Description:Field of Invention:
The current invention is in field of reshaping of hair. More particularly, the current invention provides a multi-functional moiety which permanently reshapes or alters the shape of hair through formation of a cross link using two Carbon-Sulphur bonds with a spacer in between and composition and methods thereof.

Background of Invention:
Hair straightening has been known since aeons for making hair look smooth, shiny, streamlined and sleek. Traditionally, hair reshaping is carried out by various techniques which include, but not limited to, use of flat iron or hot comb, chemical relaxers, Japanese hair straightening technique, Brazilian hair straightening technique, or roller set/blow dryer styling.

The above methods can be broadly classified as “Non-Chemical Methods” leading to temporary straightening of hair and “Chemical Methods” which cause reshaping of hair.

Among the non-chemical methods as mentioned above, is the usage of a flat iron, hot comb, or roller set/blow dryer styling. These techniques involve applying heat to hair for brief periods of time, which denatures the keratin and gives the appearance of straighter hair. When the keratin interacts with the surrounding environment, it rapidly returns to its initial state.

Conversely, chemical methods are more long-lasting; these include, but are not limited to, Hair relaxing, RedOx treatment, and Brazilian treatments.

The Brazilian keratin treatment involves applying a cross linking agent such as formaldehyde, glyoxyloyl carbocysteine, or glyoxylic acid to the hair followed by the use of a hot flat iron. The cross-linking agent facilitates bonding between the reactive groups present in the hair keratin. The treatment enhances hair shine, straightens it and reduces frizz. The effect persists for approximately six months, after which gradual reversion to the original hair texture occurs.

In RedOx treatment process, the hair undergoes a series of steps to achieve structural modification. Initially, a reducing agent selected from thioglycolic acid or a salt thereof, thioglycerol, cysteamine, and cysteine or its salt thereof, inorganic sulphites, is applied for 45 minutes to 1 hour, effectively reducing the disulphide bonds in cystine (R-S-S-R) into thiols i.e. converts cystines to cysteines (-RSH). Then the hair is stretched to realign the thiols and heat is applied. In the final phase, H2O2 is used to oxidize the thiols, facilitating the reformation of disulphide bonds (R-S-S-R) in the new locations. The hair treated in this way would curl back as the disulphide bonds in the new locations are not stable. The pH of the first step (reduction step) is around 8.5-9.5 and the second step (oxidation) is carried out at a pH of around 3. The duration of the treatment is 2 to 3 hours.

Hair relaxer composition includes either alkali metal hydroxide like NaOH, LiOH, quaternary ammonium hydroxide or guanidine hydroxide in the pH range of 12-14. It is the hydroxide ion, which is the alkaline chemical species common to all the above-listed relaxers. The hydroxide ion reshapes hair (straightens hair) by a mechanism called beta elimination whereby a disulphide cystine (R-S-S-R) in hair keratin is attacked to form dehydroalanine and a thiolate, which subsequently combine to form a lanthionine bond (R-S-R), liberating a sulphur atom. One disclosure of this technique could be found in US4992267 filed by Wella Corp in 1988.

These lanthionine bonds offer a permanent reshaping of hair. There is no flat iron or heat involved in the process and the alignment of hair as per the destination shape is achieved by the application of this composition as a thick cream on hair. The lanthionines form in the same position where disulphide cystines were broken. The new shape of hair is permanent with good resistance to curling back. This treatment happens at a pH of 12.5 to 13.5. The duration of treatment is 10-20 minutes. One of the techniques of straightening of hair by use lanthionine bonds has been disclosed in WO2002085317 filed by L’Oreal.

The obvious weakness of lanthionization process is high pH which can cause scalp irritation and also damage the hair. The drawback of the Redox process is that it is a 2-step process requiring heat along with the undesired effects of H2O2. Also, H2O2 leads to unwanted oxidation of cystine to cystic acid and thiols via sulfenic acid (RSOH) and sulphonic acid (RSO2H) to sulfonic acid (RSO3H) leading to dulling of hair.

The current invention endeavours to overcome the above cited drawbacks of the prior art by providing a novel method and composition for permanent straightening of hair.

Summary of Invention:
In view of above drawbacks of the prior art, in main aspect, the current invention provides a composition for permanent straightening of hair through formation of a cross link using two Carbon-Sulphur bonds with a spacer in between.

The carbon-sulphur bonds are formed as a covalent bond between the at least two functional groups of an active agent and at least two sulfhydryl groups of two adjacent cysteine residues of keratin protein fibres.

Accordingly, the active agent is multi-functionalised moiety, whereby the carbon-sulphur bond is formed between the active sites of the moiety, preferably placed at the terminal Carbon atoms and the sulfhydryl group of cysteine residues of the keratin fibre.

The composition of the invention requires a treatment time of 30 – 60 minutes and the hair remains straight for longer period than that could be achieved by traditional hair straightening techniques.

Brief Description of Drawings:
Fig. 1 illustrates effect of treatment using Single composition (a cross linking technology using two Carbon-Sulphur bonds with a spacer in between).

Fig. 2 illustrates effect of treatment using Marketed Lye Relaxer.

