GB2559312A

GB2559312A - Methods, compositions and uses relating thereto

Info

Publication number: GB2559312A
Application number: GB1616648.0A
Authority: GB
Inventors: John Dixon Nicholas; Robert Giles Matthew; Elizabeth Griffiths Kimberley; Gough Tony; Malcolm McRobbie Ian
Original assignee: Innospec Ltd
Current assignee: Innospec Ltd
Priority date: 2016-09-30
Filing date: 2016-09-30
Publication date: 2018-08-08
Also published as: GB201616648D0

Abstract

A method of treating a material, the method comprising contacting the material with a composition comprising a compound of formula (I): Wherein R is an optionally substituted hydrocarbyl group having at least five carbon atoms and R1 is hydrogen or a solubilising group is provided. The material may be a keratinous material such as hair. The R group may be phenyl or CH3(CH2)n wherein n is from 4 to 10. The composition may further comprise surfactants, an alpha-substituted aldehyde and/or a hydroxy aldehyde, a polycarboxylic acid derived chelating agent, an amine salt of a carboxylic acid and a cross-linking agent comprising two or more maleic acid derived reactive moieties with a linker have two or more amino groups. A hair care composition comprising a compound of formula (I) is also provided. The use of a compound of formula (I) to enhance at least one property of hair is outlined. A packaged hair colouring product comprising one or more compositions wherein the one or compositions together comprise at least one dye compound and/or one dye precursor compound a compound of formula (I) is provided.

Description

(71) Applicant(s):

Innospec Limited (Incorporated in the United Kingdom) Innospec Manufacturing Park, Oil Sites Road, ELLESMERE PORT, Cheshire, CH65 4EY, United Kingdom (72) Inventor(s):

Nicholas John Dixon Matthew Robert Giles Kimberley Elizabeth Griffiths Tony Gough Ian Malcolm McRobbie (56) Documents Cited:

WO 2015/128566 A WO 2008/156327 A

FR 002937543 A US 20170007528 A

US 20080313821 A

KR 1020090090138 KR 1020130114468 (58) Field of Search:

INT CL A61K, A61Q, C07D Other: EPODOC, WPI (74) Agent and/or Address for Service:

Appleyard Lees IP LLP

Clare Road, HALIFAX, West Yorkshire, ΗΧ1 2HY, United Kingdom (54) Title of the Invention: Methods, compositions and uses relating thereto Abstract Title: N-hydroxysuccinimidyl esters and their uses (57) A method of treating a material, the method comprising contacting the material with a composition comprising a compound of formula (I):

(ft

Wherein R is an optionally substituted hydrocarbyl group having at least five carbon atoms and R¹ is hydrogen or a solubilising group is provided. The material may be a keratinous material such as hair. The R group may be phenyl or CH₃(CH₂)_n wherein n is from 4 to 10. The composition may further comprise surfactants, an alpha-substituted aldehyde and/or a hydroxy aldehyde, a polycarboxylic acid derived chelating agent, an amine salt of a carboxylic acid and a cross-linking agent comprising two or more maleic acid derived reactive moieties with a linker have two or more amino groups. A hair care composition comprising a compound of formula (I) is also provided. The use of a compound of formula (I) to enhance at least one property of hair is outlined. A packaged hair colouring product comprising one or more compositions wherein the one or compositions together comprise at least one dye compound and/or one dye precursor compound a compound of formula (I) is provided.

METHODS, COMPOSITIONS AND USES RELATING THERETO

The present invention relates to a method of treating a material, to compositions for use in such methods and to uses relating thereto. In particular the present invention relates to a method of treating a keratinous material, especially hair, to provide a benefit to the material.

The appearance, condition and cleanliness of their hair are of great significance to many people. As a result there is a vast array of hair care products available offering a wide range of benefits and containing a huge number of different components. However popular hair styles change continually with fashion trends and technological developments in hair styling appliances means that there is a continuing need for different and improved hair care compositions. Furthermore as we learn more about the toxicity of certain chemicals and their environmental impact there is an increasing requirement to take these considerations into account when developing cosmetic products.

For example one previously used constituent of cosmetic hair care compositions is formaldehyde. However formaldehyde is a suspected carcinogen and thus its use in cosmetic compositions is now strictly regulated and highly undesirable.

It is an aim of the present invention to provide means for enhancing at least one property of a material.

FR2937543 describes the use of succinimidyl esters in hair care products. This document describes a very wide range of compounds, including di, tri and tetra esters containing 1,2, 3 or 4 succinimide residues. The present inventors have surprisingly found that some particular monoester compounds of this type provide especially effective colour protection.

According to a first aspect of the present invention there is provided a method of treating a material, the method comprising contacting the material with a composition comprising a compound of formula (I):

R¹«

R

O (I) wherein Ft is an optionally substituted hydrocarbyl group having at least 5 carbon atoms; and Ft¹ is hydrogen or a solubilising group.

The present invention relates to a method of treating a material. In preferred embodiments the material is a keratinous material. More preferably the material comprises keratinous fibres. Preferably the material is hair. The hair may be human or animal hair. In especially preferred embodiments the method of the present invention is a method treating human hair. Most preferably it is a method of treating human hair growing on the head.

