Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
  • A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
• • A—HUMAN NECESSITIES
  • A45—HAND OR TRAVELLING ARTICLES
  • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
  • A45D19/00—Devices for washing the hair or the scalp; Similar devices for colouring the hair
  • A45D19/0041—Processes for treating the hair of the scalp
  • A45D19/0066—Coloring or bleaching
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
  • A61K8/29—Titanium; Compounds thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/37—Esters of carboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/55—Phosphorus compounds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
  • A61K8/8117—Homopolymers or copolymers of aromatic olefines, e.g. polystyrene; Compositions of derivatives of such polymers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/002—Preparations for repairing the hair, e.g. hair cure
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/42—Colour properties
  • A61K2800/43—Pigments; Dyes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/42—Colour properties
  • A61K2800/43—Pigments; Dyes
  • A61K2800/434—Luminescent, Fluorescent; Optical brighteners; Photosensitizers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/42—Colour properties
  • A61K2800/43—Pigments; Dyes
  • A61K2800/438—Thermochromatic; Photochromic; Phototropic
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/58—Metal complex; Coordination compounds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
  • A61K2800/81—Preparation or application process involves irradiation
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
  • A61K2800/95—Involves in-situ formation or cross-linking of polymers

Definitions

• the present invention pertains to the cosmetic sector and refers to a method for the treatment and/or prevention of damaged keratin, more particularly in hair, skin and/or nails.
• Keratin is a fibrous structural protein, making up hair, nails and the outer layer of human skin. Keratin monomers assemble to form intermediate filaments and have a structure exhibiting a central 310 circa residue domain with four segments in alpha-helical conformation that are separated by three short linker segments in beta-turn conformation. The keratin molecules supercoil to form a stable, left-handed superhelical motif to multimerise, forming filaments consisting of multiple copies of the keratin monomer.
• Keratin contains many cysteine residues, which are rich in sulphur-containing functional groups, namely thiol groups (-SH) that form covalent bonds with other thiol groups in sulphur-containing functional groups on adjacent filaments. These strong crosslinks, which involve two sulphur atoms (S-S) are known as the disulphide bonds.
• Human hair is 14% cysteine. Depending on the frequency of such disulphide bonds and their distribution on the hair, they contribute to the bending of hair, and hence to its shape, as well as to its texture. These covalent bonds resist in the presence of water and as a result wet hair resumes its original shape when dried.
• Hair is a filamentous biomaterial, 20-180 pm in width, consisting mainly of keratin.
• the structure of a human hair shaft consists of the medulla at the centre of the hair, surrounded by the cortex, which contains keratins (40-60 kDa) and lipids.
• the cortex is surrounded by the cuticle, the outermost layer made of dead cells in a scale-like formation, that protects the hair.
• the cuticle In healthy-looking hair, the cuticle has a smooth and glossy appearance. This is because the cuticle layer is tightly closed on the hair shaft (see Fig. 2b) .
• the surface of the hair is covered in a covalently bound 18-methyl eicosanoic acid.
• the keratin-containing cortex makes up most of the hair. It consist of loosely packed spindle-shaped cortical cells filled with keratin filaments orientated parallel to the length of the hair and an amorphous matrix of high sulphur proteins.
• the cuticle may be damaged (or "weathered") by mechanical forces, like the friction involved in hair brushing, or chemically, for example by oxidation, typical of bleaching procedures, or permanent styling. Excessive sunlight and heat also cause damage. Damaged hair usually exhibits an open cuticle, where the cuticle lifts from the hair shaft and can develop cracks and peel off (see Fig. 2a) .
• Damaged hair suffers from a decrease in lipid content, affecting its hydrophobicity, and is more porous than healthy looking hair. Damaged hair is also weak, and prone to premature fracturing, longitudinal splitting (i.e. split ends), separation of hair cortex, loss of strength and loss of gloss. This damage ultimately leads to cleaving of the cysteine di sulphide bonds leading to the exposure of the free thiols .
• Hair conditioners have been devised to counteract damage to hair and improve hair gloss. Their main action is in re-establishing the hydrophobicity of the hair shaft and eliminating negative charges on the hair fibre (responsible for static flyaway hair), by providing an oily coating on the cuticle.
• Conditioners normally contain polymers (typically poly-quaternium polymers), oils, waxes, hydrolysed aminoacids and/or cationic molecules.
• conditioners can also make the hair too greasy and prone to attract dirt.
• any beneficial effect of the conditioner is only temporary, as the oily coating is washed off by surfactants with each shampoo.
• the technical problem underlying the present invention is thus that of making available a method, as well as a composition, for the treatment and/or prevention of damaged keratin, in particular in hair, skin and/or nails, more particularly in hair, even more particularly in human scalp hair, that has a long lasting effect, for example an effect on hair lasting at least six months.
• Another technical problem underlying the present invention is that of making available such a method and composition that do not leave undesired residues on the hair shaft, that can negatively affect its gloss and its silky appearance.
• Another technical problem underlying the present invention is that of making available such a method and composition that also further improve the overall appearance of the hair, for example by improving moisture, thus preventing hair dryness, and by increasing hair volume.
• Another technical problem underlying the present invention is that of making available such a method and composition that also help to protect and repair the hair from damage of a chemical or physical origin, such as for example from coloring, bleaching, straightening or styling techniques, thereby also facilitating the use of such techniques.
• Another technical problem underlying the present invention is that of making available such a method and composition that can be easily incorporated into existing hair-colouring/dyeing and hairstyling techniques, both professionally (i.e. in hair saloons) and at home, as well as into hair care products, such as for example conditioners, hair dyeing/colouring products, and hair sprays) .