Fig. 3A illustrates effect of Thioglycolic acid + H2O2

Fig. 3B illustrates effect of treatment using Thioglycolic acid + Dimethyl 2,5 dibromohexanedioate.

Fig. 4 illustrates the effect of water on straightening (Negative control)

Detailed Description of the Invention:
The invention will now be described in detail in connection with certain preferred and optional embodiments, so that various aspects thereof may be more fully understood and appreciated. However, any skilled person will appreciate the extent to which such embodiments could be extrapolated in practice.

Unless specified otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art, to which this invention belongs. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, the preferred methods and materials are described.

Unless stated to the contrary, any of the words “contains”, “containing”, “including,” “includes,” “comprising,” and “comprises” mean “including without limitation” and shall not be construed to limit any general statement that it follows to the specific or similar items or matters immediately following it. Embodiments of the invention are not mutually exclusive but may be implemented in various combinations. The described embodiments of the invention and the disclosed examples are given for the purpose of illustration rather than limitation of the invention.

Further, words like “a”, “an”, “at least” and “the” should be construed to not only cover singular quantities but also plural quantities of the elements immediately following them.

For the purpose of this specification, the term “multi-functionalised active moiety” encompasses such active compounds which are straight or branched chain of alkane, alkene, alkyne, aromatic compound, heterocyclic or homocyclic group capable of covalently binding at least two thiols, wherein the reactive groups can be mono or bis-Michael acceptors like maleic acid, succinic acid, itaconic acid, fumaric acid, acrylate, methacylate groups, or electrophilic groups such as isocyanate, isothiocyanate, epoxide, reactive hetero aromatic compounds such as triazole, or alkene, or alkyne, or electrophilic group attached with charged amino acid, an electrophilic moiety containing a leaving group that has ability to attract electrons such as halogen, triazolyl, imidazole, phosphate, phosphonate, phosphinate, amide, imide, amine, tosylate, hydroxyl, carbonate, carboxylate, urethane, urea, and ammonium.

The multi-functionalised active moiety could be triazole-activated dicarboxylic acids, wherein the dicarboxylic acid could be malonic acid, succinic acid, tartaric acid, glutaric acid, adipic acid and combinations thereof.

The alkene moiety as a Michael acceptor on the active molecule could be located, other than at the ends of the molecule and on its ends carry thiol groups e.g. dithio maleate whereby the thiol groups interact with thiols on either side of the hair keratin forming disulfide bonds or one thiol on the active molecule can form a disulfide bond with one thiol on one side of hair keratin and the alkene site on the active molecule involves in Michael addition with another thiol on the other side of the hair keratin.

The current invention describes a composition and method for hair straightening which is based on formation of a carbon-sulphur bond between sulfhydryl or thiol group of the cysteine residue of the Keratin Protein and the terminal functional group of the multi-functionalised active agent.

In accordance with the invention, the multi-functionalised active agent has following general Structure I:
FG- R-FG'
(I)
wherein,
FG, FG’ which are connected with a carbon chain (-R) and having reactive moieties on either end, capable of reacting to form covalent bonds with at least two thiols, which include derivatives of Michael acceptors like maleic acid, succinic acid, itaconic acid, fumaric acid, acrylate, methacrylate, or reactive hetero aromatic compounds such as triazole, or electrophilic groups such as isocyanate, isothiocyanate, epoxide, alkene, or alkyne, or electrophilic group attached with charged amino acid, an electrophilic moiety containing a leaving group that has ability to attract electrons such as halogen, triazolyl, imidazole, phosphate, phosphonate, phosphinate, amide, imide, amine, tosylate, hydroxyl, carbonate, carboxylate, urethane, urea, and ammonium, and

R = a spacer group selected from a straight or branched alkane, alkene, alkyne, or aromatic compound, or functionalised straight or branched alkane, alkene, alkyne or aromatic compound wherein functionalisation could be amide or ester or ether, heterocyclic or homocyclic group or carbon chains containing one or more heteroatoms such as N, S, O.

When two molecules of Structure 1 are used to cross link with two adjacent thios, the FG or FG’ can be amines which can be linked by bis-isocyanate or dialdehydes such as orthopthalaldehyde, alkyl dialdehydes, or glyoxal.

(1) FG and FG’ can be same or different and are selected from group consisting of Michael acceptors like maleic acid, succinic acid, glutaric acid, itaconic acid, fumaric acid, acrylate, methacrylate, or heteroaromatic groups such as triazole, or electrophilic groups such as isocyanate, isothiocyanate, epoxide, or alkene, alkyne covalently linked to R selected from an alkyl group having carbon chain length (2-10) that form covalent Carbon-sulphur bonds between two sulphur atoms of thiols on either side of hair keratin.

A cocktail can be used with different values for ’n’

(2) In the second object of invention, the group -R containing two or more substituents selected from the group consisting of a halogen, cyano, alkoxy, hydroxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, wherein the substitute groups react with two thiols on either side of hair keratin to form covalent Carbon-Sulphur bonds.