However it will be appreciated that the method of the present invention can also be used to treat from hair that is not growing on the head, such as a wig or animal hair, for example wool.

The method of the present invention involves contacting the material, preferably hair, with a composition comprising a compound of formula (I).

According to a second aspect of the present invention there is provided a composition comprising a compound of formula (I):

wherein Ft is an optionally substituted hydrocarbyl group having at least 5 carbon atoms; and Ft¹ is hydrogen or a solubilising group.

Preferred features of the first and second aspects of the invention will now be described. Any feature may apply to any other aspect as appropriate.

Thus the method of the first aspect may involve contacting the material with a composition comprising a compound of formula (I) as defined in relation to the second aspect.

The composition of the second aspect of the present invention comprises a compound of formula (I):

O

(I) wherein R is optionally substituted hydrocarbyl group having at least 5 carbon atoms; and R¹ is hydrogen or a solubilising group.

R¹ is hydrogen or a solubilising group.

The solubilising group may be selected from any moiety which improves the water solubility of the compound of formula (I). Suitable solubilising group include hydroxy, alkoxy, polyalkoxy, alkylcarboxy, sulfo and phosphono groups.

Preferably R¹ is selected from hydrogen and a sulfonate moiety.

In some embodiments R¹ is a sulfonate moiety. By sulfonate moiety we mean to refer to a group of formula SO₃X where X is hydrogen, an alkali metal or ammonium ion.

Preferably R¹ is hydrogen.

Preferably R is an optionally substituted hydrocarbyl group having up to 36 carbon atoms, suitably up to 30 carbon atoms, preferably up to 24 carbon atoms, more preferably up to 20 carbon atoms, preferably up to 18 carbon atoms, more preferably up to 14 carbon atoms and most preferably up to 12 carbon atoms.

R may be an optionally substituted alkyl, alkenyl, aryl, alkaryl or aralkyl group having 5 to 36 carbon atoms, preferably 5 to 30 carbon atoms, preferably 5 to 20 carbon atoms, more preferably 5 to 12 carbon atoms.

In some embodiments Ft is an aryl group having 6 to 24, preferably 6 to 16, more preferably 6 to 10 carbon atoms.

In some embodiments Ft is an optionally substituted phenyl group. Ft may be phenyl.

In some embodiments Ft is an optionally substituted alkyl or alkenyl group having 5 to 24, preferably 5 to 16, suitably 6 to 10 carbon atoms.

Ft may be substituted with one or more substituents selected from keto, hydroxyl, halo, aryl, carboxy, acyl, nitro, amino, mercapto, alkoxy, sulfoxy, ester, nitrile, isonitrile or amide. The carbon backbone may be interrupted by one or more heteroatoms, for example, one or more oxygen, nitrogen or sulfur atoms.

In some preferred embodiments Ft is an unsubstituted alkyl group having 5 to 11, preferably 6 to 10, more preferably 7 to 9 carbon atoms.

Suitably Ft is selected from n-heptyl and n-nonyl.

Preferably Ft is n-heptyl.

Suitably the composition comprises a compound of formula (I) in an amount of at least 0.1 wt%, suitably at least 0.5 wt%, preferably at least 1 wt%, for example at least 1.5 wt%.

The composition may comprise a compound of formula (I) in an amount of up to 100 wt%, suitably up to 50 wt%, preferably up to 30 wt%, suitably 20 wt%, for example up to 10 wt%, for example up to 5 wt%, up to 3 wt% or up to 2.75 wt%.

In some embodiments the composition may suitably comprise from 0.1 to 10 wt%, preferably 0.5 to 5 wt%, for example 1 to 3 wt% of the compound of formula (I).

The composition of the second aspect may comprise two or more a compounds of formula (I). In such embodiments the above amounts refer to the total amount of all such compounds present in the composition.

The composition of the present invention may be provided in any suitable form. It may be in the form of a gel, paste, cream or wax. It may be in the form of a liquid composition. Such compositions may be in the form of a solution, dispersion or emulsion. It may be provided as a solid composition, for example as a powder or as a bar. In some embodiments a concentrate composition to be diluted prior to use may be provided. In some embodiments the composition of the third aspect may be part of precursor composition to be mixed with one or more further components prior to contact with the material.

The form and nature of the composition of the second aspect will depend on the intended use thereof. In the especially preferred embodiments the composition is a hair care composition.

The method of the first aspect of the present invention preferably provides a benefit to the material treated. Suitably the method enhances at least one property of the material that is treated according to the method.

In preferred embodiments the method is a method of treating hair that provides a beneficial effect to the hair. Suitably it enhances at least one property of the hair. Suitably the method of the first aspect involves contacting the hair with a composition of the second aspect.

The composition of the second aspect of the present invention is preferably a hair benefit composition. Suitably it enhances at least one property of the hair.

In some embodiments the composition and method of the present invention may provide a temporary change to a property of the hair, for example by providing increased shine or gloss, or improved softness or combability.