• keratin-containing tissue what is meant here is a body tissue that typically features the presence of keratin filaments with disulphide bonds, such as for example human or animal hair, human or animal skin and nails .
• the keratin-containing tissue is chosen from human or animal hair, human or animal skin and/or (human) nails, more preferably human or animal hair, even more preferably human scalp hair.
• hair refers to one or more than one strand of hair.
• the cosmetic composition is a fluid composition, more preferably liquid.
• the cosmetic composition is in the form of a suspension or an emulsion, more preferably a suspension.
• the cosmetic composition can, for example, be in the form of a liquid, a lotion, a milk, a mousse, a spray, a gel, a cream, a shampoo or a conditioner.
• the cosmetic composition is applied through a squeeze bottle nozzle or by spraying, or by any other method known in the field, according to convenience .
• light reactive functional group what is meant here is a functional group that can be activated by light having a wavelength comprised between 10 nm and 100 pm, more preferably comprised between 300 nm and 1400 nm, even more preferably comprised between 360 nm and 800 nm, in the presence of a suitable photoinitiator, to form reactive intermediates capable of forming covalent bonds with the target sites, namely free thiols (also referred to as thiol groups) .
• the word “light” is used to mean “electromagnetic radiation”. Throughout the specification, the expression “electromagnetic radiation” and the word “light” are also referred to as “radiation” .
• UV radiation or light
• visible radiation or light
• NIR radiation or light
• the light reactive functional groups are chosen from acrylates, methacrylates, vinyl benzene, alkynes, and combinations thereof, more preferably alkynes.
• the molecules carrying at least one light reactive functional group wherein the functional group is acrylate, methacrylate or vinyl benzene, carry at least two said light reactive functional groups.
• reactive molecules will also be used to refer to “molecules carrying at least one light reactive functional group”. Similarly, “reactive molecule” will also be used to refer to a "molecule carrying at least one light reactive functional group”.
• the reactive molecules have a degree of substitution greater than 5%, more preferably greater than 20%, even more preferably greater than 30%, even more preferably greater than 40%, even more preferably greater than 50%, most preferably greater than 55% .
• the degree of substitution can be modulated based on the molar ratio between the starting molecule and the substituting groups.
• the starting molecule and the substituting groups are respectively gelatin and methacrylic anyhride (MAA) , in the preparation of methacrylate-functionalised gelatin (see Example 1) .
• the degree of substitution can be determined by any method known in the art, such as for example NMR (Nichol., J.W. et al . (2010) Biomaterials, 31 (21) 5536-5544); the Trinitrobenzoic acid assay (Yoon, H.J. et al . (2016) PLoS ONE 11(10) 1- 18); or the Habeeb method (Habeeb, AF . (1966) Anal. Biochem, 14, 328-336); preferably NMR.
• a sample containing functionalised molecules is dissolved in deuterated solvents, for example D2O (Deuterated) or dDMSO (Deuterated Dimethyl Sulfoxide), and analysed by 1 H NMR spectroscopy using, for example, a 300MHz Varian Spectrometer (Varian Inc, Palo Alto, California, US) . Comparison of the results with a non-functionalised sample allows to determine the percentage number of the total potential functional groups that have been functionalised.
• deuterated solvents for example D2O (Deuterated) or dDMSO (Deuterated Dimethyl Sulfoxide)
• 1 H NMR spectroscopy using, for example, a 300MHz Varian Spectrometer (Varian Inc, Palo Alto, California, US) . Comparison of the results with a non-functionalised sample allows to determine the percentage number of the total potential functional groups that have been functionalised.
• the reactive molecules are obtained from the functionalisation of the backbone, side chain(s) and/or terminus/ (i) of the starting molecules.
• the reactive molecules wherein the light reactive functional group is alkyne are obtained from the functionalisation of the backbone, side chain(s) and/or terminus/-i of the starting molecules, more preferably the side chain (s) .
• the reactive molecules wherein the light reactive functional group is acrylate, methacrylate or vinyl benzene are obtained from the functionalisation of the side chain (s) of the starting molecules .
• the light reactive functional group(s) is/are covalently bound.
• the reactive molecules are compatible with aqueous or solvent cosmetic delivery systems, more preferably aqueous cosmetic delivery systems.
• the reactive molecules of the present invention are chosen based on their chemical compatibility with the keratin-containing tissue, more preferably human or animal hair, even more preferably human scalp hair, most preferably also on their suitability for being rinsed off the keratin-containing tissue, typically with water, when in excess.
• the reactive molecules are obtained from the functionalisation of aminoacids, saccharides and/or fatty acids, and/or residues thereof.
• the starting molecules are preferably aminoacids, saccharides and/or fatty acids, and/or residues thereof.
• the aminoacids, saccharides and/or fatty acids, and/or residues thereof are natural aminoacids, saccharides and/or fatty acids, and/or residues thereof.
• the expression "natural aminoacids, saccharides and/or fatty acids, and/or residues thereof" is used herein to refer to aminoacids, saccharides and/or fatty acids, and/or residues thereof, that are found in nature.
• the aminoacid can be a free aminoacid or can be bound via a peptide bond to other aminoacids in the form of branched or linear polypeptide chains, or proteins .
• the branched or linear polypeptide chain has a chain length comprised between 2 and 3000 aminoacid residues.
• the proteins have a molecular weight comprised between 0. lkDa and 800000kDa, more preferably comprised between lkDa and lOOOOOkDa, even more preferably comprised between 2kDa and 300kDa.
• proteins are chosen from collagen, gelatin, keratin, and albumin.
