WO2004089321A1

WO2004089321A1 - Hair treatment compositions

Info

Publication number: WO2004089321A1
Application number: PCT/EP2004/003227
Authority: WO
Inventors: Julie Hutchison Cooper; Paul John Cunningham; Michael Douglas Eason; Ezat Khoshdel; Brodyck James Lachlan Royles
Original assignee: Unilever Plc; Unilever Nv; Hindustan Lever Limited
Priority date: 2003-04-09
Filing date: 2004-03-26
Publication date: 2004-10-21

Abstract

The invention provides a cosmetic and personal care composition comprising a film-forming aldonamide-functionalised polymer having a glass transition temperature of at least 20°C.

Description

HAIR TREATMENT COMPOSITIONS

Field of the Invention

The present invention relates to cosmetic and personal care compositions, such as hair styling compositions, containing aldonamide-functionalised polymers .

Background and Prior Art

The desire to have the hair retain a particular shape or style is widely held. The most common approach for accomplishing styling of hair is the application of a composition to dampened hair, after shampooing and/or conditioning, or to dry, styled hair. These compositions provide temporary styling benefits and can readily be removed by water or shampooing. To date, the materials employed in hair care compositions to provide styling benefits have generally been natural or synthetic resins and have been applied in the form of, for example, sprays, mousses, gels and lotions.

Recently, it has become desirable to have a high level of style retention, or strong hold, delivered from a hair spray composition. In a typical hair spray, hold is achieved by the use of commercially available styling polymers, such as AMPHOMER (TM) , supplied by National Starch Chemical Company, LUVIMER(TM) , supplied by BASF, GANTREZ (TM) , supplied by ISP Chemicals and also silicone graft copolymers, supplied by Mitsubishi Chemicals. A problem with many of the conventional styling polymers is that their relatively high molecular weight can lead to difficulties when processing and formulating them into compositions suitable for cosmetic and personal care use.

The present inventors have found that certain aldonamide- functionalised polymers produced by the reaction of polymeric amine with aldonolactone have film-forming properties despite a relatively low molecular weight when compared with conventional hair styling resins. The polymers according to the invention can be made water and/or alcohol- soluble, and are particularly suitable materials for use in cosmetic and personal care compositions, especially those for the styling of hair.

US 5,653,970 describes a class of heteroatom containing alkyl aldonamide compounds. These materials are not film forming and are used to improve foam, viscosity, clarity and skin feel in liquid personal care compositions such as body shampoos.

Aldonamide-functionalised organopolysiloxanes are disclosed as hair setting agents in EP 0 640 643. The materials disclosed in this publication are highly elastic thermoplastic elastomers with very low glass transition temperatures. These materials are not film-forming and hair styling compositions containing them require the further addition of conventional commercially available hair styling resins in order to provide adhesion to the hair fibre and hair set retention. Summary of the Invention

The present invention provides a cosmetic and personal care composition comprising a film-forming aldonamide- functionalised polymer having a glass transition temperature of at least 20°C.

Detailed Description

Aldonamide-functionalised polymer

An aldona ide is defined as the amide derived from an aldonic acid and/or its corresponding aldonolactone.

An aldonic acid is obtained by oxidising the aldehyde group of an aldehydic sugar (aldose) into a carboxyl group.

Aldonic acids may be represented by the general formula

GOCH₂(C*HOG)_nCOOH

wherein n is an integer of 0 or larger, C* denotes an asymmetric carbon atom, and each group G independently represents hydrogen or an attached mono-, di-, oligo- or polysaccharide.

Di-, oligo- or polysaccharide aldonic acids may be termed aldobionic acids, aldotrionic acids, aldotetraonic acids and so forth depending on the total number of saccharide units present in the molecule. The term ^λλ aldonic acid" as used herein is intended to include such materials. Usually at least part of the aldonic acid cyclises spontaneously on drying to form the corresponding lactone. Typically the hydroxyl group will be located at the γ or δ position of the lactone, depending on its ring size, to form γ-aldonolactone or δ-aldonolactone respectively.