A temporary change in the property of the hair may be due to the composition coating the surface of the hair but forming a weak interaction such that the composition can be easily washed or brushed away.

In some preferred embodiments the composition and method of the present invention may provide a longer lasting benefit to the hair, for example, a wash-durable benefit.

The composition and method of the present invention may be useful in permanent waving or straightening of the hair.

The composition and method of the present invention may improve the strength of the hair.

The composition and method of the present invention may prevent or inhibit loss of protein from the hair and/or they may be used to bind extra protein to the hair.

The composition and method of the present invention may provide protection to the hair against damage. For example the composition and method of the present invention may protect against damage from heat or sunlight.

In some embodiments the composition and method of the present invention may provide chemical resistance, for example protection against chlorine and other compounds found in swimming pools and the like.

Suitably the composition and method of the present invention may enhance at least one property of hair selected from shine, gloss, softness, combability, strength, straightness, waviness, thermal durability and UV stability.

Preferably the invention provides one or more benefits selected from increased and/or permanent/semi-permanent gloss or shine, improved and/or permanent/semi-permanent combability, improved and/or permanent/semi-permanent strength, increased and/or permanent/semi-permanent softness, reduced protein loss, improved thermal durability, increased chemical resistance, permanent/semi-permanent waviness and and/or permanent/semi-permanent straightness.

Suitably the composition comprises one or more diluents or carriers. Preferred diluents and carriers are cosmetically approved compounds and suitable examples of these will be known to the person skilled in the art. Examples of suitable carriers include organic solvents (eg, hydrocarbon solvents (eg, isododecane), alcohols (eg, ethanol, propanol and butanol), propylene carbonate, benzyl alcohol, aliphatic or aromatic esters (eg, vegetable oils, isopropyl myristate, C12-15 alkyl benzoate), perfluorocarbon solvents, and silicone fluids.

In some embodiments the composition is an aqueous composition. Suitably water is the major solvent present in the composition. In some embodiments water provides for at least 50 wt% of all solvents present in the composition, preferably at least 60 wt%, more preferably at least 70 wt%, suitably at least 80 wt%, for example at least 90 wt% or at least 95 wt%. In some embodiments one or more further water miscible solvents may be present. Examples of suitable water miscible solvents include monohydric and polyhydric alcohols, for example ethanol, glycerol and isopropanol.

In some embodiments the composition of the present invention is not aqueous and the major diluent or carrier is an oleophilic material. In such embodiments the composition may comprise as a major solvent one or more higher fatty alcohols, a mineral oil and/or a vegetable oil.

In some embodiments the composition is substantially aqueous but the compound of formula (I) is dispersed within an oleophilic phase in which it is soluble.

In some embodiments the composition may consist essentially of one or more compounds of formula (I) and one more diluents or carriers. In preferred embodiments the composition comprises one or more further components. Suitable components are those typically used in personal care compositions and are known to the person skilled in the art.

As detailed above the compositions of the present invention may comprise different components depending on the intended use thereof. In some embodiments the composition may be used immediately after dyeing the hair. Alternatively the composition may be used one or more times as a hair treatment composition. In some embodiments it may be provided as a colour-loss prevention composition. Alternatively the composition may be in the form of shampoo, conditioner or hair styling product, for example a serum, wax, mousse, gel or spray or any other hair treatment form that could be used to provide general hair care benefits. Compositions which perform multiple functions, for example combined shampoo and conditioning compositions are also within the scope of the invention.

Suitably the composition comprises one or more additional components selected from surfactants (including anionic, amphoteric, nonionic and cationic surfactants); conditioning agents (including quaternary ammonium compounds, cationic polymers, silicones, synthetic or natural oils or resins etc), fatty alcohols, electrolytes or other rheology modifiers, opacifying/pearlising agents, scalp benefit agents, fragrances, dyes, UV filters, penetration enhancers (eg, propylene carbonate, benzyl alcohol etc), preservatives, antioxidants, emulsifiers, pH adjusting agents and buffers and styling polymers (eg, polyvinylpyrrolidone etc).

In some embodiments the composition comprises a pH adjusting agent.

Suitable pH adjusting agents for use herein may include lactic acid, sodium hydroxide, sodium phosphate and salts and buffers thereof.

The pH of the composition will depend on the intended use thereof. However in some embodiments the composition has a pH of between 3 and 9, preferably between 3.5 and 8, more preferably between 4 and 7, preferably between 4 and 6. In some other embodiments the compositions has a pH of between 8 and 13.

In some preferred embodiments the composition is a hair care composition. Suitable hair care compositions include shampoo compositions, conditioning compositions, hair styling compositions and hair permanent waving, relaxing or permanent straightening compositions, or hair colouring compositions.

Suitable further ingredients and amounts thereof to be used in hair care compositions will be known to the person skilled in the art. The relative ratios of the components and the formulation of such compositions would be within the competence of the skilled person.

Suitably the composition is a substantially aqueous composition, suitably comprising at least 50 wt% water, preferably at least 60 wt%, more preferably at least 70 wt%.