• proteins and aminoacids are chosen from plant proteins and aminoacids, that is, proteins and aminoacids from a plant source.
• the plant proteins are chosen from hydrolysed soy protein, hydrolysed wheat protein, hydrolysed rice protein, hydrolysed quinoa protein, hydrolysed barley protein, hydrolysed vegetable protein and mixtures thereof.
• the plant aminoacids are a mixture of aminoacids, the mixture mimicking the characteristics of keratin, such as for example solutions containing wheat and soy aminoacids (for example that under the trade name of Fision KeraVegl8 by TRI-K Industries Inc, India) .
• reactive molecules obtained from the functionalisation of proteins are gelatin methacryloyl , gelatin acrylate, gelatin methacrylamide/methacrylate, gelatin vinyl benzene, and glycidyl methacrylate- modified gelatin.
• Functionalisation of proteins and/or residues therof can be carried out according to known methods in the field.
• functionalisation of proteins in their side chains with acrylates or methacrylates can be carried out according to known methods in the field, such as for example Nichol, JW. et al . (2010, Nichol, JW. et al . (2010) Biomaterials, 31(21) :5536- 5544); Gaudet ID. and Shreiber, DI . (2012, Gaudet ID. and Shreiber, DI . (2012) Biointerphases, 2012, 7:25); Brinkman, WT . et al . (2003, Brinkman, WT . et al .
• the saccharides are in a form chosen from monosaccharides, disaccharides, branched or linear oligosaccharides, and branched or linear polysaccharides .
• the polysaccharides have a molecular weight comprised between 0. lkDa and 800000kDa, more preferably comprised between lkDa and 300000kDa, even more preferably comprised between 2kDa and 300kDa.
• the polysaccharides are chosen from, hyaluronic acid, alginates, dextrose, cellulose, and derivatives thereof.
• the polysaccharide can be a salt, preferably a hyaluronic acid salt.
• the monosaccharides are chosen from dextrose, glucose and fructose.
• Functionalisation of saccharides and/ore residues thereof can be carried out according to known methods in the field.
• functionalisation of saccharides with acrylates or methacrylates, or alkynes can be carried out according to known methods in the field, such as Smeds KA. et al . (2001, Smeds KA. et al.
• the fatty acids are free fatty acids or bound to form a lipid, for example esterified with glycerol to form glycerides or phospholipids, or bound to form other lipids.
• the fatty acids can be in the form of saturated or unsaturated fatty acids.
• fatty acids have a number of carbon atoms comprised between 2 and 100 more preferably comprised between 5 and 70, even more preferably comprised between 7 and 25.
• the fatty acids are chosen from stearic acid, oleic acid, palmitic acid, lauric acid, linoleic acid.
• Functionalisation of fatty acids and/or residues thereof can be carried out according to known methods in the field.
• functionalisation of fatty acids with acrylates, methacrylates or alkynes can be carried out according to known methods in the field, such as for example Adekunle, K. et al. (2009,
• the reactive molecules are obtained from the functionalisation of synthetic polymers, more preferably synthetic polymers carrying at least one alkyne functional group.
• the starting molecules are preferably synthetic polymers, more preferably synthetic polymers carrying at least one alkyne functional group.
• the synthetic polymers are chosen among those suitable for cosmetic uses, and comprise polyvinyl pyrrolidone homo and copolymers, polyvinyl acetate, polyacrylates, polymethacrylates, polyamides, polyvinylamides , polyurethanes, and silicones.
• the synthetic polymers are functionalised with alkyne functional groups.
• reactive molecules obtained from the functionalisation of synthetic polymers with alkynes are functionalised aminoacids or peptides, such as for example poly-L-lysine hydrobromide graft alkyne (with functionalisation either at the side chain or at the terminus) and L-homopropargylglycine .
• Examples of reactive molecules obtained from the functionalisation of synthetic polymers with alkynes at the backbone are benzenesulfonamides , oxazolidinone and pyrrolidinones , such as 4-methyl-N- ( 2-phenylethynyl ) -N- (phenylmethyl ) - benzenesulfonamide, 3- ( 1-octyn-l-yl ) -2-oxazolidinone, 3- ( 2-phenylethynyl ) -2-oxazolidinone, 1- ( 2- phenylethynyl ) -2-pyrrolidinone, (R) -4-Phenyl-3- ( 2- phenylethynyl ) oxazolidin-2-one, and TMS-N-ethynyl-N, 4- dimethylbenzenesulfonamide >95%.
• alkyne-functionalised synthetic polymers are alpha-methyl-poly ( 2-ethyl-2-oxazoline ) - omega-alkyne (Me-PEtOx-alkyne) , ( S ) - ( - ) -2-Az ido-6 - ( Boc- amino ) hexanoic acid (dicyclohexylammonium) salt, (S)-2- Azido-3- ( 4-tert-butoxyphenyl ) propionic acid cyclohexylammonium salt, ( S ) -5-Azido-2- (Fmoc- amino ) pentanoic acid, L-Azidohomoalanine hydrochloride, (S)-2 Az ido-3- ( 3-indolyl ) propionic acid cyclohexylammonium salt, ( S ) -2-Azido-3-methylbutyric acid cyclohexylam
• the cosmetic composition of the present invention can comprise a mixture of any of the reactive molecules described above, namely reactive molecules obtained from the functionalisation of: aminoacids and/or residues thereof; saccharides and/or residues thereof; fatty acids and/or residues thereof; and synthetic polymers, in any combination thereof.