Aldonamide-functionalised polymers for use according to the invention may generally be made by the reaction of aldonic acids and/or their corresponding aldonolactones with selected polymeric materials containing free amine groups (referred to below as "amine-containing polymers").

As an alternative route, it may in some cases be possible to react selected amine-containing monomers with aldonic acid and/or aldonolactone and then polymerise or copolymerise the functionalised monomer so obtained with suitable comonomers to form an aldonamide-functionalised polymer for use according to the invention.

The reaction conditions may be controlled so as to give a controlled degree of aldonamide substitution in the resulting aldonamide-functionalised polymer. Suitably the number of aldonamide substituents per molecule of aldonamide-functionalised polymer molecule ranges from 0.1 to 100, preferably from 1 to 80, more preferably from 10 to 50.

Preferred starting materials (i) and (ii) which may be reacted together to produce aldonamide-functionalised polymers for use according to the invention are described below:

(i) Aldonic acids/aldonolactones

Suitable aldonic acids and/or aldonolactones in the context of the present invention may be based on compounds comprising one or more saccharide units.

Any carbohydrate can be used as long as it has an aldehyde group available for oxidation to a carboxylic acid.

Examples of carbohydrates that can be oxidised to aldonic acids/aldonolactones include glyceraldehyde, erythrose, threose, ribose, arabinose, xylose, lyxose, allose, altrose, glucose, mannose, gulose, idose, galactose, talose, alloheptose, altroheptose, glucoheptose, mannoheptose, guloheptose, idoheptose, galactoheptose, taloheptose, glycerbiose, erythrobiose, threobiose, ribobiose, arabinobiose, xylobiose, lyxobiose, allobiose, altrobiose, glucobiose, mannobiose, gulobiose, idobiose, galactobiose, talobiose, alloheptobiose, altroheptobiose, glucoheptobiose, mannoheptobiose, guloheptobiose, idoheptobiose, galactoheptobiose, taloheptobiose, maltose, isomaltose, lactose, cellobiose, gentiobiose, laminaribiose, kojibiose, melibiose, nigerose, rutinose and sophorose.

Mixtures of any of the above may also be used.

It is believed that hydrogen-bonding interactions between carbohydrate chains in the aldonamide-functionalised polymers for use according to the invention contribute to their observed superior film-forming and hair styling properties. The stability of the hydrogen bonding that is formed between two carbohydrate chains depends on the stereochemistry that is present and the precise structure of the aldonic acids/aldonolactones used to form the aldonamide-functionalised polymer. As a further advantage, the carbohydrate chains may also provide moisturisation benefits to hair due to their natural tendency to adsorb moisture and associate with water.

Preferred aldonic acids/aldonolactones in the context of the present invention are D-gulonic-γ-lactone, δ-gluconolactone, L-glucono-1, 5-lactone, L-mannonic-γ-lactone, lactobiono-1, 5- lactone and mixtures thereof.

Especially preferred is δ-gluconolactone and lactobiono-1, 5- lactone .

( ii ) Amine-containing polymers

Examples of suitable amine-containing polymers in the context of the present invention are those having one or more backbones which incorporate carbon-carbon bonds or carbon-oxygen bonds and in which at least a portion of the free amine groups are primary amine groups . The polymer architecture may be linear, branched or hyperbranched. The free amine groups may suitably be present at the two or more ends of the polymer chain and/or along the one or more backbones of the polymer. The average molecular weight of the polymer when measured by Gel Permeation Chromatography suitably ranges from 1000 to 1,000,000 Daltons, preferably from 10,000 Daltons to 500,000 Daltons, more preferably from 20,000 Daltons to 100,000 Daltons.

Specific examples of suitable amine-containing polymers in the context of the present invention include synthetic polymers such as polyallylamine, polyvinylamine, polyaminoalkylacrylate/methacrylate (e.g. polyaminoethylacrylate/methacrylate) , and naturally derived polymers such as chitosan.