Suitably the composition comprises one or more surfactants. For example the composition may comprise from 0.1 to 60 wt% surfactants, preferably from 1 to 30 wt%, suitably from 5 to 25 wt%.

Suitably the composition comprises one or more anionic surfactants. For example the composition may comprise from 0.1 to 60 wt% anionic surfactants, preferably 1 to 30 wt%, suitably from 5 to 25 wt%.

In some embodiments the composition may comprise a quaternary ammonium salt, suitably in an amount of from 0.1 to 20 wt%, preferably 0.1 to 10 wt%.

In some embodiments the composition further comprises an aldehyde. Suitable aldehydes include hydroxy-substituted aldehydes and alpha-substituted aldehydes.

Thus the present invention may provide a hair care composition comprising a compound of formula (I) and an aldehyde which is an alpha-substituted aldehyde and/or a hydroxyaldehyde.

In such embodiments the compound of formula (I) is suitably present in an amount of from 0.1 to 50 wt%, preferably 0.1 to 10 wt%, more preferably 0.5 to 5 wt% and the aldehyde is suitably present in an amount of from 0.1 to 50 wt%, preferably 0.1 to 10 wt%, more preferably 0.5 to 5 wt%.

Some preferred aldehydes for use herein have from 3 to 20 carbon atoms, for example 3 to 16 carbon atoms.

Suitable aldehydes for use herein include 2-hydroxydecanal, 2-hydroxydodecanal, 2hydroxytetradecanal, 2-hydroxyhexanal, 2-hydroxyoctanal, 2-hydroxypropanal, glyceraldehyde, 2-hydroxybutanal, 3-hydroxybutanal, 4-hydroxybutanal, bromomalonaldehyde,

2-(2-hydroxyethoxy)acetaldehyde, 2-chloro octanal, 2-fluoro octanal, 2-bromo octanal, 6hydroxyhexanal, 3-hydroxypropanal and 4-hydroxy-but-2-enal.

In some embodiments the composition may comprise a first aldehyde having 3 to 9 carbon atoms, preferably 3 to 8 carbon atoms and a second aldehyde having 10 to 18 carbon atoms, preferably 10 to 16 carbon atoms, more preferably 10 to 14 carbon atoms.

Especially preferred aldehydes are α-hydroxy aldehydes. Suitable aldehydes include 2hydroxypropanal, 2-hydroxyhexanal, 2-hydroxyoctanal and glyceraldehyde.

In some embodiments the composition further comprises a chelating agent. Preferred chelating agents are polycarboxylic acid-derived chelating agents.

Thus the present invention may provide a hair care composition comprising a compound of formula (I) and a polycarboxylic acid-derived chelating agent.

In such embodiments the compound of formula (I) is suitably present in an amount of from 0.1 to 50 wt%, preferably 0.1 to 10 wt%, more preferably 0.5 to 5 wt% and the chelating agent is suitably present in an amount of from 0.1 to 50 wt%, preferably 0.1 to 10 wt%, more preferably 0.5 to 5 wt%.

Suitably the chelating agent is selected from glutamic acid Ν,Ν-diacetic acid (GLDA), diethylenetriaminepentaacetic acid (DTPA), imido disuccinic acid (IDS), ethylenediamine tetraacetic acid (EDTA), ethylenediamine disuccinic acid (EDDS), hydroxyethyl ethylenediaminetriacetic acid (HEDTA), citric acid and mixtures thereof.

In some preferred embodiments the chelating agent is selected from DTPA, GLDA, IDS and mixtures thereof. In some especially preferred embodiments the chelating agent is selected from DTPA, GLDA and mixtures thereof.

In some embodiments the composition further comprises an amine salt of a carboxylic acid. Preferred compounds of this type are amine salts of a carboxylic acid wherein the carboxylic acid has 4 to 10 carbon atoms.

In such embodiments the compound of formula (I) is suitably present in an amount of from 0.1 to 50 wt%, preferably 0.1 to 10 wt%, more preferably 0.5 to 5 wt% and the amine salt is suitably present in an amount of from 0.1 to 50 wt%, preferably 0.1 to 10 wt%, more preferably 0.5 to 5 wt%.

Thus the present invention may provide a hair care composition comprising a polycarboxylic acid-derived chelating agent and an amine salt of a carboxylic acid.

Suitably the carboxylic acid has 4 to 10 carbon atoms, preferably 6 to 8 carbon atoms.

Preferably the salt is of a secondary or tertiary alkylamine and/or alkanolamine or a substituted alkylene diamine. Triethanolamine and diethanolamine are especially preferred.

Most preferably the salt is the triethanolamine or diethanolamine salt of n-hexanoic acid or n-octanoic acid.

In some embodiments the composition further comprises an aldehyde that is an alphasubstituted aldehyde and/or a hydroxy aldehyde, and a polycarboxylic acid derived chelating agent.

In some embodiments the composition further comprises an aldehyde that is an alphasubstituted aldehyde and/or a hydroxy aldehyde, and an amine salt of a carboxylic acid.

In some embodiments the composition further comprises polycarboxylic acid derived chelating agent and an amine salt of a carboxylic acid.