• the cosmetic composition may comprise reactive molecules obtained from the functionalisation of aminoacids and/or residues thereof and reactive molecules obtained from the functionalisation of synthetic polymers; or it may comprise reactive molecules obtained from the functionalisation of aminoacids and/or residues thereof and reactive molecules obtained from the functionalisation of saccharides and/or residues thereof; or it may comprise reactive molecules obtained from the functionalisation of aminoacids and/or residues thereof, reactive molecules obtained from the functionalisation of saccharides and/or residues thereof, and reactive molecules obtained from the functionalisation of synthetic polymers; or any other combination of the above mentioned reactive molecules.
• the reactive molecules of the present invention can be synthesized according to methods known in the field. Also, the reactive molecules of the present invention may be commercially available.
• the damaged keratin in a keratin-containing tissue comprises at least two free thiol groups, more preferably at least 2 pmoles of free thiol groups per gram of keratin-containing tissue, most preferably from 2 to 1000 pmoles of free thiol groups per gram of keratin-containing tissue.
• the keratin-containing tissue is human or animal hair, even more preferably human scalp hair, and it comprises at least 2 pmoles, more preferably at least 20 pmoles, even more preferably at least 200 pmoles, most preferably from 200 pmoles to 1000 pmoles, of free thiol groups per gram of keratin-containing tissue .
• the determination of the concentration of the number of thiol groups per gram of keratin-containing tissue can be carried our according to any method known in the art, for example according to the method described in Xu et al. (2017), Green and sustainable technology for high-efficiency and low-damage manipulation of densely crosslinked proteins, ACS Omega, 2, 1760-1768, under the paragraph "Titration of Sulfhydryl Groups, Carboxyl Groups, and Amine Groups" under the Materials and Methods section.
• the damaged keratin-containing tissue is human or animal hair, more preferably human scalp hair, and the hair exhibits one or more of the following features: a dry texture, a dull appearance, poor gloss, weakness, fracturing, split ends, and reduced surface lipids.
• the damaged keratin-containing tissue is human or animal skin, and the skin exhibits one or more of the following features: dryness, itchiness, wrinkles, and reduced surface lipids.
• the damaged keratin-containing tissue is (human) nails, and the nails exhibit one or more of the following features: brittleness, porosity, softness, presence of white lines, and reduced surface lipids .
• the reactive molecules are present in a concentration, in weight percent based on the volume of the composition, of at least 0.01%, more preferably comprised between 0.05% and 20%, even more preferably comprised between 0.1 and 15%, most preferably between 0.5 and 10%.
• the keratin-containing tissue is chosen from human or animal hair; human or animal skin; and/or (human) nails, more preferably human or animal hair, even more preferably human scalp hair, and the keratin comprises at least two free thiol groups.
• the keratin is damaged keratin.
• step a) of the first method the keratin is damaged keratin.
• the animal hair and/or skin is mammal hair and/or skin, more preferably the hair and/or skin of pets, such as for example cats, dogs, rabbits and horses .
• the keratin-containing tissue is human or animal hair, more preferably human scalp hair, and it is damp. Damp hair, in fact, allows better penetration of the reactive molecules, compared to dry hair.
• a photoinitiator is a molecule that converts absorbed ultraviolet, visible or near infrared light into chemical energy in the form of initiating species (i.e. the photoinitiator is activated), for example free radicals or cations.
• the photoinitiator is activated (or excited) at a wavelength comprised between 10 nm and 100 pm, more preferably between 300 and 1400 nm, even more preferably between 360 nm and 800 nm, most preferably between 360 nm and 400 nm.
• the photoinitiator is a radical photoinitiator .
• the at least one photoinitiator can be a one- component, two-component or multi-component system, preferably a one-component system.
• the photoinitiator is water-soluble.
• the photoinitiator is activated (or excited) upon UV radiation and is preferably chosen from alpha hydroxyketones or derivatives thereof, such as for example benzoin ethers, benzyl ketals, alpha-dialkoxy- alkyl-phenones , alpha-hydroxy-alkyl-phenones , alpha- amino-alkyl-phenones , acyl-phosphine oxides, benzo- phenones and thio-xanthones .
• alpha hydroxyketones or derivatives thereof such as for example benzoin ethers, benzyl ketals, alpha-dialkoxy- alkyl-phenones , alpha-hydroxy-alkyl-phenones , alpha- amino-alkyl-phenones , acyl-phosphine oxides, benzo- phenones and thio-xanthones .
• photoinitiators in the UV light spectrum are bis ( 2 , 4 , 6-trimethylbenzoyl ) - phenylphosphineoxide (Irgacure ® 819), bis ( . eta .5-2 , 4- cyclopentadien-l-yl ) -bis ( 2 , 6-difluoro-3- ( lH-pyrrol-1- yl ) -phenyl ) titanium (Irgacure ® 784), 1— [4— (2— Hydroxyethoxy ) -phenyl] -2-hydroxy-2-methyl-l-propane-l- one (Irgacure ® 2959) .
• the photoinitiator is activated (or excited) upon visible light.
• suitable photoinitiators in the visible light spectrum are 2', 4', 5', 7' - Tetrabromofluorescein disodium salt
• the photoinitiator is activated (or excited) upon near IR radiation and is preferably chosen from cyclic benzylidene ketone-based initiators.
• the photoinitiator is present in the cosmetic composition in a concentration, in weight percent based on the total volume of the cosmetic composition, comprised between 0,01% and 10% more preferably comprised between 0,1% and 5%, even more preferably comprised between 0.5% and 3%.
• the cosmetic composition has a pH comprised between 4 and 9 more preferably comprised between 6 and 7,4.
• the cosmetic composition further comprises one or more eccipients chosen from water, phosphate buffer saline (PBS) and oil, preferably water .