A cocktail can be used with different values for 'n’

(3) Two molecules of Structure 1 with different FG and FG’ wherein FGs are selected from Michael acceptors like maleic acid, succinic acid, glutaric acid, itaconic acid, fumaric acid, acrylate, methacrylate, or electrophilic groups such as epoxide, isocyanate, isothiocyanate, alkene, alkyne, or electrophilic moiety with a leaving group, or heteroatomic group, and the other ones (FG’) are amine, and these two molecules react with two thiols on hair through their ends containing Michael acceptors or electrophilic groups in a mild basic medium.

(4) Optionally, the amine ends (FG’s) of these two covalent molecules linked to thiols at either side of hair keratin are linked by bis isocyanate or bis maleate, aromatic or alkyl dialdehydes such as mono- or di-ortho phthalaldehyde, glyoxal through a covalent bond.

one molecule attaching to thiol on one side of hair keratin can be a charged amino acid derivative containing free carboxylic group / carboxylate ion and functionalized with a Michael acceptor or an electrophilic group, electrophilic moiety containing a leaving group described earlier, and another molecule attached to another thiol at the other side of hair keratin can be a charged amino acid derivative containing free amino group / quaternary amine and functionalized with a Michael acceptor or an electrophilic group or electrophilic moiety with leaving group described in this art. These carboxylic acid / carboxylate ion and amino group / quaternary amine interact electrostatically on hair.

A molecule that attaches to thiol on one side of hair keratin through a Michael acceptor or an electrophilic moiety containing an azide group and another molecule reacting with thiol on the other side of hair keratin through a Michael acceptor or an electrophilic moiety containing an alkyne group, wherein the alkyne and azide ends are clicked together to form a triazole covalently linking two thiols on either side of hair keratin.

The molecule connecting two thiols at either side on the hair keratin or keratin fibre is a dicarboxylic acid activated with triazoles on its both ends. The dicarboxylic acid can be malonic acid, succinic acid, tartaric acid, glutaric acid, adipic acid etc.

The alkene moiety as a Michael acceptor on the active molecule could be located other than at the ends of the molecule and on its ends carry thiol groups e.g. dithio maleate whereby the thiol groups interact with thiols on either side of the hair keratin forming disulfide bonds or one thiol on the active molecule can form a disulfide bond with one thiol on one side of hair keratin and the alkene site on the active molecule involves in Michael addition with another thiol on the other side of the hair keratin.
In one embodiment, the invention provides a composition for permanent straightening of hair, which comprises of:
A reducing agent selected from the group consisting of thioglycolic acid and its derivative salts and esters, thioglycerol, thiolactic acid and its derivative salts and esters, cysteine and its derivatives, cysteamine, inorganic Sulphites, sodium metabisulfite, other inorganic bisulphites, that break the disulfide bonds into thiols, and

an active agent of general Structure (I) that has at least two reactive groups as defined above at either ends with certain carbon chain length capable of reacting with at least two free thiols on hair keratin, and

One or more cosmetically acceptable excipients containing surfactants, emulsifiers, thickeners, polyols, humectants, pH adjusting agent, cationic conditioners, emollients, oils, water, preservatives and fragrance.

In accordance with above embodiment, the pH of the composition is mildly basic or alkaline with pH varying from 8.5 to 10.

In one of the embodiments, the invention provides a two-step method for permanent straightening of hair comprises:

Reduction of disulphide bonds into thiol, which is achieved in the first step using a reducing agent and in the second step, instead of hydrogen peroxide, the reactive moiety with in-between (General Structure 1) forms a cross linking using two Carbon-Sulphur bonds between two thiols. One bond, on each sulphur, on either side of hair keratin.

The active agent of General Structure I has two functional groups FG and FG’, which are selected from, but not limited to, Michael acceptors like maleic acid, succinic acid, itaconic acid, glutaric acid, fumaric acid, acrylate group, methacrylate group, electrophilic groups such as isocyanate, isothiocyanate, epoxide, reactive hetero aromatic compounds such as triazole, alkene, or alkyne, or electrophilic group attached with charged amino acid, an electrophilic moiety containing a leaving group that has ability to attract electrons such as halogen, triazolyl, imidazole, phosphate, phosphonate, phosphinate, amide, imide, amine, tosylate, hydroxyl, carbonate, carboxylate, urethane, urea, and ammonium, at each end which form a covalent bond between the two sulphur atoms of two thiols on either side of hair keratin but with a spacer in between them. Thus, the two sulphurs in two thiols are linked but with a spacer ‘R’ in between them.

This alters the secondary structure of Keratin in hair, thereby offering strength and longevity to the shape of hair. Also, the peroxide-associated oxidative damage to keratin protein is avoided. Longevity is improved (as achieved with lanthionization) because the spacer between the two sulphur atoms of two thiols prevents the free thiols from destabilizing this cross linked thiol-thiol bridging using two Carbon-Sulphur bonds with a spacer in between (R-S-R-S-R), as they could do with R-S-S-R. Treatment lasts anywhere from 30mins to 1hour.