Particularly suitable amine-containing polymers in the context of the present invention are polyethyleneimines .

Polyethyleneimine (PEI) is a branched polymer which contains a mixture of primary, secondary and tertiary amine groups. PEI is commercially available under the trade name LUPASOL ® from BASF Chemicals.

Suitably the weight percentage of primary amine groups in the PEI ranges from 1 to 100wt%, preferably from 10 to 80wt%, more preferably from 20 to 60wt% .

Suitably the weight percentage of secondary amine groups in the PEI ranges from 1 to 50wt%, more preferably from 5 to 40wt%, most preferably from 10 to 20wt%.

Particularly preferred PEI starting materials in the context of the present invention are anhydrous and have a weight ratio of primary: secondary: tertiary amine groups in the range [0.9 to 1.1] : [0.8 to 1.3] : [0.5 to 0.8].

Commercially available examples of such materials include LUPASOL ® G-20 WF and LUPASOL ® WF, both ex BASF Chemicals.

Mixtures of any of the above-described amine-containing polymers (ii) may also be suitable.

Cosmetic and Personal Care Compositions

Compositions of the present invention are preferably formulated into hair care compositions, especially hairspray compositions, but can also be formulated into a wide variety of product types, including mousses, gels, lotions, tonics, sprays, shampoos, conditioners and rinses. It is preferable if the compositions are liquid. Preferably, the compositions are for use in styling human hair and, more preferably, they are packaged and labelled as such.

The content of aldonamide-functionalised polymer in compositions according to the invention suitably ranges from 0.1 to 20wt%, more preferably from 0.5 to 10wt%, most preferably from 1 to 5wt%.

Carriers

Compositions of the invention will generally comprise a cos etically acceptable carrier. Hair care compositions of the present invention can comprise a carrier, or a mixture of such carriers, which are suitable for application to the hair. The carriers are typically present at from about 0.5% to about 99.5%, preferably from about 5.0% to about 99.5%, more preferably from about 10.0% to about 98.0%, of the composition. As used herein, the phrase "suitable for application to hair" means that the carrier does not damage or negatively affect the aesthetics of hair or cause irritation to the underlying skin.

Carriers suitable for use with hair care compositions of the present invention include, for example, those used in the formulation of hair sprays, mousses, tonics, gels, shampoos, conditioners, and rinses. The choice of appropriate carrier will also depend on the particular aldonamide-functionalised polymer to be used, and whether the product formulated is meant to be left on the surface to which it is applied (e.g., hair spray, mousse, tonic, or gel) or rinsed off after use (e.g., shampoo, conditioner, rinse).

The carriers used herein can include a wide range of components conventionally used in hair care compositions. The carriers can contain a solvent to dissolve or disperse the particular aldonamide-functionalised polymer being used, with water, the Cl-Cβ alcohols, lower alkyl acetate and mixtures thereof being preferred. The carriers can also contain a wide variety of additional materials such as acetone, hydrocarbons (such as isobutane, hexane, decene) , halogenated hydrocarbons (such as Freons) and volatile silicones such as cyclomethicone.

When the hair care composition is a hair spray, tonic, gel, or mousse the preferred solvents include water, ethanol, volatile silicone derivatives, and mixtures thereof. The solvents used in such mixtures may be miscible or immiscible with each other. Mousses and aerosol hair sprays can also utilise any of the conventional propellants to deliver the material as a foam (in the case of a mousse) or as a fine, uniform spray (in the case of an aerosol hair spray) . Examples of suitable propellants include materials such as trichlorofluoromethane, dichlorodifluoromethane, difluoroethane, dimethylether, propane, n-butane or isobutane. A tonic or hair spray product having a low viscosity may also utilise an emulsifying agent. Examples of suitable emulsifying agents include nonionic, cationic, anionic surfactants, or mixtures thereof. If such an emulsifying agent is used, it is preferably present at a level of from about 0.01% to about 7.5% by weight based on total weight of the composition. The level of propellant can be adjusted as desired but is generally from about 3% to about 30% by weight based on total weight for mousse compositions and from about 15% to about 50% by weight based on total weight for aerosol hair spray compositions.