• PBS phosphate buffer saline
• oil preferably water
• the water is ultrapure water, for example Milli Q® water (Millipore Corporation,
• the cosmetic composition further comprises one or more ingredients, more preferably chosen from moisturisers , acidity regulators, oils, surfactants, lubricants, sequestrants , antistatic agents, antimicrobial agents, preservatives, emulsifiers, thickeners, emolients and sunscreen and/or fragrances .
• moisturisers acidity regulators, oils, surfactants, lubricants, sequestrants , antistatic agents, antimicrobial agents, preservatives, emulsifiers, thickeners, emolients and sunscreen and/or fragrances .
• the cosmetic composition further comprises at least one colouring agent, preferably chosen from a pigment, a dye and a combination thereof.
• the colouring agent is present in the cosmetic composition in a concentration, in weight percent based on the volume of the cosmetic composition, comprised between 0.0001 and 1%, more preferably between 0.001 and 0.1%
• the colouring agent is capable of emitting light when exposed to radiation having a wavelength comprised between 10 nm and 100 pm, more preferably between 300 nm and 1400 nm, even more preferably between 360 nm and 800 nm, most preferably between 360 and 400 nm.
• the colouring agent is a fluorescent dye or a non-fluorescent dye, more preferably a fluorescent dye.
• Fluorescein is an example of a fluorescent dye that can be used in the present invention.
• the colouring agent is physically or covalently bound to the molecules, more preferably physically bound, for example through Van der Waal's forces or hydrogen bonds.
• step a) the cosmetic composition is applied evenly on the keratin-containing tissue.
• the keratin-containing tissue is human or animal hair, more preferably human scalp hair, and the cosmetic composition is applied with the aid of a brush or comb.
• a colouring agent in particular a fluorescent one
• a colouring agent enables the user to determine, for example by exposing the hair to UV radiation, whether the cosmetic composition is evenly applied on the hair. It is known that mechanical stresses, such as excessive brushing of hair, especially when wet, leads to hair damage. Being able to determine when the composition is evenly applied thus has the dual advantage of optimising the uniformity of the result while at the same time avoiding any unnecessary handling of the hair once the composition is evenly spread.
• the expression "leaving to process” of step b) means that the cosmetic composition is left in contact with the keratin- containing tissue.
• step b) the composition is left to process for a processing time of at least 5 minutes, more preferably for a time comprised between 7 and 40 minutes, even more preferably for a time comprised between 10 and 30 minutes, most preferably for a time comprised between 15 and 20 minutes.
• the temperature of the environment surrounding the keratin-containing tissue is between 4 and 35 °C, more preferably between 10 and 30 °C, most preferably between 20 and 25 °C.
• the keratin-containing tissue is exposed to a light having a wavelength comprised between 360 and 800 nm, more preferably comprised between 360 and 400 nm (UV light) .
• the keratin-containing tissue is exposed to the light for at least 5 minutes, more preferably a time comprised between 7 and 40 minutes, even more preferably for a time comprised between 10 and 30 minutes, most preferably for a time comprised between 15 and 20 minutes.
• step b) the keratin-containing tissue is exposed to the light for the duration of the processing time.
• the keratin-containing tissue can be exposed to light using any known suitable light-emitting device known in the field, such as for example radiation lamps or radiation-emitting combs.
• the keratin-containing tissue is human or animal hair, more preferably human scalp hair, and the hair is combed or brushed, more preferably using a light-emitting comb or brush, even more preferably a UV-A comb or a laser comb.
• the light-emitting comb or brush emits light having a wavelength comprised between 360 nm and 400 nm, more preferably comprised between 360 and 380, even more preferably 370 nm.
• the light-emitting comb or brush emits both ultraviolet light and NIR light, preferably by switching between the ultraviolet light and NIR light during use.
• step b) the hair is combed or brushed for the duration of the processing time.
• step b) is followed by step c) of rinsing the keratin-containing tissue, preferably the human or animal hair, more preferably human scalp hair.
• step c) of rinsing is carried out, with water, until complete removal of excess residues from the keratin-containing tissue, preferably unreacted reactive molecules.
• damaged keratin is characterised by the fact that disulphur (or rather, disulphide) bridges on and between keratin filaments are broken, thus exposing free thiols.
• the present invention solves the technical problem by providing functional groups that covalently link to the free thiols to establish crosslinks between them. This, in turn, re-establishes the smooth and healthy appearance typical of healthy-looking keratin- containing tissue, such as human or animal hair, nails and human or animal skin. Provided that the overall number of reactive molecules applied are in sufficient amount, all free thiols can be crosslinked in one application of the composition.
• the reactive molecules of the present invention when activated by the photoinitiator, enable the functional groups, namely acrylates, methacrylates, vinyl benzene, and/or alkynes, to covalently link to the free thiols on the damaged hair, thus forming crosslinks.
• This reaction is a radical-mediated thiol- ene (in the case of acrylates, methacrylates and vinyl benzene) or thiol-yne (in the case of alkyne) coupling.
• An overview of the reactions involved in the crosslinking of alkenes and alkynes is provided in Konuray et al. (2018, Konuray et al. (2016) Polymers, 10, 178) .
• one alkene can crosslink with one free thiol.
• a crosslink i.e. bridge the broken disulphide
• at least two such functional groups are required on the same reactive molecule.
• one such functional group on the reactive molecule suffices to bind to two thiols and bridge them.
• Figure 1 shows schematically the mechanism by which the method of the invention repairs damaged keratin, for example on hair.
• Figure la the schematic drawing on the left hand side of the arrow represents the keratin filaments of healthy hair, which exhibits naturally occurring disulphide bonds (or bridges) . Following environmental or chemical stresses (represented by the arrow), the disulphide bonds are cleaved, giving rise to free thiols, as schematically represented on the right hand side of the arrow of figure la.