In accordance with above embodiment, the two-step process for permanent straightening of hair comprises:

applying a composition containing the reducing agent;
applying the composition containing the active agent of Structure 1, without rinsing of hair;
leaving the composition of step (b) for 30 – 60mins, and
rinsing the hair,
Optionally flat ironing or hot blow drying

In an alternative embodiment, the two-step process for permanent straightening of hair comprising following step:
applying a composition containing the reducing agent first on the hair;
Leave the composition of step (a) for 30-60 minutes and the rinse the hair;
Hot Flat iron the hair;
Apply the composition containing the active agent of Structure 1;
Leave the composition of step (d) for 30 – 60mins, and
Rinse the hair.

In yet another alternative embodiment, the two-step process for permanent straightening of hair comprising:
applying a composition containing the reducing agent first on the hair;
Leave the composition for 30-60 minutes and the rinse the hair;
Apply the composition containing the active agent of Structure 1 and hot Flat iron the hair;
Leave the composition containing active agent of Structure 1 for 30 – 60 mins, and
Rinse the hair.

In another embodiment, the invention provides a single step method for permanent straightening of hair. The process entails applying the active agent and the reducing agent simultaneously or sequentially with a thick paste cladding the hair in the stretched condition. Wherever the disulfide bond is broken, the active agent reacts with the two thiols and connects them through a cross linking using two Carbon-Sulphur bonds with a spacer in between. The thiols, resulting from the disulfide bond reduction, do not require realignment as the hair was kept in the desired shape during the course of the treatment. After this treatment, optionally, heat can be applied using a hot flat iron or a hot blow drying. As a result, according to the embodiment, a single composition can perform reduction and re-bonding between two thiols in a single step.

In accordance with above embodiment, the single step process for reshaping of hair, using the composition of the invention, comprises following steps;
applying the single composition containing the reducing agent, the active agent as a thick product cladding on stretched hair;
leaving the product of step (a) for 30 – 60mins, and
rinsing of the hair,
Optionally flat ironing or hot blow drying

According to this embodiment, a pH of 8.5 to 9.5 is suitable for both the active agent and the reducing agent.

The treatment lasts anywhere from 30mins to 1hour.

The composition of invention can also be deployed to strengthen the synthetic keratin or the keratin digested from other sources such as chicken feather so that it is amenable for efficient extrusion at desired speed into fibres with appropriate diameter and tensile strength.

Advantages of Invention:
The pH of the entire process is at low alkaline pH unlike Relaxers, hence alkali-induced damage to scalp and hair is reduced.

There is no peroxide induced damage as is the case with the Redox process.
The longevity of hair shape is better than the redox process.

The strength of the hair is better than both the processes as there are new covalent carbon-sulphur bonds formed and there is no elimination of sulphur atom as is the case in lanthionization or Relaxer process.

Advantageously, the reduction and formation of a cross link, using two Carbon-Sulphur bonds with a spacer in between, is achieved with one composition or sequential application of two compositions one after the other without any rinsing of first composition. Therefore, this method offers better convenience in terms of duration and simplicity of treatment compared to the two-step Redox process known as Japanese straightening.
EXAMPLES
Example 1: Single Step Composition for cross linking using two Carbon-Sulphur bonds with a spacer in between
Table 1

S. No. Phase Ingredients %
1 A Aqua 37
2 B Propylene Glycol 10
3 Dimethyl 2, 5-dibromohexanedioate 5
4 C PEG-75 lanolin 2
5 Petrolatum 10
6 Cetostearyl Alcohol 10
7 Polysorbate 60 1
8 Cetyl Alcohol 2
9 Light Liquid Paraffin 8
10 D Thioglycolic acid 8
11 E Ethanolamine 6
12 F Parfum 1
Total 100

The process for manufacturing the composition of Example 1 comprises following steps:
Taking sufficient amount of water in a vessel;
mixing sufficient amount of Propylene Glycol and Dimethyl 2, 5-dibromohexanedioate in a separate vessel;
adding the mixture of step (b) to the vessel of step (a) and heating the mixture to 80°C;
mixing sufficient amounts of PEG-75 lanolin; Petrolatum; Cetostearyl Alcohol; Polysorbate 60; Cetyl Alcohol and Light Liquid Paraffin in a vessel and heating the vessel to 80°C;
adding and the mixture of step (d) to vessel of step (c) and homogenising;
cooling the mixture of step (e) to 40°C;
adding sufficient amount of thioglycolic acid to the cooled mixture of step (f);
adding ethanolamine to the mixture of step (g) to maintain the pH in range of 9 – 9.5, and
add perfume to the mixture of step (h).
Method of Application of the composition of Example 1:
applying the single composition containing the reducing agent, the active agent of as a thick product cladding on stretched hair;
leaving the product of step (a) for 30 – 60mins, and
rinsing of the hair,
Optionally flat ironing or hot blow drying

Example 2: Two Composition for a cross linking using two Carbon-Sulphur bonds with a spacer in between:
Table 2:
Step 1: Reduction Composition
S. No. Phase INCI %
1 A Aqua 38.95
2 Sodium salt of Hydroxyethylidene-1,1-diphosphoric acid 0.05
3 Propylene Glycol 3
4 Hydroxyethyl Ethylcellulose
Polysorbate 60
Sodium Phosphate
Disodium Phosphate
Sodium Nitrate
Glyoxal
Aqua 0.5
5 B Cetearyl Alcohol
Ceteareth-20 8
6 C Dimethicone
Aqua
Amodimethicone
Laureth-23
Polyquaternium-10
Laureth-4
Phenoxyethanol
Propylene Glycol 0.5
7 D Aqua
Ammonium Thioglycolate (50% solution) 21
8 E Aqua
Ammonium Hydroxide 2
9 F Aqua 19
10 F Ammonium Bicarbonate 2
11 G Ethanolamine 3
12 G Dimethicone
Dimethiconol 1
13 H Parfum 1
Total 100