Suitable spray containers are well known in the art and include conventional, non-aerosol pump sprays i.e., "atomisers", aerosol containers or cans having propellant, as described above, and also pump aerosol containers utilising compressed air as the propellant.

The carrier can be in a wide variety of forms. For example, emulsion carriers, including oil-in-water, water-in-oil, water-in-oil-in-water, and oil-in-water-in-silicone emulsions, are useful herein. These emulsions can cover a broad range of viscosities, e.g., from about 100 cps to about 200,000 cps. These emulsions can also be delivered in the form of sprays using either mechanical pump containers or pressurised aerosol containers using conventional propellants. These carriers can also be delivered in the form of a mousse. Other suitable topical carriers include anhydrous liquid solvents such as oils, alcohols, and silicones (e.g., mineral oil, ethanol, isopropanol, dimethicone, cyclomethicone, and the like) ; aqueous-based single phase liquid solvents (e.g., hydro-alcoholic solvent systems) ; and thickened versions of these anhydrous and aqueous-based single phase solvents (e.g., where the viscosity of the solvent has been increased to form a solid or semi-solid by the addition of appropriate gums, resins, waxes, polymers, salts, and the like) .

Additional Components

A wide variety of additional components can be employed in cosmetic and personal care compositions according to the present invention.

Where the compositions are hair care compositions such as conditioners and rinses such additional components can include a wide variety of conditioning materials.

Where the compositions are hair care compositions such as shampoos, the additional components can include, for example, surfactants, suspending agents, and thickeners.

Where the compositions are hair care compositions such as hair styling compositions, the additional components can include further hair styling polymers. Examples of typical additional components include the following:

(i) further hair styling polymers (other than the film- forming aldonamide-functionalised polymer as described above) for hair styling compositions such as hair sprays, gels, and mousses. Hair styling polymers per se are well known articles of commerce and many such polymers are available commercially which contain moieties which render the polymers cationic, anionic, amphoteric or nonionic in nature. The polymers may be synthetic or naturally derived.

The amount of the polymer may range from 0.5 to 10%, preferably 0.75 to 6% by weight based on total weight of the composition.

Examples of anionic hair styling polymers are:

copolymers of vinyl acetate and crotonic acid;

terpolymers of vinyl acetate, crotonic acid and a vinyl ester of an alpha-branched saturated aliphatic monocarboxylic acid such as vinyl neodecanoate; copolymers of methyl vinyl ether and maleic anhydride (molar ratio about 1:1) wherein such copolymers are 50% esterified with a saturated alcohol containing from 1 to 4 carbon atoms such as ethanol or butanol;

acrylic copolymers containing acrylic acid or methacrylic acid as the anionic radical-containing moiety with other monomers such as: esters of acrylic or methacrylic acid with one or more saturated alcohols having from 1 to 22 carbon atoms (such as methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-butyl acrylate, t-butyl acrylate, t-butyl methacrylate, n-butyl methacrylate, n-hexyl acrylate, n- octyl acrylate, lauryl methacrylate and behenyl acrylate) ; glycols having from 1 to 6 carbon atoms (such as hydroxypropyl methacrylate and hydroxyethyl acrylate) ; styrene; vinyl caprolactam; vinyl acetate; acrylamide; alkyl acrylamides and methacrylamides having 1 to 8 carbon atoms in the alkyl group (such as ethacrylamide, t-butyl acrylamide and n-octyl acrylamide) ; and other compatible unsaturated monomers .

The polymer may also contain grafted silicone, such as polydimethylsiloxane .