• the method of the present invention provides reactive molecules that, in the presence of light, bind to the free thiols, thus establishing crosslinks between adjacent free thiols.
• This is shown in Figure lb, with particular reference to a reactive molecule carrying at least two acrylate or methacrylate functional groups.
• Figure lc shows the crosslinking between adjacent free thiols according to the method of the invention in the case of a reactive molecule carrying at least one alkyne functional group.
• the effect of the method is permanent, having a duration of at least 30 days, more preferably at least 6 months, even more preferably at least one year, most preferably at least 18 months.
• the above- described method of the present invention can be repeated once or more on the previously treated keratin-containing tissue.
• steps a) to c) of the method of the present invention are repeated.
• the cosmetic composition is applied on a keratin-containing tissue, more preferably human or animal hair, even more preferably human scalp hair, comprising keratin filaments covalently bound to said reactive molecules.
• the keratin-containing tissue more preferably human or animal hair, even more preferably human scalp hair, comprising keratin filaments covalently bound to the reactive molecules has previously undergone the method for the treatment and/or prevention of damaged hair of the present invention (i.e. first method) .
• the cosmetic composition can be formulated to be a hair conditioning composition. This can be achieved for example with the addition of hair conditioning agents to the cosmetic composition of the invention, or by adding the cosmetic composition of the invention to an existing hair conditioning composition.
• conditioning agent a cosmetic ingredient which is used in conditioning compositions to soften, smooth or change the sheen of the hair.
• Suitable conditioning agents include but are not limited to polycationic polymers, for example polyquaternium polymers or silicone quaternium-8 ; alcohols, for example oleyl alcohol, stearyl alcohol, cetyl alcohol, panthenol; oils, such as meadowfoam seed oil, mango seed oil, grape seed oil, jojoba seed oil, sweet almond oil,; polyols; and other ingredients such as hydrolysed wheat and/or soy protien amino acids, rice bran wax, hydroxyethyl behenamidopropyl dimonium chloride, aloe leaf extract, aloe barbadensis leaf juice, phytantriol, retinyl palmitate, behentrimonium methosulphate, cyclopentasiloxane, quaternium-91 , stearamidopropyl dimethylamine that improve the
• a “conditioning composition” is a composition containing an effective amount of one or more conditioning agents, which is applied to hair to soften, smooth or change the sheen of the hair.
• the conditioning composition, or conditioner can be of any of the known types, namely pack, leave-in, ordinary and hold.
• step (b) is carried out for 5 to 10 minutes, more preferably 8-12 minutes.
• the keratin-containing tissue is exposed to the light for 5-15 minutes, more preferably 8-12 minutes .
• step c) is preceded by a step c') of leaving the keratin-containing tissue, more preferably human or animal hair, even more preferably human scalp hair, to process without exposure to radiation for at least 5 minutes, more preferably 10 to 45 minutes, even more preferably 20 to 40 minutes.
• the first method of the present invention is repeated after a time comprised between 1 week and 6 months, more preferably between 1 and 3 months .
• the second method of the present invention can be carried out at a frequency of 1-20 times a month, more preferably 1-4 times a week, most preferably 1-2 times a week, more preferably for 4-8 weeks.
• the method i.e. carry out the second method of the invention
• One repetition is usually sufficient to maintain the desired results.
• the second method can be repeated more than once, and at a higher frequency, depending on the results to be achieved.
• the keratin- containing tissue is human or animal hair, even more preferably human scalp hair, and it is exposed to light using the radiation-emitting comb or radiation-emitting brush .
• steps a) to c) of the first method of the present invention are repeated and the cosmetic composition has a concentration of reactive molecules that is lower than the concentration of the cosmetic composition in the first method and/or the second method .
• the third method of the present invention can be repeated once or twice a week, more preferably for 1-8 weeks .
• the keratin-containing tissue is exposed to light using a radiation-emitting comb or is exposed to visible light .
• the third method in fact, is particularly suited for being performed at home.
• the third method of the invention follows the first method and/or the second method of the invention.
• the cosmetic composition comprises at least one conditioning agent.
• the present invention also refers to said cosmetic composition comprising said reactive molecules and at least one photoinitiator.
• the cosmetic composition is stable for at least six months, preferably at least 12 months, even more preferably, at least 2 years, upon storage at a temperature comprised between 4 and 25 °C.
• stable what is meant is that more than 30% of the molecules are intact and reactive to light in the presence of a suitable photoinitiator.
• the present invention further refers to the use of the cosmetic composition of the present invention on keratin-containing tissue, preferably human or animal hair, human nails and/or human or animal skin, more preferably human or animal hair, even more preferably human scalp hair, comprising at least two free thiol groups for the treatment and/or prevention of damaged keratin .
• the present invention further refers to the use of the cosmetic composition of the present invention on keratin-containing tissue, preferably human or animal hair, human nails and/or human or animal skin, more preferably human or animal hair, even more preferably human scalp hair, comprising at least two free thiol groups for the formation of a crosslink between the at least two free thiol groups (that is, the formation of a disulphide bridge) .
• the crosslink is the result of a covalent bond between the at least one light reactive functional group of the reactive molecules and the free thiols .
• the present invention further refers to the use of the cosmetic composition of the present invention on human or animal hair, even more preferably human scalp hair, comprising at least two free thiol groups, for closing the hair cuticles.
• said keratin-containing tissue is damaged keratin-containing tissue.