The process for manufacturing the composition of Example 3 comprises following steps:
Taking sufficient amount of water in a vessel and heat the water till 80°C;
during heating, sequentially mixing sufficient amount of Sodium salt of Hydroxyethylidene-1,1-diphosphoric acid, Propylene Glycol, Hydroxyethyl Ethylcellulose, Polysorbate 60, Sodium Phosphate, Disodium Phosphate, Sodium Nitrate, Glyoxal and water to the vessel of step (a);
mixing sufficient amount of Cetearyl Alcohol and Ceteareth-20 in a vessel and heat the mixture to 80°C;
adding solution of step (c) to vessel of step (b) and heat the solution till 80°C and homogenise;
cooling the solution of step (d) to 45°C;
adding mixture of Dimethicone, Aqua, Amodimethicone, Laureth-23, Polyquaternium-10, Laureth-4, Phenoxyethanol, Propylene Glycol to mixture of step (e);
adding aq. Ammonium Thioglycolate to the solution of step (f)
adding sufficient amount of aq. Ammonium bicarbonate to the vessel of step (g);
adding sufficient amount of mixture of Ethanolamione, Dimethicone and Dimethiconol to the vessel of step (h), and till pH is maintained at 8.5 – 9.5, and
adding perfume to mixture of step (i).
Table 3
Step 2: Composition for a cross linking using two Carbon-Sulphur bonds with a spacer in between (using Dimethyl 2, 5-dibromohexanedioate)
S. No. Phase INCI %
1 A Aqua 75.4
2 Sodium salt of Hydroxyethylidene-1,1-diphosphoric acid 0.05
3 Sodium Lauryl Sulphate 0.05
4 Aqua 2
5 Sodium Stannate 0.01
6 Aqua 2
7 Tetrasodium Pyrophosphate 0.05
8 B Propylene Glycol 4
9 Dimethyl 2, 5-dibromohexanedioate 2
10 C Cetearyl Alcohol
Ceteareth-20 8
11 D Polyquaternium-37
Propylene Glycol Dicaprylate/Dicaprate
PPG-1 Trideceth-6
Aqua
C10-11 Isoparaffin
Methacrylic Acid Stearyl Methacrylate Copolymer
Sorbitan Oleate
Citric Acid 0.5
12 E Amodimethicone
Trideceth-12
Cetrimonium Chloride 3
13 F Dimethicone
Dimethiconol 1
14 G MEA 2
Total 100

The process for manufacturing the composition of Example 3 comprises following steps:
Taking sufficient amount of water in a vessel and heat the water till 80°C;
during heating, sequentially Sodium salt of Hydroxyethylidene-1,1-diphosphoric acid, Sodium Lauryl Sulphate, Aqua, Sodium Stannate, Aqua, Tetrasodium Pyrophosphate to the vessel of step (a);
preparing mixture of Propylene Glycol and Dimethyl 2, 5-dibromohexanedioate;
mixing sufficient amount mixture of step (c) to vessel of step (b);
mixing sufficient amount of Cetearyl Alcohol and Ceteareth-20 in a vessel and heating the mixture to 80°C;
adding solution of step (e) to vessel of step (d) and heat the solution till 80°C and homogenise
during homogenisation, adding sufficient quantity of mixture containing Polyquaternium-37; Propylene Glycol Dicaprylate/Dicaprate; PPG-1; Trideceth-6; Aqua; C10-11 Isoparaffin; Methacrylic Acid Stearyl, Methacrylate Copolymer, Sorbitan Oleate and Citric Acid
cooling the solution of step (g) to 45°C;
adding mixture of Amodimethicone, Trideceth-12, Cetrimonium Chloride to vessel of step (h);
adding sufficient amount of mixture of, Dimethicone and Dimethiconol to the vessel of step (i), and
adding MEA till pH is maintained at 8 – 8.5.

Method of Application:
Applying the composition of table 2, and
Applying the composition of table 3, without washing or rinsing hair

Example 3: Lye Relaxer Composition
Table 4
S. No. Phase Ingredients %
1 A Aqua 54
2 B Propylene Glycol 10
3 C PEG-75 lanolin 2
4 Petrolatum 10
5 Cetostearyl Alcohol 10
6 Polysorbate 60 1
7 Cetyl Alcohol 2
8 Light Liquid Paraffin 8
9 E NaOH 2
10 F Parfum 1
Total 100

The process for manufacturing the composition of Example 2 comprises following steps:
Taking sufficient amount of water in a vessel;
mixing sufficient amount of Propylene Glycol to the vessel of step (a) and heating the mixture to 80°C;
mixing sufficient amounts of PEG-75 lanolin; Petrolatum; Cetostearyl Alcohol; Polysorbate 60; Cetyl Alcohol and Light Liquid Paraffin in a vessel and heating the vessel to 80°C;
adding the mixture of step (c) to vessel of step (b) and homogenising this mixture;
adding NaOH at Room Temperature to the mixture of step (d) to maintain the pH in range of 9 – 9.5, and
add perfume to the mixture of step (e).