Specific examples of suitable anionic hair styling polymers are:

RESYN® 28-2930 available from National Starch (vinyl acetate/crotonic acid/vinyl neodecanoate copolymer) ;

ULTRAHOLD®8 available from BASF (CTFA designation Acrylates/acrylamide copolymer) ;

the GANTREZ®ES series available from ISP corporation esterified copolymers of methyl vinyl ether and maleic anhydride) . Other suitable anionic hair styling polymers include carboxylated polyurethanes. Carboxylated polyurethane resins are linear, hydroxyl-terminated copolymers having pendant carboxyl groups. They may be ethoxylated and/or propoxylated at least at one terminal end. The carboxyl group can be a carboxylic acid group or an ester group, wherein the alkyl moiety of the ester group contains one to three carbon atoms. The carboxylated polyurethane resin can also be a copolymer of polyvinylpyrrolidone and a polyurethane, having a CTFA designation PVP/polycarbamyl polyglycol ester. Suitable carboxylated polyurethane resins are disclosed in EP 0 619 111 Al and US Patent No. 5,000,955. Other suitable hydrophilic polyurethanes are disclosed in US Patent Nos . 3,822,238; 4,156,066; 4,156,067; 4,255,550; and 4,743,673.

Amphoteric hair styling polymers which can contain cationic groups derived from monomers such as t-butyl aminoethyl methacrylate as well as carboxyl groups derived from monomers such as acrylic acid or methacrylic acid can also be used in the present invention. One specific example of an amphoteric hair styling polymer is Amphomer® (Octylacrylamide/acrylates/butylaminoethyl methacrylate copolymer) sold by the National Starch and Chemical Corporation.

Examples of nonionic hair styling polymers are homopolymers of N- vinylpyrrolidone and copolymers of N-vinylpyrrolidone with compatible nonionic monomers such as vinyl acetate. Nonionic polymers containing N- vinylpyrrolidone in various weight average molecular weights are available commercially from ISP Corporation - specific examples of such materials are homopolymers of N-vinylpyrrolidone having an average molecular weight of about 630,000 sold under the name PVP K- 90 and are homopolymers of N-vinylpyrrolidone having an average molecular weight of about 1,000,000 sold under the name of PVP K-120.

Other suitable nonionic hair styling polymers are cross- linked silicone resins or gums. Specific examples include rigid silicone polymers such as those described in EP-A-240 350 and cross-linked silicone gums such as those described in WO 96/31188.

Examples of cationic hair styling polymers are copolymers of amino-functional acrylate monomers such as lower alkyl aminoalkyl acrylate, or methacrylate monomers such as dimethylaminoethyl methacrylate, with compatible monomers such as N-vinylpyrrolidone, vinyl caprolactam, alkyl methacrylates (such as methyl methacrylate and ethyl methacrylate) and alkyl acrylates (such as ethyl acrylate and n-butyl acrylate) .

Specific examples of suitable cationic polymers are:

copolymers of N-vinylpyrrolidone and dimethylaminoethyl methacrylate, available from ISP Corporation as Copolymer 845, Copolymer 937 and Copolymer 958;

copolymers of N-vinylpyrrolidone and dimethylaminopropylacrylamide or methacrylamide, available from ISP Corporation as Styleze®CC10; copolymers of N-vinylpyrrolidine and dimethylaminoethyl methacrylate;

copolymers of vinylcaprolactam, N-vinylpyrrolidone and dimethylaminoethylmethacrylate;

Polyquaternium-4 (a copolymer of diallyldimonium chloride and hydroxyethylcellulose) ;

Polyquaternium-11 (formed by the reaction of diethyl sulphate and a copolymer of vinyl pyrrolidone and dimethyl aminoethylmethacrylate) , available from ISP as Gafquat® 734, 755 and 755N, and from BASF as Luviquat® PQ11;

Polyquaternium-16 (formed from methylvinylimidazolium chloride and vinylpyrrolidone) , available from BASF as Luviquat® FC 370, FC 550, FC 905 and HM-552;

Polyquaternium-46 (prepared by the reaction of vinylcaprolactam and vinylpyrrolidone with methylvinylimidazolium methosulphate) , available from BASF as Luviquat®Hold.