In some embodiments the composition further comprises an aldehyde that is an alphasubstituted aldehyde and/or a hydroxy aldehyde, a polycarboxylic acid derived chelating agent, and an amine salt of a carboxylic acid.

In some embodiments the composition may further comprise a crosslinking agent comprising two or more reactive moieties and a linker. Compounds of this type are described for example in US2015/034117 and US2015/0034119.

In some embodiments the reactive moieties are activated carboxylic acid or sulfonic acid derivatives and the linkers are polyamino compounds which may form salts or covalent bonds with the reactive moieties.

In some embodiments the reactive moieties are maleic acid derivatives and the linker has two or more amino groups linked by alkylene or oxyalkylene chains. The crosslinking agent may be a maleimide or a maleic acid amine salt.

In some embodiments the reactive moieties are maleic acid ions and the linker comprises quaternary ammonium ions linked by alkylene or oxyalkylene chains.

Some preferred crosslinking agents have the following structures:

The crosslinking agent comprising two or more reactive moieties and a linker may be present in an amount of from 0.1 to 30 wt%, preferably 0.1 to 10 wt%, suitably 0.5 to 5 wt%.

In some embodiments the composition of the second aspect of the present invention is a shampoo composition.

Suitable shampoo compositions of the present invention may typically comprise 0.5 to 60 wt% of one or more anionic surfactants, preferably 1 to 50 wt%, more preferably 5 to 30 wt%, for example 8 to 20 wt% or 8 to 12 wt%; optionally from 0.1 to 30 wt% of amphoteric surfactants, preferably 1 to 15 wt%, for example 2 to 12 wt%; and optionally 0.1 to 40 wt% of non-ionic surfactants, preferably 0.5 to 30 wt%, for example 1 to 15 wt% or 2 to 12 wt%.

Shampoo compositions of the present invention may comprise one or more ingredients selected from anionic surfactants (eg, sodium laureth sulfate, sodium lauroyl methyl isethionate, sodium cocoyl methyl isethionate, sodium alpha-olefin sulfonate, sodium lauryl sulfoacetate, sodium monoalkyl phosphates, sodium dialkyl phosphates and sodium cocoyl methyl taurate), amphoteric surfactants (eg, cocam idopropyl betaine, sodium lauroamphoacetate, cocamidopropylhydroxy sultaine and disodium cocoamphodiacetate), foam boosters (eg, cocamide DEA, cocamide MEA, cocamide MIPA laureth-3), fatty alkyl alcohols (eg, cetyl alcohol, stearyl alcohol and behenyl alcohol), nonionic surfactants (eg, alkylpolyglucosides and alkyl ether ethoxylates), cationic polymers (eg, guar hydroxypropyl trimonium chloride, polyquaternium-10), silicones (eg, polydimethylsiloxanes such as dimethicone and dimethiconol), rheology modifiers (eg, carbomer, PEG-150 distearate and xanthan gum), synthetic or natural oils or resins (eg, mineral oil or vegetable oils), anti-dandruff agents (eg, piroctone olamine, zinc pyrithione and salicylic acid), styling agents (eg, polyisobutylene and polyvinyl pyrollidone/vinyl acetate copolymer), moisturising agents (eg, panthenol and glycerol), non-polymeric conditioning agents (eg, quaternary ammonium compounds such as behentrimonium chloride and stearalkonium chloride), opacifying/pearlising agents (eg, styrene/acrylates copolymer and ethylene glycol distearate), scalp benefit agents, fragrance, colouring agents, hair dyes, sunscreens, UV filters, preservatives, penetration enhancers (eg, propylene carbonate, benzyl alcohol etc) and diluents and carriers as defined herein.

Some preferred shampoo compositions of the present invention include 0.5 to 60 wt% of one or more anionic surfactants (for example, sodium laureth sulfate, sodium lauroyl methyl isethionate, sodium cocoyl isethionate, sodium alpha-olefin sulfonate, sodium lauryl sulfoacetate, sodium monoalkyl phosphates and sodium dialkyl phosphates); and 0 to 30 wt% of amphoteric surfactants (for example, cocamidopropyl betaine, sodium lauroamphoacetate and cocamidopropylhydroxy sultaine).

In some embodiments the composition of the second aspect of the present invention is a conditioning composition.

Suitable conditioning compositions of the present invention may typically comprise 0.1 to 20 wt% of one or more cationic surfactants, preferably 0.5 to 8 wt%, more preferably 1 to 4 wt%; and 0.1 to 20 wt% of one or more fatty alkyl alcohols, preferably 0.5 to 8 wt%, more preferably 1 to 4 wt%; and optionally 0.1 to 20 wt% of one or more non-ionic surfactants, preferably 0.5 to 8 wt%, more preferably 1 to 4 wt%; and optionally 0.1 to 20 wt% of one or more cationic polymers, preferably 0.5 to 8 wt%, more preferably 1 to 4 wt%.