Example 4: Redox Hair Straightening
Table 5
Step 1: Reduction
S. No. Phase INCI %
1 A Aqua 38.95
2 Sodium salt of Hydroxyethylidene-1,1-diphosphoric acid 0.05
3 Propylene Glycol 3
4 Hydroxyethyl Ethylcellulose
Polysorbate 60
Sodium Phosphate
Disodium Phosphate
Sodium Nitrate
Glyoxal
Aqua 0.5
5 B Cetearyl Alcohol
Ceteareth-20 8
6 C Dimethicone
Aqua
Amodimethicone
Laureth-23
Polyquaternium-10
Laureth-4
Phenoxyethanol
Propylene Glycol 0.5
7 D Aqua
Ammonium Thioglycolate (50% Solution) 21
8 E Aqua
Ammonium Hydroxide 2
9 F Aqua 19
10 Ammonium Bicarbonate 2
11 G Ethanolamine 3
12 Dimethicone
Dimethiconol 1
13 H Parfum 1
Total 100

The process for manufacturing the composition of Example 3 comprises following steps:
Taking sufficient amount of water in a vessel and heat the water to 80°C;
sequentially mixing sufficient amount of Sodium salt of Hydroxyethylidene-1,1-diphosphoric acid, Propylene Glycol, Hydroxyethyl Ethylcellulose, Polysorbate 60, Sodium Phosphate, Disodium Phosphate, Sodium Nitrate, Glyoxal to the vessel of step (a);
mixing sufficient amount of Cetearyl Alcohol and Ceteareth-20 in a vessel and heat the mixture to 80°C;
mixing sufficient amount of Dimethicone, Aqua, Amodimethicone, Laureth-23, Polyquaternium-10, Laureth-4, Phenoxyethanol and Propylene Glycol to form a solution;
adding the solution of step (d) to the vessel of step (c) after cooling down the mixture to 45°C;
Mixing sufficient amount of Ammonium Thioglycolate in water;
Adding sufficient amount of aq. Ammonium Hydroxide to the vessel of step (f);
Mixing sufficient quantity of Ammonium Bicarbonate
adding the solution of step (h) to vessel of step (g)
adding sufficient amount of Ethanolamine to the vessel of step (i) to maintain pH in range of 8.5 – 9.5;
adding sufficient amount of Dimethicone to the vessel of step (j);
adding sufficient amount of Dimethiconol to the vessel of step (k), and
adding perfume to the mixture of step (h).

Table 6
Step 2: Neutralizer with hydrogen peroxide
S.No. Phase INCI %
1 A Aqua 79.8
2 Sodium salt of Hydroxyethylidene-1,1-diphosphoric acid 0.05
3 Sodium Lauryl Sulphate 0.05
4 Aqua 2
5 Sodium Stannate 0.01
6 Aqua 2
7 Tetrasodium Pyrophosphate 0.05
8 B Cetearyl Alcohol
Ceteareth-20 8
9 C Polyquaternium-37
Propylene Glycol Dicaprylate/Dicaprate
PPG-1 Trideceth-6
Aqua
C10-11 Isoparaffin
Methacrylic Acid Stearyl Methacrylate Copolymer
Sorbitan Oleate
Citric Acid 0.5
10 D Amodimethicone
Trideceth-12
Cetrimonium Chloride 3
11 E Aqua
12 Hydrogen Peroxide
Aqua 3
13 F Dimethicone
Dimethiconol 1
14 G Aqua 0.5
15 Phosphoric Acid 0.04
Total 100

The process for manufacturing the composition of Example 3 comprises following steps:
Taking sufficient amount of water in a vessel and heat the water to 80°C;
sequentially mixing sufficient amount of Sodium salt of Hydroxyethylidene-1,1-diphosphoric acid, Sodium Lauryl Sulphate; Sodium Stannate; and Tetrasodium Pyrophosphate to the vessel of step (a) and heat till 80°C;
mixing sufficient amount of Cetearyl Alcohol and Ceteareth-20 in a vessel and heat the mixture to 80°C;
adding solution of step (c) to vessel of step (a) and heat the solution till 80°C and homogenise
adding mixture of Polyquaternium-37; Propylene Glycol; Dicaprylate/Dicaprate; PPG-1 Trideceth-6; Aqua; C10-11 Isoparaffin; Methacrylic Acid Stearyl; Methacrylate Copolymer, Sorbitan Oleate and citric acid Citric Acid to mixture of step (d) while homogenisation;
cooling the solution of step (e) to 45°C;
adding a mixture of Amodimethicone; Trideceth-12 and Cetrimonium Chloride the solution of step (f) to the vessel of step (c) after cooling down the mixture to 45°C to the solution of Step (f);
adding sufficient amount of aq. Hydrogen Peroxide solution to the vessel of step (g);
adding sufficient amount of mixture of Dimethicone and Dimethiconol to the vessel of step (h), and
adding aq. Phosphoric acid to vessel of step (i) till pH is maintained at 2.5 – 3.5.
, Claims: A multi-functionalised compound of Structure 1, which is capable of covalently binding two adjacent free thiols present in keratin for permanent straightening of hair,
FG- R-FG'
(Structure I)
wherein,
FG and FG’ can be same or different and are selected from group consisting of a Michael acceptor, a heteroaromatic group or an electrophilic group or an electrophilic moiety containing a leaving group;
and
R is a spacer group selected from a straight or branched alkane, alkene, alkyne, or aromatic compound, or functionalised straight or branched alkane, alkene, alkyne or aromatic compound wherein functionalisation could be amide or ester or ether, heterocyclic or homocyclic group or carbon chains containing one or more heteroatoms such as N, S, O covalently bonded to FG and FG’ .