Examples of suitable naturally-derived polymers include shellac, alginates, gelatins, pectins, cellulose derivatives and chitosan or salts and derivatives thereof. Commercially available examples include Kytamer® (ex Amerchol) and Amaze® (ex National Starch) . With certain of the above-described polymers it may be necessary to neutralise some acidic groups to promote solubility/dispersibility. Examples of suitable neutralising agents include 2-amino-2- methyl-1, 3-propanediol (AMPD) ; 2- amino-2-ethyl-l, 3-propanediol (AEPD) ; 2-amino-2-methyl-l- propanol (AMP) ; 2-amino-l-butanol (AB) ; monoethanolamine (MEA) ; diethanolamine (DEA) ; triethanola ine (TEA) ; monoisopropanolamine (MIPA) ; diisopropanol-amine (DIPA) ; triisopropanolamine (TIPA) ; and dimethyl stearamine (DMS) . A long chain amine neutralising agent such as stearamidopropyl dimethylamine or lauramidopropyl dimethylamine may be employed, as is described in US 4,874,604. Also suitable are inorganic neutralisers, examples of which include sodium hydroxide, potassium hydroxide and borax. Mixtures of any of the above neutralising agents may be used. Amounts of the neutralising agents will range from about 0.001 to about 10% by weight of the total composition.

(ii) sunscreening agents such as 2-ethylhexyl p-methoxycinnamate, 2-ethylhexyl N,N-dimethyl-p- aminobenzoate, p-aminobenzoic acid, 2-phenylbenzimidazole-5- sulfonic acid, octocrylene, oxybenzone, homomenthyl salicylate, octyl salicylate, 4, 4 ' -methoxy-t- butyldibenzoylmethane, 4-isopropyl dibenzoylmethane, 3- benzylidene camphor, 3- (4-methylbenzylidene) camphor, titanium dioxide, zinc oxide, silica, iron oxide, and mixtures thereof.

(iii) anti-dandruff actives such as zinc pyrithione, piroctone olamine, climbazole, selenium disulphide, sulphur, coal tar, and the like. (iv) hair conditioning agents such as hydrocarbons, silicone fluids, and cationic materials. The hydrocarbons can be either straight or branched chain and can contain from about 10 to about 16, preferably from about 12 to about 16 carbon atoms. Examples of suitable hydrocarbons are decane, dodecane, tetradecane, tridecane, and mixtures thereof. Examples of suitable silicone conditioning agents useful herein can include either cyclic or linear polydimethylsiloxanes, phenyl and alkyl phenyl silicones, and silicone copolyols. Cationic conditioning agents useful herein can include quaternary ammonium salts or the salts of fatty amines.

(v) surfactants for hair shampoo and conditioner compositions. For a shampoo, the level is preferably from about 10% to about 30%, preferably from 12% to about 25%, by weight based on total weight of the composition. For conditioners, the preferred level of surfactant is from about 0.2% to about 3%, by weight based on total weight of the composition. Surfactants useful in compositions of the present invention include anionic, nonionic, cationic, zwitterionic and amphoteric surfactants.

(vi) carboxylic acid polymer thickeners for hair shampoo and conditioner compositions. These crosslinked polymers contain one or more monomers derived from acrylic acid, substituted acrylic acids, and salts and esters of these acrylic acids and the substituted acrylic acids, wherein the crosslinking agent contains two or more carbon-carbon double bonds and derived from a polyhydric alcohol. Examples of carboxylic acid polymer thickeners useful herein are those selected from the group consisting of carbomers, acrylates/C10-C30 alkyl acrylate crosspolymers, and mixtures thereof. Compositions of the present invention can comprise from about 0.025% to about 1%, more preferably from about 0.05% to about 0.75% and most preferably from about 0.10% to about 0.50% of the carboxylic acid polymer thickeners, by weight based on total weight of the composition.

