+++) (++) (++) (++) (+) + cosmetic base 100 ml GLYOXYLIC ACID 10g + Potassium Iodide 10gr + cosmetic base 100 ml 2,0 2,1 (++) (++) (+) (+) (+/-) (+/-) GLYOXILIC ACID 10g + Dihydroxyacetone 10 g + cosmetic base 100 ml 1,9 1,9 (+++) (+++) (+) (++) (+) (+/-) GLYOXYLIC ACID 10g + Ozonized Jojoba Oil 10 g + cosmetic base 100 ml 2,1 1,9 (++++) (+++) (++) (+) (+) (+/-) GLYOXYLIC ACID 10g + Dihydroxyacetone 10 g + cosmetic base 100 ml 2,0 1,9 (+++) (++) (+) (+) (+/-) (+/-) MEASURED PARAMETER No effect Reduction lower than 25% Reduction between 26 and 50% Reduction between 51 and 75% Reduction between 76 and 90% 100% reduction % Reduction of curves in 20 cm of hair (residual curves/total curves *100) - +/- + ++ +++ ++++ WO 2011/104282 PCT/EP2011/052693 -9- 2015202165 28 Apr 2015

Table 1-B GLYOXYLIC ACID "European" NATURAL CURLY HAIR IRON al 200 Έ STRAIGHTENING EFFECT ASSESSMENT (curve reduction) TESTED MIX pH of initial mix pH after contact with hair washed with basic shampoo after no. 1 washing and drying after no. 2 washings and dryings after no. 3 washings and dryings after no. 4 washings and dryings after no. 5 washings and dryings after no. 6 washings and dryings WATER 100 ml 5,5 6,0 (-) (-) (-) (-) (-) (-) WATER 95 ml + GLYOXYLIC ACID 5 q 2,1 2,1 (+++) (++) (++) (+) (+) (+/-) WATER 90 ml + GLYOXYLIC ACID 10 a 2,0 2,0 (++++) (+++) (+++) (++) (++) (++) WATER 85 ml + GLYOXYLIC ACID 15 q 1,8 1,8 (+++) (+++) (+++) (+++) (++) (++) WATER 80 ml + GLYOXYLIC ACID 20 q 1,6 1,6 (++) (++) (+) (+) (+) (+/-) WATER 80 ml + GLYOXYLIC ACID 25 q 1,5 1,5 (++) (++) (+) (+) (+) (+/-) WATER 100 ml + GLYOXYLIC ACID 10 g + Potassium Iodide 10 q 2,0 2,0 (++) (++) (+) (+) (+/-) (+/-) WATER 100 ml + GLYOXYLIC ACID 10 g + Dihydroxyacetone 10 g 2,0 2,0 (+++) (+++) (++) (++) (+) (+) WATER 100 ml + GLYOXYLIC ACID 10 g + Ozonized Jojoba Oil 10 q + qlycerol 10 q 2,0 2,0 (++++) (+++) (++) (+) (+) (+) WATER 100 ml + GLYOXYLIC ACID 10g + 2,4 Hexadienal 10q 2,0 2,0 (+++) (++) (+) (+) (+) (+) GLYOXYLIC ACID ioa 2,1 2,1 (++++) (+++) (++) (++) (++) (+) + cosmetic base 100 ml GLYOXYLIC ACID 10g + Potassium Iodide 10gr + cosmetic base 100 ml 2,0 2,1 (+++) (++) (++) (++) (+) (+) GLYOXYLIC ACID 10g + Dihydroxyacetone 10 g + cosmetic base 100 ml 1,9 1,9 (+++) (+++) (++) (++) (+) (+) GLYOXYLIC ACID 10g + Ozonized Jojoba Oil 10 g + cosmetic base 100 ml 2,1 1,9 (++++) (+++) (++) (++) (+) (+) GLYOXYLIC ACID 10g + Dihydroxyacetone 10 g + cosmetic base 100 ml 2,0 1,9 (+++) (++) (++) (++) (+) (+) MEASURED PARAMETER No effect Reduction lower than 25% Reduction between 26 and 50% Reduction between 51 and 75% Reduction between 76 and 90% 100% reduction % Reduction of curves in 20 cm of hair (residual curves/total curves *100) - +/- + ++ +++ ++++ WO 2011/104282 PCT/EP2011/052693 - 10- 2015202165 28 Apr 2015