• the present invention further refers to the use of the composition of the present invention on keratin- containing tissue, preferably human or animal hair, more preferably human scalp hair, comprising keratin filaments covalently bound to the reactive molecules.
• the keratin-containing tissue preferably human or animal hair, more preferably human scalp hair, comprising keratin filaments covalently bound to the reactive molecules has previously undergone the method for the treatment and/or prevention of damaged hair of the present invention.
• the cosmetic composition of the present invention is used in association with exposure of the keratin-containing tissue to light.
• the cosmetic composition of the present invention is used in association with another cosmetic product, such as for example a hair conditioning composition, a hair dyeing/colouring product or a hair spray, as well as hand creams or body creams .
• another cosmetic product such as for example a hair conditioning composition, a hair dyeing/colouring product or a hair spray, as well as hand creams or body creams .
• the cosmetic composition of the present invention may also be a hair- bleaching, -straightening, -waving, -curling or -colouring formulation.
• the reactive molecules of the cosmetic composition are in fact compatible with other molecules for various hair treatments.
• the present invention also refers to the use of a colouring agent, preferably a fluorescent colouring agent, more preferably covalently bound to the reactive molecules, in the cosmetic composition of the present invention for the visualisation of the evenness of the application of the cosmetic composition of the invention.
• the colouring agent can be detected upon exposure of the keratin-containing tissue to a light having a suitable wavelength.
• the colouring agent as described above can also be used to permanently colour the keratin-containing tissue.
• the method of the present invention provides a number of advantages.
• the major advantage of the method of the present invention is that it has a long lasting effect.
• the covalent bond between the reactive molecules and the free thiols, as well as repairing the damage on the keratin filament, also provides a protective layer against future mechanical and chemical stress.
• Such protective layer can make the keratin-containing tissue look healthier, and in the case of hair it can enhance the volume of the hair, making it look even healthier.
• the protective layer can have a moisturising effect, thus preventing for example dry hair and dry skin.
• the reactive molecules of the invention, as well as any other ingredient in the composition used in the method of the present invention can be chosen to be organic and of natural origin.
• the composition can be environmentally friendly and safe to handle .
• the reactive molecules of the present invention are particularly stable upon storage. This is because the functional groups are covalently bound. This allows long storage times of the composition.
• the method of the present invention is also easy to carry out and does not require expensive equipment.
• the present invention refers to a kit of parts for the treatment and/or prevention of damaged keratin in human or animal hair, preferably human scalp hair, comprising a first and a second formulation of the cosmetic composition comprising reactive molecules of the invention.
• At least one of the first and second formulation can comprise a conditioning agent.
• at least one of the first and second formulation can be added to a conditioning composition.
• the first formulation is a composition suitable for the repetition of the method of the invention on hair that comprises the reactive molecules (i.e. the second method of the present invention) .
• the second formulation has a lower concentration of reactive molecules than the first formulation, and can be used once or twice a week.
• the second formulation is suitable for carrying out the third method of the present invention.
• the first and second formulation may be a bleaching, straightening, waving, curling or coloring formulation .
• the kit may also comprise a third formulation of the cosmetic composition, for use in the method of the invention, wherein the composition has a concentration of reactive molecules higher or the same as the first formulation and is suitable to be applied on damaged hair, preferably that does not comprise the reactive molecules on the keratin filaments thereof.
• the third formulation is thus suitable for carrying out the first method of the present invention.
• the cosmetic composition comprises at least one photoinitiator that is activated in the visible spectrum.
• the cosmetic composition comprises at least one photoinitiator that is activated in the UV spectrum.
• the kit may also comprise a radiation-emitting comb .
• Figure 1 is a schematic representation of keratin filaments of hair.
• Figure la shows the effect of keratin damage on the disulphide bonds between keratin filaments.
• Figure lb shows the effect of the method of the present invention on damaged keratin where the functional groups on the reactive molecules are acrylates or methacrylates.
• Figure lc shows the effect of the method of the present invention on damaged keratin where the functional groups on the reactive molecules are alkynes.
• Figure 2 shows electron microscopic images of DTT damaged hair (2a) and repaired hair following the treatment method of the invention (2b) .
• Figure 3 shows two photographs comparing a volunteer's hair before (3a) and after (3b) treatment with the method of the invention.
• Figure 4 shows a photograph of hair irradiated with UV light following application of the cosmetic composition in the treatment of the invention, wherein the composition contains a fluorescent dye.
• the pH was adjusted to 8.5-9 using 3N Sodium Hydroxide (Sigma) .
• Methacrylic anhydride (MAA, obtained from Sigma-Aldrich (Sweden) was added to the solution, with continuous vigorous stirring, in 3 molar excess with respect to gelatin lysine side groups (i.e. at a ratio of 1:3 of the mole percent of gelatin lysines to methacrylic anhydride) without altering the pH and the temperature to obtain the functionalisation of the gelatin with methacrylic groups on the side chains.
• MAA Methacrylic anhydride
• the mixture was dialysed against water (pH >8-9) for 24 hours using Dialysis Membranes (MWCO 12000-14000 kD) obtained from Spectrum Laboratories, Inc. (CA, US) at room temperature (about
• the reaction product was then freeze-dried.
• the degree of substitution (DS) was determined by NMR.
• Example 1 The method of Example 1 was carried out by replacing methacrylic anhydride with acrylic anhydride (MP Biomedicals, USA) . Analyses by NMR showed more than 55% modification of the gelatin.
• Example 2 Preparation of a composition comprising glycidyl methacrylate-functionalised gelatin .