Conditioning compositions of the present invention including rinse-off and leave-on conditioners (including ‘hair masks’) and hair shine or appearance enhancing products, antifrizz treatment serums and other treatments, either leave-in or rinse-off, designed to be applied to the hair immediately after colouring or any time thereafter, and hair-tonics. Such compositions may comprise one or more further ingredients selected from: cationic surfactants including mono-and di-fatty alkyl tertiary amines and quaternary ammonium compounds (eg, mono-and di-fatty alkyl quaternary ammonium compounds, such as cetrimonium chloride, steartrimonium chloride and behentrimonium chloride), fatty alkyl alcohols (eg, cetyl alcohol, stearyl alcohol and behenyl alcohol), nonionic surfactants (eg, alkylpolyglucosides and alkyl ether ethoxylates, eg, ceteareth-20), cationic polymers (eg, guar hydroxypropyl trimonium chloride, polyquaternium-10), silicones (eg, polydimethylsiloxanes such as dimethicone and dimethiconol), rheology modifiers (eg, hydroxyethyl cellulose and polyquaternium-37), moisturising agents (eg, panthenol and glycerol), non-polymeric conditioning agents (eg, quaternary ammonium compounds such as behentrimonium chloride and stearalkonium chloride), scalp benefit agents, fragrance, colouring agents, hair dyes, sunscreens, UV filters preservatives, penetration enhancers (eg, propylene carbonate, benzyl alcohol etc), and diluents and carriers as defined herein.

Some preferred conditioning compositions of the present invention include 0.1 to 20 wt% of cationic surfactants (for example mono- and di-fatty alkyl quaternary ammonium compounds, mono- and di-fatty alkyl tertiary amines), 0.1% to 20 wt% of fatty alkyl alcohols; and 0.1% to 20 wt% of non-ionic surfactants (for example ceteareth-20).

In some embodiments the composition of the second aspect of the invention is a hair styling composition.

Suitable hair styling compositions of the present invention may typically comprise from 0.1 to 40 wt% of one or more hair styling polymers, preferably from 0.1 to 30 wt%, more preferably from 0.5 to 10 wt%.

Hair styling compositions of the present invention (including gels, mousses with and without propellant, hair sprays with and without propellant, hair pomades, hair waxes, hair creams, hair brilliantines and compositions designed to be used in conjunction with heated styling appliances such as blow dryers, curling tongs, straightening irons, hot air hoods (as used for example in hair salons)) may comprise one or more further ingredients selected from: hair styling polymers (eg, polyvinylpyrrolidone, polyvinylpyrrolidone/vinyl acetate copolymers, octylacrylamide/acrylates/butylaminoethyl methacrylate copolymer, methyl vinyl ether/maleic anhydride copolymers and polyethylene waxes), rheology modifiers (eg, carbomers, acrylates copolymers, hydroxethylcellulose, xanthan gum and polyquaternium-37), aminomethyl propanol, fatty alkyl alcohols (eg, cetyl alcohol, stearyl alcohol and behenyl alcohol), ethanol, propyl alcohol, isopropyl alcohol, petrolatum, mineral oil, ozokerite, beeswax, carnauba wax, silicones (eg, polydimethylsiloxanes such as dimethicone and dimethiconol), polyethylene glycols, anionic surfactants (eg, sodium laureth sulfate and sodium lauroyl methyl isethionate), amphoteric surfactants (eg, cocamidopropyl betaine and disodium cocoamphodiacetate), nonionic surfactants (eg, alkylpolyglucosides and alkyl ether ethoxylates), cationic polymers (eg, guar hydroxypropyl trimonium chloride, Polyquaternium-10), silicones (eg, polydimethylsiloxanes such as dimethicone and dimethiconol), moisturising agents (eg, panthenol and glycerol), non-polymeric conditioning agents (eg, quaternary ammonium compounds such as behentrimonium chloride and stearalkonium chloride), scalp benefit agents, fragrance, colouring agents, hair dyes, sunscreens, UV filters, preservatives, penetration enhancers (eg, propylene carbonate, benzyl alcohol etc), and diluents and carriers as defined herein.

Some preferred hair styling compositions of the present invention include 0.1 to 40 wt% of one or more hair styling polymers/resins (for example, polyvinylpyrrolidone, polyvinylpyrrolidone/vinyl acetate copolymers, octylacrylamide/acrylates/butylaminoethyl methacrylate copolymer, methyl vinyl ether/maleic anhydride copolymers and polyethylene waxes).

Those skilled in the art will appreciate that it is possible to confer one or more attributes of hair conditioning, shine etc, and hair styling to the hair from a single product containing the appropriate ingredients thus compositions having such combinations of hair benefit effects are also covered in the invention.

In some embodiments the composition of the second aspect is a hair permanent waving composition.

Suitable hair permanent waving compositions of the present invention may typically comprise 0.1 to 20 wt% of one or more reducing agents, preferably from 0.5 to 15 wt%, more preferably 3 to 12 wt%.