The spacer group R in Claim 1 contains a carbon chain length 1 to 30 , more preferably 2 to15, and most preferably 2 to 10.

The compound as claimed in Claim 1, wherein FG or FG’ are same selected from Michael acceptors.

The compound as claimed in Claim 3, wherein the Michael acceptor is selected from acrylate group, methacrylate group, maleic acid, fumaric acid, succinic acid, glutaric acid, itaconic acid.

The compound as claimed in Claim 3 is, preferably, Ethylene glycol dimaleate.

The compound as claimed in Claim 1, where in FG or FG’ are electrophilic moieties containing same or different leaving groups which include and not limited to such as halogen, triazolyl, imidazole, phosphate, phosphonate, phosphinate, amide, imide, amine, tosylate, hydroxyl, carbonate, carboxylate, urethane, urea, ammonium that has ability for electrons.

The compound as claimed in Claim 6, is a triazole-activated dicarboxylic acid, wherein the dicarboxylic acid is selected from malonic acid, succinic acid, tartaric acid, glutaric acid, adipic acid and the like.

The compound as claimed in Claim 1, where in FG or FG’ are electrophilic groups selected from epoxide, isocyanate, isothiocyanate, alkene, alkyne.

The compound as claimed in Claim 8 is a bis-isocyanate with a spacer R.
The compound as claimed in Claim 8 is a bis-epoxide with a spacer R.

The multi-functionalised compound as claimed in Claim 1, wherein the R contains two or more substituents selected from the group consisting of a halogen, cyano, alkoxy, hydroxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl.

The multi-functionalised compounds as claimed in Claim 11 could be without FG and FG’.

The compound as claimed in Claim 12 is Dimethyl 2,5-dibromoadipate.

Two multi-functionalised compounds of Structure 1, wherein FGs of each molecule are capable of covalently binding two adjacent free thiols present in keratin for permanent straightening of hair,
FG- R-FG'
(Structure I)
wherein,
FG and FG’ are different, wherein FG is selected from group consisting of a Michael acceptor, or a heteroatomic group, an electrophilic group or an electrophilic moiety containing a leaving group which react with thiols on hair keratin and FG’ is selected from amine, quaternary amine, and carboxylate ion.

R is a spacer group selected from a straight or branched alkane, alkene, alkyne, or aromatic compound, or functionalised straight or branched alkane, alkene, alkyne or aromatic compound wherein functionalisation could be amide or ester or ether, heterocyclic or homocyclic group or carbon chains containing one or more heteroatoms such as N, S, O covalently bonded to FG and FG’ .

The compound as claimed in Claim 14, wherein FG of each molecule could be same or different.

The compound as claimed in Claim 14, wherein FG’ of each molecule could be same or different.

The spacer group R in Claim 14 contains two or more substituents selected from the group consisting of a halogen, cyano, alkoxy, hydroxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl.

The spacer Group R in Claim 14 contains a carbon chain length 1 to 30 , more preferably 2 to 15, and most preferably 2 to 10.

The compound as claimed in Claim 14, wherein FG of both the molecules is selected from Michael acceptor, or heteroatomic group, or electrophilic group or electrophilic moiety containing a leaving group, and FG’ of both the molecules is amine which further are linked by adding a third molecule that is a bis-isocyanate or dialdehyde such as orthopthalaldehyde, alkyl dialdehyde, or glyoxal.

The compound as claimed in Claim 14, wherein FG of both the molecules is selected from Michael acceptor, or heteroatomic group, or electrophilic group or electrophilic moiety containing a leaving group, and FG’ of one of the molecules is a quaternary amine and FG’s of the other molecule is a carboxylate ion and there is an electrostatic interaction between the two FG’s.

The compound as claimed in Claim 14, wherein FG of both the molecules is selected from Michael acceptor, or heteroatomic group, or electrophilic group or electrophilic moiety containing a leaving group, and FG’ of one of the molecules is an alkyne and FG’s of the other molecule is an azide, and both the FG’s click to form a triazole.

The alkene moiety as a Michael acceptor on the active molecule could be located other than at the ends of the molecule and on its ends carry thiol groups whereby the thiol groups on the active molecule interact with thiols on either side of the hair keratin forming disulfide bonds or one thiol on the active molecule can form a disulfide bond with one thiol on one side of hair keratin and the alkene site on the active molecule involves in Michael addition with another thiol on the other side of the hair keratin.