• the method of Example 1 was carried out by replacing methacrylic anhydride with glycidyl methacrylate ( Sigma-Aldrich, Sweden)) where the pH of the solution was adjusted to 3.5 - 4 using 1M HC1. After this, 6 mL of glycidyl methacrylate was added into the solution dropwise. The reaction was conducted at 50°C for 24 h and the product was purified by dialysis against Milli- Q water (Millipore Corporation, Darmstadt, Germany) with the above-mentioned dialysis membrane at 40 °C for five days. Analyses by NMR showed more than 40% modification of the gelatin.
• Example 1 The method of Example 1 was carried out by replacing methacrylic anhydride with 4- vinyl benzene chloride (VBC) (Sigma-Aldrich, Sweden) solubilised in 0.5M hydrochloric acid and the solution pH was neutralized to pH 7.4-8 before adding VBC in molar excess at a molar ratio of 1:5 with respect to the lysine amines in gelatin (i.e. at a ratio of 1:5 of the mole percent of gelatin lysines to VBC) .
• VBC 4- vinyl benzene chloride
• Example 1 The method of Example 1 was carried out by replacing methacrylic anhydride with propargyl N-hydroxysuccimide ester ( Sigma-Aldrich, Sweden), solubilised in minimal quantity dimethyl sulfoxide (DMSO) (Sigma), in molar excess at a 1:5 molar ratio with respect to the mole percent of lysine amine groups in gelatin (i.e. at a ratio of 1:5 of the mole percent of gelatin lysines to propargyl N-hydroxysuccimide ester), that was added drop-wise at 50-55°C while stirring for 3 hours.
• DMSO dimethyl sulfoxide
• reaction mixture was dialyzed against distilled water (>pH 8) using 12-14kDa cutoff dialysis tubing (Spectrum Laboratories, Inc., CA, US) for 2 days to remove reaction by-products. Analyses by NMR showed a >25-30% modification of the gelatin.
• a 5% (w/v) composition of the product of Example 1 was prepared by dissolving appropriate amounts in distilled water mixed with 1% of photoinitiator Irgacure 2959 ® (supplied by Sigma Aldrich, Sweden) that had been previously dissolved in hot water at 80 °C.
• Preservatives including Sodium benzoate and phenoxyethanol were also added as antimicrobial agents.
• the composition exhibited a shelf life of >12 months.
• DTT dithiotretiol
• Figure 3 shows a comparison of the appearance of the hair before (3a) and after (3b) treatment. It can be seen that after the treatment the hair is shinier, more uniform and not as dry.
• Example 7 After the hair treatment of Example 7, a second treatment according to Example 7 was carried out on the same four volunteers with the difference that the composition applied to the hair was a 1:5 (on a weight to weight basis) mixture of the composition of Example 6 and a conditioning composition free of sulfates, phosphates and parabens and having the following composition: Aqua/Water/Eau, Behentrimonium Chloride, Cetearyl Alcohol, Stearamidopropyl Dimethylamine, PPG-3 Benzyl Ether Myristate, PEG-40 Castor Oil, Glycerin, Cetrimonium Chloride, Hydrolyzed Vegetable Protein PG- Propyl Silanetriol, Argania Spinosa (ARGAN) Kernel Oil, Simmondsia Chinensis (Jojoba) Seed Oil, Persea Gratissima (Avocado) Oil, Keratin Amino Acids, Hydrolyzed Keratin, Sodium PCA, Silk Amino Acids,
• Chloride Disodium EDTA, Fragrance (Parfum) , Phenoxyethanol , Ethylhexylglycerin, Citric Acid, Yellow 5 (Cl 19140), Red 33 (Cl 17200), Butylphenyl
• Methylpropional Hydroxyisohexyl 3-Cyclohexene Carboxaldehyde, Linalool, Alpha-Isomethyl Ionone.
• the hair was left to process for 10 minutes with exposure to radiation, as in Example 7. After the processing time, the hair was left to rest for a further 10 minutes, without exposure to radiation. The hair was then thoroughly rinsed.
• the hair of the volunteers was examined.
• the hair had maintained a healthy appearance in all volunteers.
• a composition was prepared according to Example 6 with the difference that Ebest Fluorescein LTC (purchased from Fastcolors, UK) was also added to the mixture (in a concentration in weight percent based on the volume of the total composition of 0.001%) .
• composition was then applied to the hair of a volunteer, according to Example 7.
• Membranes obtained from Spectrum Laboratories, Inc. (CA, US) at room temperature (about 25 °C) , to remove any unreacted methacrylic anhydride and other side products of the reaction.
• the reaction product was then freeze-dried.
• the degree of substitution (DS) was determined by NMR by comparison of the pristine hydrolysed soy protein and hydrolysed soy protein methacrylate.
• hydrolysed soy protein powder (Kelisema, Italy) was dissolved in Milli Q water to 100 ml and gently stirred. The pH was adjusted to 7.5-8.5 using 2N NaOH (Sigma) . Subsequently, propargyl N-hydroxysuccimide ester ( Sigma-Aldrich, Sweden) solubilised in minimal quantity dimethyl sulfoxide (DMSO, Sigma) was added to the solution, drop-wise, while stirring for three hours at room temperature (25 °C) in molar excess at a 1:5 molar ratio with respect to the mole percent of lysine amine groups in hydrolysed soy protein (i.e. at a ratio of 1:5 of the mole percent of hydrolysed soy protein lysines to propargyl N-hydroxysuccimide ester) to modify the hydrolysed soy protein with reactive methacrylate functional groups.
• DMSO dimethyl sulfoxide
• the reaction product was then freeze-dried.
• the degree of substitution (DS) was determined by NMR by comparison of the pristine hydrolysed soy protein and hydrolysed soy protein methacrylate.

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