Some preferred hair permanent waving compositions of the present invention include 0.5 to 15 wt% of one or more reducing agents (for example, as thioglycolic acid, ammonium thioglycolate, thiolactic acid, cysteamine, cysteine, glycerol monothioglycolate, sodium sulphite/bisulfite); alkalising agents (for example, ammonia, monoethanolamine) in an amount sufficient to adjust the pH of the reducing component to between pH 8-13. Hair permanent waving compositions are typically provided in a package with a second composition comprising 0.5 to 10 wt% of one or more oxidising agents (for example, hydrogen peroxide, sodium bromate, sodium percarbonate and sodium perborate) which are applied after the reducing agent composition has been applied, allowed to process and then rinsed off.

In some embodiments the composition of the second aspect of the present invention is a hair relaxing composition.

Hair relaxing compositions of the present invention may include one or more ingredients selected from sodium hydroxide, lithium hydroxide, potassium hydroxide, calcium hydroxide and guanidine carbonate. These components are suitably present in an amount of from 0.5 to 5 wt%.

Other types of permanent straightening compositions may include one or more ingredients selected from formaldehyde, glycoxylic acid, glutaraldehyde and glyoxyloyl carbocysteine. These components are suitably present in an amount of from 0.1 to 10 wt%.

The hair permanent waving, relaxing and permanent straightening compositions mentioned above may further include one or more additional ingredients selected from anionic surfactants (eg, sodium laureth sulfate and sodium lauroyl methyl isethionate), amphoteric surfactants (eg, cocamidopropyl betaine and disodium cocoamphodiacetate), quaternary ammonium compounds (eg, cetrimonium chloride, steartrimonium chloride and behentrimonium chloride), fatty alkyl alcohols (eg, cetyl alcohol, stearyl alcohol and behenyl alcohol), nonionic surfactants (eg, alkylpolyglucosides and alkyl ether ethoxylates), cationic polymers (eg, guar hydroxypropyl trimonium chloride, polyquaternium-10), silicones (eg, polydimethylsiloxanes such as dimethicone and dimethiconol), opacifying agents (eg, styrene acrylates copolymer), rheology modifiers (eg, hydroxyethyl cellulose and xanthan gum), moisturising agents (eg, panthenol and glycerol), non-polymeric conditioning agents (eg, quaternary ammonium compounds such as behentrimonium chloride and stearalkonium chloride), fragrance, sunscreens, UV filters, colouring agents and diluents and carriers as defined herein.

In some embodiments the composition of the second aspect of the present invention is a hair colouring composition.

Hair colouring compositions may include a dye compound and/or may include a dye precursor compound which forms an active dye in the hair in situ following admixture with an oxidising composition.

Oxidative hair colouring compositions of the present invention may include one or more intermediates, for example, p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p16 phenylenediamine, p-toluenediamine, p-aminophenol phenyl methyl pyrazolone, mphenylenediamine, resorcinol, 1-naphthol, 1-hydroxyethyl 4, 5-diamino pyrazole and maminophenol. These intermediates can be present in any combination and ratios at a total intermediate concentration of from 0.01% to 15%, depending upon the desired shade. Such compositions typically further include one or more alkalising agents, for example ammonia, ammonium hydroxide, sodium hydroxide and monoethanolamine. Developer compositions for oxidative dyeing include an oxidising agent, for example hydrogen peroxide, sodium bromate, sodium percarbonate or sodium perborate. These are typically present in an amount of from 0.1 to 30 wt%.

Direct-dye colour compositions of the present invention may include one of more direct dyes for example from the classes of nitrophenylenediamines (eg, 4-nitro-o-phenylenediamine etc), nitroaminophenols (eg, 2-amino-4-nitrophenol etc) and aminoanthraquinones (eg, Disperse Red 11 etc). These are typically present in an amount of 0.1 wt% to 20 wt%, depending on the desired shade.

In the method of the first aspect the material is contacted with a composition comprising compound of formula (I):

O

(I) wherein R is an optionally substituted hydrocarbyl group having at least 5 carbon atoms and R¹ is hydrogen or a sulfonate moiety.

The material, preferably hair, may be wet or dry when contacted with the composition.

Suitably the composition is applied to the material and spread across the surface of the material. In preferred embodiments in which the material is hair the composition may be rubbed into the hair in the manner of a shampoo and/or it may be combed through the hair.

The composition of the present invention may be left on the material or it may be removed from the material. Suitably it may be rinsed using warm water.

In some embodiments the composition may be contacted with the material, spread throughout and then immediately removed.

Suitably the composition may be removed from the material by rinsing, preferably by using water.

In some embodiments the composition may be washed from the material by washing with a detergent composition.

In some embodiments the composition may be mechanically removed from the material, for example by brushing.

In some embodiments the composition may be left on the material and not removed until the material is washed during a normal cycle.

In some embodiments in which the material is hair, the composition may be applied to the hair, spread throughout and rubbed into the hair, and then rinsed with water, in the manner of a shampoo.

In some embodiments in which the material is hair, the composition may be applied to the hair, spread throughout the hair (optionally with combing), left on the hair for a short period and then rinsed from the hair with water, in the manner of a conditioner.