Table 1-C GLYOXYLIC ACID "AFRO" NATURAL CURLY HAIR IRON at 200°C VOLUME REDUCTION ASSESSMENT (reduction of hair spatial volume) TESTED MIX pH of initial mix pH after contact with hair washed with basic shampoo after no. 1 washing and drying after no. 2 washings and dryings after no. 3 washings and dryings after no. 4 washings and dryings after no. 5 washings and dryings after no. 6 washings and dryings WATER 100 ml 5,5 6,0 (-) (-) (-) (-) (-) (-) WATER 95 ml + GLYOXYLIC ACID 5 q 2,1 2,1 (++) (++) (+) (+) (+/-) (+/-) WATER 90 ml + GLYOXYLIC ACID 10 a 2,0 2,0 (++++) (+++) (++) (++) (++) (+) WATER 85 ml + GLYOXYLIC ACID 15 q 1,8 1,8 (+++) (+++) (++) (++) (++) (+) WATER 80 ml + GLYOXYLIC ACID 20 q 1,6 1,6 (++) (++) (+) (+) (+) (+) WATER 80 ml + GLYOXYLIC ACID 25 q 1,5 1,5 (++) (++) (+) (+) (+) (+) WATER 100 ml + GLYOXYLIC ACID 10 g + Potassium Iodide 10 q 2,0 2,0 (++) (++) (+) (+) (+) (+) WATER 100 ml + GLYOXYLIC ACID 10 g + Dihydroxyacetone 10 9 2,0 2,0 (+++) (+++) (+) (++) (+) (+) WATER 100 ml + GLYOXYLIC ACID 10 g + Ozonized Jojoba Oil 10 q + glycerol 10 q 2,0 2,0 (++++) (+++) (++) (++) (+) (+) WATER 100 ml + GLYOXYLIC ACID 10g + 2,4 Hexadienal 10q 2,0 2,0 (+++) (++) (++) (+) (+) (+) GLYOXYLIC ACID ioa + cosmetic base 100 ml 2,1 2,1 (++++) (+++) (++) (++) (++) (+) GLYOXYLIC ACID 10g + Potassium Iodide 10gr + cosmetic base 100 ml 2,0 2,1 (++) (++) (+) (+) (+/-) (+) GLYOXYLIC ACID 10g + Dihydroxyacetone 10 g + cosmetic base 100 ml 1,9 1,9 (+++) (+++) (+) (++) (+) (+) GLYOXYLIC ACID 10g + Ozonized Jojoba Oil 10 g + cosmetic base 100 ml 2,1 1,9 (++++) (+++) (++) (+) (+) (+) GLYOXYLIC ACID 10g + Dihydroxyacetone 10 g + cosmetic base 100 ml 2,0 1,9 (+++) (++) (++) (+) (+) (+) MEASURED PARAMETER No effect Reduction lower than 25% Reduction between 26 and 50% Reduction between 51 and 75% Reduction between 76 and 90% 100% reduction % Reduction of hair volume (circumference of lock with 1.0 g weight measured at half length) (final diameter/initial diameter Ί00) - +/- + ++ +++ ++++ WO 2011/104282 PCT/EP2011/052693 - 11 - 2015202165 28 Apr 2015