The compound as claimed in Claim 22 is Dithio maleate.

A composition for permanent straightening of hair comprising:
a reducing agent;
an active agent of Structure I
FG- R-FG'
(Structure I),
wherein, FG, FG’ and R have the meanings as defined above, and
in a cosmetically acceptable excipient.

The composition as claimed in Claim 24, wherein the reducing agent is selected from and not limited to thioglycolic acid and its derivative salts and esters, thioglycerol, thiolactic acid and its derivative salts and esters, cysteine and its derivatives, cysteamine, inorganic Sulphites, sodium metabisulfite, other inorganic bisulphites, which break the disulfide bonds into thiols.

The composition as claimed in Claim 24, wherein the cosmetically acceptable excipient is a surfactant, an emulsifier, a thickener, a polyol, a humectant, pH adjusting agent, a cationic conditioner, an emollient, an oil, water, a preservative and fragrance.

The composition as claimed in Claim 24, wherein the concentration of the reducing agent in the composition is preferably 0.1 wt% to 20 wt%, more preferably 0.5 wt% to 15 wt%, and most preferably 2 wt% to 11 wt%.

The composition as claimed in Claim 24, wherein the Concentration of the active agent of Structure 1 is preferably 0.1 wt% to 20 wt%, more preferably 0.5 wt% to 15 wt%, and most preferably 1 wt% to 10 wt%.

The composition as claimed in Claim 24 wherein, the pH of the composition is preferably 6 to 12, more preferably 7.5 to 10, and most preferably 8 to 9.5.

The composition as claimed in Claim 24 wherein, the viscosity of the composition is preferably 100,000 cP to 900,000 cP, more preferably 250,000 cP to 700,000 cP and most preferably 350,000 to 500,000 cP.

A one-step process for permanent straightening of hair comprising applying the composition as claimed in Claim 24, wherein the process comprises of:
applying the single composition containing the reducing agent, the active agent of Claim 24 as a thick product cladding on stretched hair;
leaving the product of step (a) for 30 – 60mins, and
rinsing of the hair,
Optionally flat ironing or hot blow drying

A kit for permanent straightening of hair comprising:
a reducing agent composition in dispensable format;
a composition containing active agent of Structure I in a dispensable format
FG- R-FG'
(Structure I),
wherein, FG, FG’ and R have the meanings as defined above, and
Both compositions are formulated in a cosmetically active excipient.

The concentration of the reducing agent in the composition of Claim 32 is preferably 0.1 wt% to 40 wt%, more preferably 0.5 wt% to 30 wt%, and most preferably 2 wt% to 22 wt%.

The Concentration of the active agent of Structure 1 in the composition of Claim 32 is preferably 0.1 wt% to 30 wt%, more preferably 0.5 wt% to 20 wt%, and most preferably 1 wt% to 15 wt%.

The pH of each of the compositions in Claim 32 is preferably 6 to 12, more preferably 7.5 to 10, and most preferably 8 to 9.5.

The viscosity of each of the compositions in Claim 32 is preferably 100,000 cP to 900,000 cP, more preferably 250,000 cP to 700,000 cP and most preferably 350,000 to 500,000 cP.

A one-step process for permanent straightening of hair, wherein the process comprises of:
Mixing the composition containing the reducing agent and the composition containing the active agent of Structure 1 as in Claim 32 and applying this mixed thick product cladding on stretched hair;
leaving the product of step (a) for 30 – 60mins, and
rinsing of the hair,
Optionally flat ironing or hot blow drying

A two-step process for permanent straightening of hair comprising applying the compositions as claimed in Claim 32, wherein the process comprises of:
applying a composition containing the reducing agent;
applying the composition containing the active agent of Structure 1, without rinsing of hair;
leaving the composition for 30 – 60mins, and
rinsing the hair,
Optionally flat ironing or hot blow drying

A two-step process for permanent straightening of hair comprising applying the compositions as claimed in Claim 32, wherein the process comprises of:
applying a composition containing the reducing agent first on the hair;
Leave the composition for 30-60 minutes and the rinse the hair;
Hot Flat iron the hair;
Apply the composition containing the active agent of Structure 1;
Leave the composition for 30 – 60mins, and
Rinse the hair.

A two-step process for permanent straightening of hair comprising applying the compositions as claimed in Claim 32, wherein the process comprises of:
applying a composition containing the reducing agent first on the hair;
Leave the composition for 30-60 minutes and the rinse the hair;
Apply the composition containing the active agent of Structure 1 and hot Flat iron the hair;
Leave the composition containing active agent of Structure 1 for 30 – 60 mins, and
Rinse the hair.

The kit as claimed in Claim 32, wherein the kit comprises a single pack containing all the compositions.

The kit as claimed in Claim 32, wherein the kit comprises
a packet A, containing the reducing agent and cosmetically acceptable excipients, and
a packet B, containing the active agent and cosmetically acceptable excipients.

The kit as claimed in Claim 32, wherein the contents of packet A and packet B are applied simultaneously or sequentially.