(vii) emulsifiers for emulsifying the various carrier components of the compositions of the invention. Suitable emulsifier types include polyethylene glycol 20 sorbitan monolaurate (Polysorbate 20), polyethylene glycol 5 soya sterol, Steareth-20, Ceteareth-20, PPG-2 methyl glucose ether distearate, Ceteth-10, Polysorbate 80, cetyl phosphate, potassium cetyl phosphate, diethanolamine cetyl phosphate, Polysorbate 60, glyceryl stearate, PEG-100 stearate, and mixtures thereof. The emulsifiers can be used individually or as a mixture of two or more and can comprise from about 0.1% to about 10%, more preferably from about 1% to about 7%, and most preferably from about 1% to about 5%, by weight based on total weight of the composition.

(viii) vitamins and derivatives thereof (e.g., ascorbic acid, vitamin E, tocopheryl acetate, retinoic acid, retinol, retinoids, and the like.

(ix) cationic polymers (e.g., cationic guar gum derivatives such as guar hydroxypropyltrimonium chloride and hydroxypropyl guar hydroxypropyltrimonium chloride, available as the Jaguar® series from Rhone-Poulenc) . (x) preservatives, antioxidants, chelators and sequestrants; and aesthetic components such as fragrances, colourings, hair nutrients and essential oils.

Mixtures of any of the above listed additional components may also be present in compositions according to the invention.

The invention will now be illustrated by the following non- limiting Example:

EXAMPLE

Synthetic Method

An example for the preparation of an Aldonamide functional polyethyleneimine (PEI) is given below:

Modification of PEI G-20 WF (ex. BASF, Mn~1300 Da) with an equimolar amount of δ-gluconolactone, calculated with respect to the concentration of primary amine groups in the PEI G-20 WF that was used.

A stock solution was prepared containing 3g of anhydrous PEI G-20 WF dissolved with the addition of 10 mL anhydrous methanol to produce a low viscosity solution.

4.19 g of δ-gluconolactone was accurately weighed into an oven dry reactor flask, equipped with a magnetic stirrer bar and a guard tube that contained a suitable desiccant. To this 170 mL of anhydrous Methanol was added, and the resulting mixture was stirred at 55°C until a homogenous solution was obtained. The stock solution containing 3g of anhydrous PEI was then quickly added to the homogeneous solution of lactone, which on addition tuned milky white. The reaction mixture was then allowed to stir at 55°C overnight, after which time a solid was observed at the bottom of the flask. The solvent was removed by reduced pressure evaporation to yield a tacky solid, this was dissolved into water and then the product was freeze dried to yield a milky white tacky solid. Characterisation: NMR ^H-DzO) (ppm 2.5-3.6) : 3.35 (m, -CH₂CH₂NHC (=0) R, 1H) ; 2.75 (m,N(CH₂R^f )₃ + NH(CH₂R^f ' ) ₂.3H) .

Evaluation

The Aldonamide functional PEI obtained by the method described above is compatible with water and alcohol. In- vitro dynamic mechanical testing shows that the material is film forming and able to give styling properties for hair care products.

Claims

1. A cosmetic and personal care composition comprising a film-forming aldonamide-functionalised polymer having a glass transition temperature of at least 20°C.

2. A composition according to claim 1, in which the film- forming aldonamide-functionalised polymer is made by the reaction of aldonic acids and/or their corresponding aldonolactones with polyethyleneimines .

3. A composition according to claim 2, in which the film- forming aldonamide-functionalised polymer is made by the reaction of an aldonolactone selected from D- gulonic-γ-lactone, δ-gluconolactone, L-glucono-1, 5- lactone, L-mannonic-γ-lactone, lactobiono-1, 5-lactone and mixtures thereof, with anhydrous polyethyleneimine.

4. A composition according to any one of claims 1 to 3, which is formulated as a hairspray, gel or mousse.

5. A composition according to claim 4, further comprising an aerosol propellant.