Table 1-D GLYOXYLIC ACID "European" NATURAL CURLY HAIR IRON at 200°C VOLUME REDUCTION ASSESSMENT (reduction of hair spatial volume) TESTED MIX pH of initial mix pH after contact with hair washed with basic shampoo after no. 1 washing and drying after no. 2 washings and dryings after no. 3 washings and dryings after no. 4 washings and dryings after no. 5 washings and dryings after no. 6 washings and dryings WATER 100 ml 5,5 6,0 (-) (-) (-) (-) (-) (-) WATER 95 ml + GLYOXYLIC ACID 5 q 2,1 2,1 (+++) (++) (++) (++) (+) (+/-) WATER 90 ml + GLYOXYLIC ACID 10 a 2,0 2,0 (++++) (+++) (+++) (++) (++) (++) WATER 85 ml + GLYOXYLIC ACID 15 g 1,8 1,8 (+++) (+++) (+++) (+++) (++) (++) WATER 80 ml + GLYOXYLIC ACID 20 q 1,6 1,6 (++) (++) (+) (+) (+) (+) WATER 80 ml + GLYOXYLIC ACID 25 g 1,5 1,5 (++) (++) (++) (++) (+) (+) WATER 100 ml + GLYOXYLIC ACID 10 g + Potassium Iodide 10 q 2,0 2,0 (++) (++) (++) (+) (+) (+) WATER 100 ml + GLYOXYLIC ACID 10 g + Dihydroxyacetone 10 9 2,0 2,0 (+++) (+++) (++) (++) (+) (+) WATER 100 ml + GLYOXYLIC ACID 10 g + Ozonized Jojoba Oil 10 q + glycerol 10 g 2,0 2,0 (++++) (+++) (++) (++) (+) (+) WATER 100 ml + GLYOXYLIC ACID 10g + 2,4 Hexadienal 10q 2,0 2,0 (+++) (++) (+) (+) (+) (+) GLYOXYLIC ACID ioa + cosmetic base 100 ml 2,1 2,1 (++++) (+++) (++) (++) (++) (+) GLYOXYLIC ACID 10g + Potassium Iodide 10gr + cosmetic base 100 ml 2,0 2,1 (+++) (++) (++) (++) (+) (+) GLYOXYLIC ACID 10g + Dihydroxyacetone 10 g + cosmetic base 100 ml 1,9 1,9 (+++) (+++) (++) (++) (+) (+) GLYOXYLIC ACID 10g + Ozonized Jojoba Oil 10 g + cosmetic base 100 ml 2,1 1,9 (++++) (+++) (++) (++) (+) (+) GLYOXYLIC ACID 10g + Dihydroxyacetone 10 g + cosmetic base 100 ml 2,0 1,9 (+++) (++) (++) (++) (+) (+) MEASURED PARAMETER No effect Reduction lower than 25% Reduction between 26 and 50% Reduction between 51 and 75% Reduction between 76 and 90% 100% reduction % Reduction of hair volume (circumference of lock with 1.0 g weight measured at half length) (final diameter/initial diameter Ί00) - +/- + ++ +++ ++++ WO 2011/104282 PCT/EP2011/052693 12 2015202165 28 Apr 2015

TABLE 1 N. Name INCI 1 1,6-HEXANEDIAMINE 2 2-AMINOBUTANOL 4 ACETYL MANDELIC ACID 5 ADIPICACID 6 ALUMINUM GLYCINATE 7 ALUMINUM LACTATE 8 ALUMINUM TRIFORMATE 9 AMINOETHYL PROPANEDIOL 10 AMINOMETHYL PROPANEDIOL 11 AMINOMETHYL PROPANOL 12 AMI NOPROPANEDIOL 13 AMMONIA 14 AMMONIUM ACETATE 15 AMMONIUM BICARBONATE 16 AMMONIUM CARBAMATE 17 AMMONIUM CARBONATE 18 AMMONIUM CHLORIDE 19 AMMONIUM GLYCOLATE 20 AMMONIUM HYDROXIDE 21 AMMONIUM LACTATE 22 AMMONIUM MOLYBDATE 23 AMMONIUM NITRATE 24 AMMONIUM PHOSPHATE 25 AMMONIUM THIOCYANATE 26 AMMONIUM VANADATE 27 ASCORBIC ACID 28 AZELAIC ACID 29 BABASSU ACID 30 BAKUHAN 31 BENZILIC ACID 32 BIS-HYDROXYETHYL TROMETHAMINE 33 BISMUTH CITRATE 34 BORIC ACID 35 CALCIUM CARBONATE 36 CALCIUM CITRATE 37 CALCIUM DIHYDROGEN PHOSPHATE 38 CALCIUM HYDROXIDE 39 CALCIUM LACTATE 40 CALCIUM OXIDE 41 CALCIUM PHOSPHATE 42 CITRIC ACID 43 CLAY MINERALS 44 CYCLOHEXYLAMINE INCORPORATED BY REFERENCE (RULE 20.6) PCT/EP2011/052693 2015202165 28 Apr 2015