In some embodiments in which the material is hair, the composition may be contacted with the hair and left on the hair in the manner of a styling product. The composition may be sprayed throughout the hair, rubbed throughout the hair, combed throughout the hair or otherwise spread through the hair in a manner known to those skilled in the art.

In embodiments in which the composition is left on the hair, it suitably remains on the hair until the hair is next washed, although some of the composition may be brushed out or rubbed away during normal activity.

In the method of the present invention the composition is suitably contacted with the material, preferably hair, at ambient temperature. In some embodiments the composition may be contacted with the material at a temperature greater than the ambient temperature.

In some embodiments the composition may be contacted with the hair and the hair carrying the compositions is then heated and/or manipulated and/or dried. Thus the hair may be dried using a hairdryer or straightened after the composition is applied.

The methods of the first and second aspect of the present invention may involve heating the hair. Such a heating step may involve commonly used heating techniques such as blow drying, or using tongs, straighteners or hoods etc.

The present invention may involve contacting the material with a composition comprising an alpha-substituted aldehyde once or more than once.

The invention may be used on a regular basis, for example every time hair (or another material) is washed. Alternatively the invention may be used periodically on a less frequent basis, for example, every week or every month.

It has been surprisingly found that the method of the present invention can significantly benefit the hair. This benefit may be a temporary benefit, a permanent benefit or a semipermanent benefit.

The method and composition of the present invention may benefit the hair by providing improved shine.

The method and composition of the present invention may benefit the hair by providing improved strength.

The method and composition of the present invention may benefit the hair by providing improved thermal protection.

The method and composition of the present invention may benefit the hair by providing permanent waving or straightening under mild conditions.

The method and composition of the present invention may benefit the hair by providing improved manageability and/or combability.

According to a third aspect of the present invention there is provided the use of a compound of formula (I):

to enhance at least one property of hair. Preferred features of the third aspect are as 5 defined in relation to the first and second aspects.

Preferred features of the third aspect are as defined in relation to the first and second aspects.

Claims

1. A method of treating a material, the method comprising contacting the material with a composition comprising a compound of formula (I):

(I) wherein R is an optionally substituted hydrocarbyl group having at least 5 carbon atoms, and R1 hydrogen or a solubilising group.

2. A method according to claim 1 wherein the material is a keratinous material.

3. A method according to claim 1 or claim 2 wherein the material is human hair or animal hair, preferably human hair.

4. A method according to claim 3 wherein the material is growing human hair or animal hair, preferably growing human hair.

A hair care composition comprising a compound of formula (I):

O (I) wherein R is an optionally substituted hydrocarbyl group having at least

5 carbon atoms; and R1 is hydrogen or a solubilising group.

6. A composition according to claim 5 comprising two or more compounds of formula (I)·

7. A method or composition according to any preceding claim wherein the composition comprising the compound of formula (I) is selected from a shampoo composition, a conditioning composition, a hair styling composition, a hair permanent waving composition, a hair relaxing composition, a hair permanent straightening composition or a hair colouring composition.

8. A method or composition according to any preceding claim wherein the composition comprising the compound of formula (I) further comprises 1 to 30 wt% of one or more surfactants, preferably one or more anionic surfactants

9. A method or composition according to any preceding claim wherein R is selected from an optionally substituted alkyl, alkenyl, or aryl group having 5 to 20 carbon atoms.

10. A method or composition according to any preceding claim wherein R is selected from phenyl and CH3(CH2)n wherein n is from 4 to 10.

11. A method or composition according to any preceding claim wherein R is n-heptyl.

12. A method or composition according to any preceding claim wherein R1 is hydrogen or a sulfonate moiety.

13. A method or composition according to any preceding claim wherein the composition comprising the compound of formula (I) further comprises an aldehyde which is an alpha-substituted aldehyde and/or a hydroxy aldehyde.

14. A method or composition according to any preceding claim wherein the composition comprising the compound of formula (I) further comprises a polycarboxylic acid derived chelating agent.

15. A method or composition according to any preceding claim wherein the composition comprising the compound of formula (I) further comprises an amine salt of a carboxylic acid.

16. A method or composition according to any preceding claim wherein the composition comprising the compound of formula (I) further comprises a crosslinking agent comprising two or more maleic acid derived reactive moieties and a linker having two or more amino groups.

17. A method or composition according to any preceding claim which provides one or more benefits selected from increased gloss or shine, improved combability, improved strength, increased softness, reduced protein loss, improved thermal durability, increased chemical resistance, increased waviness and increased

5 straightness.

18. A method according to claim 17 wherein the benefit may be temporary, semipermanent or permanent.

19. The use of a compound of formula (I):

(I) wherein R is an optionally substituted hydrocarbyl group having at least 5 carbon atoms and R1 is hydrogen or a solubilising agent to enhance at least one property of hair.

20. The use according to claim 19 of two or more compounds of formula (I) to

20 enhance at least one property of hair.

21. A packaged hair colouring product comprising one or more compositions wherein the one or more compositions together comprise at least one dye compound and/or one dye precursor compound and a compound of formula (I).

Intellectual

Property

Office

Application No: GB1616648.0 Examiner: Dr Alistair Longshaw