WO 2011/104282 13 45 DECAPEPTIDE-7 46 DIAMMONIUM CITRATE 47 DIAMMONIUM PHOSPHATE 48 DIBUTYL ETHANOLAMINE 49 DIETHYL ETHANOLAMINE 50 DIMETHYL ISOPROPANOLAMINE 51 DIMETHYL MEA 52 DIOLEOYL EDETOLMONIUM METHOSULFATE 53 DIOLEYL PHOSPHATE 54 DIPOTASSIUM PHOSPHATE 55 DIPROPYLENETRIAMINE 56 DISODIUM FUMARATE 57 DISODIUM PHOSPHATE 58 DISODIUM PYROPHOSPHATE 59 DISODIUM TARTRATE 60 ETHANOLAMINE 61 ETHANOLAMINE HCI 62 ETHYL ETHANOLAMINE 63 FUMARICACID 64 GALACTURONICACID 65 GLUCOHEPTONICACID 66 GLUCONIC ACID 67 GLUCURONIC ACID 68 GLUTARICACID 69 GLYCINE 70 GLYCOLIC ACID 71 GLYOXYLIC ACID 72 GUANIDINE CARBONATE 73 GUANIDINE HCI 74 HYDROBROMICACID 75 HYDROCHLORIC ACID 76 HYDROXYETHYLPIPERAZINE ETHANE SULFONIC ACID 77 IMIDAZOLE 78 ISOBUTYRICACID 79 ISOPROPANOLAMINE 80 ISOPROPYLAMINE 81 LACTIC ACID 82 LACTOBIONIC ACID 83 LAURYL p-CRESOL KETOXIME 84 LITHIUM HYDROXIDE 85 MAGNESIUM ACETATE 86 MAGNESIUM CARBONATE HYDROXIDE 87 MAGNESIUM HYDROXIDE 88 MAGNESIUM LACTATE 89 MAGNESIUM OXIDE 90 MALEIC ACID INCORPORATED BY REFERENCE (RULE 20.6) PCT/EP2011/052693 2015202165 28 Apr 2015

WO 2011/104282 14 91 MALIC ACID 92 MALONICACID 93 MALTOBIONIC ACID 94 MEA-BORATE 95 METAPHOSPHORICACID 96 METHOXY PEG-114/P0LYEPSIL0N CAPROLACTONE 97 METHYLETHANOLAMINE 98 MONOSODIUM CITRATE 99 PENTAPOTASSIUM TRIPHOSPHATE 100 PENTASODIUM TRIPHOSPHATE 101 PHENYL MERCURIC BORATE 102 PHOSPHONOBUTANETRICARBOXYLIC ACID 103 PHOSPHORIC ACID 104 PHOSPHORUS PENTOXIDE 105 POTASSIUM BICARBONATE 106 POTASSIUM BIPHTHALATE 107 POTASSIUM BORATE 108 POTASSIUM CARBONATE 109 POTASSIUM CITRATE 110 POTASSIUM HYDROXIDE 111 POTASSIUM LACTATE 112 POTASSIUM MAGNESIUM ASPARTATE 113 POTASSIUM OXIDE 114 POTASSIUM PHOSPHATE 115 POTASSIUM SODIUM TARTRATE 116 POTASSIUM TARTRATE 117 PROPANE TRICARBOXYLIC ACID 118 QUINICACID 119 RIBONICACID 120 SEBACIC ACID 121 SODIUM ACETATE 122 SODIUM ALUM 1 NATE 123 SODIUM ALUMINUM LACTATE 124 SODIUM ARACHIDATE 125 SODIUM ASPARTATE 126 SODIUM BICARBONATE 127 SODIUM BISULFATE 128 SODIUM BORATE 129 SODIUM BUTOXYETHOXY ACETATE 130 SODIUM CARBONATE 131 SODIUM CITRATE 132 SODIUM FORMATE 133 SODIUM FUMARATE 134 SODIUM GLYCOLATE 135 SODIUM HUMATE 136 SODIUM HYDROXIDE INCORPORATED BY REFERENCE (RULE 20.6) PCT/EP2011/052693 2015202165 28 Apr 2015

WO 2011/104282 15 137 SODIUM LACTATE 138 SODIUM METAPHOSPHATE 139 SODIUM METASILICATE 140 SODIUM OXIDE 141 SODIUM PHOSPHATE 142 SODIUM SESQUICARBONATE 143 SODIUM SILICATE 144 SODIUM SUCCINATE 145 SODIUM TRIMETAPHOSPHATE 146 STRONTIUM HYDROXIDE 147 SUCCINIC ACID 148 SULFURIC ACID 149 TARTARIC ACID 150 TAURINE 151 TEA-DIRICINOLEATE/IPDI COPOLYMER 152 TEA-HYDROIODIDE 153 TEA-SULFATE 154 TETRAHYDROXYETHYL ETHYLENEDIAMINE 155 TETRAPOTASSIUM PYROPHOSPHATE 156 TETRASODIUM PYROPHOSPHATE 157 TRIETHANOLAMINE 158 TRIISOPROPANOLAMINE 159 TRISODIUM PHOSPHATE 160 TRISODIUM SULFOSUCCINATE 161 TRITICUM VULGARE PROTEIN 162 TRITICUM VULGARE SEED EXTRACT 163 TROMETHAMINE 164 UREA 165 URIC ACID 166 ZINC CARBONATE HYDROXIDE 167 ZINC GLYCINATE 168 ZINC HEXAMETAPHOSPHATE 169 ZINC MAGNESIUM ASPARTATE INCORPORATED BY REFERENCE (RULE 20.6) 2015202165 23 Nov 2016 - 16- TABLE 2 • potassium iodide CAS n. 7681-11 -0 (Used as antimicrobial) • dihydroxyacetone CAS n. 96-26-4 (Used as tanning) • Ozonized Jojoba oil (No n, CAS) (Used as emollient) • 2,4 Hexadienal CAS n. 142-83-6 (Used as perfuming ) 5 Where the terms "comprise", "comprises", "comprised" or "comprising" are used in this specification (including the claims) they are to be interpreted as specifying the presence of the stated features, integers, steps or components, but not precluding the presence of one or more other features, integers, steps or components, or group thereof. io The discussion of documents, acts, materials, devices, articles and the like is included in this specification solely for the purpose of providing a context for the present invention. It is not suggested or represented that any or all of these matters formed part of the prior art base or were common general knowledge in the field relevant to the present invention as it existed before the priority date of each claim of is this application.

Claims

The claims defining the invention are as follows: 1) Process for straightening of human hair with permanence in such a condition for a number of washings higher than 5 with water and shampoo, comprising the following application steps: a) Application on hair of a solution containing glyoxylic acid dissolved at a ratio 10% or less in weight; b) Permanence of substance in contact with hair for 15 to 120 minutes; c) Hair drying; and d) Hair straightening with hair straightening iron at temperature of approximately 200+/-50 °C, wherein a procedure of the following steps i to x is excluded: i contacting wavy, curly hair with an alkaline composition comprising a sufficient amount of chemical base to provide alkalinity in the range of at least pH 8.5 to about pH 14 to partially straighten the original configuration of the hair; ii optionally washing the partially straightened hair with water; iii drying the partially straightened hair to a substantially dry state; iv contacting the so-dried hair with an acidic composition having acidity of less than about pH 2.5, the acidic composition comprising at least one compound selected from the group consisting of glyoxylic acid, a glyoxylic amide, and a mixture thereof, present in an amount sufficient to further straighten the configuration of the hair; v covering the so-contacted hair of set iv with a cap and optionally heating the cap-covered hair for a period of up to about 30 minutes; vi removing the cap and drying the further straightened hair to a substantially dried state; vii pressing the substantially dried straightened hair with a heated iron; viii washing the pressed, straightened hair with water, and optionally contacting the washed hair with a hair conditioning composition comprising an oxidizing agent, and optionally, washing the conditioned hair with water; ix blow drying the hair of step viii optionally with a thermal protectant composition on the hair; and x optionally pressing the blow-dried hair with a heated iron, optionally with a hair conditioning composition on the hair.
2) The process as claimed in claim 1, wherein the solution containing glyoxylic acid dissolved at a ratio between 5% and 10% in weight.
3) Process as claimed in claim 1 or claim 2, further comprising prewashing with basic pH (7.5-9.5) shampoo before step a); and for rinsing after step d).
4) Process as claimed in any one of the preceding claims, further comprising human hair washing with acid pH (4.5-5.5 approx.) washing after step d).
5) Process as claimed in one of the preceding claims, wherein step b) has average duration of 60 minutes.
6) Process as claimed in any one of claims 1 to 5, wherein said glyoxylic acid is emulsified in oily solution.
7) Process as claimed in any one of claims 1 to 6, wherein said glyoxylic acid is mixed with at least one of the substances selected from potassium iodide, dihydroxyacetone, Ozonized Jojoba oil and 2,4-Hexadienal.
8) Use of glyoxylic acid for straightening of human hair with permanence in such a condition for a number of washings higher than 5 with water and shampoo, wherein the glyoxylic acid is used in combination with mechanical human hair straightening means.